WO2009083736A1 - Compositions and uses thereof - Google Patents

Compositions and uses thereof Download PDF

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Publication number
WO2009083736A1
WO2009083736A1 PCT/GB2008/051228 GB2008051228W WO2009083736A1 WO 2009083736 A1 WO2009083736 A1 WO 2009083736A1 GB 2008051228 W GB2008051228 W GB 2008051228W WO 2009083736 A1 WO2009083736 A1 WO 2009083736A1
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WO
WIPO (PCT)
Prior art keywords
composition
ester
esters
optionally substituted
aromatic acid
Prior art date
Application number
PCT/GB2008/051228
Other languages
French (fr)
Inventor
Samad Syed
Phillip Cotrell
Original Assignee
Innospec Limited
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Publication date
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Publication of WO2009083736A1 publication Critical patent/WO2009083736A1/en

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Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37Esters of carboxylic acids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q15/00Anti-perspirants or body deodorants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • A61Q19/007Preparations for dry skin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • A61Q19/10Washing or bathing preparations
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/02Preparations for cleaning the hair
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/12Preparations containing hair conditioners
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/20Organic compounds containing oxygen
    • C11D3/2093Esters; Carbonates

Definitions

  • This invention relates to aromatic esters (for example benzoate esters) of C12 and Ci 4 fatty alcohols, to their use in cosmetic compositions, and to additive compositions containing them in admixture.
  • aromatic esters for example benzoate esters
  • esters composed mainly or essentially of components within the mixtures described in US 4,275,222, when added to a cosmetic composition, particularly a sunscreen composition, provide new and beneficial properties.
  • an additive composition for enhancing a cosmetic composition comprising in admixture (a) an ester of an optionally substituted aromatic acid and a C12 primary alcohol and (b) an ester of an optionally substituted aromatic acid and a Ci 4 primary alcohol, wherein compounds (a) and (b) together provide at least 60% by weight, of the additive composition .
  • a preferred ester (a) is an ester of an optionally substituted benzoic acid and a branched C12 primary alcohol .
  • a preferred ester (b) is an ester of an optionally substituted benzoic acid and a branched Ci 4 primary alcohol .
  • Q is a substituent, as later defined; m is 0 (zero) or an integer from 1 to 5 (the groups Q being the same as or different from each other when m is 2, 3, 4 or 5) ; and where R is a Ci 2 alkyl group in compound (a) , or a C i4 alkyl group in compound (b) .
  • the benzene ring (or other aromatic ring system) of ester (a) or (b) may be substituted with 0 to 5 groups (in addition to the reacted acid group COOH) .
  • it may be tri- or di-substituted in the ring (or ring system) or, more preferably, mono-substituted. Substitution may be at the ortho, and/or meta, and/or para position(s).
  • the benzene ring (or other aromatic ring) of ester (a) may be substituted and the benzene ring (or other aromatic ring system) of ester (b) may be unsubstituted; or the benzene ring (or other aromatic ring system) of ester (b) may be substituted and the benzene ring (or other aromatic ring system) of ester (a) may be unsubstituted; or both may be substituted, differently or the same; or, most preferably, both may be unsubstituted.
  • the or each substituent of the benzene ring (or other aromatic ring system) of ester (a) or (b) may be any common group used for substitution of a benzene ring (or other aromatic ring system) , for example one or more of an alkyl group (an especially preferred substituent), an alkenyl group, a haloalkyl group, an alkynyl group, a nitrile group, a carboxylic acid (in addition to the reacted carboxylic acid group) , an ester, an ether, an alkoxy group, a haloalkoxy group, a halo group, a hydroxyl group, a mercapto group, an alkylmercapto group, an alkylsulfoxy group, a sulfoxy group, an aryl group, an arylalkyl group, a substituted or unsubstituted amine group or a nitro group.
  • an alkyl group an especially preferred substituent
  • an alkyl group including of the alkyl moiety of an alkyl- containing group (for example alkoxy or haloalkyl) is suitably a Ci_ 4 alkyl group, more preferably a methyl group.
  • a Ci_ 4 alkyl group more preferably a methyl group.
  • each ester (a) and (b) may be branched at one or more positions of the backbone of the primary alcohol. Preferably, however, each backbone is linear.
  • the primary alcohol backbone of each ester (a) and (b) may be unsaturated or it may be saturated.
  • esters (a) and (b) of the first aspect of the invention together provide at least 70% by weight of the additive composition, more preferably at least 80%, more preferably at least 90%, more preferably at least 95%. Most preferably they provide at least 98% by weight of the additive composition.
  • the additive composition consists essentially of the esters (a) and (b) .
  • the ratio by weight of ester (a) to ester (b) is at least 1:1.
  • ester (a) is present in weight excess, over ester (b) .
  • the ratio by weight of ester (a) to ester (b) is at least 1.5:1, most preferably at least 2:1.
  • the ratio by weight of ester (a) to ester (b) is up to 5:1, more preferably up to 4:1, and most preferably up to 3:1.
  • An especially preferred ratio is 2 to 2.75 parts by weight of ester (a) to 1 part by weight of ester (b) .
  • the additive composition of the invention can produce enhanced properties when added to cosmetic compositions. These enhanced properties make such additive compositions beneficial for use in cosmetic products such as skin care, topical and personal care products. These products may be in the form of a cream, lotion, bar or stick.
  • the additive compositions of the invention have new and unexpected properties as cosmetic additives not only as an emollient but also as solvents and liquid carriers for a cosmetically active material in the cosmetic preparation.
  • the ester mixture of the first aspect or used in the second aspect may be made, separately or together, by analogous esterification reactions to those used for the preparation of other fatty alcohol-aromatic acid esters.
  • a composition for application to the person comprising (a) an ester of an optionally substituted aromatic acid and a Ci 2 primary alcohol and (b) an ester of an optionally substituted aromatic acid and a Ci 4 primary alcohol.
  • Said composition may also be called herein a cosmetic composition or a topical composition or a skin benefit composition.
  • a cosmetic composition of the second aspect has ester (a) to ester (b) present in a weight ratio which is as defined above for the additive composition of the first aspect.
  • the esters (a) and (b) may have been introduced separately into the cosmetic composition.
  • esters (a) and (b) in the form of an additive composition of the first aspect may be introduced to other ingredients to form a composition of the second aspect, but the invention as defined in the second aspect is not limited in that way.
  • compositions of the second aspect of the invention may comprise a carrier or diluent or solvent; and/or a cosmetically effective ingredient. Such further components may be as hereinafter described.
  • esters (a) and (b) of a composition of the second aspect of the invention constitute at least 40 %wt, preferably at least 50 %wt, more preferably at least 70 %wt, most preferably at least 90 %wt, of the total weight of C12-C15 fatty alcohol-aromatic acid (ester) content in the cosmetic composition.
  • the cosmetic composition is substantially free of C12-C15 fatty alcohol- aromatic acid esters apart from compounds (a) and (b) .
  • Esters (a) and (b) of a composition of the second aspect of the invention may suitably constitute at least 40 %wt, preferably at least 50 %wt, more preferably at least 70 %wt, most preferably at least 90 %wt, of the total weight of all esters of fatty alcohols and acids in the composition. Most preferably the composition is substantially free of all esters of fatty alcohols and acids apart from the esters (a) and (b) .
  • the ester mixture of the first aspect may impart valuable properties to the composition of the second aspect.
  • the esters (a) and (b) in admixture are substantially non- greasy, show lack of oiliness and greasiness, have very low cloud point and pour point, have a bland odor, low toxicity and are stable.
  • the esters (a) and (b) in admixture have good tactile properties, spreadability, solubility in/with sunscreen agents, low tackiness (stickiness), low greasiness on the skin, good suspension properties (e.g. TiC>2) and are effective in wetting and dispersing pigments.
  • the esters (a) and (b) have properties in addition to those mentioned hereinbefore when used as an emollient in a sunscreen agent.
  • SPDF sun protection factor
  • sunscreen agents of a lower sun protecting factor can be utilized in sunscreen compositions containing the esters (a) and (b) achieve the sunscreen protecting factors of higher protecting sunscreen agents.
  • esters (a) and (b) should be added to a composition when it is substantially pure and substantially free of other esters of aromatic acids and fatty alcohols. In this manner, it is believed that best results are achieved. However, this should not preclude the use of other fatty acid esters or fatty acids in these compositions, suitably within the percentage limits mentioned above, since the use of the esters (a) and (b) may still provide enhanced results to cosmetic compositions in which they are incorporated.
  • the esters (a) and (b) may be incorporated into cosmetic compositions as an emollient in order to impart to these compositions the aforementioned beneficial properties of this invention.
  • the esters (a) and (b) whether added individually or together in the form of an additive composition of the first aspect, can be used as an ingredient for any topical or cosmetic compositions including skin, nail, lip, hair topical compositions not only as an emollient but as a diluent, solvent and liquid carrier.
  • the esters (a) and (b) function as an effective solubilizer for the cosmetically active agents used in these cosmetic compositions.
  • the esters (a) and (b) are suitably incorporated in a cosmetic composition in an emollient effective amount.
  • the esters (a) and (b) are provided in an amount at least sufficient to provide the emollient properties to the cosmetic composition.
  • Emollients are dermatologically acceptable compositions that tend to lubricate the skin, increase the softness and suppleness of the skin, prevent or relieve dryness of the skin and/or protect the skin.
  • These emollients are typically water emissible, oily or waxy materials and in order to provide the improved results of this invention, the esters (a) and (b) are employed in any amount sufficient to impart, or improve to any degree, emolliency to the cosmetic composition.
  • the amount of the esters (a) and (b) in these cosmetic compositions depends on the type and quantity of other ingredients used and in the amount and type of functional additives that are utilized. Generally the amount of the esters (a) and (b) that are incorporated into these cosmetic compositions ranges from about 0.1% to about 30% by weight, for example about 0.3% to about 20% by weight, based upon the total weight of the cosmetic composition, with amounts from about 5% to about 15% by weight based upon the total weight of the cosmetic composition being especially preferred.
  • a third aspect of the present invention there is provided a method of preparing a cosmetic composition, wherein the esters (a) and (b) , separately or together in an additive composition of the first aspect, are mixed with other ingredient so as to produce a composition of the second aspect of this invention.
  • esters (a) and (b) can be utilized to produce the beneficial properties set forth above in any conventional topical cosmetic composition such sunscreen creams, hair creams, hand ointments, lipsticks, skin lotions and creams as well as other formulations.
  • cosmetic compositions include cosmetic, personal cleansing and skin care compositions, and include hair and nail compositions which are topically applied to the humans to achieve a beneficial action on the surface to which it is applied.
  • the esters (a) and (b) are advantageous in that they may be one or more of non-oily, tasteless, inert, essentially non-toxic and non sensitizing, and stable. They are useful as one or more of emollient, solubilizer, moisturizer, plasticizer, sunscreen vehicle/solvent, de-oiler/ degreaser and emulsifier/co-emulsifier .
  • the esters (a) and (b) possess unusual physico-chemical properties, in particular, excellent spreading coefficient which can make it beneficial and unique component of sophisticated delivery system such as in hand, face, and body creams, lotions, soaps and sticks.
  • esters (a) and (b) may be a solvent and/or vehicle for solid organic ultraviolet (UV) absorbers. They may have a function as a plasticizer for polymers contained in skin care composition, and may act as an auxiliary suspending agent capable of assisting in the suspension of ingredients in skincare composition and also may function as a dye levelling agent and/or dye carrier. Thus, the esters (a) and (b) when used in a skin care (or other cosmetic) composition may serve not only as an emollient, but also as a carrier; and it may also exhibit these other functions.
  • UV solid organic ultraviolet
  • the cosmetic composition whose properties may be enhanced by the addition of the esters (a) and (b) can be any conventional cosmetically active material which provides a therapeutic or beneficial cosmetic action to the human body particularly the skin, lips hair or nails.
  • the cosmetic composition can be in the form of a cream, lotion, ointment, spray, soap-bar, stick etc, which contain a cosmetically active material.
  • the term cosmetically active materials may include anti-aging ingredients, anti-wrinkling agents, minerals, preservatives, antioxidants, moisturizers, vitamins, sunscreen agents, and anti-acne agents, deodorants, antiperspirants, etc.
  • the preferred cosmetically active material are vitamins such as Vitamin A, B 1 , B 2 , B 3 , B 5 , B 6 , B 12 , biotin, Vitamin C, Vitamin D, Vitamin E, folic acid and Vitamin K.
  • Other preferred cosmetically active ingredients which can be utilized in the cosmetic composition of this invention include anti- wrinkling agents, anti-acne agents, moisturizers such as Vitamin E, mineral oils and diisopropyl adipate.
  • the cosmetic composition may contain a liquid aqueous carrier medium for the cosmetic composition.
  • the liquid aqueous carrier medium can be water or it can be an oil in water or oil in water liquid emulsion.
  • any cosmetically acceptable carrier which is compatible with the water can be combined with water to form the aqueous carrier medium of the second component system.
  • the aqueous carrier medium can contain one or more oil components.
  • the oil component may be any pharmaceutically or cosmetically acceptable oily material which is substantially insoluble in water. These materials can be found for example in the CTFA International Dictionary of Cosmetic Ingredients as well as the U.S. Pharmacopoeia or other equivalent sources.
  • Suitable oil components include, but are not limited to, natural oils, such as coconut oil; hydrocarbons, such as mineral oil and hydrogenated polyisobutene; sterol derivatives, such as lanolin; animal waxes, such as beeswax, plant waxes, such as carnauba; mineral waxes, such as ozokerite; petroleum waxes, such as paraffin wax; synthetic waxes, such as polyethylene; and mixtures thereof.
  • natural oils such as coconut oil
  • hydrocarbons such as mineral oil and hydrogenated polyisobutene
  • sterol derivatives such as lanolin
  • animal waxes such as beeswax, plant waxes, such as carnauba
  • mineral waxes such as ozokerite
  • petroleum waxes such as paraffin wax
  • synthetic waxes such as polyethylene
  • any conventional solid carrier medium used to formulate such solid cosmetic compositions can be used in accordance with this invention .
  • the cosmetic composition of the second aspect may contain in addition stable ingredients which include various antioxidants, stabilizers, moisturizers, preservatives and emulsifiers such as those mentioned hereinbefore. Any conventional antioxidant, moisturizer, stabilizer, preservative, or emulsifier which is stable in the carrier medium can be present.
  • Emulsifiers such as glycerol stearate or methyl glucose sesquistearate may also be present
  • organic solvents such as lower aliphatic alcohols from 1 to 6 carbon atoms, such as ethanol isopropanol or propanol, or glycols such as glycerin or 1, 2-propylene glycol.
  • perfume oils such as ethylene glycol distearate; wetting agents or emulsifiers; anti-bacterial and fungicidal ingredients; thickeners (such as bentonite) ; pH buffer substances; moisture retaining agents; fragrances or perfumes; perfume oils; colorants (such as natural or synthetic direct dyes but also tinting agents such as fluorescein sodium salt); sunscreens or UV filters; preservatives; antioxidants (such as tocopherols); pyrogemic silicic acid; complexing agents; and also physiologically tolerable inorganic or organic acids, such as phosphoric acid, acetic acid, formic acid, glyoxylic acid, lactic acid, tartaric acid or citric acid; bases; salts (such as sodium chloride); buffers (such as sodium citrate or sodium phosphate); consistency-lending agents; and natural, modified, partly or entirely synthetic polymers (such as chitosan, FMOC chitosan and P
  • these cosmetic compositions do not contain fatty alcohol esters, other than those of the esters (a) and (b) ; or if present such further esters are preferably present within limits set out hereinabove.
  • a method of treating the skin or hair of a person using (a) an ester of an optionally substituted aromatic acid and a C12 primary alcohol and (b) an ester of an optionally substituted aromatic acid and a Ci 4 primary alcohol.
  • Preferred features of the first and second aspects are also preferred features of the third, fourth or fifth aspects.
  • Additive Mixture A is a mixture of Ci 2 and Ci 4 benzoate esters prepared by esterifying approximately 1 mole of a mixture of C 12 and C i4 fatty alcohols sold under the trade name "C12-C14 Midcut Fatty Alcohol” by Procter and Gamble. This is a pure mixture of alcohols specifically composed of approximately 70% by weight of n- dodecanol and 30% by weight of n-tetradecanol, with 1 mole of benzoic acid (i.e. unsubstituted) under standard esterification conditions. The resulting product had an acid value below 0.1 mg KOH/g and had been filtered through a filter press with Whatman Paper No. 4. Additive Mixture A was an odourless liquid with a freezing point of -12 0 C, refractive index of 1.4850 and specific gravity of 0.930 at 25 0 C.
  • the two most commonly used solid organic crystalline sunscreens are 2-hydroxy 4-methoxy benzophenone (called Benzophenone-3 ) , and Parsol 1789 (butyl-methoxy dibenzoyl methane) . These two sunscreens are difficult to dissolve and keep in solution for use in sunscreen formulations for optimal SPF (Sun Protection Factor). Higher solvency for a sunscreen active is desirable as it allows higher concentrations of the sunscreen active ingredient in a formulation. This advantageously raises the SPF ratings for the formulations. As seen from the foregoing table, Additive Mixture A exhibits superiority over commonly used and marketed cosmetic emollients/materials in terms of amounts dissolved.
  • Additive Mixture A for the solid crystalline organic sunscreens is an advantageous effect in formulating sunscreen products for the skincare markets.
  • this ester mixture is an excellent solvent for the above mentioned organic sunscreens.
  • Additive Mixture A provides an anti-washoff effect. This effect is very attractive in formulating long lasting sunscreen products allowing the sunscreen to remain on the skin for longer time.
  • Additive Mixture A The solubility characteristics of Additive Mixture A are tabulated below.
  • the ester mixture is soluble in most commonly used solvents, emollients and vehicles employed in cosmetic product formulations.
  • the soap bars containing Additive Mixture A were found to run better in the extruder, to have better body with consistency than the control bars containing Finsolv TN, to have a transparent or pearlescent effect, and to have better body texture.
  • the bars containing Additive Mixture A produced dense bubbles, and a slippery feel was observed when the bars were wet. After drying, no stickiness was found on the skin. A pleasant soft silky feel with shine and gloss was observed and the skin felt well moisturized.
  • Transparent Combo bars were prepared utilizing the following ingredients in the amounts in the table, given as percent by weight:
  • a hand and body lotion was formulated with the following ingredients in the amounts stated:
  • Disperse carbomer in water Heat to 7O 0 C, add sorbitol and EDTA. Add all Part II ingredients together and heat to 7O 0 C. Add Part II ingredients to Part I ingredients with good mixing. Add triethanolamine, continue mixing. Add Glydant, continue mixing while allowing to cool to room temperature. Discharge and collect.
  • Each product was evaluated. The amount of sample used was 0.5 cc administered by syringe. Each product was evaluated for the following attributes and rated on a scale of 1 to 5, 1 being the best and 5 the worst. Each product was timed from moment of application to the end feel and judged on its absorption time. The products were applied onto the forearm and the opposite hand rubbing into the skin using 4 fingers. The forearm was cleaned with warm water and wiped dry before evaluating another sample. This procedure and scale is used in the rest of the examples in this application relating to sunscreens, skin creams and the like.
  • a waterproof sunscreen lotion was prepared from the following ingredients, in the amounts stated.
  • Formulations A-D so prepared were tested for skin feel, emolliency, slip, stickiness, water rinse-off resistance and moisturizing effect. Results are as follows.
  • a high SPF sunscreen lotion (cold process) was prepared from the following ingredients, in the amounts stated:
  • the high SPF sunscreen lotion was prepared from the ingredients, in the amounts stated.
  • Formulations A-D so prepared were tested for skin feel, emolliency, slip, water rinse-off resistance and moisturizing effect. Results are as follows.
  • a high SPF sunscreen lotion (cold process) was prepared from the following ingredients, in the amounts stated:
  • the high SPF sunscreen lotion was prepared from the ingredients set forth above by the following procedure.
  • Formulations A-D so prepared were tested for skin feel, emolliency, slip, water rinse-off resistance and moisturizing effect. Results are as follows.
  • a sunblock cream was prepared from the following ingredients, in the amounts stated:
  • the sunblock cream was prepared from the ingredients set forth above by the following procedure.
  • Formulations A-D so prepared were tested for skin feel, emolliency, slip, moisturizing effect and water rinse-off resistance. Results are as follows.
  • An emollient cleansing lotion was prepared from the following ingredients, in the amounts stated:
  • Fizul MD 318 C (Disodium oleamido 1 1 1 1 MIPA-sulphosuccinate)
  • Carbopol ETD 2001 resin 0 .2 0 .2 0 .2 0.2
  • the emollient cleansing lotion was prepared from the ingredients set forth above by the following procedure:
  • Disperse carbomer in water Add balance of sub-mixture I ingredients and heat to 75 0 C Mix sub-mixture II ingredients together and heat to 75 0 C. Add sub-mixture II to sub-mixture I with mixing. Combine sub-mixture III ingredients then add to sub-mixture I/II and begin cooling. At 4O 0 C add ingredient IV continue cooling to 3O 0 C.
  • Formulations A-D prepared were tested for slip, skin feel and emolliency. Results are as follows.
  • a hand and body lotion was prepared from the following ingredients, in the amounts stated:
  • the hand and body lotion was prepared from the ingredients set forth above by the following procedure:
  • Disperse carbomer in water Heat to 7O 0 C.
  • Add sorbitol and tetrasodium EDTA Weigh all sub-mixture II ingredients together and heat to 75 0 C.
  • Formulations A-D so prepared were tested for skin feel, slip and emolliency.
  • a light body lotion was prepared from the following ingredients, in the amounts stated:
  • the light body lotion was prepared from the ingredients set forth above by the following procedure:
  • a non-whitening anti-perspirant stick was prepared from the following ingredients, in the amounts stated:
  • the non-whitening antiperspirant stick was prepared from the ingredients set forth above by the following procedure .
  • Formulation A-D so prepared were tested for emolliency, skin feel, slip, stick structure and tackiness. Results are as follows.
  • Deodorant sticks were prepared from the following ingredients, in the amounts stated:
  • the procedure was as follows. Charge all ingredients in to a suitable vessel. Heat to 8O 0 C, with mixing, allowing all ingredients to dissolve. Cool to 6O 0 C and cast into stick moulds .
  • Formulations A-D prepared were tested for skin feel, slip, stick structure, emolliency and tackiness. Results are as follows .
  • a pump spray deodorant was prepared from the following ingredients, in the amounts stated:
  • the pump spray deodorant was prepared from the ingredients set forth above by the following procedure:
  • Formulations A-D so prepared were tested for skin feel, slip, dryness, emolliency and tackiness.
  • a cream antiperspirant was prepared from the following ingredients in the amounts stated:
  • the cream antiperspirant was prepared from the ingredients set forth above by the following procedure:
  • a 2-in-l conditioning shampoo (opaque cream type) was prepared from the following ingredients, in the amounts stated:
  • the shampoo was prepared from the ingredients set forth above by the following procedure:
  • Table A compares the properties of the shampoos of formulations A-D.
  • Table B compares foam results for the shampoos of formulations A-D in a standard foaming test.
  • Table C compares the effects of the shampoos of formulations A, B, C and D.
  • Procedure rinse hair tresses under tap water for 15 seconds. Rinsed hair tresses were treated with shampoo. Shampooed for 5 minutes. Remove the tresses and rinse with running tap water for 15 seconds. Air dry. Perform wet and dry comb tests and assess detangling quality. Assess shine/gloss and dry feel/handle.
  • a clear conditioning shampoo was prepared from the following ingredients in the amounts stated:
  • the clear conditioning shampoo was prepared from the ingredients set forth above by the following procedure:
  • Table A Compares the properties of shampoo preparation of formulation A, B, C and D.
  • Foam results of clear conditioning shampoo preparation of formulation A, B, C and D (using the method described in Example 17) .
  • Table C Compares the effects of shampoo of formulations A, B, C and D on hair tresses (using the method as described in Example 17) .
  • a shower and bath gel was prepared from the following ingredients, in the amounts stated:
  • the shower and bath gel was prepared from the ingredients set forth above by the following procedure.
  • Table A compares the properties of shower and bath gel preparation of formulation of A, B, C and D.
  • a foaming facial cleanser cream was prepared from the following ingredients, in the amounts stated:
  • the foaming facial cleanser cream was prepared from the ingredients, in the amounts stated, by the following procedure :
  • Table A compares the properties of facial cleanser cream of formulation A, B, C and D.
  • Foam results of foaming facial cleanse creme (tested as described in Example 17 above) .

Abstract

A cosmetic composition comprises (a) an ester of an optionally substituted aromatic acid (for example benzoic acid) and a C 12 primary alcohol and (b) an ester of an optionally substituted aromatic acid (for example benzoic acid) and a C 14 primary alcohol. The esters (a) and (b) improve the emolliency of cosmetic compositions including sunscreen, antiperspirant and personal cleansing compositions. There is described an additive composition comprising esters (a) and (b) in amount of at least 60% by weight, which can be mixed with other components to produce the cosmetic composition.

Description

COMPOSITIONS AND USES THEREOF
This invention relates to aromatic esters (for example benzoate esters) of C12 and Ci4 fatty alcohols, to their use in cosmetic compositions, and to additive compositions containing them in admixture.
US 4,275,222 describes benzoic acid esters of a mixture of C12, Ci3, Ci4 and Ci5 primary alcohols, and their use as diluents, solvents, plasticizers and liquid carriers, notably for use in toiletry or cosmetic products, dyestuffs or textiles.
It has now been determined that certain esters composed mainly or essentially of components within the mixtures described in US 4,275,222, when added to a cosmetic composition, particularly a sunscreen composition, provide new and beneficial properties.
In accordance with a first aspect of this invention there is provided an additive composition for enhancing a cosmetic composition, the additive composition comprising in admixture (a) an ester of an optionally substituted aromatic acid and a C12 primary alcohol and (b) an ester of an optionally substituted aromatic acid and a Ci4 primary alcohol, wherein compounds (a) and (b) together provide at least 60% by weight, of the additive composition .
A preferred ester (a) is an ester of an optionally substituted benzoic acid and a branched C12 primary alcohol . A preferred ester (b) is an ester of an optionally substituted benzoic acid and a branched Ci4 primary alcohol .
A general formula for a preferred ester (a) or (b) may be given as
Figure imgf000003_0001
where Q is a substituent, as later defined; m is 0 (zero) or an integer from 1 to 5 (the groups Q being the same as or different from each other when m is 2, 3, 4 or 5) ; and where R is a Ci2 alkyl group in compound (a) , or a Ci4 alkyl group in compound (b) .
The benzene ring (or other aromatic ring system) of ester (a) or (b) may be substituted with 0 to 5 groups (in addition to the reacted acid group COOH) . For example it may be tri- or di-substituted in the ring (or ring system) or, more preferably, mono-substituted. Substitution may be at the ortho, and/or meta, and/or para position(s). The benzene ring (or other aromatic ring) of ester (a) may be substituted and the benzene ring (or other aromatic ring system) of ester (b) may be unsubstituted; or the benzene ring (or other aromatic ring system) of ester (b) may be substituted and the benzene ring (or other aromatic ring system) of ester (a) may be unsubstituted; or both may be substituted, differently or the same; or, most preferably, both may be unsubstituted. The or each substituent of the benzene ring (or other aromatic ring system) of ester (a) or (b) may be any common group used for substitution of a benzene ring (or other aromatic ring system) , for example one or more of an alkyl group (an especially preferred substituent), an alkenyl group, a haloalkyl group, an alkynyl group, a nitrile group, a carboxylic acid (in addition to the reacted carboxylic acid group) , an ester, an ether, an alkoxy group, a haloalkoxy group, a halo group, a hydroxyl group, a mercapto group, an alkylmercapto group, an alkylsulfoxy group, a sulfoxy group, an aryl group, an arylalkyl group, a substituted or unsubstituted amine group or a nitro group. Within these substituents an alkyl group, including of the alkyl moiety of an alkyl- containing group (for example alkoxy or haloalkyl) is suitably a Ci_4 alkyl group, more preferably a methyl group. As already noted, however, most preferably each benzene ring (or other aromatic ring system) is unsubstituted (i.e. m is zero).
The primary alcohol backbone of each ester (a) and (b) may be branched at one or more positions of the backbone of the primary alcohol. Preferably, however, each backbone is linear.
The primary alcohol backbone of each ester (a) and (b) may be unsaturated or it may be saturated.
Preferably esters (a) and (b) of the first aspect of the invention together provide at least 70% by weight of the additive composition, more preferably at least 80%, more preferably at least 90%, more preferably at least 95%. Most preferably they provide at least 98% by weight of the additive composition. In certain highly preferred embodiments the additive composition consists essentially of the esters (a) and (b) .
Preferably, in the additive composition of the first aspect of the invention, the ratio by weight of ester (a) to ester (b) is at least 1:1. Preferably ester (a) is present in weight excess, over ester (b) . More preferably the ratio by weight of ester (a) to ester (b) is at least 1.5:1, most preferably at least 2:1.
Preferably, in the additive composition of the first aspect of the invention, the ratio by weight of ester (a) to ester (b) is up to 5:1, more preferably up to 4:1, and most preferably up to 3:1.
An especially preferred ratio is 2 to 2.75 parts by weight of ester (a) to 1 part by weight of ester (b) .
It has been discovered that the additive composition of the invention can produce enhanced properties when added to cosmetic compositions. These enhanced properties make such additive compositions beneficial for use in cosmetic products such as skin care, topical and personal care products. These products may be in the form of a cream, lotion, bar or stick. The additive compositions of the invention have new and unexpected properties as cosmetic additives not only as an emollient but also as solvents and liquid carriers for a cosmetically active material in the cosmetic preparation. The ester mixture of the first aspect or used in the second aspect may be made, separately or together, by analogous esterification reactions to those used for the preparation of other fatty alcohol-aromatic acid esters.
In accordance with a second aspect of the present invention there is provided a composition for application to the person, for example to hair, skin or nails, comprising (a) an ester of an optionally substituted aromatic acid and a Ci2 primary alcohol and (b) an ester of an optionally substituted aromatic acid and a Ci4 primary alcohol. Said composition may also be called herein a cosmetic composition or a topical composition or a skin benefit composition.
A cosmetic composition of the second aspect has ester (a) to ester (b) present in a weight ratio which is as defined above for the additive composition of the first aspect. However the esters (a) and (b) may have been introduced separately into the cosmetic composition. Thus esters (a) and (b) in the form of an additive composition of the first aspect may be introduced to other ingredients to form a composition of the second aspect, but the invention as defined in the second aspect is not limited in that way.
Further components of a composition of the second aspect of the invention may comprise a carrier or diluent or solvent; and/or a cosmetically effective ingredient. Such further components may be as hereinafter described.
Preferably esters (a) and (b) of a composition of the second aspect of the invention constitute at least 40 %wt, preferably at least 50 %wt, more preferably at least 70 %wt, most preferably at least 90 %wt, of the total weight of C12-C15 fatty alcohol-aromatic acid (ester) content in the cosmetic composition. Most preferably the cosmetic composition is substantially free of C12-C15 fatty alcohol- aromatic acid esters apart from compounds (a) and (b) .
Esters (a) and (b) of a composition of the second aspect of the invention may suitably constitute at least 40 %wt, preferably at least 50 %wt, more preferably at least 70 %wt, most preferably at least 90 %wt, of the total weight of all esters of fatty alcohols and acids in the composition. Most preferably the composition is substantially free of all esters of fatty alcohols and acids apart from the esters (a) and (b) .
The ester mixture of the first aspect may impart valuable properties to the composition of the second aspect. The esters (a) and (b) in admixture are substantially non- greasy, show lack of oiliness and greasiness, have very low cloud point and pour point, have a bland odor, low toxicity and are stable. The esters (a) and (b) in admixture have good tactile properties, spreadability, solubility in/with sunscreen agents, low tackiness (stickiness), low greasiness on the skin, good suspension properties (e.g. TiC>2) and are effective in wetting and dispersing pigments. These properties make the mixture useful as vehicle or carrier emollient or solubilizer for toiletry and cosmetic formulations such as sunscreen creams, hair creams, hand creams, cold creams, manual and electric pre- during- and post-shave compositions, fingernail polish, topical pharmaceutical ointments, lipsticks, skin lotion and creams, as well as other formulations. A particular use for the ester mixture of this invention is as emollients for antiperspirant , deodorant, sun-screening and personal cleansing compositions. The esters (a) and (b) when added to cosmetic compositions, introduce into the cosmetic composition one or more, or all, of the following features :
Ease of emulsification; High refractive index;
Emolliency with good after feel;
Lack of greasiness/pleasant skin feel;
Lack of oiliness yet imparting good lubrication;
Low cloud point and pour point; High spreading coefficient;
Alcohol solubility;
Low toxicity;
Hydrolytic stability; and
Solvent for many skin and hair additives including sunscreens.
The esters (a) and (b) have properties in addition to those mentioned hereinbefore when used as an emollient in a sunscreen agent. In this regard, it has been found that when the ester mixture is incorporated as an emollient in a sunscreen agent, it increases the sun protection factor ("SPF") of the sunscreen agent in these sunscreen compositions. In this manner, one achieves in a sunscreen composition containing the esters (a) and (b) , a sun protecting effect not only due to the sunscreen agent but also due to the esters. Therefore, sunscreen agents of a lower sun protecting factor can be utilized in sunscreen compositions containing the esters (a) and (b) achieve the sunscreen protecting factors of higher protecting sunscreen agents.
For best results, the esters (a) and (b) should be added to a composition when it is substantially pure and substantially free of other esters of aromatic acids and fatty alcohols. In this manner, it is believed that best results are achieved. However, this should not preclude the use of other fatty acid esters or fatty acids in these compositions, suitably within the percentage limits mentioned above, since the use of the esters (a) and (b) may still provide enhanced results to cosmetic compositions in which they are incorporated.
The esters (a) and (b) may be incorporated into cosmetic compositions as an emollient in order to impart to these compositions the aforementioned beneficial properties of this invention. The esters (a) and (b) , whether added individually or together in the form of an additive composition of the first aspect, can be used as an ingredient for any topical or cosmetic compositions including skin, nail, lip, hair topical compositions not only as an emollient but as a diluent, solvent and liquid carrier. As a solvent, the esters (a) and (b) function as an effective solubilizer for the cosmetically active agents used in these cosmetic compositions.
In accordance with this invention, the esters (a) and (b) are suitably incorporated in a cosmetic composition in an emollient effective amount. In this manner, the esters (a) and (b) are provided in an amount at least sufficient to provide the emollient properties to the cosmetic composition. Emollients are dermatologically acceptable compositions that tend to lubricate the skin, increase the softness and suppleness of the skin, prevent or relieve dryness of the skin and/or protect the skin. These emollients are typically water emissible, oily or waxy materials and in order to provide the improved results of this invention, the esters (a) and (b) are employed in any amount sufficient to impart, or improve to any degree, emolliency to the cosmetic composition. The amount of the esters (a) and (b) in these cosmetic compositions depends on the type and quantity of other ingredients used and in the amount and type of functional additives that are utilized. Generally the amount of the esters (a) and (b) that are incorporated into these cosmetic compositions ranges from about 0.1% to about 30% by weight, for example about 0.3% to about 20% by weight, based upon the total weight of the cosmetic composition, with amounts from about 5% to about 15% by weight based upon the total weight of the cosmetic composition being especially preferred.
In a third aspect of the present invention there is provided a method of preparing a cosmetic composition, wherein the esters (a) and (b) , separately or together in an additive composition of the first aspect, are mixed with other ingredient so as to produce a composition of the second aspect of this invention.
The esters (a) and (b) can be utilized to produce the beneficial properties set forth above in any conventional topical cosmetic composition such sunscreen creams, hair creams, hand ointments, lipsticks, skin lotions and creams as well as other formulations. The term cosmetic compositions include cosmetic, personal cleansing and skin care compositions, and include hair and nail compositions which are topically applied to the humans to achieve a beneficial action on the surface to which it is applied.
The esters (a) and (b) are advantageous in that they may be one or more of non-oily, tasteless, inert, essentially non-toxic and non sensitizing, and stable. They are useful as one or more of emollient, solubilizer, moisturizer, plasticizer, sunscreen vehicle/solvent, de-oiler/ degreaser and emulsifier/co-emulsifier . The esters (a) and (b) possess unusual physico-chemical properties, in particular, excellent spreading coefficient which can make it beneficial and unique component of sophisticated delivery system such as in hand, face, and body creams, lotions, soaps and sticks.
Further the esters (a) and (b) may be a solvent and/or vehicle for solid organic ultraviolet (UV) absorbers. They may have a function as a plasticizer for polymers contained in skin care composition, and may act as an auxiliary suspending agent capable of assisting in the suspension of ingredients in skincare composition and also may function as a dye levelling agent and/or dye carrier. Thus, the esters (a) and (b) when used in a skin care (or other cosmetic) composition may serve not only as an emollient, but also as a carrier; and it may also exhibit these other functions.
In accordance with this invention, the cosmetic composition whose properties may be enhanced by the addition of the esters (a) and (b) can be any conventional cosmetically active material which provides a therapeutic or beneficial cosmetic action to the human body particularly the skin, lips hair or nails. The cosmetic composition can be in the form of a cream, lotion, ointment, spray, soap-bar, stick etc, which contain a cosmetically active material. In accordance with this invention the term cosmetically active materials may include anti-aging ingredients, anti-wrinkling agents, minerals, preservatives, antioxidants, moisturizers, vitamins, sunscreen agents, and anti-acne agents, deodorants, antiperspirants, etc. Among the preferred cosmetically active material are vitamins such as Vitamin A, B1, B2, B3, B5, B6, B12, biotin, Vitamin C, Vitamin D, Vitamin E, folic acid and Vitamin K. Other preferred cosmetically active ingredients which can be utilized in the cosmetic composition of this invention include anti- wrinkling agents, anti-acne agents, moisturizers such as Vitamin E, mineral oils and diisopropyl adipate.
If the cosmetic composition is in the form of a liquid, it may contain a liquid aqueous carrier medium for the cosmetic composition. The liquid aqueous carrier medium can be water or it can be an oil in water or oil in water liquid emulsion. In accordance with this invention, any cosmetically acceptable carrier which is compatible with the water can be combined with water to form the aqueous carrier medium of the second component system. The aqueous carrier medium can contain one or more oil components. The oil component may be any pharmaceutically or cosmetically acceptable oily material which is substantially insoluble in water. These materials can be found for example in the CTFA International Dictionary of Cosmetic Ingredients as well as the U.S. Pharmacopoeia or other equivalent sources. Suitable oil components include, but are not limited to, natural oils, such as coconut oil; hydrocarbons, such as mineral oil and hydrogenated polyisobutene; sterol derivatives, such as lanolin; animal waxes, such as beeswax, plant waxes, such as carnauba; mineral waxes, such as ozokerite; petroleum waxes, such as paraffin wax; synthetic waxes, such as polyethylene; and mixtures thereof. If the cosmetic composition is in the form of a solid, such as a deodorant stick, bar or soap, it generally contains a solid carrier medium in the cosmetic composition. Any conventional solid carrier medium used to formulate such solid cosmetic compositions can be used in accordance with this invention .
The cosmetic composition of the second aspect may contain in addition stable ingredients which include various antioxidants, stabilizers, moisturizers, preservatives and emulsifiers such as those mentioned hereinbefore. Any conventional antioxidant, moisturizer, stabilizer, preservative, or emulsifier which is stable in the carrier medium can be present.
To the cosmetic compositions of the second aspect, there may be added known conventional cosmetic additives, adjuvants and vehicle substrates. Emulsifiers such as glycerol stearate or methyl glucose sesquistearate may also be present Also present may be organic solvents, such as lower aliphatic alcohols from 1 to 6 carbon atoms, such as ethanol isopropanol or propanol, or glycols such as glycerin or 1, 2-propylene glycol. The following can also be included in the final cosmetic product: perfume oils; opacifiers such as ethylene glycol distearate; wetting agents or emulsifiers; anti-bacterial and fungicidal ingredients; thickeners (such as bentonite) ; pH buffer substances; moisture retaining agents; fragrances or perfumes; perfume oils; colorants (such as natural or synthetic direct dyes but also tinting agents such as fluorescein sodium salt); sunscreens or UV filters; preservatives; antioxidants (such as tocopherols); pyrogemic silicic acid; complexing agents; and also physiologically tolerable inorganic or organic acids, such as phosphoric acid, acetic acid, formic acid, glyoxylic acid, lactic acid, tartaric acid or citric acid; bases; salts (such as sodium chloride); buffers (such as sodium citrate or sodium phosphate); consistency-lending agents; and natural, modified, partly or entirely synthetic polymers (such as chitosan, FMOC chitosan and PVP) . Naturally, one skilled in the art will be familiar with which of the various individual adjuvants and vehicle substances to be added in order to obtain a desired formulation of the topical cosmetic preparation of this invention. However, in accordance with a preferred aspect of this invention, these cosmetic compositions do not contain fatty alcohol esters, other than those of the esters (a) and (b) ; or if present such further esters are preferably present within limits set out hereinabove.
In accordance with a fourth aspect of the present invention there is provided a method of treating the skin or hair of a person using (a) an ester of an optionally substituted aromatic acid and a C12 primary alcohol and (b) an ester of an optionally substituted aromatic acid and a Ci4 primary alcohol.
In accordance with a fifth aspect of the present invention there is provided the use of (a) an ester of an optionally substituted aromatic acid and a C12 primary alcohol and (b) an ester of an optionally substituted aromatic acid and a Ci4 primary alcohol, together, for any purpose or to achieve any benefit stated herein; and particularly but not exclusively for providing one or more of improved sunscreening, improved moisturizing and improved emolliency .
Preferred features of the first and second aspects are also preferred features of the third, fourth or fifth aspects.
This invention is further illustrated by the following Examples .
In the Examples Additive Mixture A is a mixture of Ci2 and Ci4 benzoate esters prepared by esterifying approximately 1 mole of a mixture of C12 and Ci4 fatty alcohols sold under the trade name "C12-C14 Midcut Fatty Alcohol" by Procter and Gamble. This is a pure mixture of alcohols specifically composed of approximately 70% by weight of n- dodecanol and 30% by weight of n-tetradecanol, with 1 mole of benzoic acid (i.e. unsubstituted) under standard esterification conditions. The resulting product had an acid value below 0.1 mg KOH/g and had been filtered through a filter press with Whatman Paper No. 4. Additive Mixture A was an odourless liquid with a freezing point of -120C, refractive index of 1.4850 and specific gravity of 0.930 at 250C.
In the Examples, the chemical names of the trade or generic names set forth in the Examples are illustrated in the table which follows: Identification Of Trade Or Generic Listed Preparation Ingredients
Figure imgf000016_0001
Figure imgf000017_0001
Figure imgf000018_0001
Example 1 Sunscreen Solubilities in Esters (252C)
The two most commonly used solid organic crystalline sunscreens are 2-hydroxy 4-methoxy benzophenone (called Benzophenone-3 ) , and Parsol 1789 (butyl-methoxy dibenzoyl methane) . These two sunscreens are difficult to dissolve and keep in solution for use in sunscreen formulations for optimal SPF (Sun Protection Factor). Higher solvency for a sunscreen active is desirable as it allows higher concentrations of the sunscreen active ingredient in a formulation. This advantageously raises the SPF ratings for the formulations. As seen from the foregoing table, Additive Mixture A exhibits superiority over commonly used and marketed cosmetic emollients/materials in terms of amounts dissolved.
Figure imgf000019_0001
The high solvency exhibited by Additive Mixture A for the solid crystalline organic sunscreens is an advantageous effect in formulating sunscreen products for the skincare markets. Thus besides being a cosmetic emollient, this ester mixture is an excellent solvent for the above mentioned organic sunscreens.
A further benefit of Additive Mixture A is to provide an anti-washoff effect. This effect is very attractive in formulating long lasting sunscreen products allowing the sunscreen to remain on the skin for longer time.
Example 2 Solubility and compatibility of Additive Mixture A
The solubility characteristics of Additive Mixture A are tabulated below. The ester mixture is soluble in most commonly used solvents, emollients and vehicles employed in cosmetic product formulations.
Figure imgf000019_0002
Figure imgf000020_0001
Key: + indicates soluble at ambient temperatures Key: - indicates insoluble at ambient temperatures
Example 3 Soap Bar Evaluation
An evaluation of the use of Additive Mixture A and Finsolv TN in bar soaps was conducted as described below. The results show improvements in the properties of bar soaps upon inclusion of Additive Mixture A. A soap bar containing Syndet base 96.143-1 was prepared, and a Combo bar (25% Syndet base 96 143-1 and 75% Bradford soap base 80/20) was prepared, each containing 1% Finsolv TN. The typical processing was followed, i.e. the formula was added to the amalgamator, fragrance was incorporated and the bars colored and refined as usual. The bars had the following features during processing and after washing with said bars.
Run well in the extruder. Average body with consistency.
Average body texture.
When using the bars to wash hands with water they give only moderately creamy foam, with small, but not compact bubbles. After drying a soft feel was observed without stickiness, gloss or shine.
Corresponding bars were prepared containing 1% of Additive Mixture A instead of 1% of Finsolv TN
The soap bars containing Additive Mixture A were found to run better in the extruder, to have better body with consistency than the control bars containing Finsolv TN, to have a transparent or pearlescent effect, and to have better body texture. When washed with the water the bars containing Additive Mixture A produced dense bubbles, and a slippery feel was observed when the bars were wet. After drying, no stickiness was found on the skin. A pleasant soft silky feel with shine and gloss was observed and the skin felt well moisturized. Example 4 Transparent Combo bar
Transparent Combo bars were prepared utilizing the following ingredients in the amounts in the table, given as percent by weight:
Figure imgf000022_0001
The procedure was to add ingredients in the order given in the table from glycerin to water, and to heat to 6O0C with mixing. Then add coco fatty acid and stearic acid and mix. Heat to 7O0C and allow components to dissolve. Then add sodium stearate and soap base, and mix. When it becomes clear add Tauranol I 78. Mix and adjust moisture to give clear liquid. Discharge from mixing apparatus and form into bar shapes. The resulting transparent Combo bars containing Additive Mixture A gave better clarity and emolliency compared to bars without Additive Mixture A and containing Finsolv TN.
Example 5 Hand and Body Lotion with Sunscreen
A hand and body lotion was formulated with the following ingredients in the amounts stated:
Figure imgf000023_0001
The procedure for formulating the hand and body lotion is as follows:
Disperse carbomer in water. Heat to 7O0C, add sorbitol and EDTA. Add all Part II ingredients together and heat to 7O0C. Add Part II ingredients to Part I ingredients with good mixing. Add triethanolamine, continue mixing. Add Glydant, continue mixing while allowing to cool to room temperature. Discharge and collect.
Each product was evaluated. The amount of sample used was 0.5 cc administered by syringe. Each product was evaluated for the following attributes and rated on a scale of 1 to 5, 1 being the best and 5 the worst. Each product was timed from moment of application to the end feel and judged on its absorption time. The products were applied onto the forearm and the opposite hand rubbing into the skin using 4 fingers. The forearm was cleaned with warm water and wiped dry before evaluating another sample. This procedure and scale is used in the rest of the examples in this application relating to sunscreens, skin creams and the like.
Results are as follows.
Figure imgf000024_0001
Example 6 Waterproof Sunscreen Lotion
A waterproof sunscreen lotion was prepared from the following ingredients, in the amounts stated.
Figure imgf000025_0001
The procedure for preparing this lotion was as follows:
1. Prepare sub-mixture I by mixing until homogeneous.
2. Mix first four ingredients of sub-mixture II in a separate vessel and stir until oxybenzone is dissolved. 3. Add remaining ingredients of sub-mixture II with mixing .
4. Add sub-mixture II to sub-mixture I with agitation, continue mixing for 40 minutes until smooth.
5. Add component III stirring vigorously until smooth.
6. Discharge and collect.
Formulations A-D so prepared were tested for skin feel, emolliency, slip, stickiness, water rinse-off resistance and moisturizing effect. Results are as follows.
Figure imgf000026_0001
Example 7 High SPF Sunscreen Lotion (cold process)
A high SPF sunscreen lotion (cold process) was prepared from the following ingredients, in the amounts stated:
Figure imgf000027_0001
The high SPF sunscreen lotion was prepared from the ingredients, in the amounts stated.
1. Combine ingredients of sub-mixture I. Mix well.
2. Dissolve hydroxyethylcellulose into the vortex of the agitating water phase. Allow the cellulose to fully hydrate prior to adding the sodium chloride. Add Natrlfine TP-T. Mix until uniform.
3. Add sub-mixture II slowly into sub-mixture I with slow agitation.
4. Mix until homogenous.
Formulations A-D so prepared were tested for skin feel, emolliency, slip, water rinse-off resistance and moisturizing effect. Results are as follows.
Figure imgf000028_0001
Example 8 High SPF Sunscreen Lotion
A high SPF sunscreen lotion (cold process) was prepared from the following ingredients, in the amounts stated:
Figure imgf000029_0001
The high SPF sunscreen lotion was prepared from the ingredients set forth above by the following procedure.
1. Combine ingredients of sub-mixture I. Mix well. 2. Dissolve hydroxyethyl cellulose into the vortex of the agitating water phase. Allow the cellulose to fully hydrate prior to adding the sodium chloride. Add Natrlfine 137-T. Mix until uniform.
3. Add sub-mixture II slowly into sub-mixture I with slow agitation .
4. Mix until homogenous.
Formulations A-D so prepared were tested for skin feel, emolliency, slip, water rinse-off resistance and moisturizing effect. Results are as follows.
Figure imgf000030_0001
Example 9 Sunblock Cream
A sunblock cream was prepared from the following ingredients, in the amounts stated:
Figure imgf000031_0001
The sunblock cream was prepared from the ingredients set forth above by the following procedure.
1. Heat water to 8O0C. Add magnesium aluminium silicate slowly with stirring, mix until smooth.
2. Add remaining ingredients to sub-mixture I and mix until smooth while maintaining temperature.
3. Heat sub-mixture II to 750C, and add to sub-mixture I. 4. Mix until cool to 450C, discharge and collect.
Formulations A-D so prepared were tested for skin feel, emolliency, slip, moisturizing effect and water rinse-off resistance. Results are as follows.
Figure imgf000032_0001
Example 10 Emollient Cleansing Lotion
An emollient cleansing lotion was prepared from the following ingredients, in the amounts stated:
A B C D
I. Water 8 0.4 8 0.4 8 0.4 80.4
Fizul MD 318 C (Disodium oleamido 1 1 1 1 MIPA-sulphosuccinate)
Glycerin 3 3 3 3
Carbopol ETD 2001 resin 0 .2 0 .2 0 .2 0.2
Tetrasodium EDTA 0 .1 0 .1 0 .1 0.1
II . Additive Mixture A 6 .5 - - -
Isopropyl myristate - 6 .5 - -
Isopropyl palmitate - - 6 .5 -
Figure imgf000033_0001
The emollient cleansing lotion was prepared from the ingredients set forth above by the following procedure:
Disperse carbomer in water. Add balance of sub-mixture I ingredients and heat to 750C Mix sub-mixture II ingredients together and heat to 750C. Add sub-mixture II to sub-mixture I with mixing. Combine sub-mixture III ingredients then add to sub-mixture I/II and begin cooling. At 4O0C add ingredient IV continue cooling to 3O0C.
Formulations A-D prepared were tested for slip, skin feel and emolliency. Results are as follows.
Figure imgf000033_0002
Example 11 Hand and Body Lotion
A hand and body lotion was prepared from the following ingredients, in the amounts stated:
Figure imgf000034_0001
The hand and body lotion was prepared from the ingredients set forth above by the following procedure:
Disperse carbomer in water. Heat to 7O0C. Add sorbitol and tetrasodium EDTA. Weigh all sub-mixture II ingredients together and heat to 750C. Add sub-mixture II to sub-mixture I with mixing. Add triethanolamine, continue mixing until temperature has dropped to 450C. Add preservative. Formulations A-D so prepared were tested for skin feel, slip and emolliency.
Figure imgf000035_0001
Example 12 Light Body Lotion
A light body lotion was prepared from the following ingredients, in the amounts stated:
Figure imgf000035_0002
The light body lotion was prepared from the ingredients set forth above by the following procedure:
Mix the ingredients of sub-mixture I and heat to 650C. Mix the ingredients of sub-mixture II and heat to 7O0C. Add sub-mixture I to sub-mixture II with mixing, maintaining temperature 7O0C. Mix for 15 minutes. Cool with mixing to 250C.
Formulations A-D so prepared were tested for skin feel, slip and emolliency. Results are as follows.
Figure imgf000036_0001
Example 13 Non-whitening Antiperspirant Stick
A non-whitening anti-perspirant stick was prepared from the following ingredients, in the amounts stated:
Figure imgf000037_0001
The non-whitening antiperspirant stick was prepared from the ingredients set forth above by the following procedure .
1. Combine ingredients of sub-mixture I and heat to 750C with mixing.
2. Add sub-mixture II powders. Mix for 15 minutes or until completely dispersed. Maintain at 750C.
3. Cool to 550C, and mold sticks. Each product was evaluated by rubbing the anti-perspirant stick 10 times in a back and forth motion with a constant applied pressure on the arm to ensure even application. After the evaluation, the test product was washed off from the arm and the arm patted dry. The next evaluation was not performed until the arm was totally dry. Al to 5 scale was used, with 1 being the best and 5 being the worst .
This procedure and scale is used in the rest of the examples in this application relating to anti-perspirant and deodorant sticks, unless otherwise stated.
Formulation A-D so prepared were tested for emolliency, skin feel, slip, stick structure and tackiness. Results are as follows.
Figure imgf000038_0001
Example 14 Deodorant Stick
Deodorant sticks were prepared from the following ingredients, in the amounts stated:
A B C D
Propylene glycol 71 71 71 71
Water 14 14 14 14
Additive Mixture A 3 - - -
Isopropyl myristate - 3 - -
Isopropyl palmitate - - 3 -
Finsolv TN - - - 3
Sodium stearate 5 5 5 5
Triclosan 0. 2 0. 2 0. 2 0. 2
Pentadoxynol-200 6. 6 6. 5 6. 5 6. 5
Triethanolamine 99% 0. 3 0. 3 0. 3 0. 3
The procedure was as follows. Charge all ingredients in to a suitable vessel. Heat to 8O0C, with mixing, allowing all ingredients to dissolve. Cool to 6O0C and cast into stick moulds .
Formulations A-D prepared were tested for skin feel, slip, stick structure, emolliency and tackiness. Results are as follows .
Figure imgf000039_0001
Example 15 Pump Spray Deodorant
A pump spray deodorant was prepared from the following ingredients, in the amounts stated:
Figure imgf000040_0001
The pump spray deodorant was prepared from the ingredients set forth above by the following procedure:
Combine alcohol, water and triclosan. Mix well. Add balance of ingredients with mixing.
Formulations A-D so prepared were tested for skin feel, slip, dryness, emolliency and tackiness.
Figure imgf000040_0002
Example 16 Cream antiperspirant
A cream antiperspirant was prepared from the following ingredients in the amounts stated:
Figure imgf000041_0001
The cream antiperspirant was prepared from the ingredients set forth above by the following procedure:
1. Disperse sodium magnesium silicate in water and heat to 7O0C.
2. Blend and heat the oil phase to 7O0C.
3. Add sub-mixture I to sub-mixture II with mixing.
4. Cool the cream to 5O0C and add aluminium chlorohydrate .
5. Mix for 30 minutes and pack. Formulations A-D prepared were tested for skin feel, slip, dryness, emolliency and tackiness, as described above for cream preparations. Results are as follows.
Figure imgf000042_0001
Example 17 2 in 1 Conditioning Shampoo (opaque cream type)
A 2-in-l conditioning shampoo (opaque cream type) was prepared from the following ingredients, in the amounts stated:
Figure imgf000043_0001
The shampoo was prepared from the ingredients set forth above by the following procedure:
1. Mix gums together and pre-wet with propylene glycol.
2. Add gums and propylene glycol to water with good mixing to disperse. When dispersed heat mixture to 650C.
3. Sequentially add components of sub-mixture II at 650C with mixing allowing each to become uniform before adding the next .
4. Add components of sub-mixture III together, heating to 650C, with mixing until all are melted.
5. Add to balance of formula with good mixing and allow to become uniform. Continue mixing while cooling.
6. Add ingredient IV at 450C. Cool to 350C, discharge and collect.
Table A compares the properties of the shampoos of formulations A-D. Table B compares foam results for the shampoos of formulations A-D in a standard foaming test. Table C compares the effects of the shampoos of formulations A, B, C and D.
Figure imgf000045_0001
Table B
Foam results of 2-in-l conditioning shampoo preparation of Formulations A, B, C and D.
Figure imgf000045_0002
Procedure : 1% of the product was dissolved in 200 ml water and was shaken in a 500 ml cylinder with 10 sets of shakes. Table C
Comparison of effects of 2-in-l conditioning shampoo preparation of formulations A, B, C and D on hair tresses.
Figure imgf000046_0001
All measurements are on a scale of 1-10, with 1 being best and 10 being worst.
Procedure: rinse hair tresses under tap water for 15 seconds. Rinsed hair tresses were treated with shampoo. Shampooed for 5 minutes. Remove the tresses and rinse with running tap water for 15 seconds. Air dry. Perform wet and dry comb tests and assess detangling quality. Assess shine/gloss and dry feel/handle.
Example 18 Clear Conditioning Shampoo
A clear conditioning shampoo was prepared from the following ingredients in the amounts stated:
A B C D
Water 51. 2 51.2 51.2 51. 2
Sodium laureth sulfate 25% 28. 0 28.0 28.0 28. 0
Tauranol WS (cone) 15. 0 15.0 15.0 15. 0
Aminol HCA 4.0 4.0 4.0 4.0
Additive Mixture A 1.0 - - -
Isopropyl myristate - 1.0 - -
Isopropyl palmitate - - 1.0 -
Finsolv TN - - - 1.0
Crothix 0.3 0.3 0.3 0.3
DMDM Hydartoin 0.2 0.2 0.2 0.2
The clear conditioning shampoo was prepared from the ingredients set forth above by the following procedure:
Charge water and heat to 750C. Add all ingredients in order except DMDM Hydratoin. Mixing well. Cool to 450C and add DMDM Hydratoin. Cool to room temperature.
Table A Compares the properties of shampoo preparation of formulation A, B, C and D.
Table A
Properties of clear conditioning shampoo of formulation A, B, C and D.
Figure imgf000048_0001
Table B
Foam results of clear conditioning shampoo preparation of formulation A, B, C and D (using the method described in Example 17) .
Figure imgf000048_0002
Table C Compares the effects of shampoo of formulations A, B, C and D on hair tresses (using the method as described in Example 17) .
Table C
Comparison of effects of clear conditioning shampoo preparation of formulation A, B, C and D.
Figure imgf000049_0001
Example 19 Shower and Bath Gel
A shower and bath gel was prepared from the following ingredients, in the amounts stated:
Figure imgf000050_0001
The shower and bath gel was prepared from the ingredients set forth above by the following procedure.
Heat water to 5O0C and add all sub-mixture I ingredients in the order stated, allowing each to mix well. Raise temperature to 7O0C and add sub-mixture II ingredients allowing each to mix well. Cool to 450C and add DMDM Hydantoin. Cool to below 350C and adjust pH using citric acid. Pour when warm.
Table A compares the properties of shower and bath gel preparation of formulation of A, B, C and D.
Table A
Properties of shower and bath gel formulation A, B, C and D,
Figure imgf000051_0001
Table B
Foam Results of shower and bath gel preparation of formulation A, B, C and D (method as described in Example 17) .
Figure imgf000052_0001
Example 20 Foaming Facial Cleanser Cream
A foaming facial cleanser cream was prepared from the following ingredients, in the amounts stated:
Figure imgf000052_0002
The foaming facial cleanser cream was prepared from the ingredients, in the amounts stated, by the following procedure :
Combine the components of sub-mixture I and heat to 750C with gentle stirring until a homogeneous system is formed. Avoiding aeration, separately combine components of sub- mixture II and heat with mixing to 6O0C. Add the molten sub-mixture II slowly to the vortex of sub-mixture I and continue stirring until cooled below 4O0C. The resultant product builds viscosity and pearlescence in 48 hrs.
Table A compares the properties of facial cleanser cream of formulation A, B, C and D.
Figure imgf000053_0001
Table B
Foam results of foaming facial cleanse creme (tested as described in Example 17 above) .
Preparation of formulation A, B, C and D.
Figure imgf000054_0001
General comment applicable throughout
In this specification, including in the examples, percentage values are expressed in terms of weight by total composition weight (wt/wt) unless otherwise stated.

Claims

Claims
1. An additive composition for enhancing a cosmetic composition, the additive composition comprising in admixture (a) an ester of an optionally substituted aromatic acid and a C12 primary alcohol and (b) an ester of an optionally substituted aromatic acid and a Ci4 primary alcohol, wherein compounds (a) and (b) together provide at least 60% by weight, of the additive composition.
2. A composition as claimed in claim 1 wherein the optionally substituted aromatic acid for ester (a) and for ester (b) is optionally substituted benzoic acid.
3. An ester as claimed in claim 1 or 2 wherein the aromatic acid for ester (a) and for ester (b) is unsubstituted.
4. An additive composition as claimed in any preceding claim wherein the ratio by weight of ester (a) to ester (b) is in the range from 5:1 to 1:1.
5. An additive composition as claimed in claim 4 wherein said ratio is in the range of from 1.5:1 to 3:1.
6. An additive composition as claimed in any preceding claim wherein the esters (a) and (b) together constitute at least 80% by weight, of the additive composition.
7. An additive composition as claimed in claim 6, wherein the composition consists essentially of the esters (a) and (b) .
8. A composition for application to the person, the composition comprising (a) an ester of an optionally substituted aromatic acid and a C12 primary alcohol and (b) an ester of an optionally substituted aromatic acid and a Ci4 primary alcohol.
9. A composition as claimed in claim 8 wherein the aromatic acid for ester (a) and for ester (b) is unsubstituted benzoic acid.
10. A composition as claimed in claim 8 or 9 wherein the ratio by weight of ester (a) to ester (b) in the cosmetic composition is in the range from 5:1 to 1:1.
11. A composition as claimed in claim 8, 9 or 10 wherein the combined weight of esters (a) and (b) is in the range from 0.1 % to 30 %, by total weight of the composition.
12. A composition as claimed in any of claims 8 to 11 comprising a carrier or diluent or solvent; and/or a cosmetically effective ingredient, for example selected from a sunscreen agent, a deodorant agent, an antiperspirant agent and a personal cleansing agent.
13. A composition as claimed in any of claims 8 to 12 wherein the esters (a) and (b) function in the composition as emollients and are the only emollients present in the composition .
14. A composition as claimed in any of claims 8 to 13 wherein the esters (a) and (b) constitute at least 40 %wt, more preferably at least 50 %wt, most preferably at least 70 %wt, most preferably at least 90 %wt, and preferably substantially all, of the total weight of C12-C15 fatty alcohols-aromatic acid esters in the composition.
15. A composition as claimed in any of claims 8 to 14 wherein the esters (a) and (b) constitute at least 40 %wt, preferably at least 50 %wt, more preferably at least 70 %wt, most preferably at least 90 %wt, and preferably substantially all, of the total weight of all esters of fatty alcohols and acids in the composition.
16. A composition as claimed in any of claims 8 to 15 wherein esters (a) and (b) are supplied in the form of an additive composition as claimed in any of claims 1 to 7.
17. A method of preparing a cosmetic composition as claimed in any of claims 8 to 16 by admixture of the compounds (a) and (b) with other ingredients.
18. A method of treating the skin or hair of a person using an (a) an ester of an optionally substituted aromatic acid and a C12 primary alcohol and (b) an ester of an optionally substituted aromatic acid and a Ci4 primary alcohol.
19. Use of (a) an ester of an optionally substituted aromatic acid and a C12 primary alcohol and (b) an ester of an optionally substituted aromatic acid and a Ci4 primary alcohol, together, for providing one or more of improved sunscreening, improved moisturizing and improved emolliency .
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WO2017144865A1 (en) * 2016-02-26 2017-08-31 RECKITT BENCKISER LAUNDRY DETERGENTS (No.1) BV Composition
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