Process for the synthesis of bio-sourced solid fatty substances

Abstract

The invention relates to a process for preparing a mixture of linear alkanes of natural origin, preferably of plant origin, comprising the steps of: Metathesis of at least one terminal linear olefin, comprising between 5 and 24 carbon atoms, derived from at least one fatty acid or fatty acid ester of natural origin, preferably of plant origin, in the presence of a non-isomerizing olefin metathesis catalyst, whereby a first mixture of internal olefins (I) is obtained; Isomerizing metathesis of the mixture of internal olefins (I) obtained in step i) in the presence of a catalyst or a mixture of catalysts, whereby a second mixture of internal olefins (II) is obtained, and Hydrogenation of the mixture of internal olefins (II) in the presence of a catalyst, whereby a mixture (III) of linear alkanes of natural origin is obtained.

Description

Title of the invention: Process for the synthesis of bio-sourced solid fatty substances Technical field

[0001] The present description relates to a process for preparing a mixture of linear alkanes of natural origin, in particular of plant origin, in the form of a solid fatty substance, in particular a wax or a pasty mixture. It also relates to the mixtures of linear alkanes capable of being obtained by this process and their use in the fields of cosmetics, pharmaceuticals, coatings, inks, varnishes, paper, adhesives, candles, plastics, rubbers and / or food products. Prior art

[0002] Paraffins, also called mineral waxes, are hydrocarbon compounds derived from petroleum refining. Consisting of different alkanes, with a wide range of chain lengths between 18 and 60 carbon atoms, paraffins are substances with a solid to semi-solid consistency at room temperature. They are generally characterized by a melting point between 40 and 90°C, excellent stability to oxidation and temperature, olfactory neutrality and clarity.

[0003] Synthetic waxes are synthetic products obtained from petroleum derivatives. These include polymers or silicone waxes, which generally have a high melting point.

[0004] These properties make them highly sought-after products for many applications such as the manufacture of matches, candles, papers, adhesives, paints, pharmaceuticals and cosmetics.

[0005] However, the mineral and synthetic waxes or paraffins currently available on the market pose problems in terms of environmental friendliness and safety.

[0006] Indeed, mineral paraffins, including MOSH (mineral oil saturated hydrocarbons) and / or MOAH (mineral oil aromatic hydrocarbons) are suspected of toxicity, in particular of carcinogenic effect, so that regulations now require limiting their concentration in food products.

[0007] Furthermore, due to their origin, mineral paraffins contribute negatively to the increase in anthropogenic carbon dioxide. In addition, they are not biodegradable and induce bioaccumulation in the environment.

[0008] This is why many sectors are looking for ecological, biodegradable and sustainable substitute products to replace mineral and synthetic paraffins.

[0009] So-called natural waxes, of plant or animal origin, such as beeswax, candelilla wax or carnauba wax, offer a renewable alternative to mineral paraffins.

[0010] However, in many applications, natural waxes cannot completely replace mineral or synthetic paraffins.

[0011] Scientific work has recently investigated the possibility of substituting, in lipstick formulations, mineral paraffins with mixtures of lipids of natural origin, in this case a mixture of linear C35-C38 alkenones, derived from algal resources. However, low stabilities have been observed (Huynh, A. et al. Evaluation of alkenones, a renewably sourced, plant-derived wax as a structuring agent for lipsticks. Int. J. Cosmet. Sci. 42, 146-155 (2020)).

[0012] Other scientific work has recently shown that in the field of lipsticks, the substitution of synthetic waxes of petroleum origin by waxes of plant origin poses problems of stability of the product, strength of the lipstick, exudation, incompatibilities and / or oxidation, with which increasingly demanding consumers are not ready to deal, (de Clermont-Gallerande et al. Substitution of synthetic waxes by plant-based waxes in lipsticks, OCL, 2022, 29, 19).

[0013] Thus, this study shows that when the composition obtained with vegetable waxes is solid, it has hardness values ​​that are too low, which results in breakages during application that are too frequent in the case of sticks.

[0014] Furthermore, the stabilities over time are not satisfactory. This can result in the appearance of a phenomenon of exudation, polymorphism, a change in the appearance of the surface of the product: appearance of inhomogeneities in appearance, with the presence of matt surface area(s), or film-coated area(s), or even by a change in the sensoriality upon application over time (reduction in melting, slipperiness).

[0015] Furthermore, natural vegetable waxes which have a high melting point, i.e. around 80°C, do not allow sufficiently sensory textures to be obtained: they are very rigid, lack flexibility and the sensation when applied to the skin or lips is unpleasant. Finally, vegetable waxes with a melting point below 80°C do not allow the composition to be structured sufficiently to mold lipsticks into sticks.

[0016] There is therefore a real need to find substitute products of natural origin, particularly plant-based, ecological and sustainable to replace mineral paraffins. Summary

[0017] A process has now been developed for preparing a mixture of linear alkanes of natural origin, in particular vegetable origin, in the form of a solid fatty body, the physicochemical characteristics of which, in particular the hardness, the texture, and / or the melting point are very close to those of existing mineral paraffins.

[0018] Thus, according to a first aspect, the invention relates to a process for preparing a mixture of linear alkanes of natural origin, preferably of plant origin, comprising the steps of: i. Metathesis of at least one terminal linear olefin, comprising between 5 and 24 carbon atoms, derived from at least one fatty acid or fatty acid ester of natural origin, preferably of plant origin, in the presence of a non-isomerizing olefin metathesis catalyst, whereby a first mixture of internal olefins (I) is obtained; ii. Isomerizing metathesis of the mixture of internal olefins (I) obtained in step i) in the presence of a catalyst or a mixture of catalysts, whereby a second mixture of internal olefins (II) is obtained, and iii. Hydrogenation of the mixture of internal olefins (II) in the presence of a catalyst, whereby a mixture (III) of linear alkanes of natural origin is obtained.

[0019] Surprisingly, the inventors were able to observe that the process made it possible to obtain, in a very reproducible manner and with good yields, mixtures of linear alkanes characterized by a very controlled distribution of chain lengths.

[0020] Then, very advantageously, the inventors were able to show that by varying the composition of the starting mixture of terminal olefins, in particular the chain length of these olefins, and / or their relative proportion within the mixture, the process made it possible to control this distribution and therefore the physicochemical characteristics of the mixture obtained, in particular the melting point of the mixture obtained. Thus, starting from an equimolar mixture of terminal olefins, the process makes it possible to obtain an alkane mixture having a symmetrical chain length distribution, i.e. a Gaussian distribution. Furthermore, the inventors were able to observe that the greater the proportion of short chain within the starting mixture of terminal olefins, the more the Gaussian distribution will shift towards smaller alkane chains (positive asymmetric distribution). Conversely, the more the The greater the proportion of long chains in the mixture, the more the Gaussian distribution will shift towards larger alkane chains (negatively skewed distribution).

[0021] Very advantageously, the process thus makes it possible to access mixtures of linear alkanes of natural origin having a melting point which can vary to a large extent, in particular from 31.5°C to 90°C measured by differential scanning calorimetry (DSC). These mixtures can in particular be in the form of a wax or a pasty compound.

[0022] According to another aspect, the invention relates to a mixture of linear alkanes of natural origin, in particular of plant origin, said mixture being capable of being obtained according to the process of the invention.

[0023] According to another aspect, the invention relates to a mixture of linear alkanes of natural origin, in particular of plant origin, in particular in the form of a solid fatty substance, in which: - each linear alkane constituting the mixture contains between 10 and 70 carbon atoms, and - the distribution of the numbers of each linear alkane, arranged by increasing number of carbon atoms, is: • increasing between the linear alkane having the number of atoms of smallest carbon up to the mode of distribution; and • decreasing between the distribution mode and the linear alkane with the largest carbon number, • the numbers being calculated as a percentage by weight relative to the total weight of the mixture of linear alkanes of natural origin.

[0024] In a particularly advantageous manner, the inventors were able in particular to develop a mixture of linear C24 to C60 alkanes of natural origin, in the form of a wax, having physicochemical characteristics very close to those of a synthetic mineral wax, commonly used in the field of lipsticks. In particular, the inventors were able to show that the wax obtained according to the process is compatible with the oils commonly used in the field of cosmetics and that it makes it possible to obtain lipsticks having a texture, hardness and stability comparable to those obtained for a lipstick including mineral paraffins used in the field.

[0025] More generally, these mixtures of linear alkanes make it possible in particular to obtain compositions, in particular anhydrous and solid, and more particularly in stick form, whose physicochemical properties are similar to those obtained with analogous compositions prepared from mineral wax(es) in terms of hardness, sensoriality and stability over time while being devoid of of mineral and / or synthetic waxes. They also make it possible to obtain mascara compositions (emulsions of waxes in water) which provide volume to the eyelashes similar to that obtained with similar compositions prepared from mineral wax(es) while being free of mineral and / or synthetic waxes.

[0026] According to yet another aspect, the invention relates to a composition comprising a mixture of linear alkanes according to the invention.

[0027] According to yet another aspect, the invention relates to the use of a mixture of linear alkanes according to the invention, in the field of cosmetics, pharmaceuticals, coatings, inks, varnishes, paper, adhesives, candles, plastics, rubbers and / or food products.

[0028] The features set out in the following paragraphs may, optionally, be implemented independently of one another or in combination with one another.

[0029] The method according to the invention may include the following additional characteristics: - the non-isomerizing olefin metathesis catalyst in step i) is chosen from transition metal complexes, in particular transition metal alkylidenes, in particular ruthenium; - the non-isomerizing olefin metathesis catalyst is chosen from Ru-la, Ru-lb or a mixture thereof;

[0030] [Chem.l] N- Ru-la

[0031] [Chem.2] PCy, Ru-lb the catalyst or mixture of catalysts used in step ii) is a transition metal complex, in particular ruthenium; the olefin isomerizing metathesis catalyst is a mixture of Ru-2 and Ru-3

[0032] [Chem.3] Ru-2

[0033] [Chem.4] Ru-\O c / ! R O--C \.....N' CFs HSC.....< H CH3 Ru-3 - the terminal olefins used in step i) are prepared from fatty acid esters derived from jojoba oil; - said at least one terminal linear olefin used in step i) is a mixture of at least two distinct terminal linear olefins each comprising between 5 and 24 carbon atoms, in particular between 16 and 24 carbon atoms, preferably between 16 and 20 carbon atoms; - said at least two terminal linear olefins differ from each other by a number of carbon atoms of at least two; - said at least one terminal linear olefin used in step i) is a mixture of three terminal linear olefins, preferably C6 / C7 / C8, C8 / C9 / C10, C10 / C12 / C14, or C16 / C18 / C20, this mixture being able in particular to comprise: - From 1 to 10% by weight of C16 terminal olefins; - From 45 to 49.5% of terminal olefins in Cl8; and - From 45 to 49.5% of C20 terminal olefins;

[0034] The percentages being expressed by weight relative to the total weight of the mixture of terminal olefins.

[0035] The mixture of linear alkanes of natural origin according to the invention capable of being obtained according to the process of the invention may comprise at least two alkanes distinct linear alkanes, said at least two distinct linear alkanes each comprising between 10 and 70 carbon atoms, preferably between 24 and 60 carbon atoms.

[0036] The mixture of linear alkanes of natural origin, in particular of plant origin, in particular in the form of a solid fatty body, according to the invention may further comprise one or more of the following additional characteristics: - each linear alkane in the distribution differs by a number of carbon atoms equal to one, from the consecutive linear alkane in the distribution; - each linear alkane constituting the mixture contains between 24 and 60 carbon atoms; - the distribution mode is between 40 and 45 carbon atoms; - the median of the distribution is between 40 and 45 atoms of carbons; - the mixture has a melting point between 75 and 85°C; - each linear alkane constituting the mixture comprises between:

[0037] - 17 and 44 carbon atoms;

[0038] - 22 and 54 carbon atoms; or

[0039] - 12 and 47 carbon atoms; or

[0040] - 11 and 50 carbon atoms; or

[0041] - 11 and 54 carbon atoms.

[0042] The composition comprising a mixture of linear alkanes according to the invention may further comprise and / or be characterized by one or more of the following additional characteristics: - comprise less than 3% by weight, in particular less than 1% by weight, preferably free of solid fatty substances of mineral and / or synthetic origin, the percentages by weight being expressed relative to the total weight of the composition; - characterized in that it is a cosmetic or pharmaceutical composition, the cosmetic composition being able to be in particular a perfuming, care or makeup product for the skin, mucous membranes or appendages; - characterized in that it is an anhydrous composition; - characterized in that it is a solid composition; - characterized in that it is a solid composition in the form of stick ; - characterized in that it is a mascara composition. Brief description of the drawings

[0043] Other characteristics, details and advantages will appear on reading the detailed description below, and on analyzing the attached drawings, in which:

[0044] [Fig.l]

[0045] [Fig.l] schematically represents the process according to the invention, which corresponds to a targeted sequential catalytic process leading to a mixture of alkanes from terminal olefins. The reaction conditions are as follows: (i) metathesis: Ru-1a / Ru-1b 3 / 7 (0.3 mol%), THF (9M), 75°C, 2 days; (ii) isomerization / metathesis: Ru-2 (0.5 mol%), Ru-3 (1 mol%), MeOH (100eq / cat), THF (1.3M), 75°C, 2h; (iii) hydrogenation: H2 (1 bar), Pd / C (0.4% wt Pd / substrate), cyclohexane (0.2g / mL), 50°C, 16h.

[0046] [Fig.2]

[0047] [Fig.2] schematically represents a process for obtaining a mixture terminal olefins from esters of saturated and unsaturated fatty acids.

[0048] [Fig.3]

[0049] [Fig.3] schematically represents an example of a method of obtaining of terminal olefins of Cl6, Cl8 and C20, respectively. The reaction conditions are as follows: preparation of the grignard reagent: Alkyl bromide (1.5 eq), Mg (3 eq), I2 (0.1 mol%), THF (1.3M), 0°C to 20°C, 1h; cross-coupling: CuCl2 (2 mol%), 1-phenylpropyne (10 mol%), THF (0.9M), 0°C to 20°C, 1.5h; Yields: C16 (1.7g; 77%); C18 (2.3g, 90%; 63.5g, 91%); C20 (9.9g, 99%; 69.5g, 99%).

[0050] [Fig.4]

[0051] [Fig.4] represents the cross metathesis step according to step i) of the method of the invention, from a specific mixture of linear terminal olefins in C16, C18 and C20, according to example 1. The reaction conditions are as follows: starting terminal olefins: C16 (0.01 eq), C18 (0.495 eq), C20 (0.495 eq); metathesis: Ru-1a / Ru-1b 3 / 7 (0.3 mol%), THF (9M), 75°C, 2 days.

[0052] [Fig.5]

[0053] [Fig.5] represents the isomerizing metathesis step according to step ii) of the process of the invention, from a specific mixture of terminal linear olefins in C16, C18 and C20, used in step i). The reaction conditions are as follows: Ru-2 (0.5 mol%), Ru-3 (1 mol%), MeOH (100eq / cat), THF (1.3M), 75°C, 2h

[0054] [Fig.6]

[0055] [Fig.6] represents the CPG analysis of the internal olefin mixture obtained in step ii) of example 1 from a specific mixture of terminal linear olefins of C16, C18 and C20, used in step i), according to example 1.

[0056] [Fig.7]

[0057] [Fig.7] represents the hydrogenation step according to step iii) of the process according to the invention. The reaction conditions are as follows: H2 (1 bar), Pd / C (0.4% wt Pd / substrate), cyclohexane (0.2g / mL), 50°C, 15h.

[0058] [Fig.8]

[0059] [Fig.8] represents the GC analysis of the mixture of linear alkanes obtained in step iii) from a specific mixture of terminal linear olefins of C16, C18 and C20, used in step i), according to example 1.

[0060] [Fig.9]

[0061] [Fig.9] schematically represents the ethenolysis reaction of oil of jojoba leading to dec-l-ene, according to example 2. The reaction conditions are as follows: ethenolysis: ethylene (10 bar), Ru-4 (100 ppm), 40°C, 6h.

[0062] [Fig. 10]

[0063] [Fig. 10] represents the process of the invention from dec-l-ene according to example 2: (i) metathesis: Ru-la / Ru-lb 3 / 7 (0.3 mol%), THF (IM), 75°C, 4 days; (ii) isomerization / metathesis: Ru-2 (0.5 mol%), Ru-3 (1 mol%), MeOH (100eq / cat), THF (0.7M), 75°C, 2h; (iii) hydrogenation: H2 (1 bar), Pd / C (0.4% wt Pd / substrate), cyclohexane (0.2g / mL), 50°C, 6h.

[0064] [Fig. 11]

[0065] [Fig. 11] represents the GC analysis of the mixture of linear alkanes obtained in step iii) from dec-l-ene implemented in step i), according to example 2.

[0066] [Fig. 12]

[0067] [Fig. 12] represents the GC analysis of the mixture of linear alkanes obtained in step iii) from a specific mixture of terminal linear olefins in C16, C18 and C20 (Ci6 (0.01 eq), C18 (0.495 eq), C2o (0.495 eq)) used in step i), according to example 3.

[0068] [Fig. 13]

[0069] [Fig. 13] represents the GC analysis of the mixture of linear alkanes obtained in step iii) from a specific mixture of terminal linear olefins in C6, C7 and C8 (C6 (0.33 eq), C7 (0.33 eq), C8 (0.33 eq)) according to example 4.

[0070] [Fig. 14]

[0071] [Fig.14] represents the GC analysis of the mixture of linear alkanes obtained in step iii) from a specific mixture of terminal linear olefins in C8, C9 and CIO (C8 (0.33 eq), C9 (0.33 eq), Cio (0.33 eq)) according to example 5.

[0072] [Fig.15]

[0073] [Fig.15] represents the CPG analysis of the mixture of linear alkanes obtained in step iii) from a specific mixture of terminal linear olefins of C10, C12 and C14 (C10 (0.33 eq), C12 (0.33 eq), C14 (0.33 eq)) according to example 6. Detailed description

[0074] The invention is now described in more detail and in a non-limiting manner in the following description.

[0075] Unless otherwise indicated, all percentages relating to quantities are percentages by mass.

[0076] For the purposes of this description, the term "mineral wax" means a refined or semi-refined product obtained from the processing and refining of crude oil, mainly consisting of saturated hydrocarbons. This includes, in particular, a paraffin or a microcrystalline wax.

[0077] For the purposes of this description, the term "synthetic wax" means a wax whose synthesis is carried out from hydrocarbons derived from petroleum refining. These are mainly polymers of fossil (petrochemical) origin. For example, mention may be made of polyolefin waxes synthesized from the polymerization of ethylene (polyethylene wax), propylene (propylene wax) and other monomers of fossil origin.

[0078] For the purposes of the present description, the term "terminal linear olefin" means a linear hydrocarbon chain comprising in particular from 5 to 24 carbon atoms and one or two double bonds at the end of the hydrocarbon chain ((-CH=CH2)). Thus, the terminal linear olefin is an alpha-olefin having the formula (Cn iH2n i +[ )CH=CH2 or CH2=CH(Cn2H2n2)CH=CH2 where ni is an integer between 4 and 22 and n2 is an integer between 1 and 5.

[0079] By "linear alkanes of natural origin" is meant, within the meaning of the present description, alkanes which have been obtained from biomass, and in particular from plants, and which therefore comprise carbon of renewable origin.

[0080] Unlike ingredients derived from fossil materials, ingredients derived from renewable raw materials contain 14C. All carbon samples taken from living organisms (animals or plants) are in fact a mixture of 3 isotopes: 12C (representing ~ 98.892%), 13C (~ 1.108%) and 14C (traces: 1.2.10 12%). The 14C / 12C ratio of living tissues is identical to that of the atmosphere. In the environment, 14C exists in two predominant forms: in mineral form, i.e., carbon dioxide (CO2), and in organic form, i.e., carbon integrated into organic molecules.

[0081] In a living organism, the 14C / 12C ratio is kept constant by metabolism because carbon is continually exchanged with the environment. Since the proportion of 14C is constant in the atmosphere, it is the same in the organism, as long as it is alive, since it absorbs this 14C as it absorbs 12C. The average ratio of 14C / 12C is equal to 1.2x10 12.

[0082] 12C is stable, meaning that the number of 12C atoms in a given sample is constant over time. 14C is radioactive (each gram of carbon in a living being contains enough of the 14C isotope to produce 13.6 disintegrations per minute) and the number of such atoms in a sample decreases over time (t) according to the law:

[0083] n = no exp(-at)

[0084] in which:

[0085] - no is the number of 14C at the origin (at the death of the creature, animal or plant),

[0086] - n is the number of 14C atoms remaining at the end of time t,

[0087] - a is the decay constant (or radioactive constant); it is related to the half-life.

[0088] The half-life (or period) is the time at the end of which any number of radioactive nuclei or unstable particles of a given species is reduced by half by disintegration; the half-life Ti / 2 is related to the disintegration constant a by the formula aTi / 2 = In 2. The half-life of 14C is 5730 years.

[0089] Taking into account the half-life (Ti / 2) of 14C, it is considered that the 14C content is constant from the extraction of the animal or plant raw materials until the manufacture of the formulation, and even until the end of its use.

[0090] The applicant considers that the mixture of linear alkanes is of natural origin, that is to say derived from renewable raw materials if it contains at least 20% by mass of C of renewable origin on the total mass of carbon, preferably at least 50% by mass of C of renewable origin on the total mass of carbon, more preferably at least 80% by mass of C of renewable origin on the total mass of carbon, even more preferably at least 90% by mass of C of renewable origin on the total mass of carbon, this percentage being preferably measured according to the ASTM D 6866 standard.

[0091] In other words, an alkane is derived from renewable raw materials if it contains at least 0.2.10 10% by mass of 14C, preferably 0.6.10 10% by mass of 14C.

[0092] Currently, there are at least two different techniques for measuring the 14C content of a sample:

[0093] - By liquid scintillation spectrometry: This method consists of counting 'Beta' particles from the decay of 14C: The Beta radiation from a sample of known mass (known number of 12C atoms) is measured over a certain time. This 'radioactivity' is proportional to the number of 14C atoms, which can thus be determined. The 14C present in the sample emits B- radiation, which, when in contact with the scintillating liquid (scintillator), gives rise to photons. These photons have different energies (between 0 and 156 Kev) and form this which is called a 14C spectrum. According to two variants of this method, the analysis is carried out either on the CO2 previously produced by the carbon sample in a suitable absorbent solution, or on the benzene after prior conversion of the carbon sample into benzene.

[0094] - By mass spectrometry: The sample is reduced to graphite or gaseous CO2, analyzed in a mass spectrometer. This technique uses an accelerator and a mass spectrometer to separate the 14C ions from the 12C and thus determine the ratio of the two isotopes.

[0095] All these methods for measuring the 14C content of materials are described precisely in the ASTM D 6866 standards (in particular D6866-06) and in the ASTMD 7026 standards (in particular 7026-04). These methods measure the 14C / C ratio of a sample and compare it with the C / C ratio of a reference sample of 100% renewable origin, to give a relative percentage of C of renewable origin in the sample.

[0096] The measurement method preferably used in the case of the mixture of linear alkanes of the invention is mass spectrometry described in standard ASTM D6866-06 (“accelerator mass spectroscopy”).

[0097] For the purposes of the present invention, the term "fatty substance" means any oily organic substance comprising at least one carbon chain comprising at least 11 carbon atoms, and whose solubility in water at 25°C (1 atm) is less than 0.1% by weight.

[0098] The “solid fatty bodies” preferably have a melting point greater than or equal to 35°C and / or have a viscosity at a temperature of 40°C and under a shear rate of 1 S1, greater than or equal to 1 Pa.s., in particular ranging from 1 Pa.s to 1,000,000 Pa.s and preferably from 10 to 1,000 Pa.s. The viscosity measurements can be carried out at a temperature of approximately 40°C, on a Carri-Med CSL2-500.

[0099] The solid fatty substances according to the invention may be crystallized, amorphous or pasty. The melting point preferably ranges from 35 to 250°C and more particularly from 40 to 150°C. The melting points may be measured by differential scanning calorimetry (DSC), in particular with a temperature rise rate of 10°C / min. The melting point is then the temperature corresponding to the peak of the endothermic melting peak obtained during the measurement.

[0100] The solid fatty substance according to the invention may in particular be a wax or a pasty fatty substance.

[0101] A “wax”, within the meaning of the present invention, is a lipophilic compound, solid at room temperature (approximately 25°C), with a reversible solid / liquid state change, having a melting temperature greater than approximately 40°C and up to 200°C, and having an anisotropic crystalline organization in the solid state. Generally speaking, the size of the wax crystals is such that the crystals diffract and / or diffuse light, giving the composition containing them a more or less opaque cloudy appearance. By bringing the wax to its melting temperature, it is possible to make it miscible with the oils and to form a microscopically homogeneous mixture, but by bringing the temperature of the mixture back to room temperature, a recrystallization of the wax in the oils of the mixture is obtained, detectable microscopically and macroscopically (opalescence). On the definition of waxes, we can cite for example PD Dorgan, Drug and Cosmetic Industry, December 1983, pp. 30-33.

[0102] For the purposes of the present invention, the term "pasty fatty body" means a lipophilic fatty compound with a reversible solid / liquid state change having an anisotropic crystalline organization in the solid state, and comprising at a temperature of 23°C a liquid fraction and a solid fraction.

[0103] In other words, the starting melting temperature of the pasty fatty substance may be less than 23°C. The liquid fraction of the pasty fatty substance measured at 23°C may represent 9 to 97% by weight of the pasty fatty substance. This liquid fraction at 23°C preferably represents between 15 and 85%, more preferably between 40 and 85% by weight.

[0104] For the purposes of the invention, the melting temperature corresponds to the temperature of the most endothermic peak observed in thermal analysis (DSC) as described in standard ISO 11357-3; 1999. The melting point of a pasty fatty substance can be measured using a differential scanning calorimeter (DSC), for example the calorimeter sold under the name “MDSC 2920” by the company TA Instruments.

[0105] The measurement protocol is as follows:

[0106] A 5 mg sample of pasty fatty substance placed in a crucible is subjected to a first temperature rise ranging from - 20 °C to 100 °C, at a heating rate of 10 °C / minute, then is cooled from 100 °C to - 20 °C at a cooling rate of 10 °C / minute and finally subjected to a second temperature rise ranging from - 20 °C to 100 °C at a heating rate of 5 °C / minute. During the second temperature rise, the variation in the difference in power absorbed by the empty crucible and by the crucible containing the sample of pasty fatty substance as a function of the temperature is measured. The melting point of the pasty fatty substance is the temperature value corresponding to the top of the peak of the curve representing the variation in the difference in power absorbed as a function of the temperature.

[0107] The liquid fraction by weight of the pasty fatty substance at 23°C is equal to the ratio of the enthalpy of fusion consumed at 23°C to the enthalpy of fusion of the pasty fatty substance. The enthalpy of fusion of the pasty fatty substance is the enthalpy consumed by the latter to pass from the solid state to the liquid state. The pasty fatty substance is said to be in the solid state when its entire mass is in solid crystalline form. The pasty fat is said to be in the liquid state when its entire mass is in liquid form.

[0108] The enthalpy of fusion of the pasty fatty body is equal to the temperature under the curve of the thermogram obtained using a differential scanning calorimeter (DS C), such as the calorimeter sold under the name MDSC 2920 by the company TA instrument, with a temperature rise of 5 or 10 °C per minute, according to the ISO 11357-3:1999 standard.

[0109] The enthalpy of fusion of the pasty fatty substance is the quantity of energy required to change the pasty fatty substance from the solid state to the liquid state. It is expressed in J / g.

[0110] The enthalpy of fusion consumed at 23°C is the quantity of energy absorbed by the sample to pass from the solid state to the state it presents at 23°C consisting of a liquid fraction and a solid fraction.

[0111] The liquid fraction of the pasty fatty substance measured at 32°C preferably represents from 30 to 100% by weight of the pasty fatty substance, preferably from 50 to 100%, more preferably from 60 to 100% by weight of the pasty fatty substance. When the liquid fraction of the pasty fatty substance measured at 32°C is equal to 100%, the temperature at the end of the melting range of the pasty fatty substance is less than or equal to 32°C.

[0112] The liquid fraction of the pasty fatty substance measured at 32°C is equal to the ratio of the enthalpy of fusion consumed at 32°C to the enthalpy of fusion of the pasty fatty substance. The enthalpy of fusion consumed at 32°C is calculated in the same way as the enthalpy of fusion consumed at 23°C.

[0113] The olefin metathesis reaction is a well-known reaction in organic chemistry. This reaction, which takes place in the presence of an appropriate catalytic system, consists of the exchange of alkylidene groups between two olefins according to the following equations:

[0114] 1. First case, called "self metathesis" or "homometathesis" (that is to say metathesis of an olefin molecule on a molecule of the same olefin):

[0115] [Chem.5]

[0116] 2. Second case, called "cross-metathesis" (i.e. metathesis between two different olefins):

[0117] [Chem.6] RK,R2 c=c R\ R3 CC H 'm R2y R4 RA H' H c=cz 'R4 HH Jc=c' 4 r3 'R»

[0118] The olefin metathesis reaction is a balanced reaction. It can occur in the presence of a wide variety of catalysts, most often based on transition metals from groups IVA to VIII, including tungsten, molybdenum, rhenium and ruthenium, either in homogeneous phase or in heterogeneous phase.

[0119] By "isomerizing metathesis" is meant an olefin metathesis reaction which takes place in the presence of metal hydrides resulting either a) from the intrinsic decomposition of the metathesis catalyst or b) from a metal hydride catalyst added to the reaction medium; the action of which is to isomerize the double bond(s) present in the starting compound and / or in the product resulting from the metathesis reaction.

[0120] A “distribution” is generally a function that associates a frequency of occurrence with a class of values. In this case, as used in the present description, this term refers to the distribution of the chain lengths of the linear alkanes constituting the mixture obtained by the process, or in other words, to the distribution of the number of carbon atoms of the linear alkanes constituting this mixture. Thus, each linear alkane of the mixture is associated with its number, in particular with its percentage by weight relative to the total weight of the mixture. The analysis of this distribution can in particular be carried out by means of gas chromatography (GC), possibly coupled with mass spectrometry (GC-MS).

[0121] This distribution is characterized in particular by the central values, namely the mode, the median and the mean.

[0122] The mode or dominant value corresponds to the most frequent value in the distribution. In this case, it corresponds to the linear alkane most represented in the mixture, and therefore for which the weight content in the mixture is maximum.

[0123] Since the chain lengths are classified in ascending order, the median corresponds to the chain length which divides the number into two equal subsets: 50% of the alkanes have chain lengths greater than the median, and 50% take lower values.

[0124] The average corresponds to the sum of the values ​​divided by the number of elements.

[0125] When these three central values ​​are combined (mode = mean = median), the distribution is called normal or Gaussian. The graphical representation of this distribution forms a bell-shaped curve, symmetrical with respect to the mean.

[0126] This distribution can also present an asymmetry, positive or negative.

[0127] When the distribution is positively skewed, the tail of the distribution extends further towards the upper side of the mean. In other words, there are more extreme values ​​on the upper side of the mean. The tail on the lower side is shorter.

[0128] Conversely, when the distribution is negatively skewed, the tail of the distribution is longer on the lower side of the values ​​relative to the mean. There are more extreme values ​​on the lower side, and the tail on the upper side is shorter.

[0129] These types of asymmetric distributions are characterized by a measure called skewness, which quantifies the degree of asymmetry. A zero skew corresponds to a perfectly symmetric distribution, while a positive or negative skew indicates asymmetry on the respective side.

[0130] Process for the preparation of a mixture of linear alkanes of natural origin

[0131] According to a first aspect, the invention relates to a process for preparing a mixture of linear alkanes of natural origin, preferably of plant origin, comprising the steps of: i. Metathesis of at least one terminal linear olefin comprising between 5 and 24 carbon atoms, derived from at least one fatty acid or fatty acid ester of natural origin, preferably of plant origin, in the presence of a non-isomerizing olefin metathesis catalyst, whereby a first mixture of internal olefins (I) is obtained; ii. Isomerizing metathesis of the mixture of internal olefins (I) obtained in step i) in the presence of a catalyst or a mixture of catalysts, whereby a second mixture of internal olefins (II) is obtained, and iii. Hydrogenation of the mixture of internal olefins (II) in the presence of a hydrogenation catalyst, whereby a mixture (III) of linear alkanes of natural origin is obtained.

[0132] Step i) of metathesis

[0133] The non-isomerizing olefin metathesis catalyst in step i) may consist of a single catalyst or a mixture of non-isomerizing olefin metathesis catalysts. It may in particular be chosen from transition metal complexes, in particular transition metal alkylidenes, in particular ruthenium, or mixtures thereof.

[0134] Preferably, the ruthenium catalyst is chosen from [Ru-la], [Ru-lb] or a mixture thereof. The catalyst may in particular be used in the form of a mixture of Ru-la and Ru-lb, in particular in a Ru-la / Ru-lb weight ratio of between 1 and 2, in particular 3 / 7.

[0135] [Chem.l] Ru-la

[0136] Ru-la has the chemical formula: C5iH58C12N4Ru and the molecular mass: 899.02 g.mol '.

[0137] [Chem.2] I PCy3 Ru-lb

[0138] Ru-lb has the chemical formula: C33H34C12N2Ru and the molecular mass: 630.62 g.mol-1.

[0139] The amount of catalyst can vary between 0.01 and 1.0 mol%, in particular between 0.1 and 0.5 mol% relative to the mixture of terminal linear olefins used in step i).

[0140] Step i) is in particular carried out at a temperature between 70°C and 90°C, under an inert atmosphere. It is in particular carried out in a polar and aprotic solvent, for example THF.

[0141] The mixture may be stirred until the at least one terminal olefin is completely converted, which may be monitored by proton NMR. The mixture may thus be stirred until the terminal olefin protons have completely disappeared, for example for 1 to 3 days, in particular for two days.

[0142] At the end of step i), the catalyst can be neutralized, in particular by adding an alkyl vinyl ether to the reaction mixture.

[0143] Preferably, the metathesis catalyst is removed, for example by silica gel chromatography and / or by filtration.

[0144] Step ü) of isomerizing metathesis of olefins

[0145] The isomerizing metathesis step can be carried out in the presence of a single catalyst or a mixture of at least two catalysts.

[0146] When a single catalyst is used, it is chosen from catalysts capable of carrying out both an olefin isomerization and an olefin metathesis reaction. These include in particular transition metal alkylidenes, in particular ruthenium, tungsten or molybdenum. By way of example, mention may be made of the Ru-2 catalyst described below.

[0147] When a mixture of catalysts is used, said mixture may comprise a first catalyst for carrying out olefin metathesis and a second catalyst for carrying out only olefin isomerization. The catalyst for carrying out olefin isomerization may be chosen from transition metal-based catalysts, in particular palladium, ruthenium, copper, or iron. For example, the isomerization catalysts may be chosen from a palladium catalyst (CAS: 185812-86-6) and a ruthenium catalyst [RuH(Cl)(CO)(PCy3)3] or [CpRu(PN)(MeCN)]BArF4. Alternatively, the mixture may comprise two catalysts, both capable of carrying out both olefin isomerization and an olefin metathesis reaction. Such catalysts may be chosen from transition metal alkylidenes, in particular ruthenium, tungsten or molybdenum.Examples include the Ru-2 and Ru-3 catalysts described below.

[0148] This type of catalyst or mixture of catalysts is notably described in the article: LJ Goo[3en et al. Chem. Eur. J. 2019, 25, 7416 - 7425.

[0149] Preferably, the catalyst or mixture of catalysts used in step ii) is or comprises a transition metal complex, in particular ruthenium.

[0150] Preferably, the isomerizing metathesis catalyst is a mixture of Ru-2 and Ru-3 catalysts. Preferably the Ru-2 / Ru-3 molar ratio varies from 0.1 to 1 and is in particular 0.5.

[0151] [Chem.3] Ru-2

[0152] Ru-2 has the chemical formula: C52H77CI2N2PRU, for molar mass: 933.15 g.mol *, and for CAS reference: 373640-75-6.

[0153] [Chem.4] ch3 Ru-3

[0154] Ru-3 has the chemical formula: CaçHsoC^FsNaC^Ru, for molar mass: 821.81 g.mol1 and for CAS reference: 1212008-99-5.

[0155] The quantity of catalyst can vary between 0.01 and 2 mol%, in particular between 0.1 and 1 mol% relative to the mixture of internal olefins used in step ii).

[0156] Step ii) is carried out in particular at a temperature between 70°C and 90°C, under an inert atmosphere. It is carried out in particular in a polar and aprotic solvent, for example THF.

[0157] The reaction mixture in step ii) can be stirred until the complete conversion of the mixture of internal olefins from step i), which can be monitored by proton NMR. The mixture can thus be stirred for 1 to 3 hours, in particular for 2 hours.

[0158] At the end of step i), the catalyst can be neutralized, in particular by adding an alkyl vinyl ether to the reaction mixture of step ii).

[0159] Preferably, the metathesis catalyst is removed, for example by silica gel chromatography and / or by filtration.

[0160] Step iii) of hydrogenation

[0161] The hydrogenation step can be carried out in the presence of a palladium on carbon catalyst, in particular at a temperature between 40°C and 60°C, in an apolar aprotic solvent, such as cyclohexane.

[0162] It is carried out in the presence of dihydrogen, for example under a pressure of 1 bar.

[0163] The reaction mixture from step iii) can be stirred until the complete conversion of the mixture of internal olefins from step ii), which can be monitored by proton NMR. The reaction mixture in step iii) can thus be stirred for several hours, in particular for 10 to 20 hours. It can include a filtration step to remove the catalyst at the end of the reaction.

[0164] Naturally occurring linear terminal olefins

[0165] The origin of the terminal olefins used in step i) can be varied. Indeed, terminal olefins can be synthesized from unsaturated fatty acid esters derived from vegetable oils or fatty esters derived from jojoba oil, according to methods known to those skilled in the art. On this subject, reference may be made in particular to the following publications: JE Moore et al. / Journal of Colloid and Interface Science 547 (2019) 275-290; J. Terao et al. Angew. Chem. Int. Ed. 2007, 46, 2086-2089, Y. Fujimoto et al, Org. Biomol. Chem. 2016, 14, 6672).

[0166] For example, these terminal olefins can be obtained by an ethenolysis reaction involving unsaturated fatty acid esters from vegetable oils, preferably unsaturated fatty esters from jojoba oil [Fig.9]. An ethenolysis catalyst is used. These include transition metal alkylidenes, especially ruthenium. For example, the Ru-4 catalyst described below may be mentioned.

[0168] Ru-4 has the chemical formula C33H42CI2NORU, with a molar mass of 639.67 g / mol.

[0169] Ru-4 is notably described in the article: Sytniczuk et al., Chem Catalysis 3, 100713.

[0170] The quantity of catalyst can vary between 0.001 and 1 mol%, in particular between 0.01 and 0.5 mol% relative to the jojoba oil.

[0171] The ethenolysis reaction is carried out at a temperature between 35°C and 45°C, in particular at 40°C.

[0172] The ethenolysis reaction is carried out in an autoclave in the presence of ethylene (99.95% purity), for example under a pressure of 10 bar.

[0173] The mixture can thus be stirred for 4 to 8 hours, in particular for 6 hours.

[0174] At the end of the ethenolysis reaction, the catalyst is neutralized, in particular by adding an alkyl vinyl ether to the reaction mixture.

[0175] The conversion of the ethenolysis reaction can be quantified by GC using an internal standard, trimethoxybenzene.

[0176] In embodiments, said at least one terminal linear olefin used in step i) is a mixture of at least two distinct terminal linear olefins, in particular three distinct terminal olefins, each comprising between 5 and 24 carbon atoms, in particular between 16 and 24 carbon atoms, preferably between 16 and 20 carbon atoms.

[0177] The distinct terminal linear olefins necessarily differ from each other by a carbon number of at least one. Step i) is then a cross metathesis step.

[0178] In embodiments, said at least two terminal linear olefins differ from each other by a number of carbons of at least one, in particular at least two.

[0179] According to a preferred embodiment, said at least one terminal linear olefin used in step i) is a mixture of three terminal linear olefins, preferably C16 / C18 / C20.

[0180] In particular, a mixture of terminal linear olefins comprising or consisting of: - From 1 to 10% by weight of C16 terminal olefins; - From 45 to 49.5% of terminal olefins in Cl8; and - From 45 to 49.5% of C20 terminal olefins;

[0181] Mixture of linear alkanes of natural origin

[0182] According to another aspect, the invention relates to a mixture of linear alkanes of natural origin, in particular of plant origin, said mixture being capable of being obtained according to the process of the invention.

[0183] According to embodiments, the mixture comprises at least two distinct linear alkanes, said at least two distinct linear alkanes each comprising between 10 and 70 carbon atoms, in particular 17 and 70 carbon atoms, preferably between 24 and 60 carbon atoms.

[0184] According to yet another aspect, the invention relates to a mixture of linear alkanes of natural origin, in particular of plant origin, in the form of a solid fatty substance, in which: - each linear alkane constituting the mixture contains between 10 and 70 carbon atoms, in particular between 17 and 70 carbon atoms, and - the distribution of the numbers of each linear alkane, arranged by increasing number of carbon atoms, is: • increasing between the linear alkane having the smallest number of carbon atoms up to the mode of the distribution; and • decreasing between the distribution mode and the linear alkane with the largest carbon number, • the numbers being calculated as a percentage by weight relative to the total weight of the mixture of linear alkanes of natural origin.

[0185] According to embodiments, each linear alkane in the distribution differs from the consecutive linear alkane in the distribution by a carbon number equal to one. For example, in the case of a distribution where the smallest number of carbon atoms is Cl6, and where the largest number of atoms is C20, then the distribution includes the following alkanes: C16, C17, C18, C19 and C20.

[0186] According to embodiments, the number of distinct linear alkanes constituting the mixture is at least 10, in particular at least 20, in particular at least 30, in particular at least 40.

[0187] According to embodiments, the mixture has a melting point between 31.5°C and 90°C. The melting point is in particular determined by DSC thermogravimetric analysis.

[0188] The alkane having the smallest or largest number of atoms is in particular an alkane whose weight percentage represents at least 1% by weight relative to the total weight of the mixture of linear alkanes. Below this threshold, any linear alkanes present will be considered to be present in trace amounts and will not be considered to be part of the distribution. For example, a mixture of alkanes according to the present application in the form of a C16-C20 distribution, that is to say where the smallest number of carbon atoms is C16, and where the largest number of atoms is C20, may possibly contain C14, C15, C21, or C22 alkanes but their respective concentration by weight will be less than 1% by weight of the total mixture.

[0189] This threshold value of 1% by weight is in particular set in relation to a sample whose concentration is at least 500pg / mL, analyzed by Gas Chromatography (GC), in particular with a Shimadzu GC-2014 device with an Agilent VF-5ht column having the following characteristics: 30m X 0.25mm X 0.10pm, maximum temperature: 430°C.

[0190] According to embodiments, each linear alkane constituting the mixture comprises between 20 and 65. In the context of the present description, this means in other words that the linear alkane having the smallest number of carbon atoms within the distribution is a C20 alkane and / or the alkane having the largest number of atoms is a C65 alkane.

[0191] According to embodiments, each linear alkane constituting the mixture comprises between 24 and 60 carbon atoms.

[0192] According to embodiments, the distribution mode is between 40 and 45 carbon atoms, and is in particular 41 carbon atoms.

[0193] According to embodiments, the median of the distribution is between 40 and 45 carbon atoms, and is notably between 41 and 43 carbon atoms.

[0194] According to embodiments, the average of the distribution is between 40 and 45 carbon atoms, and is notably between 41 and 42 carbon atoms.

[0195] According to embodiments, the distribution of linear alkanes is asymmetric.

[0196] According to embodiments, the mixture has a melting point between 75 and 85°C, about 80°C.

[0197] Preferably, the mixture of linear alkanes is characterized in that it contains from 3% to 6% by weight of linear C30 to C54 alkanes, relative to the total weight of the mixture.

[0198] According to embodiments, the mixture of linear alkanes is a mixture in which each linear alkane constituting the mixture comprises between:

[0199] - 17 and 44 carbon atoms; or

[0200] - 22 and 54 carbon atoms; or

[0201] - 12 and 47 carbon atoms; or

[0202] - 11 and 50 carbon atoms; or

[0203] - 11 and 54 carbon atoms.

[0204] According to embodiments, the mixture of linear alkanes constituting the mixture comprises between 17 and 44 carbon atoms, and has a melting point of approximately 48°C.

[0205] According to embodiments, the mixture of linear alkanes constituting the mixture comprises between 22 and 54 carbon atoms, and has a melting point of approximately 75°C.

[0206] According to embodiments, the mixture of linear alkanes constituting the mixture comprises between 12 and 47 carbon atoms, and has a melting point of approximately 31.5°C.

[0207] According to embodiments, the mixture of linear alkanes constituting the mixture comprises between 11 and 50 carbon atoms, and has a melting point of approximately 37°C.

[0208] According to embodiments, the mixture of linear alkanes constituting the mixture comprises between 11 and 54 carbon atoms, and has a melting point of approximately 57°C.

[0209] By "about x" is meant the values ​​in the interval from x - 0.lx and x + 0.lx.

[0210] Compositions

[0211] According to yet another aspect, the invention relates to a composition comprising a mixture of linear alkanes according to the invention, in particular a cosmetic and / or pharmaceutical composition.

[0212] According to embodiments, the compositions according to the invention comprise less than 3% of additional solid fatty substances of mineral and / or synthetic origin, in particular less than 1%. Preferably, the cosmetic compositions are free of additional solid fatty substances of mineral and / or synthetic origin, the percentages being expressed by weight relative to the total weight of the composition.

[0213] Cosmetic composition

[0214] According to yet another aspect, the invention relates to a cosmetic composition comprising a mixture of linear alkanes according to the invention.

[0215] According to embodiments, the cosmetic compositions comprise from 0.1% to 25% by weight of a mixture of linear alkanes according to the invention, relative to the total weight of the composition.

[0216] In particular, when the cosmetic composition is in the form of a cream, in particular a relatively compact one, it may comprise from 0.1% to 5% by weight of a mixture of linear alkane according to the invention, relative to the total weight of the composition.

[0217] When the cosmetic composition is in the form of a product cast in a cup, it may comprise from 0.1% to 12% by weight of a mixture of linear alkanes according to the invention, relative to the total weight of the composition.

[0218] When the cosmetic composition is in the form of a stick, it may comprise from 0.1% to 25% by weight of a mixture of linear alkanes according to the invention, relative to the total weight of the composition.

[0219] When the cosmetic composition is in the form of a mascara, it may comprise from 0.1% to 15% by weight of a mixture of linear alkanes according to the invention, relative to the total weight of the composition.

[0220] The cosmetic composition may be characterized in particular in that it is a care product, a makeup product, or a perfuming product. This product may be intended for the skin (face, eyelids), mucous membranes (in particular the lips) or the appendages (eyelashes, eyebrows, hair, nails). Among these products, mention may in particular be made of anhydrous products or products in emulsion form, such as wax-in-water emulsions, water-in-oil emulsions, oil-in-water emulsions or multiple emulsions. It may in particular be a cosmetic composition, preferably anhydrous, in solid form for the care and / or makeup of keratin materials, in particular the skin, eyelids, eyebrows or lips, comprising, in a physiologically acceptable medium, a mixture of linear alkanes according to the invention.

[0221] By "anhydrous composition" is meant in particular that water is preferably not deliberately added to the composition of the invention but may be present in trace amounts in the various compounds used in the composition. In particular, the composition according to the invention comprises less than 4% by weight of water, preferably less than 3%, preferably less than 2%, more preferably less than 1%, even more preferably less than 0.5% by weight of water, relative to the total weight of said composition, or even is completely free of water. According to a particular embodiment, the composition is free of water. By "composition in solid form" is meant according to the invention a composition having, at a temperature of 20°C and at atmospheric pressure (760 mm Hg), a hardness greater than 30 Nm1, preferably greater than 40 Nm1. The hardness can be measured at 20°C by the so-called "butter cutter" method, which consists of evaluating the firmness of a lipstick by measuring in particular the cutting resistance of the stick product. This measurement is carried out 24 hours after formulation, using a texturometer (TAXTPlus, MicroStable Systems, United Kingdom) equipped with a 5 kg force cell and its Butter Cutter A / BC probe (Swantech, MicroStable Systems, United Kingdom). It makes it possible to measure the maximum resistance force of the stick when the butter cutter penetrates to a depth of 9 mm at a speed of 1.6 mm / s. To ensure the reproducibility of the measurements, the analysis is repeated on 6 sticks and the relative deviation between the measurements must not be greater than 10%, ideally 5%.For each type of product, a reference (target) range is established to guarantee the mechanical properties of the stick. The solid composition according to the invention will generally have a hardness greater than or equal to 70g, in particular greater than or equal to 90g, for example ranging from 100g to 400g, and preferably ranging from 140g to 300g and even more preferably ranging from 175g to 250g. Such compositions (corresponding in particular to cast sticks in standard format of approximately 12.7mm), have adequate stability and hardness: the stick is sufficiently rigid and solid, does not break during application and is thus compatible with packaging in a stick or in another solid form and with application by friction on the surface to be treated and / or made up; they are also characterized by ease of application such as good glide, good deposit from the first application and a comfortable texture.The composition may be in the form of a stick or a composition packaged in a cup. It may also be fluid products such as lip gloss or mascara (wax emulsions in water). It may also be products in the form of loose or compact powders.

[0222] The cosmetic compositions according to the invention may further comprise other ingredients, in particular additional solid fatty substances, in particular polar and / or apolar waxes, or pasty fatty substances.

[0223] By "additional solid fatty substances" is meant here fatty substances distinct from the mixtures of linear alkanes according to the invention. These additional solid fatty substances may in particular be of mineral and / or synthetic origin.

[0224] According to embodiments, the cosmetic compositions according to the invention comprise less than 3% by weight of additional solid fatty substances of mineral and / or synthetic origin, in particular less than 1% by weight. Preferably, the cosmetic compositions are free of additional solid fatty substances of mineral and / or synthetic origin. mineral and / or synthetic, the percentages being expressed by weight relative to the total weight of the composition.

[0225] By polar wax is meant a wax comprising at least one heteroatom such as oxygen, nitrogen, silicon or phosphorus.

[0226] In particular, the polar wax may be chosen from the group comprising beeswax, carnauba wax, candelilla wax, cotton wax, rice bran wax, bay wax, Chinese insect wax, lanolin and its alcohol derivatives, acetylated, esterified, polyethoxylated, kapok wax, sugar cane wax, hexyl laurate, jojoba wax, shellac wax, polyethoxylated cholesterol ether, synthetic beeswaxes marketed by Koster Keunen under the trade name Kester Wax K82H, or a mixture thereof.

[0227] Mention may also be made of plant ester waxes chosen from the group comprising the mixture of jojoba esters, polyglycerin-3, Acacia decurrens flower wax and sunflower seed wax, said mixture being marketed by Gattefosse under the trade name Acticire®, the jojoba esters marketed by Floratech under the trade name Floraesters 60 or Floraesters 70, the alkyl esters or hydrogenated alkyl esters marketed by Sophim under the trade name Phytowax, such as for example the hydrogenated lauroyl oleate esters marketed under the name Phytowax Olive 12L44.

[0228] By “apolar wax” is meant a hydrocarbon wax and / or a silicone wax.

[0229] The term “apolar hydrocarbon wax” means a wax comprising only carbon and hydrogen atoms and not including heteroatoms such as oxygen, nitrogen, silicon or phosphorus.

[0230] Examples of apolar hydrocarbon waxes suitable for use in the compositions of the invention include polyethylene wax, such as that marketed by New Phase Technologies under the name Performalene 400 (P400) or by Jeen International Corporation under the name Jeenate 3H, a blend of high molecular weight linear polyethylene and ethylene / propylene copolymer, marketed by Safi-Alcan under the trade name Lipwax® PZ80-20, a synthetic wax such as that marketed by Sasol under the name Sasol Wax C80, blends of synthetic waxes and vegetable waxes, such as, for example, a blend of synthetic wax and carnauba wax (Copemica cerifera) marketed by Strahl & Pitsch under the name Smart wax 202, a blend of synthetic wax, Candelilla wax and carnauba wax (Copemica cerifera) marketed by Strahl & Pitsch under the name Smartwax 7743S,Fischer Tropsch waxes such as those marketed by Cirebelle under the name Cirebelle 303, or one of their mixtures, montan wax, ceresins, ozokerites, microcrystalline waxes, mineral paraffins.

[0231] The term “apolar silicone wax” means a wax comprising a silicon heteroatom.

[0232] An example of a silicone apolar wax suitable in the compositions of the invention is C24-28 alkyl dimethicone, marketed by Evonik Industries AG under the name Abil Wax.

[0233] The cosmetic compositions according to the invention may comprise an additional pasty fatty substance. A compound of this type is in particular a mixture of sterol esters, such as the mixture of cholesterol and lanosterol ester available from the manufacturer CRODA under the trade name Super Sterol Ester®.

[0234] The compositions according to the invention may further comprise a pasty fatty substance which may advantageously be chosen from: - vaselines also called petrolatum - lanolin and its derivatives, - polymeric or non-polymeric silicone compounds - polymeric or non-polymer fluorinated compounds, - vinyl polymers, in particular homopolymers and copolymers of olefins, homopolymers and copolymers of hydrogenated dienes, linear or branched oligomers, homo or copolymers of alkyl (meth)acrylates preferably having a C8-C30 alkyl group, homo and copolymer oligomers of vinyl esters having C8-C30 alkyl groups, homo and copolymer oligomers of vinyl ethers having C8-C30 alkyl groups, - liposoluble polyethers resulting from the polyetherification between one or more C2-C100 diols, preferably C2-C50, - mixtures of beeswax and octyldodecanol such as that marketed under the name Zenibee Cream by the company Zenitech, - esters, - vegetable butters such as mango, shea, cocoa, cotton, avocado butter, etc. or a mixture thereof.

[0235] Among the esters, it is possible to use in particular: - esters of an oligomeric glycerol, in particular diglycerol esters, in particular condensates of adipic acid and glycerol, for which part of the hydroxyl groups of the glycerols have reacted with a mixture of fatty acids such as stearic acid, capric acid, stearic acid and isostearic acid and 12-hydroxystearic acid, such as those marketed under the brand name Softisan 649 by the company Sasol, - arachidyl propionate marketed under the brand name Waxenol 801 by Alzo, - phytosterol esters such as the product with the INCI name "bis-behenyl / isostearyl / phytosteryl dimer dilinoleyl dimer dilinoleate" marketed under the name Plandool-G by the company Nippon Fine Chemical Co, "Phytosteryl / behenyl / octyldodecyl / isostearyl lauroyl glutamate" marketed under the name Eldew-PS308 by the company Ajinomoto, - fatty acid triglycerides and their derivatives, for example the mixture of stearyl heptanoate and stearyl caprylate marketed under the name DUB solid by the company Stéarinerie Dubois, - pentaerythritol esters, - non-crosslinked polyesters resulting from the polycondensation between a linear or branched C4-C50 dicarboxylic acid or polycarboxylic acid and a C2-C50 diol or polyol, - aliphatic esters of ester resulting from the esterification of an aliphatic hydroxycarboxylic acid ester by an aliphatic carboxylic acid such as cetyl lactate marketed under the name ceraphyl 28 by the company ISP (International Speciality Products), - polyesters resulting from the esterification, by a polycarboxylic acid, of an aliphatic hydroxycarboxylic acid ester, said ester comprising at least two hydroxyl groups such as the products Risocast DA-H ®, and Risocast DA-L ®, or one of their mixtures.

[0236] Among the additional pasty fatty substances, phytosterol esters will preferably be chosen, such as the product corresponding to the INCI name "bis-behenyl / isostearyl / phytosteryl dimer dilinoleyl dimer dilinoleate" marketed under the name Plandool-G by the company Nippon Fine Chemical Co, "Phytosteryl / behenyl / o ctyldodecyl / isostearyl lauroyl glutamate" marketed under the name Eldew-PS308 by the company Ajinomoto, or a mixture of these.

[0237] The compositions may comprise additional fatty substances having a melting point of between 25°C and 55°C. The fatty substance having a melting point of between 25°C and 55°C is chosen from hydrogenated oils solid at 25°C or fatty esters solid at 25°C and mixtures thereof.

[0238] Among the hydrogenated oils solid at 25°C, mention may be made of hydrogenated castor oil, hydrogenated palm oil, hydrogenated tallow, hydrogenated coconut oil such as for example that available under the trade name hydrobase 32-34 by the company Prod'Hyg.

[0239] Among the fatty esters solid at 25°C, mention may be made of propylene glycol myristate, myristyl myristate and cetyl alcohol.

[0240] The fatty component having a melting point between 25°C and 55°C is preferably hydrogenated coconut oil.

[0241] The cosmetic compositions according to the invention may further comprise a lipophilic gelling agent, or a film-forming polymer.

[0242] Lipophilic gelling agent

[0243] The term “lipophilic gelling agent” designates, in the context of the present application, a substance capable of solidifying or gelatinizing the oil present in the composition of the invention.

[0244] Among the lipophilic gelling agents used, mention may be made in particular of organic or mineral polymeric or molecular lipophilic gelling agents.

[0245] As an example of a polymeric organic lipophilic gelling agent, mention may be made of esters of sucrose and fatty acids, and preferably esters of sucrose, stearic acid and acetic acid, such as sucrose tetrastearate triacetate (corresponding to the INCI name sucrose tetrastearate triacetate) available under the trade name Sistema® A10E-C from the company Sisterna.

[0246] Another type of polymeric organic lipophilic gelling agent other than sucrose polyester consists of dextrin esters. Examples include dextrin esters of fatty acids, such as dextrin palmitate.

[0247] Another type of polymeric organic lipophilic gelling agent consists of glyceryl esters. Mention may be made of the diester of eicosadioic acid and glycerol esterified by behenic acid. It is in particular available under the trade name NOMCORT® HK-G from the company NISSHIN OILLIO.

[0248] As a mineral lipophilic gelling agent, mention may be made of fumed silica, optionally hydrophobically treated on the surface, the particle size of which is less than 1 μm. It is in fact possible to chemically modify the surface of the silica, by chemical reaction generating a reduction in the number of silanol groups present on the surface of the silica. In particular, silanol groups can be substituted by hydrophobic groups: a hydrophobic silica is then obtained. The hydrophobic groups may be: - trimethylsiloxyl groups, which are in particular obtained by treatment of fumed silica in the presence of hexamethyldisilazane. Silicas thus treated are called "Silica silylate" according to the CTFA (8th edition, 2000).They are for example marketed under the references Aerosil R812® by the company DEGUSSA, CAB-O-SIL TS-530® by the company CABOT, - dimethylsilyloxyl or polydimethylsiloxane groups, which are in particular obtained by treatment of fumed silica in the presence of polydimethylsiloxane or dimethyldichlorosilane. Silicas thus treated are called "Silica dimethyl silylate" according to the CTFA (8th edition, 2000). They are for example marketed under the references Aerosil R972®, and Aerosil R974® by the company DEGUSSA, CAB-O-SIL TS-610® and CAB-O-SIL TS-720® by the company CABOT.

[0249] The hydrophobic fumed silica has in particular a particle size which can be nanometric to micrometric, for example ranging from approximately 5 to 200 nm.

[0250] Polymeric organic lipophilic gelling agents are, for example, partially or totally crosslinked elastomeric organopolysiloxanes of three-dimensional structure, such as those sold under the names KSG6®, KSG16® and KSG18® by the company SHIN-ETSU, Trefil E-505C® and Trefil E-506C® by the company DOW-CORNING, Gransil SR-CYC®, SR DMF10®, SR-DC556®, SR 5CYC gel®, SR DMF 10 gel® and SR DC 556 gel® by the company GRANT INDUSTRIES, SF 1204® and JK 113® by the company GENERAL ELECTRIC; ethylcellulose such as that sold under the name Ethocel® by the company DOW CHEMICAL; galactommanans comprising from one to six, and in particular from two to four, hydroxyl groups per ose, substituted by a saturated or unsaturated alkyl chain, such as guar gum alkylated by C1 to C6 alkyl chains, and in particular C1 to C3 or one of their mixtures.Block copolymers of the "diblock", "triblock" or "radial" type of the polystyrene / polyisoprene, polystyrene / polybutadiene type such as those marketed under the name Luvitol HSB® by the company BASF, of the polystyrene / copoly(ethylene-propylene) type such as those marketed under the name Kraton® by the company SHELL CHEMICAL CO or of the polystyrene / copoly(ethylene-butylene) type, mixtures of triblock and radial (star) copolymers in isododecane such as those marketed by the company PENRECO under the name Versagel® such as for example the mixture of butylene / ethylene / styrene triblock copolymer and ethylene / propylene / styrene star copolymer in isododecane (Versagel M 5960) or in hydrogenated polyisobutene (Versagel ME 2000).

[0251] Another type of polymeric organic lipophilic gelling agent consists of polyamide resins or poly(ester-amide) resins, such as ester-terminated polyamides (ETPA), ester-terminated poly(ester-amides) (ETPEA), tertiary amide-terminated polyamides (ATPA), polyalkyleneoxy-terminated polyamides (PAOPA) or polyether polyamides (PEPA).

[0252] Examples of ester-terminated polyamides (ETPAs) are those identified by the INCI name "Ethylenediamine / Stearyl Dimer Dilinoleate Copolymer" and available, for example, under the trade name Uniclear® 100VG from Arizona Chemical.

[0253] Examples of ester-terminated poly(ester-amides) (ETPEA) are those identified by the INCI name polyamide-8 which are "Ethylenediamine bis-stearyl ethylenediamine / neopentyl glycol / stearyl dibenzoate dimer copolymers" and available, for example, under the trade name Oloecraft® LP-20-PA-MV from Croda.

[0254] Examples of tertiary amide terminated polyamides (ATPA) are those identified by the INCI name "Ethylenediamine / Hydrogenated Dimer Diilinoate Copolymer Bis-Di-C14-18 Alkyl Amide" and available, for example, under the trade name Sylvaclear® A200V or Sylvaclear® A2614V from Arizona Chemical or those identified by the INCI name "Diisostearyl malate and bis-dioctadecylamide dimer dilinoleic acid / ethylenediamine" and available, for example, under the trade name Haimalate PAM from Kokyu Alcohol Kogyo.

[0255] Examples of polyalkyleneoxy terminated polyamides (PAOPAs) are those identified by the INCI name Polyamide-3 and available, for example, as Sylvaclear® AF1900V, Sylvaclear® PE1800V and Sylvaclear® PA1200V from Arizona Chemical.

[0256] Examples of polyether polyamides (PEPA) are those identified by the INCI name Polyamide-6 and available, for example, under the name Sylvaclear® PE400V from Arizona Chemical.

[0257] Another type of polymeric organic lipophilic gelling agent is N-acyl glutamic acid diamides. Examples include an N-acyl glutamic acid diamide having a straight-chain alkyl group such as dibutyl lauroyl glutamide and an N-acyl glutamic acid diamide having a branched-chain alkyl group, such as dibutyl ethylhexanoyl glutamide. Dibutyl lauroyl glutamide is commercially available as GP-1 and dibutyl ethylhexanoyl glutamide is commercially available as EB-21, both marketed by Ajinomoto.

[0258] Among the lipophilic gelling agents, sucrose and fatty acid esters, dextrin esters and glyceryl esters are preferred.

[0259] Film-forming

[0260] The composition according to the invention may also comprise at least one film-forming polymer.

[0261] Among the film-forming polymers that can be used in the compositions of the present invention, mention may be made of synthetic polymers, of radical type or of polycondensate type, polymers of natural origin, and their mixtures.

[0262] By radical film-forming polymer is meant a polymer obtained by polymerization of monomers with unsaturation, in particular ethylenic unsaturation, each monomer being capable of homopolymerizing (unlike polycondensates).

[0263] The radical-type film-forming polymers may in particular be vinyl polymers or copolymers, in particular acrylic polymers.

[0264] The vinyl film-forming polymers may result from the polymerization of ethylenically unsaturated monomers having at least one acid group and / or esters of these acid monomers and / or amides of these acid monomers.

[0265] As monomer carrying an acid group, it is possible to use α,[3-ethylenic] unsaturated carboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, maleic acid, itaconic acid. Preferably, (meth)acrylic acid, itaconic acid and crotonic acid are used, and more preferably itaconic acid (for example a metal salt of poly(itaconic acid) such as that sold under the commercial reference REVCARE NE 100S by the company Itaconix).

[0266] The esters of acid monomers are advantageously chosen from esters of (meth)acrylic acid (also called (meth)acrylates), in particular alkyl (meth)acrylates, in particular C1-C30 alkyl, preferably C1-C20 alkyl, aryl (meth)acrylates, in particular C6-C10 aryl, hydroxyalkyl (meth)acrylates, in particular C2-C6 hydroxyalkyl.

[0267] Among the alkyl (meth)acrylates, mention may be made of methyl methacrylate, ethyl methacrylate, butyl methacrylate, isobutyl methacrylate, 2-ethylhexyl methacrylate, lauryl methacrylate, cyclohexyl methacrylate.

[0268] Among the hydroxyalkyl (meth)acrylates, mention may be made of hydroxyethyl acrylate, 2-hydroxypropyl acrylate, hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate.

[0269] Among the aryl (meth)acrylates, mention may be made of benzyl acrylate and phenyl acrylate.

[0270] Particularly preferred (meth)acrylic acid esters are alkyl (meth)acrylates.

[0271] According to the present invention, the alkyl group of the esters can be either fluorinated or perfluorinated, that is to say that some or all of the hydrogen atoms of the alkyl group are substituted by fluorine atoms.

[0272] As amides of the acid monomers, mention may be made, for example, of (meth)acrylamides, and in particular of N-alkyl (meth)acrylamides, in particular of C2-C12 alkyl. Among the N-alkyl (meth)acrylamides, mention may be made of N-ethyl acrylamide, Nt-butyl acrylamide, Nt-octyl acrylamide and N-undecylacrylamide.

[0273] The vinyl film-forming polymers may also result from the homopolymerization or copolymerization of monomers chosen from vinyl esters and styrene monomers. In particular, these monomers may be polymerized with acid monomers and / or their esters and / or their amides, such as those mentioned above.

[0274] Examples of vinyl esters include vinyl acetate, vinyl neodecanoate, vinyl pivalate, vinyl benzoate, and vinyl t-butyl benzoate.

[0275] As styrenic monomers, mention may be made of styrene and alpha-methyl styrene.

[0276] Mention may also be made of styrene / butadiene block copolymers such as the products from the company Kraton, or OLEOFLEX EG 200 from the company APPLECHEM.

[0277] Among the film-forming polycondensates, mention may be made of polyurethanes, polyesters, polyester amides, polyamides, and epoxy ester resins, polyureas.

[0278] The polyurethanes may be chosen from anionic, cationic, non-ionic or amphoteric polyurethanes, polyurethane-acrylics, polyurethane-polyvinylpyrrolidones, polyester-polyurethanes, polyether-polymethanes, polyureas, polyurea-polyurethanes, and mixtures thereof.

[0279] Polyesters can be obtained, in a known manner, by polycondensation of dicarboxylic acids with polyols, in particular diols.

[0280] The dicarboxylic acid may be aliphatic, alicyclic or aromatic. Examples of such acids include: oxalic acid, malonic acid, dimethylmalonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, 2,2-dimethylglutaric acid, azelaic acid, suberic acid, sebacic acid, fumaric acid, maleic acid, itaconic acid, phthalic acid, dodecanedioic acid, 1,3-cyclohexanedicarboxylic acid, 1,4-cyclohexanedicarboxylic acid, isophthalic acid, terephthalic acid, 2,5-norbornane dicarboxylic acid, diglycolic acid, thiodipropionic acid, 2,5-naphthalenedicarboxylic acid, 2,6-naphthalenedicarboxylic acid. These dicarboxylic acid monomers can be used alone or in combination of at least two dicarboxylic acid monomers. Among these monomers, phthalic acid, isophthalic acid and terephthalic acid are preferably chosen.

[0281] The diol may be chosen from aliphatic, alicyclic, aromatic diols. Preferably, a diol chosen from: ethylene glycol, diethylene glycol, triethylene glycol, 1,3-propanediol, cyclohexane dimethanol, 4-butanediol is used. As other polyols, glycerol, pentaerythritol, sorbitol, trimethylol propane may be used.

[0282] Polyester amides can be obtained in a manner analogous to polyesters, by polycondensation of diacids with diamines or amine alcohols. As diamine, ethylenediamine, hexamethylenediamine, meta- or para-phenylenediamine can be used. As amino alcohol, monoethanolamine can be used. As polyamide resins, mention may also be made of that corresponding to the INCI name DIISOSTEARYL MALATE & BIS DIOCTADECYLAMIDE DIMER DILINOLEIC ACID / ETHYLENE DIAMINE COPOLYMER marketed under the name Haimalate PAM by the company Kokyu alcohol Kogyo.

[0283] The polyester may further comprise at least one monomer carrying at least one -SO3M group, with M representing a hydrogen atom, an ammonium ion NH4+ or a metal ion, such as for example a Na+, Li+, K+, Mg2+, Ca2+, Cu2+, Fe2+, Fe3+ ion. In particular, a bifunctional aromatic monomer comprising such a -SO3M group may be used.

[0284] The aromatic nucleus of the bifunctional aromatic monomer further bearing a -SO3M group as described above may be chosen, for example, from benzene, naphthalene, anthracene, diphenyl, oxydiphenyl, sulfonyldiphenyl, methylenediphenyl nuclei. Examples of bifunctional aromatic monomer further bearing a -SO3M group include: sulfoisophthalic acid, sulfoterephthalic acid, sulfophthalic acid, 4-sulfonaphthalene-2,7-dicarboxylic acid.

[0285] It is possible to use isophthalate / sulfoisophthalate-based copolymers, and more particularly copolymers obtained by condensation of diethylene glycol, cyclohexane dimethanol, isophthalic acid, sulfoisophthalic acid.

[0286] The polymers of natural origin, optionally modified, may be chosen from shellac resin, sandarac gum, gum arabic (ACACIA SENEGAL GUM), dammars, elemis, copals, cellulose polymers, polymers extracted from the fruit of Caesalpinia spinosa and / or from the algae Kappaphycus alvarezii (such as the product Filmexel® marketed by the company Silab), and mixtures thereof. A natural polymer such as Filmexel® makes it possible in particular to improve the strength of the film obtained from the composition according to the invention. Mention may also be made of the film-forming polymers corresponding to the INCI name SHOERA ROBUSTA RESIN + BEESWAX, SHOERA ROBUSTA RESIN + SUNFLOWER OIL, ARAUCARIA + SUNFLOWER OIL, ARAUCARIA + CASTOR OIL, SHOERA ROBUSTA + OCTYLDODECANOL. Rosin esters such as glyceryl rosinate available under the trade name NatPure GR from the company Gattefossé can also be mentioned.

[0287] According to one embodiment, the film-forming polymer may be a polymer solubilized in a liquid fatty phase comprising oils or organic solvents (the film-forming polymer is then said to be a liposoluble polymer).

[0288] As an example of a liposoluble polymer, mention may be made of copolymers of vinyl ester (the vinyl group being directly linked to the oxygen atom of the ester group and the vinyl ester having a saturated, linear or branched hydrocarbon radical of 1 to 19 carbon atoms, linked to the carbonyl of the ester group) and at least one other monomer which may be a vinyl ester (different from the vinyl ester already present), an α-olefin (having from 8 to 28 carbon atoms), an alkyl vinyl ether (the alkyl group of which comprises from 2 to 18 carbon atoms), or an allylic or methallyl ester. (having a saturated, linear or branched hydrocarbon radical of 1 to 19 carbon atoms, linked to the carbonyl of the ester group).

[0289] These copolymers can be crosslinked using crosslinkers which can be either of the vinyl type, or of the allylic or methallyl type, such as tetraallyloxyethane, divinylbenzene, divinyl octanedioate, divinyl dodecanedioate, and divinyl octadecanedioate.

[0290] Examples of such copolymers include vinyl acetate / allyl stearate, vinyl acetate / vinyl laurate, vinyl acetate / vinyl stearate, vinyl acetate / octadecene, vinyl acetate / octadecyl vinyl ether, vinyl propionate / allyl laurate, vinyl propionate / vinyl laurate, vinyl stearate / octadecene-1, vinyl acetate / dodecene-1, vinyl stearate / ethyl vinyl ether, vinyl propionate / cetyl vinyl ether, vinyl stearate / allyl acetate, 2,2-dimethyl vinyl octanoate / vinyl laurate, 2,2-dimethyl allyl pentanoate / vinyl laurate, vinyl dimethyl propionate / vinyl stearate, allyl dimethyl propionate / vinyl stearate, vinyl propionate / vinyl stearate, crosslinked with 0.2% divinyl benzene, vinyl dimethyl propionate / vinyl laurate, crosslinked with 0.2% divinyl benzene, vinyl acetate / octadecyl vinyl ether, crosslinked with 0.2% tetraallyloxyethane,vinyl acetate / allyl stearate, crosslinked with 0.2% divinyl benzene, vinyl acetate / octadecene-1 crosslinked with 0.2% divinyl benzene and allyl propionate / allyl stearate crosslinked with 0.2% divinyl benzene. ,

[0291] As liposoluble film-forming polymers, mention may also be made of liposoluble copolymers, and in particular those resulting from the copolymerization of vinyl esters having from 9 to 22 carbon atoms or of alkyl acrylates or methacrylates, the allyl radicals having from 10 to 20 carbon atoms.

[0292] Such liposoluble copolymers may be chosen from copolymers of polyvinyl stearate, polyvinyl stearate crosslinked using divinylbenzene, diallyl ether or diallyl phthalate, copolymers of poly(meth)acrylate of stearyl, polyvinyl laurate, poly(meth)acrylate of lauryl, these poly(meth)acrylates being able to be crosslinked using methylene glycol dimethacrylate or tetraethylene glycol.

[0293] The liposoluble copolymers defined above are known and in particular described in application FR-A-2232303; they can have a weight-average molecular weight ranging from 2,000 to 500,000 and preferably from 4,000 to 200,000.

[0294] Mention may also be made of liposoluble homopolymers, and in particular those resulting from the homopolymerization of vinyl esters having from 9 to 22 carbon atoms or of alkyl acrylates or methacrylates, the alkyl radicals having from 2 to 24 carbon atoms.

[0295] Examples of liposoluble homopolymers that may be mentioned include: polyvinyl laurate and lauryl poly(meth)acrylates, these poly(meth)acrylates being able to be crosslinked using ethylene glycol dimethacrylate or tetraethylene glycol.

[0296] As liposoluble film-forming polymers which can be used in the invention, mention may also be made of polyalkylenes and in particular copolymers of C2-C20 alkenes, such as polybutene, alkylcelluloses with a linear or branched alkyl radical, saturated or not in C1 to C8 such as ethylcellulose and propylcellulose, copolymers of vinylpyrrolidone (VP) and in particular copolymers of vinylpyrrolidone and of C2 to C40 alkenes and better still in C3 to C20. As an example of a VP copolymer that can be used in the invention, mention may be made of the VP / vinyl acetate copolymer, VP / ethyl methacrylate, butylated polyvinylpyrrolidone (PVP), VP / ethyl methacrylate / methacrylic acid, VP / eicosene (ANTARON V220 marketed by the company Ashland), VP / hexadecene (ANTARON V216 marketed by the company Ashland), VP / triacontene, VP / styrene, VP / acrylic acid / lauryl methacrylate.

[0297] Mention may also be made of dextrin esters and in particular: - dextrin isostearate & isostearic acid marketed under the name UNIFILMA HVY by the company Chiba Flour Milling - dextrin palmitate / ethylhexanoate marketed under the name RHEOPEARL TT by the company Chiba Flour Milling - Dextrin Myristate marketed under the name RHEOPEARL MKL2 by the company Chiba Flour Milling

[0298] Mention may also be made of sugar esters and in particular sucrose acetate isobutyrate marketed under the name EASTMAN SUSTANE SAIB by the company EASTMAN.

[0299] Mention may also be made of silicone resins, generally soluble or swellable in silicone oils, which are crosslinked polyorganosiloxane polymers. The nomenclature of silicone resins is known as "MDTQ", the resin being described according to the different siloxane monomeric units that it comprises, each of the letters "MDTQ" characterizing a type of unit.

[0300] Examples of commercially available polymethylsilsesquioxane resins include those marketed by the company Wacker under the reference Resin MK such as Belsil PMS MK, and by the company SHIN-ETSU under the references KR-220L, or silform flexible resin.

[0301] As siloxysilicate resins, mention may be made of trimethylsiloxysilicate (TMS) resins such as those marketed under the reference SR1000 by the company General Electric or under the reference TMS 803 by the company Wacker. Mention may also be made of trimethylsiloxysilicate resins marketed in a solvent such as cyclomethicone, sold under the name “KF-7312J” by the company Shin-Etsu, “DOWSIL™ RSN-0749”, “DOWSIL™ 593 Fluid” by the company Dow Corning.

[0302] Mention may also be made of copolymers of silicone resins such as those mentioned above with polydimethylsiloxanes, such as the pressure-sensitive adhesive copolymers marketed by the company Dow Corning under the reference BIO-PSA and described in document US 5,162,410 or even silicone copolymers resulting from the reaction of a silicone resin, such as those described above, and a diorganosiloxane such as described in document WO 2004 / 073626.

[0303] It is also possible to use copolymers with a non-silicone organic skeleton grafted with monomers containing a polysiloxane unit, such as for example butyl acrylate / hydroxypropyl dimethicone acrylate copolymer marketed under the name GRANACRYSIL BAS by the company GRANT.

[0304] Finally, mention may be made of acrylate / polytrimethylsiloxymethacrylate copolymers comprising a carbosiloxane dendrimer structure grafted onto a vinyl skeleton commercially available under the references DOWSIL FA 4002 ID or DOWSIL FA 4001 CM.

[0305] It is also possible to use silicone polyamides of the polyorganosiloxane type such as those described in documents US-A-5,874,069, US-A-5,919,441, US-A-6,051,216 and US-A-5,981,680.

[0306] As film formers, it is preferred to use natural resins, dextrin esters and rosin esters.

[0307] In a preferred embodiment, the composition according to the invention comprises from 1 to 15% by weight of a film-forming polymer, preferably 5 to 12% by weight of at least one film-forming polymer.

[0308] Oil For the purposes of the present invention, the term "oil" means a compound which is liquid at room temperature (25°C), and which, when introduced at a rate of at least 1% by weight into water at 25°C, is not at all soluble in water, or soluble to a level of less than 10% by weight, relative to the weight of oil introduced into the water.

[0309] Non-volatile oil

[0310] The term "non-volatile oil" means an oil which has a boiling point generally above 300°C under 760 mm Hg (101325 Pa) and which has little or no vapor pressure.

[0311] The non-volatile oils may in particular be chosen from non-volatile silicone oils, non-volatile hydrocarbon oils and their mixtures.

[0312] The term “silicone oil” means an oil comprising at least one silicon atom, and in particular at least one Si-O group.

[0313] As non-volatile silicone oil, mention may in particular be made of polydimethylsiloxanes containing at least 8 silicon atoms, polyalkylmethylsiloxane whose alkyl chain contains 8 to 20 carbon atoms and oils identified by the INCI name phenyl trimethicone.

[0314] “Hydrocarbon oil” means an oil containing hydrogen and carbon atoms.

[0315] Examples that may be mentioned are hydrocarbons such as squalane, phytosqualane, polybutene, hydrogenated polyisobutene, hydrogenated polydecene, synthetic (poly)esters also called "ester oils" and (poly)ethers, in particular (poly)esters of C6-C20 acids and C6-C20 alcohols, advantageously branched such as isononyl isononanoate; vegetable oils; branched and / or unsaturated fatty acids; branched and / or unsaturated fatty alcohols such as octyldodecanol; or a mixture thereof.

[0316] The term "ester oil" means a mono-, di-, tri- or tetra-ester oil. Ester oils are obtained by reacting a mono-, di-, tri- and more generally a polyol with a mono-di-tri- and more generally a polycarboxylic acid, said reactants being able to be linear or branched, saturated or unsaturated, aliphatic or aromatic, and possibly comprising alkoxylated groups. Ester oils can in particular be hydroxylated.

[0317] In particular, the non-volatile ester oil may comprise from 18 to 70 carbon atoms.

[0318] The non-volatile ester oil may in particular be chosen from:

[0319] - monoesters comprising 18 to 40 carbon atoms, in particular monoesters of formula R1COOR2 in which RI represents the residue of a linear or branched fatty acid containing from 6 to 20 carbon atoms and R2 represents a hydrocarbon chain, in particular a branched chain, containing from 6 to 20 carbon atoms, such as, for example, Purcellin oil (cetostearyl octanoate), isononyl isononanoate, isodecyl neopentanoate, C12 to C15 alkyl benzoates, 2-ethylhexyl palmitate, octyldodecyl neopentanoate, 2-octyldodecyl stearate, 2-octyldodecyl erucate, isostearyl isostearate, 2-octyldodecyl benzoate, alkyl octanoates, decanoates or ricinoleates, myristate isopropyl, isopropyl palmitate, butyl stearate, hexyl laurate, 2-ethylhexyl palmitate, 2-hexyldecyl laurate, 2-octyldecyl palmitate, 2-octyldodecyl myristate, 2-diethylhexyl succinate; - diesters comprising 18 to 60 carbon atoms, in particular 18 to 50 carbon atoms, such as diesters of dicarboxylic acids and monoalcohols, such as diisostearyl malate; diesters of glycol and monocarboxylic acids, such as neopentyl glycol diheptanoate or polyglyceryl-2 diisostearate; - triesters comprising 35 to 70 carbon atoms, such as tricarboxylic acid triesters, such as triisostearyl citrate or tridecyl trimellitate; or triesters glycol and monocarboxylic acids such as polyglyceryl-2 triisostearate, for example that available under the trade name Cithrol-PG-32-IS by the company Croda; - tetraesters comprising 35 to 70 carbon atoms, such as tetraesters of penthaerythritol or polyglycerol and a monocarboxylic acid, for example pentaerythrityl tetrapelargonate, pentaerythrityl tetraisostearate, pentaerythrityl tetraisononanoate, glyceryl tridecyl-2 tetradecanoate, polyglyceryl tetraisostearate-2 or pentaerythrityl tetradecyl-2 tetradecanoate; - polyesters obtained by condensation of dimer and / or trimer of unsaturated fatty acid and diol such as those described in patent application FR 0 853 634, such as the polyester of dilinoleic acid and 1,4-butanediol; - esters and polyesters of dimer diol and mono- or dicarboxylic acid, such as esters of dimer diol and fatty acid such as polyglyceryl-2 isostearate / dimer dilinoleate copolymer available under the trade name Hailuscent ISDA-MB by the company Kogyo Alcohol and esters of dimer diols and dimer dicarboxylic acid, in particular those obtained from a dimer of an unsaturated fatty acid in C8 to C34, in particular in C12 to C22, in particular in C16 to C20, and more particularly in C18, such as esters of dilinoleic diacids and dilinoleic dimer diols, for example those marketed by the company NIPPON FINE CHEMICAL under the trade name LUSPLAN DD-DA5® and DD-DA7®; - fatty acid triglycerides (liquid at room temperature), in particular fatty acids having 7 to 40 carbon atoms, such as triglycerides of heptanoic or octanoic acids or jojoba oil; saturated triglycerides such as caprylic / capric triglyceride, glyceryl triheptanoate, glycerin trioctanoate; C18-36 acid triglycerides such as those marketed under the reference DUB TGI 24 marketed by Stéarineries Dubois); and unsaturated triglycerides such as castor oil, olive oil, ximenia oil, pracaxi oil; - or one of their mixtures.

[0320] The non-volatile oil used in the present invention may be a glossy oil.

[0321] A "bright oil" is an oil whose refractive index is greater than 1.43 preferably greater than 1.45, even more preferably greater than 1.50.

[0322] The refractive index is measured using an ABBE paralux refractometer ref 60-6400-9.

[0323] An additional non-volatile oil can also be used to provide additional properties to the composition of the invention.

[0324] For example, diisostearyl malate, or Polyglyceryl-3 diisostearate available under the trade name Cithrol PG32IS by the company Croda or pentaerythrityl Adipate / Caprate / Caprylate / Heptanoate available under the trade name LEXFEEL 700 EX-LO MB by the company Inolex can be added because they allow good dispersion of the pigments to be obtained.

[0325] Other additional oils may be added to enhance the sensory properties of the formula.

[0326] According to one embodiment, the non-volatile oil is chosen from squalane, octyldodecanol, polyglyceryl-2 triisostearate, polyglyceryl-10 decaisostearate, pentaerythrityl adipate / caprate / caprylate / heptanoate, dicaprylyl carbonate, octyldodecyl myristate, dimer dilinoleyl dimer dilinoleate, polyglyceryl-2 isostearate / dimer dilinoleate, sorbitan sesquiisostearate, polyglyceryl-3 diisostearate, isononyl isononanoate, meadowfoam seed oil, caprylic / capric triglyceride, sunflower oil, dipentaerythrityl tetrahydroxystearate / isostearate, diisostearyl malate, jojoba oil

[0327] Volatile oil

[0328] According to an advantageous embodiment of the invention, the composition does not contain (0%) or very little (maximum 5% by weight relative to the total weight of the composition) volatile oil.

[0329] By "volatile oil" is meant an oil capable of evaporating on contact with the skin in less than one hour, at room temperature and atmospheric pressure.

[0330] The volatile oil is a volatile cosmetic oil, liquid at room temperature, having in particular a non-zero vapor pressure at room temperature and atmospheric pressure, in particular having a vapor pressure of between 0.13 Pa and 40,000 Pa (0.001 to 300 mm Hg), preferably of between 1.3 Pa and 13,000 Pa (0.01 to 100 mm Hg), and even more preferably of between 1.3 Pa and 1,300 Pa (0.01 to 1,000 mm Hg).

[0331] Volatile oils include volatile silicone oils and / or volatile hydrocarbon oils.

[0332] The volatile silicone oils optionally used in the compositions of the invention are linear or cyclic, have in particular from 2 to 7 silicon atoms, optionally alkyl or alkoxy groups having from 1 to 10 carbon atoms, and have a viscosity, at room temperature, of less than 5 cSt.

[0333] As examples of volatile silicone oil, mention may more particularly be made of hexamethylcyclotrisiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, cyclotetradimethylsiloxane, cyclopentadimethylsiloxane, cyclohexadimethylsiloxane, hexamethyldisiloxane, octamethyltrisiloxane, hexylheptamethyltrisiloxane, octylheptamethyltrisiloxane, decamethyltetrasiloxane, dodecamethylpentasiloxane, heptamethylhexamethyltrisiloxane, heptamethyloctyltrisiloxane or a mixture thereof.

[0334] Concerning the volatile hydrocarbon oil, we can more particularly cite a short-chain hydrocarbon oil, volatile linear alkanes such as for example described in document FR2933865.

[0335] Examples of short-chain hydrocarbon oil(s) that may be mentioned include those chosen from the group comprising isododecane, isodecane, isohexadecane, dodecane or one of their mixtures.

[0336] As an example of volatile linear alkanes, we can cite those having hydrocarbon chains in:

[0337] - C9-C17, C10-C14, such as a mixture of undecane and tridecane, marketed by BASF Care Creations under the name Cetiol® Ultimate, - C15-19, such as those marketed by Seppic under the name Emogreen L15, - C12-14, such as those marketed by Biosynthis under the name Vegelight 1214LC, - C9-12 alkane, such as those marketed by Daito under the name Makigreen D10.

[0338] Coloring agent

[0339] The coloring agent may in particular be chosen from water-soluble or liposoluble dyes, pigments, pearlescent agents, lakes or mixtures thereof.

[0340] These coloring agents may optionally be surface-treated with a hydrophobic agent such as silanes, silicones, fatty acid soaps, C9-i5 fluoroalcohol phosphates, acrylate / dimethicone copolymers, mixed C1-i5 fluoroalcohol phosphate / silicone copolymers, lecithins, carnauba wax, polyethylene, chitosan and optionally acylated amino acids such as lauroyl lysine, disodium stearoyl glutamate and aluminum acyl glutamate. The pigments may be mineral or organic, natural or synthetic.

[0341] Examples of mineral pigments include titanium dioxide, zinc oxide, iron, zinc or chromium oxides, manganese violets, ultramarines, ferric ferrocyanide known as Prussian Blue, as well as composite pigments and goniochromatic, pearlescent, interference, photochromic or thermochromic pigments, without this list being limiting.

[0342] Examples of organic pigments that can be used in the invention are in particular carbon black, D&C type pigments, lakes based on cochineal carmine, barium, strontium, calcium or aluminum or even diketopyrrolopyrrole (DPP) described in EP-A-542669, EP-A-787730, EP-A-787731 and WO-A-96 / 08537.

[0343] The nacres may be chosen from those conventionally present in makeup products, such as mica / titanium dioxide. Alternatively, they may be nacres based on mica / silica / titanium dioxide, based on synthetic fluorphlogopite / titanium dioxide (SUNSHINE® from MAPRECOS), calcium sodium borosilicate / titanium dioxide (REFLECKS® from ENGELHARD) or calcium aluminum borosilicate / silica / titanium dioxide (RONASTAR® from MERCK). Bismuth oxychloride may also be mentioned.

[0344] Advantageously, when it contains one or more pigments, the composition according to the invention also contains at least one dispersant such as diisostearyl malate.

[0345] The coloring agents are present in the composition in a content of between 0.1% and 15%, the percentages being percentages by weight relative to the total weight of the composition.

[0346] Charges

[0347] These fillers are preferably colorless or white.

[0348] The particles which constitute it may be porous or not, and may be in various forms, in particular in platelet, spherical or oblong form, whatever the crystallographic form (for example sheet, cubic, hexagonal, orthorhombic, etc.).

[0349] In particular, the filler may be chosen from cellulose, lauroyl lysine, boron nitride, silicone microbeads such as those marketed under the name Tospearl by Toshiba for example, precipitated calcium carbonate, hydroxyapatite, elastomeric polyorganosiloxane particles, glass or ceramic microcapsules, zinc myristate, magnesium myristate, magnesium stearate, magnesium and aluminum silicate such as that marketed under the trade name Neusilin ULF2 by the company Fuji Chemical Industry, starch, a clay or one of their mixtures.

[0350] Among the fillers, we can cite starch, a clay or one of their mixtures.

[0351] The starch can be chosen for example from rice, tapioca, apple starch of earth or corn. Rice starch is preferred, particularly that with the INCI name distarch phosphate marketed under the name "Rice PO4 Naturel" by the company Agrana Starch.

[0352] The clay may be natural or synthetic. It is made lipophilic by treatment with an alkyl ammonium salt such as a C10 to C22 ammonium chloride, for example di-stearyl di-methyl ammonium chloride. It may be chosen from bentonites, in particular hectorites and montmorillonites, beidellites, saponites, nontronites, sepiolites, biotites, attapulgites, and vermiculites. Preferably, the clay is chosen from hectorites. Examples of hectorite include the product sold under the name Bentone 38V CG by the company ELEMENTIS SPECIALTIES (INCI name disteardimonium hectorite) or the product sold under the name Bentone Gel EUG V by the company ELEMENTIS SPECIALTIES.

[0353] Additional Additives

[0354] Apart from the aforementioned constituents, the composition according to the invention may contain various ingredients, such as a UV filter, a vegetable or synthetic butter, a sweetening agent, an antioxidant, a sequestrant, a pH adjuster, a preservative, perfumes, vitamins, moisturizing agents, or a mixture thereof.

[0355] The UV filters may in particular be chosen from organic and inorganic filters or a mixture thereof. As organic filters, mention may in particular be made of dibenzoylmethane derivatives (including butyl methoxydibenzoylmethane), cinnamic acid derivatives (including ethylhexyl methoxycinnamate), salicylates, para-aminobenzoic acids, |3,[3'-diphenylacrylates, benzophenones, benzylidene camphor derivatives, phenylbenzimidazoles, triazines, phenylbenzotriazoles and anthranilic derivatives. As inorganic filters, mention may in particular be made of filters based on mineral oxides in the form of pigments or nanopigments, coated or not, and in particular based on titanium dioxide or zinc oxide.

[0356] The composition according to the invention may also contain one or more sweetening agents such as sorbitol, sucrose, xylitol, acesulfame K and sodium saccharin; antioxidants such as alkylated or phosphorylated esters of ascorbic acid, or tocopherol and its esters; sequestering agents such as EDTA salts; pH adjusters; preservatives; perfumes; vitamins; moisturizing agents; or a mixture thereof.

[0357] Examples of such adjuvants are cited in particular in the CTFA Dictionary (International Cosmetic Ingredient Dictionary and Handbook published by The Cosmetic, Toiletry and Fragrance Association, 11th Edition, 2006).

[0358] Preferably, the cosmetic compositions according to the invention comprise less than 3% by weight of additional solid fatty substances of mineral and / or synthetic origin, in particular less than 1% by weight, and better still absent from the composition are:

[0359] - solid fatty substances chosen from commercially available synthetic beeswax by Koster Keunen under the trade name Kester Wax K82H, or a mixture thereof; polyethylene wax, such as that marketed by New Phase Technologies under the name Performalène 400 (P400) or by Jeen International Corporation under the name Jeenate 3H, a mixture of high molecular weight linear polyethylene and ethylene / propylene copolymer, marketed by Safi-Alcan under the trade name Lipwax® PZ80-20, a synthetic wax such as that marketed by Sasol under the name Sasol Wax C80, mixtures of synthetic waxes and vegetable waxes, such as for example a mixture of synthetic wax and carnauba wax (Copemica cerifera) marketed by Strahl & Pitsch under the name Smart wax 202, a mixture of synthetic wax, Candelilla wax and carnauba wax (Copemica cerifera) marketed by Strahl & Pitsch under the name Smartwax 7743S, Fischer Tropsch waxes such as those marketed by Cirebelle under the name Cirebelle 303, or a mixture thereof, montan wax, ceresins, ozokerites, microcrystalline waxes, mineral paraffins; and

[0360] - Pasty fatty substances chosen from vaselines also called petrolatum.

[0361] Pharmaceutical composition

[0362] According to yet another aspect, the invention relates to a pharmaceutical composition comprising a mixture of linear alkanes according to the invention.

[0363] Use of a mixture of linear alkanes

[0364] According to yet another aspect, the invention relates to the use of a mixture of linear alkanes according to the invention in the field of cosmetics, pharmaceuticals, coatings, inks, varnishes, paper, adhesives, candles, plastics, rubbers and / or food products.

[0365] Specific mixture of terminal olefins

[0366] According to yet another aspect, the invention relates to a mixture of terminal olefins which consists of: - From 1 to 10% by weight of C16 terminal olefins; - From 45 to 49.5% of terminal olefins in Cl8; and - From 45 to 49.5% of C20 terminal olefins;

[0367] This mixture is particularly useful for preparing, according to the process of the invention, a wax of natural origin with physicochemical properties comparable to those of mineral paraffins, notably used in the field of lipsticks.

[0368] Mixture of internal olefins obtained in step ii)

[0369] According to yet another aspect, the invention relates to a mixture of internal olefins of natural origin, in particular of plant origin, capable of being obtained according to steps i) and ii) of the process according to the invention.

[0370] In embodiments, said at least one terminal linear olefin used in step i) of the process is a mixture of C16, C18 and C20 terminal linear olefins.

[0371] In embodiments, the mixture of C16, C18 and C20 terminal linear olefins consists of: - From 1 to 10% by weight of C16 terminal olefins; - From 45 to 49.5% of terminal olefins in Cl8; and - From 45 to 49.5% of C20 terminal olefins;

[0372] This mixture is particularly useful as a synthesis intermediate for preparing the mixture of linear alkanes according to the process of the invention. Examples

[0373] Materials and methods

[0374] Materials

[0375] The mixtures of linear alkanes were prepared from commercial products, such as:

[0376] Ru-2 CAS: 373640-75-6 (M206)

[0377] Ru-3 CAS: 1212008-99-5 (M711)

[0378] The Rula / Rulb catalyst was prepared according to the publication Dalton Trans., 2014, 43, 7044.

[0379] Methods

[0380] Analysis by gas chromatography (GC):

[0381] Gas chromatography makes it possible to determine the different components of a mixture which diffuse at different speeds depending on their affinity with the mobile phase and the stationary phase. The products are thus separated from each other to form a chromatogram. Thanks to calibration lines previously carried out on each of the isolated compounds, these can thus be quantified. The samples were prepared at known concentrations in vials and passed on a Shimadzu GC-2014 device with an Agilent VF-5ht column having the following characteristics: 30m X 0.25mm X 0.10pm, maximum temperature: 430°C. A temperature gradient is used during the analysis:

[0382] [Tableauxl] Speed ​​(°C / min) Temperature (°C) Holding time (min) - 80 5 10 360 5 2 400 10

[0383] Analysis time: 68 min

[0384] Analysis by gas chromatography coupled with mass spectrometry (GC / MS):

[0385] This technique combines gas chromatography (explained previously) and mass spectrometry which allows the determination of the molecular masses of the analyzed compounds according to their mass / charge ratio. The samples were prepared in vials and passed on a Shimadzu GC-2010 Plus device with a Shimadzu SH-Rxi-5ms column having the following characteristics: 30m X 0.25mm X 0.25pm, maximum temperature: 330°C. A temperature gradient is used during the analysis:

[0386] [Tables2] Speed ​​(°C / min) Temperature (°C) Holding time (min) - 70 4 10 250 10

[0387] Analysis time: 32 min

[0388] Nuclear Magnetic Resonance (NMR) Analysis:

[0389] The synthesized molecules are characterized by Nuclear Magnetic Resonance (NMR) spectrometry. The NMR spectra were recorded on a Bruker ARX400 device (*H: 400 MHz, 13C: 101 MHz, 31P: 162 MHz). Solvent: CDC13.

[0390] Analysis by DSC (Differential Scanning Calorimetry):

[0391] The synthesized waxes, the formulated solid compositions including the lipsticks are analyzed by a DSC 25 device from the TA Instruments brand in order to know precisely their fusion profile.

[0392] Polymorphism protocol 100°C (temperature gradient):

[0393] DSC is a thermal analysis technique that measures the differences in heat exchange between a reference and a sample to be analyzed. It allows us to know:

[0394] - the melting point of the samples,

[0395] - the melting start temperature, desired to be as high as possible to limit the risks of exudation and thermal instability

[0396] - the temperature of 100% melt, to establish the industrial process temperature in ensuring that the crystals are completely melted.

[0397] - enthalpy, which corresponds to the energy required to melt the crystals of wax. The highest possible enthalpy is desirable to maximize the quantity of crystals and allow for a harder stick.

[0398] Solid fatty substances and crystals more generally can sometimes exhibit what is called polymorphism. Polymorphism corresponds to the possibility of forming different types of crystals depending on external conditions (cooling rate or storage time for example). Thus, these different types of crystals, which can coexist, are characterized by different melting points, densities, plasticities, etc. For certain waxes, the cooling rate impacts the crystals formed. It is essential to avoid waxes exhibiting this type of polymorphism for the sake of stability and repeatability of industrial batches. Polymorphism can be anticipated from the DSC profile by subjecting the sample to successive coolings at different rates.

[0399] All of these parameters are evaluated using a differential scanning calorimeter (DSC 25, Discovery DSC Series, TA Instruments, France) connected via a computer to the Trios software (TA Instruments, France) allowing the measurements to be launched and the spectra obtained to be analyzed. For each candidate, 11 + / - 0.5 mg of wax are taken and introduced into a standard crucible, sealed using a crimper (Tzero Sample Press, TA Instruments, France). The program follows the following protocol: first heating to erase the thermal past of the raw material (5°C / min from 15°C to 120°C), followed by slow cooling (2°C / min from 120°C to -5°C), a second heating (5°C / min from -5°C to 120°C), rapid cooling (25°C / min from 120°C to -5°C), then a final heating (5°C / min from -5°C to 120°C). Comparison of the profiles of the second and third heatings allows conclusions to be drawn as to the polymorphism or not of each raw material.For all syntheses, two samples are prepared to ensure repeatability of measurements.

[0400] Texturometer:

[0401] Lipstick hardness study:

[0402] The butter cutter test allows a rapid assessment of the firmness of a lipstick by measuring in particular the cutting resistance of the stick product. This measurement is carried out 24 hours after formulation, using a texturometer (TAXTPlus, MicroStable Systems, United Kingdom) equipped with a 5 kg force cell and its Butter Cutter A / BC probe (Swantech, MicroStable Systems, United Kingdom). It allows the maximum resistance force of the stick to be measured when the butter cutter penetrates to a depth of 9 mm at a speed of 1.6 mm / s. To ensure the reproducibility of the measurements, the analysis is repeated on 6 sticks and the relative deviation between the measurements must not be greater than 10%, ideally 5%.

[0403] Example 1: Synthesis of a mixture of linear alkanes of natural origin from a mixture of terminal linear olefins - Hard wax A (melting temperature = 80°C)

[0404] The process according to the invention comprises three stages: olefin metathesis - isomerizing olefin metathesis - hydrogenation ([Fig.l]). It makes it possible to obtain a mixture of alkanes from a mixture of terminal olefins.

[0405] Terminal olefins can be prepared according to known synthetic methods (Cf. [Fig.2], [Fig.3]).

[0406] Step 1: Olefin metathesis involving a mixture of terminal olefins

[0407] A cross metathesis reaction carried out on 3 terminal olefins composed respectively of 16, 18 and 20 carbons of plant origin in the presence of Ruthenium catalysts allows the production of a mixture of internal olefins ranging from C30 to C38 [Fig.4].

[0408] Protocol

[0409] In a two-necked flask equipped with a magnetic bar and a condenser, the mixture of terminal olefins Ci6 (0.01 eq, 786 mg), Ci8 (0.495 eq, 43.74 g) and C20 (0.495 eq, 48.6 g) is charged and heated under vacuum to 80 ° C. After 1 hour the catalyst (Ru-1a / Ru-1b 3 / 7, 0.3 mol%, 953 mg) is added under argon as well as the distilled solvent (THF, 8.75 mL). The mixture is then stirred at 75 ° C for two days. The reaction is hydrolyzed with ethyl vinyl ether and the reaction mixture is purified by chromatography on silica gel with hot cyclohexane to remove the remaining catalyst. Cold filtration to remove the last traces of catalyst is carried out with acetone to give the desired product (50.6g) in the form of a white powder.

[0410] NMR

[0411] 1H NMR analysis (CDC13 solvent) shows the appearance of olefinic protons from the terminal olefin as well as the complete disappearance of the terminal olefinic protons. Analysis of the final product by gas chromatography shows a mixture of olefins composed of 30 to 38 carbons.

[0412] Step 2: Isomerizing olefin metathesis

[0413] The isomerizing olefin metathesis reaction in the presence of a duo of ruthenium catalysts [Fig.5] gives access to a mixture of internal olefins. A gas chromatographic analysis made it possible to determine the composition of this mixture with the obtaining of a distribution of internal olefins comprising from 24 to 60 carbons ([Fig.6]).

[0414] Protocol

[0415] In a two-necked flask, equipped with a magnetic bar and a condenser, the internal olefin mixture (60g) is introduced and heated under vacuum at 80°C for 1 hour. The catalysts (Ru-2, 0.5mol%, 555mg and Ru-3, 1mol%, 977mg) are then added under argon as well as the distilled solvent (THF, 90mL) and methanol (5mL). The mixture is stirred at 75°C for 2 hours. The reaction is hydrolyzed with ethyl vinyl ether and the crude mixture is purified by silica gel chromatography with hot cyclohexane to remove the remaining catalyst. Cold filtration to remove the last traces of catalyst is carried out with acetone to give the desired product (59.8g) in the form of a white powder.

[0416] Step 3: Hydrogenation

[0417] The hydrogenation of the mixture of internal olefins previously obtained in the presence of palladium on carbon was then studied [Fig.7] and allowed the production of a mixture of alkanes comprising 24 to 60 carbons.

[0418] Protocol

[0419] In a flask under argon equipped with a magnetic bar, the mixture of internal olefins (48.1g), the catalyst (Pd / C, 1.9g; 0.4% wt Pd / substrate) and the solvent (cyclohexane, 240mL) are introduced. The reaction is heated to 50°C and purged 3 times under H2. The mixture is left stirring at 50°C for 16 hours under 1 bar of hydrogen. The reaction medium is filtered through a frit with hot cyclohexane and then concentrated using a rotary evaporator. Cold filtration with acetone to remove the last traces of catalyst is carried out to give the desired product (45g) in the form of a white powder with a mass yield of 93%.

[0420] NMR

[0421] *H NMR analysis (CDCl3) of the final mixture shows the absence of olefinic protons around δ=5.4 ppm, which confirms that we have a mixture of alkanes.

[0422] CPG

[0423] Analysis of the reaction mixture by GC ([Fig.8]) confirms the presence of the mixture of alkanes and made it possible to determine the exact composition of the mixture in the form of a distribution containing from 24 to 60 carbons. This mixture is designated “Wax A”.

[0424] DSC

[0425] DSC thermogravimetry analysis shows that the melting temperature and enthalpy are very close to those of Lipwax® PZ80-20 with respective values ​​of 79.2 vs 80.6°C and 225 vs 212 J / g. In addition, the "onset point", which determines the initial melting point of the wax, is lower than that of Lipwax® PZ80-20 (55.4 vs 63.5°C) and the melting temperature of the last alkane composing the mixture ("endset point") is higher for Wax A (91.7 vs 89.9°C), which implies that the range of alkane in Wax A is greater than that of Lipwax® PZ80-20.

[0426] Example 2: Synthesis of a mixture of linear alkanes of natural origin from a terminal linear olefin - Soft wax B (melting temperature = 48°C)

[0427] From jojoba oil (Flora esters® marketed by Floratech), it is possible to carry out ethenolysis without going through isomerization. The product of this synthesis, dec-l-ene, can then be engaged in a sequential process of metathesis / isomerizing metathesis / hydrogenation [Fig. 10] to obtain a mixture composed of alkanes ranging from C17 to C44.

[0428] Protocol

[0429] The bleached jojoba oil (1g) is loaded into a vial fitted with a magnetic stir bar and a septum. The oil is heated at 180°C for 2h under vacuum. Vacuum-argon purges are performed. The catalyst is added as a solution (Ru-4, 1mg / mL in dichloromethane, 120pL, 0.01mol%) under argon. The septum is removed quickly and the vial is placed in an autoclave. Ethylene purges (purity = 99.95%) are carried out and the mixture is stirred at 10 bar of ethylene for 6 hours at 40°C. The reaction is hydrolyzed with ethyl vinyl ether and the product is analyzed by GC with trimethoxybenzene as an internal standard. The conversion is 98% and the product obtained is mainly dec-l-ene.

[0430] Decene (1g; 7.13mmol) is loaded into a Schlenk flask equipped with a magnetic bar. Quick vacuum-argon purges are performed and the catalyst (Ru-1a / Ru-1b 3 / 7, 0.3mol%, 19.4mg) is added under argon as well as the distilled solvent (THF, 7mL). The mixture is then stirred at 75°C for four days. The reaction is hydrolyzed with ethyl vinyl ether and the solvent is removed under reduced pressure. The product is purified by silica gel chromatography with hot cyclohexane to remove the remaining catalyst. The product obtained (554mg) is a light yellow liquid with a mass yield of 62% and is analyzed by GC and GC-MS.

[0431] In a two-necked flask, equipped with a magnetic bar and a condenser, the internal olefin mixture (500mg) is introduced and heated under vacuum at 80°C for 1 hour. The catalysts Ru-2 (9.2mg; 0.5mol%) and Ru-3 (16.3mg; 1mol%) are then added under argon as well as the distilled solvent (THF, 2.8mL) and methanol (82pL). The mixture is stirred at 75°C for 2 hours. The reaction is hydrolyzed with ethyl vinyl ether and the crude mixture is purified by silica gel chromatography with hot cyclohexane to remove the remaining catalyst to give the desired product (476mg) in the form of a light yellow paste with a mass yield of 95%.

[0432] The mixture of internal olefins (350mg) and the catalyst (Pd / C, 14mg; 0.4% wt Pd / substrate) are introduced into a microwave tube equipped with a magnetic bar and heated under vacuum at 50°C. The solvent (cyclohexane, 1.75mL) is added under argon. Vacuum-hydrogen purges are carried out (3 times). The mixture is left to bubble under hydrogen at 1 atm for 30 seconds and the mixture is then stirred at 50°C for 6h at 1 atmosphere of hydrogen. The crude mixture is purified by silica gel chromatography with hot cyclohexane. After removal of the solvent under vacuum, cold filtration with acetone to remove the last traces of catalyst is carried out to give the desired product in the form of a white powder with a mass yield of 59%. The product is analyzed by GC and 'H NMR.

[0433] NMR

[0434] 'H NMR analysis (CDCl3) of the final mixture shows the absence of olefinic protons around δ=5.4 ppm which confirms that we have a mixture of alkanes.

[0435] CPG

[0436] Analysis of the reaction mixture by CPG [Fig.l 1] confirms the presence of a mixture in the form of a Gaussian composed of alkanes containing 17 to 44 carbons.

[0437] DSC

[0438] DSC thermogravimetry analysis shows a melting temperature and enthalpy equal to 47.9°C and 133 J / g respectively. The "onset point" is obtained at 36.1°C and the "endset point" at 58°C.

[0439] Example 3: Synthesis of a mixture of linear alkanes of natural origin from a mixture of terminal linear olefins - Hard wax C (melting temperature = 75°C)

[0440] From a mixture of terminal olefins, it is possible to obtain a mixture of alkanes ranging from C22 to C54 according to a sequential process of metathesis / isomerizing metathesis / hydrogenation. The final product has the particularity of having a melting point equal to 75°C. [Fig.l 1]

[0441] Protocol

[0442] In a schlenk equipped with a magnetic bar, the mixture of terminal olefins Ci6 (0.01 eq, 11mg), Ci8 (0.495 eq, 625mg), C2o (0.495 eq, 694mg) and the catalyst (Ru-la, 32mg) are loaded. Under argon, the mixture is heated to 80°C. Hydrochloric acid in ethyl acetate (3mL) is added. The mixture is then stirred at 80°C for 2 hours. A few milligrams of catalyst (30mg) and hydrochloric acid in ethyl acetate (5mL) are added and the mixture is stirred at 80°C for 2 hours. Again, a few milligrams of catalyst (30 mg) and hydrochloric acid in ethyl acetate (2 mL) are added and the mixture is stirred at 80 ° C for 2 hours. The catalyst is neutralized, in particular by adding an alkyl vinyl ether to the reaction mixture. The product is purified by chromatography on silica gel with hot cyclohexane to remove the remaining catalyst.The product obtained (81 Img) is a white solid with a mass yield of 61% and is analyzed by CPG and 'H NMR.

[0443] In a two-necked flask, equipped with a magnetic bar and a condenser, the mixture of internal olefins (300mg) and the catalyst (Ru-2, 0.5mol%, 3mg) are introduced and heated under vacuum at 80°C for 20 minutes. The distilled solvent (THF, 0.6mL) as well as methanol (100pL) are then added under argon. The mixture is stirred at 80°C overnight. The catalyst is neutralized with ethyl vinyl ether and the crude mixture is purified by silica gel chromatography with hot cyclohexane to remove the remaining catalyst. The desired product (300mg) is obtained as a white solid with a mass yield of 99% and is analyzed by GC.

[0444] The mixture of internal olefins (260mg) and the catalyst (1.2mL; 50% wt Raney Nickel) are introduced into an autoclave equipped with a magnetic bar and heated to 110°C. Hydrogen purges are carried out (3 times). The autoclave is filled with 25 bar of hydrogen. The mixture is stirred at 110°C overnight at 25 bar of hydrogen. The crude mixture is purified by chromatography on silica gel with hot cyclohexane. After removal of the solvent under vacuum, the desired product (260 mg) is obtained in the form of a white powder with a mass yield of 99%. The product is analyzed by 'H NMR, GC and DSC.

[0445] NMR

[0446] 'H NMR analysis (CDCl3) of the final mixture shows the absence of olefinic protons around δ=5.4 ppm which confirms that we have a mixture of alkanes.

[0447] CPG

[0448] Analysis of the reaction mixture by CPG [Fig. 12] confirms the presence of a mixture composed of alkanes containing from 22 to 54 carbons.

[0449] DSC

[0450] DSC thermogravimetry analysis shows a melting temperature and enthalpy equal to 75.2°C and 214 J / g respectively. The "onset point" is obtained at 66.9°C and the "endset point" at 79.2°C.

[0451] Example 4: Synthesis of a mixture of linear alkanes of natural origin from a mixture of linear terminal olefins in C6, C7 and C8 - Pasty D (melting temperature = 31.5°C)

[0452] From a mixture of terminal olefins, it is possible to obtain a mixture of alkanes ranging from C12 to C47 according to a sequential process of metathesis / isomerizing metathesis / hydrogenation. The final product obtains a melting point equal to 31.5°C. [Fig.13].

[0453] Protocol

[0454] The catalyst (Ru-la, 27mg) is loaded into a two-necked flask equipped with a magnetic stir bar and a condenser. Under argon, the terminal olefins C6 (0.33 eq, 737pL), C7 (0.33 eq, 836pL) and C8 (0.33 eq, 933pL) are added. The mixture is heated to 75°C. Hydrochloric acid in ethyl acetate (2mL) is added. The mixture is then stirred at 75°C for 24 hours. A few milligrams of catalyst (14mg) and hydrochloric acid in ethyl acetate (ImL) are added and the mixture is stirred at 75°C for 20 hours. Again, a few milligrams of catalyst (14 mg) and hydrochloric acid in ethyl acetate (1 ml) are added and the mixture is stirred at 75°C for 6 hours. The catalyst is neutralized, in particular by adding an alkyl vinyl ether to the reaction mixture. The product is purified by chromatography on silica gel with pentane to remove the remaining catalyst.The product obtained (1.1g) is a light yellow liquid with a mass yield of 63% and is analyzed by GC and 'H NMR.

[0455] In a two-necked flask, equipped with a magnetic bar and a condenser, the mixture of internal olefins (550mg) is introduced and heated under vacuum at 75°C for 10 minutes. The catalysts Ru-2 (42mg; 0.5mol%) and Ru-3 (73mg; 1mol%) are then added under argon as well as the distilled solvent (THF, 9mL) and methanol (200pL). The mixture is stirred at 75°C for 2 hours. The catalyst is neutralized with ethyl vinyl ether and the crude mixture is purified by silica gel chromatography with hot cyclohexane to remove the remaining catalyst. The desired product (404mg) is obtained in the form of a light yellow paste with a mass yield of 74% and is analyzed by GC.

[0456] The mixture of internal olefins (300mg) and the catalyst (Pd / C, 12mg; 0.4% wt Pd / substrate) are introduced into a microwave tube equipped with a magnetic bar and heated under vacuum at 50°C. The solvent (cyclohexane, 1.5mL) is added under argon. Vacuum-hydrogen purges are carried out (3 times). The mixture is left to bubble under hydrogen at 1 atm for 30 seconds and the mixture is then stirred at 50°C for 16h at 1 atmosphere of hydrogen. The crude mixture is purified by chromatography on silica gel with hot cyclohexane. The product (278mg) is obtained in the form of a white paste with a mass yield of 93%. The product is analyzed by 'H NMR, GC and DSC.

[0457] NMR

[0458] 'H NMR analysis (CDCl3) of the final mixture shows the absence of olefinic protons around δ=5.4 ppm which confirms that we have a mixture of alkanes.

[0459] CPG

[0460] Analysis of the reaction mixture by GC [Fig. 13] confirms the presence of a mixture composed of alkanes containing 12 to 47 carbons.

[0461] DSC

[0462] DSC thermogravimetry analysis shows a melting temperature and enthalpy equal to 31.5°C and 195 J / g respectively. The endset point is obtained at 56.8°C.

[0463] Example 5 - Synthesis of a mixture of linear alkanes of natural origin from a mixture of terminal linear olefins in C8, C9 and CIO - Pasty E (melting temperature = 37°C)

[0464] From a mixture of terminal olefins, it is possible to obtain a mixture of alkanes ranging from Cl 1 to C50 according to a sequential process of metathesis / isomerizing metathesis / hydrogenation. The final product obtains a melting point equal to 37°C. [Fig.14]

[0465] Protocol

[0466] The catalyst (Ru-la, 20mg) is loaded into a two-necked flask equipped with a magnetic stir bar and a condenser. Under argon, the terminal olefins C8 (0.33 eq, 700pL), C9 (0.33 eq, 771pL) and Cio (0.33 eq, 844pL) are added. The mixture is heated to 75°C. Hydrochloric acid in ethyl acetate (ImL) is added. The mixture is then stirred at 75°C for 15 hours. A few milligrams of catalyst (10mg) and hydrochloric acid in ethyl acetate (ImL) are added and the mixture is stirred at 75°C for 10 hours. Again, a few milligrams of catalyst (10 mg) and hydrochloric acid in ethyl acetate (1 ml) are added and the mixture is stirred at 75°C for 15 hours. The catalyst is neutralized, in particular by adding an alkyl vinyl ether to the reaction mixture. The product is purified by chromatography on silica gel with pentane to remove the remaining catalyst.The product obtained (1.36g) is a light yellow liquid with a mass yield of 81% and is analyzed by GC and 'H NMR.

[0467] In a two-necked flask, equipped with a magnetic bar and a condenser, the mixture of internal olefins (679mg) is introduced and heated under vacuum at 75°C for 10 minutes. The catalysts Ru-2 (31mg; 0.5mol%) and Ru-3 (55mg; 1mol%) are then added under argon as well as the distilled solvent (THF, 7mL) and methanol (200pL). The mixture is stirred at 75°C for 2 hours. The catalyst is neutralized with ethyl vinyl ether and the crude mixture is purified by silica gel chromatography with hot cyclohexane to remove the remaining catalyst. The desired product (600mg) is obtained in the form of a light yellow paste with a mass yield of 88% and is analyzed by GC.

[0468] The mixture of internal olefins (450mg) and the catalyst (Pd / C, 18mg; 0.4% wt Pd / substrate) are introduced into a microwave tube equipped with a magnetic bar and heated under vacuum at 50°C. The solvent (cyclohexane, 2.25mL) is added under argon. Vacuum-hydrogen purges are carried out (3 times). The mixture is left to bubble under hydrogen at 1 atm for 30 seconds and the mixture is then stirred at 50°C for 16h at 1 atmosphere of hydrogen. The crude mixture is purified by chromatography on silica gel with hot cyclohexane. The product (438mg) is obtained in the form of a white paste with a mass yield of 97%. The product is analyzed by 'H NMR, GC and DSC.

[0469] NMR

[0470] *H NMR analysis (CDCl3) of the final mixture shows the absence of olefinic protons around δ=5.4 ppm, which confirms that we have a mixture of alkanes.

[0471] CPG

[0472] Analysis of the reaction mixture by GC [Fig. 14] confirms the presence of a mixture composed of alkanes containing 11 to 50 carbons.

[0473] DSC

[0474] DSC thermogravimetry analysis shows a melting temperature and enthalpy equal to 37°C and 208 J / g respectively. The endset point is obtained at 63.6°C.

[0475] Example 6: Synthesis of a mixture of linear alkanes of natural origin from a mixture of terminal linear olefins in CIO, C12 and C14 - Soft wax F (T “melting = 57°C)

[0476] From a mixture of terminal olefins, it is possible to obtain a mixture of alkanes ranging from Cl 1 to C54 according to a sequential process of metathesis / isomerizing metathesis / hydrogenation. The final product obtains a melting point equal to 57°C. [Fig.15]

[0477] Protocol

[0478] The catalyst (Ru-la, 19mg) is loaded into a two-necked flask equipped with a magnetic stir bar and a condenser. Under argon, the terminal olefins Cio (0.33 eq, 810pL), Ci2 (0.33 eq, 950pL) and Cu (0.33 eq, 1085pL) are added. The mixture is heated to 75°C. Hydrochloric acid in ethyl acetate (ImL) is added. The mixture is then stirred at 75°C for 15 hours. A few milligrams of catalyst (10mg) and hydrochloric acid in ethyl acetate (ImL) are added and the mixture is stirred at 75°C for 10 hours. Again, a few milligrams of catalyst (10 mg) and hydrochloric acid in ethyl acetate (1 ml) are added and the mixture is stirred at 75°C for 15 hours. The catalyst is neutralized, in particular by adding an alkyl vinyl ether to the reaction mixture. The product is purified by chromatography on silica gel with pentane to remove the remaining catalyst.The product obtained (2.03g) is a light yellow liquid with a mass yield of 94% and is analyzed by GC and 'H NMR.

[0479] In a two-necked flask, equipped with a magnetic bar and a condenser, the mixture of internal olefins (1.01g) is introduced and heated under vacuum at 75°C for 10 minutes. The catalysts Ru-2 (30mg; 0.5mol%) and Ru-3 (53mg; 1mol%) are then added under argon as well as the distilled solvent (THF, 6.5mL) and methanol (200pL). The mixture is stirred at 75°C for 2 hours. The catalyst is neutralized with ethyl vinyl ether and the crude mixture is purified by silica gel chromatography with hot cyclohexane to remove the remaining catalyst. The desired product (963mg) is obtained in the form of a light yellow paste with a mass yield of 95% and is analyzed by GC.

[0480] The mixture of internal olefins (430mg) and the catalyst (Pd / C, 17mg; 0.4% wt Pd / substrate) are introduced into a microwave tube equipped with a magnetic bar and heated under vacuum at 50°C. The solvent (cyclohexane, 2.15mL) is added under argon. Purge Vacuum-hydrogen gases are carried out (3 times). The mixture is left to bubble under hydrogen at 1 atm for 30 seconds and the mixture is then stirred at 50°C for 16 hours at 1 atmosphere of hydrogen. The crude mixture is purified by chromatography on silica gel with hot cyclohexane. The product (410 mg) is obtained in the form of a white paste with a mass yield of 95%. The product is analyzed by 'H NMR, GC and DSC.

[0481] NMR

[0482] 'H NMR analysis (CDCl3) of the final mixture shows the absence of olefinic protons around δ=5.4 ppm which confirms that we have a mixture of alkanes.

[0483] CPG

[0484] Analysis of the reaction mixture by GC [Fig. 15] confirms the presence of a mixture composed of alkanes containing 11 to 54 carbons.

[0485] DSC

[0486] DSC thermogravimetric analysis shows a melting temperature and enthalpy equal to 57°C and 212 J / g respectively. The endset point is obtained at 72°C.

[0487] Example 7: Formulation of lipsticks

[0488] Protocol

[0489] The lipstick formulation in Table 3 was prepared as follows: All the raw materials making up the white body, including the wax with a melting point of 85°C obtained according to Example 1, are melted at 90°C with stirring at approximately 250 rpm. When the mixture is homogeneous and clear, the previously ground pigments are incorporated into the Lexfeel 700. Stirring is increased to 350 rpm for 10 min and then increased to 250 rpm for 5 min. The pearlescent particles are incorporated. Mixing is continued for 5 min. The antioxidant and perfume - if present - are added and stirring is maintained for 5 min. The mixture is poured into molds at 85°C.

[0490] Place the molds at -20°C for 10 minutes and then remove from the mold.

[0491] Stability tests could be carried out on the lipsticks. Different sticks of The lipsticks were incubated at different temperatures (4°C, 20°C, 40°C and 45°C). The lipsticks were then observed at D+1, D+15, D+30 and D+60. The lipsticks formulated with Wax A maintained their good hold, their gliding effect and their shine throughout the incubation.

[0492] The formulations of Lipwax® PZ80-20 and Wax A lipsticks were subjected to hardness tests (butter wire test). The results of these rheological tests are excellent since the measured hardness of the lipsticks formulated with Wax A are similar to those of the lipsticks formulated with Lipwax® PZ80-20 (160g vs 150g respectively).

[0493] Exudation tests were also carried out. Exudation is a seepage phenomenon resulting in the appearance of oily rises to the surface of the anhydrous product in the form of micro-pitting, droplets, oily areas, etc. For this test, 4 lipsticks are positioned at different temperatures (27°C, 30°C, 35°C and 45°C) and are examined after 1 hour, 4 hours and 24 hours of waiting to determine whether seepage is visible. No exudation phenomenon was observed with the lipsticks formulated with Wax A, just like those formulated with Lipwax® PZ80-20.

[0494] Finally, a DSC analysis made it possible to compare the lipsticks containing Lipwax® PZ80-20 or Wax A. According to the thermograms, the melting point of these lipsticks is very close (73°C with Wax A vs 73.7°C with Lipwax® PZ80-20). The “onset point” (33.5 vs 33°C), the “endset point” (92.5 vs 91.2°C) as well as the enthalpy (25.25 vs 25.19 J / g) are equivalent.

[0495] [Tables3] INCI Name Trade Name / Internal Name (%) WHITE BODY WAX MELTING POINT 80°C (Hard Wax A) Obtained according to the process described in Example 1 12 WHITE BODY Additional wax HYDROGENATED CASTOR OIL & AQUA CASTORWAX MP 80 0.200000 WHITE BODY Non-volatile oil SQUALANE NEOSSANCE SQUALA NE 7.000000 WHITE BODY Non-volatile oil OCTYLDODECANOL EUTANOL G 11.00000 0 WHITE BODY Additional fat melting point between 25°C -55°C HYDROGENATED COCONUT OIL HYDROBASE 32-34 3.200000 WHITE BODY Non-volatile oil POLYGLYCERYL-2 TRIISOSTEARATE SALACOS 43N 3.500000 BODY WHITE Non-volatile oil POLYGLYCERYL-10 DECAISOSTEARATE S-FACE IS-1009P 7.000000 BODY B LANC Clay dispersed in non-volatile oils OCTYLDODECANOL & DISTEARDIMONI UM HECTORITE & P ROPYLENE CARBO NATE BENTONE GEL EUG V 8.000000 BODY B LANC film-forming DEXTRIN ISOSTEAR ATE & C8-12 ACID T RIGLYCERIDE TPA-UNIFILMA HVY (7 5%) 4.000000 BODY B Film-forming LANC SHOREA ROBUSTA RESIN & OCTYLDO DECANOL KAHLRESIN 6723 4.000000 Pigment dispersant PENTAERYTHRITYL ADIPATE / CAPRATE / CAPRYLATE / HEPTA NOATE LEXFEEL 700 EX-LO MB 4.230000 Pigment grinding PENTAERYTHRITYL ADIPATE / CAPRATE / CAPRYLATE / HEPTA NOATE CI 15850 (RED 7 LAK E) BR C19003 A 30% DS L EXFEEL 700 13.87000 0 Pigment grinding PENTAERYTHRITYL ADIPATE / CAPRATE / CAPRYLATE / HEPTA NOATE ALUMINUM HYDRO XIDE CI 77891 (TITANIUM DIOXIDE) BR W877 A 65% DS LE CI 17200 (RED 33 LA KE) Grinding of PENTAERYTHRITYL pigments ADIPATE / CAPRATE / CAPRYLATE / HEPTA NOATE CI 15985 (YELLOW 6 LAKE) BR FDC YELLOW 6 A 3 5% DS LEXFEEL 700 7.700000 Grinding of PENTAERYTHRITYL pigments ADIPATE / CAPRATE / CAPRYLATE / HEPTA NOATE ALUMINUM HYDRO TOCOPHEROL & GL YCINE SOJA (SOYBE AN) OIL BIOXAN T 90 0.100000

[0496] A lipstick stick is obtained which has adequate stability and hardness: the stick is sufficiently rigid and solid, does not break during application and is thus compatible with packaging in a stick or in another solid form and with application by friction on the surface to be made up; the stick is also characterized by ease of application such as good glide, good deposit from the first application and a comfortable texture.

[0497] Example 8: Perfumed formula

[0498] The formulation according to Table 4 is prepared as follows: All the raw materials are weighed except the cellulose powder, the sorbitan sesquiisostearate and the perfume. The raw materials are heated to 70°C with stirring. When the mixture is completely melted, clear and homogeneous, the cellulose is added and then the Sorbitan Sesquiisostearate, still with stirring. The temperature is lowered to 65°C while continuing to stir. At 65°C, add the perfume. Homogenize and pour into cups at 65°C.

[0499] [Tables4] INCI Name Trade Name / Internal Name (%) WAX MELTING POINT 75°C (Hard Wax C) Obtained according to Example 3 14 Non-volatile oil DICAPRYLYL CARBONATE AND TOCOPHEROL CETIOL CC 20 Non-volatile oil OCTYLDODECYL MYRISTATE MOD MB 11.25 Additional Paste BIS-BEHENYL / ISOSTEARYL / P HYTOSTEARYL DIMER DILINO LEYL DIMER DILINOLEATE PLANDOOL-G 10 Non-volatile oil DIMER DILINOLEYL DIMER DI LINOLEATE LUSPLAN DD-D A7 5 Non-volatile oil POLYGLYCERYL-2 ISOSTEARA TE / DIMER DILINOLEATE COP OLYMER HAILUCENT IS DA-MB 5 Antioxidant TOCOPHERYL ACETATE 0.5 preservative CAPRYLYL GLYCOL DERMOSOFT O CTIOL 0.25 filler CELLULOSE CELLULOBEAD SUSF 12 Non-volatile oil SORBITAN SESQUIISOSTEARA TE SALACOS 182 V 2 FRAGRANCE 20

[0500] A solid perfumed formula is obtained which has adequate stability and hardness: the composition is sufficiently rigid and solid, it does not exude over time and does not have surface heterogeneities and is thus compatible with packaging in solid form cast in a cup and with application by friction on the surface to be perfumed; the composition is also characterized by ease of application such as good glide, good deposit from the first application and a comfortable texture.

[0501] Example 9: Lip Gloss Formula

[0502] The formula in Table 5 was prepared as follows: The white body composed of wax A with a melting point of 80°C obtained according to Example 1, Cithrol PG 32 IS, isononyl isononanoate, dextrin palmitate and sucrose acetate isobutyrate is weighed and heated to 98°C with stirring at 150 rpm. When everything is melted, the temperature is lowered to 95°C. The nacres are weighed and added and incorporated with stirring at 250 rpm. Stirring is lowered to 150 rpm to de-bubble. The antioxidant is weighed and added. The temperature is lowered to 90°C (plus or minus 2°C). It is drained and poured into cups at 90°C. After 10 minutes at room temperature, the cups are placed at -19°C for 10 minutes.

[0503] [Tables5] INCI Name Trade Name 1 / Internal Name (%) WHITE BODY WAX MELTING POINT 80°C (Hard Wax A) Obtained according to T example 1 8 WHITE BODY Pigment Dispersant POLYGLYCERYL-3 DIISOSTE ARATE CITHROL PG3 2IS-LQ-(MV) 56.60000 0 WHITE BODY Non-volatile Oil ISONONYL ISONONANOATE DUB ININ A 19.00000 0 WHITE BODY Lipophilic Gelling Agent DEXTRIN PALMITATE RHEOPEARL KL 2 8.000000 WHITE BODY Film-forming SUCROSE ACETATE ISOBUT YRATE EASTMAN SA IB-100 4.000000 Pearlescent CALCIUM ALUMINUM BORO SILICATE & CI 77891 (TITANIUM DIOXIDE) & TIN OXIDE PEARLS 4.100000 Anti-oxidant TOCOPHERYL ACETATE DL-ALPHA-TO COPHERYL A CETATE 0.300000

[0504] A solid lip gloss cast in a pan is obtained which has adequate stability and hardness: the composition is sufficiently rigid and solid, it does not exude over time and does not have surface heterogeneities and is thus compatible with packaging in solid form in a pan and with application by friction on the surface to be made up; the composition is also characterized by ease of application such as good glide, good deposit from the first application and a comfortable texture.

[0505] Example 10: Lip balm formula

[0506] The formula in Table 6 was prepared as follows: Weigh all the raw materials of the formula: S-Face, Eutanol G, Super Sterol Esters, Bentone gel, wax with a melting point of 80°C obtained according to Example 1, paste with a melting point of 37°C obtained according to Example 5, squalane, Salacos 43V and Shea butter. Do not include the pearlescent agents, pigments and their dispersing oil, active ingredients, perfume and antioxidant. Heat to 90°C with stirring at 250 rpm. When everything is melted, weigh and add the pigments previously ground in their dispersing oil. Mix for 10 minutes with stirring at 250 rpm. Incorporate the pearlescent agents with stirring at 250 rpm. Reduce stirring to 150 rpm to de-bubble. Weigh and add the antioxidant, active ingredients, and fragrance. Mix for 5 minutes at 150 rpm. Pour into molds at 90°C. Wait 10 minutes at room temperature, level off, and then place the molds at -19°C for 10 minutes.Wait 2 minutes at room temperature and unmold.

[0507] [Tableauxô] INCI Name Trade Name / Internal Name (%) Non-volatile oil POLYGLYCERYL-10 DECAISOSTEA RATE S-FACE IS-1009 P 12.800000 Non-volatile oil OCTYLDODECANOL EUTANOL G 10.000000 Additional paste C10-30 CHOLESTEROL / LANOSTER OL ESTERS SUPER STEROL ESTER-SO (JP) 10.000000 clay OCTYLDODECANOL & DISTEARDI MONIUM HECTORITE & PROPYLENE CARBONATE BENTONE GEL EUGV 10.000000 WAX MELTING POINT 80°C (hard wax A) Obtained according to Example 1 9.500000 Pigment dispersant PENTAERYTHRITYL ADIPATE / CAP RATE / CAPRYLATE / HEPTANOATE LEXFEEL 700 E X-LO MB 7.900000 Non-volatile oil SQUALANE NEOSSANCE S QUALANE 7.000000 Non-volatile oil POLYGLYCERYL-2 TRIISOSTEARA TE SALACOS 43V( MB) -SALACO S 43V 6,500000 pearls MICA & TITANIUM DIOXIDE & IRO N OXIDES PEARLS 2,000000 PASTY MELTING POINT 37° (Pasty E ) Obtained according to example 5 19,300000 active ingredients OLEA EUROPAEA FRUIT OIL & OL EA EUROPAEA LEAF EXTRACT & T OCOPHEROL ACTIVE 3,400000 butter BUTYROSPERMUM PARKII (SHEA) BUTTER LIPEX SHEALI QUID TR 1,000000 pigments PIGMENTS 0,300000 antioxidant TOCOPHEROL & GLYCINE SOJA (SOYBEAN) OIL BIOXAN T 90 0.200000 perfume FRAGRANCE 0.100000

[0508] A lip balm stick is obtained which has adequate stability and hardness: the stick is sufficiently rigid and solid, does not break during application, does not exude over time, does not have surface heterogeneities and is thus compatible with packaging in stick form and with application by friction on the surface to be made up or protected; the stability tests carried out are the same as those described in example 7. The stick is also characterized by ease of application such as good glide, good deposit from the first application and a comfortable texture.

[0509] Example 11: Lipstick formula

[0510] The formula according to Table 7 was prepared as follows: All the raw materials making up the white body, including the wax with a melting point of 80°C obtained according to Example 1 and the pasty D with a melting point of 31.5°C obtained in Example 4, are melted at 90°C with stirring at approximately 250rpm. When the mixture is homogeneous and clear, the previously ground pigments are incorporated into the Cithrol PG32IS. Stirring is increased to 350rpm for 10 min and then increased to 250rpm for 5 min. The pearlescent agents and active ingredients are incorporated. Mixing is continued for 5 min. The antioxidant and perfume are added and stirring is maintained for 5 min. The mixture is poured into molds at 85°C. — INCI name Trade name / Internal name (%) Pigment dispersant POLYGLYCERYL-3 DIISOSTEARATE CITHROL PG32IS-LQ-(MV) 22.5000 00 WHITE BODY Non-volatile oil MEADOWFOAM SE ED OIL (LIMMANT HES ALBA) MEADOWFOAM SEED OIL X PR 17.5000 00 WHITE BODY clay CAPRYLIC / CAPRIC TRIGLYCERIDE & S TEARALKONIUM H ECTORITE & PROP YLENE CARBONATE E BENTONE GEL GTCC V 9.50000 0 WHITE BODY Pasty with addition BIS-BEHENYL / ISO STEARYL / PHYTOS TERYL DIMER DILI NOLEYL DIMER DI LINOLEATE PLANDOOL-G 7.60000 0 WHITE BODY Non-volatile oil SQUALANE NEOSSANCE SQUALANE 7,60000 0 WHITE BODY wax WAX HIGH MELTING POINT 80°C (Hard wax A) Obtained according to the process of example 1 7,30000 0 WHITE BODY Non-volatile oil HELIANTHUS ANNUS (SUNFLOWER) SEED OIL UNSAPO NIFIABLES TECHNOL SD (NON-GMO) 4,30000 0 ACTIVE INGREDIENTS 3,00000 0 WHITE BODY pasty Pasty Melting point 31.5°C (Pasty D) Obtained according to the process of example 4 2,50000 0 CORPS BLANC Cire addi tionnelle CANDELILLA CERA (EUPHORBIA CERIF ERA (CANDELILLA) CANDELILLA WAX CG-7 2,50000 0 , WAX) & BENZYL A LCOHOL pigments PIGMENTS C70-5270 SUNCROMA FD&C YELLOW 6 AL LAKE 5,40000 0 CORPS BLANC Huile no n volatile CAPRYLIC / CAPRIC TRIGLYCERIDE DUB MCT 5545 2,30000 0 CORPS BLANC charge LAUROYL LYSINE AMIHOPE LL 2,00000 0 CORPS BLANC Cire addi tionnelle HELIANTHUS ANN UUS CERA SEED (H ELIANTHUS ANNU US (SUNFLOWER) S EED WAX) SUNFLOWER WAX (USA) 1,80000 0 CORPS BLANC charge CELLULOSE CELLULOBEADS D-10 1,00000 0 nacres MICA & IRON OXID ES PEARLS 3,00000 0 parfum FRAGRANCE 0,10000 0 TOCOPHEROL & GL YCINE SOJA (SOYB EAN) OIL BIOXAN T 90 0,10000 0

[0512] A lipstick stick is obtained which has adequate stability and hardness: the stick is sufficiently rigid and solid, does not break during application, does not exude over time, does not have surface heterogeneities and is thus compatible with packaging in stick form and with application by friction on the surface to be made up; the stability tests carried out are the same as those described in example 7. The stick is also characterized by ease of application such as good glide, good deposit from the first application and a comfortable texture.

[0513] Example 12: Formulation of a skin care product: Nutritional balm

[0514] The formula according to Table 8 was prepared as follows: the fatty phase is weighed: salacos 168EV, salacos 222, Indopol H-100, Meadowfoam seed oil, jojoba oil, Floraester, shea butter, Nomcort HK-G, wax with a melting point of 48°C (soft wax B according to Example 2) according to the invention described above, camellia oil, rice wax, Span 120 and starch, stirred at 250 rpm and heated to 90°C, about 30min. Add the cellulose powder and Lipex omega to the fatty phase once it is homogeneous and increase the stirring to 350rpm for 5min then go to 250rpm for 5min. Add the glycerin and camellia extract then lower the stirring to 150 rpm to avoid bubbling, for 10min. Add the antioxidant and perfume and continue stirring for 5min. Drain at 90°C or pour into the pots at 80°C - 7min at room temperature (RT) and 10min at -19°C.

[0515] [Tables8] Name INCI Trade name / Internal name (%) Nonvolatile oil DIPENTAERYTHRITYL TE TRAHYDROXYSTEARATE / ISOSTEARATE SALACOS 168 EV 21,3000 00 Pigment dispersant s DIISOSTEARYL 0202 PAT0ux1 SALACOS additionnel HYDROGENATED CANOL A OIL & HELIANTHUS AN NUUS (SUNFLOWER) SEE D OIL & CANOLA OIL & C AMELINA SATIVA SEED O IL LIPEX OMEGA 3 / 6 8,000000 filmogen POLYBUTENE non-000 volatile H-08 MEADOWFOAM SEED OIL (LIMMANTHES ALBA) MEADOWFOAM S EED OIL XPR 7,000000 Non-Volatile Oil SIMMONDSIA CHINENSIS (JOJOBA) SEED OIL JOJOBA OIL DE COLOREE 7,000000 Wax JOESTER addition 6,000000 butter BUTYROSPERMUM PARK II LIPEX SHEA 5,000000 charge ALUMINUM STARCH OCT ENYLSUCCINATE DRY FLO PC. 5.000000 Lipophilic Gelfiner GLYCERYL BEHENATE / EI COSADIOATE NOMCORT HK-G 4.000000 WAX HIGH ION MELT POINT 48°C (Soft Wax B) Obtained according to T 0 30, mple 2 humectant GLYCERIN GLYCERINE 4811 3.000000 Non-volatile oil CAMELLIA OLEIFERA SEE D OIL CAMELLIA OIL 2.000000 filler CELLULOSE CELLULOBEADS USF 2.000000 additional wax ORYZA SATIVA (RICE) BR AN WAX REF RICE BRAN W AX PHC3434 - RIC E (ORYZA SATIVA) BRAN WAX 1.600000 Non-volatile oil SORBITAN ISOSTEARATE SPAN 120-LQ-(MV) 0.700000 Anti-oxidant TOCOPHERYL ACETATE DL-ALPHA-TOCOP HERYL ACETATE 0.700000 perfume FRAGRANCE 0.200000

[0516] A care balm is obtained in a cast pot which has adequate stability and hardness: the cast care balm is sufficiently rigid and solid, does not exude over time, does not have surface heterogeneities and is thus compatible with packaging in solid form in a pot and with application by friction on the surface to be nourished; the balm is also characterized by ease of application such as good glide, good deposit from the first application and a comfortable texture.

[0517] Example 13: Formulation of a mascara

[0518] The formula according to Table 9 was prepared as follows: All the raw materials of the fatty phase are melted at 90°C with stirring: palmitostearic acid, wax according to the invention with a melting point of 57°C (Soft Wax F according to Example 6), beeswax, carnauba wax, PVP Hexadecene copolymer. When the mixture is melted and homogeneous, the iron oxides are added and ground for 30 minutes in a deflocculator. The water, polyols, preservatives, triethanolamine and AMPD are heated to 85°C. The gels are dispersed therein. The emulsion is made by pouring the colored fatty phase into the aqueous phase. Homogenize for 20 minutes. The cellulose beads are added. Cool to 50°C, add the antioxidant. Drain at 30°C.

[0519] [Tables9] INCI Name Trade Name / Internal No. (%) water WATER DEMINERALISED WATER EE 47.000000 pigments CI 77499 (IRON OXID ES) C33-7001 SUNPURO BLACK IRON OXIDE 12.000000 emulsifier STEARIC ACID & PAL MITIC ACID KORTACID PH05 - K ORTACID PH05 RSP 0 (MB) 9.500000 WAX MELTING POINT 57°C (Soft wax F) Obtained according to example 6 8.600000 Additional wax CERA ALBA CERABEIL BLANCH E DAB - CERABEIL 5.500000 Additional wax CERA CARNAUBA (C OPERNICIA CERIFER A (CARNAUBA) WAX) CERAUBA Tl - CER AUBA 4.500000 neutralizer TRIETHANOL AMINE TRIETHANOLAMIN ECARE 2.500000 Humectant PENTYLENE GLYCO L HYDROLITE 5 2,500000 Humectant BUTYLENE GLYCOL 1,3 BUTYLENE GLYCOL 2,000000 film former PVP / HEXADECENE C OPOLYMER ANTARON V-216 1,500000 Gelling agent aqueous phase HYDROXYETHYLCE LLULOSE NATROSOL 250 MR PC HYDROXYETHY LCELLULOSE 0,700000 filler CELLULOSE CELLULOBEADS D-100 2,000000 neutralizer AMINOMETHYLPRO PANEDIOL AMPD ULTRA PC, N EUTRALIZING AMI NE 0,500000 preservative POTASSIUM SORBAT E RONACARE POTASS IUM SORBATE 0,450000 preservative CAPRYLYL GLYCOL DERMOSOFT OCTIO L 0.250000 Antioxidant TOCOPHERYL ACET ATE 0.500000

[0520] A mascara is obtained which has adequate stability and rheology: the mascara composition is compatible with packaging in a bottle and with application by a brush on eyelashes or eyebrows; the composition is also characterized by ease of application such as good adhesion, good deposit and a texture which provides volume to the eyelashes similar to that obtained with a mascara of formula in all respects equal to this one with the exception of soft wax F substituted by paraffin wax.

Claims

Claims

1.

2.

3. Process for the preparation of a mixture of linear alkanes of natural origin, preferably of plant origin, comprising the steps of: i. Metathesis of at least one terminal linear olefin, comprising between 5 and 24 carbon atoms, derived from at least one fatty acid or fatty acid ester of natural origin, preferably of plant origin, in the presence of a non-isomerizing olefin metathesis catalyst, whereby a first mixture of internal olefins (I) is obtained; ii. Isomerizing metathesis of the mixture of internal olefins (I) obtained in step i) in the presence of a catalyst or a mixture of catalysts, whereby a second mixture of internal olefins (II) is obtained, and iii. Hydrogenation of the mixture of internal olefins (II) in the presence of a catalyst, whereby a mixture (III) of linear alkanes of natural origin is obtained. Process according to claim 1, in which the non-isomerizing olefin metathesis catalyst in step i) is chosen from transition metal complexes, in particular transition metal alkylidenes, in particular ruthenium. The process of claim 2, wherein the non-isomerizing olefin metathesis catalyst is selected from Ru-1a, Ru-1b or a mixture thereof. [Chem.l] Ru-la

4. [Chem.2] i PCy3 Process according to any one of the preceding claims, in which the catalyst or mixture of catalysts used in step ii) is a transition metal complex, in particular ruthenium.

5. The process of claim 4, wherein the olefin isomerizing metathesis catalyst is a mixture of Ru-2 and Ru-3 [Chem. 3] [Chem.4] [ Here O c / | M .0™C H3C--< \:™. / H ch3

6.

7. Ru-3 Process according to any one of the preceding claims, in which the terminal olefins used in step i) are prepared from fatty acid esters derived from jojoba oil. Process according to any one of the preceding claims, in which said at least one linear terminal olefin used in step i) is a mixture of at least two linear olefins distinct terminals each comprising between 5 and 24 carbon atoms, in particular between 16 and 24 carbon atoms, preferably between 16 and 20 carbon atoms.

8. A method according to claim 7, wherein said at least two terminal linear olefins differ from each other by a number of carbon atoms of at least two.

9. Process according to any one of the preceding claims, wherein said at least one terminal linear olefin used in step i) is a mixture of three terminal linear olefins, preferably C6 / C7 / C8, C8 / C9 / C10, C10 / C12 / C14, or C16 / C18 / C20.

10. A method according to claim 9, wherein the mixture comprises: - From 1 to 10% by weight of C16 terminal olefins; - From 45 to 49.5% of C18 terminal olefins; and - From 45 to 49.5% of C20 terminal olefins; The percentages being expressed by weight relative to the total weight of the mixture of terminal olefins.

11. Mixture of linear alkanes of natural origin, in particular of plant origin, said mixture being obtained according to the process as defined in claims 1 to 10.

12. A mixture of linear alkanes according to claim 11, wherein the mixture comprises at least two distinct linear alkanes, said at least two distinct linear alkanes each having between 10 and 70 carbon atoms, preferably between 24 and 60 carbon atoms.

13. Mixture of linear alkanes of natural origin, in particular of plant origin, in particular in the form of a solid fatty substance, in which: - each linear alkane constituting the mixture contains between 10 and 70 carbon atoms, and - the distribution of the numbers of each linear alkane, arranged by increasing number of carbon atoms, is: . increasing between the linear alkane having the smallest number of carbon atoms up to the mode of distribution; and . decreasing between the mode of distribution and the linear alkane having the largest number of carbon atoms, . the numbers being calculated as a percentage by weight relative to the total weight of the mixture of linear alkanes of natural origin.

14. A mixture of linear alkanes according to claim 13, wherein each linear alkane in the distribution differs by one carbon atom from the next linear alkane in the distribution.

15. A mixture of linear alkanes according to claims 13 or 14, wherein each linear alkane constituting the mixture has between 24 and 60 carbon atoms.

16. A mixture of linear alkanes according to claims 13 to 15, wherein the mode of distribution is between 40 and 45 carbon atoms.

17. A mixture of linear alkanes according to any one of claims 13 to 16, wherein the median of the distribution is between 40 and 45 carbon atoms.

18. A mixture of linear alkanes according to any one of claims 13 to 17, wherein the mixture has a melting point of between 75 and 85°C.

19. A mixture of linear alkanes according to any one of claims 13 or 14, wherein each linear alkane constituting the mixture comprises between: - 17 and 44 carbon atoms; - 22 and 54 carbon atoms; or - 12 and 47 carbon atoms; or - 11 and 50 carbon atoms; or - 11 and 54 carbon atoms.

20. A composition comprising a mixture of linear alkanes according to any one of claims 11 to 19.

21. Composition according to claim 20, comprising less than 3% by weight, in particular less than 1% by weight, preferably free of solid fatty substances of mineral and / or synthetic origin, the percentages by weight being expressed relative to the total weight of the composition.

22. Composition according to claim 20 or 21, characterized in that it is a cosmetic or pharmaceutical composition.

23. Composition according to claim 22, in which the cosmetic composition is a perfuming, care or makeup product for the skin, mucous membranes or superficial body appendages.

24.

25.

26.

27.

28. Composition according to one of claims 20 to 23, characterized in that it is an anhydrous composition. Composition according to one of claims 20 to 24, characterized in that it is a solid composition. Composition according to one of claims 20 to 25, characterized in that it is a solid composition in stick form. Composition according to one of claims 22 to 26, characterized in that it is a mascara composition. Use of a mixture of linear alkanes according to any one of claims 11 to 19, in the field of cosmetics, pharmaceuticals, coatings, inks, varnishes, paper, adhesives, candles, plastics, rubbers and / or food products.

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