CN115089507A - Hydroxy pinacolone retinoic acid ester solution, preparation method thereof and skin external preparation - Google Patents
Hydroxy pinacolone retinoic acid ester solution, preparation method thereof and skin external preparation Download PDFInfo
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- -1 Hydroxy pinacolone retinoic acid ester Chemical class 0.000 title claims abstract description 61
- 229930002330 retinoic acid Natural products 0.000 title claims abstract description 60
- 229960001727 tretinoin Drugs 0.000 title claims abstract description 60
- 238000002360 preparation method Methods 0.000 title claims abstract description 51
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims abstract description 38
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- FOYKKGHVWRFIBD-UHFFFAOYSA-N gamma-tocopherol acetate Natural products CC(=O)OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 FOYKKGHVWRFIBD-UHFFFAOYSA-N 0.000 description 2
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- SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 description 1
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- JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention discloses a hydroxy pinacolone retinoic acid ester solution, a preparation method thereof and a skin external preparation, and belongs to the technical field of skin external preparations. The hydroxy pinacolone retinoic acid ester solution is prepared from the following raw materials in percentage by weight: 4.5-5.5% of hydroxy pinacolone retinate, 1.8-2.2% of artificial cell membrane, 10-18% of coconut oil alcohol-caprylic acid ester/caprate, 4.0-12.0% of caprylic acid/capric acid triglyceride and 38.0-45.0% of isononyl isononanoate, and the rest is caprylic acid/capric acid glyceride. The hydroxy pinacolone retinoic acid ester solution is clear and transparent, has good safety, no cytotoxicity and good skin permeability. In addition, the preparation process is simple, the operation is convenient, and the anti-aging cream has good anti-aging effect and no adverse reaction when being applied to skin external preparations, especially anti-aging essences.
Description
Technical Field
The invention relates to the technical field of skin external preparations, in particular to a hydroxy pinacolone retinoic acid ester solution, a preparation method thereof and a skin external preparation.
Background
The market scale of the anti-aging cosmetics shows a continuous acceleration trend, the speed is 472 hundred million yuan in 2018, the speed increase is 17.0 percent in year, 907 hundred million yuan is estimated to be achieved in 2022, and the increase is more than doubled in 2018. It has been reported that the skin gradually enters a natural aging state from the age of 20 to 25 years, and the aging rate varies according to the genetic and lifestyle habits of each person. Due to the influence of factors such as fast-paced life, night-out, working pressure and the like, the skin is easy to have aging symptoms, such as fragile, easy to be allergic, dry and tight, fine wrinkles, slow recovery speed after the skin is suntan and the like.
The anti-aging cosmetic is in the form of solution, emulsion, paste, powder and the like, wherein the most common anti-aging cosmetic is solution type cosmetics, namely essence, in order to dissolve water-soluble anti-aging components, the water content in the formula is higher, so that the addition amount of the oil-soluble anti-aging components in the essence is generally lower, the unstable phenomena such as precipitation and the like are easily caused once the addition amount is too high, and products added with more oil-soluble anti-aging components are always in a turbid state and cannot be in a transparent state.
Hydroxy pinacolone retinoic acid ester (hereinafter, abbreviated as HPR) belongs to a retinoid and has a good anti-aging effect, but it is insoluble in water and oil, and is difficult to use in aqueous cosmetics, particularly transparent essential cosmetics.
In view of this, the invention is particularly proposed.
Disclosure of Invention
It is an object of the present invention to provide a hydroxy pinacolone retinoic acid ester solution to solve the above technical problems.
The second object of the present invention is to provide a method for preparing the above hydroxy pinacolone retinoic acid ester solution.
The invention also aims to provide a skin external preparation prepared from the hydroxy pinacolone retinoic acid ester solution.
The application can be realized as follows:
in a first aspect, the present application provides a hydroxy pinacolone retinoic acid ester solution, which comprises the following raw materials in percentage by weight: 4.5-5.5% of hydroxy pinacolone retinate, 1.8-2.2% of artificial cell membrane, 10-18% of coconut oil alcohol-caprylate/caprate, 4.0-12.0% of caprylic/capric triglyceride and 38.0-45.0% of isononyl isononanoate, and the balance of caprylic/capric glyceride.
In an alternative embodiment, the artificial cell membrane is polyquaternium-51.
In an alternative embodiment, the preparation stock also includes, in the same weight percentages, 0.4 to 1% of an antioxidant.
In an alternative embodiment, the antioxidant is an oil soluble antioxidant.
In an alternative embodiment, the antioxidant is tocopheryl acetate.
In a second aspect, the present application provides a process for the preparation of a solution of hydroxy pinacolone retinoic acid ester according to any one of the preceding embodiments, comprising the steps of: mixing the preparation raw materials according to the proportion.
In an alternative embodiment, the preparing comprises:
mixing the artificial cell membrane, hydroxy pinacolone retinoic acid ester and coconut oil alcohol-caprylate/caprate to obtain a first mixture;
mixing caprylic/capric triglyceride, isononyl isononanoate and caprylic/capric triglyceride to obtain a second mixture;
mixing the first mixed material and the second mixed material.
In an alternative embodiment, when an antioxidant is present in the preparation stock, the mixture of the first and second mixes is mixed with the antioxidant.
In an alternative embodiment, the artificial cell membrane, hydroxy pinacolone retinate and coco-caprylate/caprate are mixed with stirring at 40-60 ℃.
In an alternative embodiment, the mixing time is 25-40 min.
In a third aspect, the present application provides an external preparation for skin prepared from a solution of hydroxyppinacolone retinoic acid ester according to any one of the preceding embodiments.
In an alternative embodiment, the external preparation for skin includes a cosmetic.
In an alternative embodiment, the cosmetic is an aqueous cosmetic.
In an alternative embodiment, the aqueous cosmetic is a serum-based cosmetic or a gel-based cosmetic.
The beneficial effect of this application includes:
according to the application, hydroxy pinacolone retinoic acid ester is loaded in a bilayer molecular layer of an artificial cell membrane under the auxiliary action of coconut oil alcohol-caprylic acid ester/capric acid ester in a reasonable ratio, and then the hydroxy pinacolone retinoic acid ester is dissolved in a mixture of caprylic acid/capric acid triglyceride, isononyl isononanoate and caprylic acid/capric acid triglyceride in a specific ratio to prepare a clear, transparent and stable solution, so that the convenience of formula application is realized.
The hydroxy pinacolone retinoic acid ester solution is good in safety, free of cytotoxicity and good in skin permeability. In addition, the preparation process is simple, the operation is convenient, and the anti-aging cream has good anti-aging effect and no adverse reaction when being applied to skin external preparations, especially anti-aging essences.
Drawings
In order to more clearly illustrate the technical solutions of the embodiments of the present invention, the drawings required in the embodiments will be briefly described below, it should be understood that the following drawings only illustrate some embodiments of the present invention and therefore should not be considered as limiting the scope, and those skilled in the art can also obtain other related drawings based on the drawings without inventive efforts.
FIG. 1 is a solution state diagram of HPR solution B in example 1;
FIG. 2 is a diagram showing the state in comparative example 3 in which HPR was prepared with a conventional solvent and then added to water.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention will be clearly and completely described below. The examples, in which specific conditions are not specified, were conducted under conventional conditions or conditions recommended by the manufacturer. The reagents or instruments used are not indicated by the manufacturer, and are all conventional products available commercially.
The hydroxy pinacolone retinoic acid ester solution, the preparation method thereof, and the external preparation for skin provided by the present application will be specifically described below.
The inventor proposes that: the key reason for the difficulty in using the hydroxy pinacolone retinoic acid ester in aqueous cosmetics, especially transparent essence cosmetics in the prior art is that the hydroxy pinacolone retinoic acid ester is insoluble in water and not easily soluble in ester, and is easily separated out in a formula once contacting a water phase, so that the phenomena of product instability, low skin absorption and utilization rate and the like are caused.
Based on this, the present application creatively proposes a hydroxy pinacolone retinoic acid ester solution, which can stabilize the hydroxy pinacolone retinoic acid ester in aqueous cosmetics, especially clear essential cosmetics.
The hydroxy pinacolone retinoic acid ester solution is prepared from the following raw materials in percentage by weight: 4.5-5.5% of hydroxy pinacolone retinate, 1.8-2.2% of artificial cell membrane, 10-18% of coconut oil alcohol-caprylate/caprate, 4.0-12.0% of caprylic/capric triglyceride and 38.0-45.0% of isononyl isononanoate, and the balance of caprylic/capric glyceride.
The coconut oil alcohol-caprylate/caprate has a certain dissolving effect on hydroxy pinacolone retinoic acid ester and a certain emulsifying effect on hydroxy pinacolone retinoic acid ester. And then combined with an artificial cell membrane, the hydroxy pinacolone retinoic acid ester can be effectively dissolved and uniformly and stably dispersed in an oil phase system formed by caprylic/capric triglyceride, isononyl isononanoate and caprylic/capric triglyceride.
In the solution of hydroxyppinacolone retinoic acid ester, hydroxyppinacolone retinoic acid ester is supported in a bilayer layer of an artificial cell membrane. The structure can ensure that the hydroxy pinacolone retinoic acid ester can stably exist in a water-soluble system or an oil-soluble system.
In the present application, the artificial cell membrane is preferably polyquaternium-51.
Polyquaternary ammonium salt-51 is also called methyl propionyl oxyethyl phosphorylcholine-n-butyl methacrylate, and is a copolymer composed of 2-methyl acryloyl hydroxyethyl phosphatidyl choline and monomomer hydrophobic butyl methacrylate. The polyquaternium-51 has an amphiphilic phospholipid structure the same as that of a human cell membrane, has the film forming effect of a hydrated gel membrane of a phospholipid polymer and the binding effect of the butyl methacrylate on lipophilic substances generated by hydrophobic groups, and can effectively load the hydroxy pinacolone retinoic acid ester in a bilayer layer under the coordination effect of coconut oil alcohol-caprylate/caprate.
The polyquaternium-51 can also play a role of a humectant and a film-forming agent in cosmetics, and after the corresponding cosmetics are smeared on the surface of skin, a biological film similar to a horny layer can be formed, which is equivalent to providing one more barrier for the skin, and meanwhile, the polyquaternium-51 has the functions of helping the horny layer to repair and moisturize, and can improve the rough state of the skin and smoothen and smooth the skin.
The compatibility of the caprylic acid/capric acid triglyceride, isononyl isononanoate and caprylic acid/capric acid triglyceride with the polyquaternium-51 and the hydroxy pinacol retinoic acid ester is moderate, so that the hydroxy pinacol retinoic acid ester can form a completely transparent stable solution and a skin external preparation.
For reference, the specific amount of hydroxy pinacolone retinoic acid ester used herein may be 4.5%, 4.6%, 4.7%, 4.8%, 4.9%, 5.0%, 5.1%, 5.2%, 5.3%, 5.4%, or 5.5%, etc., or may be any other value within the range of 4.5-5.5%.
The specific amount of the artificial cell membrane may be 1.8%, 1.85%, 1.9%, 1.95%, 2.0%, 2.05%, 2.1%, 2.15%, 2.2%, or the like, or may be any other value within the range of 1.8 to 2.2%.
The specific amount of coco caprylate/caprate may be 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, etc., or any other value within the range of 10-18%.
The caprylic/capric triglyceride may be used in a specific amount of 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, etc., or may be any other value within the range of 4.0-12.0%.
Isononyl isononanoate can be used in a specific amount of 38%, 39%, 40%, 41%, 42%, 43%, 44%, or 45%, etc., or can be used in any other amount within the range of 38.0 to 45.0%.
In the application, hydroxy pinacolone retinoic acid ester is loaded in a bilayer molecular layer of an artificial cell membrane under the auxiliary action of coconut oil alcohol-caprylic acid ester/capric acid ester according to a reasonable proportion, and then dissolved in an oil phase formed by caprylic acid/capric acid triglyceride, isononyl isononanoate and caprylic acid/capric acid glyceride according to a specific proportion, so that a clear and transparent solution is prepared, and the convenience in formula application is realized. The obtained hydroxy pinacolone retinoic acid ester solution has excellent skin permeability, is applied to skin external preparations such as anti-aging essence, and can realize anti-aging and skin-care (such as moisturizing, anti-wrinkle, nourishing, skin firming and the like) effects.
Further, the above-mentioned hydroxy pinacolone retinoic acid ester solution may further comprise 0.4-1% of an antioxidant, in terms of the same weight percentage as hydroxy pinacolone retinoic acid ester. Under the condition, the dosage of the caprylic/capric glycerides is 100 percent minus the weight percentage of the hydroxy pinacolone retinoic acid ester, the artificial cell membrane, the coconut oil alcohol-caprylic/capric acid ester, the caprylic/capric triglyceride and the isononyl isononanoate.
For reference, the antioxidant is an oil soluble antioxidant, such as tocopherol acetate.
The antioxidant effect of the hydroxy pinacolone retinoic acid ester solution can be improved by adding the oil-soluble antioxidant.
In the specific preparation process, other components which do not affect the solubility and stability of the hydroxy pinacolone retinoic acid ester can be added to the raw materials for preparing the hydroxy pinacolone retinoic acid ester solution according to the need.
Correspondingly, the application also provides a preparation method of the hydroxy pinacolone retinoic acid ester solution, which comprises the following steps: mixing the preparation raw materials according to the proportion.
Specifically, the preparation method comprises the following steps:
mixing the artificial cell membrane, the hydroxy pinacolone retinoic acid ester solution and coconut oil alcohol-caprylate/caprate to obtain a first mixture;
mixing caprylic/capric triglyceride, isononyl isononanoate and caprylic/capric triglyceride to obtain a second mixture;
mixing the first mixed material and the second mixed material.
When the preparation raw materials contain the antioxidant, the mixture of the first mixture and the second mixture is mixed with the antioxidant.
Wherein the artificial cell membrane, hydroxy pinacolone retinoic acid ester and coconut oil alcohol-caprylate/caprate can be mixed in a stirring pot at 40-60 deg.C, such as 40 deg.C, 45 deg.C, 50 deg.C, 55 deg.C or 60 deg.C. The mixing time can be 25-40min, such as 25min, 30min, 35min or 40 min.
The first mixture and the second mixture are mixed, namely the second mixture is added into the first mixture under the condition of heat preservation of the first mixture, and the mixture is continuously stirred at the heat preservation state until the second mixture is completely dissolved to form a clear and transparent solution.
And the step of adding the antioxidant is to cool the mixed solution of the first mixture and the second mixture to room temperature, then add the antioxidant, and stir the mixture evenly.
The preparation method has simple process and convenient operation, and can be used for industrial preparation.
In addition, the application also provides a skin external agent, and the preparation raw material of the skin external agent comprises the hydroxy pinacolone retinoic acid ester solution.
For reference, the skin external preparation may be a cosmetic, a pharmaceutical skin external preparation, or the like.
The cosmetic is water-containing cosmetic such as essence cosmetic or gel cosmetic.
In some specific embodiments, the hydroxy pinacolone retinoic acid ester solution is used for preparing an anti-aging essence or an anti-aging gel, and the corresponding product has good anti-aging and skin-care effects and no adverse reaction.
The features and properties of the present invention are described in further detail below with reference to examples.
Example 1
This example provides three HPR solutions, HPR A, HPR solution B and HPR solution C, the components of the three artificial cell membrane-coated HPR solutions are shown in Table 1, and the preparation methods are all referred to the following steps:
step (1): adding polyquaternium-51, hydroxy pinacolone retinoic acid ester and coconut oil alcohol-caprylate/caprate into a stirring pot according to the proportion in the table 1, heating to 40-60 ℃, uniformly stirring for 30min to form a first mixture, and preserving heat for later use;
step (2): adding caprylic acid/capric acid glycerides, caprylic acid/capric acid triglyceride and isononyl isononanoate into the first mixture in the step (1) according to the proportion in the table 1, and continuously stirring at a constant temperature until the materials are completely dissolved to form a clear transparent solution (a second mixture);
(3) cooling to room temperature, adding antioxidant tocopheryl acetate, and stirring to obtain HPR solution.
TABLE 1 composition ingredient Table
All three HPR solutions prepared in this example were in the form of clear solutions, wherein the solution state of HPR solution B is shown in fig. 1.
Comparative example 1
This comparative example provides three HPR comparative solutions, comparative solution a, comparative solution B and comparative solution C, having the compositions shown in table 2, and prepared according to the examples.
TABLE 2 composition ingredient Table
The three HPR contrast solutions prepared in this comparative example were all opaque, turbid solutions and could not form a clear, transparent state.
Thus illustrating that: the proportion of the components has a remarkable influence on the final state of the HPR solution, and the HPR solution cannot be in a transparent and clear state due to improper proportion of the components.
Comparative example 2
In this comparative example, the caprylic/capric glycerides of HPR solution B in table 1 were replaced with squalane in equal amounts, and the other ingredients were not changed, and the HPR solution obtained by the preparation method according to example 1 could not be in a transparent and clear state.
Comparative example 3
In the comparative example, a conventional solvent dissolving mode is adopted, other components except for the hydroxy pinacolone retinoic acid ester in the HPR solution B in the table 1 are replaced by ethanol in an equal amount, namely 5% of hydroxy pinacolone retinoic acid ester is dissolved in ethanol, the obtained HPR solution is in a transparent and clear state, the obtained HPR is added into water to generate turbidity (shown in figure 2), and hydroxy pinacolone retinoic acid ester oil drops are separated out, so that when the solution prepared by the conventional solvent for HPR is added into a product, the solvent around the HPR is reduced after the conventional solvent is dissolved in the water, and the HPR is directly contacted with the water, so that the solution is easy to separate out and generates turbidity. When the solution of HPR prepared in example 1 was added to the product, the HPR did not directly contact water and no precipitation occurred in the product.
Example 2
Preparation of anti-aging essence
The artificial cell membrane-wrapped HPR solution B prepared according to example 1 and the comparative solution B prepared according to comparative example 1 were used for the preparation of the anti-aging essence and the comparative essence, respectively. The anti-aging essence is prepared from the following main components (shown in table 3) in percentage by mass, wherein the HPR solution B is replaced by the comparative solution B in the comparative essence, and other components are completely the same.
TABLE 3 anti-aging essence composition table
The preparation method comprises the following steps:
mixing and heating the component A to 75 ℃ until the component A is completely dissolved;
adding the component B, and continuously stirring at 75 ℃ until the component B is completely dissolved to form an AB mixture;
cooling to 50 deg.C, slowly adding component C into the AB mixture under stirring, homogenizing to completely uniform, adding component D, starting homogenizing, and stirring to completely uniform;
cooling to 40 deg.C, sequentially adding component E, homogenizing, and stirring.
The results showed that the anti-aging essence was a translucent solution, while the comparative essence was turbid.
Example 3
Preparation of anti-aging gel
The artificial cell membrane-wrapped HPR solution B prepared according to example 1 was used for the preparation of anti-aging gel prepared from the following main components (as shown in table 4) in mass%.
TABLE 4 anti-aging gel ingredient table
The preparation method comprises the following steps:
pre-homogenizing, mixing and stirring the component C uniformly;
adding the component A into a vacuum emulsifying pot, and stirring until the component A is uniformly dispersed;
adding the mixed component B, starting homogenization until the mixture is completely uniform, adding the component D, and uniformly mixing;
and adding the mixed component A, component B and component D into the premixed component C, homogenizing, and stirring to be completely uniform.
The resulting age gel was in a translucent state.
Test example 1
Product stability testing
1) The anti-aging essence prepared in example 2 was subjected to a heat-resistant and cold-resistant stability test.
The heat resistance test conditions were: keeping the temperature at 45 +/-1 ℃ and keeping the temperature away from the sun for 30 days;
the cold resistance test conditions are as follows: keeping the temperature at minus 20 +/-1 ℃ and keeping away from light for 30 days;
compared with the anti-aging essence prepared in the example 2, the anti-aging essence has no obvious change in product odor, no precipitate is separated out, and the heat-resistant color becomes slightly light, which indicates that the product stability is good.
2) The age resistant gel prepared as in example 3 was tested for heat resistance, cold resistance, alternating and light stability.
The heat-resistant and cold-resistant test conditions are the same as the anti-aging essence;
the alternating test conditions were: keeping the temperature at minus 20 ℃ for 3.5 days, changing the temperature at 45 ℃ for 3.5 days, and keeping out of the sun;
the illumination test conditions were: and (4) illuminating a constant temperature and humidity test chamber (1.47X 106 Lux. hr) for 7 d.
Compared with the anti-aging gel prepared in example 3, the anti-aging gel has no obvious change in product odor, no precipitation in cold resistance and slightly deepened heat resistance and illumination color under the normal temperature condition, and the product stability is good.
Test example 2
Product safety testing
1) Guinea pig multiple (acute) skin irritation tests were performed according to the anti-aging essence prepared in example 2, continuously applied for 7 days under the test conditions of laboratory temperature: relative humidity at 20-24 ℃: 60-70%.
The results showed that the number of erythema was 0, the number of edema was 0, the stimulation response integral was 0, and the stimulation intensity was graded as: has no irritation.
2) The anti-aging gel prepared as in example 3 was applied to guinea pigs for 7 consecutive days in multiple (acute) skin irritation tests under the conditions of laboratory temperature: relative humidity at 20-24 ℃: 60-70%.
The results showed that the number of erythema was 0, the number of edema was 0, the stimulation response integral was 0, and the stimulation intensity was graded as: has no irritation.
Test example 3
Anti-aging essence efficacy test
The anti-aging essence product prepared in example 2 (oshi diffuse pearl muscle activity endowing elastic and tender essence) was used by adult volunteers under normal conditions for 8 weeks to evaluate the effects of anti-wrinkle, firming and moisturizing of the product.
The using method comprises the following steps: the product is used once every morning and evening, 2 pumps are used for each time, the product is uniformly smeared on the whole face until the product is completely absorbed, and the product is also smeared around eyes.
Subject: age 35 to 60, healthy women; asians (china); the skin is loose, the forehead, the glabella, the canthus, the under-eye and the nasolabial folds of the face have visible wrinkles, and the clinical score is 3-6 grade; the moisture content of the stratum corneum in the cheek region of the face was < 50 c.u.; 33 persons were actually recruited, and 33 persons were available data.
And (3) test period: before use of the sample (Day0), after use of the sample for 28 days (Day28), and after use of the sample for 56 days (Day 56).
1) Image acquisition: VISIA is used for facial image acquisition and analysis of skin wrinkles and pores, with smaller feature counts indicating improved skin, smaller scores indicating improved skin, and larger percentile values indicating improved skin. Primos CR was used for facial image acquisition and skin wrinkle analysis, and smaller values indicated improvement of skin wrinkles. Visioscan VC 20plus is used for facial image acquisition and skin surface texture analysis, and the larger the value of skin roughness SEr, the smaller the value of skin smoothness SEsm, the improved skin smoothness, and the smaller the value of skin wrinkle Sew, the lighter the skin wrinkle. The skin ultrasonic instrument Ultrascan UC22 is used for facial image acquisition and analysis of thickness and density of dermis layer of skin, and the larger value indicates improvement of skin.
2) Skin elasticity: the skin elasticity tester Cutomer dual MPA 580 detects skin elasticity, and the larger the value is, the skin elasticity is improved.
3) Skin firming: the skin elasticity tester Cutomer dual MPA 580 detects skin firmness, and the smaller the value, the more improvement of skin firmness is shown.
4) Skin glossiness: skin gloss was measured by a skin gloss meter Glossimeter GL200, and a larger value indicates an improvement in skin gloss.
5) Moisture content of skin stratum corneum: a skin moisture determinator Corneometer CM825 detects the moisture content of the stratum corneum, and the larger the measured value is, the higher the moisture content of the stratum corneum is.
6) Clinical evaluation by dermatologist: wrinkle scoring criteria: rating scale 0 to 9; pore scoring criteria: rating scale 0 to 9; compactness scoring criteria: the 0 to 9 rating scale (0 ═ skin is very tight and has significant resistance to tension or pressure, and 9 ═ skin is not tight (skin laxity) and is easily deformable by stretching); smoothness scoring criteria: rating scale 0 to 9.
Data results were statistically analyzed using SPSS Statistics 25.0. Carrying out normal analysis on the measured data, and if the data is in normal distribution, carrying out statistical analysis by adopting a T test method; and if the data is in abnormal distribution, performing statistical analysis by adopting a rank sum test method. The grade data is statistically analyzed by a rank sum test. Statistical methods significance levels were all P < 0.050.
The results show that after the test product is used for 28 days, the wrinkle length of the forehead area is obviously improved by-7.37 percent compared with the basic value, the wrinkle depth, the wrinkle length, the wrinkle area and the wrinkle volume of the glabellar area are respectively-8.73 percent, -10.05 percent, -7.18 percent and-12.27 percent compared with the basic value, the wrinkle depth and the wrinkle volume of the canthus area are obviously improved by-10.60 percent and-10.01 percent respectively compared with the basic value, the wrinkle number, the wrinkle depth, the wrinkle length, the wrinkle area and the wrinkle volume of the under-eye area are respectively-8.16 percent, -9.08 percent, -18.27 percent, -12.48 percent and-16.54 percent compared with the basic value, the wrinkle depth, the wrinkle length and the wrinkle volume of the nasolabial fold area are respectively-5.19 percent, -5.39 percent and-8.94 percent respectively compared with the basic value, the wrinkle volume, the wrinkle area and the wrinkle length are obviously improved compared with the basic value, and the clinical evaluation mean value of the wrinkles is obviously improved compared with the basic value. After 56 days, the number of wrinkles, the wrinkle depth, the wrinkle length, the wrinkle area and the wrinkle volume of forehead, glabella and under-eye regions are respectively-9.09% to-24.28% compared with the basic value, the wrinkle depth, the wrinkle length and the wrinkle volume of canthus regions are respectively-15.96%, -7.79% and-9.93% compared with the basic value, the wrinkles, the wrinkle depth, the wrinkle length, the wrinkle area and the wrinkle volume of nasolabial sulcus regions are respectively-6.10%, -13.37%, -8.43% and-12.96% compared with the basic value, the wrinkles are remarkably improved, and the clinical evaluation average value of the wrinkles is remarkably improved compared with the basic value. The test results show that: under the test conditions, the test product had an anti-wrinkle effect.
After the test product is used for 28 days, the skin elasticity R2 and R7 values of the test area are respectively increased by 7.31 percent and 12.96 percent compared with the basic value, the improvement is remarkable, and the skin tightness F4 is remarkably improved by-5.14 percent compared with the basic value. After 56 days, the skin elasticity values R2, R5 and R7 of the test area are respectively increased by 12.18%, 10.58% and 20.56% compared with the basic value, and the skin tightness F4 is obviously improved by-7.00% compared with the basic value. The test results show that: under this test condition, the test product had a firming effect.
After 28 days and 56 days of test product use, the moisture content of the stratum corneum in the test area was increased by 27.25% and 47.80% respectively, which was a significant improvement, and the above test results show that: under the test conditions, the test product had efficacy in moisturizing.
After the test product is used for 28 days, the glossiness of the test area is increased by 5.99 percent compared with the basic value, the glossiness is remarkably improved, the clinical evaluation mean value of the glossiness is remarkably improved compared with the basic value, the roughness is improved by 11.54 percent compared with the basic value, and the smoothness is remarkably improved compared with the basic value. After 56 days, the glossiness of the test area is increased by 11.91 percent compared with the basic value, the glossiness clinical evaluation mean value is obviously improved compared with the basic value, and the smoothness clinical evaluation mean value is obviously improved compared with the basic value. The test results show that: under the test conditions, the test product has nourishing efficacy.
Test example 4
Anti-aging gel efficacy test
Over 30 volunteers, females between 25-50 years of age, mean age 40.9 ± 7.6 years of age, 30 valid samples were recruited. The anti-aging gel product (oshi-margarita skin-active energizing and firming essence gel) prepared according to example 3 was evaluated for its moisturizing, anti-wrinkle, firming efficacy by leaving the consumer product for 14 days.
One capsule is used after cleaning the face at night every day, the capsule is torn open, all essences are evenly smeared on the whole face, and the whole face is gently massaged until the essences are absorbed, so that the periphery of eyes is avoided. No adverse events occurred in this study.
Product use effect investigation: a score of 9 was used, with 1 corresponding to strong objection and 9 corresponding to strong consent. And (3) calculating whether the occurrence probability of TOP4 (score >5 points) and BOT5 (score less than or equal to 5 points) is different from the specified test proportion by adopting binomial test, wherein the test proportion is 0.50.
TABLE 5 Consumer investigation of changes in skin condition
As can be seen from table 5: compared with the prior sample, the problems of dead skin on the face, dry and tight skin, rough skin, canthus wrinkles, fine lines under eyes, forehead raised lines, facial glabellar lines, facial texture lines, skin fine lines, large pores and skin looseness are obviously improved for 30 subjects immediately after the sample is used; after 14 days of use of the sample, 30 subjects showed significant improvement in the problems of dead skin on the face, dry and tight skin, skin gloss, rough skin, canthus wrinkles, fine lines under the eyes, forehead raising lines, eyebrow lines, facial ordinance lines, fine lines, and loose skin, compared to before use.
To sum up, the hydroxy pinacolone retinoic acid ester solution provided by the application is clear and transparent, good in safety, free of cytotoxicity and good in skin permeability. In addition, the preparation process is simple, the operation is convenient, and the anti-aging cream has good anti-aging effect and no adverse reaction when being applied to skin external preparations, especially anti-aging essences.
The above is only a preferred embodiment of the present invention, and is not intended to limit the present invention, and various modifications and changes will occur to those skilled in the art. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (10)
1. The hydroxy pinacolone retinoic acid ester solution is characterized in that the hydroxy pinacolone retinoic acid ester solution is prepared from the following raw materials in percentage by weight: 4.5-5.5% of hydroxy pinacolone retinate, 1.8-2.2% of artificial cell membrane, 10-18% of coconut oil alcohol-caprylate/caprate, 4.0-12.0% of caprylic/capric triglyceride and 38.0-45.0% of isononyl isononanoate, and the balance of caprylic/capric glyceride.
2. The hydroxy pinacolone retinoic acid ester solution of claim 1, wherein the artificial cell membrane is polyquaternium-51.
3. The hydroxyppinacolone retinoic acid ester solution of claim 1 or 2, wherein the raw material for preparation further comprises 0.4-1% of an antioxidant in the same weight percentage as the hydroxyppinacolone retinoic acid ester.
4. The hydroxyppinacolone retinoic acid ester solution of claim 3, wherein the antioxidant is an oil-soluble antioxidant.
5. The hydroxyppinacolone retinoic acid ester solution of claim 4, wherein the antioxidant is tocopherol acetate.
6. The process for the preparation of a solution of hydroxyppinacolone retinoic acid ester according to any of claims 1-5, comprising the steps of: mixing the preparation raw materials according to the proportion.
7. The method of claim 6, wherein preparing comprises:
mixing said artificial cell membrane, said hydroxy pinacolone retinate and said coco-caprylate/caprate to obtain a first mixture;
mixing the caprylic/capric triglyceride, the isononyl isononanoate and the caprylic/capric triglyceride to obtain a second mixture;
mixing the first mix material with the second mix material.
8. The method of claim 7, wherein the mixture of the first and second mixes is mixed with the antioxidant when the antioxidant is present in the preparation stock.
9. The method of claim 8, wherein the artificial cell membrane, the hydroxy pinacolone retinate and the coco caprylate/caprate are mixed with stirring at 40-60 ℃;
preferably, the mixing time is 25-40 min.
10. An external preparation for skin, which is prepared from a raw material comprising the hydroxy pinacolone retinoic acid ester solution of any one of claims 1 to 5;
preferably, the external preparation for skin comprises a cosmetic;
preferably, the cosmetic is a water-containing cosmetic;
preferably, the aqueous cosmetic is an essence-based cosmetic or a gel-based cosmetic.
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| CN114588067A (en) * | 2022-03-18 | 2022-06-07 | 上海世领制药有限公司 | Hydroxy pinacolone retinoic acid ester high-oil permeation-promoting carrier, preparation method and application thereof |
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| KR20100103173A (en) * | 2009-03-13 | 2010-09-27 | (주)아모레퍼시픽 | Hair cosmetic composition |
| CN114588067A (en) * | 2022-03-18 | 2022-06-07 | 上海世领制药有限公司 | Hydroxy pinacolone retinoic acid ester high-oil permeation-promoting carrier, preparation method and application thereof |
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