Preparation process of compound cooling agent

Abstract

The invention relates to a preparation technology of a compound cooling agent, and relates to the technical field of food additives, and the preparation technology comprises the following steps: mixing and dispersing a cooling agent, a cooling taste improving agent and an emulsifying agent into propylene glycol, and stirring to obtain a cooling agent premix; dispersing a wall material into water, heating and stirring to obtain a wall material solution; adding the cooling agent premix into the wall material solution, and stirring to obtain an emulsified dispersion liquid; and adding the cross-linking agent solution into the emulsified dispersion liquid, adjusting the pH value to be acidic, heating and stirring for reaction, cooling, adding ethanol for precipitation to obtain microcapsules, washing the microcapsules with ethanol, and freeze-drying to obtain the compound cooling agent. The compound cooling agent has the effect of improving the stability of the compound cooling agent, the compound cooling agent has a good cooling effect, and long-acting cooling feeling is provided through slow-release regulation and control.

Description

Technical Field

[0001] The present application relates to the technical field of food additives, and in particular to a preparation process of a compound cooling agent. Background Art

[0002] Cooling agents are widely used in many fields such as food, oral care products, tobacco, etc. They can give products a refreshing taste and unique flavor experience, and are deeply loved by consumers. However, the common single cooling agents on the market, such as menthol, have a certain cooling effect, but have obvious limitations in terms of the duration of the cooling effect, the intensity of the layered effect, and the comprehensive stimulation of different senses.

[0003] In view of the shortcomings of single cooling agents, compound cooling agents came into being. By rationally combining cooling agents with different characteristics, it is expected to achieve synergistic effects on the cooling sensation, make up for the defects of single cooling agents, and create more distinctive and attractive cooling products. However, in the preparation process of compound cooling agents, the compatibility between the cooling agents and between the cooling agents and other auxiliary ingredients is poor. Due to the differences in the chemical structure and physical properties of different cooling agents, stratification, precipitation, crystallization and other phenomena are prone to occur during mixing and compounding, which not only seriously affects the quality stability of the compound cooling agent, but also greatly reduces its cooling effect, so it needs to be improved. Summary of the invention

[0004] In order to enhance the cooling effect of cooling agents, the present application provides a preparation process of a compound cooling agent.

[0005] The preparation process of a compound cooling agent provided in the present application adopts the following technical scheme: A preparation process of a compound cooling agent comprises the following steps: (1) mixing and dispersing a cooling agent, a cooling enhancer and an emulsifier in propylene glycol, and stirring to obtain a cooling agent premix; (2) dispersing the wall material into water, heating and stirring to obtain a wall material solution; (3) adding the cooling agent premix to the wall material solution and stirring to obtain an emulsified dispersion; (4) adding the crosslinking agent solution to the emulsified dispersion, adjusting the pH to acidic, heating and stirring to react, cooling and adding ethanol to precipitate to obtain microcapsules, washing the microcapsules with ethanol, and freeze-drying to obtain the compound cooling agent.

[0006] The cooling agent and the cooling enhancer work synergistically. The cooling agent provides an instantaneous cooling sensation and a long-lasting refreshing feeling. The cooling enhancer can enhance the stimulation of the cooling agent on the human body's cooling receptors, making the cooling sensation stronger and lasting. The combination of the two enhances the cooling effect of the compound cooling agent. The emulsifier can promote the uniform dispersion of the cooling ingredients, which is beneficial to better contact between the core material and the wall material, so that the wall material and the core material fit better and improve the encapsulation efficiency. The wall material solution wraps the cooling agent premix to form a microcapsule structure, which effectively isolates the cooling ingredients from the external environment, reduces their degradation or volatilization caused by factors such as light, heat, and oxygen, and at the same time reduces the mutual influence of the components in the system, thereby improving the stability of the compound cooling agent.

[0007] Preferably, the cooling agent includes cooling agent ws-3, cooling agent ws-5 and cooling agent ws-23.

[0008] ws-3 has a low coolness threshold and a fast onset of action, which can bring a strong burst of coolness at the moment of contact, laying the foundation for instant coolness for the compound system; ws-5 has high cooling intensity and long duration, and its chemical structure can stimulate cool receptors for a long time to maintain coolness; ws-23 also has long-lasting cooling characteristics. After ws-3 provides instantaneous coolness, it synergizes with ws-5 to regulate the effect of coolness from immediate burst to long-lasting, effectively improving the quality and user experience of cool products.

[0009] Preferably, the mass ratio of the cooling agent WS-3, the cooling agent WS-5 and the cooling agent WS-23 is 1:1:(0.5-1.3).

[0010] The cooling agent compounded according to the above mass ratio has a good cooling effect and can provide a strong instantaneous cooling sensation and a long-lasting cooling experience.

[0011] Preferably, the cooling taste enhancing agent comprises menthol and menthone glycerol ketal.

[0012] Menthol has a strong cooling smell and feeling, which can quickly activate the body's cooling receptors, bringing an immediate and distinct cooling experience; menthone glycerol ketal can work synergistically with menthol to prolong the duration of the cooling effect, making the cooling sensation last longer in the mouth or on the skin, while enriching the layering of the cooling effect and avoiding the monotony of the cooling effect; menthol and menthone glycerol ketal also have antioxidant properties, can capture free radicals, and inhibit the occurrence of oxidation reactions, thereby reducing product deterioration and flavor deterioration caused by oxidation, and helping to maintain the stability of the compound cooling agent.

[0013] Preferably, the wall material comprises esterified modified konjac glucomannan and modified isomaltooligosaccharide.

[0014] The wall material formed by esterified modified konjac glucomannan and modified isomaltooligosaccharide has good film-forming and barrier properties, and can wrap the cooling agent and cooling enhancer therein, thereby achieving effective controlled release of cooling ingredients and releasing the cooling taste slowly and continuously; konjac glucomannan itself has antioxidant activity, and after esterification modification, its antioxidant capacity is further enhanced, which can reduce the oxidation of cooling ingredients caused by external environmental factors and improve the stability of the compound cooling agent.

[0015] Preferably, the raw materials for preparing the esterified modified konjac glucomannan include konjac glucomannan body, lauric acid and α-linolenic acid.

[0016] The introduction of lauric acid and α-linolenic acid makes konjac glucomannan have a certain lipophilicity, improves the compatibility of wall materials and cooling agent premixes, is conducive to the stable dispersion of cooling substances in the system, and thus achieves more precise and lasting cooling controlled release, thereby improving the cooling effect; α-linolenic acid is an unsaturated fatty acid, and the double bonds in its carbon chain can efficiently capture free radicals, block oxidation chain reactions, and synergize with konjac glucomannan to improve the antioxidant properties of the system; lauric acid and α-linolenic acid have antibacterial properties, and their fatty acid chains can destroy the cell membrane structure of microorganisms, interfere with the physiological metabolic process of microorganisms, and inhibit the growth and reproduction of microorganisms. After combining with konjac glucomannan, the antibacterial properties of the wall materials are improved, effectively preventing microbial contamination and erosion of cooling agent products, and improving the cooling effect and stability of the compound cooling agent.

[0017] Preferably, the esterified modified konjac glucomannan is prepared by the following steps: The main body of konjac glucomannan is added into water, and stirred until completely dissolved to obtain a konjac glucomannan solution; lauric acid and alpha-linolenic acid are dissolved in ethanol to obtain a fatty acid solution; an esterification catalyst is added into the konjac glucomannan solution, and stirred to obtain a reaction solution; the fatty acid solution is added into the reaction solution, and the temperature is raised, stirred, and refluxed for reaction, and after cooling, a solution after reaction is obtained; a sodium hydroxide aqueous solution is added into the solution after reaction, and the pH is adjusted to neutral to obtain a product solution, and the product solution is dialyzed with water and then freeze-dried to obtain an esterified modified konjac glucomannan.

[0018] The esterified modified konjac glucomannan prepared according to the above steps has good compatibility and can effectively improve the cooling effect, antioxidant performance and antibacterial performance of the compound cooling agent.

[0019] Preferably, the raw materials for preparing the modified isomaltooligosaccharide include isomaltooligosaccharide body and perilla extract.

[0020] Perilla extract modifies oligomaltose and introduces active ingredients into the wall material by grafting. Some active ingredients themselves have a cool feeling and can enrich the layered feeling of cool taste. Perilla extract is rich in a variety of antioxidant active substances, such as phenolic compounds, which can effectively remove free radicals in the system and inhibit the occurrence of oxidation reactions. They synergize with oligomaltose to enhance the antioxidant properties of the wall material and improve the stability of the cool agent. Perilla extract has antibacterial activity, and the natural antibacterial ingredients it contains can inhibit the growth and reproduction of a variety of microorganisms, improve the antibacterial properties of the wall material, effectively prevent microbial contamination and damage to the compound cool agent, and improve the stability of the compound cool agent.

[0021] Preferably, the modified isomaltooligosaccharide is prepared by the following steps: The isomaltooligosaccharide body is irradiated to obtain irradiated isomaltooligosaccharide; the irradiated isomaltooligosaccharide and perilla extract are dispersed in a phosphate buffer, stirred for reaction, an antioxidant is added to terminate the reaction, ultrafiltration is performed and then dialyzed, and the dialyzed product is freeze-dried to obtain modified isomaltooligosaccharide.

[0022] The isomaltooligosaccharide prepared according to the above steps has good antioxidant and antibacterial properties, can provide a cooling effect in the wall material, and enrich the layering of the compound cooling agent.

[0023] Preferably, the emulsifier comprises sucrose fatty acid ester.

[0024] Sucrose fatty acid ester has good emulsifying properties. The hydrophilic sucrose groups and hydrophobic fatty acid ester groups in its molecular structure enable it to effectively reduce interfacial tension, promote uniform dispersion of various components to form a stable cooling agent premix, construct a microscopic emulsified structure inside the core material, improve the interaction between the core material and the wall material, enable the wall material to fit better when wrapping the core material, enhance the structural stability of the microcapsule, and thus enhance the cooling effect of the compound cooling agent; ferulic acid has good biocompatibility, and its structure contains groups such as phenolic hydroxyl groups, which can efficiently capture free radicals, and has antibacterial activity, which can inhibit the growth of microorganisms and enhance the antioxidant and antibacterial properties of the compound cooling agent; ferulic acid enhances the stability of the wall material through covalent cross-linking, regulates the pore structure of the wall material, controls the release of cooling ingredients, and enhances the cooling effect of the compound cooling agent.

[0025] In summary, the present application includes at least one of the following beneficial technical effects: 1. The cooling agent and the cooling enhancer work synergistically. The cooling agent provides an instantaneous cooling sensation and a long-lasting cooling sensation. The cooling enhancer can enhance the stimulation of the cooling agent on the human body's cooling receptors, making the cooling sensation stronger and lasting. The combination of the two can enhance the cooling effect of the compound cooling agent. The emulsifier can promote the uniform dispersion of the cooling ingredients, which is conducive to better contact between the core material and the wall material, so that the wall material and the core material fit better and improve the encapsulation efficiency. The wall material solution wraps the cooling agent premix to form a microcapsule structure, which effectively isolates the cooling ingredients from the external environment, reduces their degradation or volatilization caused by factors such as light, heat, and oxygen, and reduces the mutual influence of the components in the system, thereby improving the stability of the compound cooling agent.

[0026] 2. The introduction of lauric acid and α-linolenic acid makes konjac glucomannan have a certain lipophilicity, improves the compatibility of the wall material and the cooling agent premix, is conducive to the stable dispersion of cooling substances in the system, and then achieves more accurate and lasting cooling controlled release, and improves the cooling effect; α-linolenic acid is an unsaturated fatty acid, and the double bonds in its carbon chain can efficiently capture free radicals, block oxidation chain reactions, and synergize with konjac glucomannan to improve the antioxidant properties of the system; lauric acid and α-linolenic acid have antibacterial properties, and their fatty acid chains can destroy the cell membrane structure of microorganisms, interfere with the physiological metabolic process of microorganisms, and inhibit the growth and reproduction of microorganisms. After combining with konjac glucomannan, the antibacterial properties of the wall material are improved, effectively preventing microbial contamination and erosion of cooling agent products, and improving the cooling effect and stability of the compound cooling agent.

[0027] 3. Perilla extract modifies oligosaccharides with isomaltooligosaccharides, and the active ingredients are grafted into the wall material. Some of the active ingredients themselves have a cool feeling, which can enrich the layered feeling of coolness. Perilla extract is rich in a variety of antioxidant active substances, such as phenolic compounds, which can effectively remove free radicals in the system, inhibit the occurrence of oxidation reactions, and synergize with isomaltooligosaccharides to enhance the antioxidant properties of the wall material and improve the stability of the coolant. Perilla extract has antibacterial activity, and the natural antibacterial ingredients it contains can inhibit the growth and reproduction of a variety of microorganisms, improve the antibacterial properties of the wall material, effectively prevent the contamination and destruction of the compound coolant by microorganisms, and improve the stability of the compound coolant. DETAILED DESCRIPTION

[0028] The present application discloses a preparation process of a compound cooling agent. The raw materials used in the present application can be obtained from commercially available raw materials unless otherwise specified. The present application is further described in detail below in conjunction with the examples: Ingredients: Konjac glucomannan (CAS No.: 37220-17-0), lauric acid (CAS No.: 143-07-7), α-linolenic acid (CAS No.: 463-40-1), esterification catalyst is p-toluenesulfonic acid (CAS No.: 104-15-4), isomaltooligosaccharide (CAS No.: 499-40-1), perilla leaf extract (CAS No.: 90082-61-4), antioxidant is vitamin C (CAS No.: 50-81-7), cooling agent ws-3 (CAS No.: 39711-79-0), cooling agent ws-5 (CAS No.: 68489-14-5), cooling agent ws-23 (CAS No.: 51115-67-4), menthol (CAS No.: 89-78-1), menthone glycerol ketal (CAS No.: 63187-91-7), emulsifier is sucrose fatty acid ester (CAS No.: 37318-31-3), cross-linking agent is ferulic acid (CAS No.: 1135-24-6).

[0029] Example 1 Preparation of esterified modified konjac glucomannan Dissolve konjac glucomannan in deionized water, stir at a speed of 200 rpm until completely dissolved, so that the mass concentration of the solution is 10%, and obtain a konjac glucomannan solution; dissolve lauric acid and α-linolenic acid in anhydrous ethanol to make the mass concentration 30%, and obtain a fatty acid solution; add an esterification catalyst to the konjac glucomannan solution, stir at a speed of 200 rpm for 15 minutes, and obtain a reaction solution; add the fatty acid solution to the reaction solution, so that the mass ratio of konjac glucomannan, lauric acid and α-linolenic acid is 1:0.2:0.5, the amount of the esterification catalyst accounts for 5% of the total mass of the system, and the addition is completed within 1 hour, heat to 80°C, stir and reflux at a speed of 400 rpm for 6 hours, and after cooling to below 30°C, obtain a solution after reaction; add 1 mol / L sodium hydroxide aqueous solution to the solution after reaction, adjust the pH to 7, obtain a product solution, dialyze the product solution with deionized water, and freeze-dry at -20°C to obtain an esterified modified konjac glucomannan.

[0030] Preparation of modified isomaltooligosaccharide The oligosaccharide is irradiated by a gamma-ray irradiation source with an irradiation dose of 20 kGy to obtain irradiated oligosaccharide; the irradiated oligosaccharide and perilla extract are dispersed in a phosphate buffer solution with a mass ratio of oligosaccharide to perilla extract of 1:0.1, and the reaction is stirred at a speed of 200 rpm for 12 hours, and an antioxidant accounting for 0.1% of the mass of the oligosaccharide is added to terminate the reaction, and the product is dialyzed after ultrafiltration, and the dialyzed product is freeze-dried at -20°C to obtain modified oligosaccharide.

[0031] Preparation of compound cooling agent (1) 40 g of cooling agent, 10 g of cooling enhancer and 5 g of emulsifier were mixed and dispersed in 150 mL of propylene glycol, and stirred at a speed of 300 rpm to obtain a cooling agent premix, wherein the mass ratio of cooling agent WS-3, cooling agent WS-5 and cooling agent WS-23 in the cooling agent was 1:1:0.5, and the mass ratio of menthol and menthone glycerol acetal in the cooling enhancer was 2:1; (2) dissolving 20 g of modified konjac glucomannan and 10 g of modified isomaltooligosaccharide in 100 mL of deionized water, stirring at 400 rpm for 30 min at 60° C. to obtain a wall material solution; (3) adding the cooling agent premix to the wall material solution and stirring at 500 rpm for 30 min to obtain an emulsified dispersion; (4) Dissolve 1 g of the cross-linking agent in 10 mL of deionized water to obtain a cross-linking agent solution, add the cross-linking agent solution to the emulsified dispersion within 15 minutes, adjust the pH to 5 with hydrochloric acid, stir the reaction at 40°C at a speed of 300 rpm for 4 hours, cool to 10°C, add anhydrous ethanol for alcohol precipitation to obtain microcapsules, wash the microcapsules with anhydrous ethanol, and freeze-dry at -20°C to obtain a compound cooling agent.

[0032] Example 2 Preparation of esterified modified konjac glucomannan Dissolve konjac glucomannan in deionized water, stir at a speed of 200 rpm until completely dissolved, so that the mass concentration of the solution is 10%, and obtain a konjac glucomannan solution; dissolve lauric acid and α-linolenic acid in anhydrous ethanol to make the mass concentration 30%, and obtain a fatty acid solution; add an esterification catalyst to the konjac glucomannan solution, stir at a speed of 200 rpm for 15 minutes, and obtain a reaction solution; add the fatty acid solution to the reaction solution, so that the mass ratio of konjac glucomannan, lauric acid and α-linolenic acid is 1:0.4:0.3, the amount of the esterification catalyst accounts for 5% of the total mass of the system, and the addition is completed within 1 hour, heat to 80°C, stir and reflux at a speed of 400 rpm for 6 hours, and after cooling to below 30°C, obtain a reacted solution; add 1 mol / L sodium hydroxide aqueous solution to the reacted solution, adjust the pH to 7, and obtain a product solution. After the product solution is dialyzed with deionized water, it is freeze-dried at -20°C to obtain an esterified modified konjac glucomannan.

[0033] Preparation of modified isomaltooligosaccharide The oligosaccharide is irradiated by a gamma-ray irradiation source with an irradiation dose of 20 kGy to obtain irradiated oligosaccharide; the irradiated oligosaccharide and perilla extract are dispersed in a phosphate buffer solution with a mass ratio of oligosaccharide to perilla extract of 1:0.2, and the reaction is stirred at a speed of 200 rpm for 12 hours, and an antioxidant accounting for 0.1% of the mass of the oligosaccharide is added to terminate the reaction, and the product is dialyzed after ultrafiltration, and the dialyzed product is freeze-dried at -20°C to obtain modified oligosaccharide.

[0034] Preparation of compound cooling agent (1) 70 g of cooling agent, 30 g of cooling enhancer and 10 g of emulsifier were mixed and dispersed in 200 mL of propylene glycol, and stirred at a speed of 300 rpm to obtain a cooling agent premix, wherein the mass ratio of cooling agent WS-3, cooling agent WS-5 and cooling agent WS-23 in the cooling agent was 1:1:1.3, and the mass ratio of menthol and menthone glycerol acetal in the cooling enhancer was 2:1; (2) dissolving 30 g of modified konjac glucomannan and 20 g of modified isomaltooligosaccharide in 100 mL of deionized water, stirring at 400 rpm for 30 min at 60° C. to obtain a wall material solution; (3) adding the cooling agent premix to the wall material solution and stirring at 500 rpm for 30 min to obtain an emulsified dispersion; (4) Dissolve 2 g of a cross-linking agent in 10 mL of deionized water to obtain a cross-linking agent solution, add the cross-linking agent solution to the emulsified dispersion within 15 min, adjust the pH to 5 with hydrochloric acid, stir the reaction at 40° C. and 300 rpm for 4 h, cool to 10° C., add anhydrous ethanol for alcohol precipitation to obtain microcapsules, wash the microcapsules with anhydrous ethanol, and freeze-dry at -20° C. to obtain a compound cooling agent.

[0035] Example 3 Preparation of esterified modified konjac glucomannan Dissolve konjac glucomannan in deionized water, stir at a speed of 200 rpm until completely dissolved, so that the mass concentration of the solution is 10%, and obtain a konjac glucomannan solution; dissolve lauric acid and α-linolenic acid in anhydrous ethanol to make the mass concentration 30%, and obtain a fatty acid solution; add an esterification catalyst to the konjac glucomannan solution, stir at a speed of 200 rpm for 15 minutes, and obtain a reaction solution; add the fatty acid solution to the reaction solution, so that the mass ratio of konjac glucomannan, lauric acid and α-linolenic acid is 1:0.3:0.4, the amount of the esterification catalyst accounts for 5% of the total mass of the system, and the addition is completed within 1 hour, heat to 80°C, stir and reflux at a speed of 400 rpm for reaction for 6 hours, and after cooling to below 30°C, obtain a solution after reaction; add 1 mol / L sodium hydroxide aqueous solution to the solution after reaction, adjust the pH to 7, obtain a product solution, dialyze the product solution with deionized water, and freeze-dry at -20°C to obtain an esterified modified konjac glucomannan.

[0036] Preparation of modified isomaltooligosaccharide The isomaltooligosaccharide is irradiated by a gamma-ray irradiation source with an irradiation dose of 20 kGy to obtain irradiated isomaltooligosaccharide; the irradiated isomaltooligosaccharide and perilla extract are dispersed in a phosphate buffer solution with a mass ratio of isomaltooligosaccharide to perilla extract of 1:0.15, and the reaction is stirred at a speed of 200 rpm for 12 hours, and an antioxidant accounting for 0.1% of the mass of the isomaltooligosaccharide is added to terminate the reaction, and the product is dialyzed after ultrafiltration, and the dialyzed product is freeze-dried at -20°C to obtain modified isomaltooligosaccharide.

[0037] Preparation of compound cooling agent (1) 55 g of cooling agent, 20 g of cooling enhancer and 7.5 g of emulsifier were mixed and dispersed in 175 mL of propylene glycol, and stirred at a speed of 300 rpm to obtain a cooling agent premix, wherein the mass ratio of cooling agent WS-3, cooling agent WS-5 and cooling agent WS-23 in the cooling agent was 1:1:0.9, and the mass ratio of menthol and menthone glycerol acetal in the cooling enhancer was 2:1; (2) dissolving 25 g of modified konjac glucomannan and 15 g of modified isomaltooligosaccharide in 100 mL of deionized water, stirring at 400 rpm for 30 min at 60° C. to obtain a wall material solution; (3) adding the cooling agent premix to the wall material solution and stirring at 500 rpm for 30 min to obtain an emulsified dispersion; (4) Dissolve 1.5 g of a cross-linking agent in 10 mL of deionized water to obtain a cross-linking agent solution, add the cross-linking agent solution to the emulsified dispersion within 15 minutes, adjust the pH to 5 with hydrochloric acid, stir the reaction at 40° C. and 300 rpm for 4 hours, cool to 10° C., add anhydrous ethanol for alcohol precipitation to obtain microcapsules, wash the microcapsules with anhydrous ethanol, and freeze-dry at -20° C. to obtain a compound cooling agent.

[0038] Example 4 Example 4 is based on Example 3. The only difference between Example 4 and Example 3 is that the mass ratio of the cooling agent WS-3, the cooling agent WS-5 and the cooling agent WS-23 in the compound cooling agent in Example 4 is 1:1:0.1.

[0039] Example 5 Example 5 is based on Example 3. The only difference between Example 5 and Example 3 is that the mass ratio of the cooling agent WS-3, the cooling agent WS-5 and the cooling agent WS-23 in the compound cooling agent in Example 5 is 1:1:1.7.

[0040] Example 6 Example 6 is based on Example 3. The only difference between Example 6 and Example 3 is that the cooling agent WS-23 is not added in Example 6.

[0041] Example 7 Example 7 is based on Example 3. The only difference between Example 7 and Example 3 is that in Example 7, menthone glycerol acetal is not added to the cool taste enhancing agent.

[0042] Example 8 Example 8 is based on Example 3. The only difference between Example 8 and Example 3 is that the mass ratio of konjac glucomannan bulk, lauric acid and α-linolenic acid in the esterified modified konjac glucomannan in Example 8 is 1:0.1:0.2.

[0043] Example 9 Example 9 is based on Example 3. The only difference between Example 9 and Example 3 is that the mass ratio of konjac glucomannan bulk, lauric acid and α-linolenic acid in the esterified modified konjac glucomannan in Example 9 is 1:0.5:0.6.

[0044] Example 10 Example 10 is based on Example 3. The only difference between Example 10 and Example 3 is that in Example 10, the esterified modified konjac glucomannan is replaced by konjac glucomannan.

[0045] Embodiment 11 Example 11 is based on Example 3. The only difference between Example 11 and Example 3 is that the mass ratio of isomaltooligosaccharide body and perilla extract in the modified isomaltooligosaccharide in Example 11 is 1:0.05.

[0046] Example 12 Example 12 is based on Example 3. The only difference between Example 12 and Example 3 is that the mass ratio of isomaltooligosaccharide body and perilla extract in the modified isomaltooligosaccharide in Example 12 is 1:0.3.

[0047] Example 13 Example 13 is based on Example 3, and the only difference between Example 13 and Example 3 is that in Example 13, the emulsifier is replaced by calcium stearoyl lactylate.

[0048] Comparative Example 1 Comparative Example 1 is based on Example 3, and the only difference between Comparative Example 1 and Example 3 is that in Comparative Example 1, an emulsifier is added to the wall material solution.

[0049] Performance testing (1) Cooling agent duration test: 10 healthy people with normal sense of smell and taste and who have not suffered from cold, rhinitis or other diseases recently were selected as test subjects. 5 g of the sample was dispersed in 100 mL of deionized water to obtain a sample dispersion. A blank control solution without adding the sample was set up. The filter paper disc was soaked in the sample dispersion for 5 min and then taken out. The test subjects put the soaked filter paper disc into their mouths and recorded the time when the cooling intensity of the sample was close to that of the blank control. After measurement, the highest and lowest values ​​were removed and the remaining values ​​were averaged. The results are recorded in Table 1.

[0050] (2) Cooling agent stability test: The samples were placed in an ozone atmosphere at a flow rate of 200 mL / min for 24 h. The initial concentration and post-treatment concentration of the cooling agent components were tested and the concentration change rate was calculated. Each sample was tested three times and the average value was taken after measurement. The results are recorded in Table 1.

[0051] (3) Antibacterial performance test of cooling agents: The sample was prepared into a dispersion with a concentration of 1 mg / mL using distilled water and placed in a sterilized culture dish. The bacterial solution containing Escherichia coli was added dropwise to the sample and mixed evenly. The sample was cultured at a constant temperature for 24 h under the same conditions. The sterilization rate of each sample was then measured. Each sample was tested three times and the average value was calculated after the test. The results are recorded in Table 1.

[0052] Table 1 Test results of cooling effect, antioxidant and antibacterial properties of compound cooling agents Test results Duration (min) After oxidation (%) Antibacterial rate (%) Example 1 53 15.9 83.6 Example 2 55 15.3 84.2 Example 3 56 15.6 84.1 Example 4 50 15.7 83.8 Example 5 48 15.8 83.6 Example 6 47 16.2 83.3 Example 7 45 18.9 82.4 Example 8 43 21.7 81.6 Example 9 46 14.3 86.5 Example 10 40 25.8 77.3 Embodiment 11 46 17.5 82.6 Example 12 48 15.6 85.8 Example 13 46 16.7 83.1 Comparative Example 1 43 18.9 82.8 It can be seen from Table 1 that the cooling effect of Examples 1-3 lasts for more than 53 minutes, the concentration change rate after oxidation is less than 15.9%, and the antibacterial rate is greater than 83.6%. It can be seen that the compound cooling agent prepared in the present application has good cooling effect, stability and antibacterial effect.

[0053] As can be seen from Table 1, the only difference between Examples 4 and 5 and Example 3 is that the mass ratio of the cooling agent WS-3, the cooling agent WS-5 and the cooling agent WS-23 in the compound cooling agent in Example 4 is 1:1:0.1, and the mass ratio of the cooling agent WS-3, the cooling agent WS-5 and the cooling agent WS-23 in the compound cooling agent in Example 5 is 1:1:1.7. Compared with Example 3, the cooling effect of Examples 4 and 5 is reduced; this is because the component ratio between the cooling agents is changed. After the ratio is destroyed, the synergistic effect between the cooling agents is affected, and the cooling effect is reduced.

[0054] As can be seen from Table 1, the only difference between Examples 6 and 7 and Example 3 is that: in Example 6, no cooling agent WS-23 is added, and in Example 7, no menthone glycerol ketal is added to the cooling enhancer. Compared with Example 3, Examples 6 and 7 have reduced cooling effects, antioxidant properties and antibacterial properties. This is because reducing the components in the cooling agent or the cooling enhancer will affect the synergistic effect, the stimulation of the cooling receptors is reduced, and the cooling effect is reduced. In addition, menthone glycerol ketal has certain antioxidant properties, and the antioxidant effect is reduced.

[0055] As can be seen from Table 1, the difference between Examples 8, 9, and 10 and Example 3 is that the mass ratio of konjac glucomannan body, lauric acid, and α-linolenic acid in the esterified modified konjac glucomannan in Example 8 is 1:0.1:0.2, the mass ratio of konjac glucomannan body, lauric acid, and α-linolenic acid in the esterified modified konjac glucomannan in Example 9 is 1:0.5:0.6, and the esterified modified konjac glucomannan is replaced with konjac glucomannan in Example 10. Compared with Example 3, the cooling effect, antioxidant performance, and antibacterial performance of Examples 8, 9, and 10 are reduced; this is because the ratio of the components in the esterified modified konjac glucomannan is destroyed, and too much or too little fatty acid will affect the modification effect and the compatibility between the wall material and the core material, thereby reducing the sustained release performance and protective effect of the microcapsule, and the cooling effect, antioxidant performance, and antibacterial performance of the compound cooling agent are affected; if fatty acids are not used for modification, the performance will be further reduced.

[0056] As can be seen from Table 1, the only difference between Examples 11 and 12 and Example 3 is that the mass ratio of oligomeric isomaltoligosaccharides to perilla extract in the modified oligomeric isomaltoligosaccharides in Example 11 is 1:0.05, and the mass ratio of oligomeric isomaltoligosaccharides to perilla extract in the modified oligomeric isomaltoligosaccharides in Example 12 is 1:0.3. Compared with Example 3, the cooling effect, antioxidant properties and antibacterial properties of Examples 11 and 12 are reduced; this is because the addition amount of perilla extract is changed, and too much or too little perilla extract will affect the stability and compatibility of the modified oligomeric isomaltoligosaccharides, and affect the embedding effect of the microcapsules, thereby affecting the cooling effect, antioxidant properties and antibacterial properties.

[0057] As can be seen from Table 1, the only difference between Example 13 and Example 3 is that the emulsifier in Example 13 is replaced by calcium stearoyl lactylate. Compared with Example 3, the cooling effect, antioxidant performance and antibacterial performance of Example 13 are reduced; this is because the emulsifier is replaced by calcium stearoyl lactylate, the promoting effect of calcium stearoyl lactylate on the dispersibility and compatibility of the system is reduced, the stability of the compound cooling agent is reduced, and thus the cooling effect, antioxidant performance and antibacterial performance are affected.

[0058] It can be seen from Table 1 that the only difference between Comparative Example 1 and Example 3 is that in Comparative Example 1, an emulsifier is added to the wall material solution. Compared with Example 3, the cooling effect, antioxidant performance and antibacterial performance of Comparative Example 1 are reduced. This is because the emulsifier is not directly added to the core material solution, which will affect the dispersion effect of the cooling components in the core material and reduce the bonding force between the core material and the wall material, thereby reducing the antioxidant performance and antibacterial performance, and the sustained release effect and protective effect are affected to a certain extent, and the cooling effect is reduced.

[0059] This specific embodiment is only an explanation of the present application, and it is not a limitation of the present application. Through the above description, relevant staff can make various changes and modifications without deviating from the technical idea of ​​the present application. The technical scope of the present application is not limited to the content in the specification, and its technical scope must be determined according to the scope of the claims.

Claims

1. A preparation process of a compound cooling agent, characterized in that: The following steps are involved: (1) mixing and dispersing a cooling agent, a cooling enhancer and an emulsifier in propylene glycol, and stirring to obtain a cooling agent premix; (2) dispersing the wall material into water, heating and stirring to obtain a wall material solution; (3) adding the cooling agent premix to the wall material solution and stirring to obtain an emulsified dispersion; (4) Add the crosslinking agent solution to the emulsified dispersion, adjust the pH to acidic, heat and stir to react, cool down and add ethanol to precipitate to obtain microcapsules, wash the microcapsules with ethanol, and freeze-dry to obtain the compound cooling agent.

2. The preparation process of a compound cooling agent according to claim 1, characterized in that: The cooling agents include cooling agent ws-3, cooling agent ws-5 and cooling agent ws-23.

3. The preparation process of a compound cooling agent according to claim 2, characterized in that: The mass ratio of the cooling agent WS-3, the cooling agent WS-5 and the cooling agent WS-23 is 1:1:(0.5-1.3).

4. The preparation process of a compound cooling agent according to claim 1, characterized in that: The cooling taste enhancing agent includes menthol and menthone glycerol ketal.

5. The preparation process of a compound cooling agent according to claim 1, characterized in that: The wall material comprises esterified modified konjac glucomannan and modified isomaltooligosaccharide.

6. The preparation process of a compound cooling agent according to claim 5, characterized in that: The raw materials for preparing the esterified modified konjac glucomannan include konjac glucomannan body, lauric acid and alpha-linolenic acid.

7. The preparation process of a compound cooling agent according to claim 6, characterized in that: The esterified modified konjac glucomannan is prepared by the following steps: The konjac glucomannan body is added into water and stirred until completely dissolved to obtain a konjac glucomannan solution; lauric acid and α-linolenic acid are dissolved in ethanol to obtain a fatty acid solution; an esterification catalyst is added into the konjac glucomannan solution and stirred to obtain a reaction solution; the fatty acid solution is added into the reaction solution, heated and stirred to reflux for reaction, and after cooling, a reacted solution is obtained; A sodium hydroxide aqueous solution is added to the solution after the reaction, and the pH is adjusted to neutral to obtain a product solution. The product solution is dialyzed with water and then freeze-dried to obtain esterified modified konjac glucomannan.

8. The preparation process of a compound cooling agent according to claim 5, characterized in that: The raw materials for preparing the modified isomaltooligosaccharide include isomaltooligosaccharide body and perilla extract.

9. The preparation process of a compound cooling agent according to claim 8, characterized in that: The modified isomaltooligosaccharide is prepared by the following steps: The isomaltooligosaccharide body is irradiated to obtain irradiated isomaltooligosaccharide; the irradiated isomaltooligosaccharide and perilla extract are dispersed in a phosphate buffer, stirred for reaction, an antioxidant is added to terminate the reaction, ultrafiltration is performed and then dialyzed, and the dialyzed product is freeze-dried to obtain modified isomaltooligosaccharide.

10. The preparation process of a compound cooling agent according to claim 1, characterized in that: The emulsifier includes sucrose fatty acid ester, and the cross-linking agent is ferulic acid.