TRANSPARENT COLORED COSMETIC INGREDIENT FOR COSMETIC PRODUCTS, POSSIBLY CAPABLE OF AUTOMATICALLY CHANGING COLOR WHEN IRRADIATED BY ULTRAVIOLET LIGHT

Abstract

A cosmetic ingredient for cosmetic products has a polymer structure which includes an emollient or film-forming cosmetic polymer which is transparent to light. An organic chromophore molecule is inserted and chemically linked into the polymer, which can be a fixed color molecule or a photochromic molecule capable of rapidly switching from one color to another. The colored or photochromic molecule is inserted and chemically linked by transesterification into a cosmetic oil provided with functionalities which are suitable for the chemical anchoring of the molecule and chemically linked to said oil. The cosmetic oil may be a silicone macrodiol functionalized with a photochromic derivative designed so as to ensure the transition between a colorless state and a colored state following irradiation with ultraviolet light.

Claims

1. A method for inserting a photochromic molecule into an emollient cosmetic polymer, wherein a cosmetic oil is functionalized by transesterification with a photochromic molecule provided with functionalities which are suitable for the polymer anchoring thereof, said functionalized cosmetic oil maintaining the cosmetic function of emollient oil.

2. The method according to claim 1, wherein said cosmetic oil consists of a polysiloxane.

3. The method according to claim 2, wherein said polysiloxane is bis-hydroxyethoxypropyl dimethicone.

4. The method according to claim 1, wherein said cosmetic oil consists of polymers derived from linoleic acid.

5. The method according to claim 1, wherein the transesterification of the photochromic molecule is performed in the presence of a tin complex at high temperature (>100 C.) and without solvent.

6. The method according to claim 1, wherein said cosmetic oil is a silicone macrodiol functionalized with a photochromic derivative designed so as to ensure the transition between a colorless state and a colored state following irradiation with ultraviolet light.

7. The method according to claim 6, wherein the macrodiol transesterified with the photochromic molecule is used as a monomer for the synthesis of polyurethane while maintaining the film-forming function.

8. The method according to claim 7, wherein the polyurethane is of the alkyl type.

9. The method according to claim 7, wherein the polyurethane is of the silicone type.

10. The method according to claim 6, wherein said photochromic derivative has a structure FC-C3-Et obtained as schematized hereinbelow: ##STR00003## including spiropyrans, wherein a functionalizing chain is inserted on the indolenic nitrogen by covalent anchoring to a macrodiol by means of a catalytic transesterification reaction.

11. The method according to claim 10, wherein said photochromic derivative with structure FC-C3-Et is obtained by the following procedure: a) alkylation of trimethylindolenine in the absence of solvent by using ester of lower alcohols obtained from omega-bromine acids with chain between C2 (ethyl brominacetate) and C12 (3-ethyl brominepropionate or the like) with reaction performed between 80 C. and 140 C. under nitrogen atmosphere from 1 to 48 hours, with stoichiometric ratio of indolenine to alkylator between 1:1 (mol) and 1:5 (mol) until obtaining a viscous liquid; b) dissolution of said viscous liquid in water and extraction with CH2CL2 to remove the excess alkylator until obtaining a colorless organic aqueous extracting phase; c) said aqueous phase is made basic, left under stirring for about 2 hours and then extracted with CH.sub.2CL2 to obtain an organic phase which is dried on anhydrous salt to produce a red viscous oil consisting of a mixture of indolenine and anhydrous base; d) removal of indolenine by distillation at reduced pressure to produce pure anhydrous base as very viscous red oil; e) condensation of said pure anhydrous base with methoxy-nitroresorcinaldehyde by preparing two distinct solutions of anhydrous base and aldehyde in ethanol, both of which are pre-heated at about 60 C., rapidly mixed with each other in a bath at 60 C. and kept at this temperature about 120 seconds with successive removal of the bath to obtain a solution which is left stirring for one night until obtaining a grey precipitate which is crystallized twice by absolute ethanol so as to obtain a final derivative with melting point at about 145 C. which appears as a white crystalline solid and is very soluble in common organic solvents but only partially soluble in hot isododecane.

12. The method according to claim 11, wherein the transesterification is performed according to the following protocol: a) preparation of a suspension mixture of a solvent consisting of bis-hydroxyethoxypropyl dimethicone, a derivative with structure FC-C3-Et, and a catalyst in heterogeneous phase based on dibutiltinoxyde, stirring and disposition thereof under vacuum; b) heating of the mixture to about 145 C. until transforming the suspension into a homogeneous solution; c) maintaining heating about 1 hour until obtaining a blue/green oil; d) cooling of the blue/green oil to room temperature, dilution thereof with heptane and subsequent disposition at about 20 C. for one night to cause the precipitation of the catalyst and possible other insoluble residuals and to obtain a resulting mixture devoid of the same; e) filtration of the resulting mixture and removal of the solvent until obtaining emollient oil with photochromic capacity.

Description

EXAMPLE 1: EYE SHADOW

TABLE-US-00001 % by weight viscosifier 0.2 skin conditioning agent 1.9 water 3.0 surfactant 2.9 SAMPLE I 14.0 emollient 2.0 dye 72.0 matting agent 4.0

EXAMPLE 2: EYE SHADOW

TABLE-US-00002 % by weight dye 28.0 skin conditioning agent 6.0 matting agent 20.0 viscosifier 19.0 SAMPLE I 20.0 skin conditioning agent 6.0 preservative 1

EXAMPLE 3: LIP GLOSS

TABLE-US-00003 % by weight emollient 48.0 skin conditioning agents 30.0 viscosifiers 10.0 dye 5 SAMPLE I 7.0

EXAMPLE 4: LIP GLOSS

TABLE-US-00004 % by weight skin conditioning agent 17.3 plasticizer 2.2 solvent 66.8 film-forming 9.6 dye 0.1 SAMPLE I 4.0

[0059] Furthermore, an example of a cosmetic composition is reported herein in which at least one cosmetic material (SAMPLE II) according to the present invention was used, in the percentage of 29% by weight, which has the film-forming function and the feature of being colored in a fixed manner.

EXAMPLE 5: LIP GLOSS

TABLE-US-00005 % by weight SAMPLE II 29.0 solvent 28.7 skin conditioning agent 42.3

[0060] The main advantage of the present invention, not expected by those skilled in the art, is that, by taking a cosmetic raw material with the function of emollient oil or film-forming oil and subjecting it to transesterification with a chromophore molecule, the main cosmetic function is maintained, adding, in the case of a photochromic molecule, the ability to change color if the cosmetic product is subjected to the UV component of solar radiation.

[0061] The apparent technical advantage is that, taking a cosmetic formulation already optimized with the emollient oil or the initial film-forming oil, this formulation lends itself to being easily implemented with the ability to change the color thereof, in application, without modifying the other cosmetic performances. (texture, sensory experience, hold, etc.).