CN115260484A - Preparation method of modified tween-20 and application of modified tween-20 in preparation process of vitamin E emulsion - Google Patents
Preparation method of modified tween-20 and application of modified tween-20 in preparation process of vitamin E emulsion Download PDFInfo
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- CN115260484A CN115260484A CN202210878671.2A CN202210878671A CN115260484A CN 115260484 A CN115260484 A CN 115260484A CN 202210878671 A CN202210878671 A CN 202210878671A CN 115260484 A CN115260484 A CN 115260484A
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
- C08G65/332—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof
- C08G65/3322—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof acyclic
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- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
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Abstract
The invention provides a preparation method of modified tween-20 and application thereof in a preparation process of a vitamin E microcapsule. The preparation method of the modified tween-20 comprises the following steps: 1) Monosaccharide is used as a starting material, and oxidation reaction is carried out under the condition that sodium phosphomolybdate is used as a catalyst to obtain monosaccharide acid; 2) The monosaccharide acid and the Tween-20 are subjected to esterification reaction to obtain the modified Tween-20 product with excellent emulsifying property. The invention also provides an emulsion which is prepared by adopting the modified Tween-20 as an oily emulsifier and compounding and emulsifying the oily emulsifier and other aqueous emulsifiers in the preparation process of the vitamin E emulsion, and has high oil loading rate, wide viscosity range and stable VE content.
Description
Technical Field
The invention belongs to the technical field of vitamin E microcapsules, and particularly relates to a preparation method of modified Tween-20 and application of the modified Tween-20 in a preparation process of a vitamin E emulsion.
Background
Vitamin E is an antioxidant in human physiological functions and is also an important strong free radical scavenger. It can protect the integrity of body cells, prevent cardiovascular diseases, resist aging, enhance the immune function of the body, etc. However, vitamin E, as a fat-soluble vitamin, is difficult to apply in water-soluble products, and vitamin E can be rapidly destroyed by oxidation under alkaline, oxygen and ultraviolet conditions.
In order to make vitamin E widely applicable to the fields of food, medicine, cosmetics and the like, a microcapsule product which is stable and has good water solubility needs to be prepared. In the process of preparing vitamin E microcapsules in the market at present, the preparation of vitamin E emulsion also becomes a difficult point due to the characteristics of higher oil loading rate, stable storage and the like. The selection and application of the emulsifier in the process of preparing the vitamin E emulsion is a crucial step, and thus it is required to develop an emulsifier having superior emulsifying properties. The traditional Tween-20 emulsifier has poor emulsifying effect, and the preparation of a vitamin E product with high oil carrying rate is difficult to realize by a single emulsifier.
Disclosure of Invention
The invention aims to provide a preparation method of modified Tween-20, which takes monosaccharide as a starting material and obtains the modified Tween-20 emulsifier with excellent emulsifying property through two-step reactions of oxidation and esterification.
The invention also aims to prepare the VE emulsion by adopting the modified Tween-20 as an oily emulsifier, and the VE emulsion is compounded and emulsified with other aqueous emulsifiers to obtain the emulsion with high oil loading rate, wide viscosity range and stable VE content.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows:
the preparation process of the modified tween-20 comprises the following steps:
1) Preparation of the monosaccharide acid: weighing a certain amount of monosaccharide, sodium phosphomolybdate, hydrochloric acid and a reaction solvent, adding into a reaction kettle, preserving the temperature for a period of time at room temperature, then heating and adding hydrogen peroxide, continuing to react for a period of time at the temperature, and ending the reaction. And adding an inorganic salt aqueous solution into the reaction solution, washing with water to remove sodium phosphomolybdate in the reaction system, simultaneously reducing the solubility of the monosaccharide acid in water, and removing the solvent and the water from the reaction solution after washing with water to obtain a crude product of the monosaccharide acid.
2) Synthesis of modified tween-20: and adding the prepared crude monosaccharide acid into a reaction kettle, adding Tween-20 and a reaction solvent, adding a Lewis acid catalyst, heating for reaction, and finishing the reaction when no monosaccharide acid is detected in a reaction system. After the reaction is finished, separating and removing the solvent to obtain the modified tween-20 with the purity of more than 82 percent.
In the preparation process of the modified tween-20, in the step 1), the monosaccharide is one or more of glyceraldehyde, glucose, galactose and arabinose, and glucose is preferred;
the reaction solvent is one or more of toluene, chloroform and carbon tetrachloride, and chloroform is preferred;
the room temperature heat preservation time is 1-5 h, preferably 2-3 h;
the temperature of the temperature rise is 50-100 ℃, and the temperature is preferably 70-90 ℃; after the temperature is raised, adding hydrogen peroxide for reaction for 4-10 hours, preferably 6-8 hours;
the inorganic salt solution is one or more of saturated sodium chloride aqueous solution, saturated sodium sulfate aqueous solution and saturated ammonium chloride aqueous solution, and preferably saturated sodium chloride aqueous solution;
the molar ratio of the monosaccharide to the sodium phosphomolybdate is 1.05-0.15, preferably 1;
the molar ratio of the monosaccharide to the hydrochloric acid is 1;
the molar ratio of the monosaccharide to the reaction solvent is 1;
the molar ratio of the monosaccharide to the hydrogen peroxide is 1;
the mass and dosage ratio of the inorganic salt aqueous solution to the reaction solution is 1;
in the step 2), the reaction solvent is one or more of acetone, isopropanol and diethyl ether, preferably acetone; the Lewis acid catalyst is one or more of ferric chloride, ferrous chloride and copper bromide, and copper bromide is preferred;
the reaction temperature is 50-120 ℃, preferably 65-80 ℃;
the molar ratio of the monosugar acid to the Tween-20 is 1;
the molar ratio of the mono-sugar acid to the reaction solvent is 1;
the molar ratio of the mono-sugar acid to the Lewis acid catalyst is 1.
The second aspect of the invention relates to the application of the modified Tween-20 in preparing vitamin E emulsion.
The steps for preparing the vitamin E emulsion by using the modified Tween-20 are as follows:
1) Preparing an oil phase: respectively weighing a certain amount of vitamin E acetate and modified Tween-20, adding into a reaction kettle, and heating to a certain temperature for oil dissolution;
2) Preparing a water phase: weighing water-soluble wall materials, a water-based emulsifier and water, adding the water-soluble wall materials, the water-based emulsifier and the water into another reaction kettle, heating, mixing and stirring for a period of time to obtain a water phase;
3) And then adding the oil phase into the water phase at one time, and continuously mixing and stirring to obtain the stable vitamin E emulsion.
In the step 1), the mass ratio of the vitamin E acetate to the modified Tween-20 is (1);
the temperature of the dissolved oil is controlled to be 40-80 ℃, and preferably 50-70 ℃;
in the step 2), the water-soluble wall material during the preparation of the water phase is one or more of gelatin, arabic gum, modified starch and whey protein, and preferably modified starch;
the water-based emulsifier is one or more of polyglycerol-10 oleate, tween-20, tween 80 and sucrose ester, and preferably sucrose ester;
the heating temperature of the water phase is 40-80 ℃, preferably 50-65 ℃; the stirring time is 0.5-2 h, preferably 1-1.5 h;
the mass ratio of the water-soluble wall material to the vitamin E acetate is 1; the mass ratio of the vitamin E acetate to the aqueous emulsifier is 1:0.01 to 0.08, preferably 1: 0.04-0.06; the solid content of the emulsion is 20 to 70 percent, preferably 40 to 60 percent;
in the step 3), the oil phase is added into the water phase and then continuously mixed and stirred for 0.5 to 3 hours, preferably 1 to 2 hours;
the stirring speed is 200 to 1500rpm, preferably 500 to 800rpm.
The invention has the beneficial effects that:
1. the synthesis method of the modified tween 20 is provided, and the prepared modified tween 20 has excellent emulsifying property;
2. the modified tween-20 is used as an oily emulsifier, and is compounded and emulsified with other aqueous emulsifiers to obtain the emulsion with high oil loading rate, wide viscosity range and stable VE content.
Detailed Description
The technical solution of the present invention is further illustrated by the following specific examples, but is not limited thereto.
Example 1
Preparation of modified tween-20: 36g of glucose, 37.8g of sodium phosphomolybdate, 0.4g of dilute hydrochloric acid (36 wt%) and 720g of chloroform were weighed out and added to the reaction vessel, and the mixture was kept at room temperature for 2.5 hours, then heated to 75 ℃ and added with 31.7g of hydrogen peroxide (30 wt%), and the reaction was continued for 6 hours to complete the reaction. And adding 78g of saturated sodium chloride aqueous solution into the reaction solution for washing, standing the reaction solution after washing for phase separation, separating out an organic phase, and then carrying out reduced pressure distillation to remove the solvent to obtain a crude product of gluconic acid.
Weighing 19.6g of the prepared gluconic acid crude product, adding the gluconic acid crude product into a reaction kettle, then adding 157g of tween-20 and 580g of acetone, finally adding 0.49g of ferric chloride, heating to 65 ℃, and finishing the reaction when no monosaccharide acid is detected in a reaction system. Separating and removing the solvent to obtain the modified Tween-20 with the purity of 82.5%.
Preparing a vitamin E emulsion: weighing 50g of vitamin E acetate and 0.6g of the prepared modified Tween-20, heating the mixture in a reaction kettle to 60 ℃ for dissolution; weighing 100g of gelatin, 2g of tween-20 and 356g of water, adding into another reaction kettle, heating to 55 ℃, mixing and stirring for 1.5h to obtain a water phase; then the oil phase is poured into the water phase at one time and stirred for 2 hours, and the stirring speed is controlled to be 300rpm. The prepared emulsion is subjected to particle size distribution test, the particle size D90 of the emulsion is 0.3 mu m, the viscosity test result is 112cP, the VE test content is 9.70%, the content and the particle size of the emulsion are not changed after the emulsion is placed for 24 hours at room temperature, and the emulsion is good in stability.
Example 2
Preparation of modified tween-20: 18g of glyceraldehyde, 45.4g of sodium phosphomolybdate, 0.7g of dilute hydrochloric acid (36 wt%) and 1010g of toluene were weighed out and added to a reaction vessel, and the mixture was kept at room temperature for 2 hours, and then the reaction was heated to 95 ℃ and 36.3g of hydrogen peroxide (30 wt%) was added to continue the reaction for 8 hours, thereby completing the reaction. And adding 92.5g of saturated ammonium chloride aqueous solution into the reaction solution for washing, standing the reaction solution after washing for phase separation, separating an organic phase, and then removing the solvent by reduced pressure distillation to obtain a glyceric acid crude product.
Weighing 10.6g of the prepared glyceric acid crude product, adding the glyceric acid crude product into a reaction kettle, adding 261g of Tween-20, 631g of isopropanol, finally adding 0.89g of ferrous chloride, heating the reaction system to 80 ℃, and ending the reaction when glyceric acid is not detected in the reaction system. Separating and removing the solvent to obtain the modified tween-20 with the purity of 83.8 percent.
Preparing a vitamin E emulsion: weighing 50g of vitamin E acetate and 1.0g of the prepared modified Tween-20, and heating the mixture in a reaction kettle to 68 ℃ for dissolving; weighing 42g of modified starch, 2.3g of sucrose ester and 143g of water, adding the materials into another reaction kettle, heating to 60 ℃, and mixing and stirring for 1 hour to obtain a water phase; then the oil phase is poured into the water phase at one time and stirred for 2.5 hours, and the stirring speed is controlled to be 500rpm. The prepared emulsion is subjected to particle size distribution test, the particle size D90 of the emulsion is 0.4 mu m, the viscosity test result is 65cP, the VE test content is 20.1%, the content and the particle size of the emulsion are not changed after the emulsion is placed for 24 hours at room temperature, and the emulsion is good in stability.
Example 3
Preparation of modified tween-20: 36g of galactose, 34.1g of sodium phosphomolybdate, 0.32g of dilute hydrochloric acid (36 wt%) and 900g of chloroform were weighed out and added to a reaction vessel, and the mixture was kept at room temperature for 3 hours, then the reaction was heated to 60 ℃ and 27.2g of hydrogen peroxide (30 wt%) was added thereto, and the reaction was continued for 7 hours to complete the reaction. Adding 83g of saturated sodium chloride aqueous solution into the reaction solution for washing, standing the reaction solution after washing for phase separation, separating out an organic phase, and then removing the solvent by reduced pressure distillation to obtain a crude product of the galactonic acid.
Weighing 19.6g of the crude galactaric acid prepared above, adding the crude galactaric acid into a reaction kettle, then adding 313g of tween-20 and 1100g of diethyl ether, finally adding 1.0g of copper bromide, heating the reaction to 50 ℃, and finishing the reaction when no galactaric acid is detected in the reaction system. Separating and removing the solvent to obtain the modified tween-20 with the purity of 83.0 percent.
Preparing a vitamin E emulsion: weighing 50g of vitamin E acetate and 1.5g of the prepared modified Tween-20, heating the mixture in a reaction kettle to 60 ℃ for dissolution; weighing 83g of Arabic gum, 2.5g of polyglycerol-10 oleate and 320g of water, adding into another reaction kettle, heating to 70 ℃, and mixing and stirring for 1h to obtain a water phase; then the oil phase is poured into the water phase at one time and stirred for 2 hours, and the stirring speed is controlled to be 400rpm. The prepared emulsion is subjected to particle size distribution test, the particle size D90 of the emulsion is 0.3 mu m, the viscosity test result is 45cP, the VE test content is 10.8%, the content and the particle size of the emulsion are not changed after the emulsion is placed at room temperature for 24 hours, and the emulsion has good stability.
Comparative example
Preparing a vitamin E emulsion:
weighing 50g of vitamin E acetate, heating the vitamin E acetate to 68 ℃ in a reaction kettle, and dissolving the vitamin E acetate; weighing 42g of modified starch, 2.3g of sucrose ester and 143g of water, adding the materials into another reaction kettle, heating to 60 ℃, and mixing and stirring for 1 hour to obtain a water phase; then the oil phase is poured into the water phase at one time and stirred for 2.5h, and the stirring speed is controlled to be 500rpm. A large number of oil slick liquid drops appear on the surface of the prepared emulsion, and the particle size D90 of the emulsion reaches 20 mu m through a particle size test, so that a stable and uniform oil-in-water emulsion is not formed.
Claims (10)
1. A preparation method of modified Tween-20 comprises the following steps:
1) Weighing a certain amount of monosaccharide, sodium phosphomolybdate, hydrochloric acid and a reaction solvent, adding into a reaction kettle, heating, adding hydrogen peroxide, reacting for a period of time, and finishing the reaction; adding an inorganic salt aqueous solution into the reaction solution for washing, and removing the solvent and water to obtain a crude product of the monosaccharide acid;
2) And adding the crude monosaccharide acid, the Tween-20, the reaction solvent and the Lewis acid catalyst into a reaction kettle, heating to react, and separating and removing the solvent after the reaction is finished to obtain the modified Tween-20.
2. The method according to claim 1, wherein in step 1), the monosaccharide is one or more of glyceraldehyde, glucose, galactose and arabinose; and/or:
the molar ratio of the monosaccharide to the sodium phosphomolybdate is 1.05-0.15; and/or:
the molar ratio of the monosaccharide to the hydrochloric acid is 1.01-0.05; and/or:
the molar ratio of the monosaccharide to the hydrogen peroxide is 1 to 2.
3. The process according to any one of claims 1-2, wherein in step 1), the inorganic salt solution is one or more of a saturated aqueous sodium chloride solution, a saturated aqueous sodium sulfate solution, a saturated aqueous ammonium chloride solution;
preferably, the mass ratio of the inorganic salt aqueous solution to the reaction solution is 1.
4. The method according to any one of claims 1 to 3, wherein in step 2), the molar ratio of the monobonic acid to tween-20 is 1.
5. The method according to any one of claims 1 to 4, wherein in the step 2), the Lewis acid catalyst is one or more of ferric chloride, ferrous chloride and cupric bromide;
preferably, the molar ratio of the monosaccharide acid to the lewis acidic catalyst is 1.
6. A method of making a vitamin E emulsion comprising the steps of:
1) Preparing an oil phase: respectively weighing a certain amount of vitamin E acetate and the modified Tween-20 of any one of claims 1 to 5, adding into a reaction kettle, and heating to dissolve oil;
2) Preparation of an aqueous phase: weighing water-soluble wall materials, a water-based emulsifier and water, adding the water-soluble wall materials, the water-based emulsifier and the water into another reaction kettle, heating, mixing and stirring for a period of time to obtain a water phase;
3) Mixing the oil phase and the water phase, and continuously mixing and stirring to obtain the vitamin E emulsion.
7. The method according to claim 6, wherein in the step 1), the mass ratio of the vitamin E acetate to the modified Tween-20 is 1.
8. The method according to claim 6 or 7, wherein in step 2), the water-soluble wall material is one or more of gelatin, acacia, modified starch and whey protein;
preferably, the mass ratio of the water-soluble wall material to the vitamin E acetate is 1.
9. The method according to any one of claims 6 to 8, wherein in step 2), the aqueous emulsifier is one or more of polyglycerol-10 oleate, tween-20, tween 80, sucrose esters;
preferably, the mass ratio of the vitamin E acetate to the aqueous emulsifier is 1:0.01 to 0.08.
10. The method according to any one of claims 6 to 9, wherein the emulsion has a solid content of 20 to 70%.
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| US20040244127A1 (en) * | 2001-09-24 | 2004-12-09 | Jean-Marie Adam | Cationic reactive dyes |
| US20040063033A1 (en) * | 2002-09-24 | 2004-04-01 | Fuji Photo Film Co., Ltd. | Presensitized plate |
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