CN-122011804-A - Organosilicon modified oil-soluble dye and preparation method and application thereof

CN122011804ACN 122011804 ACN122011804 ACN 122011804ACN-122011804-A

Abstract

The application relates to the technical field of makeup raw materials, and particularly discloses an organosilicon modified oil-soluble dye and a preparation method and application thereof. The preparation method comprises the steps of stirring and reacting a preparation raw material of T, Q, D, M structural units, acetic acid and a catalyst I to obtain a reaction liquid, carrying out aftertreatment on the reaction liquid to obtain the organic silicon resin, mixing the organic silicon resin, a polar organic solvent I and the catalyst II to obtain an organic silicon resin mixture, mixing the dye and the polar organic solvent II, then adding the mixture into the organic silicon resin mixture, continuing to stir and react to obtain the reaction liquid, and carrying out aftertreatment on the reaction liquid to obtain the organic silicon modified oil-soluble dye. The organosilicon modified oil-soluble dye has good compatibility and stability in oily cosmetics, good film forming effect, excellent makeup holding effect, difficult residue after makeup removal and wider applicability.

Inventors

WU YANYAN
XUE ZHONGXIN
LUO JIAHANG

Assignees

上海杰立化妆品科技有限公司

Dates

Publication Date: 20260512
Application Date: 20260119

Claims (10)

1. The organic silicon modified oil-soluble dye is characterized by comprising a dye and organic silicon resin grafted on the dye, wherein the structural formula of the organic silicon modified oil-soluble dye is shown as follows: ; Wherein Dye is Dye, R is methyl or phenyl; the organic silicon resin is prepared by condensation reaction of a preparation raw material comprising an M structural unit, a preparation raw material comprising a D structural unit, a preparation raw material comprising a Q structural unit and a preparation raw material comprising a T structural unit; a is the equivalent of the preparation raw material of the M structural unit, b is the equivalent of the preparation raw material of the D structural unit; c is the equivalent of the preparation raw material of the Q structural unit, d is the equivalent of the preparation raw material of the T structural unit; a. The ratio of b, c and d is (0.5-3): (2-50): (0-3): 1.
2. The silicone-modified oil-soluble dye according to claim 1, wherein in the silicone resin, the preparation raw material of the T structural unit includes any one of an aminosilane coupling agent, a mercaptosilane coupling agent, and an alkylsilane coupling agent.
3. The silicone-modified oil-soluble dye according to claim 1, wherein the silicone resin is characterized in that the preparation raw material of the Q structural unit comprises tetraethyl orthosilicate or sodium silicate.
4. The silicone-modified oil-soluble dye according to claim 1, wherein the raw material for preparing the D structural unit in the silicone resin comprises dimethyl dimethoxy siloxane or any one of hydroxy polydimethylsiloxane and diphenyl dimethoxy silane.
5. The silicone-modified oil-soluble dye according to claim 1, wherein the silicone resin is characterized in that the preparation raw material of the M structural unit comprises hexamethyldisiloxane or hexaphenyl disiloxane.
6. The method for preparing the organosilicon modified oil-soluble dye according to any one of claims 1 to 5, which is characterized by comprising the following steps: s1, preparation of organic silicon resin: Mixing a preparation raw material of a T structural unit, a preparation raw material of a Q structural unit, a preparation raw material of a D structural unit and a preparation raw material of an M structural unit, adding acetic acid, and stirring and mixing for 0.5-1 h to obtain a mixture; adding a catalyst I into the mixture, and stirring and reacting for 4-8 hours at 60-80 ℃ to obtain a reaction solution; S2, mixing the organic silicon resin and the polar organic solvent I, stirring and mixing at 60-120 ℃ for 0.5-2 hours, and then adding the catalyst II to obtain an organic silicon resin mixture; Mixing the dye with the polar organic solvent II, adding the mixture into the organic silicon resin mixture, continuously stirring and reacting for 8-12 hours to obtain a reaction solution, and performing aftertreatment on the reaction solution to obtain the organic silicon modified oil-soluble dye.
7. The method for producing a silicone-modified oil-soluble dye according to claim 6, wherein the equivalent ratio of the production raw materials of the T structural unit, the Q structural unit, the D structural unit and the M structural unit in the production of the S1 silicone resin is 1 (0 to 3): 2 to 50): 0.5 to 3.
8. The preparation method of the organic silicon modified oil-soluble dye according to claim 6, wherein the mass ratio of the dye to the organic silicon resin in the S2 organic silicon resin grafted dye is 1 (5-20).
9. The method for preparing the organosilicon modified oil-soluble dye according to claim 6, wherein the catalyst I comprises any one of concentrated hydrochloric acid, sulfuric acid, trifluoroacetic acid and trifluoromethanesulfonic acid.
10. The use of the silicone-modified oil-soluble dye according to any one of claims 1 to 5, characterized in that it is used in make-up.

Description

Organosilicon modified oil-soluble dye and preparation method and application thereof Technical Field The application relates to the technical field of makeup raw materials, in particular to an organosilicon modified oil-soluble dye, a preparation method and application thereof. Background In the cosmetic field, colorants are core materials for achieving the color appearance of the product, and are largely divided into soluble dyes and pigments insoluble in the medium used. The dye can be dissolved in a specified solvent, and the dye is used as a medium to color the object to be dyed. Water-soluble dyes and oil-soluble dyes are classified according to their solubility properties. Unlike insoluble pigments, which cover, reflect specific light by means of microparticles, dye molecular-level dissolution can color the medium itself, presenting a number of unique advantages. For example, the color-changing and color-changing effects are extremely transparent and clear, and the vividness and the color intensity are excellent. In particular, since the oil-soluble dye can change the color of the medium while substantially maintaining its original texture. Therefore, the oil-soluble dye has excellent skin feel and fusion degree, and the color cosmetic product added with the oil-soluble dye is better in ductility, smoother and lighter in touch, can better fit the skin, and avoids the common powdery feel and attachment feel of pigment products. Although the oil-soluble dye has the advantages, various raw materials can be heated and dissolved in the preparation process of the cosmetics, and then cooled to room temperature for discharging. In this process, although the solubility of the oil-soluble dye molecules increases after being heated, the solubility of the oil-soluble dye decreases after cooling, and it may recrystallize, precipitate or form ultrafine aggregates invisible to the naked eye, thereby causing problems of precipitation and uneven color of the cosmetic. Disclosure of Invention In order to improve the temperature stability of the oil-soluble dye, the application provides an organosilicon modified oil-soluble dye, and a preparation method and application thereof. In a first aspect, the application provides an organosilicon modified oil-soluble dye, which adopts the following technical scheme: The organic silicon modified oil-soluble dye comprises dye and organic silicon resin grafted on the dye, wherein the structural formula of the organic silicon modified oil-soluble dye is shown as follows: ; Wherein Dye is Dye, R is methyl or phenyl; the organic silicon resin is prepared by condensation reaction of a preparation raw material comprising an M structural unit, a preparation raw material comprising a D structural unit, a preparation raw material comprising a Q structural unit and a preparation raw material comprising a T structural unit; a is the equivalent of the preparation raw material of the M structural unit, b is the equivalent of the preparation raw material of the D structural unit; c is the equivalent of the preparation raw material of the Q structural unit, d is the equivalent of the preparation raw material of the T structural unit; a. The ratio of b, c and d is (0.5-3): (2-50): (0-3): 1. The M structural unit in the organic silicon resin is a monofunctional end capping unit, plays a role in controlling the molecular weight integrally, and avoids the influence of the formation of an excessive cross-linked network on the integral solubility of the material. The difunctional D structural unit plays a role in prolonging the flexible silicon chain, and obviously improves the solubility. The addition of D structural units simultaneously improves the film forming flexibility of the final product, and excessive D structural units impair the film forming property. Q is a tetrafunctional cross-linked structural unit, and the introduction of the reinforcing material into the film-forming rigidity, however, limits the increase in solubility. The trifunctional T structural unit is generally constructed by participation of a silicon-oxygen coupling agent molecule with a proper functional group, plays a role in connecting dye molecules with silicon resin, and can be introduced into the synthesis for increasing the solubility and also can be introduced into the structural unit with a lipophilic functional group. The organic silicon resin with different solubility and film forming property can be synthesized through the composition and proportion regulation of the structural units of the silicon resin. By adopting the technical scheme, the water-soluble dye molecules meeting the cosmetic requirements are converted into the oil-soluble dye loaded on the organic silicon resin, so that the optional range of the oil-soluble dye is widened. Meanwhile, the mode that the traditional oil-soluble dye is dissolved in a solvent system in a small molecule form is changed, and the polymer dye based on the organic silicon