Composition with emulsifying function and use thereof

Abstract

The application provides a composition with emulsification function and application thereof. The composition of the application can be prepared without or with less addition of conventional emulsifiers, thereby avoiding or reducing skin irritation and environmental hazards caused by the use of conventional emulsifiers; the emulsification performance of the composition of the application is excellent, complete emulsification of oil can be achieved, the composition can be used alone to prepare an emulsification system, and thus can be used in skin external products requiring the emulsification system.

Description

Technical Field

[0001] This application relates to compositions, and more specifically, to a composition having emulsifying properties and its applications. Background Technology

[0002] Emulsion systems with oil and water phases can not only replenish the skin with important oily components, hydrophilic moisturizing components, and moisture to maintain the water-oil balance, but also serve as carriers for skincare active ingredients and drugs, helping them to be absorbed by the skin and improving the bioavailability of active substances. Therefore, they have a wide range of applications.

[0003] Emulsifiers are an essential component of emulsion systems, enabling two or more incompatible components to form a stable dispersion. However, conventional emulsifiers often suffer from drawbacks such as high skin irritation and environmental harm. Therefore, developing an emulsifier that is more skin-friendly and environmentally friendly remains a pressing technical challenge in this field. Summary of the Invention

[0004] In view of the problems existing in the prior art, this application provides a composition with emulsifying function and its application.

[0005] Specifically, this application relates to the following aspects:

[0006] 1. A composition having emulsifying function, comprising a first complex and a second complex, wherein the first complex and the second complex have at least the following substructures:

[0007] AB(I)

[0008] A is a phytol group, and B is a disaccharide group in hyaluronic acid.

[0009] The degree of substitution of the phytol group in the first complex is 1-50%.

[0010] The degree of substitution of the phytol group in the second complex is 51-100%.

[0011] The mass ratio of the first complex to the second complex is (0.03-30):1.

[0012] 2. In the composition according to claim 1, the hydroxyl group of phytol is linked to the carboxyl group of the glucuronic acid moiety in the disaccharide group.

[0013] 3. The composition according to item 1 or 2, wherein the AB has the structure of formula (II):

[0014]

[0015] Wherein, R is the phytol group, and X is H or acetyl.

[0016] 4. The composition according to any one of items 1-3, wherein the first complex and / or the second complex further has a substructure of formula (III):

[0017]

[0018] Where R′ represents a metal ion and H, and X represents H and an acetyl group.

[0019] Preferably, the metal ion includes Na. + K + Zn 2+ One or more of them.

[0020] 5. The composition according to any one of items 1-4, wherein the mass ratio of the first complex to the second complex is (0.05-20):1.

[0021] 6. Use of the composition of any one of items 1-5 in the preparation of emulsifiers.

[0022] 7. Use of the composition of any one of items 1-5 in the preparation of an emulsion system.

[0023] 8. An emulsified system comprising an oil phase and an aqueous phase, wherein the oil phase and / or the aqueous phase contains the composition described in any one of claims 1-5.

[0024] Preferably, the sum of the contents of the first complex and the second complex is 0.005%-50%, and the oil content is 0.001%-10%.

[0025] Preferably, the average particle size of the emulsion system is less than or equal to 10 μm.

[0026] 9. A topical skin product comprising the composition of any one of items 1-5 or the emulsion system described in item 8.

[0027] 10. Use of the composition of any one of items 1-5 or the emulsion system of item 8 in the preparation of topical skin products.

[0028] Beneficial effects

[0029] The emulsifying composition provided in this application can be used without or with minimal addition of conventional emulsifiers, thus avoiding or reducing the skin irritation and environmental harm caused by the use of conventional emulsifiers.

[0030] The composition of this application has excellent emulsifying properties and can achieve complete emulsification of oils. It can be used alone to prepare emulsion systems and can be used in topical skin products that require emulsification systems, such as cosmetics and pharmaceuticals. Detailed Implementation

[0031] The present application is further illustrated below with reference to embodiments. It should be understood that the embodiments are only used to further illustrate and explain the present application and are not intended to limit the present application.

[0032] Unless otherwise defined, technical and scientific terms used in this specification have the same meaning as commonly understood by one of ordinary skill in the art. While similar or identical methods and materials may be applied in experimental or practical applications, materials and methods are described herein. In case of conflict, the definitions included herein shall prevail. Furthermore, materials, methods, and examples are for illustrative purposes only and are not intended to be limiting. The present application is further described below with reference to specific embodiments, but is not intended to limit the scope of the application.

[0033] This application provides a composition with emulsifying function, comprising a first complex and a second complex, wherein the first complex and the second complex have at least the following substructures:

[0034] AB(I)

[0035] A is a phytol group, and B is a disaccharide group in hyaluronic acid.

[0036] In some specific embodiments, the structure of A is shown in equation (IV):

[0037] (CH3)2CH(CH2)3CH(CH3)(CH2)3CH(CH3)(CH2)3C(CH3)CHCH2-(IV),

[0038] In some specific embodiments, the mass ratio of the first complex to the second complex is (0.03-30):1, for example, it can be 0.03:1, 0.05:1, 0.1:1, 0.5:1, 1:1, 2:1, 3:1, 4:1, 5:1, 6:1, 7:1, 8:1, 9:1, 10:1, 11:1, 12:1, 13:1, 14:1, 15:1, 16:1, 17:1, 18:1, 19:1, 20:1, 21:1, 22:1, 23:1, 24:1, 25:1, 26:1, 27:1, 28:1, 29:1, 30:1, or any value between these values.

[0039] In some specific embodiments, the mass ratio of the first complex to the second complex is (0.05-20):1.

[0040] In some specific embodiments, the structural formula of B is shown in the following formula (V):

[0041]

[0042] Where X represents H and acetyl groups.

[0043] In some specific embodiments, the hydroxyl group of phytol is linked to the carboxyl group of the glucuronic acid moiety in the disaccharide group.

[0044] In some specific embodiments, the AB has the structure of the following formula (II):

[0045]

[0046] Wherein, R is the phytol group, and X is H or acetyl.

[0047] In some specific embodiments, the complex also has a substructure of formula (III):

[0048]

[0049] Where R′ represents a metal ion and H, and X represents H and an acetyl group.

[0050] In some specific embodiments, the metal ions include Na. + K + Zn 2+ One or more of them.

[0051] In some specific implementations, the number of substructures in equation (III) is n1, and the number of substructures in equation (II) is n2, where n = n1 + n2.

[0052] In some specific implementations, n and n2 are both positive integers, and n1 is a natural number.

[0053] It is understandable that n can be arbitrarily selected based on the molecular weight range of existing hyaluronic acid, salts or their derivatives.

[0054] In some specific implementations, n is a positive integer less than 250, such as 249, 240, 230, 220, 210, 200, 190, 180, 170, 160, 150, 140, 130, 120, 110, 100, 99, 98, 97, 96, 95, 94, 93, 92, 91, 90, 89, 88, 87, 86, 85, 84, 83, 82, 81, 80, 79, 78, 77, 76, 75, 74, 73, 72, 71, 70, 69, 68, 67, 66, 65, 64 63, 62, 61, 60, 59, 58, 57, 56, 55, 54, 53, 52, 51, 50, 49, 48, 47, 46, 45, 44, 43, 42, 41, 40, 39, 38, 37, 36, 35, 34, 33, 32, 31, 30, 29, 28, 27, 26, 25, 24, 23, 22, 21, 20, 19, 18, 17, 16, 15, 14, 13, 12, 11, 10, 9, 8, 7, 6, 5, 4, 3, 2, 1, etc., or any positive integer and range between these values.

[0055] In some specific implementations, n1 can be a natural number less than 250, such as 249, 240, 230, 220, 210, 200, 190, 180, 170, 160, 150, 140, 130, 120, 110, 100, 99, 98, 97, 96, 95, 94, 93, 92, 91, 90, 89, 88, 87, 86, 85, 84, 83, 82, 81, 80, 79, 78, 77, 76, 75, 74, 73, 72, 71, 70, 69, 68, 67, 66, 65, 6 4, 63, 62, 61, 60, 59, 58, 57, 56, 55, 54, 53, 52, 51, 50, 49, 48, 47, 46, 45, 44, 43, 42, 41, 40, 39, 38, 37, 36, 35, 34, 33, 32, 31, 30, 29, 28, 27, 26, 25, 24, 23, 22, 21, 20, 19, 18, 17, 16, 15, 14, 13, 12, 11, 10, 9, 8, 7, 6, 5, 4, 3, 2, 1, 0, or any natural number and range between these values.

[0056] In some specific implementations, n2 can be a positive integer less than 250, such as 249, 240, 230, 220, 210, 200, 190, 180, 170, 160, 150, 140, 130, 120, 110, 100, 99, 98, 97, 96, 95, 94, 93, 92, 91, 90, 89, 88, 87, 86, 85, 84, 83, 82, 81, 80, 79, 78, 77, 76, 75, 74, 73, 72, 71, 70, 69, 68, 67, 66, 65. 64, 63, 62, 61, 60, 59, 58, 57, 56, 55, 54, 53, 52, 51, 50, 49, 48, 47, 46, 45, 44, 43, 42, 41, 40, 39, 38, 37, 36, 35, 34, 33, 32, 31, 30, 29, 28, 27, 26, 25, 24, 23, 22, 21, 20, 19, 18, 17, 16, 15, 14, 13, 12, 11, 10, 9, 8, 7, 6, 5, 4, 3, 2, 1, or any positive integer and range between these values.

[0057] In some specific embodiments, when the complex contains substructures of formula (III) and formula (II), the substructures of formula (III) and formula (II) can be connected in any order.

[0058] In the composition, the value of n can be the same or different for the first complex and the second complex.

[0059] In some specific embodiments, the molecular weight of the complex is not particularly limited and can be within the molecular weight range of existing hyaluronic acid or its derivatives, for example, less than 100 kDa, such as 99 kDa, 95 kDa, 90 kDa, 85 kDa, 80 kDa, 75 kDa, 70 kDa, 65 kDa, 60 kDa, 55 kDa, 50 kDa, 45 kDa, 40 kDa, 35 kDa, 30 kDa, 25 kDa, 20 kDa, 15 kDa, 10 kDa, 9 kDa, 8 kDa, 7 kDa, 6 kDa, 5 kDa, 4 kDa, 3 kDa, 2 kDa, 1 kDa, 0.8 kDa, 0.5 kDa, 0.4 kDa, 0.3 kDa, 0.2 kDa, 0.1 kDa, 800 Da, 400 Da, etc., or any value and range between these values, preferably 400 Da-500 Da.

[0060] In the composition, the molecular weights of the first and second complexes may be the same or different.

[0061] In some specific embodiments, the degree of substitution of the phytol group in the first complex is 1-50%, that is, the ratio of n2 to n in the first complex is 1-50%, for example, it can be 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 19%, 20%, 21%, 22%, 23%, 24%, 25%, 26%, 27%, 28%, 29%, 30%, 31%, 32%, 33%, 34%, 35%, 36%, 37%, 38%, 39%, 40%, 41%, 42%, 43%, 44%, 45%, 46%, 47%, 48%, 49%, 50%, etc., or any value or range between these values.

[0062] In some specific embodiments, the degree of substitution of the phytol group in the second complex is 51-100%, that is, the ratio of n2 to n in the first complex is 51-100%, for example, it can be 51%, 52%, 53%, 54%, 55%, 56%, 57%, 58%, 59%, 60%, 61%, 62%, 63%, 64%, 65%, 66%, 67%, 68%, 69%, 7 0%, 71%, 72%, 73%, 74%, 75%, 76%, 77%, 78%, 79%, 80%, 81%, 82%, 83%, 84%, 85%, 86%, 87%, 88%, 89%, 90%, 91%, 92%, 93%, 94%, 95%, 96%, 97%, 98%, 99%, 100%, etc., or any value or range between these values.

[0063] This application does not impose any particular limitation on the preparation methods of the first and second complexes; for example, they can be prepared by the following steps:

[0064] Step 1: Exchange hyaluronic acid or its salt or acetylated hyaluronic acid or its salt with a cation exchange resin to obtain cationized hyaluronic acid or its salt or cationized acetylated hyaluronic acid or its salt;

[0065] Step 2: The cationized substance obtained in Step 1 is activated with carboxyl groups in the presence of a catalyst;

[0066] Step 3: The product obtained in Step 2 after carboxyl activation is esterified with phytol to obtain a reaction product containing a phytol-hyaluronic acid complex.

[0067] In one specific embodiment, in step one, hyaluronic acid or its salt, or acetylated hyaluronic acid or its salt, is modified with tetrabutylammonium. The ion exchange time between the two is 1 hour to 10 hours, preferably 1 hour to 5 hours.

[0068] In one specific embodiment, in step two, the catalyst is preferably one or more of concentrated sulfuric acid, concentrated hydrochloric acid, and phosphoric acid.

[0069] The solvent used for the carboxyl activation or esterification reaction can be dimethyl sulfoxide, hyaluronic acid or its salt or acetylated hyaluronic acid or its salt, with a concentration of 0.1%-20% in dimethyl sulfoxide, preferably 1%-5%. The carboxyl activation time is 10 minutes to 5 hours, preferably 20 minutes to 2 hours.

[0070] In one specific embodiment, in step three, the ratio of hyaluronic acid or its salt, or acetylated hyaluronic acid or its salt, to phytol is (0.1-10):1. The esterification reaction temperature is 4-100℃, and the esterification reaction time is 1-48 hours.

[0071] The preparation method may further include the following steps:

[0072] Step 4: Separate and purify the reaction products;

[0073] Step 5: Dry the purified reaction product to obtain phytol-hyaluronic acid complex powder.

[0074] In particular, the separation, purification and drying steps in steps four and five can all be performed using methods known in the art.

[0075] For example, in step four, the reaction product can be diluted with a certain amount of ultrapure water, and a certain amount of isopropanol can be added. A white solid then precipitates, and centrifugation yields a crude product. The crude product obtained after centrifugation is then dialyzed to remove impurities. Further, the dialyzed product is added to a sodium chloride solution for ion exchange, with stirring time ranging from 1 hour to 24 hours, preferably 1 hour to 5 hours. Subsequently, purification with isopropanol yields the purified phytol-hyaluronic acid complex.

[0076] In step five, drying can be performed using freeze drying or spray drying.

[0077] In some specific embodiments, the degree of substitution of the phytol groups in the first and second complexes can be freely controlled by the feed ratio of hyaluronic acid or its derivatives to phytol.

[0078] The degree of substitution of the phytol groups in the first and second complexes can be detected using methods known in the art. For example, it can be detected by nuclear magnetic resonance. Specifically, the degree of substitution can be calculated according to Formula 1:

[0079]

[0080] Among them, A δ＝5.05 The integral area of ​​the olefin proton peak representing phytol, A δ＝4.50.4.40 The integral area of ​​the proton peak of the hemiacetal head hydrocarbon of hyaluronic acid.

[0081] This application also provides the use of any of the above compositions in the preparation of emulsifiers.

[0082] This application also provides the use of any of the above compositions in the preparation of emulsion systems.

[0083] This application also provides an emulsification system comprising an oil phase and an aqueous phase, wherein the oil phase and / or the aqueous phase contains any of the above-described compositions.

[0084] The oil used in the oil phase can be a commonly used oil in cosmetics, including polar oils and non-polar oils.

[0085] In some specific embodiments, the polar oils may include caprylic / capric triglycerides, squalane, wheat germ oil, cetyl ethylhexanoate, octyl dodecanol, triethylhexyl glycerol, isopropyl myristate, ethylhexyl palmitate, jojoba seed oil, sweet almond oil, decyl oleate, avocado oil, olive fruit oil, etc.; the non-polar oils may include polydimethylsiloxane, etc.

[0086] In some specific embodiments, the mass ratio of the composition to the oil is (5-15):1, for example, it can be 5:1, 6:1, 7:1, 8:1, 9:1, 10:1, 11:1, 12:1, 13:1, 14:1, 15:1, or any value or range between these values.

[0087] In some specific embodiments, the mass ratio of the composition to the oil is (7-12):1.

[0088] In some specific embodiments, the sum of the contents of the first complex and the second complex in the emulsion system is 0.005%-50%, for example, it can be 0.005%, 0.01%, 0.1%, 0.2%, 0.3%, 0.5%, 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 19%, 20%, 21%, 22%, 23%, 24%, 25%, 26%, 27%, 28%, 29%, 30%, 31%, 32%, 33%, 34%, 35%, etc. 36%, 37%, 38%, 39%, 40%, 41%, 42%, 43%, 44%, 45%, 46%, 47%, 48%, 49%, 50%, or any value or range between these values; the oil content is 0.001%-10%, for example, it can be 0.001%, 0.005%, 0.01%, 0.05%, 0.1%, 0.2%, 0.3%, 0.4%, 0.5%, 0.6%, 0.7%, 0.8%, 0.9%, 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, or any value or range between these values.

[0089] In one specific embodiment, the average particle size of the emulsion system is less than or equal to 10 μm, for example, it can be 10 μm, 9.5 μm, 9 μm, 8.5 μm, 8 μm, 7.5 μm, 7 μm, 6.5 μm, 6 μm, 5.5 μm, 5 μm, 4.5 μm, 4 μm, 3.5 μm, 3 μm, 2.5 μm, 2 μm, 1.5 μm, 1 μm, 0.9 μm, 0.8 μm, 0.7 μm, 0.6 μm, 0.5 μm, 0.4 μm, 0.3 μm, 0.2 μm, 0.1 μm, 0.05 μm, 0.01 μm, or any value or range between these values.

[0090] The average particle size of the emulsion system can be measured using methods known in the art, such as using a particle size analyzer.

[0091] This application also provides a topical skin product comprising any of the above-described compositions or emulsion systems. The topical skin product may be a cosmetic, pharmaceutical, or the like.

[0092] This application also provides the use of any of the above compositions or emulsion systems in the preparation of topical skin products.

[0093] The emulsifying composition provided in this application, in which the first and second complexes are mixed in a ratio of (0.03-30):1, has an emulsifying effect on non-polar, moderately polar, and strongly polar oils, forming a completely homogeneous emulsion with an average particle size of less than 10 μm. Therefore, the emulsion composition of this application can emulsify a variety of oils ranging from non-polar to polar.

[0094] Example

[0095] This application provides a general and / or specific description of the materials and test methods used in the experiments. In the following examples, unless otherwise specified, % represents wt%, i.e., weight percentage. Reagents or instruments used, unless otherwise specified, are all commercially available conventional reagent products.

[0096] In the following embodiments, the degree of substitution of the first and second complexes was detected by nuclear magnetic resonance. Specifically, based on the complexes... 1 The degree of substitution can be calculated using formula 1 from the H NMR spectrum:

[0097]

[0098] Among them, A δ＝5.05 The integral area of ​​the olefin proton peak representing phytol, A δ＝4.50.4.40 The integral area of ​​the proton peak of the hemiacetal head hydrocarbon of hyaluronic acid.

[0099] Blank control examples 1-3, Examples 1-15

[0100] According to Tables 1 and 2, each raw material was weighed, including water, the first complex (hereinafter referred to as HPE-L, with a degree of substitution of 10%), the second complex (hereinafter referred to as HPE-H, with a degree of substitution of 70%), and oils. Among them, the oil in blank control example 3 and examples 1-13 was caprylic / capric triglyceride (GTCC), the oil in example 14 was squalane, and the oil in example 15 was wheat germ oil.

[0101] Heat water, HPE-L, and HPE-H to 70-80℃, then start low-speed homogenization. Add the oil to the above solution, homogenize at 3-10 k RPM for 1-10 min, and then cool to room temperature to obtain the target emulsion.

[0102] The phenomena of each target emulsion were observed and the emulsion was diluted 200 times to prepare a dilute solution. The particle size was tested using an ANTON PAARLITESIZER 500 particle size analyzer, and the results are listed in Table 1.

[0103] The steps for preparing HPE-L are as follows:

[0104] (1) Dissolve 12.79g of sodium hyaluronate (molecular weight 800Da) in deionized water, and then perform ion exchange with tetrabutylammonium cation exchange resin for 2 hours to obtain tetrabutylammonium hyaluronic acid.

[0105] (2) Tetrabutylammonium hyaluronic acid was dissolved in 426.33g of dimethyl sulfoxide (DMSO) solvent and stirred thoroughly for 5 hours. Then, 1.279g of sulfuric acid was added to the above solution and stirred for 2 hours to activate the carboxyl group of hyaluronic acid. 2.2g of phytol was added to the above solution and esterification was carried out at 25°C for 24 hours to obtain the product.

[0106] (3) After the reaction is completed, the reaction solution is diluted in 2 equivalents of ultrapure water at room temperature and 10 equivalents of isopropanol is added. A white solid then precipitates out and is filtered to obtain the crude product. After centrifugation, the crude product is dialyzed to remove impurities and the product is obtained.

[0107] (4) Dissolve the product obtained in step (3) in sodium chloride solution (10%) and stir vigorously for 12 hours to obtain hyaluronic acid-phytol complex solution. Then, purify with isopropanol to obtain hyaluronic acid-phytol complex and freeze dry to obtain hyaluronic acid-phytol complex powder with a substitution degree of 10%, namely HPE-L.

[0108] The steps for preparing HPE-H are as follows:

[0109] (1) Dissolve 1.42g of sodium hyaluronate (molecular weight of 5kDa) in deionized water, and then perform ion exchange with tetrabutylammonium cation exchange resin for 2 hours to obtain tetrabutylammonium hyaluronic acid.

[0110] (2) Tetrabutylammonium hyaluronic acid was dissolved in 47.33g of dimethyl sulfoxide (DMSO) solvent and stirred thoroughly for 5 hours. Then, 0.142g of sulfuric acid was added to the above solution and stirred for 2 hours to activate the carboxyl group of hyaluronic acid. 1.6g of phytol was added to the above solution and esterification was carried out at 25°C for 24 hours to obtain the product.

[0111] (3) After the reaction is completed, the reaction solution is diluted in 2 equivalents of ultrapure water at room temperature and 10 equivalents of isopropanol is added. A white solid then precipitates out and is filtered to obtain the crude product. After centrifugation, the crude product is dialyzed to remove impurities and the product is obtained.

[0112] (4) Dissolve the product obtained in step (3) in sodium chloride solution (10%) and stir vigorously for 12 hours to obtain hyaluronic acid-phytol complex solution. Then, purify with isopropanol to obtain hyaluronic acid-phytol complex. Use freeze drying to obtain hyaluronic acid-phytol complex powder with a substitution degree of 70%, namely HPE-H.

[0113] Table 1

[0114]

[0115]

[0116] Where " / " indicates that the substance is not added or that the value does not exist; "Complete emulsification" means that an opaque, homogeneous emulsion is formed, with no surface oil floating; by mass percentage: HPE = HPE - H + HPE - L

[0117] As shown in blank control examples 1, 2, and 3, no emulsification occurred when HPE-H, HPE-L, and GTCC were mixed with water. Examples 1-3 show that adding HPE-H or HPE-L to water or GTCC, respectively, can achieve incomplete emulsification. Examples 4-15 show that when HPE-L and HPE-H are mixed in a ratio of (0.03-30):1, they can completely emulsify, forming a completely homogeneous emulsion with a particle size distribution below 10 μm, consistent with the particle size distribution of conventional emulsions.

[0118] As can be seen from Examples 6, 14, and 15, this composition has an emulsifying effect on moderately polar GTCC, non-polar squalane, and strongly polar wheat germ oil, and can form a completely homogeneous emulsion with an average particle size distribution of less than 10 μm. Therefore, this emulsion composition can emulsify a variety of oils from non-polar to polar.

[0119] Examples 16-51

[0120] To verify the emulsifying properties of hyaluronic acid phytol ester combinations with different degrees of substitution and different molecular weights, hyaluronic acid phytol esters with different degrees of substitution and different molecular weights were prepared. Emulsions were prepared by replacing the hyaluronic acid phytol esters of Example 9 according to the mass ratio of Example 9.

[0121] Preparation of HPE (sodium hyaluronate, molecular weight 800 Da, degree of substitution 50%):

[0122] The preparation method of HPE-L used in Example 1 is the same, except that the amount of hyaluronic acid added in step (1) is 2.56g, the amount of dimethyl sulfoxide (DMSO) solvent added in step (2) is 85.33g, the amount of sulfuric acid added is 0.256g, and the amount of phytol added is 2.1g.

[0123] Preparation of HPE (sodium hyaluronate, molecular weight 800 Da, degree of substitution 60%):

[0124] The preparation method of HPE-L used in Example 1 is the same, except that the amount of hyaluronic acid added in step (1) is 2.56g, the amount of dimethyl sulfoxide (DMSO) solvent added in step (2) is 85.33g, the amount of sulfuric acid added is 0.256g, and the amount of phytol added is 2.5g.

[0125] Preparation of HPE (sodium hyaluronate, molecular weight 800 Da, degree of substitution 90%):

[0126] The preparation method of HPE-L used in Example 1 is the same, except that the amount of hyaluronic acid added in step (1) is 1.42g, the amount of dimethyl sulfoxide (DMSO) solvent added in step (2) is 47.33g, the amount of sulfuric acid added is 0.142g, and the amount of phytol added is 2.2g.

[0127] Preparation of HPE (sodium hyaluronate, molecular weight 5 kDa, degree of substitution 10%):

[0128] The preparation method of HPE-L used in Example 1 is the same, except that the molecular weight of hyaluronic acid in step (1) is 5 kDa.

[0129] Preparation of HPE (sodium hyaluronate, molecular weight 5kDa, degree of substitution 50%):

[0130] The preparation method is the same as that of HPE (sodium hyaluronate with a molecular weight of 800 Da and a degree of substitution of 50%), except that the molecular weight of hyaluronic acid in step (1) is 5 kDa.

[0131] Preparation of HPE (sodium hyaluronate, molecular weight 5 kDa, degree of substitution 60%):

[0132] The preparation method is the same as that of HPE (sodium hyaluronate with a molecular weight of 800 Da and a degree of substitution of 60%), except that the molecular weight of hyaluronic acid in step (1) is 5 kDa.

[0133] Preparation of HPE (sodium hyaluronate, molecular weight 5 kDa, degree of substitution 90%):

[0134] The preparation method is the same as that of HPE (sodium hyaluronate with a molecular weight of 800 Da and a degree of substitution of 90%), except that the molecular weight of hyaluronic acid in step (1) is 5 kDa.

[0135] Preparation of HPE (sodium hyaluronate, molecular weight 30 kDa, degree of substitution 10%):

[0136] The preparation method of HPE-L used in Example 1 is the same, except that the molecular weight of hyaluronic acid in step (1) is 30 kDa.

[0137] Preparation of HPE (sodium hyaluronate, molecular weight 30 kDa, degree of substitution 50%):

[0138] The preparation method is the same as that of HPE (sodium hyaluronate with a molecular weight of 800 Da and a degree of substitution of 50%), except that the molecular weight of hyaluronic acid in step (1) is 30 kDa.

[0139] Preparation of HPE (sodium hyaluronate, molecular weight 30 kDa, degree of substitution 60%):

[0140] The preparation method is the same as that of HPE (sodium hyaluronate with a molecular weight of 800 Da and a degree of substitution of 60%), except that the molecular weight of hyaluronic acid in step (1) is 30 kDa.

[0141] Preparation of HPE (sodium hyaluronate, molecular weight 30 kDa, degree of substitution 90%):

[0142] The preparation method is the same as that of HPE (sodium hyaluronate with a molecular weight of 800 Da and a degree of substitution of 90%), except that the molecular weight of hyaluronic acid in step (1) is 30 kDa.

[0143] Specifically, the molecular weights and degrees of substitution of HPE-L and HPE-H used in each embodiment are shown in Table 2. The phenomena observed in each target emulsion were observed, and the emulsions were diluted 200 times to prepare dilute solutions. The particle size was measured using an ANTON PAAR LITESIZER 500 particle size analyzer, and the results are listed in Table 2.

[0144] Table 2

[0145]

[0146]

[0147] As shown in Table 2, mixing HPE-L and HPE-H ratios with other molecular weights and degrees of substitution can also achieve complete emulsification of oils and fats, and can be used to prepare cosmetic emulsion formulations.

Claims

1. A composition having emulsifying function, comprising a first complex and a second complex, wherein the first complex and the second complex have at least the following substructures: AB (I) A is a phytol group, and B is a disaccharide group in hyaluronic acid. The degree of substitution of the phytol group in the first complex is 1-50%. The degree of substitution of the phytol group in the second complex is 51-100%. The mass ratio of the first complex to the second complex is (0.03-30):1; The AB has the structure of the following formula (II): (II) in, R is the phytol group, and X is H or acetyl.

2. The composition according to claim 1, wherein the hydroxyl group of phytol is linked to the carboxyl group of the glucuronic acid moiety in the disaccharide group.

3. The composition according to claim 1, wherein the first complex and / or the second complex further have a substructure of formula (III): (III) in, R′ represents a metal ion and H, while X represents H and an acetyl group.

4. The composition according to claim 3, wherein the metal ion comprises Na. + K + Zn 2+ One or more of them.

5. The composition according to any one of claims 1-4, wherein, The mass ratio of the first complex to the second complex is (0.05-20):

1.

6. Use of the composition according to any one of claims 1-5 in the preparation of emulsifiers.

7. Use of the composition according to any one of claims 1-5 in the preparation of an emulsion system.

8. An emulsified system comprising an oil phase and an aqueous phase, wherein the oil phase and / or the aqueous phase contains the composition of any one of claims 1-5.

9. The emulsification system according to claim 8, wherein the sum of the contents of the first complex and the second complex is 0.005%-50%, and the content of oil is 0.001%-10%.

10. The emulsion system according to claim 8, wherein the average particle size of the emulsion system is less than or equal to 10 μm.

11. A topical skin product comprising the composition of any one of claims 1-5 or the emulsion system of any one of claims 8-10.

12. Use of the composition of any one of claims 1-5 or the emulsion system of any one of claims 8-10 in the preparation of topical skin products.

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