CN115317398B - Ionic liquid collagen preparation and preparation method and application thereof - Google Patents
Ionic liquid collagen preparation and preparation method and application thereof Download PDFInfo
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- CN115317398B CN115317398B CN202210885842.4A CN202210885842A CN115317398B CN 115317398 B CN115317398 B CN 115317398B CN 202210885842 A CN202210885842 A CN 202210885842A CN 115317398 B CN115317398 B CN 115317398B
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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
- A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
- A61K8/65—Collagen; Gelatin; Keratin; Derivatives or degradation products 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
- A61K8/30—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
- A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
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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
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
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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
- A61Q19/10—Washing or bathing preparations
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- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
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Abstract
The invention discloses an ionic liquid collagen preparation and a preparation method and application thereof. The preparation method comprises the following steps: providing a L-carnitine citric acid ionic liquid, wherein the structural formula of the L-carnitine citric acid ionic liquid is as follows:mixing and stirring the L-carnitine citrate ionic liquid and the collagen, and sequentially homogenizing, filtering, dialyzing and concentrating to obtain the ionic liquid collagen preparation. The invention adopts the L-carnitine citrate ionic liquid to deliver the collagen, so that the defects of higher toxicity and difficult metabolism of the traditional ILs can be overcome while the excellent performance of the L-carnitine citrate ionic liquid is maintained. The introduction of the L-carnitine and the citric acid can realize the effects of antioxidation, exfoliating and the like, realize the high bioavailability of the preparation at a lower concentration, and endow continuous administration and slow release effects. The ionic liquid collagen preparation has the characteristics of quick absorption, high bioavailability, quick effect, stable property and the like.
Description
Technical Field
The invention relates to the field of protein preparations, in particular to an ionic liquid collagen preparation and a preparation method and application thereof.
Background
Collagen has a triple-helical fibrous structure, is the most abundant protein in the body, and is the main component of bones, skin, muscles, tendons and cartilage. With age, collagen production in the body gradually decreases. At the same time, collagen fibers are damaged due to the effects of sun exposure, smoking, excessive drinking and lack of sleep and exercise, and finally wrinkles appear on the skin surface. Collagen is commonly used in skin creams and essences. However, collagen does not naturally occur on the skin surface and is difficult to supplement by means of transdermal delivery due to the large collagen fibers. Thus, the topical application has limited effectiveness. Oral collagen supplements in the form of pills, powders and certain foods are believed to be more effectively absorbed by the human body, and collagen bioavailability is limited and not targeted due to the effects of gastrointestinal digestion and the liver "first pass effect". The injection is used, the product has complex process and high price, and can cause pain to patients, thus having poor compliance. Therefore, there is a need to develop collagen preparations in different dosage forms.
The Ionic Liquids (ILs) have the characteristics of low volatility, high stability, high conductivity, nonflammability and the like, and the characteristics are in high accord with the pharmaceutical concept of green chemistry. Besides, ILs can be used as active ingredients of medicines to form a novel API-ILs drug delivery system. Research shows that traditional imidazole ILs can change membrane permeability by disturbing cell membrane structure, thereby realizing the transcellular transport of medicines. However, such ILs have been found to be susceptible to oxidative damage and have chronic toxicity.
Accordingly, the prior art is still in need of improvement and development.
Disclosure of Invention
In view of the shortcomings of the prior art, the invention aims to provide an ionic liquid collagen preparation, a preparation method and application thereof, and aims to solve the problems that ILs have high toxicity and are not easy to metabolize in the existing ILs delivery medium.
The technical scheme of the invention is as follows:
in a first aspect of the present invention, there is provided a method for preparing an ionic liquid collagen preparation, comprising the steps of:
providing a L-carnitine citric acid ionic liquid, wherein the structural formula of the L-carnitine citric acid ionic liquid is as follows:
mixing and stirring the L-carnitine citrate ionic liquid and the collagen, and sequentially homogenizing, filtering, dialyzing and concentrating to obtain the ionic liquid collagen preparation.
Optionally, the preparation method of the L-carnitine citric acid ionic liquid comprises the following steps:
respectively adding the L-carnitine salt and the citrate into a solvent to obtain a L-carnitine salt solution and a citrate solution;
and mixing the L-carnitine salt solution and the citrate solution, stirring under preset conditions, filtering, concentrating and drying to obtain the L-carnitine citric acid ionic liquid.
Optionally, the L-carnitine salt is one or more of L-carnitine hydrochloride, L-carnitine sulfate and L-carnitine bisulfate;
the citrate is one or more of sodium citrate and calcium citrate;
the solvent is one or more of water, ethanol, isopropanol and n-butanol;
the molar ratio of the L-carnitine salt to the citrate is 1:0.1-1:8.
Optionally, the preset condition includes: stirring under a mixed atmosphere of carbon dioxide and nitrogen, wherein the volume ratio of the carbon dioxide to the nitrogen is 99:1-99:10, and the pressure of the mixed atmosphere is 0.1-100 MPa.
Optionally, the mass ratio of the L-carnitine citrate ionic liquid to the collagen is 10:1-100:1.
Optionally, the step of mixing the l-carnitine citrate ionic liquid and collagen specifically includes: and adding the collagen into the L-carnitine citric acid ionic liquid within 10 to 60 minutes under the water area condition of 50 to 300rpm stirring speed and minus 5 to 40 ℃.
Optionally, the stirring time is 1-10 hours;
the conditions of homogenization include: the pressure is 0-80 MPa, the flow is 30-60L/h, and the homogenization times are 1-3 times.
Optionally, the conditions of the dialysis include: the time is 1-10 hours, and the dialysis times are 1-3 times.
In a second aspect of the present invention, an ionic liquid collagen preparation is provided, wherein the ionic liquid collagen preparation is prepared by the preparation method of the ionic liquid collagen preparation.
In a third aspect of the invention, the application of the ionic liquid collagen preparation in preparing cosmetics is provided.
The beneficial effects are that: the invention adopts the L-carnitine citrate ionic liquid to deliver the collagen, so that the defects of higher toxicity and difficult metabolism of the traditional ILs can be overcome while the excellent performance of the L-carnitine citrate ionic liquid is maintained. Meanwhile, due to the introduction of the L-carnitine and the citric acid in the L-carnitine citric acid ionic liquid, the effects of antioxidation, exfoliating and the like can be realized, the high bioavailability of the preparation at a lower concentration is realized, and the effects of continuous administration and slow release are given. The ionic liquid collagen preparation of the invention is applied to cosmetics and has the characteristics of quick absorption, high bioavailability, quick effect, stable property and the like.
Drawings
Fig. 1 is a schematic flow chart of a preparation method of an ionic liquid collagen preparation according to an embodiment of the present invention;
FIG. 2 is an NMR hydrogen spectrum of L-carnitine citrate ionic liquid in example 1;
FIG. 3 is an FTIR spectrum of the L-carnitine citrate ionic liquid of example 1;
FIG. 4 is a fluorescence sectional view showing the transdermal effect of the collagen preparation of comparative example 1;
FIG. 5 is a fluorescence sectional view showing the transdermal effect of the ionic liquid collagen preparation in example 1;
fig. 6 is a statistical graph of permeation efficiencies of example 1 and comparative example 1.
Detailed Description
The invention provides an ionic liquid collagen preparation, a preparation method and application thereof, and aims to make the purposes, technical schemes and effects of the invention clearer and more definite, and the invention is further described in detail below. It should be understood that the specific embodiments described herein are for purposes of illustration only and are not intended to limit the scope of the invention.
The embodiment of the invention provides a preparation method of an ionic liquid collagen preparation, as shown in fig. 1, comprising the following steps:
s1, providing a L-carnitine citric acid ionic liquid, wherein the structural formula of the L-carnitine citric acid ionic liquid is as follows:
s2, mixing the L-carnitine citrate ionic liquid with collagen, stirring, and sequentially homogenizing, filtering, dialyzing and concentrating to obtain an ionic liquid collagen preparation.
In this example, the l-carnitine citrate ionic liquid combines with collagen through hydrogen bond interaction and electrostatic attraction to form a supramolecular structure (i.e., an ionic liquid collagen preparation). The collagen is delivered by adopting the L-carnitine citrate ionic liquid, so that the defects of high toxicity and difficult metabolism of the traditional ILs can be overcome while the excellent performance of the L-carnitine citrate ionic liquid is maintained. Meanwhile, due to the introduction of the L-carnitine and the citric acid in the L-carnitine citric acid ionic liquid, the effects of antioxidation, exfoliating and the like can be realized, the high bioavailability of the preparation at a lower concentration is realized, and the effects of continuous administration and slow release are given.
The ionic liquid collagen preparation has the characteristics of quick absorption, high bioavailability, quick effect and the like, and can overcome the defects of high irritation, poor compliance and the like of the existing protein preparation such as oral digestion and first pass effect.
In step S1, in one embodiment, the preparation method of the l-carnitine citrate ionic liquid includes the steps of:
s11, respectively adding the L-carnitine salt and the citrate into a solvent to obtain a L-carnitine salt solution and a citrate solution;
and S12, mixing the L-carnitine salt solution and the citrate solution, stirring under preset conditions, filtering, concentrating and drying to obtain the L-carnitine citric acid ionic liquid.
According to the preparation method, the salt of the precursor is used as a raw material, and the preparation is carried out under the pressure condition, so that the formation of the L-carnitine citrate ionic liquid can be promoted, and the stability of the L-carnitine citrate ionic liquid can be improved.
In step S11, in one embodiment, the l-carnitine salt is one or more of l-carnitine hydrochloride, l-carnitine sulfate, l-carnitine bisulfate, etc., but is not limited thereto.
In one embodiment, the citrate is one or more of sodium citrate, calcium citrate, and the like, but is not limited thereto.
In one embodiment, the solvent is one or more of water, ethanol, isopropanol, n-butanol, etc., but is not limited thereto.
In one embodiment, the molar ratio of the L-carnitine salt to the citrate is from 1:0.1 to 1:8.
In step S12, in one embodiment, the preset condition includes: stirring under a mixed atmosphere of carbon dioxide and nitrogen, wherein the volume ratio of the carbon dioxide to the nitrogen is 99:1-99:10. Namely, preparing the L-carnitine citric acid ionic liquid under the mixed atmosphere of carbon dioxide and nitrogen. Further, the pressure of the mixed atmosphere is 0.1-100 MPa.
In one embodiment, the stirring temperature is 10 to 80 ℃ (e.g., 10 ℃, 20 ℃, 30 ℃, 40 ℃, 50 ℃, 60 ℃, 70 ℃, 80 ℃, etc.), and the stirring time is 1 to 24 hours (e.g., 1 hour, 2 hours, 5 hours, 8 hours, 10 hours, 14 hours, 17 hours, 20 hours, 22 hours, 24 hours, etc.). That is, the reaction is carried out at 10 to 80℃for 1 to 24 hours, and sufficient reaction can be ensured under such conditions.
In one embodiment, the concentration is performed by distillation under reduced pressure.
In one embodiment, the drying is performed by lyophilization.
In step S2, in one embodiment, the mass ratio of the l-carnitine citrate ionic liquid to the collagen is 10:1-100:1, for example, 10:1, 20:1, 30:1, 40:1, 50:1, 60:1, 70:1, 80:1, 90:1, 100:1, etc., and other specific values within the numerical range may be selected, which will not be described in detail herein. The added amount of the L-carnitine citrate ionic liquid is further reduced or further increased, so that the ionic liquid collagen preparation is unstable in property. Further, the mass ratio of the L-carnitine citrate ionic liquid to the collagen is 10:1-30:1, so that the stability of the properties of the ionic liquid collagen preparation can be effectively ensured.
In one embodiment, the step of mixing the l-carnitine citrate ionic liquid and collagen specifically comprises: and slowly adding the collagen into the L-carnitine citric acid ionic liquid within 10 to 60 minutes under the water area condition of 50 to 300rpm stirring speed and minus 5 to 40 ℃. Under the condition, the collagen is added, so that the aggregation of the collagen can be avoided, and the collagen is fully wrapped. The water temperature can avoid the destruction of collagen caused by high temperature. Under the stirring and time conditions, the full mixing of the L-carnitine citrate ionic liquid and the collagen can be promoted, the energy consumption is reasonably controlled, and the equipment requirement is reduced.
In one embodiment, the stirring time is 1-10 hours, for example, 1 hour, 2 hours, 3 hours, 4 hours, 5 hours, 6 hours, 7 hours, 8 hours, 9 hours, 10 hours, etc., and other specific values within the numerical range may be selected, which will not be described in detail herein. Under the time condition, the energy consumption can be reasonably controlled, and the equipment requirement is reduced.
In one embodiment, the homogenizing conditions comprise: the pressure is 0-80 MPa, the flow is 30-60L/h, and the homogenization times are 1-3 times. Under the pressure and flow conditions, the collagen and the L-carnitine citrate ionic liquid can be fully mixed while the energy consumption is reasonably controlled and the equipment requirement is reduced, so that a coating structure is formed.
In one embodiment, the conditions of dialysis include: the time is 1 to 10 hours (e.g., 1 hour, 2 hours, 3 hours, 4 hours, 5 hours, 6 hours, 7 hours, 8 hours, 9 hours, 10 hours, etc.), and the number of times of dialysis is 1 to 3 (e.g., 1 time, 2 times, 3 times). The dialysis step can remove the free L-carnitine citric acid ionic liquid and improve the concentration of the ionic liquid collagen preparation. The dialysis times and time can improve the production efficiency, reasonably control the cost and reduce the loss of raw materials.
In one embodiment, the concentration is performed by distillation under reduced pressure.
In one embodiment, the concentration refers to concentration of the dialysate obtained by dialysis to 1/6-1/3 of the original volume of the dialysate, for example, 1/6, 1/5, 1/4, 1/3, etc., and other specific values within the numerical range may be selected, which will not be described in detail herein.
The embodiment of the invention provides an ionic liquid collagen preparation, which is prepared by adopting the preparation method of the ionic liquid collagen preparation.
The embodiment of the invention provides an application of the ionic liquid collagen preparation in preparing cosmetics.
The invention is further illustrated by the following specific examples.
Example 1
Adding 0.1mol of L-carnitine bisulfate and 0.13mol of calcium citrate into 100mL of ethanol respectively, mixing the two, continuously stirring for 24 hours at 40 ℃ under the carbon dioxide/nitrogen atmosphere with the pressure of 40MPa and the volume ratio of 95/5, fully reacting the two, removing the pressure, filtering, concentrating and drying to obtain the L-carnitine citric acid ionic liquid. And then adding the collagen into the L-carnitine citric acid ionic liquid within 60 minutes at a stirring speed of 150rpm and a water area condition of 30 ℃ according to the mass ratio of the L-carnitine citric acid ionic liquid to the collagen of 20:1, and continuously stirring for 10 hours after the addition is completed. The reaction mixture was then homogenized 3 times under conditions of 30MPa and 30L/h. After filtration, dialysis was carried out 3 times, each for 10 hours. Collecting the dialysate, concentrating the dialysate to 1/3 of the original volume at 50 ℃ under the condition of 0.1mbar, and obtaining the ionic liquid collagen preparation.
Wherein, fig. 2 is the NMR hydrogen spectrum of the l-carnitine citrate ionic liquid in this example, and fig. 3 is the FTIR spectrum of the l-carnitine citrate ionic liquid in this example.
Comparative example 1
Provides pure collagen.
Transdermal effect test:
the ionic liquid collagen preparation prepared in example 1 and the collagen provided in comparative example 1 were subjected to a transdermal effect test, and the specific test method is as follows:
I. skin of back of GF Kunming mouse is used, subcutaneous fat layer and connective tissue are carefully peeled off, washed clean with physiological saline, and placed in physiological saline for standby.
Franz diffusion device with an exposed skin area of 1.13cm 2 Receiving poolThe volume was 15mL.
III, respectively taking an ionic liquid collagen preparation and 1.0mL of collagen to be detected liquid medicine with equal concentration on the surface of skin, adding 15mL of commercial PBS buffer salt solution (pH is approximately 7.4) receiving solution into a receiving tank, and placing the receiving solution into a constant-temperature water bath with the constant temperature of 32+/-0.5 ℃ and the stirring speed of 350r/min.
Test of subcutaneous penetration: and respectively taking 2mL of receiving solution at different time points, wherein each time point is 3 parts in parallel, immediately supplementing 2mL of receiving solution into the receiving tank after sampling, filtering by a microporous filter membrane with the thickness of 0.22 mu m, and freezing for preservation to be tested.
Fig. 4 is a fluorescence sectional view showing the transdermal effect of collagen in comparative example 1, and it is clear from fig. 4 that the active ingredient is trapped by the skin in the simple collagen control group, and collagen hardly penetrates the stratum corneum of the skin.
Fig. 5 is a fluorescence sectional view showing the transdermal effect of the ionic liquid collagen preparation of example 1, and it is apparent from fig. 5 that the active ingredient can penetrate the skin to reach the inner layer junction of the skin in the experimental group of the ionic liquid collagen preparation.
Fig. 6 is a statistical graph of permeation efficiencies of example 1 and comparative example 1, and it is understood from fig. 6 that the l-carnitine citrate ionic liquid can improve the permeation efficiency of collagen, thereby improving the bioavailability thereof.
Example 2
Adding 0.1mol of L-carnitine hydrochloride and 0.1mol of sodium citrate into 50mL of ethanol respectively, mixing the two, continuously stirring for 10 hours at 40 ℃ under the atmosphere of carbon dioxide/nitrogen with the pressure of 80MPa and the volume ratio of 95/5, fully reacting, removing the pressure, filtering, concentrating and drying to obtain the L-carnitine citric acid ionic liquid. And then adding the collagen into the L-carnitine citric acid ionic liquid within 60 minutes at a stirring speed of 100rpm and a water area condition of 30 ℃ according to the mass ratio of the L-carnitine citric acid ionic liquid to the collagen of 20:1, and continuously stirring for 10 hours after the addition is completed. The reaction mixture was then homogenized 3 times under conditions of 30MPa and 30L/h. After filtration, dialysis was carried out 3 times, each for 10 hours. Collecting the dialysate, concentrating the dialysate to 1/3 of the original volume at 50 ℃ under the condition of 0.1mbar, and obtaining the ionic liquid collagen preparation.
In summary, the ionic liquid collagen preparation and the preparation method and application thereof provided by the invention adopt the L-carnitine citrate ionic liquid to deliver collagen, so that the defects of high toxicity and difficult metabolism of the traditional ILs can be overcome while the excellent performance of the L-carnitine citrate ionic liquid is maintained. Meanwhile, due to the introduction of the L-carnitine and the citric acid in the L-carnitine citric acid ionic liquid, the effects of antioxidation, exfoliating and the like can be realized, the high bioavailability of the preparation at a lower concentration is realized, and the effects of continuous administration and slow release are given. The ionic liquid collagen preparation of the invention is applied to cosmetics and has the characteristics of quick absorption, high bioavailability, quick effect, stable property and the like.
It is to be understood that the invention is not limited in its application to the examples described above, but is capable of modification and variation in light of the above teachings by those skilled in the art, and that all such modifications and variations are intended to be included within the scope of the appended claims.
Claims (9)
1. The preparation method of the ionic liquid collagen preparation is characterized by comprising the following steps:
providing a L-carnitine citric acid ionic liquid, wherein the structural formula of the L-carnitine citric acid ionic liquid is as follows:
mixing and stirring the L-carnitine citric acid ionic liquid and collagen, and sequentially homogenizing, filtering, dialyzing and concentrating to obtain an ionic liquid collagen preparation;
the conditions of homogenization include: the pressure is 0-80 MPa, the flow is 30-60L/h, and the homogenization times are 1-3 times;
the conditions of the dialysis include: the time is 1-10 hours, and the dialysis times are 1-3 times.
2. The method for preparing the ionic liquid collagen preparation according to claim 1, wherein the method for preparing the L-carnitine citrate ionic liquid comprises the following steps:
respectively adding the L-carnitine salt and the citrate into a solvent to obtain a L-carnitine salt solution and a citrate solution;
and mixing the L-carnitine salt solution and the citrate solution, stirring under preset conditions, filtering, concentrating and drying to obtain the L-carnitine citric acid ionic liquid.
3. The method for preparing an ionic liquid collagen preparation according to claim 2, wherein the L-carnitine salt is one or more of L-carnitine hydrochloride, L-carnitine sulfate and L-carnitine bisulfate;
the citrate is one or more of sodium citrate and calcium citrate;
the solvent is one or more of water, ethanol, isopropanol and n-butanol;
the molar ratio of the L-carnitine salt to the citrate is 1:0.1-1:8.
4. The method for preparing an ionic liquid collagen preparation according to claim 2, wherein the preset conditions include: stirring under a mixed atmosphere of carbon dioxide and nitrogen, wherein the volume ratio of the carbon dioxide to the nitrogen is 99:1-99:10, and the pressure of the mixed atmosphere is 0.1-100 MPa.
5. The method for preparing the ionic liquid collagen preparation according to claim 1, wherein the mass ratio of the L-carnitine citrate ionic liquid to the collagen is 10:1-100:1.
6. The method for preparing an ionic liquid collagen preparation according to claim 1, wherein the step of mixing the ionic liquid of l-carnitine citrate with collagen specifically comprises: and adding the collagen into the L-carnitine citric acid ionic liquid within 10 to 60 minutes under the water area condition of 50 to 300rpm stirring speed and minus 5 to 40 ℃.
7. The method of preparing an ionic liquid collagen preparation according to claim 1, wherein the stirring time is 1 to 10 hours.
8. An ionic liquid collagen preparation, which is characterized by being prepared by the preparation method of the ionic liquid collagen preparation according to any one of claims 1 to 7.
9. Use of the ionic liquid collagen preparation according to claim 8 in the preparation of cosmetics.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112250588A (en) * | 2020-11-06 | 2021-01-22 | 哈尔滨工业大学（深圳） | L-carnitine ionic liquid and preparation method and application thereof |
| CN112370423A (en) * | 2020-11-04 | 2021-02-19 | 哈尔滨工业大学（深圳） | L-carnitine-based emulsion, preparation method and medicine |
| CN115192472A (en) * | 2022-07-28 | 2022-10-18 | 广州樊文花化妆品有限公司 | Whitening essence containing ionic liquid humanized type III collagen and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112370423A (en) * | 2020-11-04 | 2021-02-19 | 哈尔滨工业大学（深圳） | L-carnitine-based emulsion, preparation method and medicine |
| CN112250588A (en) * | 2020-11-06 | 2021-01-22 | 哈尔滨工业大学（深圳） | L-carnitine ionic liquid and preparation method and application thereof |
| CN115192472A (en) * | 2022-07-28 | 2022-10-18 | 广州樊文花化妆品有限公司 | Whitening essence containing ionic liquid humanized type III collagen and preparation method thereof |
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