CN115120515B - Whitening and freckle-removing composition and preparation method thereof - Google Patents
Whitening and freckle-removing composition and preparation method thereof Download PDFInfo
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- CN115120515B CN115120515B CN202210943796.9A CN202210943796A CN115120515B CN 115120515 B CN115120515 B CN 115120515B CN 202210943796 A CN202210943796 A CN 202210943796A CN 115120515 B CN115120515 B CN 115120515B
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- whitening
- freckle
- cyclodextrin
- removing composition
- phenethyl resorcinol
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
- A61K8/347—Phenols
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/73—Polysaccharides
- A61K8/738—Cyclodextrins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/56—Compounds, absorbed onto or entrapped into a solid carrier, e.g. encapsulated perfumes, inclusion compounds, sustained release forms
Abstract
The invention discloses a whitening and freckle-removing composition and a preparation method thereof. The invention firstly adopts a high-pressure homogenization process to prepare an aqueous solution of the phenethyl resorcinol cyclodextrin inclusion compound, then disodium edentate, sodium bisulphite and a pH stabilizer are added, the stability of the phenethyl resorcinol cyclodextrin inclusion compound in liquid and semisolid products is improved, and the concentration of the phenethyl resorcinol in the prepared composition is improved to 2%. The composition can be directly used as cosmetics or can be used as cosmetic raw materials for preparing cosmetics such as cream, emulsion, essence and the like after being diluted.
Description
Technical Field
The invention relates to a whitening and freckle-removing composition and a preparation method thereof, and belongs to the technical field of cosmetics.
Background
Phenethyl resorcinol (Phenylethyl Resorcinol, hereinafter referred to as "PR") is a novel and efficient whitening active substance, and has the chemical name of 4- (1-phenethyl) -1, 3-benzenediol, and the structural formula shown below.
PR structure is similar to tyrosine, and has bisphenol structure similar to hydroquinone, and is slightly soluble in water at normal temperature, easily soluble in propylene glycol and polar oil, and unstable under illumination. PR is one of tyrosinase inhibitors with highest whitening activity reported at present, and can effectively reduce melanin generation, improve uneven skin color and reduce skin coloration caused by ultraviolet irradiation on skin by inhibiting the activities of tyrosinase monophenolase and diphenolase; meanwhile, PR has strong antioxidation capability, is favorable for melanin resolution, and has good whitening and freckle removing effects. PR was officially approved by the State food and drug administration (CFDA) as a raw material for cosmetics in 2012, and the recommended use amount in cosmetics was 0.1 to 0.5%. Their extremely poor water solubility and photostability limit their use in the cosmetic field.
Cyclodextrins are a generic term for a series of cyclic oligosaccharides produced by amylose by the action of cyclodextrin glucosyltransferase enzymes produced by Bacillus and generally contain 6 to 12D-glucopyranose units. Common natural cyclodextrins are α, β and γ -cyclodextrins. The beta-cyclodextrin has a cylindrical three-dimensional structure, the outer wall has strong hydrophilicity, the inner wall has strong hydrophobicity, the hydrophobic cavity can be used for clathrating guest molecules to form an inclusion compound, but the inside of the beta-cyclodextrin is an annular full hydrogen bond band, and the beta-cyclodextrin has quite rigidity and poor water solubility. Compared with beta-cyclodextrin and other cyclodextrins, the hydroxypropyl is introduced to break the intramolecular cyclic hydrogen bond of the beta-cyclodextrin, so that the hydroxypropyl-beta-cyclodextrin has better water solubility and biocompatibility while maintaining the cyclodextrin cavity, and is one of cyclodextrin derivatives which are most deeply researched and widely used at present.
The hydroxypropyl-beta-cyclodextrin is white or white amorphous or crystalline powder, odorless, slightly sweet in taste and strong in hygroscopicity; is very soluble in water, methanol and ethanol, and is almost insoluble in acetone and chloroform. The hydroxypropyl-beta-cyclodextrin has a special three-dimensional cyclic structure of internal hydrophobic and external hydrophilic, can be used for clathrating insoluble substances into a hydrophobic cavity of the hydroxypropyl-beta-cyclodextrin in a non-covalent bond form, and forms clathrates of 1:1 and 2:1 with insoluble substance molecules or forms oligomers, so that the water solubility of the insoluble substances can be improved, and the stability of the insoluble substances can be improved after the formed clathrates; meanwhile, because the inclusion reaction is a dynamic process, the guest molecules are continuously included by cyclodextrin, and meanwhile, the inclusion is continuously released, so that the influence on the release of insoluble substances is small, and the bioavailability of the insoluble substances can be improved. In the aspect of safety, the irritation experiments of the skin and eyes of the experimental rabbits show that the hydroxypropyl-beta-cyclodextrin has no irritation to the skin and eyes of the rabbits; and the sensitivity experiment shows that the hydroxypropyl-beta-cyclodextrin has no sensitization to the skin of the experimental pig. The hydroxypropyl-beta-cyclodextrin can be used as stabilizer, emulsifier, deodorant, etc. in cosmetics, and can reduce irritation of organic molecules in cosmetics to skin mucosa tissue, enhance stability of effective components, and prevent volatilization and oxidation of nutritional components.
CN 103536454a discloses a preparation method of phenethyl resorcinol hydroxypropyl-beta-cyclodextrin inclusion compound, which adopts organic solvents such as tertiary butanol, ethanol, methanol, 1, 2-propylene glycol and the like to dissolve phenethyl resorcinol and hydroxypropyl-beta-cyclodextrin, and prepares a powder inclusion compound with good stability and water solubility after removing the organic solvents by vacuum drying. The method has the defect that a large amount of organic solvent is required to be used, so that the environment is polluted. Furthermore, although the technology improves the stability of the solid powder inclusion compound, the stability of the solid powder inclusion compound in aqueous solution to light and heat is still poor. Therefore, how to improve the stability of phenethyl resorcinol hydroxypropyl-beta-cyclodextrin inclusion compound in the preparations such as cream, water, milk and the like commonly used in cosmetics is still a technical problem to be solved at present.
Disclosure of Invention
Aiming at the problems, the invention provides a whitening and freckle-removing composition containing phenethyl resorcinol hydroxypropyl-beta-cyclodextrin inclusion compound and a preparation method thereof. The preparation method of the invention firstly adopts a high-pressure homogenization process to prepare the phenethyl resorcinol cyclodextrin inclusion compound aqueous solution, and then adds chelating agent edetate disodium, antioxidant sodium bisulphite, pH stabilizer and the like, thereby improving the stability of the phenethyl resorcinol cyclodextrin inclusion compound in liquid and semisolid products, and more importantly, the preparation method of the invention avoids the use of organic solvents, is a green and environment-friendly preparation process, and is beneficial to industrial production. The skin care quality with the whitening and freckle removing effects prepared by the composition is stable, and the application of the phenethyl resorcinol cyclodextrin inclusion compound in the field of cosmetics is enlarged.
The technical scheme of the invention is as follows:
a whitening and freckle-removing composition is characterized by being prepared by the following steps:
a) Adding phenethyl resorcinol and cyclodextrin into water, mixing, and homogenizing under high pressure;
b) Adding disodium edentate and sodium bisulphite;
c) Adding a pH stabilizer;
wherein, the concentration of the phenethyl resorcinol is 0.1-2%, the concentration of the cyclodextrin is 0.6-15%, the concentration of the preferred phenethyl resorcinol is 0.5-2%, the concentration of the cyclodextrin is 3-15%, and the proportion of each component is mass ratio.
Further, after the phenethyl resorcinol and the cyclodextrin are mixed with water, high-pressure homogenization is performed under a pressure of 400-1500 bar, and the high-pressure homogenization pressure can be 500-800 bar or 1200-1400 bar. The method can prolong the homogenizing time for repeated cyclic homogenizing under the condition of lower pressure, and can also adopt high pressure condition to shorten the homogenizing time and reduce the cyclic homogenizing times. Alternatively, a high pressure homogenization at a lower pressure may be employed first, followed by a high pressure homogenization at a higher pressure. For example, the high-pressure homogenization is carried out at a pressure of 500 to 800bar, then the high-pressure homogenization is carried out at a pressure of 700 to 800bar, and finally the high-pressure homogenization is carried out at a pressure of 1200 to 1400bar.
The uniform, clear and transparent phenethyl resorcinol cyclodextrin inclusion compound solution is prepared by the high-pressure homogenization method.
Further, the cyclodextrin is hydroxypropyl-beta-cyclodextrin.
The concentration of the edetate disodium is 0.01-0.2 percent, preferably 0.05-0.1 percent.
The concentration of the sodium bisulphite is 0.05-0.5%, preferably 0.2-0.5%.
The pH stabilizer is selected from citric acid, acetic acid and/or phosphate, preferably the pH stabilizer is a citric acid-sodium citrate buffer system.
Furthermore, after the pH stabilizer is added into the composition, a humectant, a thickener and a preservative which are commonly used in cosmetics can be added.
The moisturizers and thickeners commonly used in cosmetics include, but are not limited to, propylene glycol, glycerin, butylene glycol, hypromellose, trehalose, gelatin, xanthan gum, gellan gum, alginic acid and its salts, hyaluronic acid and its salts, polyglutamic acid and its salts, and the like. Wherein alginic acid and its salts, hyaluronic acid and its salts and polyglutamic acid and its salts are selected from soluble metal salts of alginic acid, hyaluronic acid and polyglutamic acid, such as sodium salt, potassium salt, calcium salt and zinc salt. Including but not limited to sodium alginate, hyaluronic acid, sodium hyaluronate, zinc hyaluronate, potassium hyaluronate, calcium hyaluronate, polyglutamic acid, sodium polyglutamate, and the like.
The preservatives commonly used in cosmetics include, but are not limited to, phenethyl alcohol, p-methylbenzyl alcohol, phenoxyethanol, benzalkonium chloride, benzalkonium bromide, methyl paraben, ethyl paraben, propyl paraben, 1, 2-hexanediol, 1, 2-pentanediol, methylpropanediol, ethylhexyl glycerol, and octanediol, etc.
The phenethyl resorcinol is slightly soluble in water, the concentration of a saturated aqueous solution is 0.12%, the stability is poor, and an ideal whitening and freckle removing effect cannot be obtained when the phenethyl resorcinol is used in cosmetics. The invention utilizes the special three-dimensional cyclic structure of 'inner hydrophobic and outer hydrophilic' of hydroxypropyl-beta-cyclodextrin, adopts a high-pressure homogenization process, realizes the inclusion of the hydrophobic cavity of the hydroxypropyl-beta-cyclodextrin on the phenethyl resorcinol in aqueous solution by full dispersion, the average inclusion rate of the hydroxyethyl resorcinol hydroxypropyl-beta-cyclodextrin inclusion compound in the prepared composition can reach 96.5%, and the concentration of the phenethyl resorcinol in the composition is increased to 2%. Experiments prove that the composition can obtain uniform and transparent phenethyl resorcinol hydroxypropyl-beta-cyclodextrin inclusion compound solution by adopting a high-pressure homogenization process, obviously improves the concentration of the phenethyl resorcinol in the solution, and can improve the stability of the phenethyl resorcinol in a solution system: under the conditions of high-temperature heating and strong light irradiation, the saturated aqueous solution of the phenethyl resorcinol has dark yellow turbidity, the phenethyl resorcinol content is rapidly reduced, the composition of the invention is still kept as clear liquid, the phenethyl resorcinol content is basically unchanged (see the stability comparison test research of example 3 for details), the shelf life of the product can be prolonged in practical application, and the application of the product in the cosmetic field is facilitated.
The composition can be directly used as cosmetics or can be used as cosmetic raw materials for preparing cosmetics such as cream, emulsion, essence and the like after being diluted. The preparation method of the composition does not need to use an organic solvent, reduces the cost, is environment-friendly and is beneficial to the industrial production of products. The composition of the invention increases the concentration of the phenethyl resorcinol in the solution to be more than the effective concentration, and can keep stable quality for a long time, so that the composition can better exert the whitening and freckle removing effects and prolong the shelf life of the product, thereby having wider application prospect in the field of cosmetics.
Detailed Description
The present invention will be described in further detail with reference to examples, but the scope of the present invention is not limited to the examples.
Example 1
The whitening and freckle-removing composition is prepared by weighing phenethyl resorcinol and hydroxypropyl-beta-cyclodextrin according to a table 1, adding 800ml of purified water, mixing and stirring to obtain a suspension, and carrying out high-pressure circulation and homogenization for more than 5 times under the pressure of 500-800 bar until the suspension is completely dissolved to obtain a uniform and transparent solution; sequentially adding disodium edentate and sodium bisulphite, and stirring until the disodium edentate and the sodium bisulphite are completely dissolved; adding a pH stabilizer, and stirring until the pH stabilizer is completely dissolved; finally adding preservative and stirring uniformly; adding purified water to 1000ml, and stirring uniformly; filtering with 0.45 μm filter membrane.
TABLE 1 ingredients and content (g) per 1000ml of the whitening and freckle-removing composition of the present invention
Example 2
The whitening and freckle-removing composition is prepared by weighing phenethyl resorcinol and hydroxypropyl-beta-cyclodextrin according to a table 2, adding 800ml of purified water, mixing and stirring to obtain a suspension, homogenizing for 1 time at a high pressure of 400-500 bar, homogenizing for 1 time at a high pressure of 700-800 bar, and homogenizing for more than 1 time at a high pressure of 1200-1400 bar until the suspension is completely dissolved to obtain a uniform, clear and transparent solution; sequentially adding disodium edentate and sodium bisulphite, and stirring until the disodium edentate and the sodium bisulphite are completely dissolved; adding the pH stabilizer, the humectant and the thickener, and stirring until the mixture is completely dissolved; finally adding preservative and stirring uniformly; adding purified water to 1000ml, and stirring uniformly; filtering with 0.45 μm filter membrane.
TABLE 2 ingredients and content (g) per 1000ml of the whitening and freckle-removing composition of the present invention
Experimental example: stability contrast test study
Sample preparation:
(1) The invention relates to a whitening and freckle-removing composition: prepared according to the formulations and preparation methods of 1-3 in example 1, 2-7 in example 2 and 2-9 in example 2.
(2) Control sample 1 (phenethyl resorcinol saturated aqueous solution): 2.5g of phenethyl resorcinol is taken, water is added to 950ml, after heating and stirring to dissolve as much as possible, the mixture is cooled to room temperature, citric acid buffer pair, 1, 2-pentanediol and ethylhexyl glycerol which are equal in mass to 1-3 in example 1 are added, water is added to 1000ml, and the mixture is filtered through a 0.45 mu m filter membrane to obtain the novel compound.
(3) Control sample 2 (phenethyl resorcinol hydroxypropyl-beta-cyclodextrin clathrate in water): 250g of phenethyl resorcinol hydroxypropyl-beta-cyclodextrin inclusion compound (phenethyl resorcinol content 1.92%) was prepared according to the disclosed vacuum drying method (CN 103536454A example 1), added with water to 950ml, stirred at room temperature for dissolution, added with citric acid buffer pair, 1, 2-pentanediol and ethylhexyl glycerol of the same mass as 1-3 in example 1, added with water to 1000ml, and filtered through a 0.45 μm filter membrane to obtain the final product.
The sample solutions were respectively filled in 5ml borosilicate glass ampoules at a concentration of 5ml per ampoule. Heating at 60deg.C and irradiating with light (5000 Lux, ultraviolet 90 uW/cm) 2 ) Under the condition, the sample is observed for 10 days, and HPLC [ Waters XBidge C is adopted 18 (4.6 mm. Times.150 mm,5 μm) column; mobile phase: methanol-0.1% phosphoric acid solution (65:35); detection waveAnd (3) length: 280nm; column temperature: 30 ℃; flow rate: 1.0ml/min; sample injection amount: 10 μl of]PR content was measured and the results of the measurement were compared with those shown in Table 3 below.
Table 3 results of the tests of examples and comparative examples
Note that: "-" means decrease and "+" means increase.
The test results show that the maximum content of the phenethyl resorcinol in the whitening and freckle-removing composition solution prepared by the invention can reach 20.01mg/ml, which is 16 times of that of the phenethyl resorcinol saturated aqueous solution, and the solubility of the phenethyl resorcinol in water can be obviously improved. The properties and the content of the composition samples prepared according to the embodiment of the invention are not obviously changed after the composition samples are inspected by high temperature and illumination for 10 days, which shows that the whitening and freckle removing composition solution has better stability to light and heat; and the properties of the control sample phenethyl resorcinol saturated aqueous solution and the phenethyl resorcinol hydroxypropyl-beta-cyclodextrin inclusion compound aqueous solution are obviously changed under the conditions of high temperature and illumination, and the content is obviously reduced. The result shows that the composition of the invention obviously improves the stability of the phenethyl resorcinol in the solution, can prolong the shelf life of the product in practical application, and is beneficial to the application of the composition in the field of cosmetics.
Claims (8)
1. A whitening and freckle-removing composition is characterized by being prepared by the following steps:
a) Adding phenethyl resorcinol and hydroxypropyl-beta-cyclodextrin into water, mixing, and homogenizing under high pressure of 400-1500 bar;
b) Adding disodium edentate and sodium bisulphite;
c) Adding a pH stabilizer;
wherein, the concentration of the phenethyl resorcinol is 0.1-2%, and the concentration of the cyclodextrin is 0.6-15%.
2. The whitening and freckle-removing composition according to claim 1, wherein the concentration of the phenethyl resorcinol is 0.5-2% and the concentration of the cyclodextrin is 3-15%.
3. The whitening and freckle-removing composition according to claim 1, wherein the concentration of the edetate disodium is 0.01-0.2%.
4. The whitening and freckle removing composition according to claim 1, wherein the concentration of the sodium bisulphite is 0.05-0.5%.
5. The whitening and freckle-removing composition of claim 1, wherein the pH stabilizer is selected from the group consisting of citric acid, acetic acid and/or phosphate.
6. The whitening and freckle removing composition according to claim 5, wherein the pH stabilizer is a citric acid-sodium citrate buffer system.
7. The whitening and freckle-removing composition according to any one of claims 1 to 6, wherein a humectant, a thickener and a preservative commonly used in cosmetics are further added after the pH stabilizer is added.
8. The use of the whitening and freckle-removing composition as claimed in claim 7 for preparing a whitening and freckle-removing cosmetic.
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| CN202210943796.9A CN115120515B (en) | 2022-08-08 | 2022-08-08 | Whitening and freckle-removing composition and preparation method thereof |
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| CN202210943796.9A CN115120515B (en) | 2022-08-08 | 2022-08-08 | Whitening and freckle-removing composition and preparation method thereof |
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| CN115120515B true CN115120515B (en) | 2023-10-17 |
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| CN115554180B (en) * | 2022-10-24 | 2023-09-22 | 陕西畅想制药有限公司 | 4-butylresorcinol supermolecule vesicle aggregate, preparation method thereof and cosmetic composition |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101053556A (en) * | 2006-04-14 | 2007-10-17 | 沈阳市万嘉生物技术研究所 | Water soluble coenzyme Q10 hydroxyl-beta-cyclodextrin inclusion compound and its preparation method |
| CN103536454A (en) * | 2013-10-30 | 2014-01-29 | 东南大学 | Phenylethyl resorcinol hydroxypropyl-beta-cyclodextrin inclusion and preparation method thereof |
| CN104306269A (en) * | 2014-11-04 | 2015-01-28 | 珀莱雅化妆品股份有限公司 | Preparation method of cyclodextrin inclusion compound liposome with whitening effect |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101053556A (en) * | 2006-04-14 | 2007-10-17 | 沈阳市万嘉生物技术研究所 | Water soluble coenzyme Q10 hydroxyl-beta-cyclodextrin inclusion compound and its preparation method |
| CN103536454A (en) * | 2013-10-30 | 2014-01-29 | 东南大学 | Phenylethyl resorcinol hydroxypropyl-beta-cyclodextrin inclusion and preparation method thereof |
| CN104306269A (en) * | 2014-11-04 | 2015-01-28 | 珀莱雅化妆品股份有限公司 | Preparation method of cyclodextrin inclusion compound liposome with whitening effect |
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