Alkoxy-silanes compounds and related condensation products as cosmetic raw materials and for coating cosmetic powders

Abstract

There are described alkoxy-silanes compounds and related condensation products as cosmetic raw materials and for coating cosmetic powders; synthesis processes of such compounds and condensation products and production of coated cosmetic powders. Said cosmetic powders can be used for preparing cosmetic products such as anhydrous products for face/eyes/lips, cosmetic pencils and face/eyes emulsions.

Claims

1. A skin-friendly coating compound for the surface modification of cosmetic powders using sol-gel chemistry of general formula:
A-BC(1) where: A is a hydrocarbon radical having from 10 to 100 carbon atoms and formally derived from an AX precursor with X=OH or NH.sub.2, with melting or softening point higher than 25 C. and lower than 100 C., B is a ureic or urethane group of formula: ##STR00007## C is a propyl trialkoxyl silane group (CH.sub.2).sub.3Si(OR.sup.1).sub.x(OR.sup.2).sub.3-x where 0x3 of formula (3) ##STR00008## where R.sup.1 corresponds to an ethyl radical CH.sub.2CH.sub.3 and R.sup.2 to the methyl radical CH.sub.3.

2. A coating compound for cosmetic powders according to claim 1, wherein A is a hydrocarbon radical having from 15 to 25 carbon atoms, B is a urethane group, C is a propyl trialkoxyl silane group (CH.sub.2).sub.3Si(OR.sup.1).sub.x(OR.sup.2).sub.3-x where 0x3 where R.sup.1 corresponds to an ethyl radical CH.sub.2CH.sub.3 and R.sup.2 to the methyl radical CH.sub.3.

3. A coating compound for cosmetic powders according to claim 1, wherein said organic compound is the docosanil carbamoyl propyl triethoxysilane compound of formula (5) ##STR00009##

4. Coating compound for cosmetic powders, according to claim 1, obtained by reacting 3-isocyanatepropyltriethoxysilane compound of formula (4) ##STR00010## with an equimolar amount of an AX compound, in anhydrous decane at a temperature of 70-95 C. for 6-10 hours and in the presence of a catalyst of the addition reaction, the purification of the organic compound in the form of white waxy solid from the reaction environment via crystallization, filtration and drying, characterized in that said coating compound is in a 10% percentage by weight in 1:1 ethanol:isododecane mixture, subjected to acid or base catalysis, adapted to obtain the organic-inorganic hybrid compound by condensation of formula (6) ##STR00011## said organic-inorganic hybrid compound being adapted to be purified by filtration, drying and possible grinding to obtain a powdery solid having a particle size of <500 m.

5. Coating compound according to claim 4, wherein the grinding is adapted to obtain a powdery solid having a particle size of <250 m.

6. Coating compound according to claim 4, wherein the grinding is adapted to obtain a powdery solid having a particle size of <100 m.

7. Coating compound according to claim 4, wherein the powdery solid is adapted to be added to a cosmetic formulation in a percentage from 80% to 1%.

8. Coating compound according to claim 7, wherein the powdery solid is adapted to be added to a cosmetic formulation in a percentage from 50% to 5%.

9. Coating compound according to claim 7, wherein the powdery solid is adapted to be added to a cosmetic formulation in a percentage from 30% to 10%.

10. Coating compound according to claim 4, wherein the condensation reaction occurs in the presence of a suitable cosmetic substrate comprising surface silanols adapted to be functionalized through the formation of stable covalent bonds with the organic compound.

11. Coating compound according to claim 1, wherein it comprises the docosanil carbamoyl propyl triethoxysilane compound from 1 to 10% by weight with respect to a cosmetic substrate, conveying the compound by means of an appropriate solution in volatile organic solvents, adding an acid or basic solution for obtaining a cosmetic powder being adapted to be subjected to drying in oven at temperatures from 50 C. to 150 C. for 2-48 hours.

12. Coating compound according to claim 11, wherein it comprises the docosanil carbamoyl propyl triethoxysilane compound from 2 to 5% and in that said production process takes place at 80 to 100 C. for more than 24 hours.

13. A method of using the coating compound according to claim 1 for coating a cosmetic powder intended to the formation of a pressed powder foundation.

14. A method of using the coating compound according to claim 1 for coating a cosmetic powder intended to the formation of a lipstick.

15. A method of using the coating compound according to claim 1 for coating a cosmetic powder intended to the formation of a cosmetic pencil.

Description

EXAMPLES

(1) The following examples are intended to clarify the present invention without limiting it in any way.

Example 1

(2) Preparation of a Coating Phase Obtained by Reaction with a Linear Alcohol

(3) TABLE-US-00001 Name % (w/w) Phase A 3-(triethoxysilyl)propylisocyanate, 95% 43.870 1-docosanol 55.030 Zinc stearate 0.100 Phase B Ethanol 1.000

(4) The present coating phase is prepared by placing phase A in a reactor provided with stirrer, thermometer and condenser. The reaction is carried out under nitrogen flow, heating the mass to a temperature of 90 C. for about 10 hours up to the disappearance of the active isocyanate groups. This disappearance is evaluated by IR. Phase B is subsequently added at about 70 C.

(5) The product thus obtained has a whitish waxy consistency with a melting point of about 60 C.

Example 2

(6) Preparation of a Coating Phase Obtained by Reaction with a Branched Alcohol

(7) TABLE-US-00002 Name % (w/w) Phase A 3-(triethoxysilyl)propylisocyanate, 95% 35.360 Tetradecyloctadecanol 63.540 Zinc stearate 0.100 Phase B Ethanol 1.000

(8) The present coating phase is prepared by following the procedure shown in Example 1.

(9) The product thus obtained has a whitish waxy consistency with a melting point of about 35 C.

Example 3

(10) Preparation of a Coating Phase Obtained by Reaction with a Partially Esterified Glycol

(11) TABLE-US-00003 Name % (w/w) Phase A 3-(triethoxysilyl)propylisocyanate, 95% 27.830 C20-30 Glycol Isostearate 71.070 Zinc stearate 0.100 Phase B Isopropyl alcohol 1.000

(12) The present coating phase is prepared by following the procedure shown in Example 1.

(13) The product thus obtained has a whitish waxy consistency with a melting point of about 55 C.

Example 4

(14) Preparation of a Coating Phase Obtained by Reaction with an Amphiphilic Zwitterionic Molecule

(15) TABLE-US-00004 Name % (w/w) Phase A 3-(trimethoxysilyl)propylisocyanate, 95% 16.107 Lauryl Hydroxysultaine 82.793 Zinc stearate 0.100 Phase B Isopropyl alcohol 1.000

(16) The present coating phase is prepared by following the procedure shown in Example 1.

(17) The product thus obtained has a whitish waxy consistency with a softening point of about 37 C.

Example 5

(18) Preparation of a Coated Cosmetic Powder

(19) TABLE-US-00005 Name % (w/w) Phase A Talc 89.500 Phase B Coating phase obtained in example 1, 2, 3, 4 1.790 Ethanol 3.480 Isododecane 3.480 Phase C Hydrochloric acid solution (1.42N) 1.750

(20) The coated cosmetic powder of the example was obtained by loading phase A in a mixer and stirring it with a suitable impeller, phase B and phase C were atomized in sequence on the powder of phase A at room temperature. The wet powder is then unloaded into suitable containers and dried in an oven at 80 C. for 24 hours. The volatile contents after oven treatment should be <1%. Finally, the powder is sifted with a 200 mesh sieve. The surface tension of such a coated powder is 35.4 dyne/cm.

(21) The powder selected for this example is in no way limiting with respect to all the other cosmetic powders that may be used (mica, silica, etc.).

Example 6

(22) Preparation of a Coated Cosmetic Pigment

(23) TABLE-US-00006 Name % (w/w) Phase A Red iron oxide 89.500 Phase B Coating phase obtained in example 1, 2, 3, 4 1.790 Ethanol 3.480 Isododecane 3.480 Phase C Hydrochloric acid solution (1.42N) 1.750

(24) The coated cosmetic pigment of the example was obtained by loading phase A in a mixer and stirring it with a suitable impeller, phase B and phase C were atomized in sequence on the pigment of phase A at room temperature. The wet powder is then unloaded into suitable containers and dried in an oven at 80 C. for 24 hours. The volatile contents after oven treatment should be <1%. Finally, the pigment is sifted with a 200 mesh sieve. The surface tension of such a coated pigment is 33.9 dyne/cm.

(25) The pigment selected for this example is in no way limiting with respect to all the other cosmetic pigments that may be used (Titanium dioxide, Yellow iron oxide, Black iron oxide, etc.).

Example 7

(26) Preparation of a Coated Cosmetic Pigment

(27) TABLE-US-00007 Name % (w/w) Phase A Red 7 lake 87.360 Phase B Coating phase obtained in example 1, 2, 3, 4 3.930 Ethanol 3.480 Isododecane 3.480 Phase C Hydrochloric acid solution (1.42N) 1.750

(28) The coated cosmetic pigment of the example was obtained by loading phase A in a mixer and stirring it with a suitable impeller, phase B and phase C were atomized in sequence on the pigment of phase A at room temperature. The wet powder is then unloaded into suitable containers and dried in an oven at 80 C. for 24 hours. The volatile contents after oven treatment should be <1%. Finally, the pigment is sifted with a 200 mesh sieve. The surface tension of such a coated pigment is 35.4 dyne/cm.

(29) The pigment selected for this example is in no way limiting with respect to all the other cosmetic pigments, in the form of lakes, that may be used (Blue 1 lake, Yellow 5 lake, etc.).

Example 8

(30) Preparation of a Colored Cosmetic Emulsion

(31) TABLE-US-00008 Name % (w/w) Phase A Isododecane 33.900 Water 43.800 Glycerin 2.000 Butylene glycol 3.000 Squalane 1.000 Glyceryl oleate 1.000 Phase B Disteardimonium hectorite 1.800 Propylene carbonate 0.600 Titanium dioxide coated as in example 6 8.000 Red iron oxide coated as in example 6 0.500 Yellow iron oxide coated as in example 6 2.800 Black iron oxide coated as in example 6 0.200 Phase C Preservatives 1.400

Example 9

(32) Preparation of a Pressed Powder Foundation

(33) TABLE-US-00009 Name % (w/w) Phase A Talc coated as in example 5 75.000 Mica coated as in example 5 5.200 Titanium dioxide coated as in example 6 1.000 Red iron oxide coated as in example 6 0.600 Yellow iron oxide coated as in example 6 2.000 Black iron oxide coated as in example 6 0.200 Spherical silica coated as in example 5 10.700 Nylon-12 5.000 Phase B Preservatives 0.300

Example 10

(34) Preparation of a Lipstick

(35) TABLE-US-00010 Name % (w/w) Phase A Microcrystalline wax 25.000 Diisostearyl malate 48.650 Hydrogenated styrene/methyl styrene/indene 10.600 copolymer Phase B Titanium dioxide coated as in example 6 1.800 Red 7 lake coated as in example 7 0.700 Yellow 5 lake coated as in example 7 2.700 Blue 1 lake coated as in example 7 0.250 Caprylic/capric triglyceride 10.000 Phase C Preservatives 0.300

Example 11

(36) Preparation of a Cosmetic Pencil

(37) TABLE-US-00011 Name % (w/w) Phase A Octyldodecanol 48.000 Polyethylene 23.000 Hydrogenated polyisobutene 5.600 Isohexadecane 8.900 Phase B Disteardimonium hectorite 0.900 Propylene carbonate 0.300 Mica coated as in example 5 0.800 Yellow 5 lake coated as in example 7 1.500 Blue 1 lake coated as in example 7 10.700 Phase C Preservatives 0.300