KR101667765B1 - Nano-particle composition of skin whitening with improved skin penetration rate - Google Patents
Nano-particle composition of skin whitening with improved skin penetration rate Download PDFInfo
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- KR101667765B1 KR101667765B1 KR1020150128032A KR20150128032A KR101667765B1 KR 101667765 B1 KR101667765 B1 KR 101667765B1 KR 1020150128032 A KR1020150128032 A KR 1020150128032A KR 20150128032 A KR20150128032 A KR 20150128032A KR 101667765 B1 KR101667765 B1 KR 101667765B1
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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
- A61K8/36—Carboxylic acids; Salts or anhydrides thereof
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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
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
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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
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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
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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
- A61K8/36—Carboxylic acids; Salts or anhydrides thereof
- A61K8/361—Carboxylic acids having more than seven carbon atoms in an unbroken chain; Salts or anhydrides thereof
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- 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
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- 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
- A61K2800/41—Particular ingredients further characterized by their size
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- 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
- A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
Abstract
Description
The present invention relates to a whitening nanoparticle composition having a skin whitening effect, and more particularly to a whitening nanoparticle composition having improved light stability and skin permeability.
The skin color of a person is determined by the amount of melanin, carotene, and hemoglobin, among which melanin is the most crucial factor. Melanin is a pigment of blackish brown granules that protects proteins and genes by blocking ultraviolet rays from the skin. The skin is divided into epidermis of 50 ~ 100 ㎛ thickness and dermis of 2 ~ 3mm thickness directly below. Epidermis is divided into stratum corneum, granular layer, superficial layer and basal layer in order from the surface. Melanocytes, In the basal layer at the bottom of. When the skin is stimulated by ultraviolet rays, tyrosinase oxidizes tyrosine in the melanocyte, oxidized tyrosine produces melanin, and the resulting melanin rises to the stratum corneum and skin appears black.
A high amount of melanin means that it has an effective countermeasure to protect the skin from physical or chemical toxicants. However, when the skin is excessively exposed to external stimuli such as ultraviolet rays, environmental pollution, or stress, melanin is accumulated in the skin surface layer, resulting in serious problems such as stain, freckles and aging , And aging of the skin is accelerated to cause skin cancer.
Skin beauty is one of the important aesthetic factors. Especially in Asia, white skin like white is prefered and it is used as an important criterion of beauty. Therefore, development of skin whitening agent . Skin whitening agents are used to destroy melanin, inhibit enzymes involved in the formation of melanin, inhibit the production of melanin, or both, thereby brightening skin tone and reducing cosmetic problems due to melanin deposition.
In the field of cosmetics, resorcinol derivatives have been known to have excellent whitening efficacy through tyrosinase inhibition and have been used as an active ingredient in skin lightening agents. Among the resorcinol derivatives, phenylethyl resorcinol has been known to exert an excellent effect in skin whitening. However, phenylethylresorcinol is weak to light and easily denatured, resulting in poor stability in production of the product.
Emulsions are the most commonly used formulation systems in the cosmetics industry, in which the oil phase and water phase are uniformly dispersed using emulsifying technology. Emulsions are thermodynamically unstable, and research and development on techniques for increasing the stability of emulsions is continuing. The physiochemical properties of the emulsion are influenced by factors such as the type of surfactant used as an emulsifier, the external and internal aspect, the emulsion type, the thickening agent, the particle size, etc. and stabilize the active ingredient contained in the cosmetic composition prepared by the emulsion formulation And the selection of these factors in manufacturing is important to further improve skin absorbency.
The present invention aims to provide a composition for skin whitening which contains phenylethylresorcinol and is excellent in light stability and skin permeability.
It is another object of the present invention to provide a method for producing a composition for skin whitening.
According to one aspect of the present invention, there is provided a skin whitening nanoparticle composition comprising phenylethyl resorcinol, polyglyceryl-3 methyl glucose distearate, glyceryl stearate, a medium chain fatty acid, water and a lipid compound, Wherein the lipid compound is a fatty acid or a fatty alcohol having 16 to 22 carbon atoms.
In addition, the fatty acid may include at least one selected from the group consisting of stearic acid and palmitic acid.
In addition, the fatty alcohol may include at least one selected from the group consisting of cetearyl alcohol, cetyl alcohol, behenyl alcohol and stearyl alcohol.
The average particle size of the particles may be 200 to 300 nm and the polydispersity may be 0.05 to 0.25.
Also, the skin permeation amount within 12 hours may be 2 to 10 ug.
The average particle diameter change ratio (d 14 / d 0 ) of the particles may be 1 to 1.06.
According to another aspect of the present invention, there is provided a method for producing a polyglyceryl-3-methylglucosyl disestearate, comprising: a first step of heating phenylethylresorcinol, polyglyceryl-3 methyl glucose distearate, glyceryl stearate, a heavy chain fatty acid, water and a lipid compound at 70 to 95 ° C respectively; A second step of mixing and dissolving each raw material heated in the first step and emulsifying the raw materials in a primary step; And a third step of emulsifying at a high pressure of 900 to 1200 bar at a high pressure, wherein the lipid compound is a fatty acid or a fatty alcohol having 16 to 22 carbon atoms, A method of making a nanoparticle composition is provided.
The skin whitening nanoparticle composition according to one aspect of the present invention has excellent whitening efficacy, stability and skin permeability, and is therefore suitable for use as a cosmetic for skin whitening.
The nanoparticle composition for skin whitening according to one aspect of the present invention has a small and uniform nanoparticle size and excellent stability against precipitation or creaming phenomenon.
The nanoparticle composition for skin whitening according to one aspect of the present invention can reduce the manufacturing cost by improving the stability in the production of the product because the whitening component maintains its activity even when it is exposed to daylight or fluorescence for a long time due to reduced light denaturation.
FIG. 1 shows the results of particle size analysis of the skin whitening nanoparticle composition of the present invention,
FIG. 2 shows the skin permeability measurement result of the skin whitening nanoparticle composition of the present invention.
The present invention relates to a skin whitening nanoparticle composition comprising phenylethyl resorcinol, polyglyceryl-3 methyl glucose distearate, glyceryl stearate, a medium chain fatty acid, water and a lipid compound, wherein the lipid compound has a carbon number of 16 To 22 < / RTI > fatty acids or fatty alcohols.
Hereinafter, the present invention will be described in more detail.
The skin whitening nanoparticle composition of the present invention includes phenylethyl resorcinol. The phenylethyl resorcinol is a phenolic compound and exhibits a skin whitening effect by reducing the melanin pigment in the skin surface layer. The composition of the present invention can exhibit a skin whitening effect by containing phenylethylresorcinol as an active ingredient.
The content of phenylethyl resorcinol is not particularly limited and may be in the range of 1 to 10 wt% based on 100 wt% of the total composition. When phenylethyl resorcinol is contained in an amount of less than 1 wt%, the composition of the present invention hardly exhibits a whitening effect, and when it is contained in an amount of more than 10 wt%, the manufacturing cost may increase.
The skin whitening nanoparticle composition of the present invention comprises polyglyceryl-3 methyl glucose distearate. The polyglyceryl-3 methyl glucose distearate serves as an emulsifier to emulsify the composition. The composition of the present invention contains polyglyceryl-3 methyl glucose distearate as an emulsifying agent, so that stability can be improved. This can reduce not only the denaturation of the composition but also the removal of the phenylethylresinol component in the composition applied to the skin from the skin due to moisture such as perspiration.
The content of the polyglyceryl-3 methyl glucose distearate is not particularly limited and may be in the range of 1 to 10 wt% based on 100 wt% of the total composition. When polyglyceryl-3 methyl glucose distearate is contained in an amount of less than 1 wt%, the composition of the present invention may be difficult to emulsify and stability may be lowered. When the content of polyglyceryl-3 methyl glucose distearate is more than 10 wt% And the skin permeability of the composition may be lowered.
The skin whitening nanoparticle composition of the present invention comprises glyceryl stearate. The glyceryl stearate acts as a lipophilic auxiliary emulsifier and serves to emulsify the composition. In addition, the stability of the composition can be improved. In addition, when applied to the skin, an oil film can be formed to reduce the dryness of the skin and improve the skin permeation of the phenylethylresinol component.
The content of the glyceryl stearate is not particularly limited and may be in the range of 0.5 to 10 wt% based on 100 wt% of the total composition. In the present invention, it is preferable that the weight ratio of glyceryl stearate to polyglyceryl-3-methyl glucose distearate is 1: 2 to 3. When the composition of the present invention contains glyceryl stearate and polyglyceryl-3 methyl glucose distearate in a weight ratio of 1: 2 to 3, the stability and skin permeability of the composition can be maximized.
The skin whitening nanoparticle composition of the present invention comprises medium chain triglycerides. The heavy chain fatty acid forms an oil phase in the composition and has a short carbon length to reduce the stickiness of the composition and can be rapidly absorbed to the skin to promote skin permeation of the composition.
The content of the heavy chain fatty acid is not particularly limited and may be in the range of 1 to 10 wt% based on 100 wt% of the total composition. When the content of the heavy chain fatty acid is less than 1 wt%, it is difficult to form an oil phase, thereby reducing the stability of the emulsion composition. When the content is more than 10 wt%, the specific gravity of the oil phase is increased, And the manufacturing cost may increase.
The skin whitening nanoparticle composition of the present invention comprises water. The water forms a water phase in the composition. The content of the water is not particularly limited and may be included in an amount of 50 to 95 wt% based on 100 wt% of the total composition. Preferably, it is contained in an amount of 80 to 90 wt%.
The skin whitening nanoparticle composition of the present invention comprises at least one lipid compound selected from the group consisting of fatty acids having 16 to 22 carbon atoms and fatty alcohols. The fatty acid may include at least one selected from the group consisting of stearic acid and palmitic acid, for example. Examples of the fatty alcohol include at least one selected from the group consisting of cetearyl alcohol, cetyl alcohol, behenyl alcohol and stearyl alcohol. The lipid compounds can enhance the light stability of phenylethyl resorcinol and promote skin absorption. If the number of carbon atoms of the lipid compound is less than 16, the photostability of the composition may deteriorate. If the number of carbon atoms is more than 22, the viscosity of the composition may increase, and the skin absorption of stearyl alcohol may decrease.
The content of the at least one lipid compound selected from the group consisting of fatty acids having 16 to 22 carbon atoms and fatty alcohols is not particularly limited and may be 1 to 10 wt% based on 100 wt% of the total composition. When the amount of the lipid compound is less than 1 wt%, the effect of improving the photostability of the composition is hardly exhibited. If the amount of the lipid compound is more than 10 wt%, the stability of the emulsion composition may be reduced.
The skin whitening nanoparticle composition of the present invention may be in the form of an emulsion in which the oil phase and water phase are dispersed. Wherein said oil phase comprises at least one lipid compound selected from the group consisting of phenylethyl resorcinol, polyglyceryl-3 methyl glucose distearate, glyceryl stearate, medium chain fatty acids and fatty acids having from 16 to 22 carbon atoms and fatty alcohols . The water phase may comprise water. The weight ratio of the oil phase to the water phase is preferably 1: 4 to 9. The stability of the composition of the present invention can be maximized when the weight ratio of oily phase to water phase falls within the above range. More preferably, the weight ratio of the oil phase to the water phase is 1: 6 to 7.
The particles included in the skin whitening nanoparticle composition of the present invention may have an average particle diameter ranging from 200 to 300 nm. Preferably, it is in the range of 200 to 250 nm. In order to improve the skin permeability of the composition, it is preferable that the average particle diameter of the particles is small. If the average particle size of the particles exceeds 300 nm, the skin permeability may be lowered. The polydispersity of the compositions of the present invention may range from 0.05 to 0.25. The polydispersity means a value measured by a cumulative method using a particle size analyzer. The composition of the present invention can maximize the stability and skin permeability of the composition when the average particle size and polydispersity of the particles contained in the composition fall within the above range.
The skin whitening nanoparticle composition of the present invention can satisfy the physical properties of 2 to 10 ug in the skin permeation amount within 12 hours. The amount of the skin permeation within 12 hours was measured using a Franz Cell Diffusion system (0.2 ml of the skin whitening nanoparticle composition of the present invention as a sample) on the donor skin surface, and after 12 hours, 0.3 ml was taken and quantitatively measured. If the skin permeation amount is less than 2 ug within 12 hours, it may be difficult to absorb the skin of the phenylethylresinol component and the whitening effect may be deteriorated. In this respect, the skin permeation amount within 12 hours is preferably 5 to 10 ug.
The skin-whitening nanoparticle composition of the present invention can satisfy physical properties such that the average particle diameter change ratio (d 14 / d 0 ) of the nanoparticles is 1 to 1.06. In the present invention, the average particle size change ratio is a mean particle diameter value (d 14 ) of the particles of the composition exposed for 14 days under a light condition of 1,000 lux under the same conditions a value obtained by dividing by zero) (the mean d 14 / d 0). When the particles of the composition of the present invention are exposed to sunlight or fluorescence, the average particle size increases, and when the average particle size of the particles of the composition increases, the stability of the composition may be reduced. When the average particle diameter change ratio is more than 1.06, the stability of the composition is lowered and the phenylethyl resorcinol is denatured by browning, thereby reducing the whitening effect.
The present invention also provides a method for producing the skin whitening nanoparticle composition.
As the method for producing the nanoparticle composition, a method of manufacturing a nano emulsion known in the art can be used. For example, a selected manufacturing method of highenergy methods or low-energy methods can be used. The high-energy method may be performed using high-shear stirring, high-pressure homogenizers, or the like.
According to one embodiment of the present invention, firstly, a mixture of phenylethylresorcinol, polyglyceryl-3-methyl glucose distearate, glyceryl stearate, a medium-chain fatty acid, water, 22 fatty acids and at least one lipid compound selected from the group consisting of fatty alcohols. The heating temperature is preferably 70 to 95 ° C. More preferably, it is 70 to 80 캜. The fatty acid may include at least one selected from the group consisting of stearic acid and palmitic acid, for example. Examples of the fatty alcohol include at least one selected from the group consisting of cetearyl alcohol, cetyl alcohol, behenyl alcohol and stearyl alcohol.
Next, each heated raw material is mixed and dissolved and primary emulsified. The primary emulsification can be carried out by adding water and then adding a component which forms an oil phase while stirring at a temperature of 70 to 95 ° C. If necessary, the water can be added by dividing the water into the water, then adding the water-forming component first, and then adding the water again.
Next, in order to make the particle size of the emulsion to be produced smaller, the primary emulsion is secondarily emulsified at a high pressure of 900 to 1200 bar. This can be carried out using a high-pressure emulsifier (microfluidizer), and can be carried out in two or more divided portions.
The production method according to one embodiment of the present invention can further improve the stability of the emulsion to be produced by dividing the emulsion into two or more stages.
Hereinafter, the present invention will be described in more detail with reference to the following examples and comparative examples in order to facilitate understanding of the present invention. It will be apparent to those skilled in the art that these embodiments are illustrative of the present invention and are not intended to limit the scope of the appended claims and that various changes and modifications may be made to the embodiments within the scope and spirit of the invention , And it is natural that such variations and modifications fall within the scope of the appended claims.
Example
≪ Preparation of Skin Whitening Nanoparticle Composition >
At least one lipid compound selected from the group consisting of phenylethyl resorcinol, Tegocare 450, glyceryl stearate, medium chain fatty acid oil, water and fatty acids having 16 to 22 carbon atoms and fatty alcohols, are each heated at a temperature of 75 ° C. Next, they were mixed and emulsified using a mixer (Homo-Mixer) in the composition shown in Table 1 below. When mixing, water was added first, then other materials were added.
(wt%)
450
(wt%)
(wt%)
(wt%)
(wt%)
(wt%)
Next, the nanoparticle emulsion composition was prepared by emulsification three times under a pressure of 1000 bar by using a high-pressure emulsifier (Microfluidizer). The prepared nanoparticle emulsion composition was subjected to particle size analysis by a cumulant method using a particle size analyzer, and the results are shown in FIG. 1 and Table 2. (A), (B), (C), (D), (E), and (F) 6.
Referring to FIGS. 1 and 2, it can be seen that the average particle diameter of the prepared nanoparticle emulsion composition is 200 to 300 nm and the polydispersity is 0.05 to 0.25.
≪ Confirmation of skin permeability of skin-whitening nanoparticle composition >
The skin permeability of the composition of the Example was confirmed. As a comparative example, a composition prepared by adding water to stearic acid in Example 1 was prepared and used. The skin permeability of each composition was determined using a Franz Cell Diffusion system using the samples of Examples 1, 3, 5 and Comparative Examples as a sample. The skin removed from the cervical dislocated rats (ICR outbred albino mice, 12 weeks, 50 g, female) was used. The skin was removed from the rat's stomach and subcutaneous fat and tissues were removed to prevent skin damage. The Franz cell diffusion system was prepared by securing the skin between the donor and the receptor phase with the stratum corneum facing up. The 5 ml receptor phase was administered and the temperature was maintained at 37 +/- 0.5 [deg.] C using a constant temperature bath. The stirring speed was 150 rpm for 2 hours. 0.3 ml of the receptor phase was collected at 0, 1, 2, 4, 5, 8, 10 and 12 hours after adding 0,2 ml of each sample to the surface of the hard surface of the donor. The collected receptor phase was vortexed for 2 minutes, centrifuged and quantitatively analyzed. The results are shown in FIG. 2 below.
Referring to FIG. 2, Examples 1, 3, and 5 have superior skin permeability as compared with Comparative Examples. In the case of Examples 1, 3 and 5, the average particle diameter of the composition was in the range of 200 to 250 nm, and the skin permeability was remarkably superior to that of Comparative Example. The composition of the present invention has excellent skin permeability, so that the active ingredient contained in the composition can be quickly and effectively absorbed into the skin.
<Confirmation of Stability of Skin Whitening Nanoparticle Composition>
The stability for Examples 1 to 6 was evaluated by evaluating stability over time and light stability. The aging stability was confirmed by measuring the average particle size change ratio. The average particle size change ratio (d 0 ) of the particles of the composition was measured and the average particle diameter (d 14 ) of the particles was measured after the composition was exposed under the light condition of 1,000 lux for 14 days. (D 14 / d 0 ) obtained by dividing by the average particle diameter value (d 0 ) of the particles measured before exposure to light. The light stability was determined by observing the discoloration of the composition visually, and when the discoloration did not occur even after exposure to light, the discoloration was classified as stable, and when the discoloration occurred, the discoloration was classified as unstable. The results of confirming the aging stability and the light stability are shown in Table 3 below. In Table 3, the unit of the average particle diameter is nm, and the 0th day means the value measured before exposure to light.
Referring to Table 3 above, all of the examples showed excellent long-time stability and light stability. All the examples satisfying the condition that the average particle diameter change ratio (d 14 / d 0 ) was in the range of 1 to 1.06 were found to maintain excellent performance without denaturation of the active ingredient up to 14 days even when exposed to light condition. In Examples 4 and 6, the light stability was somewhat lowered due to the change in the size of the nanoparticles with the average particle diameter of the nanoparticles contained in the composition exceeding 300 nm on the 21st day. However, in the examples including the palmitic acid as the lipid compound 2, excellent optical stability was exhibited even when the average particle diameter of the nanoparticles exceeded 300 nm. As a result, it can be confirmed that the composition of the present invention satisfying the conditions that the average particle diameter is 200 to 300 nm and the average particle diameter change ratio is 1 to 1.06 even when exposed to the light condition, has excellent stability.
Claims (7)
Wherein the lipid compound is a fatty acid or fatty alcohol having 16 to 22 carbon atoms,
Wherein the average particle size change ratio (d14 / d0) of the particles is 1 to 1.06.
A second step of mixing and dissolving each raw material heated in the first step and emulsifying the raw materials in a primary step; And
And a third step of emulsifying the nanoparticles at a high pressure of 900 to 1200 bar at a high pressure, the method comprising:
Wherein the lipid compound is a fatty acid or a fatty alcohol having 16 to 22 carbon atoms, and has improved light stability and skin permeability.
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
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CN106377435A (en) * | 2016-10-26 | 2017-02-08 | 德之馨(上海)有限公司 | Emulsion type skin whitening formula based on 4-(1-phenethyl)-1,3-benzenediol alcohol solute |
CN106377436A (en) * | 2016-10-26 | 2017-02-08 | 德之馨(上海)有限公司 | Water-soluble whitening formula based on 4-(1-phenethyl)-1,3-hydroquinone |
CN106420376A (en) * | 2016-10-26 | 2017-02-22 | 德之馨(上海)有限公司 | Emulsification type whitening formula based on 4-(1-phenethyl)-1,3-benzenediol oil solute |
CN108743430A (en) * | 2018-06-28 | 2018-11-06 | 武汉百思凯瑞生物科技有限公司 | A kind of total conveying nano-composition of Symwhite-337 and its preparation method and application |
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KR101362619B1 (en) * | 2008-02-20 | 2014-02-13 | 이엘씨 매니지먼트 엘엘씨 | Topical compositions and methods for whitening skin |
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JP2842607B2 (en) | 1989-03-13 | 1999-01-06 | 株式会社日立製作所 | Echo canceller, communication device including the same, and signal processing method |
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CN106377435A (en) * | 2016-10-26 | 2017-02-08 | 德之馨(上海)有限公司 | Emulsion type skin whitening formula based on 4-(1-phenethyl)-1,3-benzenediol alcohol solute |
CN106377436A (en) * | 2016-10-26 | 2017-02-08 | 德之馨(上海)有限公司 | Water-soluble whitening formula based on 4-(1-phenethyl)-1,3-hydroquinone |
CN106420376A (en) * | 2016-10-26 | 2017-02-22 | 德之馨(上海)有限公司 | Emulsification type whitening formula based on 4-(1-phenethyl)-1,3-benzenediol oil solute |
CN108743430A (en) * | 2018-06-28 | 2018-11-06 | 武汉百思凯瑞生物科技有限公司 | A kind of total conveying nano-composition of Symwhite-337 and its preparation method and application |
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