Furan-based cleansing surfactant

Abstract

A furan-based anionic sulphate free surfactant comprising: a) a head group comprising i) a furan ring ii) a sulphonate group attached to the furan ring b) an amide containing linker group; and c) a hydrophobic alkyl tail group having a carbon chain length of 8 to 18 wherein the furan-based anionic sulphate free surfactant has the structure of Formula (I) where R is a hydrophobic alkyl tail group having a carbon chain length of 8 to 18, 18:1 and 18:2 where R groups of different chain lengths can be used in combination as a blend, preferably a blend of chain lengths of C12 and C14, where X is a counterion, selected from organic and inorganic counterions; and its use in isotropic micellar phase cleansing compositions is used in an isotropic micellar phase cleansing composition further comprising a co-surfactant selected from a zwitterionic surfactant, an amphoteric surfactant and mixtures thereof; and water; wherein the composition has a viscosity in the range of from 1,000 to 50,000 mPa.s, preferably from 1,000 to 25,000, more preferably from 2,000 to 25,000 mPa.s, even more preferably from 2,100 to 15,000 mPa.s, when measured at 25 degrees C and 4s-1, using sandblasted 40mm parallel plates, on a Wingspan rheometer (TA instruments).

Description

[0001] FURAN-BASED CLEANSING SURFACTANT

[0002] Field of the Invention

[0003] The present invention relates to novel furan-based surfactants as well as cleansing compositions comprising them.

[0004] Background of the Invention

[0005] Consumers desire home and personal cleaning formulations that have an acceptable, and stable, viscosity so that the product can, for example, be applied in a controlled manner and readily spread in use.

[0006] Alternatives to traditional sulphate-based surfactants are increasingly in demand for use in home and personal cleansing formulations. “Sulphate free” cleaning surfactants have provided one such alternative and can be used with traditional co-surfactants. However, such surfactant systems have either proven difficulty to thicken and have limited solubility or limited pH window for use. Use of higher levels of salt and of polymeric thickeners result in cost and processing issues and do not always overcome the issues faced. It has thus been necessary to employ narrow ratios of anionic surfactant to co-surfactant, with higher proportions of the co-surfactant in order to boost viscosity. Such restrictions on formulation space are clearly limiting to product development and choice. Further, the modern consumer is increasingly demanding materials that are natural. Many traditional surfactants are petrochemically derived, and natural alternatives often cannot meet the same performance criteria.

[0007] WO 2015 / 084813 discloses a furan-based chemical comprising a furan group, hydrophilic group and hydrophobic group, wherein the hydrophilic group can be ionic, zwitterionic, or non-ionic, and further, and wherein said hydrophobic group can be alkyl or alkenyl, linear or branched moieties.

[0008] WO 2015 / 094970 discloses Linear mono- and dialkyl ethers of furan-2,5-dimethanol (FDM) and / or 2, 5-bis(hydroxymethyl)tetrahydrofuran (bHMTHF), methods for their preparation, and derivative chemical compounds thereof are described. George Kraus et al. “A Direct Synthesis of Renewable Sulfonate-Based Surfactants” Journal of Surfactants and Detergents vol. 16, no. 3, 1 May 2013 (2013-05-01), pages 317-320 discloses ester and ether linked furan-based surfactants with beta-hydroxy sulfonate headgroups. The compositions are described as being unstable at basic pH ranges.

[0009] Despite the prior art there remains a need for new non-sulphate based cleansing surfactants that are suitable for use in a wide range of commercially useful cleansing formulations and that meet the high performance criteria of traditional surfactants, including viscosity, stability, appearance, foam characteristics and workable pH range. There also remains a need for new high performing naturally derived alternatives to traditional surfactants that are petrochemically derived, including petrochemically derived sulphate free surfactants.

[0010] We have now found that a new furan-based anionic surfactant behaves like a traditional anionic surfactant. Unlike other sulphate free technologies, which are difficult to thicken, viscosity can be built across a wide range of surfactant ratios, when used in conjunction with co-surfactant(s). The compositions are stable across an unusually wide pH range. Advantageously, the surfactants can be used to produce transparent compositions which exhibit superior stability and excellent foaming characteristics. Advantageously, the furan-based anionic surfactant is naturally derived thus avoiding petrochemical based syntheses.

[0011] Definition of the Invention

[0012] Accordingly, and in a first aspect there is provided a furan-based anionic, sulphate-free surfactant comprising: a) a head group comprising: i) a furan ring; and ii) a sulphonate group directly attached to the furan ring; b) an amide containing linker group; and c) a hydrophobic alkyl tail group having a carbon chain length of from 8 to 18 wherein the furan-based anionic sulphate free surfactant has the structure of Formula (I): Formula (I) where R is a hydrophobic alkyl tail group having a carbon chain length of 8 to 18, 18:1 and 18:2 where R groups of different chain lengths can be used in combination as a blend, preferably a blend of chain lengths of C12 and C14; and where X is a counterion, selected from organic and inorganic counterions.

[0013] A second aspect of the invention provides an isotropic micellar phase cleansing composition comprising: a) the furan-based anionic, sulphate-free surfactant of the first aspect; b) a co- surfactant; and c) water; wherein the composition has a viscosity in the range of from 1 ,000 to 50,000 mPa.s, preferably from 1 ,000 to 25,000, more preferably from 2,000 to 25,000 mPa.s, even more preferably from 2,100 to 15,000 mPa.s, when measured at 25 degrees C and 4s-7, using sandblasted 40mm parallel plates, on a Wingspan rheometer.

[0014] A third aspect of the invention provides a method of cleaning a surface comprising applying to the surface a composition of the second aspect.

[0015] Detailed Description of the Invention

[0016] Many raw materials contain, what are known in the industry as, carry-over ingredients. These are often used for example as processing aids, preservatives, emulsifiers, etc. These carry-over ingredients are present in very small quantities (for example less than 0.05 wt % of the total composition) and perform a function for the raw material (for example as an emulsifier for a silicone). Carry-over ingredients are present in the full compositions at levels that are too low to have a material effect on the properties of the composition. They are not intended to be part of the invention.

[0017] The furan-based anionic sulphate free surfactant

[0018] The head group comprises: i) a furan ring; and ii) a sulphonate group directly attached to the furan ring. The sulphonate group is directly attached to the furan ring.

[0019] There is no chemical unit (group or moiety), for example a methylene group (CH2), between the sulphonate group and the furan ring.

[0020] The furan-based anionic sulphate free surfactant can be readily derived from bio-mass.

[0021] The amide linker group

[0022] The linker group comprises an amide and a saturated hydrocarbon chain. The saturated hydrocarbon chain is preferably selected from an ethylene group and a methylene group, most preferably is a methylene group (CH2).

[0023] The hydrophobic alkyl tail

[0024] The hydrophobic alkyl tail is an alkyl chain comprising a carbon chain length of 6 to 18, preferably from 8 to 16 carbon chains, most preferably from 10 to 14.

[0025] The hydrophobic alkyl chain can be linear or branched, preferably linear.

[0026] The hydrophobic alkyl chain can be saturated or unsaturated, preferably saturated. Preferred unsaturated chain include C18: 1 , C18:2 and C18:3, most preferred C18:1.

[0027] Blends of chain lengths may also be used, for example a blend of C12 and C14, preferably in a wt:wt ratio of 2:1.

[0028] The anionic sulphate free surfactant has a structure as defined in Formula (I):

[0029] Formula (I) where R is a hydrophobic alkyl tail group having a carbon chain length of from 8 to 18, preferably from 8 to 16 carbon chains, most preferably from 10 to 14; and where X is a counterion, suitably selected from organic and inorganic counterions. The counterion may be a proton. Preferred counterions include alkali metals, especially sodium and potassium, and ammonium and triethanolammonium cations.

[0030] The

[0031] The isotropic micellar phase cleansing composition comprises: a) the furan-based anionic sulphate free surfactant as described above; b) a co-surfactant; c) water; and d) optionally, an inorganic electrolyte; wherein the composition has a viscosity in the range of from 1,000 to 50,000 mPa.s, preferably from 1,000 to 25,000, more preferably from 2,000 to 25,000 mPa.s, even more preferably from 2,100 to 15,000 mPa.s, when measured at 25 degrees C and 4s-7, using sandblasted 40mm parallel plates, on a Wingspan rheometer (TA instruments).

[0032] The cleansing composition comprises a furan-based sulphate free anionic surfactant as described above.

[0033] Preferably, the cleansing composition is selected from a shampoo, body wash, face cleanser, hand wash.

[0034] More preferably the cleansing composition is selected from a hair shampoo, a body wash, a hand wash and a face cleanser. Most preferably, the cleansing composition is a shampoo or a body wash.

[0035] Preferably, the cleansing composition comprises an amount of furan-based anionic sulphate free surfactant of from 0.5 to 20 wt %, preferably from 1 to 15 wt %, more preferably from 2 to 12, even more preferably from 6 to 10, most preferably 3 to 8 wt %, by weight of total composition.

[0036] Preferably, the cleansing composition comprises a total amount of furan-based anionic sulphate free surfactant and co-surfactant of from 0.5 to 25 wt %, preferably from 1 to 20 wt %, more preferably from 8 to 12 wt % by weight of total composition. The cleansing composition has a weight ratio of furan-based anionic sulphate free surfactant to co-surfactant in the range of from 4:1 to 1:4, preferably from 7:3 to 3:7.

[0037] The composition may be a home care detergent composition, more preferably a hand dish wash detergent composition or a laundry detergent composition, most preferably a laundry detergent composition. Preferably the home care detergent composition, more preferably the laundry detergent composition is in the form of a liquid, solid, powder, pastille, bead or paste, preferably a liquid, solid or powder, more preferably a liquid.

[0038] If the composition is a home care composition, then preferably the composition additionally comprises an enzyme, preferably the detergent composition comprises from 0.05 to 5 wt.%, more preferably from 0.1 to 4 wt.%, more preferably from 0.5 to 3 wt.% of an enzyme, wherein the enzyme is preferably selected from one or more of a protease, amylase, mannanase, cellulase, lipase, pectate lyase, laccase, phosphodiesterase and mixtures thereof.

[0039] If the composition is a home care composition, then preferably the composition additionally comprises from 0.5 to 15 wt.%, more preferably from 0.75 to 15 wt.%, even more preferably from 1 to 12 wt.%, most preferably from 1.5 to 10 wt.% of cleaning boosters selected from antiredeposition polymers, soil release polymers, alkoxylated polycarboxylic acid esters and mixtures thereof, more preferably selected from antiredeposition polymers, and soil release polymers.

[0040] Preferably the antiredeposition polymers are alkoxylated polyamines; and / or wherein the soil release polymer is a polyester soil release polymer.

[0041] If the composition is a home care composition, preferably a laundry composition, then preferably the composition additionally comprises from 0.05 to 8 wt.%, preferably from 0.1 to 5 wt.%, more preferably from 0.5 to 2 wt.% of a sequestrant, preferably the sequestrant is preferably selected from HEDP, DTPMP, EDTA, MGDA, GLDA or citric acid.

[0042] The following are exemplar detergent compositions for laundry and home care applications, where “Furan Surfactant” is the furan-based anionic sulphate free surfactant described herein. Low Foam Laundry Liquid

[0043] High Foam Laundry Liquid Sulphate / Carbonate Powder

[0044] Salt / Carbonate Powder Hand Dish Wash

[0045] The amphoteric or zwitterionic co-surfactant

[0046] Preferably, the co-surfactant is selected from a zwitterionic surfactant, an amphoteric surfactant and mixtures thereof.

[0047] Examples of suitable amphoteric and zwitterionic co-surfactants include alkyl amine oxides (for example lauryl amine oxide); alkyl betaines, alkyl amidopropyl betaines, alkyl sulphobetaines; alkyl amphoacetates (for example sodium cocoamphoacetate); alkyl amphopropionates, alkylamphoglycinates; alkyl amidopropyl hydroxysultaines; and mixtures thereof.

[0048] Preferably, the amphoteric or zwitterionic co-surfactant is selected from alkyl betaines, alkyl amidopropyl betaines, alkyl hydroxysultaines, alkyl amidopropyl hydroxy sultaines, and mixtures thereof.

[0049] Most preferred examples of amphoteric and zwitterionic surfactants for use in the compositions of the invention include lauryl betaine, cocam idopropyl betaine, lauryl hydroxysultaine, cocamidopropyl hydroxysultaine and mixtures thereof.

[0050] A particularly preferred amphoteric or zwitterionic co-surfactant is selected from cocamidopropyl betaine and lauryl hydroxysultaine. The zwitterionic or amphoteric co-surfactant is preferably present in an amount of from 1 to 10 wt %, preferably 1.5 to 9 wt %, more preferably 2 to 9 wt %, based on the weight of the total composition.

[0051] The compositions of the invention preferably comprise from 50 to 98, preferably 60 to 95 wt %, most preferably 70 to 90 wt % water by weight of the total composition.

[0052] Concentrated compositions may comprise less water.

[0053] Preferably the pH range of the cleansing composition is from 3.5 to 9, more preferably from 4 to 8, most preferably from 4.2 to 7.

[0054] The

[0055] The compositions of the invention preferably comprise an inorganic electrolyte. Suitable inorganic electrolytes for use in the invention include metal chlorides (such as sodium chloride, potassium chloride, calcium chloride, magnesium chloride, zinc chloride, ferric chloride and aluminum chloride) and metal sulphates (such as sodium sulphate and magnesium sulphate). The inorganic electrolyte is used to provide viscosity to the composition.

[0056] Examples of preferred inorganic electrolytes for use in the invention include sodium chloride, potassium chloride, magnesium sulphate and mixtures thereof, most preferably sodium chloride.

[0057] Mixtures of any of the above described materials may also be suitable.

[0058] Where present, the level of inorganic electrolyte in compositions of the invention ranges from 0.1 to 3%, preferably from 0.25 to 2.5% (by total weight of the composition).

[0059] It is intended that the inorganic electrolyte is distinct from any inorganic electrolytes that may be present in the raw materials of the invention, as “carry over”.

[0060] The viscosity of the composition suitably ranges from 1 ,000 to 50,000 mPa.s, preferably from 1 ,000 to 25,000, more preferably from 2,000 to 25,000 mPa.s, when measured at 25 degrees C and 4s-7, using sandblasted 40mm parallel plates, on a Wingspan rheometer (TA instruments). At these ranges the composition is pourable yet thick enough to satisfy the consumer desire for thick compositions.

[0061] The isotropic micellar phase cleansing composition is transparent or translucent, preferably transparent.

[0062] A suitable method of assessing transparency is to measure turbidity. UV-vis spectrometry may be used to determine the turbidity of the formulation. An example of a suitable spectrophotomer is a Jasco V-650 spectrophotometer.

[0063] Translucency (or turbidity) in a liquid product is due to suspended or colloidal particles that cause light to be scattered rather than transmitted in straight lines through the sample.

[0064] Turbidity may be calculated using the equation, where turbidity is 2.3 multiplied by absorbance divided by the path length of the sample, i.e. Turbidity = (2.3 x A / L); where A is the absorbance measured from the sample at 750 nm and L is the path length. Preferably a path length of 1.0 cm is used.

[0065] A composition is said to be transparent when the turbidity is lower than 1 cm-1, preferably lower than 0.5 cm-1, more preferably lower than 0.4 cm-1, even more preferably lower than 0.25 cm-1most preferably lower than 0.1 cm-1, as measured using a UV / visible spectrophotometer and applying the equation turbidity = (2.3*A / L), where A is the absorbance measured from the sample at 750 nm and L is the path length.

[0066] Further Ingredients

[0067] Additional anionic surfactant

[0068] The compositions may comprise additional anionic surfactants. Suitable examples include nonsulphate containing surfactants such as fatty acyl derivatives, preferably lauroyl or cocoyl, of glycinates, taurates, isethionates and sarcosinates; and alpha olefin sulphonates and mixtures thereof.

[0069] Other examples include sulphate containing surfactants for example sulphated surfactants such as alkyl sulphates and alkyl ethoxy sulphates for example sodium lauryl ether sulphate (SLES) and trideceth sulphate. Where present, the total level of furan-based anionic sulphate free surfactant and additional anionic surfactant will be from 0.5 to 20 wt %, preferably from 1 to 15 wt %, more preferably from 2 to 10, even more preferably from 3 to 8 wt %, by weight of total composition.

[0070] Other Ingredients

[0071] A composition of the invention may contain further optional ingredients to enhance performance and / or consumer acceptability. Examples of such ingredients include, for example, fragrance, dyes and pigments, pH adjusting agents (for examples organic acids, sodium hydroxide), pearlescers, opacifiers, preservatives, antimicrobials, structurants, solvents, feel modifying polymers. Each of these ingredients will be present in an amount effective to accomplish its purpose. Generally, these optional ingredients are included individually at an amount of up to 5% (by weight based on the total weight of the composition).

[0072] The compositions for use in the invention preferably comprise a preservative. Preferred preservatives include sodium benzoate and caprylyl glycol.

[0073] Where present, the preservative is preferably present in an amount of from 0.01 to 2 wt %, more preferably 0.01 to 1 wt %, most preferably 0.1 to 1 wt %, by total weight of the composition.

[0074] Method of making furan-based sulphate free anionic surfactant

[0075] The furan-based sulphate free anionic surfactant of the present invention may be made by any suitable process. Examples of a suitable process is as follows.

[0076] Amidation reaction: Furfurylamine (1 eg) and triethylamine (1.1 eg) were mixed in ethyl acetate (6 g / 100 ml) at 0 °C. The acyl chloride (1.05 eg) was then added dropwise. After complete addition, the mixture was heated to 70 °C and stirred for 16h. TLC (EtOAc:PE 2:1 , PMDA stain) showed a new spot with Rf = 0.5 and consumption of starting furfurylamine. Water was added to guench, the crude was filtered hot and the solid precipitate was washed with further hot ethyl acetate. The filtrate was evaporated to dryness, affording the corresponding furfurylamide as an off-white solid (82-99%).

[0077] N-(furan-2-ylmethyl)dodecanamide. Using furfurylamine (15 g), dodecanoyl chloride (38.5 ml) and triethylamine (4.0 ml). Pale yellow solid, 99% yield.1H NMR (MeOD), 5 (ppm): 7.40, dd, 1 H, J = 0.8 and 1.8 Hz; 6.33-6.32, m, 1 H; 6.22, dd, 1 H, J = 0.8 and 3.1 Hz; 4.33, s, 2 H; 2.19, t, 2 H, J = 7.0 Hz; 1.61-1.58, m, 2 H; 1.31-1.28, m, 16 H; 0.90, t, 1 H, J = 6.7 Hz. Sulfonation reaction: Furfurylamide (1 eq) was dissolved in acetonitrile (20 g / 100 ml) at 0 °C. Chlorosulfonic acid (3 eq) was then added dropwise. After complete addition, the reaction was warmed up to RT and stirred for 3h.1H NMR (MeOD) showed disappearance of the proton at 7.4 ppm, corresponding to C4-H in the furan ring, confirming substitution at this position. Water was carefully added, followed by NaOH (50% in water) until pH 8. Most of the solvent was removed in vacuo and the residue was resuspended in acetone. The solid precipitate was collected, washed with hot acetone, dried and subjected to soxhlet extraction in methanol for 48h. This solution was then treated with activated carbon at reflux for 3h. The filtrate was evaporated to dryness, affording the corresponding sulphonated product as a pale-yellow solid (62-76%).

[0078] 5-(dodecanamidomethyl)furan-2-sulfonate. Using / \ / -(furan-2-ylmethyl)dodecanamide (40 g) and chlorosulfonic acid (24 ml). Off-white solid, 65% yield.1H NMR (DMSO-de), 5 (ppm): 8.28, t, 1 H, J = 5.6 Hz; 6.28, d, 1 H, J = 3.2 Hz; 6.08, d, 1 H, J = 3.2 Hz; 4.20, d, 2 H, J = 5.6 Hz; 2.09, t, 2 H, J = 7.2 Hz; 1.52-1.45, m, 2 H; 1.27-1.24, m, 16 H; 0.85, t, 1 H, J = 6.7 Hz.

[0079] Optionally, a shampoo composition in accordance the invention may contain further ingredients, (non-limiting examples of which are described below) to enhance performance and / or consumer acceptability.

[0080] Cationic polymers are preferred ingredients in a shampoo composition for use in the invention for enhancing conditioning performance.

[0081] Suitable cationic polymers may be homopolymers which are cationically substituted or may be formed from two or more types of monomers. The weight average (Mw) molecular weight of the polymers will generally be between 100 000 and 3 million daltons. The polymers will have cationic nitrogen containing groups such as quaternary ammonium or protonated amino groups, or a mixture thereof. If the molecular weight of the polymer is too low, then the conditioning effect is poor. If too high, then there may be problems of high extensional viscosity leading to stringiness of the composition when it is poured.

[0082] The cationic nitrogen-containing group will generally be present as a substituent on a fraction of the total monomer units of the cationic polymer. Thus when the polymer is not a homopolymer it can contain spacer non-cationic monomer units. Such polymers are described in the CTFA Cosmetic Ingredient Directory, 3rd edition. The ratio of the cationic to non-cationic monomer units is selected to give polymers having a cationic charge density in the required range, which is generally from 0.2 to 6 meq / g, preferably 0.2 to 3.0 meq / g. The cationic charge density of the polymer is suitably determined via the Kjeldahl method as described in the US Pharmacopoeia under chemical tests for nitrogen determination.

[0083] Suitable cationic polymers include, for example, copolymers of vinyl monomers having cationic amine or quaternary ammonium functionalities with water soluble spacer monomers such as (meth)acrylamide, alkyl and dialkyl (meth)acrylamides, alkyl (meth)acrylate, vinyl caprolactone and vinyl pyrrolidine. The alkyl and dialkyl substituted monomers preferably have C1-C7 alkyl groups, more preferably C1-3 alkyl groups. Other suitable spacers include vinyl esters, vinyl alcohol, maleic anhydride, propylene glycol and ethylene glycol.

[0084] The cationic amines can be primary, secondary or tertiary amines, depending upon the particular species and the pH of the composition. In general, secondary and tertiary amines, especially tertiary, are preferred.

[0085] Amine substituted vinyl monomers and amines can be polymerised in the amine form and then converted to ammonium by quaternization.

[0086] The cationic polymers can comprise mixtures of monomer units derived from amine- and / or quaternary ammonium-substituted monomer and / or compatible spacer monomers.

[0087] Suitable (non-limiting examples of) cationic polymers include: cationic diallyl quaternary ammonium-containing polymers including, for example, dimethyldiallylammonium chloride homopolymer (PDADMAC) and copolymers of acrylamide and dimethyldiallylammonium chloride, referred to in the industry (CTFA) as Polyquaternium 6 and Polyquaternium 7, respectively; mineral acid salts of amino-alkyl esters of homo-and co-polymers of unsaturated carboxylic acids having from 3 to 5 carbon atoms, (as described in U.S. Patent 4,009,256); cationic polyacrylamides(as described in WO95 / 22311). Other cationic polymers that can be used include cationic polysaccharide polymers, such as cationic cellulose derivatives, cationic starch derivatives, and cationic guar gum derivatives.

[0088] Cationic polysaccharide polymers suitable for use in compositions for use in the invention include monomers of the formula:

[0089] A-O-[R-N+(R1)(R2)(R3)X-], wherein: A is an anhydroglucose residual group, such as a starch or cellulose anhydroglucose residual. R is an alkylene, oxyalkylene, polyoxyalkylene, or hydroxyalkylene group, or combination thereof. R1, R2and R3independently represent alkyl, aryl, alkylaryl, arylalkyl, alkoxyalkyl, or alkoxyaryl groups, each group containing up to about 18 carbon atoms. The total number of carbon atoms for each cationic moiety (i.e., the sum of carbon atoms in R1, R2and R3) is preferably about 20 or less, and X is an anionic counterion.

[0090] Another type of cationic cellulose includes the polymeric quaternary ammonium salts of hydroxyethyl cellulose reacted with lauryl dimethyl ammonium-substituted epoxide, referred to in the industry (CTFA) as Polyquaternium 24. These materials are available from the Amerchol Corporation, for instance under the tradename Polymer LM-200.

[0091] Other suitable cationic polysaccharide polymers include quaternary nitrogen-containing cellulose ethers (e.g. as described in U.S. Patent 3,962,418), and copolymers of etherified cellulose and starch (e.g. as described in U.S. Patent 3,958,581). Examples of such materials include the polymer LR and JR series from Dow, generally referred to in the industry (CTFA) as Polyquaternium 10.

[0092] A particularly suitable type of cationic polysaccharide polymer that can be used is a cationic guar gum derivative, such as guar hydroxypropyltrimethylammonium chloride (commercially available from Rhodia in their JAGUAR trademark series). Examples of such materials are JAGUAR C13S, JAGUAR C14 and JAGUAR C17.

[0093] Mixtures of any of the above cationic polymers may be used.

[0094] Cationic polymer will generally be present in a shampoo composition for use in the invention at levels of from 0.01 to 5%, preferably from 0.02 to 1%, more preferably from 0.05 to 0.8% by total weight of cationic polymer based on the total weight of the composition. Silicone

[0095] The compositions of the invention can contain emulsified droplets of a silicone conditioning agent, which is preferably not hydrophobically modified.

[0096] Suitable silicones include polydimethylsiloxanes which have the CTFA designation dimethicone. Also suitable for use compositions of the invention are polydimethyl siloxanes having hydroxyl end groups, which have the CTFA designation dimethiconol. Preferably, the silicone is selected from the group consisting of dimethicone, dimethiconol, amodimethicone and mixtures thereof. Also preferred are blends of amino-functionalised silicones with dimethicones.

[0097] The internal phase viscosity of the emulsified silicone itself (not the emulsion or the final hair conditioning composition) is typically at least 10,000 cst at 25 °C the viscosity of the silicone itself is preferably at least 60,000 cst, most preferably at least 500,000 cst, ideally at least 1 ,000,000 cst. Preferably the viscosity does not exceed 109cst for ease of formulation.

[0098] Emulsified silicones for use in the compositions of the invention will typically have a D90 silicone droplet size in the composition of less than 30, preferably less than 20, more preferably less than 10 micron, ideally from 0.01 to 1 micron. Silicone emulsions having an average silicone droplet size (D50) of 0.15 micron are generally termed microemulsions.

[0099] Silicone particle size may be measured by means of a laser light scattering technique, for example using a 2600D Particle Sizer from Malvern Instruments.

[0100] Examples of suitable pre-formed emulsions include Xiameter MEM 1785 and microemulsion DC2-1865 available from Dow Corning. These are emulsions / microemulsions of dimethiconol. Cross-linked silicone gums are also available in a pre-emulsified form, which is advantageous for ease of formulation.

[0101] A further preferred class of silicones for inclusion in compositions of the invention are amino functional silicones. By "amino functional silicone" is meant a silicone containing at least one primary, secondary or tertiary amine group, or a quaternary ammonium group. Examples of suitable amino functional silicones include: polysiloxanes having the CTFA designation "amodimethicone". A preferred amodimethicone is available from Dow Corning as DC 7134.

[0102] Specific examples of amino functional silicones suitable for use in the invention are the aminosilicone oils DC2-8220, DC2-8166 and DC2-8566 (all ex Dow Corning). Suitable quaternary silicone polymers are described in EP-A-0 530 974. A preferred quaternary silicone polymer is K3474, ex Goldschmidt.

[0103] Also suitable are emulsions of amino functional silicone oils with non ionic and / or cationic surfactant.

[0104] Pre-formed emulsions of amino functional silicone are also available from suppliers of silicone oils such as Dow Corning and General Electric. Specific examples include DC939 Cationic Emulsion and the non-ionic emulsions DC2-7224, DC2-8467, DC2-8177 and DC2-8154 (all ex Dow Corning).

[0105] The total amount of silicone is preferably from 0.1 wt % to 10 wt % of the total composition more preferably from 0.1 wt % to 5 wt %, most preferably 0.25 wt % to 3 wt % is a suitable level.

[0106] The compositions of the present invention may include an appearance modifier to improve visual appearance and / or consumer appeal of the product. Most preferably the appearance modifier is a pearlescer selected from mica, titanium dioxide, titanium dioxide coated mica, ethylene glycol distearate (INCI glycol distearate) and mixtures thereof.

[0107] Nonionic Surfactants

[0108] One or more nonionic surfactants may be used in the cleansing composition of the present invention.

[0109] Nonionic surfactants are preferably used at levels as low as 0.5, 1 , 1.5 or 2% by wt. and at levels as high as 6, 8, 10 or 12% by wt. The nonionics which may be used include in particular the reaction products of compounds having a hydrophobic group and a reactive hydrogen atom, for example aliphatic alcohols, acids, amides or alkylphenols with alkylene oxides, especially ethylene oxide either alone or with propylene oxide. Specific nonionic detergent compounds are alkyl (C6 C22) phenols ethylene oxide condensates, the condensation products of aliphatic (C8- C18) primary or secondary linear or branched alcohols with ethylene oxide, and products made by condensation of ethylene oxide with the reaction products of propylene oxide and ethylenediamine. Other so-called nonionic detergent compounds include long chain tertiary amine oxides, long chain tertiary phosphine oxides and dialkyl sulphoxide, and the like. Preferred nonionic surfactants include fatty acid / alcohol ethoxylates having the following structures a) HOCH2(CH2)n(CH2CH2O)xH or b) HOOC(CH2)m(CH2CH2O)yH; where m, n are independently <18; and x, y are independently >1. preferably m, n are independently 6 to 18; x, y are independently 1 to 30; c) HOOC(CH2)j-CH=CH (CH2)k(CH2CH2O)zH; where i, k are independently 5 to 15; and z is independently 5 to 50. Preferably i, k are independently 6 to 12; and z is independently 15 to 35.

[0110] The nonionic surfactant may also include a sugar amide, such as a polysaccharide amide. Specifically, the surfactant may be one of the lactobionamides described in U.S. Pat. No. 5,389,279 to Au et al. titled "Compositions Comprising Nonionic Glycolipid Surfactants issued Feb. 14, 1995; which is hereby incorporated by reference or it may be one of the sugar amides described in U.S. Pat. No. 5,009,814 to Kelkenberg, titled "Use of N-Poly Hydroxyalkyl Fatty Acid Amides as Thickening Agents for Liquid Aqueous Surfactant Systems" issued Apr. 23, 1991 ; hereby incorporated into the subject application by reference.

[0111] Skin Benefit Agent

[0112] The composition of the invention may comprise a skin benefit agent. The skin benefit agent is preferably selected from optical and sensory modifiers (e.g. exfoliants), emollients, anti-acne actives, antimicrobial and antifungal actives, antiwrinkle and anti-skin atrophy actives, skin barrier repair actives, artificial tanning actives, skin lightening actives, sunscreen actives, anti-itch ingredients, fragrance, moisturizers (e.g. occlusive like petroleum jelly; or non-occlusive like glycerin) optical modifiers and mixtures thereof.

[0113] Cationic Skin Conditioning Agents

[0114] A useful component in compositions according to the invention is a cationic skin feel agent or polymer, such as for example cationic celluloses. Cationic polymers are preferably used at levels as low as about 0.1 to 2% up to levels as high as the solubility limit of the specific polymer, or preferably up to about 4 to 5% by wt., provided that the solubility limit of the particular cationic polymer or blend thereof is not exceeded. Cationic cellulose is available from Amerchol Corp. (Edison, N.J., USA) in their Polymer JR (trade mark) and LR (trade mark) series of polymers, as salts of hydroxyethyl io cellulose reacted with trimethyl ammonium substituted epoxide, referred to in the industry (CTFA) as Polyquaternium 10. Another type of cationic cellulose includes the polymeric quaternary ammonium salts of hydroxyethyl cellulose reacted with lauryl dimethyl ammonium-substituted epoxide, 15 referred to in the industry (CTFA) as Polyquaternium 24. These materials are available from Amerchol Corp. (Edison, N.J., USA) under the tradename Polymer LM-200.

[0115] Also, preferred cationic polymers are quaternary nitrogen-containing polysaccharides, preferably quaternary nitrogen-containing cellulose ethers, such as those described in U.S. Pat. Nos. 3,472,840; 3,962,418; 4,663,159, and U.S. Pat. No. 5,407,919. Particularly preferred are quaternary nitrogen-containing hydroxyethyl celluloses. Examples of such cationic polymers are salts of hydroxyethyl cellulose reacted with a trimethyl ammonium substituted epoxide such as Polyquaternium-10, made commercially available by Dow® as UCARE™ Polymer JR-125, UCARE Polymer JR-400, UCARE Polymer KF, UCARE Polymer J R-30M, UCARE Polymer LR- 400, UCARE Polymer LR-30M, UCARE Polymer LK mixtures thereof or the like.

[0116] Other preferred cationic polymers include those known as hydrophobically-modified cationic conditioning polymers such as those made commercially available also by Dow® under the names SoftCATTM SL 5, SoftCAT SL 30, SoftCAT SL 60, SoftCAT SL 100, SoftCAT SK-L, SoftCAT SK-M, and SoftCAT SK-H. Included for suitable use in the invention as thickening agent are those cationic polymers referred to as Polyquaternium-7, Polyquaternium-44, Polyquaternium 24 or mixtures thereof

[0117] A particularly suitable type of cationic polysaccharide polymer that can be used is a cationic guar gum derivative, such as guar hydroxypropyltrimonium chloride (Commercially available from Rhone-Poulenc in their JAGUAR trademark series). Examples are JAGUAR C13S, which has a low degree of substitution of the cationic groups and high viscosity, JAGUAR C15, having a moderate degree of substitution and a low viscosity, JAGUAR C17 (high degree of substitution, high viscosity), JAGUAR C16, which is a hydroxypropylated cationic guar derivative containing a low level of substituent groups as well as cationic quaternary ammonium groups, and JAGUAR 162 which is a high transparency, medium viscosity guar having a low degree of substitution. Particularly preferred cationic polymers are JAGUAR C13S, JAGUAR C15, JAGUAR C17 and JAGUAR C16 and JAGUAR C162, especially JAGUAR C13S, and JAGUAR C-14 / BFG. The JAGUAR C14 / BFG material is the same molecule as JAGUAR C13, except that a glyoxal cross linker has replaced the boron. Other cationic skin feel agents known in the art may be used provided that they are compatible with the inventive formulation.

[0118] Other suitable examples of surfactants described above which may be used are described in "Surface Active Agents and Detergents" (Vol. I & II) by Schwartz, Perry & Berch, incorporated into the subject application by reference in its entirety. In addition, the inventive cleansing composition of the invention may include 0 to 15% by wt. optional ingredients as follows: perfumes; sequestering agents, such as tetrasodium ethylenediaminetetraacetate (EDTA), EHDP or mixtures in an amount of 0.01 to 1%, preferably 0.01 to 0.05%; and soluble coloring agents, and the like; all of which are useful in so enhancing the appearance or cosmetic properties of the product. The compositions may further comprise antimicrobials such as 2-hydroxy-4,2',4' trichlorodiphenylether (DP300); preservatives such as dimethyloldimethylhydantoin (Glydant 55 XL1000), parabens, sorbic acid etc., and the like. The compositions may also comprise coconut acyl monoor 2.5 diethanol amides as suds boosters, and strongly ionizing salts such as sodium chloride and sodium sulfate may also be used to advantage. Preferably strongly ionizing salts, otherwise known as electrolytes, will be present at less than 3, 2 or 1 % by wt. Antioxidants such as, for example, butylated hydroxytoluene (BHT) and the like may be used advantageously in amounts of about 0.01 % or higher if appropriate.

[0119] The term "emollient" is defined as a substance which softens or improves the elasticity, appearance, and youthfulness of the skin (stratum corneum) by either increasing its water content, adding, or replacing lipids and other skin nutrients; or both, and keeps it soft by retarding the decrease of its water content. Moisturizers that also are Humectants such as polyhydric alcohols, e.g. glycerin and propylene glycol, and the like; and polyols such as the polyethylene glycols and the like may be used as hydrophilic emollients. Humectants are preferably used at levels as low as 1 , 3 or 5% by wt. and at levels as high as 6, 8 or 10% by wt.

[0120] Petrolatum is used in the invention, preferably at levels as low as 1 , 3 or 4% by wt. and at levels as high as 5, 6, 8, 12 or 16% by wt. Petrolatum is defined as a mixture of liquid hydrocarbons derived from petroleum having a melting point between 35 and 80 degrees C (as determined by ASTM D127-08, "Standard Test Method for Drop Melting Point of Petroleum Wax, including Petrolatum", ASTM International, West Conshohocken, Pa.) and a minimum viscosity of 10 Kps at 32 degrees C. Preferably it has a viscosity range of 10 to 35 Kps at 32 degrees C. More preferably the upper limit of viscosity is 25 or 50 Kps at 32 degrees C.

[0121] Other non- Petrolatum hydrophobic emollients are preferably present at total levels of less than about 1.5, 1.0, or 0.5% by wt. in the inventive composition and are more preferably absent from the composition. These hydrophobic emollients include but are not limited to the following:

[0122] (a) silicone oils and modifications thereof such as linear and cyclic polydimethylsiloxanes; amino, alkyl, alkylaryl, and aryl silicone oils; (b) fats and oils including natural fats and oils such as jojoba, soybean, sunflower, rice bran, avocado, almond, olive, sesame, persic, castor, coconut, mink oils; cacao fat; beef tallow, lard; hardened oils obtained by hydrogenating the aforementioned oils; and synthetic mono, di and triglycerides such as myristic acid glyceride and 2-ethylhexanoic acid glyceride;

[0123] (c) waxes such as carnauba, spermaceti, beeswax, lanolin, and derivatives thereof;

[0124] (d) hydrophobic and hydrophillic plant extracts;

[0125] (e) non- Petrolatum hydrocarbons such as polybutene, liquid paraffins, microcrystalline wax, ceresin, squalene, pristan and mineral oil;

[0126] (f) higher fatty acids such as lauric, myristic, palmitic, stearic, behenic, oleic, linoleic, linolenic, lanolic, isostearic, arachidonic and poly unsaturated fatty acids (PLIFA);

[0127] (g) higher alcohols such as lauryl, cetyl, stearyl, oleyl, behenyl, cholesterol and 2- hexydecanol alcohol;

[0128] (h) esters such as cetyl octanoate, myristyl lactate, cetyl lactate, isopropyl myristate, myristyl myristate, isopropyl palmitate, isopropyl adipate, butyl stearate, decyl oleate, cholesterol isostearate, glycerol monostearate, glycerol distearate, glycerol tristearate, alkyl lactate, alkyl citrate and alkyl tartrate;

[0129] (i) essential oils and extracts thereof such as mentha, jasmine, camphor, white cedar, bitter orange peel, ryu, turpentine, cinnamon, bergamot, citrus unshiu, calamus, pine, lavender, bay, clove, hiba, eucalyptus, lemon, starflower, thyme, peppermint, rose, sage, sesame, ginger, basil, juniper, lemon grass, rosemary, rosewood, avocado, grape, grapeseed, myrrh, cucumber, watercress, calendula, elder flower, geranium, linden blossom, amaranth, seaweed, ginko, ginseng, carrot, guarana, tea tree, jojoba, comfrey, oatmeal, cocoa, neroli, vanilla, green tea, penny royal, aloe vera, menthol, cineole, eugenol, citral, Citronelle, borneol, linalool, geraniol, evening primrose, camphor, thymol, spirantol, penene, limonene and terpenoid oils;

[0130] (j) mixtures of any of the foregoing components, and the like.

[0131] Isotropic Micellar Phase Compositions

[0132] The inventive cleansing composition possesses isotropic micellar phase microstructure. The rheological behavior of all surfactant solutions, including liquid cleansing solutions, is strongly dependent on the microstructure, i.e., the shape and concentration of micelles or other selfassembled structures in solution.

[0133] When there is sufficient surfactant to form micelles (concentrations above the critical micelle concentration or CMC), for example, spherical, cylindrical (rod-like or discoidal), spherocylindrical, or ellipsoidal micelles may form. As surfactant concentration increases, ordered liquid crystalline phases such as lamellar phase, hexagonal phase, cubic phase or L3 sponge phase may form. The non-isotropic hexagonal phase, consists of long cylindrical micelles arranged in a hexagonal lattice. In general, the microstructure of most personal care products consist of either an isotropic dispersion including spherical micelles; and rod micelles; or an ordered liquid crystalline phase such as a lamellar dispersion. As noted above, micelles may be spherical or rod-like. Formulations having spherical micelles tend to have a low viscosity and exhibit Newtonian shear behavior (i.e. , viscosity stays constant as a function of shear rate; thus, if easy pouring of product is desired, the solution is less viscous. In these systems, the viscosity increases linearly with surfactant concentration. Rod micellar solutions are more viscous because movement of the longer micelles is restricted. At a critical shear rate, the micelles align and the solution becomes shear thinning. Addition of salts increases the size of the rod micelles thereof increasing zero shear viscosity (i.e., viscosity when sitting in bottle) which helps suspend particles but also increases critical shear rate (point at which product becomes shear thinning; higher critical shear rates means that the product is more difficult to pour).

[0134] One way of characterizing isotropic micellar dispersions (hereinafter "isotropic compositions") include cone and plate viscosity measurement as described below.

[0135] Water soluble or dispersible polymeric dispersion agents are included in the inventive composition. Suitable agents include carbohydrate gums such as cellulose gum, microcrystalline cellulose, cellulose gel, hydroxyethyl cellulose, hydroxypropyl cellulose, sodium carboxymethylcellulose, hydroxymethyl carboxymethyl cellulose, carrageenan, hydroxymethyl carboxypropyl cellulose, methyl cellulose, ethyl cellulose, guar gum, gum karaya, gum tragacanth, gum arabic, gum acacia, gum agar, xanthan gum and mixtures thereof.

[0136] Preferred carbohydrate gums are Hydroxypropyl Methocellulose such as Methocel® 40-100 and Methocel 40-202 (Dow Chemicals, Midland, Mich.), Sodium Hydroxypropyl starch phosphate such as Pure-Gel B990 (Grain Processing Corp., Muscatine, Iowa), and Xanthan Gum such as Keltrol CG (CPKelco, Atlanta, Ga.).

[0137] Suitable polymeric dispersion agents also include acrylate containing homo and copolymers such as the crosslinked poly acrylates available 2.5 under the CARBOPOL trade name, the hydrophobically modified cross linked polyacrylates available under the AQUA trade name, and the PEMULEN trade name (all sold by Lubrizol Company, Wickliffe, Ohio) and the alkali swellable acrylic latex polymers sold by Rohm and Haas (Philadelphia, Pa.) under the ARYSOL or ACLILYN trade names Preferred acrylates are the Aqua SF-1® and Carbopol llltrez 21® polymers.

[0138] Clay and Silica Structuring Agents

[0139] Clay, silica and other particle based comparative structuring agent(s) may be present at less than 1.5, 1 or 0.5% by wt. and preferably are not present in the inventive composition. These agents include but are not limited to dispersed amorphous silica selected from the group consisting of fumed silica and precipitated silica and mixtures thereof. As used herein the term "dispersed amorphous silica" refers to small, finely divided non-crystalline silica having a mean agglomerate particle size of less than about 100 microns.

[0140] Other examples of comparative structurants include but are not limited to dispersed smectite clay including bentonite and hectorite and mixtures thereof. Bentonite is a colloidal aluminum clay sulfate. Hectorite is a clay containing sodium, magnesium, lithium, silicon, oxygen, hydrogen and fluorine.

[0141] Optional Active Agents

[0142] Advantageously, active agents other than conditioning agents such as emollients or moisturizers defined above may be added to the cleansing composition in a safe and effective amount during formulation to treat the skin during the use of the product provided that they do not exceed solubility limits whereby the reflectance increases beyond 80% in the cleansing composition. Suitable active ingredients include those that are soluble in the aqueous phase, in the Petrolatum phase or in both phases. Suitable active agents may be advantageously selected from antimicrobial and antifungal actives, vitamins, anti-acne actives; anti-wrinkle, anti-skin atrophy and skin repair actives; skin barrier repair actives; non-steroidal cosmetic soothing actives; artificial tanning agents and accelerators; skin lightening actives; sunscreen actives; sebum stimulators; sebum inhibitors; anti-oxidants; protease inhibitors; skin tightening agents; anti-itch ingredients; hair growth inhibitors; 5-alpha reductase inhibitors; desquamating enzyme enhancers; anti-glycation agents; topical anesthetics, or mixtures thereof; and the like. These active agents may be selected from water soluble active agents, oil soluble active agents, pharmaceutically acceptable salts and mixtures thereof.

[0143] Also useful in the compositions of the invention are ingredients selected from organic solvents (ethanol), other thickeners, sequestrants (EDTA), coloring agents, opacifiers, pearlisers (zinc stearate, TiCh), preservatives (for example Glydant, parabens), antioxidants (BHT) and mixtures thereof).

[0144] The term "active agent" as used herein, means personal care actives which can be used to deliver a benefit to the skin and / or hair and which generally are not used to confer a conditioning benefit, as is conferred by humectants and emollients previously described herein. The term "safe and effective amount" as used herein, means an amount of active agent high enough to modify the condition to be treated or to deliver the desired skin care benefit, but low enough to avoid serious side effects. The term "benefit," as used herein, means the therapeutic, prophylactic, and / or chronic benefits associated with treating a particular condition with one or more of the active agents described herein. What is a safe and effective amount of the active agent ingredient will vary with the specific active agent, the ability of the active to penetrate through the skin, the age, health condition, and skin condition of the user, and other like factors.

[0145] Preferably the composition of the present invention comprise from about 0.01 % to about 50%, more preferably from about 0.05% to about 25%, even more preferably 0.1% to about 10%, and most preferably 0.1% % to about 5%, by weight of the active agent component.

[0146] Anti-acne actives can be effective in treating acne vulgaris, a chronic disorder of the pilosebaceous follicles. Nonlimiting examples of useful anti-acne actives include the keratolytics such as salicylic acid (o-hydroxybenzoic acid), derivatives of salicylic acid such as 5-octanoyl salicylic acid and 4 methoxysalicylic acid, and resorcinol; retinoids such as retinoic acid and its derivatives (e.g., cis and trans); sulfur-containing D and L amino acids and their derivatives and salts, particularly their N-acetyl derivatives, mixtures thereof and the like.

[0147] Antimicrobial and antifungal actives can be effective to prevent the proliferation and growth of bacteria and fungi. Nonlimiting examples of antimicrobial and antifungal actives include b-lactam drugs, quinolone drugs, ciprofloxacin, norfloxacin, tetracycline, erythromycin, amikacin, 2,4,4'- trichloro-2'-hydroxy diphenyl ether, 3,4,4 -trichlorobanilide, phenoxyethanol, triclosan; triclocarban; and mixtures thereof and the like. Anti-wrinkle, anti-skin atrophy and skin repair actives can be effective in replenishing or rejuvenating the epidermal layer. These actives generally provide these desirable skin care benefits by promoting or maintaining the natural process of desquamation. Nonlimiting examples of antiwrinkle and anti-skin atrophy actives include vitamins, minerals, and skin nutrients such as milk, vitamins A, E, and K; vitamin alkyl esters, including vitamin C alkyl esters; magnesium, calcium, copper, zinc and other metallic components; retinoic acid and its derivatives (e.g., cis and trans); retinal; retinol; retinyl esters such as retinyl acetate, retinyl palmitate, and retinyl propionate; vitamin B3 compounds (such as niacinamide and nicotinic acid), alpha hydroxy acids, beta hydroxy acids, e.g. salicylic acid and derivatives thereof (such as 5- octanoyl salicylic acid, heptyloxy 4 salicylic acid, and 4-methoxy salicylic acid); mixtures thereof and the like.

[0148] Skin barrier repair actives are those skin care actives which can help repair and replenish the natural moisture barrier function of the epidermis. Nonlimiting examples of skin barrier repair actives include lipids such as cholesterol, ceramides, sucrose esters and pseudo-ceramides as described in European Patent Specification No. 556,957; ascorbic acid; biotin; biotin esters; phospholipids, mixtures thereof, and the like. Non-steroidal cosmetic soothing actives can be effective in preventing or treating inflammation of the skin. The soothing active enhances the skin appearance benefits of the present invention, e.g., such agents contribute to a more uniform and acceptable skin tone or color. Nonlimiting examples of cosmetic soothing agents include the following categories: propionic acid derivatives; acetic acid derivatives; fenamic acid derivatives; mixtures thereof and the like. Many of these cosmetic soothing actives are described in U.S. Pat. No. 4,985,459 to Sunshine et al., issued Jan. 15, 1991 , incorporated by reference herein in its entirety.

[0149] In another embodiment of the invention, the composition comprises 12 hydroxystearic acid.

[0150] Artificial tanning actives can help in simulating a natural suntan by increasing melanin in the skin or by producing the appearance of increased melanin in the skin. Nonlimiting examples of artificial tanning agents and accelerators include dihydroxyacetone; tyrosine; tyrosine esters such as ethyl tyrosinate and glucose tyrosinate; mixtures thereof, and the like.

[0151] Skin lightening actives can actually decrease the amount of melanin in the skin or provide such an effect by other mechanisms. Nonlimiting examples of skin lightening actives useful herein include aloe extract, alpha-glyceryl-L-ascorbic acid, aminotyroxine, ammonium lactate, glycolic acid, hydroquinone, 4 hydroxyanisole, mixtures thereof, and the like.

[0152] Also useful herein are sunscreen actives. A wide variety of sunscreen agents are described in U.S. Pat. No. 5,087,445, to Haffey et al., issued Feb. 11 , 1992; U.S. Pat. No. 5,073,372, to Turner et al., issued 2.5 Dec. 17, 1991 ; U.S. Pat. No. 5,073, 371 , to Turner et al. issued Dec. 17, 1991 ; and Segarin, et al., at Chapter VIII, pages 189 et seq., of Cosmetics Science and Technology, all of which are incorporated herein by reference in their entirety.

[0153] Nonlimiting examples of sunscreens which are useful in the compositions of the present invention are those selected from the group consisting of octyl methoxyl cinnamate (Parsol MCX) and butyl methoxy benzoylmethane (Parsol 1789), 2-ethylhexyl p-methoxycinnamate, 2-ethylhexyl N,N- dimethyl-p-aminobenzoate, p-aminobenzoic acid, 2-phenylbenzimidazole-5-sulfonic acid, oxybenzone, mixtures thereof, and the like. Sebum stimulators can increase the production of sebum by the sebaceous glands. Nonlimiting examples of sebum stimulating actives include bryonolic acid, dehydroetiandro sterone (DHEA), orizanol, mixtures thereof, and the like.

[0154] Sebum inhibitors can decrease the production of sebum by the sebaceous glands. Nonlimiting examples of useful sebum inhibiting actives include aluminum hydroxy chloride, corticosteroids, dehydroacetic acid and its salts, dichlorophenyl imidazoldioxolan (available from Elubiol), mixtures thereof, and the like.

[0155] Also useful as actives in the present invention are protease inhibitors. Protease inhibitors can be divided into two general classes: the proteinases and the peptidases. Proteinases act on specific interior peptide bonds of proteins and peptidases act on peptide bonds adjacent to a free amino or carboxyl group on the end of a protein and thus cleave the protein from the outside. The protease inhibitors suitable for use in the present invention include, but are not limited to, proteinases such as serine proteases, metalloproteases, cysteine proteases, and aspartyl protease, and peptidases, such as carboxypepidases, dipeptidases and aminopepidases, mixtures thereof and the like.

[0156] Other useful as active ingredients in the present invention are skin tightening agents. Nonlimiting examples of skin tightening agents which are useful in the compositions of the present invention include monomers which can bind a polymer to the skin such as terpolymers of vinylpyrrolidone, (meth)acrylic acid and a hydrophobic monomer comprised of long chain alkyl (meth)acrylates, mixtures thereof, and the like. Active ingredients in the present invention may also so include antiitch ingredients. Suitable examples of anti-itch ingredients which are useful in the compositions of the present invention include hydrocortisone, methdilizine and trimeprazineare, mixtures thereof, and the like. Nonlimiting examples of hair growth inhibitors which are useful in the compositions of the present invention include beta estradiol, anti angiogenic steroids, curcuma extract, cycloxygenase inhibitors, evening primrose oil, linoleic acid and the like. Suitable 5-alpha reductase inhibitors such as ethynylestradiol and genistine mixtures thereof, and the like.

[0157] Nonlimiting examples of desquamating enzyme enhancers which are useful in the compositions of the present invention include alanine, aspartic acid, N methyl serine, serine, trimethyl glycine, mixtures thereof, and the like.

[0158] A nonlimiting example of an anti-glycation agent which is useful in the compositions of the present invention would be Amadorine (available from Barnet Products Distributor), and the like.

[0159] The compositions of the present invention preferably include a pearlescer to improve visual appearance and / or consumer appeal of the product. Most preferably the pearlescer is selected from mica, titanium dioxide, titanium dioxide coated mica ethylene glycol distearate (INCI glycol distearate) and mixtures thereof.

[0160] Unless otherwise indicated, ratios, percentages, parts, and the like, referred to herein, are by weight.

[0161] Except where otherwise explicitly indicated, all numbers in this description indicating amounts of material or conditions of reaction, physical properties of materials and / or use are to be understood as modified by the word “about.” All amounts are by weight of the final composition, unless otherwise specified.

[0162] It should be noted that in specifying any range of concentration or amount, any particular upper concentration can be associated with any particular lower concentration or amount as well as any subranges consumed therein. In that regard, it is noted that all ranges disclosed herein are inclusive of the endpoints, and the endpoints are independently combinable with each other (e.g., ranges of “up to 25% by weight, or, more specifically, 5% by weight to 20% by weight, in inclusive of the endpoints and all intermediate values of the ranges of 5% by weight to 25% by weight, etc.). “Combination is inclusive of blends, mixtures, alloys, reaction products, and the like. Furthermore, the terms “first”, “second”, and the like herein do not denote any order, quantity, or importance, but rather are used to distinguish one element from another. The terms “a” and “an” and “the” herein do not denote a limitation of quantity and are to be construed to cover both the singular and the plural, unless otherwise indicated herein or clearly contradicted by context. The suffix “(s)” as used herein is intended to include both the singular and the plural of the term it modifies, thereby including one or more of the term (e.g., the film(s) includes one or more films). Reference throughout the specification to “one embodiment”, “one aspect”, “another embodiment”, “another aspect”, “an embodiment”, “an aspect” and so forth means that a particular element (e.g., feature, structure, and / or characteristic) described in connection with the embodiment or aspect is included in at least one embodiment or aspect described herein and may or may not be present in other embodiments or aspects. In addition, it is to be understood that the described elements may be combined in any suitable manner in the various embodiments or aspects.

[0163] All cited patents, patent applications, and other references are incorporated herein by reference in their entirety. However, if a term in the present application contradicts or conflicts with a term in the incorporated reference, the term from the present application takes precedence over the conflicting term from the incorporated reference. While particular aspects have been described, alternatives, modifications, variations, improvements, and substantial equivalents that are or may be presently unforeseen may arise to applicants or others skilled in the art. Accordingly, the appended claims as filed and as they may be amended are intended to embrace all such alternatives, modifications, variations, improvements, and substantial equivalents.

[0164] For the avoidance of doubt the word “comprising” is intended to mean “including” but not necessarily “consisting of” or “composed of.” In other words, the listed steps, options, or alternatives need not be exhaustive.

[0165] The disclosure of the invention as found herein is to be considered to cover all aspects as found in the claims as being multiply dependent upon each other irrespective of the fact that claims may be found without multiple dependency or redundancy. Unless otherwise specified, numerical ranges expressed in the format "from x to y" are understood to include x and y. In specifying any range of values or amounts, any particular upper value or amount can be associated with any particular lower value or amount. All percentages and ratios contained herein are calculated by weight unless otherwise indicated. The various features of the present invention referred to in individual sections above apply, as appropriate, to other sections mutatis mutandis. Consequently, features specified in one section may be combined with features specified in other sections as appropriate. Any section headings are added for convenience only and are not intended to limit the disclosure in any way. Examples

[0166] The following examples are merely illustrative of the compositions disclosed herein and are not intended to limit the scope hereof.

[0167] The shampoo compositions in the following examples were prepared using a standard shampoo preparation procedure.

[0168] In these examples, the “furan sulfonate” was made according to the method given herein above, under the heading “Method of making furan-based sulphate free anionic surfactant”. The resulting furan sulfonate material had a 2:1 blend of C12 and C14 tails.

[0169] The following acronyms were used:

[0170] SMLT = sodium methyl lauroyl taurate

[0171] SLI = sodium lauroyl isethionate

[0172] CAPB = cocam idopropyl betaine

[0173] SLES = sodium lauryl ether sulphate

[0174] AOS = alpha olefin sulphonate

[0175] LHS = lauryl hydroxysultaine

[0176] Example 1 : Comparative Compositions 1 - 6

[0177] The comparative shampoo compositions in Table 1 were prepared.

[0178] Table 1 : Compositions, viscosity, clarity and stability of Comparative Examples 1 - 6 Examples in Table 1 illustrate that compositions made outwith the present invention using typical surfactants of the prior art have associated disadvantages, namely the compositions are unstable and / or non-transparent and / or have poor viscosity. Whilst composition 1 appears to have acceptable properties, it is made with the sulphate containing surfactant, sodium lauryl ether sulphate. Example 2, which utilises an alpha olefin sulphonate (AOS) surfactant also appears to perform well, but it is petrochemically derived and therefore disadvantageous.

[0179] Example 2: Inventive Compositions 7 - 17

[0180] The inventive compositions in Table 2 were prepared using the inventive furan sulfonate.

[0181] Table 2 - Compositions, viscosity and clarity of Inventive Examples 7 - 17

[0182] * comprising a 2:1 blend of C12 and C14 tails

[0183] Compositions in Table 2 demonstrate that the inventive furan-based anionic sulphate free surfactants can be formulated across a wide range of anionic / amphoteric ratios providing clear formulations and with acceptable viscosity. Example 3: Inventive Compositions 18 - 25

[0184] The inventive compositions in Table 3 were prepared using the inventive furan sulphonate.

[0185] These compositions each comprised 6% total surfactant and were free from added salt.

[0186] Table 3 - Compositions and viscosties of Inventive Examples 18 - 25

[0187] *Qualitative viscosity was assessed against a 1-5 scale defined below:

[0188] 1 - water thin

[0189] 2 - Some thickening but very runny 3 - Acceptable viscosity

[0190] 4 - Very viscous solution: tipped upside down and eventually flows down slowly

[0191] 5 - Non-flowing gel: tipped upside down and no movement noted at all Example 4: Inventive Compositions 26 - 33

[0192] The inventive compositions in Table 4 were prepared with 6 % total furan sulphonate surfactant of the invention, and added salt.

[0193] Table 4: Compositions and viscosities of Inventive Examples 26 - 33

[0194] Example 5: Foaming properties of Compositions 7, 10 & 13 in accordance with the invention and Comparative Benchmark Compositions 1 & 2

[0195] In this example, the aim is for the inventive compositions 7, 10 & 13 to reach the level of foaming achieved by the two benchmark compositions, namely a standard sulphate based cleanser (1) and a petrol-derived sulphonate based cleanser (2).

[0196] The foaming properties of these compositions were determined using the following test methodology:

[0197] Lather was evaluated according to the following protocol: A Sita Foam Tester R-2000 was used. Measurement Parameters were employed as follows: mixing speed 1000 rpm; measurement time (single timepoint) 45 Seconds; dilution: 250 mL; sample size 10 g.

[0198] The following procedure was carried out:

[0199] 1) A cleaning cycle was run using hot tap water, to clean and equilibrate the vessel.

[0200] 2) The water reservoir was filled with 38°C tap water. The water temperature in the vessel was maintained at 38°C + / - 0.5°C for each measurement .

[0201] 3) 10.0 g of product to be tested was weighed in a 10 ml syringe .

[0202] 4) The product to be tested was injected into bottom of main vessel. 5) The measurement was then run to determine the volume of foam produced by each composition.

[0203] The results were recorded in Table 5 below.

[0204] Table 5 - Foam volume results using SITA foam tester for Inventive Compositions 7, 10 & 13 and Comparative Benchmarks 1 & 2

[0205] Samples 8,11,13 made according to this invention were found to have foam comparable to a standard sulfate based cleanser (composition 1) or a petrol-derived sulphonate based cleanser composition 2, when evaluated using the SITA foam method as described above.

[0206] Example 6: viscosity stability of Composition A comprising a Furan Sulfonate Surfactant with an amide linker, in accordance with the present invention, and Comparative Composition B comprising a Furan Sulfonate Surfactant with an ester linker, as disclosed in WQ2020229158.

[0207] Two samples were prepared to illustrate the difference between an ester based furan-sulfonate surfactant of the prior art and the amide based furan-sulfonate surfactant of the present invention.

[0208] The different furan-sulphonate surfactants were each made in accordance with the procedures given in the present document, and WO2020229158 respectively.

[0209] Preparation of Composition A and Composition B

[0210] The compositions were prepared by weighing all materials into a test tube.

[0211] The CAPB and water were pre-mixed with pH adjusted to 9 before addition of the furan sulphonate surfactants.

[0212] The compositions were then heated to 70 degrees C followed by vortex mixing until fully dissolved. The compositions were then allowed to cool to room temperature.

[0213] Stability testing

[0214] The samples were then put into 4 degrees C oven overnight.

[0215] The samples were then removed and allowed to sit and equilibrate to room temperature for a few hours.

[0216] Results

[0217] Composition A, made with Furan Sulfonate surfactant of the present invention, formed a clear viscous non-flowable gel. On the other hand, Composition B, made using the prior art Furan surfactant was unstable and formed a water-thin liquid.

Claims

Claims1. A furan-based anionic sulphate free surfactant comprising: a) a head group comprising i) a furan ring ii) a sulphonate group directly attached to the furan ring; b) an amide containing linker group; and c) a hydrophobic alkyl tail group having a carbon chain length of 8 to 18; wherein the furan-based anionic sulphate free surfactant has the structure of Formula(I):Formula (I) where R is a hydrophobic alkyl tail group having a carbon chain length of 8 to 18, 18:1 and 18:2 where R groups of different chain lengths can be used in combination as a blend, preferably a blend of chain lengths of C12 and C14; and where X is a counterion, selected from organic and inorganic counterions.

2. A furan-based anionic sulphate free surfactant as claimed in claim 1, wherein the amide linker group comprises an amide and a saturated hydrocarbon chain.

3. A furan-based anionic sulphate free surfactant as claimed in claim 2, wherein the saturated hydrocarbon chain is a methylene group.

4. A furan-based anionic sulphate free surfactant as claimed in any preceding claim, wherein the hydrophobic alkyl tail is an alkyl chain comprising a carbon chain length of 8 to 18, preferably from 8 to 16 carbon chains, most preferably from 10 to 14.

5. A furan-based anionic sulphate free surfactant as claimed in claim 4, wherein the alkyl chain is linear.

6. A furan-based anionic sulphate free surfactant as claimed in claim 4 or claim 5, wherein the alkyl chain is saturated.

7. An isotropic micellar phase cleansing composition comprising a) the furan-based anionic sulphate free surfactant defined in any of claims 1 to 7; b) a co-surfactant selected from a zwitterionic surfactant, an amphoteric surfactant and mixtures thereof; and c) water; wherein the composition has a viscosity in the range of from 1 ,000 to 50,000 mPa.s, preferably from 1,000 to 25,000, more preferably from 2,000 to 25,000 mPa.s, even more preferably from 2,100 to 15,000 mPa.s, when measured at 25 degrees C and 4s-7, using sandblasted 40mm parallel plates, on a Wingspan rheometer (TA instruments).

8. An isotropic micellar phase cleansing composition as claimed in claim 7, which comprises an inorganic electrolyte.

9. An isotropic micellar phase cleansing composition as claimed in claim 7 or claim 8, wherein the amount of furan-based anionic sulphate free surfactant is from 0.5 to 20 wt %, preferably from 1 to 15 wt %, more preferably from 2 to 10, even more preferably from 3 to 8 wt %, by weight of total composition.

10. A cleansing composition as claimed in any one of claims 7 to 9, wherein the total amount of furan-based anionic sulphate free surfactant and co-surfactant is from 0.5 to 25 wt %, preferably from 1 to 20 wt %, by weight of total composition.

11. An isotropic micellar phase cleansing composition as claimed in any one of claims 7 to 10, wherein the weight ratio of furan-based anionic sulphate free surfactant to cosurfactant is in the range of from 8:2 to 2:8, preferably from 7:3 to 3:7.

12. An isotropic micellar phase cleansing composition as claimed in claim 11 , wherein the zwitterionic surfactant or amphoteric surfactant is selected from alkyl betaines, alkylamidopropyl betaines, alkyl hydroxysultaines, alkyl amidopropyl hydroxy sultaines, and mixtures thereof.

13. An isotropic micellar phase cleansing composition as claimed in any one of claims 7 to 12 which is transparent, such that the composition has a turbidity of lower than 1 cm-1, preferably lower than 0.5 cm-1, more preferably lower than 0.4 cm-1, even more preferably lower than 0.25 cm-1most preferably lower than 0.1 cm-1, as measured using a UV / visible spectrophotometer and applying the equation turbidity = (2.3*A / L), where A is the absorbance measured from the sample at 750 nm and L is the path length.

14. A method of cleaning a surface comprising applying to the surface an isotropic micellar phase cleansing composition as defined in any one of claims 7 to 13.

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