Composition with emulsifying function and application thereof

Abstract

The invention provides a composition with an emulsifying function and application thereof. According to the composition disclosed by the invention, no or less conventional emulsifier is added, so that skin irritation and environmental harmfulness caused by using the conventional emulsifier are avoided or reduced; the composition disclosed by the invention is excellent in emulsifying performance, can realize complete emulsification of grease, can be independently used for preparing an emulsifying system, and thus can be used in skin external products needing the emulsifying system.

Description

Technical Field

[0001] The present application relates to a composition, in particular, to a composition with emulsification function and application thereof. Background Art

[0002] An emulsification system with an oil phase and an aqueous phase can not only replenish the skin with important oily components, hydrophilic moisturizing components and moisture to maintain the balance of water and oil, but also serve as a carrier for skin care active ingredients and drugs, assisting the skin care active ingredients and drugs to be absorbed by the skin and improving the bioavailability of effective substances. Therefore, it has a wide range of uses.

[0003] An essential component of an emulsified system is an emulsifier, which can form a stable dispersion system of two or more incompatible components. However, conventional emulsifiers currently used usually have the disadvantages of being highly irritating to the skin and harmful to the environment. Therefore, how to develop an emulsifier that is more skin-friendly and environmentally friendly is still a technical problem that needs to be solved urgently in this field. Summary of the invention

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

[0005] Specifically, this application involves the following aspects:

[0006] 1. A composition with emulsification 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 of the first complex is 1-50%,

[0010] The degree of substitution of the phytol group of 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. According to the composition of item 1, the hydroxyl group of phytol is linked to the carboxyl group of the glucuronic acid part in the disaccharide group.

[0013] 3. The composition according to item 1 or 2, wherein AB has the structure of the following 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 to 3, wherein the first complex and / or the second complex further has a substructure of formula (III):

[0017]

[0018] Wherein, R' is a metal ion, H, X is H, acetyl,

[0019] Preferably, the metal ions include Na + , K + 、Zn 2+ One or more of .

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

[0021] 6. Use of the composition described in any one of items 1 to 5 in the preparation of an emulsifier.

[0022] 7. Use of the composition described in any one of items 1 to 5 in the preparation of an emulsified 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 items 1 to 5,

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

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

[0026] 9. A skin external product comprising the composition according to any one of items 1 to 5 or the emulsification system according to item 8.

[0027] 10. Use of the composition according to any one of items 1 to 5 or the emulsification system according to item 8 in the preparation of a skin external product.

[0028] Beneficial Effects

[0029] The composition with emulsification function provided in the present application can add no or less conventional emulsifiers, thereby avoiding or reducing the skin irritation and environmental harm caused by the use of conventional emulsifiers;

[0030] The composition of the present application has excellent emulsifying properties, can achieve complete emulsification of oils and fats, can be used alone to prepare an emulsifying system, and can thus be used in skin topical products that require an emulsifying system, such as cosmetics, medicines, and the like. DETAILED DESCRIPTION

[0031] The present application is further described below in conjunction with examples. It should be understood that the examples are only used to further describe and illustrate the present application and are not used to limit the present application.

[0032] Unless otherwise defined, the technical and scientific terms in this specification have the same meaning as those generally understood by those skilled in the art. Although similar or identical methods and materials as described herein may be used in experiments or practical applications, materials and methods are described herein below. In the event of a conflict, the present specification including the definitions therein shall prevail. In addition, materials, methods and examples are provided for illustration only and are not restrictive. The present application is further described below in conjunction with specific embodiments, but is not intended to limit the scope of the present application.

[0033] The present application provides a composition with an 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] The A is a phytol group, and the B is a disaccharide group in hyaluronic acid.

[0036] In some specific embodiments, the structure of A is shown in the following formula (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] Wherein, X is H or acetyl.

[0043] In some specific embodiments, the hydroxyl group of phytol is linked to the carboxyl group of the glucuronic acid portion of 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 further has a substructure of formula (III):

[0048]

[0049] Wherein, R' is a metal ion or H, and X is H or acetyl.

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

[0051] In some specific embodiments, the number of substructures of formula (III) is n1, the number of substructures of formula (II) is n2, and n=n1+n2.

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

[0053] It is understood that n can be arbitrarily selected according to the molecular weight range of existing hyaluronic acid, salts or derivatives thereof.

[0054] In some specific embodiments, n is a positive integer less than 250, for example, 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 embodiments, n1 can be a natural number less than 250, for example, 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, 66 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 or range between these values.

[0056] In some specific embodiments, n2 can be a positive integer less than 250, for example, 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, 1, 20, 19, 18, 17, 16, 15, 14, 13, 12, 11, 10, 9, 8, 7, 6, 5, 4, 3, 2, 1, or any positive integer or range therebetween.

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

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

[0059] In some specific embodiments, the molecular weight of the complex is not particularly limited, and can be the molecular weight range of existing hyaluronic acid or its derivatives, for example, it can be less than 100 kDa, for example, it can be 99 kDa, 95 kDa, 90 kDa, 85 kDa, 80 kDa Da, 75 kDa Da, 70 kDa Da, 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 Da, 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-5 wDa.

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

[0061] In some specific embodiments, the degree of substitution of the phytol groups 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 of 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%, 70%, 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%, 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] The present application does not impose any particular limitation on the preparation method of the first composite and the second composite, and for example, the preparation can be performed by the following steps:

[0064] Step 1: exchanging 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: activating the carboxyl group of the cationized substance obtained in step 1 in the presence of a catalyst;

[0066] Step 3: subjecting the carboxyl activated product obtained in step 2 to an esterification reaction with phytol to obtain a reaction product containing a phytol-hyaluronic acid complex.

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

[0068] In a specific embodiment, in step 2, the catalyst is preferably one or more of concentrated sulfuric acid, concentrated hydrochloric acid, and phosphoric acid.

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

[0070] In a specific embodiment, in step 3, the feed ratio of the hyaluronic acid or its salt, or acetylated hyaluronic acid or its salt to phytol is (0.1-10): 1. The temperature of the esterification reaction is 4-100° C., and the time of the esterification reaction is 1-48 hours.

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

[0072] Step 4: separating and purifying the reaction product;

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

[0074] The separation, purification and drying steps in step 4 and step 5 can be carried out using methods known in the art.

[0075] For example, in step 4, the reaction product can be poured into a certain amount of ultrapure water for dilution, and a certain amount of isopropanol is added, and then white solid is precipitated, and the crude product is obtained by centrifugation. The crude product obtained after centrifugation is dialyzed to remove impurities. Further, the product obtained after dialysis is added to sodium chloride solution and ion exchange is carried out, and the churning time is 1 hour-24 hours, and preferably, the churning time is 1 hour-5 hours. Subsequently, the phytol-hyaluronic acid complex after purification is obtained using isopropanol purification.

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

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

[0078] The degree of substitution of the phytol group of the first complex and the second complex can be detected by 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 integrated area of ​​the olefinic hydrogen proton peak representing phytol, A δ＝4.50.4.40 The integrated area of ​​the proton peak representing the hemiacetal head carbon and hydrogen of hyaluronic acid.

[0081] The present application also provides use of any one of the above compositions in preparing an emulsifier.

[0082] The present application also provides the use of any one of the above compositions in preparing an emulsified system.

[0083] The present application also provides an emulsified system, comprising an oil phase and an aqueous phase, wherein the oil phase and / or the aqueous phase contains any one of the above-mentioned compositions.

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

[0085] In some specific embodiments, the polar oil may include caprylic / capric triglyceride, squalane, wheat germ oil, cetyl ethylhexanoate, octyldodecanol, triethylhexyl glyceryl, isopropyl myristate, ethylhexyl palmitate, jojoba seed oil, sweet almond oil, decyl oleate, avocado oil, olive oil, etc.; the non-polar oil 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, in the emulsified system, the sum of the contents of the first complex and the second complex 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%, 36%, 37%, 38%, 39%, 40%, 41%, 42%, 43%, 44%, 45%, 46%, 47%, 48%, 49%, 50%, or any value or range therebetween; the fat content is 0.001%-10%, for example, 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 therebetween.

[0089] In a specific embodiment, the average particle size of the emulsified 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 emulsified system can be measured by methods known in the art, for example, using a particle size analyzer.

[0091] The present application also provides a skin external product, comprising any one of the above-mentioned compositions or emulsified systems, wherein the skin external product may be a cosmetic, a medicine, or the like.

[0092] The present application also provides use of any one of the above-mentioned compositions or emulsification systems in the preparation of external skin products.

[0093] The first complex and the second complex in the composition with emulsification function provided by the present application are mixed in a ratio of (0.03-30):1, and have an emulsification effect on non-polar, medium-polar and strong-polar oils and fats, and can form a completely uniform emulsion with an average particle size of less than 10 μm. Therefore, the emulsion composition of the present application can emulsify a variety of oils from non-polar to polar.

[0094] Example

[0095] The present 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, % means wt%, i.e., weight percentage. The reagents or instruments used without indicating the manufacturer are all conventional reagent products that can be obtained commercially.

[0096] In the following examples, the substitution degree of the first complex and the second complex is detected by nuclear magnetic resonance. 1 H NMR spectrum, the degree of substitution can be calculated according to formula 1:

[0097]

[0098] Among them, A δ＝5.05 The integrated area of ​​the olefinic hydrogen proton peak representing phytol, A δ＝4.50.4.40 The integrated area of ​​the proton peak representing the hemiacetal head carbon and hydrogen of hyaluronic acid.

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

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

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

[0102] The phenomenon of each target emulsion was 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. The results are listed in Table 1.

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

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

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

[0106] (3) After the reaction is completed, the reaction solution is poured into 2 equivalents of ultrapure water at room temperature for dilution, and 10 equivalents of isopropanol are added, and then a white solid is precipitated, which is filtered to obtain a crude product; the crude product obtained after centrifugation is dialyzed to remove impurities to obtain the product.

[0107] (4) The product obtained in step (3) is dissolved in a sodium chloride solution (10%) and vigorously stirred for 12 hours to obtain a hyaluronic acid-phytol complex solution, which is then purified by isopropanol to obtain a hyaluronic acid-phytol complex, and freeze-dried to obtain a hyaluronic acid-phytol complex powder with a degree of substitution of 10%, i.e., HPE-L.

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

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

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

[0111] (3) After the reaction is completed, the reaction solution is poured into 2 equivalents of ultrapure water at room temperature for dilution, and 10 equivalents of isopropanol are added, and then a white solid is precipitated, which is filtered to obtain a crude product; the crude product obtained after centrifugation is dialyzed to remove impurities to obtain the product.

[0112] (4) The product obtained in step (3) is dissolved in a sodium chloride solution (10%) and vigorously stirred for 12 hours to obtain a hyaluronic acid-phytol complex solution, which is then purified by isopropanol to obtain a hyaluronic acid-phytol complex, and freeze-dried to obtain a hyaluronic acid-phytol complex powder with a degree of substitution of 70%, i.e., HPE-H.

[0113] Table 1

[0114]

[0115]

[0116] Where “ / ” means that the substance is not added or the value does not exist; “Complete emulsification” means the formation of an opaque uniform emulsion without the presence of floating oil on the surface; In terms of mass percentage: HPE = HPE-H + HPE-L

[0117] From blank control examples 1, 2, and 3, it can be seen that HPE-H, HPE-L, and GTCC are mixed with water respectively, and there is no emulsification phenomenon. From examples 1-3, it can be seen that adding HPE-H or HPE-L to water and GTCC respectively can achieve incomplete emulsification. From examples 4-15, it can be seen that HPE-L and HPE-H can be completely emulsified when mixed in a ratio of (0.03-30):1 to form a completely uniform emulsion, and the emulsion particle size is distributed below 10μm, which is consistent with the particle size distribution of conventional emulsions.

[0118] It can be seen from Examples 6, 14 and 15 that the composition has an emulsifying effect on medium-polar GTCC, non-polar squalane and strong-polar wheat germ oil, and can form completely uniform emulsions with an average particle size distribution of less than 10 μm. Therefore, the emulsion composition can emulsify a variety of oils from non-polar to polar.

[0119] Embodiment 16-51

[0120] In order to verify the emulsifying properties of the combination of hyaluronic acid phytol esters with different degrees of substitution and different molecular weights, hyaluronic acid phytol esters with different degrees of substitution and different molecular weights were prepared, and the hyaluronic acid phytol esters of Example 9 were replaced according to the mass ratio of Example 9 to prepare emulsions.

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

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

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

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

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

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

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

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

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

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

[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 (molecular weight of sodium hyaluronate 800Da, degree of substitution 60%), except that the molecular weight of hyaluronic acid in step (1) is 5kDa.

[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 (molecular weight of sodium hyaluronate 800Da, degree of substitution 90%), except that the molecular weight of hyaluronic acid in step (1) is 5kDa.

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

[0136] The preparation method of HPE-L is the same as that used in Example 1, 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 (molecular weight of sodium hyaluronate 800Da, degree of substitution 50%), except that the molecular weight of hyaluronic acid in step (1) is 30kDa.

[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 (molecular weight of sodium hyaluronate 800Da, degree of substitution 60%), except that the molecular weight of hyaluronic acid in step (1) is 30kDa.

[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 (molecular weight of sodium hyaluronate 800Da, degree of substitution 90%), except that the molecular weight of hyaluronic acid in step (1) is 30kDa.

[0143] Specifically, the molecular weight and degree of substitution of HPE-L and HPE-H used in each example are shown in Table 2. The phenomenon of each target emulsion was observed and the emulsion was diluted 200 times to prepare a dilute solution, and the particle size was tested using an ANTON PAAR LITESIZER 500 particle size analyzer. The results are listed in Table 2.

[0144] Table 2

[0145]

[0146]

[0147] From the results in Table 2, it can be seen that the complete emulsification of oils and fats can be achieved by mixing HPE-L and HPE-H with other molecular weights and degrees of substitution, and can be used to prepare cosmetic emulsion formulas.

Claims

1. A composition with emulsification 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 of the first complex is 1-50%, The degree of substitution of the phytol group of the second complex is 51-100%, The mass ratio of the first complex to the second complex is (0.03-30):

1.

2. compositions according to claim 1, the hydroxyl group of phytol is connected with the carboxyl group of the glucuronic acid part in the disaccharide group.

3. The composition according to claim 1 or 2, wherein AB has the structure of the following formula (II): in, R is the phytol group, and X is H or acetyl.

4. The composition according to any one of claims 1 to 3, wherein the first complex and / or the second complex further has a substructure of the following formula (III): in, R' is a metal ion, H, X is H, acetyl, Preferably, the metal ions include Na + , K + 、Zn 2+ One or more of .

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

1.

6. Use of the composition according to any one of claims 1 to 5 in the preparation of an emulsifier.

7. Use of the composition according to any one of claims 1 to 5 in preparing an emulsified 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 according to any one of claims 1 to 5, Preferably, the sum of the contents of the first compound and the second compound is 0.005%-50%, and the content of oil is 0.001%-10%. Preferably, the average particle size of the emulsified system is less than or equal to 10 μm.

9. A skin external product comprising the composition according to any one of claims 1 to 5 or the emulsified system according to claim 8.

10. Use of the composition according to any one of claims 1 to 5 or the emulsification system according to claim 8 in the preparation of a skin external product.

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