EP1324746A1 - Formulation contenant des cires-esters - Google Patents

Formulation contenant des cires-esters

Info

Publication number
EP1324746A1
EP1324746A1 EP01976357A EP01976357A EP1324746A1 EP 1324746 A1 EP1324746 A1 EP 1324746A1 EP 01976357 A EP01976357 A EP 01976357A EP 01976357 A EP01976357 A EP 01976357A EP 1324746 A1 EP1324746 A1 EP 1324746A1
Authority
EP
European Patent Office
Prior art keywords
wax
hydrogenated
esters
ester
oil
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP01976357A
Other languages
German (de)
English (en)
French (fr)
Inventor
Georges Résidence Bois Fleury CECCHI
Jacques Margnat
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sophim
Original Assignee
Sophim
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Sophim filed Critical Sophim
Publication of EP1324746A1 publication Critical patent/EP1324746A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • A61K8/92Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • 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
    • 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
    • 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
    • A61K8/375Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
    • 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
    • A61K8/92Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/922Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02Preparations containing skin colorants, e.g. pigments
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02Preparations containing skin colorants, e.g. pigments
    • A61Q1/04Preparations containing skin colorants, e.g. pigments for lips
    • A61Q1/06Lipsticks
    • 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

Definitions

  • the present invention relates to formulations containing non-greasy emolients based on wax-esters, in particular hydrogenated wax-esters.
  • the present invention relates more particularly to the application of these formulations in the cosmetic and pharmaceutical fields.
  • the wax-esters according to the present invention are wax-esters, the constituents of which have a molecular weight of less than 600 Dalton, preferably less than 450, comprising a mixture of: several fatty acid and fatty alcohol esters originating from the interesterification by said fatty alcohol of the triglycerides of an oil of natural origin, preferably of vegetable origin, optionally followed by the hydrogenation of said esters,
  • Emolients are widely used in cosmetics and pharmacy, to make dry skin supple and to improve its elasticity.
  • the term emollient generally designates a set of perceptions transmitted by touch and by sight. Perceptions induced by touch evoke softness, elasticity and sliding power. Perceptions induced by sight evoke shine and mat.
  • emoliients offered by suppliers of cosmetic raw materials are considerable. These emolients are distinguished from each other by their chemical nature but also by the result of two quantities: emollience on application and residual emollience. There are emollients with a protective effect, others with a superfatting effect, some give the impression of a dry effect, others finally act as astringents.
  • Synthetic esters are generally made from saturated fatty acids, which gives them great stability against oxidation, but removes them from any possibility of playing a role by integration in the biosynthetic processes developing at the level of the epidermis.
  • the polyunsaturated fatty acids (linoleic and linolenic) called essential fatty acids can transform under the effect of the enzymes which the epidermis contains, into other polyunsaturated fatty acids, susceptible among other actions of limiting the transepidermal water loss.
  • This limitation of water loss guarantees the emollience of the skin, and it is this particular emollience effect which is sought in esters of natural origin, such as those which are found in oils and vegetable fats, marine oils and certain animal fats.
  • All these fatty substances are constituted by a mixture of esters which are triglycerides or triesters of glycerol and fatty acids. It is the nature of the fatty acids involved in these esters which will give its consistency to the fatty substance resulting from their mixing. Thus the more the composition of these fatty substances will be rich in saturated fatty acids and the higher their consistency will be to the point of obtaining more or less concrete fats or butters at 20 ° C. Even completely solid products are obtained at this temperature with completely hydrogenated fatty substances. Conversely, the higher the content of (mono- and poly-) unsaturated fatty acids, the more the fatty substance will tend to be completely fluid at 20 ° C.
  • jojoba oil which is naturally made of wax-esters.
  • the molecular weight of the two main constituents is 612 Dalton, which induces a slow percutaneous absorption rate.
  • this wax composed of esters of monoene fatty acids and monoene fatty alcohols means that by definition this oil does not contain essential fatty acids. Its topical application therefore does not make it possible to benefit from the effect of the latter in limiting the loss of transepidermal water, as is the case for Ceresters® in general.
  • jojoba oil containing only wax-esters to the exclusion of any mono-glyceride does not reveal emulsifying properties.
  • This process includes the following steps:
  • This process makes it possible to transform the triglycerides of fatty substances, in particular those of vegetable oils into molecules of significantly lower molecular weight, thus penetrating more easily into the epidermis.
  • Step a) consists of an alcoholysis (interesterification) of the triglycerides with a fatty alcohol, reaction giving rise to the formation of wax-esters defined chemically as esters of fatty acids and fatty alcohol.
  • the refrigeration operation is carried out in step d1) by stirring the discolored distillate, at a temperature between approximately 10 ° C and approximately 14 ° C, for a period generally at least equal to approximately 1 hour and at most equal to about 4 hours, after which the frozen product is filtered.
  • the refrigeration temperature could be reduced, but this would involve a risk that part of the waxes-esters according to the invention crystallize and then be eliminated with the residual crystallized glycerides.
  • step d1) said residual glycerides which are crystallized are saturated mono-, di- or triglycerides resulting from incomplete interesterification by said alcohol primary in step a). Their elimination makes it possible to obtain products which are completely liquid at the freezing temperature, in particular in general liquid at room temperature, that is to say at a temperature of at least 15 ° C. After step d1), there remain unsaturated residual mono-, di- and triglycerides originating from said interesterification.
  • step d1) The products obtained in step d1) are hereinafter called “non-hydrogenated wax-esters", or “cerester ®”.
  • step d2) the hydrogenation of the residue leads to products with higher melting points, generally solid at room temperature, and in general with a melting temperature of between 23 and 80 ° C. depending on the molecular weight of the products.
  • hydroxed wax-esters these products are hereinafter called “hydrogenated wax-esters" or
  • the product (residue) recovered after distillation of the residual alcohol can be hydrogenated in a reactor under a hydrogen pressure of approximately 1 to approximately 20 bar, in the presence of a catalyst such as a catalyst based on nickel or on palladium, at a temperature at least equal to approximately 100 ° C. and at most at approximately 220 ° C., for a duration generally at least equal to approximately 2 hours and at most equal to approximately 8 hours.
  • a catalyst such as a catalyst based on nickel or on palladium
  • the alcohol used in the interesterification step can in particular be chosen from C1-C22 alkanols, C3-C22 alkenols or branched C3-C22 alcohols.
  • These branched alcohols are alcohols capable of carrying C1-C8 alkyl substitutes.
  • those chosen from C4-C18 are preferably chosen, in particular those from C6-C18; among the branched alcohols in C3-C22, preference is given to those in C8-C22.
  • step a) use is made in step a) of approximately 30% by weight to approximately
  • the catalyst used to carry out the interesterification reaction is preferably an alkaline base, an alkali metal alcoholate, an alkali metal or a strong acid.
  • the catalyst is chosen from sodium hydroxide, sodium methylate, sodium metal or toluene-4 sulfonic acid.
  • the interesterification reaction is generally carried out with stirring for approximately 0.5 hour to approximately 10 hours, under an inert atmosphere, for example under a nitrogen atmosphere, and at a temperature at least equal to approximately 100 ° C. and at most equal to approximately 200 ° C.
  • the removal of the catalyst in step b), when the latter is of the alkaline type, is carried out with an excess of about 500% relative to the stoichiometric amount of a strong acid such as sulfuric acid or hydrochloric acid in aqueous solution at least N and at most 5N, necessary for the neutralization of the alkaline catalyst by stirring at room temperature for at least about half an hour and at most about one hour.
  • the catalyst neutralization operation is then followed by washes with water, with for each of said washes carried out with stirring at a temperature between approximately 80 ° C. and approximately 100 ° C., an amount of water at least equal to approximately 10% by weight and at most about 20% by weight relative to the weight of the product to be washed.
  • the distillation of the residual alcohol in the product neutralized in step c) is carried out under an absolute pressure of the order of 10 to 100 Pascal, at a temperature at least equal to approximately 65 ° C. and at most equal to approximately 230 ° C, for a period generally at most equal to approximately 4 hours and preferably equal to approximately 2 hours.
  • said distillation operation is carried out in the presence of a quantity of bleaching agent such as in particular activated carbon, at least equal to approximately 0.1% by weight and at most equal to approximately 1% by weight of the product to distilled. After complete cooling, the bleaching agent is generally separated from the distillation residue by simple filtration.
  • the product obtained in step d1) or d2) has a wax ester content (expressed as a percentage relative to the weight of the product obtained) of between approximately 55% by weight and approximately 95% by weight, preferably between approximately 66% by weight and approximately 90% by weight, and in particular still between approximately 70% by weight and approximately
  • the waxes-esters obtained consist more particularly of a mixture of:
  • the original problem underlying the present invention is to provide formulations, in particular for cosmetic use having:
  • properties of non-greasy emollients that is to say endowed with a rapid skin penetration ability, and additional characteristics consisting of a light and creamy texture and consistency on application and during spreading, skin penetration the formulation to be progressive during the spreading, and . biological properties linked to the presence of natural compounds from oil of natural origin such as unsaponifiable compounds and essential fatty acids.
  • the present invention provides a formulation comprising non-greasy emolients based on wax esters, the constituents of which have a molecular weight of less than 610 Dalton, preferably less than 450, comprising:
  • esters of fatty acids originating from the interesterification by 15. said fatty alcohol, triglycerides of an oil of natural origin preferably of vegetable origin, followed by the hydrogenation of said esters, and
  • Said formulation can therefore contain:
  • first wax-ester which is a non-hydrogenated wax-ester or cerester® and at least a second wax-ester which is a hydrogenated wax-ester or Phytowax®
  • the term “hydrogenation” or “hydrogenated” is understood here to mean that in the hydrocarbon chains, the CC unsaturations are hydrogenated, said chain then comprising only then saturated CC bonds, in particular in the hydrocarbon radical 0 corresponding to the decarboxylated residue of said fatty acid.
  • the formulation comprises at least two said hydrogenated ester waxes, the melting points of the at least two hydrogenated ester waxes being different from at least 10 ° C, and said melting points being between 23 and 75 ° C.
  • At least one said wax-ester has a melting temperature of less than 35 ° C, preferably less than 30 ° C, and at least one said hydrogenated wax-ester has a melting temperature of more than 40 ° C, preferably above 45 ° C.
  • the formulation according to the invention comprises at least a first wax-ester which is a non-hydrogenated wax-ester liquid at room temperature and at least a second wax-ester which is a solid hydrogenated wax-ester at room temperature.
  • said fatty acid and fatty alcohol esters comprise:
  • a C1 to C22 alkyl radical preferably C6 to C18, corresponding to a dehydroxylated residue of said saturated fatty alcohol
  • a C 11 to C 21 hydrocarbon radical preferably C 15 to C 21 corresponding to a decarboxylated residue of said acid.
  • a fatty alcohol which is a linear saturated fatty alcohol from C6 to C18 chosen from 1-hexanol, 1-octanol, 1-decanol, 1-dodecanol, 1-tetradecanol, 1-hexadecanol, 1-octadecanol, oleic alcohol or hexyldecanol.
  • the fatty alcohols used advantageously come from the hydrogenolysis of the methyl esters of the fatty acids obtained by fractional distillation of the hydrolysis products of vegetable oils. These fatty alcohols of vegetable origin are commercially available.
  • said hydrogenated ester waxes comprise a mixture of at least two said esters chosen from C6 to C22 alkyl stearate, C 6 to C22 alkyl palmitate, C6 to alkyl arachidate C22, and C6 to C22 alkyl hydroxystearate.
  • Stearic acid comes from the hydrogenation of oleic, linoleic and linolenic fatty acids.
  • the hydrogenation of gadoleic acid also present in vegetable oils provides arachidic acid.
  • the essential fatty acid hydrogenation product of olive oil contains mainly stearic acid (around 85%).
  • the fatty acid hydrogenation product of castor oil mainly contains 12-hydroxystearic acid (approximately 85%).
  • the formulation comprises:
  • At least one said first hydrogenated wax-ester the said hydrogenated esters of which comprise a C1 to C8 alkyl radical, preferably C6 to C8, derived from said saturated fatty alcohol, and
  • At least one said second hydrogenated wax-ester the said hydrogenated esters of which comprise a C10 to C22 alkyl radical originating from the said saturated fatty alcohol.
  • the formulation comprises: at least one said first non-hydrogenated wax-ester liquid at room temperature whose said non-hydrogenated esters comprise a C1 to C10 alkyl radical, preferably C6 to C10, and
  • At least one said second hydrogenated wax-ester the said esters of which include a C6 to C10 alkyl radical.
  • said saturated fatty alcohol used for the preparation of said esters is identical in each of said esters originating from the same so-called oil of natural origin, and is different for the different so-called wax-esters of the formulation, ie those from different oils.
  • said wax-esters comprise residual triglycerides, diglycerides and monoglycerides and unsaponifiables originating from said oil of natural origin in the following respective proportions:
  • esters possibly hydrogenated
  • Said wax-esters used in the formulation according to the invention can come in particular from olive oil, castor oil, sweet almond, hazelnut, apricot, borage, rapeseed, soybean or sunflower.
  • the latter comprises at least 3, preferably at least 5, called hydrogenated wax-esters.
  • said wax-esters are included in the oily phase of an emulsion.
  • a formulation according to the present invention may especially comprise natural waxes of the beeswax, carnauba wax, candellila wax, ozocerite, ceresin type.
  • a formulation according to the present invention can comprise from 0.5 to 15% by weight of said wax-esters.
  • the present invention also relates to a cosmetic formulation useful in particular as a care cream, foundation cream, care lotion after-shampoo, coating for coloring the lips, characterized in that it comprises a formulation according to the invention.
  • the advantage of the formulations of the present invention lies in the fact that it has structure and body, while providing softness, flux and smoothness to the application.
  • Said wax-esters having a melting point lower than about 30 ° C, that is to say lower than the body temperature bring to the formulation a smooth spreading without greasy touch, as well as a feeling of cooling on spreading.
  • Said hydrogenated ester waxes having a higher melting point than body temperature provide the formulation with a thickening effect, without spreading greasy touch while retaining a light and creamy texture. They advantageously replace all of the fatty alcohols conventionally used to give viscosity to the formulations (fatty alcohols in C14, C16 or C18) and this all the more since they limit the foaming effect.
  • said wax-esters liquid at room temperature according to the invention of vegetable origin by their manufacturing process preserve essential fatty acids which have active properties already well known elsewhere. They therefore make it possible to combine the advantages of essential fatty acids without having their disadvantage with a non-greasy feel.
  • ceresters ® may contain more or less essential fatty acids such as linoleic acid, the role of which is well known in limiting the loss of trans-epidermal water. This is the case with ceresters ® of sunflower which provide around 60% linoleic acid, without having the disadvantage of the greasy feel inherent in original sunflower oil.
  • Fully hydrogenated ester waxes were prepared from olive oil, more particularly a range of 7 products whose melting points regularly vary from 25 ° to 57 ° C. This range was obtained by alcoholysis of the olive oil (C18 fatty acids) with different fatty alcohols of vegetable origin of carbon condensation varying between 6 and 18. This gives a range of products of totally vegetable origin and whose molecular weight varies between 366 and 534 Dalton.
  • the hydrogenated wax-esters prepared are solid products at 20 ° C, of which all the essential fatty acids have been hydrogenated to stearic acid. Since olive oil consists of 85% C18 acids and 14% C16 acids, the waxes-esters resulting from its hydrogenation consist of 85% alkyl stearate, the melting point of which increases with the carbon condensation of the alcohol involved in the production of wax-esters. It is thus possible to constitute a range of products with increasing melting points, by varying the length of the alcohol.
  • the iodine index is defined as the mass in grams of iodine fixed per 100 g of sample (Standard NF ISO 3961). In fact each double bond fixes a mole of iodine (12). The value of 4 given for the iodine index is an upper limit set for the specifications and not a measurement value.
  • the acidity to which we refer does not correspond to a pH but to an acidity expressed in the Acid Index defined by the number of milligrams of potassium hydroxide necessary for the neutralization of the free fatty acids of 1 g of fatty substances (Standard NF T 60.204).
  • the saponification index is defined as the number of milligrams of potassium hydroxide necessary to saponify 1 g of fat (Standard ISO 3657: 1988 F).
  • the product obtained above is subjected to the following treatment.
  • the product being maintained under vacuum in the reaction flask, 50 ml of 2N aqueous sulfuric acid solution are added.
  • the temperature is brought to 90 ° C, stirred for 15 minutes and allowed to settle.
  • the acidic aqueous phase is drawn off, 100 ml of water are added, the mixture is stirred for 10 minutes at 90 ° C., then allowed to settle.
  • This washing with water is repeated twice, which makes it possible to achieve neutrality.
  • the product is left to settle completely, which is then completely dried under reduced pressure at 95 ° C. 960 g of product are recovered to which 2.4 g of activated carbon are added.
  • the mixture is distilled under vacuum (70 Pa) and under nitrogen sparging, gradually heating the flask so that the temperature reached by the fluid at the end of distillation does not exceed 180 ° C.
  • the vacuum during distillation is around 60 pa.
  • the distillation is stopped after 2 hours.
  • 900 g of product are recovered from the distillation flask, which are filtered on paper to separate the activated carbon. 880 g of a yellow liquid product are obtained, which reveals a slight precipitate.
  • the product obtained after hydrogenation and filtration comprises (per 100 grams of product obtained):
  • decyl hexadecanoate decyl palmitate
  • decyl eicosanoate decyl arachidate
  • * 5.5 grams of triglycerides palmitic 14.5%, stearic 85.0 % 0.5% peanut
  • * 6.1 grams of diglycerides 14.5% palmitic, 85.0% stearic, 0.5% peanut
  • * 4.1 grams of monoglycerides 14.5% palmitic, 85 stearic , 0%, peanut 0.5%).
  • Example 2 875 g of the product obtained above in 1.2. (Example 1) are introduced into a cylindrical reactor equipped with a double outer jacket allowing the passage of a cooling fluid. The liquid is gradually cooled to a temperature of 14.5 ° C, by passing the cooling fluid itself brought to 14 ° C in the jacket of said refrigeration reactor, with stirring for 4 hours, then it is filtered. 850 g of a yellow liquid are obtained, which has no marked odor, and which is perfectly clear at 15 ° C.
  • the product obtained after refrigeration and filtration comprises (per 100 grams of product obtained):
  • Example 1.3 After filtration of the catalyst, a product is obtained having a melting point of 25.0 ° C. and an index of an iodine index of less than 1.
  • the product obtained after hydrogenation and filtration comprises (per 100 grams of product obtained):
  • the residual 1-octanol is distilled under vacuum (70 Pa). The distillation is stopped after 2 hours. After cooling, the product is filtered on paper, the filtrate is hydrogenated in a stirred reactor with 1% nickel-based catalyst deposited on silica (25% nickel in the catalyst), under a pressure of 10 bar of hydrogen, at 200 ° C, for 6 hours. After filtration of the catalyst, a whitish-colored product is obtained, having a melting point of 29 ° C.
  • the product obtained after hydrogenation and filtration comprises per 100 g of product obtained:
  • Example 1.3 After filtration of the catalyst, a product is obtained having a melting point of 48 ° C. and an iodine index of less than 1.
  • the product obtained after hydrogenation and filtration comprises (per 100 grams of product obtained):
  • the residual 1-hexadecanol is distilled under vacuum (50 Pa). The distillation is stopped after 2 hours. The product is then filtered hot on paper under a nitrogen atmosphere. The filtrate is hydrogenated in a reactor stirred with 1% nickel-based catalyst deposited on silica (25% nickel in the catalyst), under a pressure of 10 bar of hydrogen, at 200 ° C for 6 hours. After filtration of the catalyst, a whitish color product is obtained, having a melting point of 56 ° C.
  • the product obtained after hydrogenation and filtration comprises per 100 g of product obtained:
  • the product obtained above undergoes the same treatment for removing the catalyst by washing with 2N sulfuric acid as the product of Example 1.2. After removing the washing water, 0.25% by weight of carbon is added to the product obtained. The product is then subjected to distillation at 230 ° C under a vacuum of 50 Pa for 2 hours. After cooling to 60 ° C, the product is filtered at this temperature on paper to remove the bleaching agent. The filtrate obtained is then hydrogenated under the same conditions as in Example 1.3. After filtration of the catalyst, a product is obtained having a melting point of 57 ° C. and an iodine index of less than 1. The product obtained after hydrogenation and filtration comprises (per 100 grams of product obtained):
  • the product obtained contains per 100 g:
  • the product obtained contains per 100 g:
  • the product obtained contains per 100 g:
  • EXAMPLE 11 Interesterification using sweet almond, sunflower, rapeseed and hazelnut oil 11.1. - 709 g of refined sweet almond oil are poured into a flask with a tube, and then 291 g of 1-octanol and 1.4 g of sodium methylate are poured. After creating a vacuum of 5000 Pa absolute, the temperature rose to 100 ° C. Upon arrival at this temperature, the vacuum is cut and the balloon atmosphere is slightly pressurized with nitrogen. The temperature of the flask is then brought to 170 ° C. and maintained at this temperature for 6 hours. The flask is then cooled to room temperature.
  • the operating mode is classic:
  • A is introduced into the stainless steel tank equipped with a turbo-emulsifier and an anchor stirring system.
  • This cream using 3 Phytowax ® shows a texture combining creaminess, softness and comfort on application.
  • Phytowax ® in C10 has a melting point close to the skin temperature, it is however too high to melt on the skin and therefore it tends to build up during application and promotes the formation of fluff.
  • Phytowax ® having a melting point lower than the body temperature, bring to the cosmetic formulation a smooth spread without greasy touch, as well as a feeling of cooling on spreading.
  • Phytowax ® in C6 in particular is particularly interesting because it gives a very characteristic softness to the spreading without greasy effect.
  • Phytowax ® having a higher melting point than body temperature, will give the cosmetic formulation a thickening effect, without touching greasy spreading. This is how Phytowax ® 16L55 and 18L57 are more particularly interesting for giving structure at room temperature, while retaining a light and creamy texture.
  • the lipstick is soft and creamy on application.
  • Phytowax ® improve mold release during manufacturing.
  • a first test consisted in replacing castor oil with a Castor Cerester ®: the test showed a marked improvement in the sensory profile of the lipstick, in terms of spreading, of slippery on application, as well than better stability at 50 °, after 24 h compared to the control.
  • the Phytowax ® having a melting point below the body temperature, used in the formulas confirmed their positive effect on the quality of the spreading of the lipstick, creamy without greasy touch, with spreading facilitated by the mixture of said Phytowax ®.

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Emergency Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Dermatology (AREA)
  • Cosmetics (AREA)
EP01976357A 2000-10-13 2001-10-04 Formulation contenant des cires-esters Withdrawn EP1324746A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR0013124 2000-10-13
FR0013124A FR2815254B1 (fr) 2000-10-13 2000-10-13 Formulation contenant un emollient non gras a base de cires-esters
PCT/FR2001/003055 WO2002030386A1 (fr) 2000-10-13 2001-10-04 Formulation contenant des cires-esters

Publications (1)

Publication Number Publication Date
EP1324746A1 true EP1324746A1 (fr) 2003-07-09

Family

ID=8855313

Family Applications (1)

Application Number Title Priority Date Filing Date
EP01976357A Withdrawn EP1324746A1 (fr) 2000-10-13 2001-10-04 Formulation contenant des cires-esters

Country Status (7)

Country Link
US (1) US20040037859A1 (ja)
EP (1) EP1324746A1 (ja)
JP (1) JP2004510804A (ja)
KR (1) KR20020063909A (ja)
AU (1) AU2001295657A1 (ja)
FR (1) FR2815254B1 (ja)
WO (1) WO2002030386A1 (ja)

Families Citing this family (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6645261B2 (en) * 2000-03-06 2003-11-11 Cargill, Inc. Triacylglycerol-based alternative to paraffin wax
US6503285B1 (en) 2001-05-11 2003-01-07 Cargill, Inc. Triacylglycerol based candle wax
US7128766B2 (en) 2001-09-25 2006-10-31 Cargill, Incorporated Triacylglycerol based wax compositions
US7192457B2 (en) 2003-05-08 2007-03-20 Cargill, Incorporated Wax and wax-based products
DE602004013166T2 (de) 2003-08-27 2009-03-19 Japan Ae Power Systems Corporation Basis für elektrisch isolierendes öl
AU2006205023C1 (en) 2005-01-10 2012-05-24 Elevance Renewable Sciences, Inc. Candle and candle wax containing metathesis and metathesis-like products
CN101563434B (zh) 2006-07-12 2012-01-25 埃莱文斯可更新科学公司 包含复分解不饱和多元醇酯蜡的热熔性胶粘剂组合物
DE102006050499A1 (de) * 2006-10-26 2008-05-08 Tischendorf, Dieter, Dr. Verfahren zum Herstellen von Thermoplasten, Kerzen oder Thermospeichermaterial
WO2008103289A1 (en) 2007-02-16 2008-08-28 Elevance Renewable Sciences, Inc. Wax compositions and methods of preparing wax compositions
MX2009013053A (es) 2007-05-30 2010-01-18 Elevance Renewable Sciences Ceras de perlas que comprenden particulas pequeñas y velas moldeadas por compresion de lados lisos elaboradas a partir de estas.
CA2690811C (en) 2007-06-15 2017-02-28 Elevance Renewable Sciences, Inc. Hybrid wax compositions for use in compression molded wax articles such as candles
FR2921266B1 (fr) * 2007-09-20 2012-06-01 Oreal Composition cosmetique de maquillage et/ou de soin comprenant au moins une cire ester et exempte d'huile apolaire
US8796217B2 (en) * 2008-01-25 2014-08-05 HallStar Italia S.r.l. Use of transesterified olive oil in the cosmetic field
FR2943243B1 (fr) * 2009-03-23 2011-06-03 Oreal Composition cosmetique comprenant une cire diester et une huile vegetale hydrogenee ester
US9382502B2 (en) 2009-10-12 2016-07-05 Elevance Renewable Sciences, Inc. Methods of refining and producing isomerized fatty acid esters and fatty acids from natural oil feedstocks
US8343468B2 (en) 2009-10-26 2013-01-01 International Flora Technologies, Ltd. Human sebum mimetics derived from botanical sources and methods for making the same
WO2011072232A1 (en) * 2009-12-11 2011-06-16 Stepan Company Liquid cleaning compositions containing sulfonated estolides and polymeric foam builders
EP2545151B1 (en) 2010-03-10 2013-12-11 Elevance Renewable Sciences, Inc. Lipid-based wax compositions substantially free of fat bloom and methods of making
WO2011143037A1 (en) 2010-05-12 2011-11-17 Elevance Renewable Sciences, Inc. Natural oil based marking compositions and their methods of making
EP2590911B1 (en) 2010-07-09 2014-05-14 Elevance Renewable Sciences, Inc. Waxes derived from metathesized natural oils and amines and methods of making
KR20140004107A (ko) 2010-11-23 2014-01-10 엘레반스 리뉴어블 사이언시즈, 인코포레이티드 실질적으로 지방 블룸이 없는 지질계 왁스 조성물 및 제조 방법
EP2729556A1 (en) 2011-07-10 2014-05-14 Elevance Renewable Sciences, Inc. Metallic soap compositions for various applications
US8916721B1 (en) * 2012-06-15 2014-12-23 Surfatech Corporation Partition coefficient ester compositions
JP5975394B2 (ja) * 2012-10-12 2016-08-23 山栄化学株式会社 毛髪化粧料
JP5975395B2 (ja) * 2012-11-09 2016-08-23 山栄化学株式会社 毛髪処理剤
CN105073198B (zh) * 2013-03-25 2019-06-04 莱雅公司 包含高熔点蜡和二氧化硅气凝胶的固体无水组合物
US20160120791A1 (en) * 2014-10-30 2016-05-05 L'oreal Anhydrous alcohol-free sunscreen composition for application onto wet or dry skin
FR3041254B1 (fr) 2015-09-22 2020-01-31 Biosynthis Ingredient cosmetique a base d'hydrocarbures satures ramifies
KR102446371B1 (ko) 2019-06-11 2022-09-22 대봉엘에스 주식회사 유지 조성물 및 이의 용도

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4131940A1 (de) * 1991-09-25 1993-04-01 Beiersdorf Ag Kosmetische und dermatologische zubereitungen
KR100298924B1 (ko) * 1994-07-21 2001-11-14 겜마 아키라 수중유형화장재료용조성물
DE19703087C2 (de) * 1997-01-29 1999-04-22 Henkel Kgaa Verwendung von PIT-Emulsionen
US5968530A (en) * 1997-10-17 1999-10-19 International Flora Technologies, Inc. Emollient compositions
US6280746B1 (en) * 1997-10-17 2001-08-28 International Flora Technologies Ltd. Dry emollient compositions
EP0910955A3 (en) * 1997-10-24 2000-03-22 Unilever N.V. Wax ester compositions
FR2788280B1 (fr) * 1999-01-08 2001-04-06 Sophim Procede de fabrication d'un emollient non gras a partir d'extraits d'olives
FR2801501B1 (fr) * 1999-11-30 2003-02-28 Oreal Composition cosmetique comprenant une cire

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO0230386A1 *

Also Published As

Publication number Publication date
FR2815254B1 (fr) 2003-02-07
WO2002030386A1 (fr) 2002-04-18
KR20020063909A (ko) 2002-08-05
AU2001295657A1 (en) 2002-04-22
JP2004510804A (ja) 2004-04-08
US20040037859A1 (en) 2004-02-26
FR2815254A1 (fr) 2002-04-19

Similar Documents

Publication Publication Date Title
EP1324746A1 (fr) Formulation contenant des cires-esters
FR2792190A1 (fr) Procede de fabrication d'un emollient non gras a base de cires-esters
EP3349720B1 (fr) Composition emolliente biosourcee comprenant des isoparaffines
EP1412462B1 (fr) Substitut de lanoline son procede d obtention et ses applications
EP3908248B1 (fr) Composition epaississante biosourcee comprenant un poly(farnésène)
WO2009056275A1 (en) Esters of glycerol and their uses in cosmetic and pharmaceutical applications
EP1507505A1 (en) Lanolin substitute based on shea butter
EP1296924A1 (fr) Procede de fabrication d'un emollient non gras a base de cires-esters
JP6905537B2 (ja) 無臭シアベースエステル
FR2788280A1 (fr) Procede de fabrication d'un emollient non gras a partir d'extraits d'olives
KR102548114B1 (ko) 초임계 이산화탄소 상에서의 에스테르교환반응을 이용한 화장품용 식물성 에스테르 유지 조성물 및 이의 제조방법
JP3681492B2 (ja) 皮膚外用剤用基剤及び皮膚外用剤
WO2023091941A1 (en) Personal care product containing natural oil-based petrolatum
CN116723823A (zh) 天然油基凡士林及其制备方法
CN116744891A (zh) 天然油基凡士林及其制备方法
WO2022207886A1 (fr) Huile concrete d'avocat enrichie en acide palmitique
EP4373458A1 (fr) Composition cosmetique sous la forme d'emulsion huile-dans-eau a forte teneur en ingredients d'origine naturelle
CN117241778A (zh) 天然油基凡士林及其制备方法
KR20230129160A (ko) 미생물로 생산된 오일을 포함하는 퍼스널 케어 조성물
CA3203702A1 (en) Natural oil-based petrolatum and method of making same
FR3113462A1 (fr) Procede de preparation de beurres
WO2022150812A1 (en) Natural oil-based petrolatum and method of making same
JP2005306888A (ja) 化粧料
CN116723824A (zh) 天然油基凡士林及其制备方法
Arct et al. New cosmetic actives containing menthol fatty acids esters-synthesis and applications

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20030411

AK Designated contracting states

Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU MC NL PT SE TR

AX Request for extension of the european patent

Extension state: AL LT LV MK RO SI

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20040501