Glycoside emulsifier, and preparation method and application thereof

Abstract

The application relates to the technical field of chemical synthesis, and particularly discloses a glycoside emulsifier as well as a preparation method and application thereof. The glycoside emulsifier is composed of a glycoside and a sucrose ester; the glycoside is 50-95 parts by mass, and the sucrose ester is 5-50 parts by mass, with the total mass of the glycoside emulsifier being 100 parts. The glycoside and the sucrose ester are compounded in the above mass proportions, and a significant synergistic effect is generated: the emulsifying capacity is significantly enhanced, various types of oils (including mineral oil, vegetable oil, silicone oil and the like) can be emulsified, and the emulsified system has high stability; the skin feeling experience is excellent, and the unique skin feeling is light, thin, skin-friendly, water-wet and non-sticky.

Description

Technical Field

[0001] This invention relates to the field of chemical synthesis technology, and in particular to a glycoside emulsifier, its preparation method, and its application. Background Technology

[0002] Glycoside emulsifiers are widely used in daily chemical, food, and pharmaceutical industries due to their good biodegradability, low irritation, and excellent emulsifying properties. The preparation of existing glycoside emulsifiers mostly employs acid-catalyzed glycosylation reactions. Commonly used catalysts include liquid acids such as sulfuric acid and p-toluenesulfonic acid, as well as solid acids such as zirconium oxide sulfate (SO4²⁻ / ZrO2). Liquid acid catalysts suffer from problems such as equipment corrosion, difficulty in waste acid treatment, and complex product separation. While traditional solid acids can be recycled, they still have bottlenecks such as poor thermal stability, uneven acid sites, easy sulfur loss, and low catalytic efficiency, limiting their widespread application in industrial production.

[0003] Patent publication number CN103494714A discloses an emulsifier composition capable of forming a liquid crystal structure and its application. It discloses the following raw material weight percentages: hydrogenated lecithin 10-60%, alkyl glycosides 5-40%, and sucrose esters 5-50%. This scheme indicates that the combination of alkyl glycosides and sucrose esters helps to form a liquid crystal structure, which can increase the storage stability of the emulsion and prolong the retention time of hydration properties during cosmetic use. However, this scheme uses hydrogenated lecithin as the main component and alkyl glycosides and sucrose esters as auxiliary components. It fails to reveal the synergistic emulsifying effect of the binary combination of alkyl glycosides and sucrose esters themselves, and does not involve green preparation methods for glycosides, particularly the application of highly efficient solid acid catalysts in glycoside synthesis.

[0004] Patent publication number CN108379105A discloses a cosmetic-grade emulsifier composed of 65%–80% long-chain alkyl glycosides, 25%–30% long-chain fatty alcohols, and 45%–50% glycerol mono- and long-chain fatty acid esters. Patent publication number CN104367485A discloses a composite emulsifier composed of 30%–60% long-chain alkyl glycosides, 5%–20% long-chain fatty alcohols, and 5%–40% glycerol mono- and long-chain fatty acid esters, etc. Both of these solutions involve the compounding of alkyl glycosides with other components, but none address the binary compounding system of alkyl glycosides and sucrose esters, and systematic research on the synergistic emulsification mechanism of these two compounds is lacking.

[0005] Patent publication number CN103665062A discloses a method for producing alkyl glycosides from starch, which involves a catalyst for preparing nano-magnetic solid superacids (containing Zr and Ti, activated by ammonium sulfate immersion) by chemical coprecipitation. In essence, it is still a solid superacid in the traditional sense.

[0006] In addition, most existing glycoside emulsifiers are single glycoside components, which have problems such as insufficient emulsification stability, poor formulation compatibility, and sticky skin feel.

[0007] Therefore, developing a glycoside emulsifier with excellent emulsifying properties and a non-sticky feel has extremely high market potential. Summary of the Invention

[0008] The purpose of this invention is to overcome the shortcomings of the prior art by providing a glycoside emulsifier, its preparation method, and its application. The glycoside emulsifier provided by this invention has excellent emulsifying properties and a unique skin feel.

[0009] To achieve the above objectives, the technical solution adopted by the present invention is as follows: This invention provides a glycoside emulsifier, which is composed of glycosides and sucrose esters; Based on a total mass of 100 parts of the glycoside emulsifier, the glycoside is 50-95 parts by mass and the sucrose ester is 5-50 parts by mass; The glycosides include at least one of alkyl glucoside, alkyl xylose, alkyl maltose, alkyl fructoside, alkyl galactoside, and alkyl mannoside, wherein the alkyl group is C12 to C22.

[0010] This invention provides a glycoside emulsifier, which is composed of glycosides and sucrose esters. By compounding the glycosides and sucrose esters in the above-mentioned mass proportions, a significant synergistic effect is produced: the emulsifying ability is significantly enhanced, and it can emulsify various types of oils (including mineral oil, vegetable oil, silicone oil, etc.), and the emulsion system has high stability; the skin feel is excellent, with a unique skin feel that is light, skin-friendly, moisturizing and non-sticky.

[0011] The glycoside emulsifier provided by this invention avoids the problems of insufficient emulsification stability and sticky feel that exist when using a single glycoside component. It has good formulation compatibility and excellent liquid crystal structure (the formation of the liquid crystal structure of glycoside emulsifier is a process in which amphiphilic molecules transform from a disordered state to an intermediate phase (mesocrystalline state) with long-range order through self-assembly under specific concentration, temperature and molecular stacking conditions; the crystalline structure can endow the system with high stability and sustained-release properties). It has great potential in terms of physicochemical stability, controlled release and moisturizing.

[0012] As a preferred embodiment of the glycoside emulsifier of the present invention, the glycoside is at least one selected from cetearyl xyloside, cetearyl glucoside, cetearyl xyloside, cetearyl glucoside, stearyl xyloside, stearyl glucoside, arachidyl xyloside, arachidyl glucoside, behenyl xyloside, and behenyl glucoside.

[0013] The present invention uses the above-mentioned types of glycosides, which can make glycoside emulsifiers have better emulsifying effects. The glycosides, as the main emulsifiers, are prepared by reaction with a specific catalyst, which is different from conventional glycosides and has better performance.

[0014] As a preferred embodiment of the glycoside emulsifier of the present invention, the sucrose ester includes at least one of sucrose polysaccharide, sucrose polycotyl oleate, sucrose polystearate, sucrose polyoleate, sucrose polylinoleate, sucrose polylaurate, sucrose hexasqualide, sucrose hexapalmitate, sucrose hexastearate, sucrose myristate, sucrose tetraisostearate, sucrose pentasqualide, sucrose distearate, sucrose dilaurate, sucrose tristearate, sucrose trisharpenate, sucrose stearate, sucrose oleate, sucrose laurate, sucrose palmitate, sucrose cocoate, and sucrose behenate.

[0015] This invention uses the above-mentioned sucrose esters as auxiliary emulsifiers, combined with glycosides, and compounded in specific mass parts to make the emulsification effect of glycoside emulsifiers better. It can emulsify a variety of types of oils (including mineral oil, vegetable oil, silicone oil, etc.), and the emulsion system has high stability. It has an excellent skin feel, with a unique skin feel that is light, skin-friendly, moisturizing and non-sticky.

[0016] In a preferred embodiment of the glycoside emulsifier of the present invention, the sucrose ester is at least one selected from sucrose stearate, sucrose oleate, sucrose laurate, sucrose palmitate, and sucrose behenate.

[0017] This invention provides a method for preparing the above-mentioned glycoside emulsifier. The glycoside and sucrose ester are weighed according to the above-mentioned mass proportions, melted and mixed evenly at a temperature of 65~120℃, and then granulated to obtain the glycoside emulsifier.

[0018] The method for preparing glycoside emulsifiers provided by this invention is simple, requires no complex equipment, and is easy to industrialize.

[0019] In a preferred embodiment of the preparation method of the glycoside emulsifier of the present invention, the preparation method of the glycoside includes the following steps: 1) Weigh out the alkyl alcohol and heat it to 50~100℃ until the alkyl alcohol is completely molten; 2) Weigh the solid superacid catalyst and 3A molecular sieve, disperse them in a molten alkyl alcohol, and obtain a mixture; 3) Weigh the sugar, add it to the mixture, and heat it to 90~150℃ to react and obtain the reaction material; 4) The reactants are filtered to separate and remove the solid superacid catalyst and 3A molecular sieve, and glycosides are obtained.

[0020] Glycosides are prepared by reacting fatty alcohols with sugars. Traditional processes often involve an excess of fatty alcohols due to low glycoside conversion rates, resulting in a large amount of residual fatty alcohols in the product, which are difficult to remove. The glycosides prepared by the method described in this invention have a higher conversion rate, thus allowing for more controllable product purity and better overall performance.

[0021] This invention uses a novel solid superacid catalyst to prepare glycosides, which can further improve the conversion rate of glycosides, thereby enhancing the performance of emulsifiers.

[0022] In some specific embodiments, the method for preparing the glycoside includes the following steps: 1) Weigh the alkyl alcohol into a three-necked flask and heat it to 50~100℃ until the alkyl alcohol is completely molten; 2) Weigh out the solid superacid and 3A molecular sieve, turn on the stirrer to evenly disperse the solid particles in the molten alkyl alcohol to obtain a mixture; 3) Weigh the sugar, add it to the mixture, heat to 90~150℃, assemble the condenser, collect the water produced by the reaction, and set the vacuum negative pressure to -0.08±0.005MPa. React for 5-10 hours to obtain the reaction material. 4) The reactants are then filtered to separate and remove the solid superacid catalyst and 3A molecular sieve, thus obtaining the glycoside.

[0023] In a preferred embodiment of the preparation method of the glycoside emulsifier of the present invention, the alkyl alcohol is a C12~C22 alcohol.

[0024] The alkyl alcohol includes at least one of cetyl alcohol, stearyl alcohol, arachidyl alcohol, and behenyl alcohol.

[0025] Preferably, the sugar is at least one selected from glucose, xylose, maltose, fructose, galactose, and mannose.

[0026] This invention utilizes the aforementioned types of sugars to induce a glycosylation reaction, and with the aid of a solid superacid catalyst, the glycoside conversion rate is significantly improved.

[0027] Preferably, the solid superacid catalyst comprises X-ZrO2-SO4. 2- @mSiO2. Where X is selected from Ce, Nd, and Sc.

[0028] The solid superacid catalysts of the above-mentioned types have high specific surface area, high acid strength and excellent thermal stability, which can significantly improve the conversion rate of glycosylation reaction.

[0029] In a preferred embodiment of the preparation method of the glycoside emulsifier of the present invention, the molar ratio of the alkyl alcohol to the sugar is (1.1~1.8):1.

[0030] Preferably, the amount of the solid superacid added is 0.1% to 2% of the total mass of the alkyl alcohol and sugar.

[0031] Preferably, the amount of 3A molecular sieve added is 1% to 10% of the total mass of alkyl alcohol and sugar.

[0032] This invention also provides the application of the above-mentioned glycoside emulsifiers in the preparation of cosmetics.

[0033] The present invention also provides a cosmetic product comprising 1 to 10 wt% of a glycoside emulsifier.

[0034] In some specific embodiments, the cosmetic is one of ointment, cream, or lotion. In the technical solution of this invention, the cosmetic may also be other dosage forms such as ointment, cream, or lotion.

[0035] Compared with the prior art, the present invention has the following beneficial effects: This invention provides a glycoside emulsifier, its preparation method, and its application. The glycoside emulsifier is composed of glycosides and sucrose esters. By compounding the glycosides and sucrose esters within a specific ratio range, a significant synergistic effect is achieved: emulsifying ability is significantly enhanced, enabling the emulsification of various types of oils (including mineral oil, vegetable oil, silicone oil, etc.), and the emulsion system exhibits high stability; it also provides an excellent skin feel, with a lightweight, skin-adhering, moisturizing, and non-sticky texture. The glycoside emulsifier provided by this invention avoids the problems of insufficient emulsification stability and sticky skin feel that exist when using a single glycoside component. It has good formulation compatibility and an excellent liquid crystal structure, showing great potential in terms of physicochemical stability, controlled release, and moisturizing properties. Furthermore, the preparation method of the glycoside emulsifier is simple, requires no complex equipment, and is easy to industrialize. Attached Figure Description

[0036] Figure 1 The detection chromatogram of cetyl xyloside prepared in Example 1; Figure 2 This is a comparison chart of the glycoside conversion rates of the glycoside samples prepared in the examples and comparative examples; Figure 3 Comparative graphs of skin feel tests for glycoside emulsifiers in the examples and comparative examples; Figure 4 Comparison of skin feel test results for Example 1 and commercially available products in body lotion formulations; Figure 5 Polarized light micrograph of a blank body lotion; Figure 6 A polarized light micrograph of the body lotion from Example 1; Figure 7 A polarized light micrograph of a commercially available body lotion (product 1); Figure 8 Polarized light micrograph of a commercially available body lotion. Detailed Implementation

[0037] To better illustrate the purpose, technical solution, and advantages of the present invention, the present invention will be further described below in conjunction with the accompanying drawings and specific embodiments.

[0038] In the following examples and comparative examples, unless otherwise specified, the experimental methods used are conventional methods, and the materials and reagents used are commercially available unless otherwise specified. Furthermore, the raw materials used in each parallel experiment are the same.

[0039] Example 1: A glycoside emulsifier and its preparation method This embodiment provides a method for preparing a glycoside emulsifier, including the following steps: 1) Weigh 1.5 mol of cetyl alcohol into a three-necked flask and heat to 60°C until the whole substance is molten; 2) Weigh out the amount of Ce-ZrO2-SO4 added as solid superacid. 2- Add 0.5% (mSiO2 by mass of alkyl alcohol and xylose) and 10.28g 3A (2% by mass of alkyl alcohol and xylose) molecular sieve, turn on the stirrer, and disperse the solid particles evenly in the alkyl alcohol. 3) Weigh 1 mol of xylose and add it to a three-necked flask. Heat to 120°C, assemble a condenser, and collect the water produced in the reaction. Set the vacuum pressure to -0.08±0.005MPa and react for 8 hours to obtain the reaction material. 4) The reactants are filtered while hot (using a 1000-mesh filter) to separate and remove the solid superacid Ce-ZrO2-SO4. 2- @mSiO2 and 3A molecular sieves are used to prepare glycosides, namely cetyl xyloside (i.e., Example 1a). 5) Weigh 80g of cetyl xyloside and 20g of sucrose oleate, melt them at 60℃ and mix them evenly, then granulate them to obtain the glycoside emulsifier.

[0040] The liquid chromatography spectrum of cetyl xyloside is as follows: Figure 1 As shown.

[0041] Example 2: A glycoside emulsifier and its preparation method This embodiment provides a method for preparing a glycoside emulsifier, including the following steps: 1) Weigh 1.2 mol stearyl alcohol into a three-necked flask and heat to 65°C until the whole thing is molten; 2) Weigh out the solid superacid Nd-ZrO2-SO4 2-Add 1% mSiO2 (1% by mass of alkyl alcohol and sugar) and 10.28g 3A molecular sieve (3% by mass of alkyl alcohol and sugar), turn on the stirrer, and disperse the solid particles evenly in the alkyl alcohol. 3) Weigh 1 mol of glucose and add it to a three-necked flask. Heat to 125°C, assemble a condenser, and collect the water produced in the reaction. Set the vacuum pressure to -0.08±0.005 MPa and react for 6 hours to obtain the reaction mixture. 4) The reactants are filtered while hot (using a 1000-mesh filter) to separate and remove the solid superacid Nd-ZrO2-SO4. 2- @mSiO2 and 3A molecular sieve, glycosides can be obtained; 5) Weigh 90g of glycoside and 10g of sucrose laurate, melt them at 70℃ and mix them evenly, then granulate them to obtain the glycoside emulsifier.

[0042] Example 3: A glycoside emulsifier and its preparation method This embodiment provides a method for preparing a glycoside emulsifier, including the following steps: 1) Weigh 1.1 mol of behenol into a three-necked flask and heat to 90°C until the whole thing is molten; 2) Weigh out the solid superacid Sc-ZrO2-SO4. 2- @mSiO2 (0.1% of the mass of alkyl alcohol and sugar) and 10.28g 3A molecular sieve (4% of the mass of alkyl alcohol and sugar), turn on the stirrer to make the solid particles uniformly dispersed in the alkyl alcohol; 3) Weigh 1 mol of maltose and add it to a three-necked flask. Heat to 130°C, assemble a condenser, and collect the water produced in the reaction. Set the vacuum pressure to -0.08±0.005 MPa and react for 10 hours to obtain the reactants. 4) Filter the reactants while hot (using a 1000-mesh filter) to separate and remove the solid superacid Sc-ZrO2-SO4. 2- @mSiO2 and 3A molecular sieve, glycosides can be obtained; 5) Weigh 60g of glycoside, 20g of sucrose palmitate and 20g of sucrose behenate, melt them at 100℃ and mix them evenly, then granulate them to obtain the glycoside emulsifier.

[0043] Example 4: A glycoside emulsifier and its preparation method This embodiment provides a method for preparing a glycoside emulsifier, including the following steps: 1) Weigh 0.5 mol cetyl alcohol and 1 mol stearyl alcohol into a three-necked flask, heat to 85°C, until the whole mixture is molten; 2) Weigh out the amount of Ce-ZrO2-SO4 added as solid superacid. 2-@mSiO2 (2% by mass of alkyl alcohol and sugar) and 10.28g 3A molecular sieve (10% by mass of alkyl alcohol and sugar), turn on the stirrer to make the solid particles evenly dispersed in the alkyl alcohol; 3) Weigh 1 mol of xylose and add it to a three-necked flask. Heat to 115℃, assemble a condenser, and collect the water produced in the reaction. Set the vacuum pressure to -0.08±0.005MPa and react for 8.5 h to obtain the reactants. 4) The reactants are filtered while hot (using a 1000-mesh filter) to separate and remove the solid superacid Ce-ZrO2-SO4. 2- @mSiO2 and 3A molecular sieve, glycosides can be obtained; 5) Weigh 75g of glycoside and 25g of sucrose stearate, melt them at 85℃ and mix them evenly, then granulate them to obtain the glycoside emulsifier.

[0044] Example 5: A glycoside emulsifier and its preparation method This embodiment provides a method for preparing a glycoside emulsifier, including the following steps: 1) Weigh 0.8 mol of peanut alcohol and 0.8 mol of behenol into a three-necked flask, heat to 85°C, until the whole mixture is molten; 2) Weigh out the amount of Ce-ZrO2-SO4 added as solid superacid. 2- @mSiO2 (2% by mass of alkyl alcohol and sugar) and 10.28g 3A molecular sieve (10% by mass of alkyl alcohol and sugar), turn on the stirrer to make the solid particles evenly dispersed in the alkyl alcohol; 3) Weigh 1 mol of fructose and add it to a three-necked flask. Heat to 115℃, assemble a condenser, and collect the water produced in the reaction. Set the vacuum pressure to -0.08±0.005MPa and react for 9 hours to obtain the reactants. 4) The reactants are filtered while hot (using a 1000-mesh filter) to separate and remove the solid superacid Ce-ZrO2-SO4. 2- @mSiO2 and 3A molecular sieve, glycosides can be obtained; 5) Weigh 55g of glycoside, 15g of sucrose stearate, 15g of sucrose distearate, and 15g of sucrose tristearate, melt them at 85℃ and mix them evenly, then granulate them to obtain the glycoside emulsifier.

[0045] Example 6: A glycoside emulsifier and its preparation method Compared with Example 1, Example 6 differs in that the amount of cetyl alcohol is increased to 1.8 mol, the amount of solid superacid is reduced to 0.1% of the mass of alkyl alcohol and sugar, and the amount of 3A molecular sieve is increased to 10% of the mass of alkyl alcohol and sugar, thus obtaining a glycoside, namely cetyl xyloside; at the same time, the amount of glycoside is increased to 95 g and the amount of sucrose oleate is reduced to 5 g, thus obtaining a glycoside emulsifier.

[0046] Example 7: A glycoside emulsifier and its preparation method Compared with Example 1, the difference in Example 7 is that the amount of cetyl alcohol is reduced to 1.1 mol, the amount of solid superacid is increased to 2% of the mass of alkyl alcohol and sugar, and the amount of 3A molecular sieve is reduced to 1% of the mass of alkyl alcohol and sugar, thus obtaining a glycoside, namely cetyl xyloside; at the same time, the amount of glycoside is reduced to 50 g, and the amount of sucrose oleate is increased to 50 g, thus obtaining a glycoside emulsifier.

[0047] Example 8: A glycoside emulsifier and its preparation method Compared with Example 1, the difference in Example 8 is that the amount of cetyl xyloside is increased to 95g and the amount of sucrose oleate is reduced to 5g, thus obtaining a glycoside emulsifier.

[0048] Example 9: A glycoside emulsifier and its preparation method Compared with Example 1, the difference in Example 9 is that the amount of cetyl xyloside is reduced to 50g and the amount of sucrose oleate is increased to 50g, thus obtaining a glycoside emulsifier.

[0049] Example 10: A glycoside emulsifier and its preparation method Compared with Example 1, the difference in Example 10 is that 20g of sucrose oleate is replaced with 10g of sucrose stearate and 10g of sucrose distearate, thus obtaining a glycoside emulsifier.

[0050] Comparative Example 1 Compared with Example 1, the difference in Comparative Example 1 is that the amount of cetyl alcohol was reduced to 1.0 mol, and the glycoside was prepared by the same method as in Example 1.

[0051] Comparative Example 2 Compared with Example 1, the difference in Comparative Example 2 is that the amount of solid superacid is reduced by 0.01% of the mass of alkyl alcohol and sugar, and the amount of 3A molecular sieve is reduced by 0.1% of the mass of alkyl alcohol and sugar. The glycoside is prepared by the same method as in Example 1.

[0052] Comparative Example 3 Compared with Example 1, the difference in Comparative Example 3 is that cetyl alcohol was replaced with decanol (carbon chain length C10) to prepare glycosides. The preparation method of glycosides and the formulation of glycoside emulsifiers are the same as in Example 1.

[0053] Comparative Example 4 Compared with Example 1, the difference in Comparative Example 4 is that xylose was replaced with sucrose to obtain glycosides. The preparation method of the glycosides and the formulation of the glycoside emulsifier are the same as those in Example 1.

[0054] Comparative Example 5 The difference between Comparative Example 5 and Example 1 is that the solid superacid Ce-ZrO2-SO4 was used. 2- @mSiO2 is replaced with traditional solid superacid SO4. 2- / ZrO2 was used to prepare glycosides. The preparation method of glycosides and the formulation of glycoside emulsifiers were the same as in Example 1.

[0055] Comparative Example 6 Compared with Example 1, the difference in Comparative Example 6 is that sucrose oleate is replaced with maltose oleate, while the preparation method of the glycoside and the formulation of the glycoside emulsifier are the same as in Example 1.

[0056] Comparative Example 7 Compared with Example 1, the difference in Comparative Example 7 is that the amount of cetyl xyloside was reduced to 40g and the amount of sucrose oleate was increased to 60g, thus obtaining the comparative emulsifier sample.

[0057] Comparative Example 8 Compared with Example 1, the difference in Comparative Example 8 is that the amount of cetyl xyloside is increased to 96g and the amount of sucrose oleate is reduced to 4g, thus obtaining the comparative emulsifier sample.

[0058] Experimental Example 1: Glycoside Conversion Rate The glycoside conversion rate of the glycosides in Examples 1-7 and Comparative Examples 1-5 was tested.

[0059] High-performance liquid chromatography (HPLC) is the most mainstream and reliable quantitative tool for detecting glycoside conversion. Its core principle is to use the differences in physicochemical properties (such as polarity) between reactants (glycosyl donors / alkyl alcohol acceptors) and products (alkyl glycosides) to achieve separation on a chromatographic column. Then, the peak area of ​​each component is measured by an evaporative light scattering detector, and the conversion rate is calculated by the area normalization method.

[0060] First, a suitable HPLC analytical method is established, and the elution times of each component (starting material and target glycoside) are determined using standards. After the glycosylation reaction is completed, a small amount of sample is taken, diluted with methanol, and then injected for HPLC analysis.

[0061] Conversion rate (%) = [Product peak area / (Product peak area + Remaining raw material peak area)] × 100%, which can be used to calculate the conversion rate of glycosides.

[0062] The glycoside conversion rates of Examples 1-7 and Comparative Examples 1-5 are briefly shown in Table 1: Table 1 The comparison results of glycoside conversion rates in the examples and comparative examples are as follows: Figure 1 As shown.

[0063] Depend on Figure 2 The following conclusions can be drawn: When the novel solid superacid catalyst preferred by the present invention is used (Examples 1-7), the glycoside conversion rate (75%-85%) is significantly higher than that of the comparative sample (7%-20%) using conventional catalysts or deviating from the scope defined by the present invention.

[0064] However, it should be noted that the improved glycoside conversion rate is mainly due to the choice of catalyst, rather than the emulsifier composition itself that this invention aims to protect. Even when using glycosides with lower conversion rates (such as 15% of Comparative Example 5) for compounding, as long as the ratio of glycoside to sucrose ester is within the range defined by this invention (80:20), a better emulsification effect and skin feel than Comparative Examples 1-4 and 6-8 can still be obtained.

[0065] Experimental Example 2: Emulsifying Ability The emulsifying ability of the glycoside emulsifiers in the test examples and comparative examples was evaluated, and the stability of the emulsified samples was tracked. If the sample was stable, it was marked with "√", and if the sample was unstable, it was marked with "×".

[0066] The emulsifying ability test formulations are shown in Table 2: Table 2 The emulsifier samples include: Examples 1-10 and Comparative Examples 1-8; Oil samples included: mineral oil - 26# white oil (mineral oil), GTCC (caprylic / capric triglyceride), AB (C12-15 alcohol benzoate), ISIS (isostearyl isostearate); vegetable oils - olive oil, sunflower oil, macadamia nut oil, shea butter; silicone oils - DOW CORNING 200® 350CST, XIAMETER® PMX-200 / 100CS, XIAMETER® PMX-0345.

[0067] Emulsification test process: Weigh component A and heat it to 80°C; weigh component B and heat it to 75°C; add component A to component B and homogenize at 3000 rpm for 10 minutes.

[0068] Stability criteria: If the sample does not separate into layers or precipitate, it can be considered stable; otherwise, the sample is unstable.

[0069] The results of the emulsifying ability tests of glycoside emulsifiers for different oils in the examples and comparative examples are shown in Table 3: Table 3. Comparison of emulsification stability of different oils by glycoside emulsifiers in the examples and comparative examples. The following conclusions can be drawn from Table 3: The samples prepared in the examples (glycoside to sucrose ester ratio in the range of 50-95:5-50) exhibited good emulsifying ability and emulsion stability for various types of oils. However, Comparative Example 7 (glycoside 40%: sucrose ester 60%), Comparative Example 8 (glycoside 96%: sucrose ester 4%), and Comparative Example 3 (glycoside prepared using short-chain alcohols) failed to achieve broad-spectrum emulsification. This indicates that excellent emulsifying effects can only be obtained when the glycoside to sucrose ester ratio is within the specific range defined in this invention.

[0070] Experimental Example 3: Skin Feel Test The skin feel of the glycoside emulsifiers in the test examples and comparative examples was sampled using a simplified formulation framework, and the skin feel was evaluated through testing.

[0071] The testing method for skin feel evaluation is as follows: 1. Recruit 20 volunteers aged 25-50, with a male-to-female ratio of 1:1; 2. Volunteers conducted skin feel tests in the same environment using the same methods, and scored the skin feel on three dimensions: "lightweight", "adherent to skin", and "hydrating", using a 10-point scale. 3. Samples were distributed randomly, and each volunteer tried 6 samples, with a 5-minute interval between each trial.

[0072] 4. Collect volunteer ratings, remove the highest and lowest scores, calculate the average, and obtain the final score.

[0073] The higher the score, the more "lightweight", "skin-adhering", and "hydrating" the skin feels.

[0074] The simplified recipe framework is shown in Table 4: Table 4. Skin feel test formulations for glycoside emulsifiers in the examples and comparative examples. Formulation process: Weigh out component A and heat it to 80°C; weigh out component B and heat it to 85°C; add component B to component A and homogenize at 3000 rpm for 10 minutes; cool down to 45°C and add component C in sequence, stirring until homogeneous.

[0075] The results of the skin feel test are shown in Table 5: Table 5. Comparison of skin feel tests for glycoside emulsifiers in the examples and comparative examples. The skin feel test results of the examples and comparative examples of glycoside emulsifiers are as follows: Figure 3 As shown.

[0076] Depend on Figure 3 The following conclusions can be drawn: (1) The ratio is key: The skin feel scores of Examples 1-10 (glycosides 50-95%) (7.4-9.3) were significantly higher than those of Comparative Example 7 (glycosides 40%, score 3.8-4.0) and Comparative Example 8 (glycosides 96%, score 4.6-4.9). This proves that only when the ratio of glycosides to sucrose esters is within the range of 50-95:5-50 specified in this invention can excellent skin feel be obtained.

[0077] (2) Importance of Glycoside Purity: Comparative Example 5 used the conventional catalyst SO4²⁻ / ZrO2, and its glycoside conversion rate was only 15% (see Table 1). The product contained a large amount of unreacted cetyl alcohol (oily, heavy fatty alcohol), so its skin feel score after compounding (2.8 / 2.8 / 2.9) was much lower than that of Example 1 (8.7 / 8.5 / 8.8). This shows that to obtain excellent skin feel, the glycoside needs to have sufficiently high purity. The novel catalyst preferred in this invention can achieve a high conversion rate (>75%), thereby obtaining high-purity glycosides.

[0078] (3) The compounding effect does not depend on a specific catalyst: Those skilled in the art know that conventional methods such as extending the reaction time, increasing the reaction temperature, increasing the amount of catalyst, and using other known solid acid catalysts can also improve the glycoside conversion rate to a level comparable to that of this invention. This invention uses a compounding of glycosides and sucrose esters to achieve excellent skin feel.

[0079] Experimental Example 4: Application of Glycoside Emulsifiers in Body Lotions The glycoside emulsifier provided by this invention can be used in ointments, creams, and lotions in cosmetics. It has the basic ability to emulsify oils and provides a light, skin-friendly, and moisturizing special skin feel.

[0080] Taking the sample from Example 1 as an example, it was added to the body lotion formula and compared with similar commercially available emulsifiers in terms of emulsification stability, skin feel, and liquid crystal structure observation.

[0081] Commercially available product 1: Cetearyl glucoside.

[0082] Product 2: Sucrose stearate.

[0083] The test formulations are shown in Table 6: Table 6 Body Lotion Formulas The formulation process for the above-mentioned body lotion is as follows: S1: Pre-prepare Group C, mix, stir and dissolve evenly, set aside; Pre-prepare Group D: mix, stir and heat to 50-60℃, dissolve thoroughly and evenly, cool to room temperature, set aside. S2: Group A, after the powder is evenly dispersed in polyol, add it to water, stir and heat to 80-82℃, homogenize for 1-3 minutes until completely dissolved and uniform, keep warm for 20-30 minutes, defoam, and set aside; S3: Group B, mix and heat to 80-82℃, stir to melt into liquid, keep warm, and set aside (avoid prolonged heating). S4: Turn on the homogenizer, slowly add group B to group A, homogenize for 3-5 minutes until completely emulsified and uniform, defoam and then cool (be careful to observe whether the oil is completely emulsified). S5: Cool to 70-75℃, add pre-dissolved group C, homogenize for 1-2 minutes until uniform, stir and cool; S6: Cool down to below 45℃, add group D, and stir thoroughly. S7: Take a sample, test it, adjust the pH (10% aqueous solution) to 6-7, and discharge the material after it passes the test.

[0084] The test results for emulsion stability are shown in Table 7: Table 7. Emulsification stability results of Example 1 and commercially available products in body lotion. Conclusion: The glycoside emulsifier provided by this invention has better emulsifying ability than commercially available products.

[0085] The comparison results of the skin feel test are shown in Table 8: Table 8 Skin Feel Test The results of the skin feel test are as follows Figure 4 As shown.

[0086] Conclusion: Compared with commercially available products, the glycoside emulsifiers provided by this invention can bring a light, skin-friendly, and moisturizing skin feel to the formulation.

[0087] Under the same conditions, the liquid crystal structure of four samples—blank body lotion, body lotion containing Example 1, body lotion containing commercially available product 1, and body lotion containing commercially available product 2—was observed using a polarizing microscope at a magnification of 200x.

[0088] The microstructure of a blank body lotion is as follows: Figure 5 As shown; The microstructure of the body lotion containing Example 1 is as follows Figure 6 As shown; The microstructure of commercially available body lotion 1, such as Figure 7 As shown; Microstructure of commercially available body lotion 2, such as Figure 8 As shown.

[0089] Depend on Figures 5-8 It can be seen that the body lotion containing Example 1 has a more obvious effect.

[0090] Conclusion: Compared with commercially available products, the glycoside emulsifiers provided by this invention have a better liquid crystal structure when used in cosmetics, indicating superior performance in terms of physicochemical stability, controlled release, and moisturizing properties.

[0091] Finally, it should be noted that the above embodiments are only used to illustrate the technical solutions of the present invention and are not intended to limit the scope of protection of the present invention. Although the present invention has been described in detail with reference to preferred embodiments, those skilled in the art should understand that modifications or equivalent substitutions can be made to the technical solutions of the present invention without departing from the essence and scope of the technical solutions of the present invention.

Claims

1. A glycoside emulsifier, characterized in that, The glycoside emulsifier is composed of glycosides and sucrose esters; Based on a total mass of 100 parts of the glycoside emulsifier, the glycoside is 50-95 parts by mass and the sucrose ester is 5-50 parts by mass; The glycosides include at least one of alkyl glucoside, alkyl xylose, alkyl maltose, alkyl fructoside, alkyl galactoside, and alkyl mannoside, wherein the alkyl group is C12 to C22.

2. The glycoside emulsifier as described in claim 1, characterized in that, The glycoside is at least one of cetearyl xyloside, cetearyl glucoside, cetearyl xyloside, cetearyl glucoside, stearyl xyloside, stearyl glucoside, arachidyl xyloside, arachidyl glucoside, behenyl xyloside, and behenyl glucoside.

3. The glycoside emulsifier as described in claim 1, characterized in that, The sucrose esters include at least one of the following: sucrose polysaccharide, sucrose polycotyl oleate, sucrose polystearate, sucrose polyoleate, sucrose polylinoleate, sucrose polylaurate, sucrose hexasucrate, sucrose hexapalmitate, sucrose hexastearate, sucrose myristate, sucrose tetraisostearate, sucrose pentasucrate, sucrose distearate, sucrose dilaurate, sucrose tristearate, sucrose trisaurate, sucrose stearate, sucrose oleate, sucrose laurate, sucrose palmitate, sucrose cocoate, and sucrose behenate.

4. The glycoside emulsifier as described in claim 3, characterized in that, The sucrose ester is at least one of sucrose stearate, sucrose oleate, sucrose laurate, sucrose palmitate, and sucrose behenate.

5. The method for preparing the glycoside emulsifier according to any one of claims 1 to 4, characterized in that, Weigh out the glycosides and sucrose esters according to the above-mentioned mass proportions, melt and mix them evenly at a temperature of 65~120℃, and then granulate them to obtain glycoside emulsifiers.

6. The method for preparing the glycoside emulsifier as described in claim 5, characterized in that, The method for preparing the glycoside includes the following steps: 1) Weigh out the alkyl alcohol and heat it to 50~100℃ until the alkyl alcohol is completely molten; 2) Weigh the solid superacid catalyst and 3A molecular sieve, disperse them in a molten alkyl alcohol, and obtain a mixture; 3) Weigh the sugar, add it to the mixture, and heat it to 90~150℃ to react and obtain the reaction material; 4) The reactants are filtered to separate and remove the solid superacid catalyst and 3A molecular sieve, and glycosides are obtained.

7. The method for preparing the glycoside emulsifier as described in claim 6, characterized in that, The alkyl alcohol is a C12-C22 alcohol; And / or, the sugar is at least one of glucose, xylose, maltose, fructose, galactose, and mannose; And / or, the solid superacid catalyst comprises X-ZrO2-SO4 2- @mSiO2.

8. The method for preparing the glycoside emulsifier as described in claim 6, characterized in that, The molar ratio of the alkyl alcohol to the sugar is (1.1~1.8):1; And / or, the amount of the solid superacid catalyst added is 0.1% to 2% of the total mass of the alkyl alcohol and sugar; And / or, the amount of the 3A molecular sieve added is 1% to 10% of the total mass of the alkyl alcohol and sugar.

9. The use of the glycoside emulsifier as described in any one of claims 1 to 4 in the preparation of cosmetics.

10. A cosmetic product, characterized in that, The cosmetic product includes glycoside emulsifiers at a mass percentage of 1-10 wt%.

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