High-hydrophilicity composite high polyglycerol fatty acid ester, preparation method and application of high-hydrophilicity composite high polyglycerol fatty acid ester

Abstract

The invention relates to a high-hydrophilicity composite high polyglycerol fatty acid ester, a preparation method and application thereof, the high-hydrophilicity composite high polyglycerol fatty acid ester comprises the following structural units: a polyglycerol skeleton, the polymerization degree n = 8-10; fatty acid ester connected to polyglycerol hydroxyl; the molar ratio of the polyglycerol to the fatty acid ester is 1: (1.1-1.2); the mPEG chain is connected through an ester bond, and the molar ratio of the polyglycerol to the mPEG is 1: (1.5-3.0). According to the invention, a high-polymerization-degree polyglycerol skeleton (n = 8-10) and quaternary fatty acid are compounded (caprylic acid / capric acid / branched chain isocapric acid / linoleic acid), and mPEG directional grafting is combined, so that the prepared polyglycerol fatty acid ester has ultrahigh hydrophilicity, and the HLB (Hydrophile Lipophile Balance) is 18-20; the isodecanoic acid branched chain and the linoleic acid double bond inhibit crystallization separation, and the problem that a traditional emulsifier loses efficacy after being stored for a long time is solved.

Description

Technical Field

[0001] The invention relates to a highly hydrophilic composite high-polyglycerol fatty acid ester, a preparation method and application thereof, and belongs to the field of food additives. Background Art

[0002] Emulsifiers are a key type of food additive. They perform whipping and emulsification in the oil-water-solid three-phase system of foods like dairy products, baked goods, and condiments, maintaining the desired stability and imparting textures ranging from fluffiness to smoothness, crispness, and a delicate texture. Currently, the main high-HLB food emulsifiers are Tween and sucrose esters. While the Tween series offers low production costs and mature manufacturing processes, the use of ethylene oxide and glycidol in its production process carries the risk of dioxin production, which does not meet modern food health requirements. The current mainstream production process for sucrose esters involves fatty acid methyl esters, which poses environmental risks. Furthermore, if these products are not purified at the end of production, they can pose health risks. Sucrose esters produced using a complete and sophisticated manufacturing process can cost up to 200 yuan per kilogram, prohibiting large-scale application in the food industry.

[0003] Polyglycerol fatty acid esters can form a range of HLB values ​​depending on the degree of glycerol polymerization, fatty acid length, and degree of esterification, forming a comprehensive food whipping and emulsification system. Among the polyglycerol fatty acid ester series, monoesterified polyglycerol fatty acid esters exhibit excellent emulsifying activity. Higher degrees of glycerol polymerization increase hydrophilicity, while longer fatty acid carbon chains increase lipophilicity. The fatty acids used to make polyglycerol fatty acid esters are naturally derived and have a fixed lipophilicity. Therefore, their hydrophilicity determines the quality and stability of foods in oil-water-solid three-phase systems or oil-water-gas-solid four-phase systems. Furthermore, this hydrophilicity ensures the emulsifier's viability in ambient water. The traditional method for preparing decaglycerol long-chain monofatty acid esters involves direct esterification of decaglycerol with the corresponding fatty acid. However, only polyglycerols with a glycerol degree of polymerization of less than 4 are linear. Polyglycerols with a glycerol degree of polymerization of 4 or greater, such as decaglycerol, tend to form cyclic or branched structures due to their higher degree of polymerization, reducing the hydrophilicity of the decaglycerol long-chain monofatty acid esters. Therefore, it is urgent to develop a kind of high polyglycerol fatty acid ester with stronger hydrophilicity. Summary of the Invention

[0004] The present invention provides a highly hydrophilic composite high-polyglycerol fatty acid ester, a preparation method and use thereof, which solve the problems that the existing high-polyglycerol fatty acid ester has a high degree of polymerization and is prone to forming a ring structure or a branched structure, thereby reducing the hydrophilicity of decaglycerol long-chain monofatty acid ester.

[0005] In order to solve the above technical problems, the technical solution adopted by the present invention is:

[0006] A highly hydrophilic composite high-polyglycerol fatty acid ester comprising the following structural units:

[0007] Polyglycerol backbone, degree of polymerization n=8-10;

[0008] Fatty acid ester connected to the polyglycerol hydroxyl group; the molar ratio of the polyglycerol to the fatty acid ester is 1:1.1-1.2;

[0009] The mPEG chains are connected by ester bonds, and the molar ratio of polyglycerol to mPEG is 1:1.5-3.0.

[0010] Furthermore, preferably, the fatty acids include caprylic acid, capric acid, isodecanoic acid and linoleic acid, and the mass ratio of caprylic acid: capric acid: isodecanoic acid, linoleic acid is 6-7: 2-3: 1-2: 0.1-0.3.

[0011] Furthermore, preferably, the molecular weight of the mPEG is 400-800 Da.

[0012] The preparation method of the highly hydrophilic composite high polyglycerol fatty acid ester of the present invention comprises the following steps:

[0013] (1) Catalytic esterification: Polyglycerol and caprylic acid, capric acid, and isodecanoic acid are catalyzed by a catalyst and heated to 180°C under nitrogen protection for 2 hours until the acid value is reduced to ≤10 mg KOH / g;

[0014] (2) PEG grafting: react the product of step (1) with mPEG-COOH and an antioxidant at 150-160° C. for 1-2 hours, controlling the acid value to be ≤15 mg KOH / g;

[0015] (3) Add linoleic acid, raise the temperature to 200°C, and vacuum dehydrate (-0.095 MPa) for 1 hour until the acid value is ≤5 mgKOH / g;

[0016] (4) Cool to 80°C, neutralize the catalyst with citric acid aqueous solution, wash with water to remove salt, and dehydrate under reduced pressure to obtain a light yellow viscous product.

[0017] Furthermore, preferably: in step (1), the catalyst is sodium acetate, and the amount added is 0.3-0.5% of the total mass of the reactants.

[0018] Furthermore, preferably, the antioxidant is rosemary extract, and the added amount is 0.01-0.02% of the total mass of the reactants.

[0019] The present invention also provides an emulsion composition comprising the highly hydrophilic composite polyglycerol fatty acid ester prepared by the present invention, wherein the mass fraction of the highly hydrophilic composite polyglycerol fatty acid ester in the composition is 0.1-10%.

[0020] The present invention also provides the use of highly hydrophilic composite polyglycerol fatty acid ester in the preparation of cosmetics, pharmaceutical carriers or food emulsifiers.

[0021] Beneficial effects of the present invention:

[0022] The present invention combines a high polymerization degree polyglycerol skeleton (n=8-10) with a tetrabasic fatty acid

[0023] (caprylic acid / capric acid / branched isodecanoic acid / linoleic acid), combined with mPEG directional grafting, the prepared polyglycerol fatty acid ester has ultra-high hydrophilicity, HLB = 18-20); excellent low temperature stability

[0024] :Isodecanoic acid side chain + linoleic acid double bond inhibits crystallization and solves the problem of traditional emulsifiers becoming ineffective after long-term storage.

[0025] The polyglycerol of the present invention provides a polyhydroxy backbone to which fatty acid esters are attached. On the one hand, the hydrophobicity of fatty acids and the hydrophilicity of polyglycerol are balanced to give the product good emulsifying properties, enabling the oil phase to be dispersed into the aqueous phase. On the other hand, the increase in fatty acid esters can enhance affinity with the oil phase and improve the emulsification effect. At the same time, the fatty acid esterification reaction can increase the reactivity of polyglycerol, facilitating subsequent grafting with mPEG.

[0026] The molar ratio of polyglycerol to fatty acid ester is precisely controlled at 1:1.1-1.2, and the fatty acids include caprylic acid, capric acid, isodecanoic acid and linoleic acid. The esterification of multiple types of fatty acids can balance the lipophilicity and hydrophilicity of the product, improve the emulsification performance, achieve good emulsification of different oil phase substances, and broaden the application fields.

[0027] When mPEG is grafted onto polyglycerol fatty acid esters, its hydrophilicity disrupts the original relative balance between lipophilicity and hydrophilicity, significantly increasing the product's hydrophilicity and enabling better solubility in water, playing roles in emulsification and solubilization. Furthermore, the long mPEG chain increases molecular flexibility, facilitating interaction with diverse substances and enhancing the product's adaptability and functional performance in complex systems. Linoleic acid, an unsaturated fatty acid containing double bonds, imparts special properties to the product. It can participate in the emulsification process to a certain extent, synergizing with saturated fatty acid esters to optimize emulsion stability. It may also interact slightly with mPEG, further adjusting the product's molecular conformation and enhancing its overall performance, making it more advantageous in specific application scenarios. DETAILED DESCRIPTION

[0028] The following will clearly and completely describe the technical solutions of the present invention in conjunction with the embodiments of the present invention. Obviously, the embodiments described are only part of the embodiments of the present invention, not all of the embodiments. All other embodiments obtained by ordinary technicians in this field based on the embodiments of the present invention without creative work are not included.

[0029] Example 1

[0030] A highly hydrophilic composite high-polyglycerol fatty acid ester comprising the following structural units:

[0031] Polyglycerol backbone, degree of polymerization n=10;

[0032] A fatty acid ester connected to a polyglycerol hydroxyl group; the molar ratio of the polyglycerol to the fatty acid ester is 1:1.1;

[0033] The mPEG chains are connected by ester bonds, and the molar ratio of polyglycerol to mPEG is 1:3.0.

[0034] The fatty acids include caprylic acid, capric acid, isodecanoic acid and linoleic acid, and the mass ratio of caprylic acid: capric acid: isodecanoic acid, linoleic acid is 6:2:2:0.1.

[0035] The molecular weight of mPEG is 600 Da.

[0036] The preparation method thereof comprises the following steps:

[0037] (1) Catalytic esterification: Polyglycerol and caprylic acid, capric acid, and isodecanoic acid are catalyzed by a catalyst and heated to 180°C under nitrogen protection for 2 hours until the acid value is reduced to ≤10 mg KOH / g. The catalyst is sodium acetate, and the addition amount is 0.5% of the total mass of the reactants.

[0038] (2) PEG grafting: the product of step (1) was reacted with mPEG-COOH and an antioxidant at 160° C. for 1.5 hours, with the acid value controlled to be ≤15 mg KOH / g. The antioxidant was rosemary extract, and the addition amount was 0.01% of the total mass of the reactants;

[0039] (3) Add linoleic acid, raise the temperature to 200°C, and vacuum dehydrate (-0.095 MPa) for 1 hour until the acid value is ≤5 mgKOH / g;

[0040] (4) Cool to 80°C, neutralize the catalyst with citric acid aqueous solution, wash with water to remove salt, and dehydrate under reduced pressure to obtain a light yellow viscous product.

[0041] Example 2

[0042] A highly hydrophilic composite high-polyglycerol fatty acid ester comprising the following structural units:

[0043] Polyglycerol backbone, degree of polymerization n=10;

[0044] A fatty acid ester connected to a polyglycerol hydroxyl group; the molar ratio of the polyglycerol to the fatty acid ester is 1:1.2;

[0045] The mPEG chains are connected by ester bonds, and the molar ratio of polyglycerol to mPEG is 1:2.0.

[0046] Furthermore, preferably, the fatty acids include caprylic acid, capric acid, isodecanoic acid and linoleic acid, and the mass ratio of caprylic acid: capric acid: isodecanoic acid, linoleic acid is 7:3:1:0.3.

[0047] The molecular weight of mPEG is 600 Da.

[0048] The preparation method thereof comprises the following steps:

[0049] (1) Catalytic esterification: Polyglycerol and caprylic acid, capric acid, and isodecanoic acid were catalyzed by a catalyst and heated to 180°C under nitrogen protection for 2 hours until the acid value dropped to ≤10 mg KOH / g. The catalyst was sodium acetate, and the addition amount was 0.4% of the total mass of the reactants.

[0050] (2) PEG grafting: the product of step (1) was reacted with mPEG-COOH and an antioxidant at 150° C. for 2 hours, with the acid value controlled to be ≤15 mg KOH / g. The antioxidant was rosemary extract, and the addition amount was 0.02% of the total mass of the reactants;

[0051] (3) Add linoleic acid, raise the temperature to 200°C, and vacuum dehydrate (-0.095 MPa) for 1 hour until the acid value is ≤5 mgKOH / g;

[0052] (4) Cool to 80°C, neutralize the catalyst with citric acid aqueous solution, wash with water to remove salt, and dehydrate under reduced pressure to obtain a light yellow viscous product.

[0053] Example 3

[0054] A highly hydrophilic composite high-polyglycerol fatty acid ester comprising the following structural units:

[0055] Polyglycerol backbone, degree of polymerization n=8;

[0056] A fatty acid ester connected to a polyglycerol hydroxyl group; the molar ratio of the polyglycerol to the fatty acid ester is 1:1.1;

[0057] The mPEG chains are connected by ester bonds, and the molar ratio of polyglycerol to mPEG is 1:1.5.

[0058] The fatty acids include caprylic acid, capric acid, isodecanoic acid and linoleic acid, and the mass ratio of caprylic acid: capric acid: isodecanoic acid, linoleic acid is 6:3:1:0.2.

[0059] The molecular weight of mPEG is 800 Da.

[0060] The preparation method thereof comprises the following steps:

[0061] (1) Catalytic esterification: Polyglycerol and caprylic acid, capric acid, and isodecanoic acid were catalyzed by a catalyst and heated to 180°C under nitrogen protection for 2 hours until the acid value dropped to ≤10 mg KOH / g. The catalyst was sodium acetate, and the addition amount was 0.3% of the total mass of the reactants.

[0062] (2) PEG grafting: the product of step (1) was reacted with mPEG-COOH and an antioxidant at 160° C. for 1 hour, with the acid value controlled to be ≤15 mg KOH / g. The antioxidant was rosemary extract, and the addition amount was 0.01% of the total mass of the reactants;

[0063] (3) Add linoleic acid, raise the temperature to 200°C, and vacuum dehydrate (-0.095 MPa) for 1 hour until the acid value is ≤5 mgKOH / g;

[0064] (4) Cool to 80°C, neutralize the catalyst with citric acid aqueous solution, wash with water to remove salt, and dehydrate under reduced pressure to obtain a light yellow viscous product.

[0065] Example 4

[0066] A highly hydrophilic composite high-polyglycerol fatty acid ester comprising the following structural units:

[0067] Polyglycerol backbone, degree of polymerization n=9;

[0068] A fatty acid ester connected to a polyglycerol hydroxyl group; the molar ratio of the polyglycerol to the fatty acid ester is 1:1.2;

[0069] The mPEG chains are connected by ester bonds, and the molar ratio of polyglycerol to mPEG is 1:2.5.

[0070] The fatty acids include caprylic acid, capric acid, isodecanoic acid and linoleic acid, and the mass ratio of caprylic acid: capric acid: isodecanoic acid, linoleic acid is 6:2:1:0.2.

[0071] The molecular weight of mPEG is 400 Da.

[0072] The preparation method thereof comprises the following steps:

[0073] (1) Catalytic esterification: Polyglycerol and caprylic acid, capric acid, and isodecanoic acid are catalyzed by a catalyst and heated to 180°C under nitrogen protection for 2 hours until the acid value is reduced to ≤10 mg KOH / g. The catalyst is sodium acetate, and the addition amount is 0.3-0.5% of the total mass of the reactants;

[0074] (2) PEG grafting: the product of step (1) was reacted with mPEG-COOH and an antioxidant at 150° C. for 1.5 hours, with the acid value controlled to be ≤15 mg KOH / g. The antioxidant was rosemary extract, and the addition amount was 0.02% of the total mass of the reactants;

[0075] (3) Add linoleic acid, raise the temperature to 200°C, and vacuum dehydrate (-0.095 MPa) for 1 hour until the acid value is ≤5 mgKOH / g;

[0076] (4) Cool to 80°C, neutralize the catalyst with citric acid aqueous solution, wash with water to remove salt, and dehydrate under reduced pressure to obtain a light yellow viscous product.

[0077] Example 5

[0078] A highly hydrophilic composite high-polyglycerol fatty acid ester comprising the following structural units:

[0079] Polyglycerol backbone, degree of polymerization n=9;

[0080] A fatty acid ester connected to a polyglycerol hydroxyl group; the molar ratio of the polyglycerol to the fatty acid ester is 1:1.1;

[0081] The mPEG chains are connected by ester bonds, and the molar ratio of polyglycerol to mPEG is 1:2.0.

[0082] The fatty acids include caprylic acid, capric acid, isodecanoic acid and linoleic acid, and the mass ratio of caprylic acid: capric acid: isodecanoic acid, linoleic acid is 7:2:1:0.1.

[0083] The molecular weight of mPEG is 600 Da.

[0084] The preparation method thereof comprises the following steps:

[0085] (1) Catalytic esterification: Polyglycerol and caprylic acid, capric acid, and isodecanoic acid are catalyzed by a catalyst and heated to 180°C under nitrogen protection for 2 hours until the acid value is reduced to ≤10 mg KOH / g. The catalyst is sodium acetate, and the addition amount is 0.3-0.5% of the total mass of the reactants;

[0086] (2) PEG grafting: the product of step (1) was reacted with mPEG and an antioxidant at 150° C. for 2 hours, with the acid value controlled to be ≤15 mg KOH / g. The antioxidant was rosemary extract, and the addition amount was 0.02% of the total mass of the reactants;

[0087] (3) Add linoleic acid, raise the temperature to 200°C, and vacuum dehydrate (-0.095 MPa) for 1 hour until the acid value is ≤5 mgKOH / g;

[0088] (4) Cool to 80°C, neutralize the catalyst with citric acid aqueous solution, wash with water to remove salt, and dehydrate under reduced pressure to obtain a light yellow viscous product.

[0089] Comparative Examples 1-3 investigate the effects of different fatty acid compositions on product indicators

[0090] It is basically the same as Example 1, except that the composition of fatty acids is different, as shown in Table 1.

[0091] Table 1 Composition of different fatty acid raw materials

[0092] Example 1 Comparative Example 1 Comparative Example 2 Comparative Example 3 bitter 6 6 6 6 Decanoic acid 2 4.1 4 2.1 Isodecanoic acid 2 0 0 2 Linoleic acid 0.1 0 0.1 0

[0093] Comparative Examples 1-3 investigate the effects of different mPEGs on product indicators

[0094] The method is basically the same as Example 1, except that the composition of mPEG is different, as shown in Table 2.

[0095] Table 2 Composition of different mPEG raw materials

[0096]

[0097]

[0098] Index determination:

[0099] 1. Calculation of HLB value of polyglycerol fatty acid ester

[0100] For nonionic polyol fatty acid esters, Griffin proposed that the HLB can be calculated using the following formula:

[0101] HLB=20×(1-S / X)

[0102] Where: S is the saponification value of the polyol fatty acid ester, and X is the acid value of the fatty acid that produces the ester.

[0103] Determination of saponification value S of polyglycerol fatty acid esters.

[0104] Reagents: 0.5 mol / L potassium hydroxide-ethanol solution, neutral anhydrous ethanol, 0.5 mol / L hydrochloric acid standard solution;

[0105] Procedure: Weigh 1.5g of sample into a 250mL iodine volumetric flask. Use a pipette to transfer 25mL of 0.5mol / L potassium hydroxide-ethanol solution. Place the iodine volumetric flask in a 95°C constant-temperature water bath and reflux for 60 minutes. Remove the flask and clean the inner wall and lower end of the condenser with 20mL of neutral anhydrous ethanol. Add 5 drops of phenolphthalein indicator. Add 0.5mol / L hydrochloric acid standard solution until the color turns pink. If the color does not fade for 30 seconds, perform a blank test according to the above steps.

[0106] Calculation formula: S = (V 0 - V) × C × 56.11 / m

[0107] Where: C—concentration of hydrochloric acid standard solution (mol / L), V0—blank,

[0108] V is the volume of hydrochloric acid standard solution consumed by the sample (mL), and m is the mass of the sample (g).

[0109] Determination of acid value X of polyglycerol fatty acid esters.

[0110] Reagents: anhydrous ethanol, 0.1 mol / L potassium hydroxide-ethanol standard solution, 10 g / L phenolphthalein indicator solution.

[0111] Steps: Weigh 5g of sample into a 250mL conical flask, use a measuring cylinder to measure 60mL of neutral ethanol (take an appropriate amount of anhydrous ethanol, add 2-3 drops of phenolphthalein, and add 0.1mol / L potassium hydroxide solution until it turns pink), heat to dissolve, add 2-3 drops of phenolphthalein indicator, and add 0.1mol / L potassium hydroxide-ethanol standard solution until it turns pink, and keep it without fading for 30s.

[0112] Calculation formula: X = C × V × 56.11 / m

[0113] Where: V—volume of potassium hydroxide standard solution consumed by the sample (mL),

[0114] C is the concentration of potassium hydroxide standard solution (mol / L), m is the mass of the sample (g).

[0115] 2. Emulsification performance determination:

[0116] Prepare 0.1% aqueous solutions of C10, C12, and C14, respectively. Transfer 40 mL of these solutions and 40 mL of liquid paraffin into a 100 mL stoppered graduated cylinder. Tightly stopper the cylinder and place it in a 40°C water bath for 3 minutes. Vigorously shake the stoppered graduated cylinder 10 times. Let it sit for 60 seconds, repeat this process three times, and immediately place it on the laboratory bench. Use a stopwatch to time the separation of the oil and water phases in the stoppered graduated cylinder, until the aqueous phase reaches 10 mL.

[0117] 3. Foam performance determination:

[0118] Take 3 grams of the sample and dissolve it in 100 ml of water. Use a high shear machine to control the speed at 5000 r / min to whip for 3 minutes, observe the foam height, and observe the defoaming height after 24 hours.

[0119] Foam stability is calculated according to the following formula.

[0120] Foam stability / %=H / H1×100,

[0121] Where: H is the residual amount of foam, mL; H1 is the amount of foam, mL.

[0122] 4. Storage stability

[0123] Store the prepared fresh high-polyglycerol fatty acid ester at 25±1°C for 6 months. Observe the product for discoloration, stratification, and precipitation.

[0124] Specific measurement indicators are shown in Table 3.

[0125] Table 3 Effects of different raw material compositions on products

[0126]

[0127] Table 4 Product performance measurement results of different embodiments

[0128]

[0129]

[0130] As shown in Table 3, the polyglycerol fatty acid ester prepared in the present invention has ultra-high hydrophilicity (HLB = 18-20) by compounding a high-polymerization polyglycerol backbone (n = 8-10) with tetrabasic fatty acids (caprylic acid / capric acid / branched isodecanoic acid / linoleic acid) in combination with mPEG directional grafting. It also has excellent low-temperature stability: the isodecanoic acid side chains and the linoleic acid double bonds inhibit crystallization, solving the problem of long-term failure of traditional emulsifiers.

[0131] The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention. Any modifications, equivalent substitutions, improvements, etc. made within the spirit and principles of the present invention should be included in the scope of protection of the present invention.

Claims

1. A highly hydrophilic composite high polyglycerol fatty acid ester, characterized in that: Contains the following structural units: Polyglycerol backbone, degree of polymerization n=8-10; Fatty acid ester connected to the polyglycerol hydroxyl group; the molar ratio of the polyglycerol to the fatty acid ester is 1:1.1-1.2; The mPEG chains are connected by ester bonds, and the molar ratio of polyglycerol to mPEG is 1:1.5-3.

0.

2. The highly hydrophilic composite high polyglycerol fatty acid ester according to claim 1, wherein: The fatty acids include caprylic acid, capric acid, isodecanoic acid and linoleic acid, and the mass ratio of caprylic acid: capric acid: isodecanoic acid, linoleic acid is 6-7: 2-3: 1-2: 0.1-0.

3.

3. The highly hydrophilic composite high polyglycerol fatty acid ester according to claim 1, wherein: The molecular weight of the mPEG is 400-800 Da.

4. A method for preparing a highly hydrophilic composite high polyglycerol fatty acid ester according to any one of claims 1 to 3, characterized in that: The following steps are involved: (1) Catalytic esterification: Polyglycerol and caprylic acid, capric acid, and isodecanoic acid are catalyzed by a catalyst and heated to 180°C under nitrogen protection for 2 hours until the acid value is reduced to ≤10 mg KOH / g; (2) PEG grafting: react the product of step (1) with mPEG-COOH and an antioxidant at 150-160°C for 1-2 hours, controlling the acid value to be ≤15 mg KOH / g; (3) Add linoleic acid, raise the temperature to 200°C, and vacuum dehydrate (-0.095 MPa) for 1 hour until the acid value is ≤5 mg KOH / g; (4) Cool to 80°C, neutralize the catalyst with citric acid aqueous solution, wash with water to remove salt, and dehydrate under reduced pressure to obtain a light yellow viscous product.

5. The preparation method according to claim 4, wherein: The catalyst in step (1) is sodium acetate, and the added amount is 0.3-0.5% of the total mass of the reactants.

6. The preparation method according to claim 4, wherein: The antioxidant is rosemary extract, and the added amount is 0.01-0.02% of the total mass of the reactants.

7. An emulsion composition, characterized in that: The highly hydrophilic composite polyglycerol fatty acid ester prepared according to claim 4 has a mass fraction of 0.1-10% in the composition.

8. Use of the highly hydrophilic composite high polyglycerol fatty acid ester according to any one of claims 1 to 6 in the preparation of cosmetics, pharmaceutical carriers or food emulsifiers.

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