Branched saturated hydrocarbon cosmetic ingredient

Abstract

A cosmetic ingredient including at least one plant squalane and at least one mixture of C24 to C48 alkanes, in at least dimeric form, chosen amongst the alkanes of formula (I), where n is 1 or 0, R.sub.1, R′.sub.1, R.sub.2, R′.sub.2, R.sub.3 and R′.sub.3, which may be identical or different, are chosen amongst hydrogen atoms, methyl radicals, and linear C8 to C30 alkyl radicals, at least one of R1, R′1, R2, R′2, R3 and R′3 is chosen amongst the linear C8 to C30 alkyl radicals, and at least one and at most one of R1, R′1, R2, R′2, R3 and R′3 is a methyl radical. The mixture of C24 to C48 alkanes have a viscosity between 12 and 25 mm2/s at 40° C.

Claims

1. A cosmetic ingredient comprising at least one plant squalane and at least one mixture of C24 to C48 alkanes, chosen amongst the alkanes of formula I, ##STR00017## wherein n is equal to 0, R.sub.1, R′.sub.1, and R.sub.2 are each a hydrogen atom —H, R′.sub.2 is a methyl radical, and R.sub.3 and R′.sub.3 are chosen amongst linear C8 to C30 alkyl radicals, and said mixture of C24 to C48 alkanes has a viscosity between 12 and 25 mm.sup.2/s at 40° C.

2. The ingredient according to claim 1, wherein the alkanes of formula I are a mixture of C30 to C36 alkanes.

3. The ingredient according to claim 1, further comprising at least one branched C24 to C48 alkane of general formula II, ##STR00018## wherein R.sub.1, R.sub.2 and R.sub.3, which may be identical or different, are chosen amongst linear C8 to C30 alkyl radicals and a hydrogen atom, and at most one of R.sub.1, R.sub.2 and R.sub.3 is a hydrogen atom.

4. The ingredient according to claim 3, wherein the at least one branched alkane of formula II is a C28 to C36 alkane.

5. The ingredient according to claim 3, wherein all of R.sub.1, R.sub.2, and R.sub.3 in Formula II, which may be identical or different, are chosen amongst the linear C8 to C30 alkyl radicals.

6. The ingredient according to claim 1, wherein the at least one plant squalane is olive squalane.

7. A method comprising combining the cosmetic ingredient according to claim 1 with an additional plant squalane to yield a composition containing at most 50% of the additional plant squalane.

8. A cosmetic ingredient comprising at least one plant squalane and at least one mixture of C24 to C48 alkanes, in at least dimeric form, chosen amongst the alkanes of formula I, ##STR00019## wherein R′.sub.1 and R.sub.1 are each a hydrogen atom, n is equal to 0, and R.sub.2, R′.sub.2, R.sub.3 and R′.sub.3 are chosen amongst linear C8 to C30 alkyl radicals and at least one and at most one of R.sub.2, R′.sub.2, R.sub.3 and R′.sub.3 is a methyl radical.

9. A cosmetic ingredient comprising: at least one plant squalane, and at least one mixture of C24 to C48 alkanes, in at least dimeric form, chosen amongst the alkanes of Formula I, ##STR00020## wherein n is equal to 0, R.sub.1, R′.sub.1, R.sub.2, R′.sub.2, R.sub.3 and R′.sub.3, which may be identical or different, are chosen amongst the group consisting of a hydrogen atom —H, a methyl radical, and linear C8 to C30 alkyl radicals, at least one of R.sub.1, R′.sub.1, R.sub.2, R′.sub.2, R.sub.3 and R′.sub.3, which may be identical or different, is chosen amongst the linear C8 to C30 alkyl radicals, and at least one and at most one of R.sub.1, R′.sub.1, R.sub.2, R′.sub.2, R.sub.3 and R′.sub.3 is a methyl radical, said mixture of C24 to C48 alkanes having a viscosity between 12 and 25 mm.sup.2/s at 40° C.

10. The ingredient according to claim 9, wherein the alkanes of formula I are a mixture of C30 to C36 alkanes.

11. The ingredient according to claim 9, further comprising at least one branched C24 to C48 alkane of general formula II, ##STR00021## wherein at most one of R.sub.1, R.sub.2 and R.sub.3 is a hydrogen atom, R1, R2 and R3, which may be identical or different, are chosen amongst linear C8 to C30 alkyl radicals and a hydrogen atom, and at most one of R1, R2 and R3 is a hydrogen atom.

12. The ingredient according to claim 11, wherein the at least one branched alkane of formula II is a C28 to C36 alkane.

13. The ingredient according to claim 11, wherein all of R.sub.1, R.sub.2, and R.sub.3 in Formula II, which may be identical or different, are chosen amongst the linear C8 to C30 alkyl radicals.

14. The ingredient according to claim 9, wherein the at least one plant squalane is olive squalane.

15. A method comprising combining the cosmetic ingredient according to claim 9 with an additional plant squalane to yield a composition containing at most 50% of the additional plant squalane.

Description

BRIEF DESCRIPTION OF THE DRAWINGS

(1) FIG. 1 is a graph showing the refractive index of the composition disclosed herein (D) as compared to the refractive indices of sugar cane squalane (A), shark squalane (B), and olive squalane (C).

(2) FIG. 2 is a chart showing the viscosity of the composition disclosed herein (D) as compared to the viscosities of sugar cane squalane (A), shark squalane (B), and olive squalane (C).

(3) FIG. 3 is a chart showing the consistency in g.s. of Product 1: Sugarcane squalane Neossance; Product 2: Plantasens OLIVE Squalane from Clariant; Product 3: Olive squalane (Squalive) Biosynthis; Product 4: 50% mixture of C20 to C36 alkanes+50% Olive squalane (Squalive) Biosynthis (composition S); and Product 5: 70% mixture of C24 to C36 alkanes+30% Olive squalane (Squalive) Biosynthis (composition r).

(4) FIG. 4 is a chart showing the cohesion in g.s. of Product 1: Sugarcane squalane Neossance; Product 2: Plantasens OLIVE Squalane from Clariant; Product 3: Olive squalane (Squalive) Biosynthis; Product 4: 50% mixture of C20 to C36 alkanes+50% Olive squalane (Squalive) Biosynthis (composition S); and Product 5: 70% mixture of C24 to C36 alkanes+30% Olive squalane (Squalive) Biosynthis (composition r).

(5) FIG. 5 is a chart showing the firmness in g. of Product 1: Sugarcane squalane Neossance; Product 2: Plantasens OLIVE Squalane from Clariant; Product 3: Olive squalane (Squalive) Biosynthis; Product 4: 50% mixture of C20 to C36 alkanes+50% Olive squalane (Squalive) Biosynthis (composition S); and Product 5: 70% mixture of C24 to C36 alkanes+30% Olive squalane (Squalive) Biosynthis (composition r).

(6) FIG. 6 is a chart showing tackiness in g. of Product 1: Sugarcane squalane Neossance; Product 2: Plantasens OLIVE Squalane from Clariant; Product 3: Olive squalane (Squalive) Biosynthis; Product 4: 50% mixture of C20 to C36 alkanes+50% Olive squalane (Squalive) Biosynthis (composition S); and Product 5: 70% mixture of C24 to C36 alkanes+30% Olive squalane (Squalive) Biosynthis (composition r).

(7) FIG. 7 is a chart showing the contact angle measurements after 1 s for Product 1: Sugarcane squalane Neossance; Product 2: Plantasens OLIVE Squalane from Clariant; Product 3: Coconut squalane (Squalive) Biosynthis; Product 4: 50% mixture of C24 to C48 alkanes+50% Coconut squalane (Squalive) Biosynthis; and Product 5: 70% mixture of C24 to C48 alkanes+30% Coconut squalane (Squalive) Biosynthis.

(8) FIG. 8 is a chart showing the contact angle measurements after 4 s for Product 1: Sugarcane squalane Neossance; Product 2: Plantasens OLIVE Squalane from Clariant; Product 3: Coconut squalane (Squalive) Biosynthis; Product 4: 50% mixture of C24 to C48 alkanes+50% Coconut squalane (Squalive) Biosynthis; and Product 5: 70% mixture of C24 to C48 alkanes+30% Coconut squalane (Squalive) Biosynthis.

DETAILED DESCRIPTION

(9) The invention relates to a cosmetic ingredient comprising at least one plant squalane and at least one mixture of C24 to C48 alkanes, in at least dimeric form, chosen amongst the alkanes of formula I,

(10) ##STR00004##
wherein n is equal to 1 or 0, at least one of R.sub.1, R′.sub.1, R.sub.2, R′.sub.2, R.sub.3 and R′.sub.3, which may be identical or different, is chosen amongst a group consisting of the linear or branched C8 to C30 alkyl radicals, at least one of R.sub.1, R.sub.2 and R.sub.3 is a hydrogen atom —H, at least one of R′.sub.1, R′.sub.2 and R′.sub.3 is a hydrogen atom —H, and at most one of R.sub.1, R′.sub.1, R.sub.2, R′.sub.2, R.sub.3 and R′.sub.3 is a methyl radical, said mixture of C24 to C48 alkanes having a viscosity between 12 and 25 mm.sup.2/s at 40° C.

(11) In an embodiment, at least one of R.sub.1, R′.sub.1, R.sub.2, R′.sub.2, R.sub.3 and R′.sub.3, which may be identical or different, is chosen amongst the linear C8 to C30 alkyl radicals. In an embodiment, R.sub.1, R′.sub.1, R.sub.2, R′.sub.2, R.sub.3 and R′.sub.3, which may be identical or different, are chosen amongst the group consisting of the hydrogen atoms —H, the methyl radicals and the linear or branched C8 to C30 alkyl radicals.

(12) In an embodiment, R.sub.1, R′.sub.1, R.sub.2, R′.sub.2, R.sub.3 and R′.sub.3, which may be identical or different, are chosen amongst the group consisting of the hydrogen atoms —H, the methyl radicals and the linear C8 to C30 alkyl radicals.

(13) In an embodiment, at least one of R.sub.1, R.sub.2 or R.sub.3 and at least one of R′.sub.1, R′.sub.2 or R′.sub.3 is a hydrogen atom.

(14) In an embodiment, R′.sub.1 is a methyl radical.

(15) In an embodiment, R′.sub.1 is a methyl radical, at least one of R.sub.1, R.sub.2 or R.sub.3 and at least one of R′2 or R′.sub.3 is a hydrogen atom —H.

(16) In an embodiment, n=0, R′.sub.1 is a methyl radical, R1, R2 and R′2 are hydrogen atoms —H, and R3 and R′3 are chosen amongst the linear or branched C8 to C30 alkyl radicals, and the alkanes of the at least one mixture of C24 to C48 alkanes, in at least dimeric form, are chosen amongst the alkanes of formula Ia.

(17) ##STR00005##

(18) In an embodiment, n=0, R′.sub.1 is a methyl radical, R1, R2 and R′2 are hydrogen atoms —H, and R3 and R′3 are chosen amongst the linear C8 to C30 alkyl radicals, and the alkanes of the at least one mixture of C24 to C48 alkanes, in at least dimeric form, are chosen amongst the alkanes of formula Ia.

(19) In an embodiment, n=1, R′.sub.1 is a methyl radical, R1 and R′2 are hydrogen atoms —H, and R2, R3 and R′3 are chosen amongst the linear or branched C8 to C30 alkyl radicals, and the alkanes of the at least one mixture of C24 to C48 alkanes, in at least dimeric form, are chosen amongst the alkanes of formula Ib.

(20) ##STR00006##

(21) In an embodiment, n=1, R′.sub.1 is a methyl radical, R1 and R′2 are hydrogen atoms —H, and R2, R3 and R′3 are chosen amongst the linear C8 to C30 alkyl radicals, and the alkanes of the at least one mixture of C24 to C48 alkanes, in at least dimeric form, are chosen amongst the alkanes of formula Ib.

(22) In an embodiment, n=0, R1 and R′1 are hydrogen atoms —H, and R2, R′2, R3 and R′3 are chosen amongst the linear or branched C8 to C30 alkyl radicals, and the alkanes of the at least one mixture of C24 to C48 alkanes, in at least dimeric form, are chosen amongst the alkanes of formula Ic.

(23) ##STR00007##

(24) In an embodiment, n=0, R1 and R′1 are hydrogen atoms —H, and R2, R′2, R3 and R′3 are chosen amongst the linear C8 to C30 alkyl radicals, and the alkanes of the at least one mixture of C24 to C48 alkanes, in at least dimeric form, are chosen amongst the alkanes of formula Ic.

(25) In an embodiment, the branched alkanes of formula I, Ia, Ib and Ic are obtained by successive dimerizations of fatty alcohols originating from the catalytic hydrogenation of the coconut methyl esters, and comprise dimers, trimers, quadrimers or pentamers, followed by dehydration and hydrogenation.

(26) In a preferred embodiment, the successive dimerizations are obtained by a Guerbet reaction.

(27) In an embodiment, the fatty alcohols originating from the catalytic hydrogenation of the coconut methyl esters are dodecanol and decanol.

(28) In an embodiment, the branched alkanes of formula I, Ia, Ib and Ic comprise 30 to 36 carbon atoms and consist primarily or dimers and trimers.

(29) In an embodiment, the branched alkanes of formula I, Ia, Ib and Ic are obtained by successive dimerizations, by Guerbet reactions, of dodecanol and decanol, followed by dehydration and hydrogenation.

(30) In an embodiment, the dimerization of decanol yields an octyldodecanol, which can then be dimerized with a dodecanol to yield a mixture of C32 isomers, consisting primarily of trimers. The medium can also comprise C24 dimers originating from the condensation of dodecanol with itself. The mixture is then subjected to a dehydration followed by a hydrogenation.

(31) In an embodiment, the branched alkanes of formula I, Ia, Ib and Ic comprise at least one C30 trimeric alkane obtained by successive dimerizations of decanol.

(32) In an embodiment, the branched alkanes of formula I, Ia, Ib and Ic comprise at least one C32 trimeric alkane obtained by successive dimerizations of decanol and dodecanol, followed by dehydration and hydrogenation.

(33) In an embodiment, the branched alkanes of formula I, Ia, Ib and Ic comprise at least one C36 trimeric alkane obtained by successive dimerizations of dodecanol, followed by dehydration and hydrogenation.

(34) In an embodiment, n is equal to 1.

(35) In an embodiment, n is equal to 0.

(36) In an embodiment, the alkyl radicals are chosen amongst linear C8 to C12 alkyl radicals.

(37) In an embodiment, at least one of R.sub.1, R′.sub.1, R.sub.2, R′.sub.2, R.sub.3 and R′.sub.3 is a C8 alkyl radical.

(38) In an embodiment, at least one of R.sub.1, R′.sub.1, R.sub.2, R′.sub.2, R.sub.3 and R′.sub.3 is a C9 alkyl radical.

(39) In an embodiment, at least one of R.sub.1, R′.sub.1, R.sub.2, R′.sub.2, R.sub.3 and R′.sub.3 is a C10 alkyl radical.

(40) In an embodiment, at least one of R.sub.1, R′.sub.1, R.sub.2, R′.sub.2, R.sub.3 and R′.sub.3 is a C11 alkyl radical.

(41) In an embodiment, at least one of R.sub.1, R′.sub.1, R.sub.2, R′.sub.2, R.sub.3 and R′.sub.3 is a C12 alkyl radical.

(42) In an embodiment, at least one of R.sub.1, R′.sub.1, R.sub.2, R′.sub.2, R.sub.3 and R′.sub.3 is a C13 alkyl radical.

(43) In an embodiment, at least one of R.sub.1, R′.sub.1, R.sub.2, R′.sub.2, R.sub.3 and R′.sub.3 is a C14 alkyl radical.

(44) In an embodiment, at least one of R.sub.1, R′.sub.1, R.sub.2, R′.sub.2, R.sub.3 and R′.sub.3 is a C15 alkyl radical.

(45) In an embodiment, at least one of R.sub.1, R′.sub.1, R.sub.2, R′.sub.2, R.sub.3 and R′.sub.3 is a C16 alkyl radical.

(46) In an embodiment, at least one of R.sub.1, R′.sub.1, R.sub.2, R′.sub.2, R.sub.3 and R′.sub.3 is a C17 alkyl radical.

(47) In an embodiment, at least one of R.sub.1, R′.sub.1, R.sub.2, R′.sub.2, R.sub.3 and R′.sub.3 is a C18 alkyl radical.

(48) In an embodiment, at least one of R.sub.1, R′.sub.1, R.sub.2, R′.sub.2, R.sub.3 and R′.sub.3 is a C19 alkyl radical.

(49) In an embodiment, at least one of R.sub.1, R′.sub.1, R.sub.2, R′.sub.2, R.sub.3 and R′.sub.3 is a C20 alkyl radical.

(50) In an embodiment, at least one of R.sub.1, R′.sub.1, R.sub.2, R′.sub.2, R.sub.3 and R′.sub.3 is a C21 alkyl radical.

(51) In an embodiment, at least one of R.sub.1, R′.sub.1, R.sub.2, R′.sub.2, R.sub.3 and R′.sub.3 is a C22 alkyl radical.

(52) In an embodiment, at least one of R.sub.1, R′.sub.1, R.sub.2, R′.sub.2, R.sub.3 and R′.sub.3 is a C23 alkyl radical.

(53) In an embodiment, at least one of R.sub.1, R′.sub.1, R.sub.2, R′.sub.2, R.sub.3 and R′.sub.3 is a C24 alkyl radical.

(54) In an embodiment, at least one of R.sub.1, R′.sub.1, R.sub.2, R′.sub.2, R.sub.3 and R′.sub.3 is a C25 alkyl radical.

(55) In an embodiment, at least one of R.sub.1, R′.sub.1, R.sub.2, R′.sub.2, R.sub.3 and R′.sub.3 is a C26 alkyl radical.

(56) In an embodiment, at least one of R.sub.1, R′.sub.1, R.sub.2, R′.sub.2, R.sub.3 and R′.sub.3 is a C27 alkyl radical.

(57) In an embodiment, at least one of R.sub.1, R′.sub.1, R.sub.2, R′.sub.2, R.sub.3 and R′.sub.3 is a C28 alkyl radical.

(58) In an embodiment, at least one of R.sub.1, R′.sub.1, R.sub.2, R′.sub.2, R.sub.3 and R′.sub.3 is a C29 alkyl radical.

(59) In an embodiment, at least one of R.sub.1, R′.sub.1, R.sub.2, R′.sub.2, R.sub.3 and R′.sub.3 is a C30 alkyl radical.

(60) In an embodiment, the C32 trimeric alkanes are obtained by the following reactions:

(61) Step 1: Successive Dimerizations

(62) ##STR00008##
Step 2: Dehydration

(63) ##STR00009##
Step 3: Hydrogenation

(64) ##STR00010##

(65) In an embodiment, the C36 trimeric alkanes are obtained by the following reactions:

(66) Step 1: Successive Dimerizations

(67) ##STR00011##
Step 2: Dehydration

(68) ##STR00012##
Step 3: hydrogenation

(69) ##STR00013##

(70) In an embodiment, the cosmetic ingredient is characterized in that it comprises, in addition, at least one branched C24 to C48 alkane of general formula II,

(71) ##STR00014##
wherein at least one of R.sub.1, R.sub.2 and R.sub.3, which may be identical or different, is chosen amongst the linear or branched C8 to C30 alkyl radicals,
and at most one of R.sub.1, R and R.sub.3 is a hydrogen atom.

(72) In an embodiment, at least one of R.sub.1, R.sub.2 and R.sub.3, which may be identical or different, is chosen amongst the linear C8 to C30 alkyl radicals

(73) In an embodiment, the branched alkane comprises 28 to 36 carbons.

(74) In an embodiment, none of R.sub.1, R.sub.2 and R.sub.3 is a hydrogen atom.

(75) In an embodiment, at least one of R.sub.1, R.sub.2 and R.sub.3 is a hydrogen atom.

(76) In an embodiment, at least one of R.sub.1, R.sub.2 and R.sub.3 is a C8 alkyl radical.

(77) In an embodiment, at least one of R.sub.1, R.sub.2 and R.sub.3 is a C9 alkyl radical.

(78) In an embodiment, at least one of R.sub.1, R.sub.2 and R.sub.3 is a C10 alkyl radical.

(79) In an embodiment, at least one of R.sub.1, R.sub.2 and R.sub.3 is a C11 alkyl radical.

(80) In an embodiment, at least one of R.sub.1, R.sub.2 and R.sub.3 is a C12 alkyl radical.

(81) In an embodiment, at least one of R.sub.1, R.sub.2 and R.sub.3 is a C13 alkyl radical.

(82) In an embodiment, at least one of R.sub.1, R.sub.2 and R.sub.3 is a C14 alkyl radical.

(83) In an embodiment, at least one of R.sub.1, R.sub.2 and R.sub.3 is a C15 alkyl radical.

(84) In an embodiment, at least one of R.sub.1, R.sub.2 and R.sub.3 is a C16 alkyl radical.

(85) In an embodiment, at least one of R.sub.1, R.sub.2 and R.sub.3 is a C17 alkyl radical.

(86) In an embodiment, at least one of R.sub.1, R.sub.2 and R.sub.3 is a C18 alkyl radical.

(87) In an embodiment, at least one of R.sub.1, R.sub.2 and R.sub.3 is a C19 alkyl radical.

(88) In an embodiment, at least one of R.sub.1, R.sub.2 and R.sub.3 is a C20 alkyl radical.

(89) In an embodiment, at least one of R.sub.1, R.sub.2 and R.sub.3 is a C21 alkyl radical.

(90) In an embodiment, at least one of R.sub.1, R.sub.2 and R.sub.3 is a C22 alkyl radical.

(91) In an embodiment, at least one of R.sub.1, R.sub.2 and R.sub.3 is a C23 alkyl radical.

(92) In an embodiment, at least one of R.sub.1, R.sub.2 and R.sub.3 is a C24 alkyl radical.

(93) In an embodiment, at least one of R.sub.1, R.sub.2 and R.sub.3 is a C25 alkyl radical.

(94) In an embodiment, at least one of R.sub.1, R.sub.2 and R.sub.3 is a C26 alkyl radical.

(95) In an embodiment, at least one of R.sub.1, R.sub.2 and R.sub.3 is a C27 alkyl radical.

(96) In an embodiment, at least one of R.sub.1, R.sub.2 and R.sub.3 is a C28 alkyl radical.

(97) In an embodiment, at least one of R.sub.1, R.sub.2 and R.sub.3 is a C29 alkyl radical.

(98) In an embodiment, at least one of R.sub.1, R.sub.2 and R.sub.3 is a C30 alkyl radical.

(99) In an embodiment, the at least branched alkane of formula II is obtained by dehydrogenation of a C24 to C48 Guerbet alcohol of general formula III,

(100) ##STR00015##
wherein R.sub.1, R.sub.2 and R.sub.3 have the values defined above, followed by a hydrogenation.

(101) In an embodiment, the at least C36 branched alkanes are obtained by dehydrogenation of Isofol 36

(102) ##STR00016##
followed by a hydrogenation, to obtain 17-methylpentatriacontane. In an embodiment, the cosmetic ingredient can moreover comprise C18 to C28 alkanes of general formula I, obtained by dehydrogenation of alcohols originating from plant sources.

(103) The dimerizations are carried out by a Guerbet reaction, starting from linear alcohols; alcohols branched in position 2 are obtained. The Guerbet reactions are run in the presence of hydroxides or metal alkoxides and Raney nickel catalysts at temperatures above 220° C. and under pressure. Reaction conditions such as those described in the patent US 2003/0181770 in the name of COGNIS can also be used.

(104) The Guerbet alcohols or at least dimeric alcohols used can also be purchased, for example, from the company SASOL.

(105) The dehydration reactions are run according to the conventional high-temperature methods in the presence of alumina or according to methods described, for example, in the patent application WO2010121591 in the name of SASOL. In another variant of the invention, the alkanes can be obtained from fatty alcohols by hydrogenolysis of the hydroxyl function, in the presence of hydrogen and of a metal catalyst.

(106) The hydrogenation reactions are carried out by implementation of conventional catalysts such as nickel catalysts marketed by the company Johnson Matthey or by new-generation palladium catalysts, such as those described in the publication by R. Ciriminna et al., in Org. Process Res. Dev., 2014, 18(9), pp. 1110-1115.

(107) The invention also relates to the use of the cosmetic ingredient according to the invention, in combination with a plant squalane, to yield a composition of which the organoleptic and sensory properties are preserved, while using less plant squalane.

(108) It relates to the use of the cosmetic ingredient according to the invention, in combination with a plant squalane, for preparing a composition of which the organoleptic and sensory properties are preserved, while replacing at least 50% of plant squalane in the composition.

(109) The invention also relates to a composition containing at most 50% plant squalane in combination with the cosmetic ingredient according to the invention.

(110) The invention also relates to a composition comprising at most 50% plant squalane in combination with the cosmetic ingredient according to the invention.

(111) The invention also relates to a composition comprising 30 to 50% plant squalane in combination with 50 to 70% of the cosmetic ingredient according to the invention.

EXAMPLES

(112) I—General Conditions:

(113) Dimerization Reaction:

(114) The Guerbet reaction between two identical or different alcohols yields a mixture consisting of different isomers. This synthesis is carried out in the presence of a mixture of two alcohols, preferably in an equimolar ratio and in the presence of an alkaline base and of a catalyst based on copper oxide.

(115) Dehydration Method:

(116) The reactor used is a continuous tubular reactor which has the following characteristics: Inner diameter: 12.5 mm Total height: 370 mm Height of the catalyst bed: 100 mm

(117) The catalyst bed is placed at mid-height of the reactor. A thermocouple is placed at the core of this bed. The latter is held by a grate on which silica wool is placed. Above the bed, silica wool is added, in order to immobilize the catalyst bed.

(118) For this dehydration step, the catalyst used is an industrial alumina (Al.sub.2O.sub.3 99%).

(119) A weight of 6.436 g was loaded into the reactor, or a volume of 11.9 mL.

(120) Hydrogenation Reactions

(121) The hydrogenation reactions take place in a batch reactor having a capacity of one liter. The operating conditions are specified below.

(122) The alkene and the catalyst (Raney nickel) are introduced into the reactor at ambient temperature. The reactor is rendered inert with 3×5 bar of nitrogen, and the temperature is raised to the working temperature of 180° C. 5 bar dihydrogen are then introduced. After two hours, the temperature is raised to 200° C. The reaction is then maintained for an additional 3 h.

(123) II Obtention of the Alkanes in at Least Dimeric Form

(124) II-1 Obtention of the C30 Alkanes in at Least Dimeric Form

(125) Guerbet reaction between decanol and octyldodecanol (obtained by dimerization of decanol). The decanol is a fatty alcohol originating from the catalytic hydrogenation of coconut methyl esters.

(126) The desired reaction between decanol and octyldodecanol yields a mixture of C30 isomers consisting mostly of trimers. See diagrams below. It can also give rise to the formation of C20 dimers originating from the reaction of decanol with itself.

(127) The mixture of alcohols is then dehydrated according to the general conditions described above.

(128) The mixture of alkenes obtained is then hydrogenated, yielding on average C30 trimeric alkanes, according to the invention.

(129) TABLE-US-00001 Consumption Iodine of dihydrogen Alkane alkene Alkane per 1 ton of formula index g viscosity Alkane flow alkene, kg H.sub.2 (average) I2/100 g 40° C., mm.sup.2/s point, ° C. 4.8 C30H62 <1 14 −54
II-2 Obtention of the C32 Alkanes in at Least Dimeric Form

(130) Guerbet reaction between dodecanol and octyldodecanol (obtained by dimerization of decanol). The dodecanol and decanol are fatty alcohols originating from the catalytic hydrogenation of coconut methyl esters.

(131) The desired reaction between dodecanol and octyldodecanol yields a mixture of C32 isomers consisting primarily of trimers. It can also give rise to the formation of C24 dimers originating from the reaction of dodecanol with itself.

(132) The mixture of alcohols is then dehydrated according to the general conditions described above.

(133) The mixture of alkenes obtained is then hydrogenated, yielding on average C32 trimeric alkanes, according to the invention.

(134) TABLE-US-00002 Consumption Iodine of dihydrogen Alkane alkene Alkane per 1 ton of formula index g viscosity Alkane flow alkene, kg H.sub.2 (average) I2/100 g 40° C., mm.sup.2/s point, ° C. 4.5 C32H66 <1 16 −30
II-3 Obtention of the C36 Alkanes in at Least Dimeric Form

(135) Guerbet reaction between dodecanol and decatetradecanol (obtained by dimerization of dodecanol). The dodecanol is a fatty alcohol originating from the catalytic hydrogenation of coconut methyl esters.

(136) The desired reaction between dodecanol and decatetradecanol yields a mixture of C36 isomers consisting primarily of trimers. It can also give rise to the formation of C24 dimers originating from the reaction of dodecanol with itself.

(137) The mixture of alcohols is then dehydrated according to the general conditions described above.

(138) The mixture of alkenes obtained is then hydrogenated, yielding on average C36 trimeric alkanes, according to the invention.

(139) TABLE-US-00003 Consumption Iodine of dihydrogen Alkane alkene Alkane per 1 ton of formula index g viscosity Alkane flow alkene, kg H.sub.2 (average) 12/100 g 40° C., mm.sup.2/s point, ° C. 4.0 C36H74 <1 20 −24
III Examples of Synthesis of Branched Alkanes of General Formulas II:
III-1 Dehydration

(140) The raw materials used are the following:

(141) TABLE-US-00004 Raw materials Reference Supplier 2-decyltetradecanol Isofol 24 SASOL 2-tetradecyloctadecanol Isofol 32 SASOL 2-hexadecyleicosanol Isofol 36 SASOL Alumina INDUSTRIAL 99% Silica wool VWR Nitrogen Industrial AIR LIQUIDE

(142) The LHSV (Liquid Hourly Space Velocity) corresponds to the flow rate of alcohol passing through the reactor, expressed in mL/min/mL of catalyst.

(143) TABLE-US-00005 Dehydration results Quantity of water Quantity produced of alkene per 1 ton produced T, d (mL/ Conver- of alco- per 1 ton of Alcohol ° C. LHSV min) sion hol, kg alcohol, kg Isofol 24 330 2.5 0.5 >99% 50.8 949.2 Isofol 32 330 2.5 0.5 >99% 38.6 961.4 Isofol 36 330 2.5 0   >99% 34.5 965.5

(144) TABLE-US-00006 Characterization of the alkenes Iodine alkene index Alkene Alkene formula g I.sub.2/100 g Alkene iC24 C24H48 75.5 Alkene iC32 C32H64 56.7 Alkene iC36 C36H72 50.4 Plant squalene C30H50 371.4 Marine squalene C30H50 371.4
III-2 Hydrogenation

(145) According to the protocol described above, part I-3, the alkanes having the characteristics given in the table below are obtained.

(146) TABLE-US-00007 Characterization of the alkanes Consumption of hydrogen per 1 Viscosity Appearance ton of alkene, Alkane 40° C. at ambient Alkane kg H2 formula mm.sup.2/s temperature Alkane i C24 6.0 C24H50  8.0 Liquid Alkane i C32 4.5 C32H66 Nd Solid Alkane i C36 4.0 C36H74 nd Solid Plant squalane 29.3 C30H62 21.7 Liquid Marine 29.3 C309H62 16.6 Liquid squalane
IV—Examples of Compositions According to the Invention Composition R

(147) A composition according to the invention is prepared by mixing: 50% of olive squalane, 35% of C36 alkane in at least dimeric form, 10% of C30 alkane in at least dimeric form 5% of branched C32 alkane.

(148) A composition which is non-greasy, fine and film-forming is obtained.

(149) The stability is equivalent to that of shark squalane.

(150) The viscosities at 40° C. in mm2/s and the refractive indexes are compared in the tables below and in FIGS. 1 and 2 with those of olive squalane, sugar cane squalane, shark squalane.

(151) Refractive Indexes (See FIG. 1)

(152) TABLE-US-00008 Product nomenclature Product tested Refractive index A Sugar cane squalane 1.4521 B Shark squalane 1.4520 C Olive squalane 1.4560 D Composition according to 1.4558 the invention
Viscosities at 40° C. in mm/s (See FIG. 2)

(153) TABLE-US-00009 Viscosity at Product nomenclature Product tested 40° C. in mm.sup.2/s A Sugar cane squalane 16.2 B Shark squalane 16.6 C Olive squalane 20.5 D Composition according to 21.7 the invention

(154) In conclusion, the viscosities and the refractive indexes of the composition according to the invention are equivalent to those of olive squalane.

(155) Composition S

(156) A composition according to the invention is prepared by mixing: 30% of olive squalane, 17.5% of C24 alkane in at least dimeric form, 52.5% of C36 alkane in at least dimeric form,

(157) Composition T

(158) A composition according to the invention is prepared by mixing: 50% of olive squalane, 10% of C20 alkane in at least dimeric form, 40% of C36 alkane in at least dimeric form,
V—Characterization of the Compositions According to the Invention by Texturometry

(159) A test reproducing the sensory characteristics was carried out, and the consistency, the cohesion, the firmness and tackiness were characterized for compositions according to the invention and squalanes.

(160) The protocols used are described in the thesis by Laura Gilbert. Caractérisation physico-chimique et sensorielle d'ingrédients cosmétiques: une approche méthodologique [Physicochemical and sensory characterization of cosmetic ingredients: a methodological approach]. Polymers. University of Havre, 2012, in particular pages 126 and 127, and in the publication by Laura Gilbert in 2 Colloids and surfaces A: Physicochem. Eng. Aspects 421 (2013) 150-163, page 152, paragraph 2.2.3.

(161) The apparatus used is a TA.XT Plus texturometer.

(162) In FIGS. 3, 4, 5 and 6, the results pertaining to the following compositions or ingredients have been collected: Product 1: Sugarcane squalane Neossance Product 2: Plantasens OLIVE Squalane from Clariant Product 3: Olive squalane (Squalive) Biosynthis Product 4: 50% mixture of C20 to C36 alkanes+50% Olive squalane (Squalive) Biosynthis (composition S) Product 5: 70% mixture of C24 to C36 alkanes+30% Olive squalane (Squalive) Biosynthis (composition r)

(163) FIG. 3 represents the results obtained for consistency in g.s. The results are subjected to a variance analysis (ANOVA), and no significant difference between the different products tested is observed.

(164) FIG. 4 represents the results obtained for cohesion in g.s. The results are subjected to a variance analysis (ANOVA), and no significant difference between the different products tested is observed.

(165) FIG. 5 represents the results obtained for firmness in g. The results are subjected to a variance analysis (ANOVA), and no significant difference between the different products tested is observed.

(166) FIG. 6 represents the results obtained for tackiness in g. The results are subjected to a variance analysis (ANOVA), and no significant difference between the different products tested is observed.

(167) VI—Characterization of the Compositions According to the Invention by Goniometry

(168) Compositions according to the invention and squalanes were characterized by goniometry according to the protocol described in the publication by G. Savary in Colloids and surfaces Biointerfaces 102 (2013) 371-378, on page 372, paragraph 2.2.1.

(169) The apparatus used is a Digidrop GBX.

(170) In FIGS. 7 and 8, the results pertaining to the following compositions or ingredients have been collected: Product 1: Sugarcane squalane Neossance Product 2: Plantasens OLIVE Squalane from Clariant Product 3: Coconut squalane (Squalive) Biosynthis Product 4: 50% mixture of C24 to C48 alkanes+50% Coconut squalane (Squalive) Biosynthis Product 5: 70% mixture of C24 to C48 alkanes+30% Coconut squalane (Squalive) Biosynthis

(171) The results are expressed in degree ° and subjected to a variance analysis (ANOVA)

(172) The results presented in FIG. 7 are contact angle measurements after 1 s.

(173) The results presented in FIG. 8 are contact angle measurements after 4 s.

(174) V—Cosmetic Formulations Comprising Compositions According to the Invention

(175) Make-Up Foundation Composition:

(176) TABLE-US-00010 Phase A: INCI Ingredients wt %/total weight Cetyl PEG/PPG-10/1 2.80 dimethicone Abil EM 90 Phenyl trimethicone 1 Composition according to 3 the invention S Cetearyl ethylhexanoate 2 Vegelight 1214 Plant hydrocarbons 1.8 Ingredients wt %/total weight Phase B: Mica 0.5 Red oxide and dimethicone 0.22 Yellow oxide and dimethicone 0.75 Black iron oxide and dimethicone 0.12 Titanium oxide and dimethicone 8.5 Phase C Sodium chloride 1.25 Phenoxyethanol 0.50 Butylene glycol 5.00 Water Sufficient quantity for 100 Perfume sufficient quantity
Dry Oil Composition

(177) TABLE-US-00011 Ingredients INCI wt %/total weight Phase A: Caprylic/capric triglyceride Neoderm MCT 10.00 Simmondsia chinensis Organic Jojoba oil 5.00 Composition according to the 59.9 invention S Phase B: Plant hydrocarbons VEGELIGHT 1214 20.00 Perfume sufficient quantity