WO2023164720A1 - Composition émolliente stable à l'oxydation - Google Patents

Composition émolliente stable à l'oxydation Download PDF

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Publication number
WO2023164720A1
WO2023164720A1 PCT/US2023/063396 US2023063396W WO2023164720A1 WO 2023164720 A1 WO2023164720 A1 WO 2023164720A1 US 2023063396 W US2023063396 W US 2023063396W WO 2023164720 A1 WO2023164720 A1 WO 2023164720A1
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Prior art keywords
cocoa butter
fatty acid
hydrogenated
skin
care formulation
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PCT/US2023/063396
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English (en)
Inventor
Jeffrey Pearson ADDY
Frédéric NIOLA
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Cargill, Incorporated
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Publication of WO2023164720A1 publication Critical patent/WO2023164720A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/12—Preparations containing hair conditioners
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier 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
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations

Definitions

  • An emollient is a personal care product commonly used for relieving skin dryness by keeping skin moist.
  • Emollients can be a wide spectrum of various ingredients, from synthetically derived compounds (e.g., mineral oils), to natural components (e.g., vegetable oils).
  • Mineral oils byproducts of petroleum refining, have long been around as a major component in emollient formulations due to its low volatility and smoothing texture. Like other moisturizers, mineral oils help to lock in moisture to sooth dry and irritated skin. However, since mineral oils do not readily absorb into and penetrate the skin, they remain on the skin surface and can clog pores, causing other problems to the skin.
  • Cocoa butter is the fat derived from cocoa beans. It is widely accepted and recognized as an essential ingredient for making chocolate and confectioneries. With a pleasing fatty acid profile and a good smell of the skin, cocoa butter has emerged as one of the most promising and healthy ingredients in cosmetic and person care products.
  • the present disclosure provides an emollient composition comprising a mixture of hydrogenated cocoa butter fatty acid C1-C6 alkyl esters. Also described herein is a personal care formulation comprising the emollient composition. The present disclosure further provides a method of making a composition comprising hydrogenated cocoa butter fatty acid C1-C6 alkyl esters.
  • substantially refers to a majority of, or mostly, as in at least about 50%, 60%, 70%, 80%, 90%, 95%, 96%, 97%, 98%, 99%, 99.5%, 99.9%, 99.99%, or at least about 99.999% or more, or 100%.
  • fatty acid refers to a molecule comprising a hydrocarbon chain and a terminal carboxylic acid group.
  • carboxylic acid group of the fatty acid may be modified or esterified, for example as occurs when the fatty acid is incorporated into a glyceride or another molecule (e.g., COOR, where R refers to, for example, a carbon atom).
  • the carboxylic acid group may be in the free fatty acid or salt form (i.e., COO or COOH).
  • the ‘tail’ or hydrocarbon chain of a fatty acid may also be referred to as a fatty acid chain, fatty acid sidechain, or fatty chain.
  • the hydrocarbon chain of a fatty acid will typically be a saturated or unsaturated aliphatic group.
  • a fatty acid having N number of carbons will typically have a fatty acid side chain having N-l carbons.
  • acylglyceride refers to a molecule having at least one glycerol moiety with at least one fatty acid residue that is linked via an ester bond.
  • acyl glycerides can include monoacylglycerides, diacylglycerides, triacylglycerides.
  • the group acylglycerides can be further refined by additional descriptive terms and can be modified to expressly exclude or include certain subsets of acylglycerides.
  • the phrase mono- and di- acylglycerides refers to MAGs (monoacylglycerides) and DAGs (diacylglycerides), while the phrase non-MAG/non-DAG acylglycerides refers to a group of acylglycerides which exclude MAGs and DAGs.
  • a “fatty acid residue” is a fatty acid in its acyl or esterified form.
  • the levels of particular types of fatty acids may be provided herein in percentages out of the total fatty acid content of an oil. Unless specifically noted otherwise, such percentages are weight percentages based on the total fatty acids, including free fatty acids and esterified fatty acids as calculated experimentally.
  • a "saturated" fatty acid is a fatty acid that does not contain any carbon-carbon double bonds in the hydrocarbon chain.
  • stearic acid Cl 8:0
  • An "unsaturated” fatty acid contains one or more carbon-carbon double bonds.
  • oleic acid C18:l
  • a "polyunsaturated” fatty acid contains more than one such carbon-carbon double bond while a “monounsaturated” fatty acid contains only one carbon-carbon double bond.
  • Carbon-carbon double bonds may be in one of two stereoconfigurations denoted cis and trans.
  • Naturally- occurring unsaturated fatty acids are generally in the "cis" form.
  • Non-limiting examples of fatty acids include C14, C16 (e.g., C16:0, C16: l), C18 (e.g., C18:0, C18: l, C18:2, C18:3, C18:4), C20 (e.g., C20:0, C20:l, C20:2, C20:3, C20:4, C20:5), C22 (e.g., C22:0, C22: l, C22:2, C22:3, C22:4, C22:5, C22:6), and C24 (e.g., C24:0, C24: l, C24:2, C24:3, C24:4, C24:5, C24:6, C24:7) fatty acids.
  • C16 e.g., C16:0, C16: l
  • C18 e.g., C18:0, C18: l, C18:2, C18:3, C18:4
  • C20 e.g., C20:0,
  • the fatty acids can be myristic (14:0), palmitic (16:0), stearic or isostearic (18:0), oleic (18: 1), linoleic (18:2) and a-linolenic (18:3) acids.
  • C14-C24 fatty acid as used herein means a fatty acid containing 14-24 carbons.
  • the C14-C24 fatty acid may be straight or branched.
  • the C14-C24 fatty acid is a C16 and/or Cl 8 fatty acid.
  • the C14-C24 fatty acid may be a mixture of C14-C24 fatty acids.
  • C1-C6 alkyl ester or alkyl ester means a fatty acid containing 14-24 carbons which is esterified with a C1-C6 alkyl group.
  • ethyl ester means a fatty' acid containing 14-24 carbons that is esterified with an ethyl group.
  • the C1-C6 alkyl group may be straight or branched. In one aspect, the C1-C6 alkyl has a straight chain. In one aspect, the C1-C6 alkyl is an ethyl group.
  • hydroxinated C1-C6 alkyl ester or hydrogenated alkyl ester as used herein means a fatty acid C1-C6 alkyl esters that is partially, substantially, or completely hydrogenated.
  • hydrogenated ethyl ester means a fatty acid containing 14-24 carbons that is esterified with an ethyl group, and is partially, substantially, or completely hydrogenated.
  • the fatty acid composition of an oil can be determined by methods well known in the art.
  • the American Oil Chemist's Society (AOCS) maintains analytical methods for a wide variety of tests performed on vegetable oils. Hydrolysis of the oil's components to produce free fatty acids, conversion of the free fatty acids to methyl esters, and analysis by gas-liquid chromatography (GLC) is the universally accepted standard method to determine the fatty acid composition of an oil sample.
  • the AOCS Procedure Ce 1-62 describes the procedure used.
  • Iodine Value (commonly abbreviated as IV) as used herein is the mass of iodine in grams that is consumed by 100 grams of a chemical substance. Iodine numbers are often used to determine the amount of unsaturation in fats, oils, and waxes. In fatty acids, unsaturation occurs mainly as double bonds which are very reactive towards halogens, iodine in this case. Thus, the higher the iodine value, the more unsaturation is present in the sample.
  • the Iodine Value of a material can be determined by the standard well-known Wijs method (A.O.C.S. Cdl-25).
  • esterification or esterified means the creation of an ester bond including: 1) the dehydration reaction of an alcohol with an acid; 2) transesterification, the reaction of an alcohol with an ester to form a new ester; or 3) interesterification, the rearrangement of fatty acids within a triacylglycerol structure
  • a “cocoa butter” as used herein refers to a triacylglyceride (triglyceride or triacylglycerol) derived from a mixture of fatty acids derived from the seeds of the cocoa plant.
  • fatty acids of cocoa butter include C14 (e.g., C14:0), C16 (e.g., C16:0, C16: l), C18 (e.g., C18:0, C18:l, C18:2, C18:3), C20 (e.g., C20:0, C20:l), C22 (e.g., C22:0), and C24 (e.g., C24:0) fatty acids.
  • the cocoa butter has a fatty acid profile that includes, but not limited to, myristic acid (C14:0), palmitic acid (C16:0), palmitoleic acid (C16: l), stearic acid (C18:0), oleic acid (C18: l), linoleic acid (C18:2), a-linolenic (C18:3), arachidic acid (C20:0), paullinic acid (C20: 1), behenic acid (C22:0), and lignoceric acid (C24:0).
  • myristic acid C14:0
  • palmitic acid C16:0
  • palmitoleic acid C16: l
  • stearic acid C18:0
  • oleic acid C18: l
  • linoleic acid C18:2
  • a-linolenic C18:3
  • arachidic acid C20:0
  • paullinic acid C20: 1
  • a “cocoa butter fatty acid C1-C6 alkyl ester” or “cocoa butter C1-C6 alkyl ester” as used herein refers to a cocoa butter fatty acid containing 14-24 carbons (C14-C24 fatty acid) esterified with a C1-C6 alkyl group.
  • a “hydrogenated cocoa butter fatty acid C1-C6 alkyl ester” or “hydrogenated cocoa butter C1-C6 alkyl ester” as used herein refers to a cocoa butter fatty acid C1-C6 alky l ester or a cocoa butter C1-C6 alkyl ester that is partially, substantially, or completely hydrogenated.
  • a “cocoa butter fatty acid ethyl ester” or “cocoa butter ethyl ester (CBEE)” as used herein refers to a cocoa butter fatly acid containing 14-24 carbons (C14-C24 fatty acid) esterified with an ethyl group.
  • An emollient may be, without limitation, a lotion, a cream, and an ointment depending on the water-to-oil ratio.
  • the emollient is a vegetable oil and/or a vegetable fat such as cocoa butter.
  • the emollient comprises esters derived from cocoa butter fatty acid that include, but not limited to, cocoa butter fatty acid ethyl esters.
  • the emollient comprises hydrogenated esters derived from cocoa butter fatty acid that include, but not limited to, hydrogenated cocoa butter fatty acid C1-C6 alkyl esters, such as hydrogenated cocoa butter fatty acid ethyl esters.
  • personal care formulation or personal care product means and comprises any cosmetic, hygienic, toiletry, skin care, and topical care products including, without limitation, leave-on products (i. e. , products that are left on keratinous substrates after application); rinse-off products (i.e., products that are washed or rinsed from keratinous substrates during or within a few minutes of application); shampoos; hair curling and hair straightening products; hair style maintaining and hair conditioning products; lotions and creams for nails, hands, feet, face, scalp and/or body; hair dye; face and body makeup; nail care products; astringents; deodorants; antiperspirants; anti-acne; antiaging; depilatories; colognes and perfumes; skin protective creams and lotions (such as sunscreens); skin and body cleansers; skin conditioners; skin toners; skin firming compositions; skin tanning and lightening compositions; liquid soaps; bar soaps; bath products; and shaving
  • the texture of such personal care formulation or personal care product is not limited and may be, without limitation, a liquid, gel, spray, emulsion (such as lotions and creams), shampoo, pomade, foam, tablet, stick (such as lip care products), makeup, among others, any of which can be applied to the skin or hair or hair and which typically are designed to remain in contact therewith until removed, such as by rinsing with water or washing with shampoo or soap.
  • Other forms could be gels that can be soft, stiff, or squeezable.
  • Sprays can be non-pressurized aerosols delivered from manually pumped finger-actuated sprayers or can be pressurized aerosols such as mousse, spray, or foam forming formulation, where a chemical or gaseous propellant is used.
  • the topical formulation comprising the emollient composition disclosed herein may be a cream used for skincare applications.
  • Formulations prepared using the composition disclosed herein have a white or pale white color that is generally considered to be aesthetically appealing.
  • the formulations of the invention may be further processed to make a colored end product.
  • the white color is beneficial because it will show up the additional pigment without influencing the final color.
  • formulations prepared using the composition disclosed herein have an acceptable oil content and good spreadability with less greasy residual feeling on the skin. This texture feels pleasant to touch and apply. Furthermore, the consistency is such that good product pick-up may be achieved. Good product pick-up means that sufficient product (i.e., not too much, and not too little) can be collected on the user’s finger.
  • composition of the present disclosure is also useful in sunscreen applications.
  • Sunscreens contain ingredients intended to block UV radiation from reaching the skin.
  • UV blockers or sunscreen agents can be physical such as chemical salts like ZnO or TiO2, or chemical (max authorized level indicated) such as avobenzone (3%), homosalate (15%), butyl methoxydibenzoylmethane (5%); octocrylene (10%); titanium dioxide (25%); ethylhexyl salicylate (5%); ethylhexyl methoxycinnamate (10%); bis-ethylhexyloxyphenol methoxyphenyl triazine (10%); composition of the present disclosure can be used with any type of UV blocker sunscreen agent known in the art or mixtures of UV blockers or sunscreen agents.
  • the “Mettler Drop Point” is the temperature at which a solid fat becomes fluid to flow.
  • the MDP can be determined, for example, using the ASTM Standard D127-19.
  • the emollient composition described herein comprises a mixture of hydrogenated cocoa butter fatty' acid C1-C6 alkyl esters.
  • the hydrogenated cocoa butter faty acid C1-C6 alkyl ester is hydrogenated cocoa buter fatty acid ethyl ester or hydrogenated cocoa butter ethyl ester (HCBEE).
  • HCBEE has a fatty acid ethyl ester profile as shown in Table 1.
  • HCBEE comprises about 15% to about 30%, about 20% to about 30%, or about 24% to about 28% palmitic acid ethyl ester.
  • HCBEE comprises about 65% to about 80%, about 70% to about 80%, or about 70% to about 75% stearic acid ethyl ester.
  • HCBEE comprises about 15% to about 30% palmitic acid ethyl ester and about 65% to about 80% stearic acid ethyl ester. In one aspect, HCBEE comprises about 24% to about 28% palmitic acid ethyl ester and about 70% to about 75% stearic acid ethyl ester.
  • the emollient composition comprises greater than 50%, greater than 75%, greater than 90%, greater than 95%, or greater than 99% hydrogenated cocoa butter fatty acid C 1 -C6 alkyl esters.
  • content of the hydrogenated cocoa butter fatty acid C 1 - C6 alkyl esters in the emollient composition is a range of about 50% to about 99%, about 75% to about 99%, about 90% to about 99%, about 95% to about 99%, about 95% to about 99.3%, about 95% to about 99.5%, or about 99.3% to about 99.5%.
  • content of the hydrogenated cocoa butter fatty acid C1-C6 alkyl esters in the emollient composition is about 99.3% or about 99.5%.
  • the emollient composition can be blended with other emollients, such as natural emollients, synthetic emollients, and/or petroleum-based emollients.
  • the emollient composition comprises greater than 50%, greater than 75%, greater than 90%, greater than 95%, or greater than 99% HCBEE.
  • content of the HCBEE in the emollient composition is a range of about 50% to about 99%, about 75% to about 99%, about 90% to about 99%, about 95% to about 99%, about 95% to about 99.3%, or about 95% to about 99.5%.
  • content of the HCBEE in the emollient composition is about 99.3% or about 99.5%.
  • the Mettler drop points of the hydrogenated cocoa butter fatty acid C1-C6 alkyl esters is in a range of about 33°C to about 37°C, about 33°C to about 36°C, about 33°C to about 35°C, or about 33°C to about 34°C.
  • the Mettler drop points of HCBEE is in a range of about 33°C to about 37°C, about 33°C to about 36°C, about 33°C to about 35°C, or about 33°C to about 34°C.
  • HCBEE produced by the method described herein has a solid appearance and a rich texture with an off-white color. Further, HCBEE can easily melt on the skin and leaves a light film on the skin surface, providing a cushiony effect. These characteristics make HCBEE a good candidate for applications such as personal care and cosmetic products.
  • HCBEE can be added in lotions, creams, or skin care products at a loading level of 1 - 10%.
  • HCBEE can be added in anhydrous balms or sticks at a loading level of 1 - 20%.
  • HCBEE can be added in hair care products at a loading level of 1 - 5%.
  • the HCBEE has a viscosity, determined by a Brookfield viscometer, of about 46,600 mPa.s.
  • the personal care formulation described herein comprises an emollient composition, in which the emollient composition comprises a mixture of hydrogenated cocoa butter fatty acid C1-C6 alkyl esters.
  • the hydrogenated cocoa butter fatty acid Cl- C6 alkyl ester is hydrogenated cocoa butter fatty acid ethyl ester (HCBEE).
  • HCBEE has a fatty acid ethyl ester profile as shown in Table 1.
  • the personal care formulation described herein can contain any useful amount of the hydrogenated cocoa butter fatty acid C1-C6 alkyd esters of the present disclosure.
  • content of the hydrogenated cocoa butter fatty acid C1 -C6 alkyl esters in the personal care formulation is in a range of 1% to 100%, 10% - 50%, 15% - 45%, 20% - 40%, 22%
  • content of the hydrogenated cocoa butter fatty acid C1-C6 alkyl esters in the personal care formulation is 30% by weight.
  • the personal care formulation described herein can contain any useful amount of the HCBEE of the present disclosure.
  • the content of HCBEE in the personal care formulation is in a range of 1% to 100%, 10% - 50%, 15% - 45%, 20% - 40%, 22%
  • content of the HCBEE in the personal care formulation is 30% by weight.
  • the method of making hydrogenated cocoa butter fatty acid C1-C6 alkyl ester described herein comprises a hydrogenation step of the cocoa butter, and an esterification step of mixing the hydrogenated cocoa butter with C1-C6 alkyl alcohol to obtain the HCBEE.
  • the hydrogenation step is carried out before esterification step.
  • the esterification step can be earned out before the hydrogenation step.
  • the method of making the hydrogenated cocoa butter fatty acid C1-C6 alkyl esters comprises the steps of: (a) providing cocoa butter and C1-C6 alkyl alcohol; (b) hydrogenating the cocoa buter with hydrogen gas in the presence of a hydrogenation catalyst to obtain a hydrogenated cocoa buter; and (c) mixing the hydrogenated cocoa buter and the C1-C6 alkyl alcohol in the presence of an esterification catalyst at an esterification temperature to obtain the hydrogenated cocoa buter fatty acid C1-C6 alkyl esters.
  • Esterification of triglyceride vegetable oils is well known in the art, for example, in the preparation of bio-diesel.
  • the oil is mixed with an excess of an alcohol(s) and heated to an elevated temperature in the presence of a catalyst.
  • the catalyst needs not be but typically is a metal salt of the corresponding alcohol.
  • the choice of reaction temperature is related to the alcohol utilized and a skilled artisan would choose a temperature to balance the reaction rate with the creation of undesired side products.
  • the esterification temperature is about 70°C
  • the alcohol is ethanol
  • the esterification catalyst is sodium ethoxide.
  • Hydrogenation of triglyceride vegetable oils and esterified fatty acids is also well known in the art.
  • the oil or in this case the cocoa butter fatty acid C1-C6 alkyl esters
  • a catalyst While many catalysts can be employed, nickel-based catalysts are commonly employed.
  • the hydrogenation is allowed to proceed until a desired end point is reached.
  • the iodine value (IV) of the oil can be monitored to understand the amount of unsaturated double bonds remaining in the product. It is well understood in the art that it is often difficult, expensive, or impractical to completely eliminate all double bonds in an oil that is being hydrogenated.
  • the catalyst can be removed by simple filtration to yield the hydrogenated cocoa buter fatty acid C1-C6 alkyl esters.
  • the hydrogenation catalyst is nickel (Pricat 9910, Johnson Mathey Process Technologies).
  • the method may include additional steps to purify and/or modify the hydrogenated cocoa buter fatty acid C1-C6 alkyl ester.
  • the hydrogenated cocoa buter fatty acid C1-C6 alkyl ester can be desolventized with nitrogen gas and at reduced pressure to remove solvents and volatiles such as ethanol.
  • the desolventized hydrogenated cocoa buter fatty acid C 1 -C6 alky l ester can be decanted with nitrogen gas, bleached by a bleaching agent, and deodorized by a deodorizing agent or process. These procedures are also well known in the art of vegetable oil purification and are referred to as “refining”. These steps can be easily modified or varied depending on the impurities sought to be removed.
  • Table 2 shows the ingredients for making HCBEE using the method described herein.
  • This method starts with the hydrogenation step. Cocoa butter was first melted, and the melted cocoa butter was heated to 135°C under a stream of hydrogen gas and in the presence of heterogenous nickel catalyst (Pricat 9910, Johnson Matthey Process Technologies). Iodine Value (IV) was monitored throughout the reaction and once IV was less than 1, hydrogenation was determined to be complete. Absorbent (Select 450, Oil-Dri Fluids Purification) was then added to remove the catalyst out of the hydrogenated cocoa butter by filtration.
  • the HCBEE was desolventized under a stream of nitrogen gas and at reduced pressure until the volatiles present in the HCBEE was below 0.5% measured by volatiles analyzer (scale-oven). Ethanol removed from the HCBEE was recovered. The desolventized HCBEE was decanted with nitrogen gas at 70°C to remove glycerol generated during the esterification. An additional glycerol wash was employed to further motivate any glycerol out of the ethyl ester phase. The decanted HCBEE was bleached by absorbent (Sorbsil 92, PQ Corporation; and Perform 6000, Oil-Dri Fluids Purification) at 95°C under agitation.
  • the bleached HCBEE was deodorized by water at 160-165°C. Finally, the deodorized HCBEE was cooled to 70°C and tocopherol (70% tocopherol in vegetable oil base, BASF Covi-Ox T70 EU (non-GM version)) was added to the cooled product.
  • Oxidative stability index measures the relative oxidative stability of fatty materials.
  • a sample of HCBEE was heated to 110°C under constant airflow. As oxidative degradation of the material began, volatile short-chain fractions broke away and were entrained in the airflow. The short-chain fractions were then trapped in distilled water and detected by a conductivity probe to provide the OSI reading.
  • Table 3 shows the OSI of HCBEE and other fatty materials. A value of OSI less than 20 hours is generally considered to be unstable.
  • HCBEE has an OSI significantly higher than other fatty acid esters and silicones, which are conventional ingredients for making personal care products.
  • the superior oxidative stability makes HCBEE a good candidate as ingredients for personal care products.
  • Table 4 shows a skin care formulation in which HCBEE is one of the ingredients. Table 4.
  • the skin care formulation has a pH adjusted to 5.0 - 5.5 and an appearance of a thick white balm. It is stable for 2 months at room temperature and at 45°C.
  • HCBEE jojoba esters (diene esters), helianthus annuus (sunflower) seed oil, tocopherol acetate, jojoba oil/macadamia seed oil esters (and) squalene (and) phytosteryl macadamiate (and) phytosterols, jojoba esters (saturated esters), poly glycerol-3 stearate, sodium stearoyl lactylate, glyceryl stearate SE, and cetearyl alcohol were mixed and heated to 75 - 80°C to obtain a Phase B mixture.
  • Phase B mixture was mixed with the Phase A mixture under homomixing agitation (3,000 - 6,000 rpm) at 75 - 80°C to obtain a Phase A/B blend.
  • the Phase A/B blend was further mixed with propellor agitation (300 - 450 rpm) and cooled to 50 - 55°C.
  • Phenoxyethanol (and) ethylhexylglycerin, and citric acid were then added to the cooled Phase A/B blend with propellor agitation (150 - 250 rpm) at 50 - 55°C. Mixing was stopped when the temperature of the final mixture reached 45 - 50°C to obtain the skin care formulation.
  • Table 6 shows a skin care formulation in which HCBEE is one of the ingredients.
  • HCBEE isononyl isononanoate
  • jojoba esters die esters
  • tocopherol acetate polyglyceryl-2 dipolyhydroxystearate
  • polyglyceryl-3 dnsotearate polyglyceryl-3 dnsotearate
  • isopropyl myristate (and) stearalkonium hectorite (and) propylene carbonate were mixed in a first vessel and heated to 65 - 70°C.
  • the mixture in the first vessel was then homogenized with homomixing agitation (2,000 - 3,000 rpm) at 65 - 70°C to obtain a Phase A mixture.
  • Zinc oxide and aluminum starch octenylsuccinate were added to the Phase A mixture with homomixing agitation (2,000 - 3,000 rpm) at 65 - 70°C to obtain a Phase A/B blend.
  • homomixing agitation 2,000 - 3,000 rpm
  • tetrasodium glutamate diacetate, glycerin, sodium chloride, caprylhydroxamic acid (and) glyceryl caprylate (and) glycerin, and citric acid were mixed with propeller agitation (300 - 450 rpm). The mixture in the second vessel was heated to 65 - 70°C to obtain a Phase C mixture.
  • Phase C mixture was added to the Phase A/B blend very slowly with homomixing agitation (2,000 - 3,000 rpm) at 65 - 70°C. Homomixing agitation was increased to a moderate speed (3,000 - 6,000 rpm) at 65 - 70°C to obtain a Phase A/B/C blend. The Phase A/B/C blend was cooled to 55 - 60°C.
  • Phase D mixture was added to the Phase A/B/C blend with homomixing agitation (3,000 - 6,000 rpm) at 55 - 60°C. Mixing was stopped when the temperature of the final mixture reached 50 - 55°C to obtain the skin care formulation.
  • the skin care formulation has a sun protection factor (SPF) of about 11.1 (without boosters), and of about 14.1 (with boosters). SPF was estimated by DSM Sunscreen Optimizer, Broad Spectrum (USA) pass.
  • Table 7 shows a skin care formulation in which HCBEE is one of the ingredients.
  • jojoba esters saturated esters
  • macadamia integrifolia seed oil zea mays (com) starch, tocopherol, perfume, and mica (and) titanium dioxide (and) iron oxides were heated to 75 - 80°C in a water bath.
  • the heated ingredients were mixed with HCBEE, which was preheated at 45 - 50°C in an oven or a water bath until a transparent homogenous phase was obtained, in a rotor stator mixer (IKA Ultra Turrax T25, S25N-25G workhead) for 1 minute at 6,000 rpm.
  • the mixture was poured into a mould.
  • the moulded mixture was set at room temperature for 5 minutes and stored in a freezer (-18°C) for 10 minutes, or set at room temperature for 30 minutes before unmolding and packing to obtain the skin care formulation.
  • Table 8 shows a skin care formulation in which HCBEE is one of the ingredients.
  • HCBEE was preheated at 45 - 50°C in an oven or a water bath until a transparent homogenous phase was obtained.
  • AQUA (part B), sodium hyaluronate, and caffeine were mixed with a stirrer (IKA Eurostar Digital, dissolver workhead) until a homogenous phase was observed to obtain a Phase D mixture.
  • Aqua (part A) and glycerin were mixed with a spatula until a homogenous phase was observed to obtain a Phase A mixture.
  • Additional aqua (part A) may be used (e.g., an extra 5 wt%) to compensate water evaporated due to the heat generated in the process.
  • Phase B mixture was mixed with the Phase A mixture for 10 minutes using a rotor/stator (IKA Ultra Turrax T25, workhead S25N-25G) at 10,000 rpm to obtain a Phase A/B blend.
  • the Phase A/B blend was heated to 65 - 75°C in a water bath.
  • Glyceryl stearate citrate and the pre-heated HCBEE were mixed and heated to 65 - 75°C in a water bath to obtain a Phase C mixture.
  • Phase C mixture was mixed with the heated Phase A/B blend with a rotor/stator (IKA Ultra Turrax T25, workhead S25N-25G) at 10,000 rpm for 2 minutes to obtain a Phase A/B/C blend.
  • the Phase A/B/C blend was cooled down to less than 40°C with stirring using a stirrer (IKA Eurostar Digital, propeller workhead).
  • Phase E mixture a Phase E mixture.
  • the Phase D mixture and the Phase E mixture were added to the Phase A/B/C blend with stirring using a stirrer (IKA Eurostar Digital, propeller workhead) until a homogenous phase was obtained.
  • Sodium hydroxide (35%) was added with stirring using a stirrer (IKA Eurostar Digital, propeller workhead) to adjust a pH of the obtained skin care formulation to 5.0 - 5.5.
  • Table 9 shows a hair care formulation in which HCBEE is one of the ingredients. Table 9. Hair Care Formulation
  • Cocos nucifera (coconut) oil and HCBEE were mixed in a separate vessle and heated to 50°C with low mixing until both ingredients were fully metled to obtain a Phase B mixture.
  • Phase B mixture was added to the Phase A mixture and mixed for 10 minutes using a scrapper mixing at 70 rpm to obtain a Phase A/B blend.
  • the Phase A mixture and the Phase B mixture could also be blended manually with a spatula, followed by a higher shear mixing under a Silverson homogenizer at 5,000 - 7,000 rpm to obtain a Phase A/B blend.
  • the Phase A/B blend was further mixed with a propeller mixer at low mixing (about 800 - 1,200 rpm) to avoid bubble entrapments.

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Abstract

La présente divulgation concerne des compositions émollientes et leur procédé de fabrication. La composition émolliente comprend un mélange d'esters d'acide gras en C1-C6 de beurre de cacao hydrogéné. Le procédé comprend les étapes suivantes : (a) la fourniture de beurre de cacao et d'alcool alkyle en C1-C6 ; (b) le mélange du beurre de cacao et de l'alcool alkyle en C1-C6 en présence d'un catalyseur d'estérification à une température d'estérification pour obtenir un mélange d'esters ; et (c) l'hydrogénation du mélange d'esters avec de l'hydrogène gazeux en présence d'un catalyseur d'hydrogénation pour obtenir les esters d'acide gras en C1-C6 de beurre de cacao hydrogéné. L'invention concerne également un produit de soins personnels comprenant la composition émolliente.
PCT/US2023/063396 2022-02-28 2023-02-28 Composition émolliente stable à l'oxydation WO2023164720A1 (fr)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6528075B1 (en) * 2001-07-27 2003-03-04 International Flora Technologies Ltd. Ultra-stable composition comprising moringa oil and it's derivatives and uses thereof
US20190127661A1 (en) * 2016-04-13 2019-05-02 Aak Ab (Publ) Odourless shea based esters
EP3517619A1 (fr) * 2016-09-23 2019-07-31 CJ Cheiljedang Corporation Procédé de préparation d'ester éthylique d'acide gras
US20190298626A1 (en) * 2016-12-16 2019-10-03 Aak Ab (Publ) Petrolatum substitution preparation

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6528075B1 (en) * 2001-07-27 2003-03-04 International Flora Technologies Ltd. Ultra-stable composition comprising moringa oil and it's derivatives and uses thereof
US20190127661A1 (en) * 2016-04-13 2019-05-02 Aak Ab (Publ) Odourless shea based esters
EP3517619A1 (fr) * 2016-09-23 2019-07-31 CJ Cheiljedang Corporation Procédé de préparation d'ester éthylique d'acide gras
US20190298626A1 (en) * 2016-12-16 2019-10-03 Aak Ab (Publ) Petrolatum substitution preparation

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
DATABASE GNPD [online] MINTEL; 22 January 2015 (2015-01-22), ANONYMOUS: "Lip Balm", XP093055187, retrieved from https://www.gnpd.com/sinatra/recordpage/2935079/ Database accession no. 2935079 *
DATABASE GNPD [online] MINTEL; 24 October 2017 (2017-10-24), ANONYMOUS: "Hydrating Precious Oil", XP093055192, retrieved from https://www.gnpd.com/sinatra/recordpage/5118967/ Database accession no. 5118967 *
DATABASE GNPD [online] MINTEL; 31 October 2012 (2012-10-31), ANONYMOUS: "Cream Stick SPF 50+", XP055665396, retrieved from https://www.gnpd.com/sinatra/recordpage/1893424/ Database accession no. 1893424 *
DATABASE GNPD [online] MINTEL; 7 July 2017 (2017-07-07), ANONYMOUS: "Clear Sunscreen Stick", XP093055191, retrieved from https://www.gnpd.com/sinatra/recordpage/4934829/ Database accession no. 4934829 *
JARI T ALANDER ED - MARIE LODEN ET AL: "Chemical and Physical Properties of Emollients", 1 January 2012, TREATMENT OF DRY SKIN SYNDROM, SPRINGER, DE, PAGE(S) 399 - 417, ISBN: 978-3-642-27605-7, XP009504324 *

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