PROCESS FOR ENRICHING PONGAMOL WITH KARANJA OIL

专利摘要:
The invention relates to a cosmetic ingredient, characterized in that it consists of a solution of at least one extract of karanja oil comprising pongamol (CAS 484-33-3) and karanjine (CAS 521 -88-0) in at least one solvent selected from the group of the following diesters of formula (I), or mixtures thereof: wherein: n is from 0 to 19; - R and R 'identical or different are selected from the group of alkyls derived from a linear or branched alcohol of empirical formula CxH2x + 20 before esterification, x being between 1 and 30, preferably between 1 and 20, preferentially between 1 and 10. R "is either a hydrogen atom or a C 1 -C 3 alkyl group [0002] The invention also relates to a selective precipitation process, a cosmetic formulation and its uses.
公开号:FR3039063A1
申请号:FR1556973
申请日:2015-07-22
公开日:2017-01-27
发明作者:Thierry Bernoud；Antoine Piccirilli；Julien Magne
申请人:Biosynthis Sarl；BIOSYNTHIS；
IPC主号:

专利说明:

PROCESS FOR ENRICHMENT OF PONGAMOL OIL
KARANJA
The present invention relates to the field of oleochemistry and more particularly oils used in cosmetics.
More particularly, the invention relates to a selective extraction process unsaponifiables of a lipid material of plant origin, this renewable lipid material being karanja oil.
At the end of said process, an extract is obtained, said extract (consisting of a solution) that can be incorporated into cosmetic or pharmaceutical compositions.
[0004] Karanja is a plant of the family of legumes, native to Asia. It is particularly found in India, Japan, and southern China. It is a robust tree or liana measuring 20 to 30 m.
The term "karanja" within the meaning of the present application refers in particular to the following species: Pongamia glabra, Pongamia pinnata, Milletia pinnata, Derris indica, Gadelupa pinnata, Pongamia grandifolia, Robinia mitis, Tephrosia purpurea, Tephrosia hamiltoni, Tephrosia falciformis, Tephrosia vogellii, Tephrosia lanceolata, etc.
[0006] Different parts of the plant are used: the roots are used as a dental product or as a local antiseptic, the leaves are digestive and laxative, and are also used as antiseptic. The barks are used as a dewormer and, finally, the seeds are used as a source of karanja oil.
[0007] Karanja seeds comprise about 27 to 39% of karanja oil.
[0008] Karanja oil is obtained from seeds, by pressure or by solvent extraction. The meal, which is less rich in oil than the seeds, can also be used as a raw material. The oils obtained generally have the same physicochemical characteristics, in the form of a cloudy liquid, of brown to orange color, and of strong, unpleasant odor.
[0009] The karanja oil mainly comprises triglycerides as well as oleic and linoleic acids, and in smaller proportions: palmitic acid, stearic acid, linolenic acid and arachidic acid. as well as behenic acid.
[00010] Karanja oil, once extracted from seeds, is widely used. In the Ayurvedic pharmacopoeia, it is particularly used for the care of the skin, hair, especially with regard to its antiseptic and antiparasitic properties, it is also used in the treatment of eczema, psoriasis and in the treatment of leather scalp. Karanja oil is sometimes also used as an insecticide.
[00011] Karanja oil, in addition to the traditional uses mentioned above, is also used more recently as a sunscreen, alone or in combination with other sunscreens, in cosmetic compositions. This is due in particular to the presence of certain unsaponifiable compounds. As an indication, karanja oil is composed of about 2 to 5% of unsaponifiables, the best known are two diketones: pongamol (CAS 482-33-3) and karanjine (CAS 521-88-0). ).
In very general terms, the average mass percentages of pongamol and karanjine in karanja oils are between 0.3 and 0.9% for pongamol and between 2 and 4% for karanjine.
These percentages by weight are given for information only, because they can vary widely depending on the species, the season, the place of sampling, etc.
The sun protection properties of karanja oil are essentially due to the presence of pongamol, the latter is a natural filter having a UV absorption spectrum similar to that of methoxydibenzoylmethane (CAS 70356-09-1), better known under the brand name PARSOL 1789®.
However, the incorporation of karanja oil in solar compositions is limited by the organoleptic characteristics of said oil.
These negative organoleptic characteristics are essentially due to the presence of karanjine.
The elimination of all or part of the karanjine of karanja oil has the direct effect of increasing the amount of this oil incorporated in sunscreen cosmetic compositions. Moreover, the maintenance of a sufficient mass percentage of pongamol is important in order to preserve good solar properties.
However, the selective elimination of karanjine is difficult, due to the chemical relationship between karanjine and pongamol.
In the application WO 2014/016349 in the name of BIOSYNTHIS, there is disclosed a solar composition comprising karanja oil and other compounds, and in particular a polyester. In this application, there is no question of a selective extraction process.
[00020] In a commercial publication (GIVAUDAN: Leading sensory innovation: Pongamia extract and karanja oil, Issue 004 April 08), the solar effects of compositions comprising pure pongamol are touted. On page 11, pure pongamol is characterized (90% minimum).
In FR 2762008 in the name of PIERRE FABRE, a deodorization process of karanja oil is disclosed. Other cosmetic applications of karanja oil are also described, including anti-wrinkle and moisturizing properties.
In the application GB 2237805 in the name of UNILEVER PLC, a diketone extraction process is disclosed, this process comprises two steps: extraction with an organic acid and separation of the troublesome diketone molecules. More specifically, it is about pongamol extraction. It is specified that the karanja oil, after removal of pongamol, is used for the manufacture of soaps, the final oil is therefore relatively free of pongamol. With regard to pongamol, crystals are formed during the process, the latter having a melting point between 126 ° C and 127.5 ° C, the resulting pongamol therefore seems relatively pure.
In the application WO 2014195639 in the name of VALAGRO, a method for extracting unsaponifiables from a renewable lipid raw material is disclosed. Example 1 is particularly related to the selective extraction of pongamol and karanjine. The process consists mainly of two stages, a first step of solid / liquid extraction carried out using a percolator with circulation and recirculation of an ethanol / hexane mixture through crushed and previously dried seeds, as well as a concentration step by evaporation of the solvent.
In summary, no document of the prior art discloses a selective extraction process of karanjine economic, environmentally friendly, inexpensive and easy to implement.
This is probably due to the difficulties that the skilled person encounters to selectively extract two molecules close to a structural point of view.
[00026] There is therefore an interest in having an improved selective extraction process.
[00027] Surprisingly, it has been demonstrated that it is possible to selectively extract karanjine by means of a process having all the following positive characteristics: economical, environmentally friendly, inexpensive and easy to use. to selectively solubilize pongamol by means of diester type solvents which are compatible with the requirements of the cosmetic industry.
Among these diesters, the following compounds of formula (I), or their mixtures, are especially considered:
Formula (I) wherein: n is from 0 to 19; R and R ', which are identical or different, are alkyls originating from an esterification with a linear or branched alcohol of empirical formula CxH2x + 20, x being between 1 and 30, preferentially between 1 and 20, preferably between 1 and 10. R " is either a hydrogen atom or a C 1 -C 3 alkyl group.
These diesters have flash points above 70 ° C and therefore do not present the dangers of VOCs whose flash points are below 70 ° C.
In the context of the present invention, certain di esters are particularly preferred, such as for example sebacates (n = 7), adipates (n = 3), succinates (n = 1), dodecanedioates (n = 1), 9), azelates (n = 6), glutarates (n = 2), malonates (n = 0), etc.
The invention relates to a cosmetic ingredient, characterized in that it consists of a solution of at least one karanja oil extract comprising pongamol (CAS 484-33-3) and karanjine (CAS 521 -88-0) in at least one solvent chosen from the group of di esters of formula (I) below, or mixtures thereof:
Formula (I) wherein: - n is from 0 to 19; - R and R 'identical or different are selected from the group of alkyls derived from a linear or branched alcohol of empirical formula CxH2x + 20 before esterification, x being between 1 and 30, preferably between 1 and 20, preferentially between 1 and 10. R "is either a hydrogen atom or a C 1 -C 3 alkyl group.
The invention also relates to a process for the selective precipitation of pongamol (CAS 484-33-3) in a karanja oil comprising pongamol (CAS 484-33-3) and karanjine (CAS 521-88-0). ), characterized in that it comprises: 1) at least one step of adding to said at least one karanja oil at least one solvent selected from the group of the following diesters of formula (I), or mixtures thereof:
Formula (I) wherein: - n is from 0 to 19; - R and R 'identical or different are alkyls from an esterification with a linear or branched alcohol of empirical formula CxH2x + 20, x being between 1 and 30, preferably between 1 and 20, preferably between 1 and 10. R is either a hydrogen atom or a C 1 -C 3 alkyl group, said addition having the effect of forming a light phase (supernatant) in the form of a solution and a heavy phase in the form of a precipitate, and 2) at least one separation step of the two phases obtained.
[00033] The invention also relates to a cosmetic formulation, characterized in that it comprises: a cosmetic ingredient according to the invention; a cosmetically acceptable vehicle.
The invention also relates to the use of a cosmetic formulation according to the invention as described above, as a solar cosmetic formulation.
The invention also relates to the use of a cosmetic formulation according to the invention as described above, as anti-aging cosmetic formulation.
In addition to the ecological and economic interests, the process according to the invention makes it possible to obtain, with a process comprising few steps, a solution enriched in pongamol ready to be formulated directly without requiring a melting and dissolving step. hot pongamol before incorporation into a cosmetic formulation as should be done when using pure pongamol.
From the economic point of view, the respect of the environment and the cost, the process that can be carried out at ambient temperature makes it possible to save resources, insofar as no solvent is removed during the process. In addition, no toxic solvent is used, in particular, no flammable solvent classified as light VOC (flash points <70 ° C) is used.
The method also allows the use of biosourced solvents such as sebacates, succinates, and azelates having a better environmental impact than their counterparts of fossil origin. In addition, the extraction of the unsaponifiable fraction preserves the triglycerides, which can in turn be recovered, since the process does not include any saponification or hydrolysis step.
From the point of view of the ease of implementation, the method comprises a limited number of relatively simple steps to implement. In particular, it has no step of conditioning the seed (drying, grinding, flattening, etc.) required for example by the method described in WO 2014195639 in the name of VALAGRO.
[00040] A number of definitions are given below.
The term "karanja oil" is any oil derived from a plant of the karanjas family. These may include the following plant species: Pongamia glabra, Pongamia pinnata, Milletia pinnata, Demis indica, Gadelupa pinnata, Pongamia grandifolia, Robinia mitis, Tephrosia purpurea, Tephrosia hamiltoni, Tephrosia falciformis, Tephrosia vogellii, Tephrosia lanceolata, etc. The karanja oil can be "raw", that is, obtained directly from the seeds by cold pressing or solvent extraction with removal of the solvent.
[00042] Karanja oil may also undergo treatments to purify it by eliminating particular impurities, deodorizing or bleaching.
It may for example be one or more molecular distillation (s) and / or degumming and / or one or more deodorization (s).
The "light phase (supernatant)" is the light phase resulting from the selective precipitation step. This is a solution. It is separated from the heavy phase (precipitate) by methods well known to those skilled in the art, which may for example be centrifugation or filtration. The light phase (supernatant) is of particular interest, insofar as once separated from the clay phase (precipitate), the light phase (supernatant) which is a solution constitutes the cosmetic ingredient according to the invention.
The "heavy phase (precipitate)" is the heavy phase resulting from the selective precipitation step. It is separated from the light phase (supernatant) by methods well known to those skilled in the art, which may for example be centrifugation or filtration.
[00046] "Precipitation" is a precipitation that precipitates in particular a chemical species from a mixture. In the selective precipitation process according to the invention, karanjine is preferentially precipitated with respect to pongamol. For example, when in a precipitation step the precipitate is composed of 61.5% karanjin and only 4.3% pongamol, it is a selective karanjin precipitation.
The term "mass percentage" (expressed in%) is the ratio between the mass of a constituent of a mixture and the total mass of the mixture. For example, if a component of a mixture has a mass of 1 kg and the mixture has a mass of 100 kg, the weight percentage of component i is 1%. For example, when a cosmetic ingredient according to the invention is characterized in that the weight percentage of pongamol in the solution (of which the cosmetic ingredient is entirely constituted) is 3%, this means that in 100 g of cosmetic ingredient / solution, there is 3 g of pongamol.
The term "extraction yield" is the ratio between the mass of a component before a step (for example, a selective precipitation step) and the mass of the same component after said step. It can in particular be expressed as a percentage, and is between 0% and 100%. For example, the extraction yield of pongamol during precipitation is calculated as follows: mass of pongamol in karanja oil before precipitation / mass of pongamol in the solution obtained at the end of the precipitation. When "extraction efficiency in one phase" is used, it is the ratio of the mass of a component in the phase to the mass of the same component before the step that led to the formation of the phase.
[00049] The multiplication of the ratio of mp0ngamoi / mkaranjine masses is called multiplication of the mpongamoi / rnkaranjine ratio during one or more steps of the process, expressed as follows:
For example, it may be the multiplication of the mass ratio mpongamol / mkaranjine! O rs steps 1) and 2), the comparison is then made between the mass ratio mpongamoi / mkaranjine before I step 1) and the mPongamoi / mkaranjine ratio after step 2); if before step 1), the ratio mp0ngamoi / mkaranjine is 0.71, and after step 2), the mp0ngamoi / mkaranjine ratio (in the solution resulting from the recovery of the light phase or supernatant) is 1 , 75, then the multiplication of the ratio nripongamoi / mkaranjine is calculated as follows: 1.75 / 0.71 = 2.46. The nipongamoi / mkaraniine ratio was multiplied by a factor of 2.46 in steps 1) and 2).
The invention relates to a cosmetic ingredient, characterized in that it consists of a solution of at least one karanja oil extract comprising pongamol (CAS 484-33-3) and karanjine (CAS 521 -88-0) in at least one solvent selected from the group of the following diesters of formula (I), or mixtures thereof:
Formula (I) wherein: n is from 0 to 19; R and R ', which are identical or different, are alkyls originating from an esterification with a linear or branched alcohol of empirical formula CxH2x + 20, x being between 1 and 30, preferentially between 1 and 20, preferably between 1 and 10. R " is either a hydrogen atom or a C 1 -C 3 alkyl group.
In one embodiment, the cosmetic ingredient according to the invention is characterized in that R "is a hydrogen atom.
In one embodiment, the cosmetic ingredient according to the invention is characterized in that R "is a methyl.
In one embodiment, the cosmetic ingredient according to the invention is characterized in that x is between 1 and 20.
In one embodiment, the cosmetic ingredient according to the invention is characterized in that x is between 1 and 10.
In one embodiment, the cosmetic ingredient according to the invention is characterized in that n is between 1 and 10.
In one embodiment, the cosmetic ingredient according to the invention is characterized in that R is identical to R '.
In one embodiment, the cosmetic ingredient according to the invention is characterized in that R is different from R '.
In one embodiment, the cosmetic ingredient according to the invention is characterized in that the said at least one solvent is chosen from the group consisting of sebacates (n = 7), adipates (n = 3), succinates (n = 1), dodecanedioates (n = 9), azelates (n = 6), glutarates (n = 2), malonates (n = 0), and mixtures thereof.
In one embodiment, the cosmetic ingredient according to the invention is characterized in that said at least one solvent is selected from the group consisting of sebacates (n = 7).
Sebacates are widely used solvents. They are derivatives of sebacic acid, or decanedioic acid (CAS 111-20-6) which is a 10-carbon dicarboxylic acid of the following formula:
The sebacic acid may be doubly esterified by the use of two identical or different alcohols.
In one embodiment, the cosmetic ingredient according to the invention is characterized in that the said at least one solvent is a sebacic acid doubly esterified with two identical or different alcohols, each of the two alcohols being a linear or branched alcohol. or a mixture of isomers in any proportions where appropriate, or only one of the isomers where appropriate, the alcohol being C 1 -C 3, preferably C 1 -C 2, preferably C 1 -C 10.
In one embodiment, the cosmetic ingredient according to the invention is characterized in that the said at least one solvent is a sebacic acid doubly esterified with two identical or different alcohols, each of the two alcohols being chosen from the group consisting of by methanol, ethanol, propanols of empirical formula C3H80, butanols of formula C4H10O, pentanols of empirical formula C5H12O, hexanols of empirical formula C6Hi40, heptanols of empirical formula C7Hi50, octanols of empirical formula C8Hi80, nonanols of formula CgH2OO, decanols of formula C10H22O, undecanol of formula CnH240, dodecanol of formula C12H260, tridecanol of formula C13H280, tetradecanol of formula C14H30O, pentadecanol of formula C15H3O, hexadecanol of the empirical formula C16H340, the heptadecanol of the empirical formula C17H360, the octadecanol of the empirical formula C18H380, the nonadecanol of Crude formula Ci9H4oO and eicosanols of formula C20H42O.
In one embodiment, the cosmetic ingredient according to the invention is characterized in that the said at least one solvent is a sebacic acid doubly esterified with two identical or different alcohols, each of the two alcohols being chosen from the group consisting of methanol (CAS 67-56-1), ethanol (CAS 64-17-5), propan-1-ol (or n-propanol) (CAS 71-23-8), propan-2- ol (or isopropanol) (CAS 67-63-0), butan-1-ol (or n-butanol) (CAS 71-36-3), (R) -butan-2-ol (CAS 14898-79 -4), (S) -butan-2-ol (CAS 4221-99-2), 2-methylpropan-1-ol (CAS 78-83-1), 2-methylpropan-2-ol (CAS 75-65-0), 2-methylpropan-2-ol (CAS 75-65-0), pentan-1-ol (CAS 71-41-0), 3-methylbutan-1-ol (CAS 123 -51-3), 2-methylbutan-1-ol (CAS 137-32-6), 2,2-dimethylpropan-1-ol (CAS 75-84-3), pentan-3-ol (CAS 584-02-1), pentan-2-ol (CAS 6032-29-7), 3-methylbutan-2-ol (CAS 598-75-4), 2-methylbutan-2-ol (CAS 75 85-4), hexan-1-ol (CAS 111-27-3), heptan-1-ol (CAS 111-70-6), dodecan-1-ol (CAS 112-53-8), octan-1-ol (CAS 111-87-5), ethyl hexan-1-ol (CAS 104-76-7), octadecan-1-ol (CAS 112-92-5), decan-1-ol (CAS 112-30-1) and dodecan l-ol (CAS 112-53-8).
In one embodiment, the cosmetic ingredient according to the invention is characterized in that the said at least one solvent is chosen from the group consisting of dioctyl sebacate (CAS 122-62-3) and diethyl sebacate. (CAS 110-40-7), dibutyl sebacate (CAS 109-43-3), diisopropyl sebacate (CAS 7491-02-3), and mixtures thereof.
In one embodiment, the cosmetic ingredient according to the invention is characterized in that the said at least one solvent is chosen from the group consisting of diethyl sebacate (CAS 110-40-7) and dibutyl sebacate. (CAS 109-43-3), diisopropyl sebacate (CAS 7491-02-3) and mixtures thereof.
In one embodiment, the cosmetic ingredient according to the invention is characterized in that the said at least one solvent is diethyl sebacate (CAS 110-40-7).
[00069] Sebacic acid diesters are used in cosmetology. In WO 9850005 in the name of MEDLOGIC GLOBAL CORPORATION, diethyl sebacate is cited as a solvent, and diisopropyl sebacate and dibutyl sebacate are cited as emollients.
In US Patent 5152983 in the name of CHESEBROUGH-POND'S USA CO, dibutyl sebacate is cited as emollient, and it is expected the addition of pongamol in the composition. In the composition of Example 1, a solar composition comprising pongamol is tested.
[00071] Adipates are widely used solvents. They are derivatives of adipic acid (CAS 124-04-9) which is an aliphatic dicarboxylic acid of the following formula:
The adipic acid may be doubly esterified by the use of two identical or different alcohols.
In one embodiment, the cosmetic ingredient according to the invention is characterized in that the said at least one solvent is a sebacic acid doubly esterified with two identical or different alcohols, each of the two alcohols being a linear or branched alcohol. or a mixture of isomers in any proportions where appropriate, or only one of the isomers if appropriate, the alcohol being C 1 -C 30, preferably C 1 -C 20, preferably C 1 -C 10.
In one embodiment, the cosmetic ingredient according to the invention is characterized in that said at least one solvent is an adipic acid doubly esterified with two identical or different alcohols, each of the two alcohols being chosen from the group consisting of by methanol, ethanol, propanols of empirical formula C3H80, butanols of formula C4H10O, pentanols of empirical formula C5Hi20, hexanols of empirical formula C6H40, heptanols of empirical formula C7H160, octanols of empirical formula C8H180, nonanols of formula C9H20O, decanols of formula C10H22O, undecanol of formula CnH240, dodecanol of formula C12H260, tridecanol of formula C13H280, tetradecanol of formula C14H30O, pentadecanol of formula C15H320, hexadecanol of the empirical formula C16H340, the heptadecanol of the empirical formula C17H360, the octadecanol of the empirical formula C18H380, the nonadecanol of the formula Crude formula Ci9H40O and eicosanols of the empirical formula C20H42O.
In one embodiment, the cosmetic ingredient according to the invention is characterized in that the said at least one solvent is an adipic acid doubly esterified with two identical or different alcohols, each of the two alcohols being chosen from the group consisting of methanol (CAS 67-56-1), ethanol (CAS 64-17-5), propan-1-ol (or n-propanol) (CAS 71-23-8), propan-2- ol (or isopropanol) (CAS 67-63-0), butan-1-ol (or n-butanol) (CAS 71-36-3), (R) -butan-2-ol (CAS 14898-79 -4), (S) -butan-2-ol (CAS 4221-99-2), 2-methylpropan-1-ol (CAS 78-83-1), 2-methylpropan-2-ol (CAS 75-65-0), 2-methylpropan-2-ol (CAS 75-65-0), pentan-1-ol (CAS 71-41-0), 3-methylbutan-1-ol (CAS 123 -51-3), 2-methylbutan-1-ol (CAS 137-32-6), 2,2-dimethylpropan-1-ol (CAS 75-84-3), pentan-3-ol (CAS 584-02-1), pentan-2-ol (CAS 6032-29-7), 3-methylbutan-2-ol (CAS 598-75-4), 2-methylbutan-2-ol (CAS 75 85-4), hexan-1-ol (CAS 111-27-3), hr eptan-1-ol (CAS 111-70-6), dodecan-1-ol (CAS 112-53-8), octan-1-ol (CAS 111-87-5), 2-ethylhexan 1-ol (CAS 104-76-7), octadecan-1-ol (CAS 112-92-5), decan-1-ol (CAS 112-30-1) and dodecan-1- ol (CAS 112-53-8).
In one embodiment, the cosmetic ingredient according to the invention is characterized in that the said at least one solvent is selected from the group consisting of dihexyl adipate (CAS 2091-24-9), diisostearyl adipate (CAS 62479-36-1), dicapryl adipate (CAS 108-63-4), di-C12-15 alkyl adipate, ditridecyl adipate (CAS 16958- 92-2), dicetyl adipate (CAS 26720-21-8), diisopropyl adipate (CAS 6938-94-9), diisobutyl adipate (CAS 141-04-8), diisopropyl adipate (CAS 103-23-1), diisooctyl adipate (CAS 1330-86-5), diisononyl adipate (CAS 33703-08-1), adipate diisodecyl (CAS 27178-16-1), diethyl adipate (CAS 141-28-6), dimethyl adipate (CAS 627-93-0), dihexyldecyl adipate (CAS 57533- 90-1), diheptylundecyl adipate (CAS 155613-91-5), dipropyl adipate (CAS 106-19-4), dioctyldodecyl adipate (CAS 85117-94-8), dibut adipate yle (CAS 105-99-7), diisocetyl adipate (CAS 57533-90-1), dioctyl adipate (CAS 123-79-5) and mixtures thereof.
In one embodiment, the cosmetic ingredient according to the invention is characterized in that the said at least one solvent is chosen from the group consisting of diisopropyl adipate (CAS 6938-94-9), dibutyl adipate (CAS 105-99-7), dioctyl adipate (CAS 123-79-5) and mixtures thereof.
Succinates are widely used solvents. They are derivatives of succinic acid (CAS 110-15-6) of following formula:
The succinic acid may be doubly esterified by the use of two identical or different alcohols.
In one embodiment, the cosmetic ingredient according to the invention is characterized in that the said at least one solvent is a sebacic acid doubly esterified with two identical or different alcohols, each of the two alcohols being a linear or branched alcohol. or a mixture of isomers in any proportions where appropriate, or only one of the isomers where appropriate, the alcohol being C 1 -C 30, preferably C 1 -C 10, preferably C 1 -C 10.
In one embodiment, the cosmetic ingredient according to the invention is characterized in that the said at least one solvent is a succinic acid doubly esterified with two identical or different alcohols, each of the two alcohols being chosen from the group consisting of by methanol, ethanol, propanols of formula C3H80, butanols of formula C4H10O, pentanols of formula C5Hi20, hexanols of formula C6Hi40, heptanols of formula C7Hi60, octanols of formula C8H180, nonanols of the empirical formula C9H20O, the decanols of the empirical formula C10H22O, the undecanol of the empirical formula CuH240, the dodecanol of the empirical formula Ci2H250, the tridecanol of the empirical formula C13H280, the tetradecanol of the empirical formula Cx4H30O, the pentadecanol of the empirical formula Ci5H320, the hexadecanol of the empirical formula C16H340, the heptadecanol of the empirical formula C17H360, the octadecanol of the empirical formula C18H380, the nonadecanol of crude formula C19H40O and eicosanols of formula C20H42O.
In one embodiment, the cosmetic ingredient according to the invention is characterized in that the said at least one solvent is a succinic acid doubly esterified with two identical or different alcohols, each of the two alcohols being chosen from the group consisting of methanol (CAS 67-56-1), ethanol (CAS 64-17-5), propan-1-ol (or n-propanol) (CAS 71-23-8), propan-2- ol (or isopropanol) (CAS 67-63-0), butan-1-ol (or n-butanol) (CAS 71-36-3), (R) -butan-2-ol (CAS 14898-79 -4), (S) -butan-2-ol (CAS 4221-99-2), 2-methylpropan-1-ol (CAS 78-83-1), 2-methylpropan-2-ol (CAS 75-65-0), 2-methylpropan-2-ol (CAS 75-65-0), pentan-1-ol (CAS 71-41-0), 3-methylbutan-1-ol ( CAS 123-51-3), 2-methylbutan-1-ol (CAS 137-32-6), 2,2-dimethylpropan-1-ol (CAS 75-84-3), pentan-3-ol (CAS 584-02-1), pentan-2-ol (CAS 6032-29-7), 3-methylbutan-2-ol (CAS 598-75-4), 2-methylbutan-2-ol ( CAS 75-85-4), hexan-1-ol (CAS 111-27-3), heptan-1-ol (CAS 111-70-6), dodecan-1-ol (CAS 112-53-8), octan-1-ol (CAS 111-87-5), 2- ethylhexan-1-ol (CAS 104-76-7), octadecan-1-ol (CAS 112-92-5), decan-1-ol (CAS 112-30-1) and dodecan-1 -ol (CAS 112-53-8).
In one embodiment, the cosmetic ingredient according to the invention is characterized in that the said at least one solvent is chosen from the group consisting of didecyl succinate (CAS 10595-82-1) and dimethyl succinate. (CAS 106-65-0), diethyl succinate (CAS 123-25-1), dicapryl succinate (CAS 14491-66-8), dicetearyl succinate (CAS 93280-98-9), succinate diisobutyl (CAS 925-06-4), diethylhexyl succinate (CAS 2915-57-3) and mixtures thereof.
In one embodiment, the cosmetic ingredient according to the invention is characterized in that the said at least one solvent is diethylhexyl succinate (CAS 2915-57-3).
The 2-methyl succinates are derivatives of 2-methyl sucenic acid (CAS 498-21-5) of the following formula:
The 2-methyl succinic acid may be double esterified by the use of two identical or different alcohols.
In one embodiment, the cosmetic ingredient according to the invention is characterized in that the said at least one solvent is a 2-methyl succinic acid doubly esterified with two identical or different alcohols, each of the two alcohols being an alcohol. linear or branched, or a mixture of isomers in any proportions where appropriate, or only one of the isomers where appropriate, the alcohol being C 1 -C 30, preferably C 1 -C 20, preferentially C 1 -C 10 .
In one embodiment, the cosmetic ingredient according to the invention is characterized in that said at least one solvent is a 2-methyl succinic acid doubly esterified with two identical or different alcohols, each of the two alcohols being chosen from the group consisting of methanol, ethanol, propanols of formula C3H80, butanols of formula C4H10O, pentanols of formula C5Hi20, hexanols of formula C6Hi40, heptanols of formula C7Hi60, octanols of formula Crude C8Hi80, Nonanols of Formula C9H20O, Decanols of Formula C10H22O, Undecanol of Formula CuH240, Dodecanol of Formula C12H260, Tridecanol of Formula C13H280, Tetradecanol of Formula C14H30O, Pentadecanol of Formula C15H32O, hexadecanol of the empirical formula C16H340, the heptadecanol of the empirical formula C17H360, the octadecanol of the empirical formula C18H380, the nonadec canols of the empirical formula Ci9H40O and the eicosanols of the empirical formula C20H42O.
In one embodiment, the cosmetic ingredient according to the invention is characterized in that the said at least one solvent is a 2-methyl succinic acid doubly esterified with two identical or different alcohols, each of the two alcohols being chosen from the group consisting of methanol (CAS 67-56-1), ethanol (CAS 64-17-5), propan-1-ol (or n-propanol) (CAS 71-23-8), propane 2-ol (or isopropanol) (CAS 67-63-0), butan-1-ol (or n-butanol) (CAS 71-36-3), (R) -butan-2-ol (CAS 14898-79-4), (S) -butan-2-ol (CAS 4221-99-2), 2-methylpropan-1-ol (CAS 78-83-1), 2-methylpropan-2- o! (CAS 75-65-0), 2-methylpropan-2-ol (CAS 75-65-0), pentan-1-ol (CAS 71-41-0), 3-methylbutan-1-ol ( CAS 123-51-3), 2-methylbutan-1-ol (CAS 137-32-6), 2,2-dimethylpropan-1-ol (CAS 75-84-3), pentan-3-ol (CAS 584-02-1), pentan-2-ol (CAS 6032-29-7), 3-methylbutan-2-ol (CAS 598-75-4), 2-methylbutan-2-ol ( CAS 75-85-4), hexan-1-ol (CAS 111-27-3), heptan-1-ol (CAS 111-70-6), dodecan-1-ol (CAS 112-53-8), octan-1-ol (CAS 111-87-5), 2-ethylhexan-1-ol (CAS 104-76-7), octadecan-1-ol ( CAS 112-92-5), decan-1-ol (CAS 112-30-1) and dodecan-1-ol (CAS 112-53-8).
In one embodiment, the cosmetic ingredient according to the invention is characterized in that the said at least one solvent is chosen from the group consisting of diethyl 2-methyl succinate (CAS 4676-51-1), 1-ethyl and 4-methyl 2-methyl succinate (CAS 204125-41-7), 1-methyl and 4-methyl 2-methyl succinate (CAS 606491-29-6), 2-methyl succinate dipropyl (CAS 56108-32-8), diisopropyl 2-methyl succinate (CAS 75906-62-6), 1-butyl 2-methyl succinate and 4-methyl (CAS 878209-18-8), di (2-methylpropyl) 2-methyl succinate (CAS 18447-89-7), 1-pentyl and 4-methyl 2-methyl succinate (CAS 204125-40-6), 2-methyl succinate, 1-methyl and 4-hexyl (CAS 214280-22-5), di (1-methylpropyl) 2-methyl succinate (CAS 57983-31-0), di (1,1-dimethylethyl) 2-methylsuccinate ) (CAS 108763-17-3), dipentyl 2-methyl succinate (CAS 56108-33-9), dihexyl 2-methyl succinate (CAS 32774-96-2), diheptyl 2-methyl succinate (CAS 51191-78-7), 1-methyl and 4-dodecyl 2-methyl succinate (CAS 214280-27-0), dioctyl 2-methyl succinate (CAS 131787- 12-7), 1-methyl and 4-octadecyl 2-methyl succinate, didecyl 2-methyl succinate, didodecyl 2-methyl succinate or lauryl, decanyl 2-methylsuccinate, 2-methylsuccinate, 2-ethylhexanyl, their isomers and mixtures of isomers, and mixtures thereof.
[00091] Dodecanedioates are widely used solvents. They are derivatives of dodecanedioic acid (CAS 693-23-2) which is an aliphatic dicarboxylic acid of the following formula;
The dodecandioic acid may be doubly esterified by the use of two identical or different alcohols.
In one embodiment, the cosmetic ingredient according to the invention is characterized in that the said at least one solvent is a sebacic acid doubly esterified with two identical or different alcohols, each of the two alcohols being a linear or branched alcohol. or a mixture of isomers in any proportions where appropriate, or only one of the isomers if appropriate, the alcohol being C1-C30, preferably C1-C20, preferably C1-C10.
In one embodiment, the cosmetic ingredient according to the invention is characterized in that said at least one solvent is a dodecandioic acid doubly esterified with two identical or different alcohols, each of the two alcohols being chosen from the group consisting of by methanol, ethanol, propanols of empirical formula C3H80, butanols of formula C4H10O, pentanols of empirical formula C5H120, hexanols of empirical formula C6H40, heptanols of empirical formula C7H15O, octanols of empirical formula C8H180, nonanols of the empirical formula C9H20O, the decanols of the empirical formula C10H22O, the undecanol of the empirical formula CnH240, the dodecanol of the empirical formula Ci2H260, the tridecanol of the empirical formula C13H280, the tetradecanol of the empirical formula C14H30O, the pentadecanol of the empirical formula C15H320, the hexadecanol of the empirical formula C16H340, the heptadecanol of the empirical formula Ci7H360, the octadecanol of the empirical formula C18H380, the nonadecan of the formula ols of the empirical formula C19H40O and the eicosanols of the empirical formula C2oH420.
In one embodiment, the cosmetic ingredient according to the invention is characterized in that the said at least one solvent is a dodecanedioic acid doubly esterified with two identical or different alcohols, each of the two alcohols being chosen from the group consisting of methanol (CAS 67-56-1), ethanol (CAS 64-17-5), propan-1-ol (or n-propanol) (CAS 71-23-8), propan-2- ol (or isopropanol) (CAS 67-63-0), butan-1-ol (or n-butanol) (CAS 71-36-3), (R) -butan-2-ol (CAS 14898-79 -4), (S) -butan-2-ol (CAS 4221-99-2), 2-methylpropan-1-ol (CAS 78-83-1), 2-methylpropan-2-ol (CAS 75-65-0), 2-methylpropan-2-ol (CAS 75-65-0), pentan-1-ol (CAS 71-41-0), 3-methylbutan-1-ol (CAS 123 -51-3), 2-methylbutan-1-ol (CAS 137-32-6), 2,2-dimethylpropan-1-ol (CAS 75-84-3), pentan-3-ol (CAS 584-02-1), pentan-2-ol (CAS 6032-29-7), 3-methylbutan-2-ol (CAS 598-75-4), 2-methylbutan-2-ol (CAS 75 -85-4), hexan-1-ol (CAS 111-27-3 ), heptan-1-ol (CAS 111-70-6), dodecan-1-ol (CAS 112-53-8), octan-1-ol (CAS 111-87-5) , 2-ethylhexan-1-ol (CAS 104-76-7), octadecan-1-ol (CAS 112-92-5), decan-1-ol (CAS 112-30-1) and dodecan-1-ol (CAS 112-53-8).
In one embodiment, the cosmetic ingredient according to the invention is characterized in that the said at least one solvent is chosen from the group consisting of dioctyldodecyl dodecanedioate (CAS 129423-55-8) and diisocetyl dodecanedioate. (CAS 131252-83-0) and mixtures thereof.
Azelates are widely used solvents. They are derivatives of azelaic acid (CAS 123-99-9) of following formula:
Azelaic acid may be doubly esterified by the use of two identical or different alcohols.
In one embodiment, the cosmetic ingredient according to the invention is characterized in that the said at least one solvent is a sebacic acid doubly esterified with two identical or different alcohols, each of the two alcohols being a linear or branched alcohol. or a mixture of isomers in any proportions where appropriate, or only one of the isomers if appropriate, the alcohol being C 1 -C 30, preferably C 1 -C 20, preferably C 1 -C 10.
In one embodiment, the cosmetic ingredient according to the invention is characterized in that the said at least one solvent is an azelaic acid doubly esterified with two identical or different alcohols, each of the two alcohols being chosen from the group consisting of by methanol, ethanol, propanols of formula C3H80, butanols of formula C4H10O, pentanols of formula C5Hi20, hexanols of formula C6Hi40, heptanols of empirical formula C7Hi60, octanols of empirical formula C8Hi80, nonanols of the empirical formula C9H20O, decanols of the empirical formula C10H22O, the undecanol of the empirical formula CuH240, the dodecanol of the empirical formula Ci2H260, the tridecanol of the empirical formula C13H280, the tetradecanol of the empirical formula C14H30O, the pentadecanol of the empirical formula Ci5H320, the hexadecanol of the empirical formula C16H340, the heptadecanol of the empirical formula C17H360, the octadecanol of the empirical formula C18H380, the nonadecanol of the formula C19H40O crude formula and eicosanols of formula C20H42O.
In one embodiment, the cosmetic ingredient according to the invention is characterized in that said at least one solvent is azelaic acid doubly esterified with two identical or different alcohols, each of the two alcohols being chosen from the group consisting of methanol (CAS 67-56-1), ethanol (CAS 64-17-5), propan-1-ol (or n-propanol) (CAS 71-23-8), propan-2- ol (or isopropanol) (CAS 67-63-0), butan-1-ol (or n-butanol) (CAS 71-36-3), (R) -butan-2-ol (CAS 14898-79 -4), (S) -butan-2-ol (CAS 4221-99-2), 2-methylpropan-1-ol (CAS 78-83-1), 2-methylpropan-2-ol (CAS 75-65-0), 2-methylpropan-2-ol (CAS 75-65-0), pentan-1-ol (CAS 71-41-0), 3-methylbutan-1-ol (CAS 123 -51-3), 2-methylbutan-1-ol (CAS 137-32-6), 2,2-dimethylpropan-1-ol (CAS 75-84-3), pentan-3-ol (CAS 584-02-1), pentan-2-ol (CAS 6032-29-7), 3-methylbutan-2-ol (CAS 598-75-4), 2-methylbutan-2-ol (CAS 75 85-4), hexan-1-ol (CAS 111-27-3), heptan-1-ol (CAS 111-70-6), dodecan-1-ol (CAS 112-53-8), octan-1-ol (CAS 111-87-5), ethyl hexan-1-ol (CAS 104-76-7), octadecan-1-ol (CAS 112-92-5), decan-1-ol (CAS 112-30-1) and dodecan l-ol (CAS 112-53-8).
In one embodiment, the cosmetic ingredient according to the invention is characterized in that the said at least one solvent is chosen from the group consisting of dimethyl azelate (CAS 1732-10-1), the Di (2-ethylhexyl) azelate and mixtures thereof.
[000103] Glutarates are widely used solvents. They are derivatives of glutaric acid (CAS 110-94-1) of following formula:
[000104] Glutaric acid may be double esterified by the use of two identical or different alcohols.
In one embodiment, the cosmetic ingredient according to the invention is characterized in that the said at least one solvent is a sebacic acid doubly esterified with two identical or different alcohols, each of the two alcohols being a linear or branched alcohol. or a mixture of isomers in any proportions where appropriate, or only one of the isomers if appropriate, the alcohol being C1-C30, preferably C1-C20, preferably C1-C10.
In one embodiment, the cosmetic ingredient according to the invention is characterized in that the said at least one solvent is a doubly esterified glutaric acid with two identical or different alcohols, each of the two alcohols being chosen from the group consisting of by methanol, ethanol, propanols of formula C3H80, butanols of formula C4H10O, pentanols of formula C5Hi20, hexanols of formula C6Hi40, heptanols of empirical formula C7Hi60, octanols of empirical formula C8Hi80, nonanols of the empirical formula C9H20O, the decanols of the empirical formula C10H22O, the undecanol of the empirical formula CuH240, the dodecanol of the empirical formula C12H260, the tridecanol of the empirical formula C13H280, the tetradecanol of the empirical formula C14H30O, the pentadecanol of the empirical formula C15H320, the hexadecanol of the empirical formula C16H340, the heptadecanol of the empirical formula C17H360, the octadecanol of the empirical formula C18H380, the nonadecanol of Crude formula Ci9H40O and eicosanols of formula C20H42O.
In one embodiment, the cosmetic ingredient according to the invention is characterized in that the said at least one solvent is a doubly esterified glutaric acid with two identical or different alcohols, each of the two alcohols being chosen from the group consisting of methanol (CAS 67-56-1), ethanol (CAS 64-17-5), propan-1-ol (or n-propanol) (CAS 71-23-8), propan-2- o! (or isopropanol) (CAS 67-63-0), butan-1-ol (or n-butanol) (CAS 71-36-3), (R) -butan-2-ol (CAS 14898-79- 4), (S) -butan-2-ol (CAS 4221-99-2), 2-methylpropan-1-ol (CAS 78-83-1), 2-methylpropan-2-ol (CAS 75 -65-0), 2-methylpropan-2-ol (CAS 75-65-0), pentan-1-ol (CAS 71-41-0), 3-methylbutan-1-ol (CAS 123- 51-3), 2-methylbutan-1-ol (CAS 137-32-6), 2,2-dimethylpropan-1-ol. (CAS 75-84-3), pentan-3-ol (CAS 584-02-1), pentan-2-ol (CAS 6032-29-7), 3-methylbutan-2-ol (CAS 598 -75-4), 2-methylbutan-2-ol (CAS 75-85-4), hexan-1-ol (CAS 111-27-3), heptan-1-ol (CAS 111-70-6), dodecan-1-ol (CAS 112-53-8), octan-1-ol (CAS 111-87-5), 2-ethylhexan-1-ol (CAS 104 -76-7), octadecan-1-ol (CAS 112-92-5), decan-1-ol (CAS 112-30-1) and dodecan-1-ol (CAS 112-53- 8).
In one embodiment, the cosmetic ingredient according to the invention is characterized in that the said at least one solvent is chosen from the group consisting of dimethyl glutarate (CAS 1119-40-0) and diisobutyl glutarate. (CAS 71195-64-7), diisostearyl glutarate, dimethyl 2-methylglutarate (CAS 14035-94-0) and mixtures thereof.
[000109] Malonates are widely used solvents. They are derivatives of malonic acid (CAS 141-82-2) of the following formula;
[000110] Malonic acid can be double esterified by the use of two identical or different alcohols.
In one embodiment, the cosmetic ingredient according to the invention is characterized in that the said at least one solvent is a sebacic acid doubly esterified with two identical or different alcohols, each of the two alcohols being a linear or branched alcohol. or a mixture of isomers in any proportions where appropriate, or only one of the isomers if appropriate, the alcohol being C 1 -C 30, preferably C 1 -C 20, preferably C 1 -C 10.
In one embodiment, the cosmetic ingredient according to the invention is characterized in that said at least one solvent is a malonic acid doubly esterified with two identical or different alcohols, each of the two alcohols being chosen from the group consisting of by methanol, ethanol, propanols of the empirical formula C3H80, butanols of the empirical formula C4H10O, the pentanols of the empirical formula C5H120, the hexanols of the empirical formula C5Hi40, the heptanols of the empirical formula C7Hi60, the octanols of the empirical formula C8Hi80, nonanols of the empirical formula C9H20O, the decanols of the empirical formula C10H22O, the undecanol of the empirical formula CnH240, the dodecanol of the empirical formula C12H260, the tridecanol of the empirical formula C13H280, the tetradecanol of the empirical formula C14H30O, the pentadecanol of the empirical formula C15H320, the hexadecanol of the empirical formula C16H340, the heptadecanol of the empirical formula C17H360, the octadecanol of the empirical formula C18H380, the nonadecanol of Crude formula Ci9H40O and eicosanols of formula C20H42O.
In one embodiment, the cosmetic ingredient according to the invention is characterized in that said at least one solvent is a malonic acid doubly esterified with two identical or different alcohols, each of the two alcohols being chosen from the group consisting of methanol (CAS 67-56-1), ethanol (CAS 64-17-5), propan-1-ol (or n-propanol) (CAS 71-23-8), propan-2- ol (or isopropanol) (CAS 67-63-0), butan-1-ol (or n-butanol) (CAS 71-36-3), (R) -butan-2-ol (CAS 14898-79 -4), (S) -butan-2-ol (CAS 4221-99-2), 2-methylpropan-1-ol (CAS 78-83-1), 2-methylpropan-2-ol (CAS 75-65-0), 2-methylpropan-2-ol (CAS 75-65-0), pentan-1-ol (CAS 71-41-0), 3-methylbutan-1-ol (CAS 123 -51-3), 2-methylbutan-lo! (CAS 137-32-6), 2,2-dimethylpropan-1-ol (CAS 75-84-3), pentan-3-ol (CAS 584-02-1), pentan-2-ol ( CAS 6032-29-7), 3-methylbutan-2-ol (CAS 598-75-4), 2-methylbutan-2-ol (CAS 75-85-4), hexan-1-ol (CAS 111-27-3), heptan-1-ol (CAS 111-70-6), dodecan-1-ol (CAS 112-53-8), octan-1-ol ( CAS 111-87-5), 2-ethylhexan-1-ol (CAS 104-76-7), octadecan-1-ol (CAS 112-92-5), decan-1-ol (CAS 112-30-1) and dodecan-1-ol (CAS 112-53-8).
In one embodiment, the cosmetic ingredient according to the invention is characterized in that said at least one solvent is diethyl malonate (CAS 105-53-3).
In one embodiment, the cosmetic ingredient according to the invention is characterized in that said extract of karanja oil is extracted from a species selected from the group consisting of Pongamia glabra, Pongamia pinnata, Milletia pinnata, Demi indica, Gadelupa pinnata, Pongamia grandifolia, Robinia mitis, Tephrosia purpurea, Tephrosia hamiitoni, Tephrosia falciformis, Tephrosia vogellii and Tephrosia ianceoiata.
In one embodiment, the cosmetic ingredient according to the invention is characterized in that said extract of karanja oil is extracted from a species selected from the group consisting of Pongamia glabra and Milletia pinnata.
In one embodiment, the cosmetic ingredient according to the invention is characterized in that said extract of karanja oil is extracted from the species Milletia pinnata.
In one embodiment, the cosmetic ingredient according to the invention is characterized in that the mass percentage of said at least one solvent in said solution is between 20% and 60%.
In one embodiment, the cosmetic ingredient according to the invention is characterized in that the mass percentage of said at least one solvent in said solution is between 40% and 60%.
In one embodiment, the cosmetic ingredient according to the invention is characterized in that the mass percentage of said at least one solvent in said solution is about 50%.
In one embodiment, the cosmetic ingredient according to the invention is characterized in that the mass percentage of pongamol in said solution is greater than 1.30%.
In one embodiment, the cosmetic ingredient according to the invention is characterized in that the mass percentage of pongamol in said solution is greater than 1.20%.
In one embodiment, the cosmetic ingredient according to the invention is characterized in that the mass percentage of karanjine in said solution is less than 6%.
In one embodiment, the cosmetic ingredient according to the invention is characterized in that the mass percentage of karanjine in said solution is less than 5%.
In one embodiment, the cosmetic ingredient according to the invention is characterized in that the mass percentage of karanjine in said solution is less than 4.5%.
In one embodiment, the cosmetic ingredient according to the invention is characterized in that the mass percentage of karanjine in said solution is less than 4.3%.
In one embodiment, the cosmetic ingredient according to the invention is characterized in that the ratio mp0ngamoi / nnkaranjine in said solution is greater than 0.5.
In one embodiment, the cosmetic ingredient according to the invention is characterized in that the ratio mpongamoi / mi (aranjine in said solution is greater than 0.55.
The invention also relates to a process for the selective precipitation of pongamol (CAS 484-33-3) in a karanja oil comprising pongamol (CAS 484-33-3) and karanjine (CAS 521-88-0). ), characterized in that it comprises: 1) at least one step of adding to said at least one karanja oil at least one solvent selected from the group of the following diesters of formula (I), or mixtures thereof:
Formula (I) wherein: n is from 0 to 19; R and R ', which are identical or different, are alkyls originating from an esterification with a linear or branched alcohol of empirical formula CxH2x + 20, x being between 1 and 30, preferentially between 1 and 20, preferably between 1 and 10. R " is either a hydrogen atom or a C 1 -C 3 alkyl group, said addition having the effect of forming a light phase in the form of a solution and a heavy phase in the form of a precipitate, and 2) at least one separation step of the two phases obtained.
In one embodiment, the method according to the invention is characterized in that the extraction yield of said karanjine in said light phase in solution form is less than 50%.
In one embodiment, the method according to the invention is characterized in that the extraction yield of said pongamol in said light phase in the form of a solution is greater than 60%.
In one embodiment, the method according to the invention is characterized in that it causes a multiplication of the mass ratio mpongamoi / mkaranjine by a factor greater than 2.
In one embodiment, the method according to the invention is characterized in that during said step 1), the mass proportion of said at least one solvent introduced into said at least one karanja oil is between 60/40. and 20/80.
In one embodiment, the method according to the invention is characterized in that steps 1) and 2) are carried out at ambient temperature, for example at about 25 ° C.
In one embodiment, the process according to the invention is characterized in that said karanja oil is derived from a species selected from the group consisting of Pongamia glabra, Pongamia pinnata, Milletia pinnata, Denis indica and Gadelupa pinnata. , Pongamia grandifolia, Robinia mitis, Tephrosia purpurea, Tephrosia hamiltoni, Tephrosia falciformis, Tephrosia vogellii and Tephrosia lanceolata.
In one embodiment, the method according to the invention is characterized in that said karanja oil is derived from a species selected from the group consisting of Pongamia glabra and Milletia pinnata.
In one embodiment, the process according to the invention is characterized in that said karanja oil is derived from the species Millettia pinnata.
In one embodiment, the process according to the invention is characterized in that said karanja oil is a crude oil.
In one embodiment, the process according to the invention is characterized in that it comprises, in addition, at least one prior step of deodorizing said at least one karanja oil and / or at least one preliminary distillation step. of said at least one karanja oil, said steps, when both are present, can be performed in any order.
In one embodiment, the method according to the invention is characterized in that it further comprises: 3) at least one second addition step to said solution resulting from said step 2) of at least one solvent selected from the group of the following diesters of formula (I), or mixtures thereof:
Formula (I) wherein: n is from 0 to 19; R and R ', which are identical or different, are alkyls originating from an esterification with a linear or branched alcohol of empirical formula CxH2x + 20, x being between 1 and 30, preferentially between 1 and 20, preferably between 1 and 10. R " is either a hydrogen atom or a C 1 -C 3 alkyl group, said second adding step having the effect of forming a light phase in the form of a solution and a heavy phase in the form of a precipitate, and 4) a second step separating the two phases obtained, and in that the at least one solvent of step 3) is identical to or different from the at least one solvent of step 1).
In one embodiment, the process according to the invention is characterized in that the said at least one solvent is chosen from the group consisting of sebacates (n = 7), adipates (n = 3), succinates ( n = 1), dodecanedioates (n = 9), azelates (n = 6), glutarates (n = 2), malonates (n = 0), and mixtures thereof.
In one embodiment, the method according to the invention is characterized in that said at least one solvent is selected from the group consisting of sebacates (n = 7).
In one embodiment, the process according to the invention is characterized in that the said at least one solvent is diethyl sebacate (CAS 110-40-7).
[000144] In one embodiment, the process according to the invention is characterized in that R "is a hydrogen atom.
In one embodiment, the process according to the invention is characterized in that R "is a methyl.
In one embodiment, the method according to the invention is characterized in that x is between 1 and 20.
[000147] In one embodiment, the method according to the invention is characterized in that x is between 1 and 10.
In one embodiment, the method according to the invention is characterized in that n is between 1 and 10.
In one embodiment, the method according to the invention is characterized in that R is identical to R '.
[000150] In one embodiment, the method according to the invention is characterized in that R is different from R '.
In one embodiment, the process according to the invention is characterized in that the said at least one solvent is chosen from the group consisting of sebacates (n = 7), adipates (n = 3), succinates ( n = 1), dodecanedioates (n = 9), azelates (n = 6), glutarates (n = 2), malonates (n = 0), and mixtures thereof.
In one embodiment, the process according to the invention is characterized in that the said at least one solvent is a sebacic acid doubly esterified with two identical or different alcohols, each of the two alcohols being a linear or branched alcohol, or a mixture of isomers in any proportions where appropriate, or only one of the isomers where appropriate, the alcohol being C 1 -C 30, preferably C 1 -C 20, preferentially C 1 -C 10.
In one embodiment, the process according to the invention is characterized in that the said at least one solvent is a sebacic acid doubly esterified with two identical or different alcohols, each of the two alcohols being chosen from the group consisting of methanol, ethanol, propanols of formula C3H80, butanols of formula C4H10O, pentanols of formula C5H120, hexanols of formula C6Hi40, heptanols of formula C7Hi60, octanols of formula C8Hi80, nonanols of the empirical formula C9H20O, the decanols of the empirical formula C10H22O, the undecanol of the empirical formula CnH240, the dodecanol of the empirical formula C12H260, the tridecanols of the empirical formula C13H280, the tetradecanol of the empirical formula C14H30O, the pentadecanol of the empirical formula C15H320, the hexadecanols of Crude formula Ci6H340, heptadecanol of formula C14H360, octadecanol of formula C18H380, nonadecanol of crude formula e Ci9H40O and the eicosanols of formula C20H42O.
In one embodiment, the process according to the invention is characterized in that the said at least one solvent is a sebacic acid doubly esterified with two identical or different alcohols, each of the two alcohols being chosen from the group consisting of methanol. (CAS 67-56-1), ethanol (CAS 64-17-5), propan-1-ol (or n-propanol) (CAS 71-23-8), propan-2-ol ( or isopropanol) (CAS 67-63-0), butan-1-ol (or n-butanol) (CAS 71-36-3), (R) -butan-2-ol (CAS 14898-79-4 ), (S) -butan-2-ol (CAS 4221-99-2), 2-methylpropan-1-ol (CAS 78-83-1), 2-methylpropan-2-ol (CAS 75- 65-0), 2-methylpropan-2-ol (CAS 75-65-0), pentan-1-ol (CAS 71-41-0), 3-methylbutan-1-ol (CAS 123-51 -3), 2-methylbutan-1-ol (CAS 137-32-6), 2,2-dimethylpropan-1-ol (CAS 75-84-3), pentan-3-ol (CAS 584- 02-1), pentan-2-ol (CAS 6032-29-7), 3-methylbutan-2-ol (CAS 598-75-4), 2-methylbutan-2-ol (CAS 75-85 -4), hexan-1-ol (CAS 111-27-3), heptan-1-ol (CAS 111-70-6), dodecan-1-ol (CAS 112-53-8), octan-1-ol (CAS 111-87-5), 2-ethylhexan-1-ol ( CAS 104-76-7), octadecan-1-ol (CAS 112-92-5), decan-1-ol (CAS 112-30-1) and dodecan-1-ol (CAS 112- 53-8).
In one embodiment, the method according to the invention is characterized in that the said at least one solvent is selected from the group consisting of dioctyl sebacate (CAS 122-62-3), diethyl sebacate (CAS 110-40-7), dibutyl sebacate (CAS 109-43-3), diisopropyl sebacate (CAS 7491-02-3), and mixtures thereof.
In one embodiment, the process according to the invention is characterized in that the said at least one solvent is chosen from the group consisting of diethyl sebacate (CAS 110-40-7) and dibutyl sebacate (CAS). 109-43-3), diisopropyl sebacate (CAS 7491-02-3) and mixtures thereof.
In one embodiment, the process according to the invention is characterized in that the said at least one solvent is diethyl sebacate (CAS 110-40-7).
In one embodiment, the process according to the invention is characterized in that the said at least one solvent is a sebacic acid doubly esterified with two identical or different alcohols, each of the two alcohols being a linear or branched alcohol, or a mixture of isomers in any proportions where appropriate, or only one of the isomers where appropriate, the alcohol being C 1 -C 30, preferably C 1 -C 20, preferentially C 1 -C 10.
In one embodiment, the process according to the invention is characterized in that the said at least one solvent is an adipic acid doubly esterified with two identical or different alcohols, each of the two alcohols being chosen from the group consisting of methanol, ethanol, propanols of formula C3H80, butanols of formula C4H10O, pentanols of formula C5H120, hexanols of formula C6H140, heptanols of formula C7Hi60, octanols of formula C8Hi80, nonanols of the empirical formula C9H20O, the decanols of the empirical formula Ci0H22O, the undecanol of the empirical formula CnH240, the dodecanol of the empirical formula Ci2H250, the tridecanols of the empirical formula Ci3H280, the tetradecanol of the empirical formula C14H30O, the pentadecanol of the empirical formula Ci5H320, the hexadecanols of crude formula C16H340, heptadecanol of the empirical formula C17H360, the octadecanol of the empirical formula C18H3eO, the nonadecanol of the empirical formula C19H40O and the eicosanols of formula C20H42O.
In one embodiment, the process according to the invention is characterized in that the said at least one solvent is an adipic acid doubly esterified with two identical or different alcohols, each of the two alcohols being chosen from the group consisting of methanol. (CAS 67-56-1), ethanol (CAS 64-17-5), propan-1-ol (or n-propanol) (CAS 71-23-8), propan-2-ol ( or isopropanol) (CAS 67-63-0), butan-1-ol (or n-butanol) (CAS 71-36-3), (R) -butan-2-ol (CAS 14898-79-4 ), (S) -butan-2-ol (CAS 4221-99-2), 2-methylpropan-1-ol (CAS 78-83-1), 2-methylpropan-2-ol (CAS 75- 65-0), 2-methylpropan-2-ol (CAS 75-65-0), pentan-1-ol (CAS 71-41-0), 3-methylbutan-1-ol (CAS 123-51 -3), 2-methylbutan-1-ol (CAS 137-32-6), 2,2-dimethylpropan-1-ol (CAS 75-84-3), pentan-3-ol (CAS 584- 02-1), pentan-2-ol (CAS 6032-29-7), 3-methylbutan-2-ol (CAS 598-75-4), 2-methylbutan-2-ol (CAS 75-85 -4), hexan-1-ol (CAS 111-27-3), heptan-1-ol ( CAS 111-70-6), dodecan-1-ol (CAS 112-53-8), octan-1-ol (CAS 111-87-5), 2-ethylhexan-1-ol (CAS 104-76-7), octadecan-1-ol (CAS 112-92-5), decan-1-ol (CAS 112-30-1) and dodecan-1-ol (CAS 112-53). -8).
In one embodiment, the process according to the invention is characterized in that the said at least one solvent is chosen from the group consisting of dihexyl adipate (CAS 2091-24-9), adipate diisostearyl (CAS 62479-36-1), dicapryl adipate (CAS 108-63-4), di-C12-15 alkyl adipate, ditridecyl adipate (CAS 16958-92- 2), dicetyl adipate (CAS 26720-21-8), diisopropyl adipate (CAS 6938-94-9), diisobutyl adipate (CAS 141-04-8), dioctyl adipate (CAS 103-23-1), diisooctyl adipate (CAS 1330-86-5), diisononyl adipate (CAS 33703-08-1), diisodecyl adipate ( CAS 27178-16-1), diethyl adipate (CAS 141-28-6), dimethyl adipate (CAS 627-93-0), dihexyldecyl adipate (CAS 57533-90- 1), diheptylundecyl adipate (CAS 155613-91-5), dipropyl adipate (CAS 106-19-4), dioctyldodecyl adipate (CAS 85117-94-8), dibutyl adipate (CAS 105) -99-7), diisocetyl adipate (CAS 57533-90-1), dioctyl adipate (CAS 123-79-5) and mixtures thereof.
In one embodiment, the method according to the invention is characterized in that the said at least one solvent is chosen from the group consisting of diisopropyl adipate (CAS 6938-94-9), adipate dibutyl (CAS 105-99-7), dioctyl adipate (CAS 123-79-5) and mixtures thereof.
In one embodiment, the method according to the invention is characterized in that said at least one solvent is a double-esterified sebacic acid with two identical or different alcohols, each of the two alcohols being a linear or branched alcohol, or a mixture of isomers in any proportions where appropriate, or only one of the isomers where appropriate, the alcohol being C 1 -C 30, preferably C 1 -C 20, preferentially C 1 -C 10.
In one embodiment, the process according to the invention is characterized in that the said at least one solvent is a succinic acid doubly esterified with two identical or different alcohols, each of the two alcohols being chosen from the group consisting of methanol, ethanol, propanols of formula C3H80, butanols of formula C4H10O, pentanols of formula C5Hi20, hexanols of formula C6Hi40, heptanols of formula C7H160, octanols of formula C8Hi80, nonanols of the empirical formula C9H20O, the decanols of the empirical formula C10H22O, the undecanol of the empirical formula CnH240, the dodecanol of the empirical formula C12H260, the tridecanols of the empirical formula C13H280, the tetradecanol of the empirical formula C14H30O, the pentadecanol of the empirical formula C15H320, the hexadecanols of Crude formula Ci6H340, heptadecanol of formula C14H360, octadecanol of formula C18H380, nonadecanol of crude formula e C19H40O and the eicosanols of formula C20H42O.
In one embodiment, the process according to the invention is characterized in that the said at least one solvent is a succinic acid doubly esterified with two identical or different alcohols, each of the two alcohols being chosen from the group consisting of methanol. (CAS 67-56-1), ethanol (CAS 64-17-5), propan-1-ol (or n-propanol) (CAS 71-23-8), propan-2-ol ( or isopropanol) (CAS 67-63-0), butan-1-ol (or n-butanol) (CAS 71-36-3), (R) -butan-2-ol (CAS 14898-79-4 ), (S) -butan-2-ol (CAS 4221-99-2), 2-methylpropan-1-ol (CAS 78-83-1), 2-methylpropan-2-ol (CAS 75- 65-0), 2-methylpropan-2-ol (CAS 75-65-0), pentan-1-ol (CAS 71-41-0), 3-methylbutan-1-ol (CAS 123-51 -3), 2-methylbutan-1-ol (CAS 137-32-6), 2,2-dimethylpropan-1-ol (CAS 75-84-3), pentan-3-ol (CAS 584- 02-1), pentan-2-ol (CAS 6032-29-7), 3-methylbutan-2-ol (CAS 598-75-4), 2-methylbutan-2-ol (CAS 75-85 -4), hexan-1-ol (CAS 111-27-3), heptan-1-ol (CAS 111-70-6), dodecan-1-ol (CAS 112-53-8), octan-1-ol (CAS 111-87-5), 2-ethylhexan-1-ol ( CAS 104-76-7), octadecan-1-ol (CAS 112-92-5), decan-1-ol (CAS 112-30-1) and dodecan-1-ol (CAS 112- 53-8).
In one embodiment, the process according to the invention is characterized in that the said at least one solvent is chosen from the group consisting of didecyl succinate (CAS 10595-82-1) and dimethyl succinate (CAS). 106-65-0), diethyl succinate (CAS 123-25-1), dicapryl succinate (CAS 14491-66-8), diketearyl succinate (CAS 93280-98-9), diisobutyl succinate (CAS 925-06-4), diethylhexyl succinate (CAS 2915-57-3) and mixtures thereof.
In one embodiment, the process according to the invention is characterized in that the said at least one solvent is diethylhexyl succinate (CAS 2915-57-3).
In one embodiment, the process according to the invention is characterized in that the said at least one solvent is a 2-methylsuccinic acid doubly esterified with two identical or different alcohols, each of the two alcohols being a linear alcohol or branched, or a mixture of isomers in any proportions where appropriate, or only one of the isomers where appropriate, the alcohol being C1-C30, preferably Cj-Qo, preferably C1-C10.
In one embodiment, the process according to the invention is characterized in that the said at least one solvent is a 2-methyl acid! succinic double esterified with two identical or different alcohols, each of the two alcohols being selected from the group consisting of methanol, ethanol, propanols of the empirical formula C 3 H 5 O, the butanols of the empirical formula C 4 H 10 O, the pentanols of the empirical formula C 5 H 20, the hexanols of the empirical formula C6Hi40, the heptanols of the empirical formula C7Hi60, the octanols of the empirical formula C8Hi80, the nonanols of the empirical formula C9H20O, the decanols of the empirical formula CiOH22O, the undecols of the empirical formula ChH240, the dodecanol of the empirical formula Ci2H260, the tridecanols of the empirical formula C13H280, the tetradecanol of the empirical formula C14H30O, the pentadecanol of the empirical formula C15H320, the hexadecanol of the empirical formula C16H340, the heptadecanol of the empirical formula C17H360, the octadecanol of the empirical formula C18H380, the nonadecanol of the empirical formula C19H40O and the eicosanols of crude formula C20H42O.
In one embodiment, the process according to the invention is characterized in that the said at least one solvent is a 2-methyl succinic acid doubly esterified with two identical or different alcohols, each of the two alcohols being chosen from the group consisting of methanol (CAS 67-56-1), ethanol (CAS 64-17-5), propan-1-ol (or n-propanol) (CAS 71-23-8), propan-2 -ol (or isopropanol) (CAS 67-63-0), butan-1-ol (or n-butanol) (CAS 71-36-3), (R) -butan-2-ol (CAS 14898- 79-4), (S) -butan-2-ol (CAS 4221-99-2), 2-methylpropan-1-ol (CAS 78-83-1), 2-methylpropan-2-ol ( CAS 75-65-0), 2-methylpropan-2-ol (CAS 75-65-0), pentan-1-ol (CAS 71-41-0), 3-methylbutan-1-ol (CAS 123-51-3), 2-methylbutan-1-ol (CAS 137-32-6), 2,2-dimethylpropan-1-ol (CAS 75-84-3), pentan-3-ol ( CAS 584-02-1), pentan-2-ol (CAS 6032-29-7), 3-methylbutan-2-ol (CAS 598-75-4), 2-methylbutan-2-ol (CAS 75-85-4), hexan-1-ol (CAS 111-27-3), hr eptan-1-ol (CAS 111-70-6), dodecan-1-ol (CAS 112-53-8), octan-1-o! (CAS 111-87-5), 2-ethylhexan-1-ol (CAS 104-76-7), octadecan-1-ol (CAS 112-92-5), decan-1-ol ( CAS 112-30-1) and dodecan-1-ol (CAS 112-53-8).
In one embodiment, the process according to the invention is characterized in that the said at least one solvent is chosen from the group consisting of diethyl 2-methyl succinate (CAS 4676-51-1), 1-ethyl-4-methyl methyl succinate (CAS 204125-41-7), 1-methyl-4-methyl-2-methyl succinate (CAS 606491-29-6), dipropyl 2-methyl succinate (CAS 56108-32-8), diisopropyl 2-methyl succinate (CAS 75906-62-6), 1-butyl 2-methyl succinate and 4-methyl (CAS 878209-18-8), 2 di (2-methylpropyl) methyl succinate (CAS 18447-89-7), 1-pentyl and 4-methyl 2-methyl succinate (CAS 204125-40-6), 2-methyl succinate methyl and 4-hexyl (CAS 214280-22-5), di (1-methylpropyl) 2-methyl succinate (CAS 57983-31-0), di (1,1-dimethylethyl) 2-methylsuccinate ( CAS 108763-17-3), dipentyl 2-methyl succinate (CAS 56108-33-9), dihexyl 2-methyl succinate (CAS 32774-96-2), 2-methyl Diheptyl uccinate (CAS 51191-78-7), 1-methyl and 4-dodecyl 2-methyl succinate (CAS 214280-27-0), dioctyl 2-methyl succinate (CAS 131787-12-7) , 2-methyl succinate 1-methyl and 4-octadecyl, 2-methyl succinate didecyl, 2-methyl succinate didodecyl or lauryl, 2-methylsuccinate decanyl, 2-methylsuccinate 2-ethylhexanyl, their isomers and mixtures of isomers, and mixtures thereof.
In one embodiment, the process according to the invention is characterized in that the said at least one solvent is a sebacic acid doubly esterified with two identical or different alcohols, each of the two alcohols being a linear or branched alcohol, or a mixture of isomers in any proportions where appropriate, or only one of the isomers where appropriate, the alcohol being C 1 -C 30, preferably C 1 -C 20, preferentially C 1 -C 10.
In one embodiment, the process according to the invention is characterized in that the said at least one solvent is a dodecandioic acid doubly esterified with two identical or different alcohols, each of the two alcohols being chosen from the group consisting of methanol, ethanol, propanols of formula C3H80, butanols of formula C4H10O, pentanols of formula C5H120, hexanols of formula C6H140, heptanols of formula C7H160, octanols of formula C8Hi80, nonanols of the empirical formula C9H20O, the decanols of the empirical formula CioH220, the undecanol of the empirical formula ChH240, the dodecanol of the empirical formula Ci2H260, the tridecanols of the empirical formula Ci3H280, the tetradecanol of the empirical formula C14H30O, the pentadecanol of the empirical formula Ci5H320, the hexadecanols of Crude formula Ci6H340, heptadecanol of the empirical formula C17H360, the octadecanol of the empirical formula C18H380, the nonadecanol of the formula e crude Ci9H40O and eicosanols of formula C20H42O.
In one embodiment, the process according to the invention is characterized in that the said at least one solvent is a dodecanedioic acid doubly esterified with two identical or different alcohols, each of the two alcohols being chosen from the group consisting of methanol. (CAS 67-56-1), ethanol (CAS 64-17-5), propan-1-ol (or n-propanol) (CAS 71-23-8), propan-2-ol ( or isopropanol) (CAS 67-63-0), butan-1-ol (or n-butanol) (CAS 71-36-3), (R) -butan-2-ol (CAS 14898-79-4 ), (S) -butan-2-ol (CAS 4221-99-2), 2-methylpropan-1-ol (CAS 78-83-1), 2-methylpropan-2-ol (CAS 75- 65-0), 2-methylpropan-2-ol (CAS 75-65-0), pentan-1-ol (CAS 71-41-0), 3-methylbutan-1-ol (CAS 123- 51-3), 2-methylbutan-1-ol (CAS 137-32-6), 2,2-dimethylpropan-1-ol (CAS 75-84-3), pentan-3-ol (CAS 584 -02-1), pentan-2-ol (CAS 6032-29-7), 3-methylbutan-2-ol (CAS 598-75-4), 2-methylbutan-2-ol. (CAS 75-85-4), hexan-1-ol (CAS 111-27-3), heptan-1-ol (CAS 111-70-6), dodecan-1-ol ( CAS 112-53-8), octan-1-ol (CAS 111-87-5), 2-ethylhexan-1-ol (CAS 104-76-7), octadecan-1-ol (CAS 112-92-5), decan-1-ol (CAS 112-30-1) and dodecan-1-ol (CAS 112-53-8).
In one embodiment, the process according to the invention is characterized in that the said at least one solvent is chosen from the group consisting of dioctyldodecyl dodecanedioate (CAS 129423-55-8) and diisocetyl dodecanedioate (CAS). 131252-83-0) and mixtures thereof.
In one embodiment, the method according to the invention is characterized in that the said at least one solvent is a sebacic acid doubly esterified with two identical or different alcohols, each of the two alcohols being a linear or branched alcohol, or a mixture of isomers in any proportions where appropriate, or only one of the isomers where appropriate, the alcohol being C1-C30, preferably C1-C20, preferably C1-C10.
In one embodiment, the process according to the invention is characterized in that the said at least one solvent is azelaic acid doubly esterified with two identical or different alcohols, each of the two alcohols being chosen from the group consisting of methanol, ethanol, propanols of formula C3H80, butanols of formula C4H10O, pentanols of formula C5H12O, hexanols of formula C6Hi40, heptanols of formula C7Hi60, octanols of formula C8Hi80, nonanols of the empirical formula C9H20O, the decanols of the empirical formula CioH220, the undecanol of the empirical formula CnH240, the dodecanol of the empirical formula Ci2H260, the tridecanols of the empirical formula Ci3H2eO, the tetradecanol of the empirical formula Ci4H30O, the pentadecanol of the empirical formula Ci5H320, the hexadecanols of Crude formula Ci6H340, heptadecanol of formula C14H360, octadecanol of formula C18H380, nonadecanol of formula C19H40O and eicosanols of the empirical formula C2oH420.
In one embodiment, the process according to the invention is characterized in that the said at least one solvent is an azelaic acid doubly esterified with two identical or different alcohols, each of the two alcohols being chosen from the group consisting of methanol. (CAS 67-56-1), ethanol (CAS 64-17-5), propan-1-ol (or n-propanol) (CAS 71-23-8), propan-2-ol ( or isopropanol) (CAS 67-63-0), butan-1-ol (or n-butanol) (CAS 71-36-3), (R) -butan-2-ol (CAS 14898-79-4 ), (S) -butan-2-ol (CAS 4221-99-2), 2-methylpropan-1-ol (CAS 78-83-1), 2-methylpropan-2-ol (CAS 75- 65-0), 2-methylpropan-2-ol (CAS 75-65-0), pentan-1-ol (CAS 71-41-0), 3-methylbutan-1-ol (CAS 123-51 -3), 2-methylbutan-1-ol (CAS 137-32-6), 2,2-dimethylpropan-1-ol (CAS 75-84-3), pentan-3-ol (CAS 584- 02-1), pentan-2-ol (CAS 6032-29-7), 3-methylbutan-2-ol (CAS 598-75-4), 2-methylbutan-2-ol (CAS 75-85 -4), hexan-1-ol (CAS 111-27-3), heptan-1- ol (CAS 111-70-6), dodecan-1-ol (CAS 112-53-8), octan-1-ol (CAS 111-87-5), 2-ethylhexan-1-ol (CAS 104-76-7), octadecan-1-ol (CAS 112-92-5), decan-1-ol (CAS 112-30-1) and dodecan-1-ol (CAS 112 -53-8).
In one embodiment, the process according to the invention is characterized in that the said at least one solvent is chosen from the group consisting of dimethyl azelate (CAS 1732-10-1) and azelate. di (2-ethylhexyl) and mixtures thereof.
In one embodiment, the process according to the invention is characterized in that the said at least one solvent is a sebacic acid doubly esterified with two identical or different alcohols, each of the two alcohols being a linear or branched alcohol, or a mixture of isomers in any proportions where appropriate, or only one of the isomers where appropriate, the alcohol being C 1 -C 30, preferably C 1 -C 20, preferentially C 1 -C 10.
In one embodiment, the process according to the invention is characterized in that the said at least one solvent is a doubly esterified glutaric acid with two identical or different alcohols, each of the two alcohols being chosen from the group consisting of methanol, ethanol, propanols of formula C3H80, butanols of formula C4H10O, pentanols of formula C5Hi20, hexanols of formula C6Hi40, heptanols of formula C7Hi60, octanols of formula C8Hi80, nonanols of the empirical formula C 9 H 20 O, the decanols of the empirical formula C 10 H 20 O, the undecanol of the empirical formula CuH 2 40, the dodecanol of the empirical formula C 12 H 2 60, the tridecanols of the empirical formula C 13 H 280, the tetradecanol of the empirical formula C 14 H 30 O, the pentadecanol of the empirical formula C 15 H 31 O, the hexadecanols of Crude formula Ci6H340, heptadecanol of formula C14H360, octadecanol of formula C18H380, nonadecanol of crude formula e Ci9H40O and the eicosanols of formula C20H42O.
In one embodiment, the process according to the invention is characterized in that the said at least one solvent is a doubly esterified glutaric acid with two identical or different alcohols, each of the two alcohols being chosen from the group consisting of methanol. (CAS 67-56-1), ethanol (CAS 64-17-5), propan-1-ol (or n-propanol) (CAS 71-23-8), propan-2-ol ( or isopropanol) (CAS 67-63-0), butan-1-ol (or n-butanol) (CAS 71-36-3), (R) -butan-2-ol (CAS 14898-79-4 ), (S) -butan-2-ol (CAS 4221-99-2), 2-methylpropan-1-ol (CAS 78-83-1), 2-methylpropan-2-ol (CAS 75- 65-0), 2-methylpropan-2-ol (CAS 75-65-0), pentan-1-ol (CAS 71-41-0), 3-methylbutan-1-ol (CAS 123-51 -3), 2-methylbutan-1-ol (CAS 137-32-6), 2,2-dimethylpropan-1-ol (CAS 75-84-3), pentan-3-ol (CAS 584 -02-1), pentan-2-ol (CAS 6032-29-7), 3-methylbutan-2-ol (CAS 598-75-4), 2-methylbutan-2-ol (CAS 75- 85-4), hexan-1-ol (CAS 111-27-3), heptan-lo l (CAS 111-70-6), dodecan-1-ol (CAS 112-53-8), octan-1-ol (CAS 111-87-5), 2-ethylhexan-1-ol (CAS 104-76-7), octadecan-1-ol (CAS 112-92-5), decan-1-ol (CAS 112-30-1) and dodecan-1-ol (CAS 112 -53-8).
In one embodiment, the process according to the invention is characterized in that the said at least one solvent is chosen from the group consisting of dimethyl glutarate (CAS 1119-40-0) and diisobutyl glutarate (CAS). 71195-64-7), diisostearyl glutarate, dimethyl 2-methylglutarate (CAS 14035-94-0) and mixtures thereof.
In one embodiment, the method according to the invention is characterized in that the said at least one solvent is a sebacic acid doubly esterified with two identical or different alcohols, each of the two alcohols being a linear or branched alcohol, or a mixture of isomers in any proportions where appropriate, or only one of the isomers where appropriate, the alcohol being C 1 -C 4, preferably C 1 -C 20, preferentially C 1 -C 10.
In one embodiment, the process according to the invention is characterized in that the said at least one solvent is a malonic acid doubly esterified with two identical or different alcohols, each of the two alcohols being chosen from the group consisting of methanol, ethanol, propanols of formula C3H80, butanols of formula C4H10O, pentanols of formula C5Hi20, hexanols of formula C6Hi40, heptanols of formula C7H160, octanols of formula C8Hi80, nonanols of the empirical formula C9H20O, the decanols of the empirical formula C10H22O, the undecanol of the empirical formula CuH240, the dodecanol of the empirical formula C12H260, the tridecanols of the empirical formula C13H280, the tetradecanol of the empirical formula C14H30O, the pentadecanol of the empirical formula C15H320, the hexadecanols of Crude formula Ci6H340, heptadecanol of formula C17H360, octadecanol of formula C18H380, nonadecanol of formula C19H40O and the eicosanols of formula C20H42O.
In one embodiment, the process according to the invention is characterized in that the said at least one solvent is a malonic acid doubly esterified with two identical or different alcohols, each of the two alcohols being chosen from the group consisting of methanol. (CAS 67-56-1), ethanol (CAS 64-17-5), propan-1-ol (or n-propanol) (CAS 71-23-8), propan-2-ol ( or isopropanol) (CAS 67-63-0), butan-1-ol (or n-butanol) (CAS 71-36-3), (R) -butan-2-ol (CAS 14898-79-4 ), (S) -butan-2-ol (CAS 4221-99-2), 2-methylpropan-1-ol (CAS 78-83-1), 2-methylpropan-2-ol (CAS 75- 65-0), 2-methylpropan-2-ol (CAS 75-65-0), pentan-1-ol (CAS 71-41-0), 3-methylbutan-1-ol (CAS 123-51 -3), 2-methylbutan-1-ol (CAS 137-32-6), 2,2-dimethylpropan-1-ol (CAS 75-84-3), pentan-3-ol (CAS 584- 02-1), pentan-2-ol (CAS 6032-29-7), 3-methylbutan-2-ol (CAS 598-75-4), 2-methylbutan-2-ol (CAS 75-85 -4), hexan-1-ol (CAS 111-27-3), heptan-1-ol (CAS 111-70-6), dodecan-1-ol (CAS 112-53-8), octan-1-ol (CAS 111-87-5), 2-ethylhexan-1-ol ( CAS 104-76-7), octadecan-1-ol (CAS 112-92-5), decan-1-ol (CAS 112-30-1) and dodecan-1-ol (CAS 112- 53-8).
In one embodiment, the process according to the invention is characterized in that the said at least one solvent is diethyl malonate (CAS 105-53-3).
[000188] The invention also relates to a cosmetic formulation, characterized in that it comprises: at least one cosmetic ingredient according to the invention as described above; and at least one cosmetically acceptable vehicle.
[000189] The cosmetic formulation according to the invention may further comprise one or more organic or mineral complementary sunscreens.
Among the hydrophilic or lipophilic active organic filters active in the UV-A and / or UV-B, mention may be made, by way of example, of cinnamic derivatives, salicylic derivatives, camphor derivatives or derivatives thereof. triazine, benzophenone derivatives, dibenzoylmethane derivatives, β, β-diphenylacrylate derivatives, p-aminobenzoic acid derivatives, polymer filters and silicone filters.
Among the mineral filters, photoprotective agents acting by physical blocking (reflection and / or diffusion) of the UV radiation, which are pigments or even between 5 nm and 500 nm, preferably between 100 and 250 nm. These pigments or nanopigments are coated or uncoated metal oxides, for example nanopigments of titanium oxide, of iron oxide, of zinc oxide, of zirconium oxide or of cerium oxide. When they are coated, the coating agents are, for example, alumina and / or aluminum stearate.
[000192] The cosmetic formulation according to the invention may also comprise derivatives of tyrosine or dihydroxyacetone (DHA) which are artificial tanning agents and / or browning agents of the skin (self-tanning agents).
[000193] The cosmetic formulation according to the invention may further comprise conventional cosmetic adjuvants used as supports and formulation constituents chosen in particular from fatty substances, organic solvents, ionic or nonionic thickeners, softeners, opacifiers, emollients, silicones, anti-foam agents, surfactants, fillers, sequestering agents, polymers, propellants, basifying or acidifying agents, dyes, or any other ingredient usually used in cosmetics.
[000194] The fatty substances may consist of an oil or a wax or their mixtures, and they also comprise fatty acids, fatty alcohols and esters of fatty acids. The oils may be chosen from animal, vegetable, mineral or synthetic oils and in particular from liquid petroleum jelly, liquid paraffin, silicone oils, which may or may not be volatile, isoparaffins and poly-α-olefins. fluorinated and perfluorinated oils. Similarly, the waxes can be chosen from animal, fossil, vegetable, mineral or synthetic waxes known per se.
[000195] Among the organic solvents, mention may be made of lower alcohols and polyols.
The thickeners may be chosen in particular from crosslinked polyacrylic acids, guar gums and modified or unmodified celluloses such as hydroxypropyl guar gum, methylhydroxyethylcellulose and hydroxypropylmethylcellulose.
[000197] The cosmetic formulation according to the invention may further comprise conventional cosmetic adjuvants used as active agents, namely preservatives or stabilizers, such as antioxidants or stabilizers.
[000198] It may further comprise moisturizing agents, vitamins or perfumes.
[000199] The cosmetic formulation according to the invention can be in particular in the form of an emulsion, simple or complex (O / W, W / O, O / W / H or W / O / W) such that cream, a milk, a gel or a cream gel, and be prepared according to the techniques well known to those skilled in the art, in particular those intended for the preparation of oil-in-water type emulsions (O / W). ) or water-in-oil (W / O).
It may optionally be packaged in aerosol and be in the form of foam or spray.
The cosmetic formulation according to the invention can be used as a composition for protecting the human epidermis or the hair against ultraviolet rays, as an antisolar composition or as a makeup product.
[000202] The invention also relates to the use of a cosmetic formulation according to the invention as described above, as a solar cosmetic formulation.
[000203] The invention also relates to the use of a cosmetic formulation according to the invention as described above, as anti-aging cosmetic formulation.
Examples
Example 1 Determination of the Mass Percentage of Karanjine and of Pongamol by Liquid Chromatography [000204] In all the following examples, the mass percentages of pongamol and karanjine are measured by HPLC according to a conventional method.
[000205] The column used is a Gemini column NX-C18 hereinafter reference 00G-4454-50, Phenomenex whose characteristics are 250 x 4.6mm, 5pm, 110Â.
[0002061 The reagents used are the following:
Table 1 [0002071 The analytical conditions are as follows: __
Table 2 [000208] Calibration was carried out from a stock solution comprising 14.4 mg of crude karanjin standard (p = 95.7%) and 33.4 mg of crude pongamol (p = 90.0%) 50mL of DMSO.
[000209] The preparation of the range was carried out with DMSO.
[000210] The retention times are as follows:
Table 3 [000211] The chromatogram of a calibration solution is given in Figure 1.
[000212] The chromatogram of a sample of karanja oil is given in FIG. 2.
[000213] The LC Solutions® software makes it possible to determine the concentration (mg / ml) in karanjine and pongamol.
Example 2 Process According to the Invention [000214] A karanja oil which has undergone degumming and deodorization having the following concentrations of pongamol and karanjine is used:
Table 4
Step 1: molecular distillation [000215] A molecular distillation step is carried out on a KDL5 apparatus under the following conditions: distillation temperature 170 ° C., vacuum 10 -2 mbar, feed set at 250 ml / h.
[000216] The mass balance of the distillation is given below:
Table 5 [000217] The light distillation phase is then characterized:
Table 6
Step 2: Karanjine precipitation [000218] To the molecular distillation distilled karanja oil (the light phase of distillation) is added the same mass of diethyl sebacate (CAS 110-40-7) (proportions 50/50 ).
The mixture is stirred 24h at 15 ° C. A precipitate is formed. The suspension obtained is then filtered on an 11 μm filter.
[000220] The assessment of the precipitation is given below:
Table 7 [000221] The contents of pongamol and karanjine in the light phases in solution and heavy form in the form of precipitate are then measured:
Table 8 [000222] The light phase or supernatant is a solution composed of about 50% diethyl sebacate (CAS 110-40-7), and about 50% pongamol enriched karanja oil extract.
[000223] The extraction yields are given below:
Table 9 [000224] In conclusion, with a use of 50/50 diethyl sebacate (CAS 110-40-7), there is obtained: a 61.5% removal of the karanjine from the light phase or supernatant in the form of solution; an evolution of the mpongamoi / mkaranjine ratio by a factor of 2.46 (1.75 / 0.71); a pumphol extraction yield of 95.7%.
The light phase or supernatant in the form of a solution, once separated from the heavy phase in the form of a precipitate, is a cosmetic ingredient according to the invention consisting of a solution comprising an extract of karanja oil and diethyl sebacate. (CAS 110-40-7). This cosmetic ingredient / this solution may, for example, be incorporated directly into a cosmetic formulation, without elimination of diethyl sebacate (CAS 110-40-7) and without solubilization step of pongamol.
[000226] This cosmetic ingredient consisting of a solution is characterized as follows:
Table 10
Example 3: Precipitation Tests with Other Solvents According to the Invention [000227] A molecular distillation of a karanja oil from another batch than that used in Example 1 is carried out by means of a layer distiller industrial slurry under the following conditions: distillation temperature 170 ° C, vacuum 10 -2 mbar The molecular distillation karanja oil is characterized as follows:
Table 11 [000228] Precipitation tests are then carried out on karanja oil with various solvents: diethyl sebacate (CAS 110-40-7) (test 1); diisopropyl sebacate (CAS 7491-02-3) (test 2).
The mixture is stirred 24h at 15 ° C. A precipitate is formed. The suspension obtained is then filtered on an 11 μm filter.
[000230] The mass balance sheets of the tests are given below:
Table 12 [000231] The mass balances are similar.
[000232] The contents of pongamol and karanjine in the light phases in solution and heavy form in the form of precipitate are then measured:
Table 13 [000233] The extraction yields are given as follows:
Table 14 [000234] In conclusion, with a use of diethyl sebacate (CAS 110-40-7) at 20/80, the following results are obtained: elimination of 97.0% of the karanjine from the light phase or supernatant in the form of solution; an evolution of the mpongarnoi / mkaranjine ratio by a factor of 21.76 (3.70 / 0.17); a pongamol extraction yield of 65.1%.
[000235] In conclusion, with a use of diisopropyl sebacate (CAS 7491-02-3) at 20/80, there is obtained: a removal of 81.8% of the karanjine from the light phase or supernatant in the form of a solution ; an evolution of the mpongamoi / nnkaranjine ratio by a factor of 3.53 (0.6 / 0.17); - A pongamol extraction yield of 63.8%.
[000236] Diethyl sebacate is therefore superior to diisopropyl sebacate with respect to its ability to precipitate karanjine, the extraction yield of pongamol being similar.
Here again, the light phase or supernatant in the form of a solution, once separated from the heavy phase in the form of a precipitate, is a cosmetic ingredient according to the invention consisting of a solution comprising a karanja oil extract and a solvent (diethyl sebacate or diisopropyl sebacate). This cosmetic ingredient / this solution may for example be incorporated directly into a cosmetic formulation, without removing the solvent (diethyl sebacate or diisopropyl sebacate) and without solubilizing step pongamol.
Example 4: Precipitation tests with different proportions of diethyl sebacate [000238] Molecular distillation is carried out under the same conditions as those described in Example 1, from another batch of karanja oil. At the end of the molecular distillation, karanja oil is characterized as follows:
Table 15 [000239] Trials 1 to 8 of precipitation are then carried out on karanja oil with diethyl sebacate (CAS 110-40-7), according to different proportions of diethyl sebacate / karanja oil.
[000240] The light or supernatant phases in the form of a solution and heavy or precipitated are separated by centrifugation.
[000241] The mass balances of the tests are given below:
Table 16 (000242) The contents of pongamol and karanjine in the light (supernatant) and heavy (precipitated) phases are then measured:
Table 17 [000243] The extraction yields are given below:
Table 18 [000244] A curve representing the extraction yields of pongamol and karanjine in the light or supernatant phase in solution form as a function of the proportion of diethyl sebacate used is given in FIG. 3. FIG. evolution of the extraction yields of pongamol and karanjine as a function of the proportion of diethyl sebacate used.
[000245] Depending on the mass percentages of pongamol and karanjine, the proportion of solvent must be adjusted to obtain a mass percentage of karanjine according to the specifications and obtain a mp0ngam0 | / mkaranjine ratio greater than or equal to 0.5.
Here again, especially for tests 4-8, the light phase or supernatant in solution form, once separated from the heavy or precipitated phase, is a cosmetic ingredient according to the invention consisting of a solution comprising an extract of karanja oil and diethyl sebacate. This cosmetic ingredient / this solution may for example be incorporated directly into a cosmetic formulation, without removal of diethyl sebacate and without solubilization step of pongamol.
EXAMPLE 5 Example of a Formulation According to the Invention [000247] An example of a formulation according to the invention, as well as an example of a procedure, is given below:
Table 19 [000248] The cometic formulation is prepared according to the following procedure which comprises 9 steps: 1) In a separate mixer, mix all the components of phase A, with stirring at 60 ° C. and until complete homogenization ; 2) Cool to room temperature with constant stirring; 3) In parallel, mix in a second mixer, the constituents of phase B until complete homogenization; 4) Add at room temperature the phases A and B, until complete homogenization; 5) Mix in a third mixer the constituents of phase C; 6) Mix the phases (A + B) and C with stirring; 7) Shake for 20 minutes at 1500 rpm; 8) Mix (A + B + C) + D, until complete homogenization; 9) Add E to (A + B + C + D) while maintaining agitation.

权利要求:
Claims (16)
[1" id="c-fr-0001]
1. Cosmetic ingredient, characterized in that it consists of a solution of at least one karanja oil extract comprising pongamol (CAS 484-33-3) and karanjine (CAS 521-88-0) in at least one solvent selected from the group of compounds of formula (I) below, or mixtures thereof:

Formula (I) wherein: n is from 0 to 19; R and R ', which are identical or different, are alkyls originating from an esterification with a linear or branched alcohol of empirical formula CxH2x + 20, x being between 1 and 30, preferentially between 1 and 20, preferably between 1 and 10. R " is either a hydrogen atom or a C1-C3 alkyl group.
[2" id="c-fr-0002]
2. Cosmetic ingredient according to claim 1, characterized in that said at least one solvent is selected from the group consisting of sebacates (n = 7), adipates (n = 3), succinates (n = 1), dodecanedioates (n = 9), azelates (n = 6), glutarates (n = 2), malonates (n = 0), and mixtures thereof.
[3" id="c-fr-0003]
3. Cosmetic ingredient according to any one of the preceding claims, characterized in that said at least one solvent is selected from the group consisting of sebacates (n = 7).
[4" id="c-fr-0004]
4. Cosmetic ingredient according to any one of the preceding claims, characterized in that the said at least one solvent is diethyl sebacate (CAS 110-40-7).
[5" id="c-fr-0005]
5. Cosmetic ingredient according to any one of the preceding claims, characterized in that the mass percentage of said at least one solvar in said solution is between 20% and 60%.
[6" id="c-fr-0006]
6. Cosmetic ingredient according to any one of the preceding claims, characterized in that the mass percentage of pongamol in said solution is greater than 1.30%.
[7" id="c-fr-0007]
7. Cosmetic ingredient according to any one of the preceding claims, characterized in that the mass percentage of karanjine in said solution is less than 6%.
[8" id="c-fr-0008]
8. Cosmetic ingredient according to any one of the preceding claims, characterized in that the mpongamoi / mkaranjine ratio in said solution is greater than 0.5.
[9" id="c-fr-0009]
9. Cosmetic formulation, characterized in that it comprises: at least one cosmetic ingredient according to any one of the preceding claims; and at least one cosmetically acceptable vehicle.
[10" id="c-fr-0010]
10. Use of a cosmetic formulation according to claim 9, as a solar cosmetic formulation and / or as an anti-aging cosmetic formulation.
[11" id="c-fr-0011]
11. Process for the selective precipitation of pongamol (CAS 484-33-3) in a karanja oil comprising pongamol (CAS 484-33-3) and karanjin (CAS 521-88-0), characterized in that He understands :

1) at least one step of adding to said at least one karanja oil at least one solvent chosen from the group of the diesters of formula (I) below, or their mixtures: Formula (I) in which: n is between 0 and 19; R and R ', which are identical or different, are alkyls originating from an esterification with a linear or branched alcohol of empirical formula CxH2x + 20, x being between 1 and 30, preferentially between 1 and 20, preferably between 1 and 10. R " is either a hydrogen atom or a C 1 -C 3 alkyl group, said addition having the effect of forming a light phase in the form of a solution 2) at least one step of separating the two phases obtained.
[12" id="c-fr-0012]
12. The method of claim 11, characterized in that said at least one solvent is selected from the group consisting of sebacates (n = 7), adipates (n = 3), succinates (n = 1), dodecanedioates ( n = 9), azelates (n = 6), glutarates (n = 2), malonates (n = 0), and mixtures thereof.
[13" id="c-fr-0013]
13. Method according to any one of claims 11 to 12, characterized in that said at least one solvent is selected from the group consisting of sebacates (n = 7).
[14" id="c-fr-0014]
14. Process according to any one of Claims 11 to 13, characterized in that the said at least one solvent is diethyl sebacate (CAS 110-40-7).
[15" id="c-fr-0015]
15. Method according to any one of claims 11 to 14, characterized in that during said step 1), the mass proportion of said at least one solvent introduced into said at least one karanja oil is between 60/40 and 20. / 80.
[16" id="c-fr-0016]
16. Method according to any one of claims 11 to 15, characterized in that it further comprises at least one prior step of deodorizing said at least one karanja oil and / or at least one preliminary step of distillation of said at least one karanja oil, said steps, when both are present, can be performed in any order.

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同族专利:

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公开号 | 公开日

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BR112018001114B1|2021-06-29|

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EP3598999A1|2020-01-29|

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CN108024950A|2018-05-11|

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AU2016296922A1|2018-03-08|

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WO2017013264A1|2017-01-26|

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EP3325103A1|2018-05-30|

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CN108024950B|2021-05-11|

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JP2018521079A|2018-08-02|

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ES2764754T3|2020-06-04|

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BR112018001114A2|2018-09-11|

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EP3325103B1|2019-09-11|

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KR20180031748A|2018-03-28|

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US10245220B2|2019-04-02|

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CA2993598A1|2017-01-26|

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AU2016296922B2|2021-09-23|

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US20180207070A1|2018-07-26|

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FR3039063B1|2017-07-21|

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优先权:

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申请号 | 申请日 | 专利标题

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FR1556973A|FR3039063B1|2015-07-22|2015-07-22|PROCESS FOR ENRICHING PONGAMOL WITH KARANJA OIL|FR1556973A| FR3039063B1|2015-07-22|2015-07-22|PROCESS FOR ENRICHING PONGAMOL WITH KARANJA OIL|

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AU2016296922A| AU2016296922B2|2015-07-22|2016-07-22|Process for pongamol enrichment of karanja oil|

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CA2993598A| CA2993598A1|2015-07-22|2016-07-22|Process for pongamol enrichment of karanja oil|

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KR1020187005218A| KR20180031748A|2015-07-22|2016-07-22|A method for enriching the Pongga Mall of Karanja Oil|

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