CN106726690B - Water-soluble salicylic acid microspheres and preparation method thereof - Google Patents
Water-soluble salicylic acid microspheres and preparation method thereof Download PDFInfo
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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
- A61K8/368—Carboxylic acids; Salts or anhydrides thereof with carboxyl groups directly bound to carbon atoms of aromatic rings
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- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/0241—Containing particulates characterized by their shape and/or structure
- A61K8/025—Explicitly spheroidal or spherical shape
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- A—HUMAN NECESSITIES
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- 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
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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
- A61K8/732—Starch; Amylose; Amylopectin; Derivatives 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
- A61K8/18—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
- A61K8/736—Chitin; Chitosan; Derivatives 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
- A61K8/18—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
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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
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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
- A61K2800/56—Compounds, absorbed onto or entrapped into a solid carrier, e.g. encapsulated perfumes, inclusion compounds, sustained release forms
Abstract
The invention discloses a water-soluble salicylic acid microsphere and a preparation method thereof. Adding cyclodextrin and salicylic acid into water with the mass ratio of 1:1.5-2.5 of cyclodextrin to 80-100 times of that of cyclodextrin, ultrasonically dispersing, and fully dissolving at 40-100 ℃ to obtain salicylic acid-cyclodextrin inclusion compound solution; respectively adding 0.5-1.0g of maltodextrin and 1.0-2.0g of amylopectin into 100g of water, fully dissolving at 60-100 ℃ to obtain a salicylic acid solution, then respectively adding 0.2-0.5g of chitosan and 0.5-1.0g of Arabic gum into the salicylic acid solution according to the amount of 0.2-0.5g of chitosan and 0.5-1.0g of Arabic gum into 100g of water, fully dissolving at 60-100 ℃ to obtain a final solution, and then spray-drying the final solution to obtain the water-soluble salicylic acid microspheres. The whitening acne-removing cream not only effectively exerts the whitening acne-removing effect of the salicylic acid, but also can increase the solubility of the salicylic acid in water, reduce the irritation of the salicylic acid in use and has strong stability.
Description
The technical field is as follows:
the invention belongs to the technical field of skin care products, and particularly relates to a water-soluble salicylic acid microsphere and a preparation method thereof.
Background art:
earlier, Salicylic Acid (SA) is produced by extraction from willow bark and has molecular structure C7H6O3. As a class of hormones, SA has important physiological roles in most plants, such as: promoting the ethylene biosynthesis, promoting the plant rooting, delaying the fruit after-ripening and aging, regulating the plant photoperiod, regulating the seed germination, inducing the blooming and stomata closure, improving the disease resistance, etc. The salicylic acid has excellent capability of removing cutin and cleaning pores, can lighten pigmented spots, shrink pores, remove fine wrinkles, improve aging and acne removal caused by sunshine and the like, and becomes a pet of a maintenance product. In addition, SA is used as a preservative in cosmetics, mainly in leave-on products and rinse-off skin care and hair products. (2007 edition) in the standards of cosmetics hygiene, the limit of SA in the resident product is 2.0%; the limited amount of SA in rinse-off skin and hair care products is 3.0%.
Salicylic acid can dissolve the substance (pigment) between horny layers to cause the horny layer to fall off, so that it can remove the horny layer accumulated too thick and promote metabolism. It can remove cutin and restore skin smoothness; pores are reduced, and the situation of pore blockage is improved; preventing acne, reducing abnormal falling of hair follicle wall, and whitening skin.
However, salicylic acid alone is apt to irritate the skin and mucous membranes, and to react with proteins in body tissues, and has problems such as poor solubility and difficulty in addition, thus limiting its wide use in cosmetics. The salicylic acid microspheres are prepared by using methods such as composite doping, electrostatic grafting modification and the like, so that the salicylic acid microspheres have good water solubility and low irritation in application, and have important significance for expanding the application range of the salicylic acid microspheres.
Cyclodextrin is a low cyclic oligosaccharide formed by bonding 6,7, 8D-glucopyranose units by a-1,4, and has high yield, low price and wide application. The cyclodextrin has a hydrophobic cavity with a certain size, so that various organic guest molecules can be selectively included, and meanwhile, the cyclodextrin has good water solubility due to the hydrophilicity of polyhydroxy outside, so that the effect of solubilizing the insoluble drugs is achieved.
Chitosan is a product obtained by deacetylating chitin, is a few natural polysaccharides of cationic high-molecular polymers, and has unique functions in many fields. Chitosan has the advantages of excellent biocompatibility and film-forming property, wettability, moisture retention, antistatic effect, hair softening and protecting effect, no irritation and toxicity to skin and the like, and is widely applied in the field of cosmetics. At present, many large-scale cosmetic companies such as japan, germany, france, etc. have used chitosan in large quantities as a raw material for development, and domestic cosmetics using chitosan as a raw material have also entered the market. The chitosan and other high molecular substances are compounded to prepare skin care products such as facial masks and the like, and due to good hydrophilicity and protein affinity, the skin care products have no allergy, no toxicity and no irritant reaction to the skin, and the contact feeling of the products and the skin is obviously soft in the film forming process, and the affinity to the skin is obviously improved.
Salicylic acid is used in skin care products in an amount up to 2% of the maximum allowable amount (mainly for pox-removing products) according to the 2012 edition of cosmetic hygiene code. Therefore, the product should meet the solubility requirement of 2% of pure salicylic acid.
The invention content is as follows:
based on the technical problems and the application defects in the prior art, the invention provides a novel water-soluble salicylic acid microsphere and a preparation method thereof, aiming at the problems in the prior art, the novel water-soluble salicylic acid microsphere is composed of a plurality of active ingredients, and the active ingredients have a synergistic effect with each other, so that the whitening and acne removing effects of salicylic acid are effectively exerted, the solubility of salicylic acid in water can be increased, the irritation of salicylic acid in use is reduced, and the stability is strong.
The solubility of the salicylic acid in water is enhanced by using the amylopectin, the modified starch and the cyclodextrin, so that the solubility of the salicylic acid in the water is more than 2 percent; the natural polymer compound chitosan is utilized to not only reduce the irritation of salicylic acid in application, but also increase the effects of slowing down aging and modifying beauty.
The novel water-soluble salicylic acid microspheres are prepared by the following method
Adding cyclodextrin and salicylic acid into water with the mass ratio of 1:1.5-2.5 of cyclodextrin to 80-100 times of that of cyclodextrin, ultrasonically dispersing, and fully dissolving at 40-100 ℃ to obtain salicylic acid-cyclodextrin inclusion compound solution;
respectively adding 0.5-1.0g of maltodextrin and 1.0-2.0g of amylopectin into 100g of water, fully dissolving at 60-100 ℃ to obtain a salicylic acid solution, then respectively adding 0.2-0.5g of chitosan and 0.5-1.0g of Arabic gum into the salicylic acid solution according to the amount of 0.2-0.5g of chitosan and 0.5-1.0g of Arabic gum into 100g of water, fully dissolving at 60-100 ℃ to obtain a final solution, and then spray-drying the final solution to obtain the water-soluble salicylic acid microspheres.
Preferably, adding the cyclodextrin and the salicylic acid into water with the mass ratio of 1:1.5-2.5 of the cyclodextrin to 80-100 times of the mass of the cyclodextrin, performing ultrasonic dispersion, and stirring at 40-100 ℃ and 500rpm for 1-2 hours to obtain a salicylic acid-cyclodextrin inclusion compound solution;
respectively adding 0.5-1.0g of maltodextrin and 1.0-2.0g of amylopectin into 100g of water, stirring at the temperature of 60-100 ℃ and the rpm of 500 for 0.5-1.0 h to obtain a salicylic acid solution, respectively adding 0.2-0.5g of chitosan and 0.5-1.0g of Arabic gum into 100g of water, stirring at the temperature of 60-100 ℃ and the rpm of 300-500 for 0.5-1.0 h to obtain a final solution, and spray-drying the final solution to obtain the water-soluble salicylic acid microspheres.
The spray drying is to utilize a spray dryer to rapidly dry the salicylic acid solution, and the drying conditions are set as follows: the feeding temperature is 130-220 ℃, the injection flow rate is 20mL/min, the air flow is 0.3Mpa, and the discharging temperature is controlled between 60-100 ℃.
The invention has the following beneficial effects:
1. has very low irritation to skin without affecting the skin care effect of whitening and removing acne.
2. The water-soluble salicylic acid microspheres have high water solubility, the solubility of the water-soluble salicylic acid microspheres is up to 5 percent, the solubility of the salicylic acid microspheres is up to 2 percent, and the aqueous solution stability of the water-soluble salicylic acid microspheres is high.
3. The invention has simple production process and convenient use.
Description of the drawings:
fig. 1 is a standard curve.
The specific implementation mode is as follows:
the following examples are further illustrative of the present invention and are not intended to be limiting thereof.
Example 1:
(1) preparation of water-soluble salicylic acid microspheres
Adding cyclodextrin and salicylic acid into deionized water 90 times of the cyclodextrin in a mass ratio of 1:2, ultrasonically dispersing for 5 minutes at room temperature, transferring the mixture into a 70 ℃ water bath pot, heating, and stirring at 400rpm for 1.5 hours to obtain a salicylic acid-cyclodextrin inclusion compound solution;
respectively adding 0.8g of maltodextrin and 1.5g of amylopectin into 100g of water, stirring at 80 ℃ and 400rpm for 0.8 hour to obtain a salicylic acid solution, fully dissolving salicylic acid, respectively adding 0.35g of chitosan and 0.75g of Arabic gum into 100g of water, stirring at 80 ℃ and 400rpm for 0.75 hour to fully dissolve the chitosan and the Arabic gum, respectively, thus obtaining a final solution, and spray-drying the final solution to obtain the water-soluble salicylic acid microspheres.
The spray drying is to utilize a spray dryer to rapidly dry the salicylic acid solution, and the drying conditions are set as follows: the feeding temperature is 130-.
(2) Solubility of Water-soluble salicylic acid and stability test thereof
1. Weighing 5g of water-soluble salicylic acid microspheres to be dissolved in 100mL of deionized water, and stirring until the water-soluble salicylic acid microspheres are completely dissolved to obtain a salicylic acid microsphere solution.
2. The dissolved clarified salicylic acid microsphere solution was stored at low temperature (<0 ℃), room temperature (about 25 ℃) and high temperature (55 ℃) respectively.
3. The appearance of the solution was observed every other week, and the change was recorded in time for 2 months.
4. The results of the storage stability (two months) of the aqueous salicylic acid microspheres solution are given in table 1:
table 1:
5. the experimental results show that the solubility of the salicylic acid microspheres in water is higher and reaches 5%, and the salicylic acid microsphere solution has strong stability at low temperature, room temperature and high temperature, which shows that the salicylic acid has higher water solubility and stability in the practical application of skin care products.
(3) Salicylic acid encapsulation rate test in water-soluble compound
1. 10mg of salicylic acid is weighed and dissolved in 100mL of ethanol to prepare 0.1g/L of salicylic acid ethanol standard solution.
2. 0.1g/L salicylic acid solutions were diluted to 1, 2,5, 10 and 20mg/L and the absorbances were measured respectively by an ultraviolet spectrophotometer with the maximum absorption wavelength set at 300nm and recorded respectively as in Table 2:
TABLE 2
3. The above experimental data are analyzed linearly, and standard curves are made as shown in figure 1:
4. weighing 0.1g of water-soluble salicylic acid microspheres in 50mL of ethanol, and performing ultrasonic dispersion for 10 minutes to obtain a salicylic acid microsphere ethanol mixed solution.
5. Transferring the mixed solution of salicylic acid microspheres and ethanol to a constant temperature oscillator, keeping the temperature at 35 ℃, and oscillating for more than 8 hours at 150 rpm.
6. Taking out the mixed solution of salicylic acid microspheres and ethanol, filtering with a filter membrane, and collecting the filtrate.
7. After diluting the filtrate by 100 times, the absorbance of the filtrate was measured, and the concentration of salicylic acid in the filtrate was calculated according to a standard curve.
Wherein: absorbance a is 0.201
The concentration of salicylic acid in the filtrate was: 0.201/0.0247-8.14 mg/L
The encapsulation rate of salicylic acid in the salicylic acid microspheres is as follows:
8. the results show that the encapsulation rate of the salicylic acid in the water-soluble salicylic acid microspheres is up to more than 40%, which also indicates that the water-soluble salicylic acid microspheres can retain skin care functions of whitening, removing acnes and the like in practical application.
(4) Irritation test of water-soluble salicylic acid microspheres in application
1.5g of water-soluble salicylic acid microspheres are weighed and dissolved in 100mL of deionized water, and stirred to be fully dissolved to prepare 5% salicylic acid microsphere solution.
2. And after the salicylic acid microsphere solution is cooled to room temperature, adding a blank mask product, standing for 10 minutes to enable the mask to fully absorb the active ingredients in the compound solution, thus obtaining the compound mask.
3. Randomly 10 persons were selected, the left face was compared with a blank mask, the right face was covered with a mask absorbing the complex (complex mask), the duration was kept for 15 to 20 minutes, and the feeling of use of each person was recorded, and the results are shown in table 3:
TABLE 3
The experimental results show that the water-soluble salicylic acid microspheres have low irritation (only 10% of experimenters feel micro-irritation) in the application of the beauty and skin care facial mask, which shows that the novel water-soluble salicylic acid microspheres effectively solve the problem of high irritation of pure salicylic acid in the application and obviously improve the application value of the salicylic acid in skin care products.
Example 2:
adding cyclodextrin and salicylic acid into water with the mass ratio of 1:1.5 of cyclodextrin to 80 times of the mass of cyclodextrin, performing ultrasonic dispersion, and stirring at 40 ℃ and 300rpm for 1 hour to obtain a salicylic acid-cyclodextrin inclusion compound solution;
maltodextrin and pullulan were added to a salicylic acid-cyclodextrin inclusion compound solution in amounts of 0.5g of maltodextrin and 1.0g of pullulan per 100g of water, respectively, followed by stirring at 60 ℃ and 300rpm for 0.5 hour to obtain a salicylic acid solution, and then chitosan and gum arabic in amounts of 0.2g of chitosan and 0.5g of gum arabic per 100g of water, respectively, were added to the salicylic acid solution, followed by stirring at 60 ℃ and 300rpm for 0.5 hour to obtain a final solution, and the final solution was spray-dried to obtain water-soluble salicylic acid microspheres.
The spray drying is to utilize a spray dryer to rapidly dry the salicylic acid solution, and the drying conditions are set as follows: the feeding temperature is 130-220 ℃, the injection flow rate is 20mL/min, the air flow is 0.3Mpa, and the discharging temperature is controlled between 60-100 ℃.
The solubility and stability tests of the water-soluble salicylic acid microspheres in the embodiment are the same as those in the embodiment 1, and the solubility of the salicylic acid microspheres in water is proved to be higher and reaches 5%, and the salicylic acid microsphere solution has strong stability at low temperature, room temperature and high temperature, which shows that the salicylic acid has higher water solubility and stability in the practical application of skin care products. And the encapsulation rate test shows that the encapsulation rate of the salicylic acid in the water-soluble salicylic acid microspheres is up to more than 40%, which also shows that the water-soluble salicylic acid microspheres can retain the skin care functions of whitening, removing acnes and the like in practical application. And through irritation tests, the water-soluble salicylic acid microspheres have low irritation (only 10% of experimenters feel micro irritation) in the application of the beauty and skin care mask, which shows that the novel water-soluble salicylic acid microspheres effectively solve the problem of high irritation of pure salicylic acid in the application and obviously improve the application value of the salicylic acid in skin care products.
Example 3:
adding cyclodextrin and salicylic acid into water with the mass ratio of 1:2.5 of cyclodextrin to 100 times of the mass of cyclodextrin, performing ultrasonic dispersion, and stirring at 100 ℃ and 500rpm for 2 hours to obtain a salicylic acid-cyclodextrin inclusion compound solution;
maltodextrin and pullulan were added to a salicylic acid-cyclodextrin inclusion compound solution in amounts of 1.0g of maltodextrin and 2.0g of pullulan per 100g of water, respectively, followed by stirring at 100 ℃ and 500rpm for 1.0 hour to obtain a salicylic acid solution, and then chitosan and gum arabic in amounts of 0.5g of chitosan and 1.0g of gum arabic per 100g of water, respectively, were added to the salicylic acid solution, followed by stirring at 100 ℃ and 500rpm for 1.0 hour to obtain a final solution, and the final solution was spray-dried to obtain water-soluble salicylic acid microspheres.
The spray drying is to utilize a spray dryer to rapidly dry the salicylic acid solution, and the drying conditions are set as follows: the feeding temperature is 130-220 ℃, the injection flow rate is 20mL/min, the air flow is 0.3Mpa, and the discharging temperature is controlled between 60-100 ℃.
The solubility and stability tests of the water-soluble salicylic acid microspheres in the embodiment are the same as those in the embodiment 1, and the solubility of the salicylic acid microspheres in water is proved to be higher and reaches 5%, and the salicylic acid microsphere solution has strong stability at low temperature, room temperature and high temperature, which shows that the salicylic acid has higher water solubility and stability in the practical application of skin care products. And the encapsulation rate test shows that the encapsulation rate of the salicylic acid in the water-soluble salicylic acid microspheres is up to more than 40%, which also shows that the water-soluble salicylic acid microspheres can retain the skin care functions of whitening, removing acnes and the like in practical application. And through irritation tests, the water-soluble salicylic acid microspheres have low irritation (only 10% of experimenters feel micro irritation) in the application of the beauty and skin care mask, which shows that the novel water-soluble salicylic acid microspheres effectively solve the problem of high irritation of pure salicylic acid in the application and obviously improve the application value of the salicylic acid in skin care products.
Comparative example 1:
in the step of preparing the water-soluble salicylic acid microspheres, the addition amount of the amylopectin is reduced to 0.5-1.0% in the salicylic acid-cyclodextrin inclusion compound solution, and the other preparation steps or the addition amount of the raw materials are the same as those in example 1.
After the preparation, the encapsulation rate of the salicylic acid in the water-soluble salicylic acid microspheres is more than 45%, and the irritation is weak (only 10% of experimenters feel slight irritation), however, after 5g of the water-soluble salicylic acid microspheres are dissolved in 100mL of deionized water to prepare a 5% aqueous solution, and the aqueous solution is placed at a low temperature (0 ℃) for one week, a large amount of precipitates are separated out, and the low-temperature stability is poor.
Comparative example 2:
in the step of preparing the water-soluble salicylic acid microspheres, the addition amount of the chitosan is reduced to be more than or equal to 0.1 percent and less than 0.2 percent in the salicylic acid-cyclodextrin inclusion compound solution, and the addition amount of other preparation steps or raw materials is the same as that of the example 1.
After the preparation, the encapsulation rate of salicylic acid in the water-soluble salicylic acid microspheres is more than 45%, 5g of the salicylic acid microspheres are dissolved in 100mL of deionized water to prepare a 5% aqueous solution, and the aqueous solution is placed at high temperature, room temperature and low temperature (less than 0 ℃) for two months, so that the aqueous solution is clear, no precipitate is separated out, and the stability is strong. However, as tested by random irritation test, more than 50% of experimenters feel obvious irritation, and the irritation is obviously improved by reducing the dosage of chitosan.
Comparative example 3:
in the step of preparing the water-soluble salicylic acid microspheres, the addition amount of the cyclodextrin is reduced to 0.2-0.5% in the salicylic acid-cyclodextrin inclusion compound solution, and the addition amount of other preparation steps or raw materials is the same as that of the example 1.
In the preparation process, the maltodextrin and the amylopectin are added into the salicylic acid-cyclodextrin inclusion compound solution according to the dosage of the embodiment 1, the temperature of a water bath is set to be 60-80 ℃, the electric stirring is carried out for 0.5-1.0 hour under the condition of keeping the rotation speed of 500rpm at 300-.
Claims (2)
1. The preparation method of the water-soluble salicylic acid microspheres is characterized by comprising the following steps of:
adding cyclodextrin and salicylic acid into water with the mass ratio of 1:2, wherein the mass ratio of cyclodextrin to salicylic acid is 90 times that of cyclodextrin, ultrasonically dispersing for 5 minutes, and stirring at the temperature of 70 ℃ and the speed of 400rpm for 1.5 hours to obtain a salicylic acid-cyclodextrin inclusion compound solution;
adding maltodextrin and amylopectin into salicylic acid-cyclodextrin clathrate solution in an amount of 0.8g and 1.5g of maltodextrin per 100g of water, stirring at 80 deg.C and 400rpm for 0.8 hr to obtain salicylic acid solution, adding chitosan and acacia into salicylic acid solution in an amount of 0.35g and 0.75g per 100g of water, stirring at 80 deg.C and 400rpm for 0.75 hr to obtain final solution, and spray drying to obtain water-soluble salicylic acid microsphere;
the spray drying is to utilize a spray dryer to rapidly dry the salicylic acid solution, and the drying conditions are set as follows: the feeding temperature is 130-220 ℃, the injection flow rate is 20mL/min, the air flow is 0.3Mpa, and the discharging temperature is controlled between 60-100 ℃.
2. A water-soluble salicylic acid microsphere prepared by the method of claim 1.
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| CN112386522B (en) * | 2019-08-13 | 2022-03-18 | 珀莱雅化妆品股份有限公司 | Salicylic acid supermolecule preparation and preparation method thereof |
| WO2022162620A2 (en) * | 2021-01-29 | 2022-08-04 | L'oreal | Cleansing composition providing enhanced deposition of salicylic acid for acne treatment |
| FR3122576B1 (en) * | 2021-05-04 | 2024-04-19 | Oreal | CLEANSING COMPOSITION PROVIDING AN IMPROVED SALICYLIC ACID DEPOSIT FOR THE TREATMENT OF ACNE |
| CN114392225A (en) * | 2022-01-27 | 2022-04-26 | 广州兰皙化妆品有限公司 | Acne removing essence and preparation method thereof |
| CN114795988A (en) * | 2022-03-07 | 2022-07-29 | 山东滨州智源生物科技有限公司 | Water-soluble salicylic acid and preparation method and application thereof |
| CN115521200A (en) * | 2022-09-19 | 2022-12-27 | 云南勐牛生物技术有限公司 | High-content salicylic acid solution and preparation method thereof |
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| CN101288483A (en) * | 2008-05-12 | 2008-10-22 | 江阴天江药业有限公司 | Preparation method of ginger and jujube granule |
| CN102697666A (en) * | 2012-05-30 | 2012-10-03 | 复旦大学 | Cyclodextrin salicylic acid inclusion complex aqueous solution, as well as preparation method and application thereof |
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