CN113967182A

CN113967182A - Stable synergistic antioxidant cosmetic composition

Info

Publication number: CN113967182A
Application number: CN202111235397.9A
Authority: CN
Inventors: 李建彤; 李松涛; 董珊凤; 陈斌
Original assignee: Shanghai Pehchaolin Daily Chemical Co ltd
Current assignee: Shanghai Pehchaolin Daily Chemical Co ltd
Priority date: 2021-10-22
Filing date: 2021-10-22
Publication date: 2022-01-25

Abstract

The invention discloses a stable synergistic antioxidant cosmetic composition. The composition comprises the following raw material components: 10-50 wt% of tocopherol, 1-15 wt% of rosemary leaf extract, 0.1-5 wt% of dimethyl methoxy chromanol and 30-80 wt% of solvent.

Description

Stable synergistic antioxidant cosmetic composition

Technical Field

The invention relates to the technical field of cosmetics, in particular to a stable synergistic antioxidant composition and application thereof in cosmetics.

Background

Antioxidants are ingredients that inhibit the oxidation of other molecules. Ultraviolet and visible light can excite molecular oxygen in the skin to form high-activity singlet substances. Many of the inflammatory responses to uv radiation are caused by reactive oxygen species that ultimately activate the production of proinflammatory mediators, such as prostaglandins, leukotrienes, and cytokines, causing further damage to cells and tissues. The antioxidant can block the generation of active oxygen induced by ultraviolet rays, and further enhance anti-inflammatory and anti-aging activities.

The antioxidant application mainly has the following problems: the problem of mutual neutralization and offset of the antioxidants under the formulation conditions; the problem that antioxidants may be so unstable as to be oxidatively inactivated before they act, such as VC; antioxidants do not work as well as better at higher doses, e.g. at higher concentrations, the absorption of topically applied vitamin C does not increase as the percentage of vitamin C in the compound increases. In the prior art, a plurality of antioxidants are usually used in combination, but the complex system is complex, cannot form a uniform system, and is inconvenient to use.

There is therefore a great need in the art to provide a combination of antioxidants that is stable, pH independent and easy to use.

Disclosure of Invention

The invention aims to provide an antioxidant compound which can be completely dissolved in an oil phase or a water phase, is not limited by the pH condition of a formula (the antioxidant activity is not required to be stabilized by adjusting the pH), has stable antioxidant performance and can be widely used in the formula and production of various cosmetics.

In a first aspect of the present invention, there is provided a stable synergistic antioxidant cosmetic composition comprising the following raw material components, based on the total weight of the composition:

in another embodiment, the composition comprises the following raw material components, based on the total weight of the composition:

in another embodiment, the raw material components of the composition are tocopherol, rosemary leaf extract, dimethylmethoxychromanol, and a solvent.

In another embodiment, the solvent is selected from one or two or more of the following: ethanol, polyethylene glycol-8, 1, 3-butanediol and ethoxydiglycol.

In another embodiment, the composition is a light yellow to brown homogeneous liquid.

In a second aspect of the present invention, there is provided a process for the preparation of a composition provided by the present invention as described above, said process comprising the steps of: mixing tocopherol, rosemary leaf extract, dimethyl methoxy chromanol and a solvent to obtain the composition provided by the invention as described above.

In a third aspect of the invention, there is provided the use of a composition as provided herein, as described above, for the preparation of a product for application to the skin.

In a fourth aspect of the invention, there is provided a dermatological product comprising a composition as provided by the invention as described above, together with a cosmetically acceptable carrier.

In a fifth aspect of the invention, there is provided a method of preparing a dermatological product as described above, the method comprising the steps of: the composition provided by the present invention as described above is mixed with a cosmetically acceptable carrier to give the skin product provided by the present invention as described above.

Accordingly, the present invention provides an antioxidant combination which is stable, free of pH dependence, and convenient to use.

Detailed Description

The inventors have conducted extensive and intensive studies to select dimethylmethoxychromanol together with tocopherol and rosemary leaf extract as a combined antioxidant, and to select specific alcoholic solvents together with the combined antioxidant to form the stable synergistic antioxidant composition of the present invention. The present invention has been completed based on this finding.

As used herein, "tocopherol" refers to a hydrolysate of vitamin E, an oil-soluble substance; in one embodiment of the invention is DL-a-tocopherol of the formula C₂₉H₅₀O₂The molar mass is 430.72g/mol, and the compound is high-purity synthetic fertilityPhenol, having the structure shown in formula (I):

as used herein, "rosemary leaf extract" refers to an oil-soluble component extracted from the leaf portion of rosemary (Rosmarinus officinalis L.) using sunflower seed oil as a solvent. For example, but not limited to, the oil-soluble rosemary leaf extract using sunflower seed oil as an extraction solvent and sunflower seed oil as a solvent obtained from rosemary leaf parts by supercritical carbon dioxide extraction technology contains Carnosic acid (Carnosic acid) with a content of not less than 4.0 wt%, Carnosol (Carnosol) with a content of not less than 0.2 wt% and Rosmanol (Rosmanol) with respect to the total weight of sunflower seed oil and rosemary leaf extract, and the like, and the total weight of the rosemary leaf extract is 10-35 wt% and the sunflower seed oil content is 65-90% with respect to the total weight of sunflower seed oil and extract. In one embodiment of the invention, the rosemary leaf extract is a homogeneous oily liquid.

As used herein, "dimethylmethoxychromanol (dimethylmethoxychromanol)" refers to an oil-soluble compound having the structure shown in the following formula (II):

in one embodiment of the invention, the dimethylmethoxychromanol is a crystalline powder with a purity of 96% or more (HPLC detection, C18 column (250X 4.6mm, 5 μm), ACN and 0.05% FTA aqueous solution as mobile phase, gradient elution from 15% ACN to 100% ACN within 15min, flow rate 1.0ml/min, detection wavelength 220 nm).

As used herein, "room temperature" means 15-40 deg.C, preferably 20-35 deg.C, such as, but not limited to, 25-30 deg.C, and the like.

As used herein, the term "cosmetically acceptable carrier" refers to a carrier that allows a cosmetic or personal care product to be applied, including various excipients and diluents, which are not themselves essential active ingredients, and which do not have undue toxicity after application. Suitable carriers are well known to those of ordinary skill in the art. A sufficient discussion of cosmetically acceptable excipients can be found in the cosmetic hygiene specifications 2015 edition. Such carriers may include humectants, emulsifiers, thickeners, chelating agents, emollients, and the like in the composition. Such as, but not limited to, water, 1, 2-hexanediol, p-hydroxyacetophenone, butanediol, panthenol, dipotassium glycyrrhizinate, arginine, glycerol, betaine, sodium hyaluronate, propylene glycol, glyceryl stearate/PEG-100 stearate, glyceryl stearate, xanthan gum, hydroxyethyl cellulose, carbomer, disodium EDTA, isomeric hexadecanes, isooctyl palmitate, cetostearyl alcohol, polydimethylsiloxane, citric acid or a salt thereof, behenyl alcohol, beheneth, ceteth, pentaerythritol tetrakis (ethylhexanoate), squalane, cetyl ethylhexanoate, and the like.

As used herein, "DPPH" refers to 1, 1-diphenyl-2-trinitrophenylhydrazine having the structure shown in formula (III):

the invention provides a composition, which comprises raw material components of tocopherol, rosemary leaf extract, dimethyl methoxy chromanol and a solvent, wherein the weight of each component is as follows based on the total weight of the raw material components:

the amount of tocopherol can also be 25-45%, the amount of rosemary leaf extract can also be 5-10%, the amount of dimethylmethoxychromanol can also be 1-2%, and the amount of solvent can also be 40-60%.

In one embodiment of the invention, the raw material components of the composition consist of tocopherol, rosemary leaf extract, dimethylmethoxychromanol and a solvent.

The solvent in the raw material components of the composition provided by the present invention is an alcohol solvent or a mixture thereof, and in one embodiment of the present invention, ethanol, polyethylene glycol-8, 1, 3-butanediol, ethoxydiglycol, or a mixture thereof is used as the solvent in the raw material components of the composition.

The compositions provided herein can be obtained by mixing the raw material components, and in one embodiment of the invention, the mixing step comprises:

firstly, mixing a rosemary leaf extract and dimethyl methoxy chromanol to obtain uniform liquid 1;

secondly, mixing a solvent with the uniform liquid 1 to form a uniform clear solution 2;

in a third step, tocopherol is mixed with solution 2 to obtain the composition provided by the present invention.

In one embodiment of the present invention, the mixing in the first step at room temperature can be performed by conventional methods in the art, such as, but not limited to, stirring, high speed dispersion, or sonication, for example, using sonication for 3-10 min.

In one embodiment of the present invention, the above-mentioned second step of mixing at room temperature can form a homogeneous solution by conventional methods in the art, such as, but not limited to, stirring, high speed dispersion, sonication (3-10 minutes), and the like.

In one embodiment of the present invention, the third step is carried out at room temperature, and the mixing can be made uniform by conventional methods in the art, such as, but not limited to, stirring, high speed dispersion, sonication, and the like.

The compositions provided herein are liquid; in one embodiment of the invention, the composition is a light yellow to brown homogeneous liquid.

The composition provided by the invention has an antioxidant effect and can be used as an antioxidant in the preparation of skin products. In the manufacture of skin products, the compositions provided herein are typically incorporated into other phases or mixtures of phases as a single phase or as an ingredient in an oil phase.

The skin product includes skin care products and cosmetics, the skin product is not limited to specific formulations, and formulations such as smoothing toner, nourishing lotion, massage cream, nourishing cream, facial mask, essence, ointment, color cosmetic BASE, foundation cream, emulsion (oil-in-water or water-in-oil), gel, cream, spray and the like can be developed.

Although numerical ranges and parameters setting forth the broad scope of the invention are approximate, the values set forth in the specific examples are presented as precisely as possible. Any numerical value, however, inherently contains certain standard deviations found in their respective testing measurements. As used herein, "about" generally means that the actual value is within plus or minus 10%, 5%, 1%, or 0.5% of a particular value or range. Alternatively, the term "about" means that the actual value falls within the acceptable standard error of the mean, as considered by those skilled in the art. Except in the experimental examples, or where otherwise expressly indicated, it is to be understood that all ranges, amounts, values and percentages herein used (e.g., to describe amounts of materials, length of time, temperature, operating conditions, quantitative ratios, and the like) are to be modified by the word "about". Accordingly, unless indicated to the contrary, the numerical parameters set forth in the specification and attached claims are approximations that may vary depending upon the desired properties sought to be obtained. At the very least, these numerical parameters are to be understood as meaning the number of significant digits recited and the number resulting from applying ordinary carry notation.

Unless defined otherwise herein, the scientific and technical terms used herein have the same meaning as is commonly understood and used by one of ordinary skill in the art. Furthermore, as used herein, the singular tense of a noun, unless otherwise conflicting with context, encompasses the plural form of that noun; the use of plural nouns also covers the singular form of such nouns.

To make the features and effects of the present invention comprehensible to those skilled in the art, general description and definitions are made below with reference to terms and expressions mentioned in the specification and claims. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs.

The theory or mechanism described and disclosed herein, whether correct or incorrect, should not limit the scope of the present invention in any way, i.e., the present disclosure may be practiced without limitation to any particular theory or mechanism.

All features defined herein as numerical ranges or percentage ranges, such as values, amounts, levels and concentrations, are for brevity and convenience only. Accordingly, the description of numerical ranges or percentage ranges should be considered to cover and specifically disclose all possible subranges and individual numerical values (including integers and fractions) within the range.

The features mentioned above with reference to the invention, or the features mentioned with reference to the embodiments, can be combined arbitrarily. All features disclosed in this specification may be combined in any combination, provided that there is no conflict between such features and the combination, and all possible combinations are to be considered within the scope of the present specification. Each feature disclosed in this specification may be replaced by an alternative feature serving the same, equivalent, or similar purpose. Thus, unless expressly stated otherwise, the features disclosed are merely generic examples of equivalent or similar features.

The main advantages of the invention are: high oxidation resistance, good stability and convenient use.

The invention will be further illustrated with reference to the following specific examples. It should be understood that these examples are for illustrative purposes only and are not intended to limit the scope of the present invention. The experimental procedures, in which specific conditions are not noted in the following examples, are generally carried out according to conventional conditions or according to conditions recommended by the manufacturers. All percentages, ratios, proportions, or parts are by weight unless otherwise specified. The weight volume percentage units in the present invention are well known to those skilled in the art and refer to, for example, the weight of solute in a 100 ml solution. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art. In addition, any methods and materials similar or equivalent to those described herein can be used in the methods of the present invention. The preferred embodiments and materials described herein are intended to be exemplary only.

The source of the raw material components in the following examples:

and (3) tocopherol: available from DSM Nutritional Products Ltd.

Rosemary leaf extract: phytrox Rosemary L4-CA deod (from jan dekker)

Dimethyl methoxy chromanol: available from SOHO ANECO Chemicals Co., Limited

Ascorbic acid: available from DSM Nutritional Products Ltd.

Ascorbyl palmitate: available from DSM Nutritional Products Ltd.

The ethanol is special grade dideal ethanol: from Anhuite food products Ltd

1, 3-butanediol: purchased from DAICEL CORPORATION

Ethoxy diglycol: from Gattefoss é SAS

Polyethylene glycol-8: from The Dow Chemical Company

DPPH radical scavenging test method in the following examples:

(1) preparing solution

DPPH solution: accurately weighing DPPH, and preparing DPPH solution with a certain weight percentage by using absolute ethyl alcohol

Antioxidant solution: accurately weighing the antioxidant composition, selecting proper ethanol concentration (namely a mixed solvent described below) to prepare antioxidant composition solutions with different mass concentration gradients,

mixing solvent: a suitable ethanol-water ratio for formulating the antioxidant,

preparing DPPH solution with a certain weight percentage by using special-grade double dealdehydizing ethanol, preparing the DPPH solution and antioxidant composition solution with different concentration gradients (prepared by using a proper solvent (the mixed solvent), uniformly mixing according to the proportion of 5g to 5g, stirring for 1 minute, and standing and reacting for 30 minutes in a dark place; the absorbance of the sample was measured at 518nm with Lambda750 and recorded as A1.

Absorbance values for 5g of 0.016% DPPH solution +5g of mixed solvent A0 ═ 5g

Absorbance values for 5g antioxidant solution +5g mixed solvent a2 ═ 5g

DPPH free radical scavenging rate [1- (A1-A2)/A0 ]. multidot.100% (the larger the value, the stronger the antioxidant capacity)

Preparation examples 1 to 4

Preparation of antioxidant compositions 1-4

Antioxidant compositions 1-4 were prepared according to the ingredients of table 1 below, including the following steps:

(1) uniformly mixing and dissolving the raw material components A2 and A3 at room temperature to obtain a mixture 1;

(2) adding the raw material component B into the mixture 1, and carrying out ultrasonic dissolution for 5min until the mixture is uniform and transparent to obtain a mixture 2;

(3) adding the raw material component A1 into the mixture 2, and stirring and mixing uniformly to obtain the antioxidant composition.

TABLE 1

^*The content is calculated by the total weight of each raw material component in the composition

Test examples 1 to 4

DPPH radical scavenging test

DPPH radical scavenging rates were measured using antioxidant compositions 1 to 4 obtained in preparation examples 1 to 4, respectively.

The results are shown in Table 2.

TABLE 2

The results show that the antioxidant compositions 1,2 and 4 obtained in preparation examples 1,2 and 4 have excellent antioxidant effects.

Test examples 5 to 9

Stability test

The antioxidant compositions 1 to 4 obtained in preparation examples 1 to 4 were used as in test examples 1 to 4 to measure DPPH radical clearance, respectively, and DPPH radical clearance was measured after leaving the antioxidant compositions 1 to 4 for 1 month, 2 months and 3 months, respectively.

The results are shown in Table 3.

TABLE 3

The results show that the antioxidant compositions 1,2 and 4 obtained in preparation examples 1,2 and 4 are stable against oxidation.

Examples 10 to 15

(1) Compositions 10-15 were prepared according to the ingredients of table 4 below, with the process referring to the preparation steps of antioxidant compositions 1-4.

TABLE 4

^*The content is based on the total weight of each component in the composition

(2) The DPPH clearance was measured at 0.005%, 0.006%, 0.0075% and 0.010% levels (by weight of the combined antioxidant composition) for the formulated compositions according to Table 4. See table 5.

TABLE 5

The results show that at the same amount of antioxidant combination, the clearance of DPPH at each amount of tocopherol, rosemary leaf extract, and dimethylmethoxychromanol in combination is superior to that of other antioxidant combinations.

(3) Compositions 13, 14 and 16 were tested for DPPH free radical clearance after 1 month, 2 months and 3 months of storage under various conditions. The results are shown in Table 6.

TABLE 6

Antioxidant stability comparative experiment

The results show that under the 3M studied conditions, the DPPH clearance of composition 13 without vitamin C was higher than that of composition 14 under all conditions, and that the antioxidant effect was hardly changed significantly in each condition compared to the initial value.

Although composition 16 (containing no vitamin C) had lower initial DPPH clearance than composition 14 (containing vitamin C) under the 3M study conditions, composition 16 had higher stability than composition 14 under each condition after the 3M study, and had higher DPPH clearance than composition 14 after the 3M study.

Application example 17

Essence liquid

Accurately weighing the phase A raw materials, stirring and mixing uniformly at room temperature, heating to 85 ℃ to dissolve until the phase A raw materials are transparent, cooling to about 45 ℃, adding the phase B which is uniformly mixed in advance, stirring uniformly until the phase B is transparent, cooling, and detecting to be qualified after cooling to room temperature.

Application example 18

Oil-in-water emulsions

Accurately weighing phase A, stirring, mixing, heating to 80-85 deg.C for dissolving, heating phase B to 80-85 deg.C for dissolving completely, adding phase B into phase A, homogenizing at 3000rpm for 2-5min, stirring, cooling to 65 deg.C, adding phase C, stirring, cooling to 45 deg.C, adding antioxidant composition, stirring, adding phase E, stirring, cooling to room temperature, testing, and discharging.

Application example 19

Water-in-oil emulsions

Accurately weighing phase A, stirring, mixing uniformly, heating to 80-85 ℃, dissolving uniformly, cooling to 50 ℃, mixing uniformly at room temperature for phase B, slowly adding phase A into phase B while stirring, after phase A is completely added, homogenizing at 3000 plus 5000rpm for 2-5min, stirring, cooling to 35 ℃, adding phase C, stirring uniformly, adding phase D, stirring uniformly, cooling to room temperature, detecting and discharging qualified products.

The foregoing is merely a preferred embodiment of the invention and is not intended to limit the scope of the invention, which is defined by the claims appended hereto, and any other technical entity or method that is encompassed by the claims as broadly defined herein, or equivalent variations thereof, is contemplated as being encompassed by the claims.

Claims

1. A stable synergistic antioxidant cosmetic composition is characterized by comprising the following raw material components in percentage by weight based on the total weight of the composition:

2. the composition of claim 1, wherein the composition comprises the following raw material components, based on the total weight of the composition:

3. the composition of claim 1 or 2, wherein the raw material components of the composition are tocopherol, rosemary leaf extract, dimethylmethoxychromanol, and a solvent.

4. The composition of claim 1, wherein the solvent is selected from one or more of the following: ethanol, polyethylene glycol-8, 1, 3-butanediol and ethoxydiglycol.

5. The composition of claim 1, wherein the composition is a light yellow to brown homogeneous liquid.

6. A process for the preparation of a composition according to any one of claims 1 to 5, characterized in that it comprises the steps of: mixing tocopherol, rosemary leaf extract, dimethylmethoxychromanol and a solvent to obtain a composition according to any one of claims 1 to 5.

7. Use of a composition according to any of claims 1 to 5 for the preparation of a skin product.

8. A dermatological product comprising a composition according to any one of claims 1 to 5 and a cosmetically acceptable carrier.

9. A method of preparing a dermatological product of claim 8, comprising the steps of: mixing the composition according to any one of claims 1 to 5 and a cosmetically acceptable carrier to obtain a dermatological product according to claim 8.