CN110664622A - Preparation method of moisturizing spray containing water-soluble cannabidiol - Google Patents

Preparation method of moisturizing spray containing water-soluble cannabidiol Download PDF

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CN110664622A
CN110664622A CN201910995262.9A CN201910995262A CN110664622A CN 110664622 A CN110664622 A CN 110664622A CN 201910995262 A CN201910995262 A CN 201910995262A CN 110664622 A CN110664622 A CN 110664622A
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water
cannabidiol
albumin
stirring
parts
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王钲霖
刘胜贵
付彬彬
李智高
孔令羽
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Yunnan Luxin Biopharmaceutical Co Ltd
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Yunnan Luxin Biopharmaceutical Co Ltd
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    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
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    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34Alcohols
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    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
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    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
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    • A61K8/37Esters of carboxylic acids
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    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
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    • A61K8/64Proteins; Peptides; Derivatives or degradation products thereof
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    • A61K8/67Vitamins
    • A61K8/673Vitamin B group
    • A61K8/675Vitamin B3 or vitamin B3 active, e.g. nicotinamide, nicotinic acid, nicotinyl aldehyde
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Abstract

The invention belongs to the field of daily cosmetics, and particularly relates to a preparation method of a moisturizing spray containing water-soluble cannabidiol. The composition comprises the following raw and auxiliary materials: 35-50 parts of deionized water, 20-45 parts of jasmine flower water, 2-8 parts of glycerol, 2-8 parts of butanediol, 0.5-3 parts of oat-beta-glucan, 0.1-10 parts of water-soluble cannabidiol, 0.05-0.6 part of sodium hyaluronate, 0.1-1 part of nicotinamide, 0.1-1 part of palmitoyl oligopeptide, 0.1-1 part of carnosine, 0.2-0.8 part of xanthan gum, 0.05-0.5 part of menthol, 0.1-0.5 part of EDTA-2Na and 0.1-0.3 part of ethylparaben. The fat-soluble cannabidiol is included by the water-soluble packaging material, so that the addition amount of the cannabidiol in the spray is increased. The moisturizing spray has excellent effects of diminishing inflammation, removing wrinkles, moisturizing and whitening.

Description

Preparation method of moisturizing spray containing water-soluble cannabidiol
Technical Field
The invention belongs to the field of daily cosmetics, and particularly relates to a preparation method of a moisturizing spray containing water-soluble cannabidiol.
Background
Cannabis sativa L, also known as Cannabis sativa L, is a plant of the genus Cannabis of the family Moraceae, an annual upright herb, 1-3 meters high. Cannabis is generally classified into two types, industrial cannabis and narcotic cannabis, according to the proportion of Tetrahydrocannabinol (THC) contained therein. The industrial cannabis belongs to low-toxicity cannabis, wherein the content of Tetrahydrocannabinol (THC) is not more than 0.3 percent at most, and the industrial cannabis has no drug utilization value; the content of Tetrahydrocannabinol (THC) in the leaves and the flower branches of the drug marijuana is high, and the drug marijuana belongs to high-toxicity marijuana. At present, more than 80 Cannabinoids (CBs) have been isolated from cannabis, mainly including Cannabidiol (CBD), Tetrahydrocannabinol (THC), Cannabinol (CBN), cannabigerol (CBC), etc., wherein the content of Cannabidiol (CBD) and Tetrahydrocannabinol (THC) is the highest, and is a typical representative of cannabinoids. Researches show that Tetrahydrocannabinol (THC) has addiction hallucinogenic property, so that the application and the development of the THC in the field of medicine are greatly limited. Cannabidiol (CBD), unlike Tetrahydrocannabinol (THC), is not only a potent antioxidant, but is also a non-addictive active ingredient with no neurotoxicity, and antagonizes the psychotropic activity induced by the THC agonistic cannabinoid type I receptor (CB 1R).
In recent years, research shows that Cannabidiol (CBD) has a series of physiological functions of sedation and hypnosis, epilepsy treatment, neuroprotection, tumor treatment and the like, and is a natural active component with great application prospect in the fields of medicine and the like. In addition, industrial hemp flower and leaf extract is used as an effective ingredient or an additive in the preparation of skin care products, and a trend has been developed. The skin care product has the effects of relieving pain, resisting inflammation, removing speckle, removing yellow, acne, resisting aging, resisting wrinkle and the like, and can quickly cover the skin care product consumer market, particularly the European skin care product market. The existing skin care products for whitening and moistening skin, such as removing acne, removing wrinkles and the like, basically stay temporary or repair on the surface layer, and cannot fundamentally solve the skin problem. However, Cannabidiol (CBD) and other cannabis extracts are nontoxic substances extracted from cannabis leaves and can be used in various fields such as medicines, cosmetics and health foods with high added value.
There are some reports in the current disclosure regarding the use of industrial cannabis extracts in the skin care industry. For example, CN107982080A discloses the use of cannabidiol or cannabis extract in the preparation of whitening products, which verifies that cannabidiol or cannabis extract can effectively inhibit the activity of tyrosinase, and has good skin whitening effect. But no specific preparation scheme is provided. CN107811904A discloses an anti-inflammatory and freckle-removing vanishing cream and a preparation method thereof, the anti-inflammatory and freckle-removing vanishing cream is added with a special cannabis sativa leaf extract rich in bisabolol and cannabidiol, and has obvious anti-inflammatory and freckle-removing effects, wherein the rich bisabolol is reserved to synergistically enhance the anti-inflammatory and freckle-removing effects of the cannabidiol, and the cannabis sativa leaf extract can be maintained to play stronger anti-inflammatory and freckle-removing effects in a longer time. CN107308440A discloses a skin care product for removing striae gravidarum, repairing scars, removing wrinkles and whitening skin, which comprises monarch drug, ministerial drug, adjuvant drug and conductant drug, wherein the monarch drug comprises oligopeptide and cannabidiol, the ministerial drug comprises sodium carboxymethyl dextran and sodium hyaluronate, the adjuvant drug comprises olive essential oil, vitamin E, almond extract, dandelion extract, purslane extract, bighead atractylodes rhizome extract, panax notoginseng freeze-dried powder, poria cocos extract, bletilla striata extract and coix seed extract, and the conductant drug comprises licorice extract and deionized water. CN109846790A discloses a spray containing cannabidiol for moisturizing acne removal and brightening skin and a preparation method thereof, wherein the added cannabidiol special-purpose cannabis sativa leaf extract is cooperated with argania spinosa kernel extract, centella asiatica extract, tea leaf extract and hydrolyzed myrtle extract, so that the spray has better moisturizing and whitening effects on dry skin, dark skin, acne, pimples and the like. Through comparison and research of various existing skin care products related to cannabidiol, the cannabidiol which is a main additive of the existing skin care products containing industrial cannabis extract is found to be a fat-soluble substance, and for most cosmetics with high water content, the low solubility of the cannabidiol severely limits the addition amount of the cannabidiol, so that the ideal skin care effect cannot be achieved.
Disclosure of Invention
In view of the above problems, the present invention provides a method for preparing a moisturizing spray containing water-soluble cannabidiol. The water-soluble Cannabidiol (CBD) is embedded by utilizing a water-soluble packing material to form an inclusion compound, and the inclusion compound is prepared into a molecular capsule, so that the solubility of the CBD in water is improved by thousands of times, and the problem of water solubility is thoroughly solved. Further increasing the addition of CBD in the spray, so that the spray has excellent effects of antibiosis, antiphlogosis, whitening, wrinkle removal and moisture preservation.
In order to realize the aim, the invention provides a preparation method of a moisturizing spray containing water-soluble cannabidiol, which comprises the following raw materials and auxiliary materials: 35-50 parts of deionized water, 20-45 parts of jasmine flower water, 2-8 parts of glycerol, 2-8 parts of butanediol, 0.5-3 parts of oat-beta-glucan, 0.1-10 parts of water-soluble cannabidiol, 0.05-0.6 part of sodium hyaluronate, 0.1-1 part of nicotinamide, 0.1-1 part of palmitoyl oligopeptide, 0.1-1 part of carnosine, 0.2-0.8 part of xanthan gum, 0.05-0.5 part of menthol, 0.1-0.5 part of EDTA-2Na and 0.1-0.3 part of ethylparaben.
The preparation method of the water-soluble cannabidiol comprises the following steps:
(1) weighing CBD powder, adding into a proper amount of organic solvent, and fully stirring for dissolving to obtain an organic phase containing CBD.
(2) Weighing albumin, dissolving the albumin in a proper amount of deionized water, stirring, and heating to fully dissolve the albumin to obtain an albumin aqueous solution. Adjusting the pH value of the albumin aqueous solution to 6.0, and adding a proper amount of organic solvent to obtain a water phase.
(3) Slowly dripping the organic phase into the water phase under high speed stirring, and stirring for a certain time to obtain oil-in-water type emulsion solution.
(4) And transferring the oil-in-water type emulsion solution into a high-pressure micro-jet nano dispersing instrument for high-pressure homogenization.
(5) After completion of homogenization, the mixture was concentrated using a rotary evaporator to remove the organic solvent.
(6) Freeze-drying at low temperature to obtain water-soluble cannabidiol.
In the step (1), the organic solvent comprises methanol, ethanol, isopropanol, acetonitrile or a mixed solvent of some of the methanol, the ethanol, the isopropanol and the acetonitrile; preferably, the organic solvent is ethanol.
In the step (2), the albumin comprises bovine serum albumin and human serum albumin; bovine serum albumin is preferably used as albumin; the concentration of the albumin aqueous solution is 1-6% by mass, and the preferable mass percentage is 4%; the organic solvent comprises methanol, ethanol, isopropanol, acetonitrile or a mixture thereof. Preferably the organic solvent is ethanol; the adding amount of the organic solvent is 1-4% of the mass of the albumin water solution, and the preferable mass percentage is 1%.
In the step (3), the volume ratio of the oil phase to the water phase is 1 (8-12). More preferably, the oil phase, the water phase 1: 10; stirring at a high speed of 5000-10000 r/min; the stirring time is 0.5-5 h.
In the step (4), the high-pressure homogenizing pressure is 1000bar, and the homogenizing times are 7-16 times. Preferably, the number of homogenizations is 10.
In the step (5), the rotary evaporation vacuum degree is-0.05 to-0.1 MPa, and the temperature is 25 to 45 ℃.
In the step (6), low-temperature freeze drying is carried out in a freeze dryer, and the drying time is 36-72 hours.
A method for preparing a moisturizing spray containing water-soluble cannabidiol comprises the following steps:
(1) taking a round-bottom flask, sequentially adding a certain amount of deionized water and jasmine water, placing in a 70 ℃ water bath, and stirring.
(2) After the temperature is stable, accurately weighing a certain amount of EDTA-2Na and menthol, adding into a flask, and stirring until the EDTA-2Na and the menthol are dissolved; then sequentially adding oat-beta-glucan and sodium hyaluronate.
(3) After the solution was clarified, xanthan gum was dissolved in the mixture of glycerol and butylene glycol, added to the flask, stirred to dissolve completely, and the water bath temperature was adjusted to 50 ℃.
(4) When the temperature is reduced to 50 ℃, sequentially adding a certain amount of water-soluble CBD, nicotinamide, palmitoyl oligopeptide and carnosine, and cooling to room temperature after complete dissolution; adding ethylparaben, and stirring.
The invention has the beneficial effects that:
(1) the invention embeds the target molecule with the packing material with better water solubility under the condition that the molecular structure of the CBD which is not dissolved in water is not changed, so that the water solubility of the CBD is changed, and the addition amount of the CBD in the spray is increased by one thousand times.
(2) According to the spray disclosed by the invention, cannabidiol, nicotinamide and polypeptides are compounded for use, so that the effects of diminishing inflammation, removing wrinkles, moisturizing, whitening and nourishing are exerted more comprehensively, and the spray has auxiliary effects of diminishing inflammation, resisting oxidation, inhibiting bacteria and the like while moisturizing the skin, and plays a role in comprehensively improving the problem of dry skin.
(3) The natural spraying component of the invention is safe, mild and multiple-effect, and the preparation process is simple.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail with reference to the following embodiments.
Example 1
Preparation of water-soluble cannabidiol
(1) Accurately weighing 2g of CBD powder, adding into 10g of ethanol, and fully stirring for dissolving to obtain an organic phase containing CBD.
(2) Accurately weighing 4.76g of albumin, dissolving the albumin in 100g of deionized water, stirring, and heating to fully dissolve the albumin to obtain an albumin aqueous solution. Dropwise adding 1mol/L hydrochloric acid, adjusting the pH value of the albumin water solution to 6.0, adding 1g of ethanol, and uniformly stirring and mixing to obtain a water phase.
(3) Placing the water phase in a 30 deg.C water bath, and mechanically stirring at 5000 r/min. After the temperature is stable, slowly dripping the organic phase into the water phase, and fully stirring for 3h to obtain the oil-in-water type emulsion solution.
(4) And transferring the oil-in-water type emulsion solution into a high-pressure micro-jet nano dispersing instrument for high-pressure homogenization. The homogenization pressure was 1000bar and the number of homogenization times was 10.
(5) After homogenization, the mixture is concentrated by using a rotary evaporator, and the rotary evaporation vacuum degree is minus 0.1MPa and the temperature is 30 ℃.
(6) And freeze-drying the concentrate in a freeze dryer for 36h to obtain the water-soluble cannabidiol albumin nanoparticles.
Preparation of water-soluble cannabidiol moisturizing spray
(1) A250 ml round-bottom flask was taken, 58.9g of deionized water and 30g of jasmine water were added thereto in this order, and the mixture was placed in a 70 ℃ water bath and stirred.
(2) After the temperature is stable, accurately weighing 0.1g of EDTA-2Na and 0.1g of menthol, adding into a flask, and stirring until the EDTA-2Na and the menthol are dissolved; then 2.2g oat-beta-glucan and 0.45g sodium hyaluronate were added in sequence.
(3) After the solution was clear, 0.05g of xanthan gum was dissolved in a mixture of 2.5g of glycerol and 3g of butylene glycol, added to the flask, stirred until completely dissolved, and the temperature of the water bath was adjusted to 50 ℃.
(4) When the temperature is reduced to 50 ℃, sequentially adding 0.8g of water-soluble CBD, 0.6g of nicotinamide, 0.5g of palmitoyl oligopeptide and 0.5g of carnosine, and cooling to room temperature after complete dissolution; adding 0.3g of ethylparaben, and stirring uniformly.
Example 2
Preparation of water-soluble cannabidiol
The same as in example 1.
Preparation of water-soluble cannabidiol moisturizing spray
(1) A250 ml round-bottom flask was taken, and 58.1g of deionized water and 30g of jasmine water were added thereto in this order, and the mixture was placed in a 70 ℃ water bath and stirred.
(2) After the temperature is stable, accurately weighing 0.1g of EDTA-2Na and 0.1g of menthol, adding into a flask, and stirring until the EDTA-2Na and the menthol are dissolved; then 2.2g oat-beta-glucan and 0.45g sodium hyaluronate were added in sequence.
(3) After the solution was clear, 0.05g of xanthan gum was dissolved in a mixture of 2.5g of glycerol and 3g of butylene glycol, added to the flask, stirred until completely dissolved, and the temperature of the water bath was adjusted to 50 ℃.
(4) When the temperature is reduced to 50 ℃, sequentially adding 1.6g of water-soluble CBD, 0.6g of nicotinamide, 0.5g of palmitoyl oligopeptide and 0.5g of carnosine, and cooling to room temperature after complete dissolution; adding 0.3g of ethylparaben, and stirring uniformly.
Example 3
Preparation of water-soluble cannabidiol
The same as in example 1.
Preparation of water-soluble cannabidiol moisturizing spray
(1) A250 ml round-bottom flask was taken, 56.5g of deionized water and 30g of jasmine water were added thereto in this order, and the mixture was placed in a 70 ℃ water bath and stirred.
(2) After the temperature is stable, accurately weighing 0.1g of EDTA-2Na and 0.1g of menthol, adding into a flask, and stirring until the EDTA-2Na and the menthol are dissolved; then 2.2g oat-beta-glucan and 0.45g sodium hyaluronate were added in sequence.
(3) After the solution was clear, 0.05g of xanthan gum was dissolved in a mixture of 2.5g of glycerol and 3g of butylene glycol, added to the flask, stirred until completely dissolved, and the temperature of the water bath was adjusted to 50 ℃.
(4) When the temperature is reduced to 50 ℃, sequentially adding 3.2g of water-soluble CBD, 0.6g of nicotinamide, 0.5g of palmitoyl oligopeptide and 0.5g of carnosine, and cooling to room temperature after complete dissolution; adding 0.3g of ethylparaben, and stirring uniformly.
Experimental example 1 stability study of moisturizing spray
Dividing the moisturizing sprays prepared in examples 1, 2 and 3 into 4 parts respectively, and placing the first part in a cool and ventilated environment at room temperature; the second part is placed in a direct sunlight environment; the third part is placed in a thermostat at 45 ℃; the fourth part is placed in a refrigerator at the temperature of 2 ℃; after three months of storage, the color, uniformity and whether the mildew or rot phenomenon exists are respectively observed. The result shows that the prepared moisturizing spray basically has no change, bright color and no color change under the high-temperature, normal-temperature and low-temperature environments; the uniformity is good, and no mildew occurs; in the direct sunlight environment, the color of the moisturizing spray is slightly darker.
Experimental results show that the moisturizing spray prepared by the invention has good stability in conventional environments. The storage mode is to avoid long-term storage in direct sunlight.
Experimental example 2 trial experiment of volunteers
20 facial skin-dry volunteers, 20 pox-on-face volunteers, 20 dark yellow facial skin volunteers, and 20 wrinkled facial volunteers were searched. The anti-inflammatory spray prepared in example 2 is respectively dispensed to volunteers for use.
The moisture-keeping spray is sprayed on the face of a volunteer, and the spray is applied once in the morning, at noon and evening and continuously for 1 month. The effects of moisturizing, acne removing, whitening and wrinkle removing of the spray are examined, and the trial effect of the volunteers is shown in table 1.
Table 1 trial test results of moisturizing sprays
Figure 143239DEST_PATH_IMAGE002
As can be seen from Table 2, the moisturizing spray prepared by the invention has the effective rate of 100% on moisturizing, acne removing, whitening and wrinkle removing.
The above examples are merely illustrative of the present invention and do not limit the scope of the present invention in any way. It will be apparent to those skilled in the art that equivalent embodiments or modifications without departing from the technical spirit of the present invention are within the scope of the present invention.

Claims (9)

1. A preparation method of a moisturizing spray containing water-soluble cannabidiol is characterized by comprising the following raw and auxiliary materials: 35-50 parts of deionized water, 20-45 parts of jasmine flower water, 2-8 parts of glycerol, 2-8 parts of butanediol, 0.5-3 parts of oat-beta-glucan, 0.1-10 parts of water-soluble cannabidiol, 0.05-0.6 part of sodium hyaluronate, 0.1-1 part of nicotinamide, 0.1-1 part of palmitoyl oligopeptide, 0.1-1 part of carnosine, 0.2-0.8 part of xanthan gum, 0.05-0.5 part of menthol, 0.1-0.5 part of EDTA-2Na and 0.1-0.3 part of ethylparaben.
2. The method for preparing a moisturizing spray containing water-soluble cannabidiol as claimed in claim 1, wherein the method for preparing water-soluble cannabidiol is as follows:
(1) weighing CBD powder, adding into a proper amount of organic solvent, and fully stirring for dissolving to obtain an organic phase containing CBD;
(2) weighing albumin, dissolving the albumin in a proper amount of deionized water, stirring, and heating to fully dissolve the albumin to obtain an albumin aqueous solution;
adjusting the pH value of the albumin aqueous solution to 6.0, and adding a proper amount of organic solvent to obtain a water phase;
(3) slowly dripping the organic phase into the water phase under high-speed stirring, and stirring for a certain time to obtain oil-in-water type emulsion solution;
(4) transferring the oil-in-water type emulsion solution into a high-pressure micro-jet nano dispersing instrument for high-pressure homogenization;
(5) after homogenization, concentrating by using a rotary evaporator, and removing the organic solvent;
(6) freeze-drying at low temperature to obtain water-soluble cannabidiol.
3. The method for preparing a moisture-retaining spray containing cannabidiol as claimed in claim 2, wherein in step (1), the organic solvent comprises methanol, ethanol, isopropanol, acetonitrile or a mixture thereof; preferably, the organic solvent is ethanol.
4. The method for preparing a moisture spray containing cannabidiol as claimed in claim 2, wherein in step (2), the albumin comprises bovine serum albumin, human serum albumin; bovine serum albumin is preferably used as albumin; the concentration of the albumin aqueous solution is 1-6% by mass, and the preferable mass percentage is 4%; the organic solvent comprises methanol, ethanol, isopropanol, acetonitrile or a mixed solvent of some of the above solvents;
preferably the organic solvent is ethanol; the adding amount of the organic solvent is 1-4% of the mass of the albumin water solution, and the preferable mass percentage is 1%.
5. The preparation method of the moisturizing spray containing the water-soluble cannabidiol as claimed in claim 2, wherein in the step (3), the oil phase and the water phase are (8-12) in volume ratio;
more preferably, the oil phase, the water phase 1: 10; stirring at a high speed of 5000-10000 r/min; the stirring time is 0.5-5 h.
6. The method for preparing moisture-keeping spray containing cannabidiol as claimed in claim 2, wherein in step (4), the high-pressure homogenization pressure is 1000bar, and the homogenization times are 7-16;
preferably, the number of homogenizations is 10.
7. The method for preparing the moisture-preserving spray containing the cannabidiol as claimed in claim 2, wherein in the step (5), the rotary evaporation vacuum degree is-0.05 to-0.1 MPa, and the temperature is 25 to 45 ℃.
8. The method for preparing the moisture-preserving spray containing the cannabidiol as claimed in claim 2, wherein in the step (6), the low-temperature freeze drying is performed in a freeze dryer for 36-72 hours.
9. The method for preparing a moisturizing spray containing cannabidiol as claimed in claim 1 and claim anqiu 2, comprising the steps of:
(1) taking a round-bottom flask, sequentially adding a certain amount of deionized water and jasmine water, placing in a 70 ℃ water bath, and stirring;
(2) after the temperature is stable, accurately weighing a certain amount of EDTA-2Na and menthol, adding into a flask, and stirring until the EDTA-2Na and the menthol are dissolved; then sequentially adding oat-beta-glucan and sodium hyaluronate;
(3) after the solution is clarified, dissolving xanthan gum in the mixed solution of glycerol and butanediol, adding the solution into a flask, stirring until the xanthan gum is completely dissolved, and adjusting the temperature of a water bath to 50 ℃;
(4) when the temperature is reduced to 50 ℃, sequentially adding a certain amount of water-soluble CBD, nicotinamide, palmitoyl oligopeptide and carnosine, and cooling to room temperature after complete dissolution; adding ethylparaben, and stirring.
CN201910995262.9A 2019-10-18 2019-10-18 Preparation method of moisturizing spray containing water-soluble cannabidiol Withdrawn CN110664622A (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111494466A (en) * 2020-01-14 2020-08-07 四川大学华西医院 A topical composition containing Cannabis sativa extract and its application
WO2022070191A1 (en) 2020-10-01 2022-04-07 Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. Protein-bound cannabinoid formulations and uses thereof
GB2613781A (en) * 2021-12-07 2023-06-21 Vive Skincare Ltd Skincare compositions

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111494466A (en) * 2020-01-14 2020-08-07 四川大学华西医院 A topical composition containing Cannabis sativa extract and its application
WO2022070191A1 (en) 2020-10-01 2022-04-07 Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. Protein-bound cannabinoid formulations and uses thereof
GB2613781A (en) * 2021-12-07 2023-06-21 Vive Skincare Ltd Skincare compositions

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