CN111632564A - Polyurethane peppermint oil microcapsule and preparation method thereof - Google Patents
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
- B01J13/02—Making microcapsules or microballoons
- B01J13/06—Making microcapsules or microballoons by phase separation
- B01J13/14—Polymerisation; cross-linking
- B01J13/16—Interfacial polymerisation
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3206—Polyhydroxy compounds aliphatic
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/64—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63
- C08G18/6484—Polysaccharides and derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/6505—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen the low-molecular compounds being compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6511—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen the low-molecular compounds being compounds of group C08G18/32 or polyamines of C08G18/38 compounds of group C08G18/3203
- C08G18/6517—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen the low-molecular compounds being compounds of group C08G18/32 or polyamines of C08G18/38 compounds of group C08G18/3203 having at least three hydroxy groups
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Abstract
The invention discloses a polyurethane peppermint oil microcapsule and a preparation method thereof. The raw materials include polyisocyanates, peppermint oil, arabic gum, polysaccharide, etc. The preparation method comprises the following steps: mixing polybasic isocyanate and peppermint oil to obtain oil phase; uniformly mixing Arabic gum with deionized water to obtain a water phase; slowly adding water phase into the oil phase, and emulsifying with ultrasonic cell pulverizer to obtain oil-in-water stable emulsion containing peppermint oil; adding a polysaccharide solution into the emulsion under the condition of heating and stirring, and reacting to obtain a suspension; and (3) sequentially centrifuging, decanting, filtering, washing and drying the suspension to collect the polyurethane peppermint oil microcapsules. The polyurethane peppermint oil microcapsule prepared by the method has compact shell layer, environment-friendly raw materials, no organic solvent and easy processing, is expected to solve the problem of poor biocompatibility of common polyurethane microcapsules, and expands the application range of the peppermint oil in various fields.
Description
Technical Field
The invention relates to a polyurethane peppermint oil microcapsule and a preparation method thereof, belonging to the field of fine chemical engineering.
Background
The mint is a plant of the genus Mentha of the family Labiatae, is pungent in taste and cool in nature, has the effects of dispelling wind and heat, refreshing the head and eyes, relieving sore throat, resisting bacteria and inflammation, enhancing immunity and the like, and is widely used in Chinese herbal medicine formulas. Peppermint oil is a yellowish green or yellow oily liquid extracted from peppermint (Mentha x piperita L.) and has a special peppermint aroma. The peppermint oil has high medicinal value, and may be used widely in cosmetics, perfume, toothpaste, oral hygiene article, cigarette, soap, etc. However, the main components of peppermint oil are highly volatile and unstable in light, oxygen, high temperature and humidity, which is liable to cause quality loss and product deterioration. Microencapsulation is an effective method of protecting peppermint oil from rapid evaporation and deterioration, and also releasing the volatile material from the enclosed microcapsules as needed. The patent with publication number CN109628219A reports a preparation method of a mint-flavor type aroma-containing microcapsule used in a non-burning tobacco by heating, gelatin and polysaccharide are used as wall materials to encapsulate mint-flavor essence, and the mint-flavor essence is added into a cigarette filter stick which is not burned by heating, so that the aim of controllably releasing the aroma is fulfilled.
Polyurethane (PU) is one of the fastest growing polymer synthetic materials in the world, and has been widely applied to numerous fields of national economy. PU as the microcapsule wall material shows excellent performances such as good wear resistance, high mechanical strength and the like. The patent with publication number CN101161921A reports a preparation method of polyurethane anti-mosquito fragrant microcapsules, and microcapsules prepared by using PU material as the capsule wall material have certain resilience and are easy to process. Patent publication No. CN104420230A reports a method for finishing fabric by utilizing polyurethane type aromatic microcapsule finishing agent, and PU capsule wall material has high strength of plastic and high elasticity of rubber, and is oil-resistant and wear-resistant, and the defect of oil spots is effectively avoided.
The preparation method of the PU microcapsule is mainly an interfacial polymerization method, and is widely applied due to the advantages of good capsule wall film-forming property, high core material coating rate, high reaction speed, simple operation, easy process control and the like (CN100396842C, CN103962076B and CN 106566477A). The prior art discloses the preparation of polyurethane shells by reacting suitable isocyanates as starting materials with polyols/polyamines. Patent publication CN105722495A reports a preparation method of polyurea/polyurethane microcapsules, which comprises dissolving at least one polyisocyanate in perfume to form a solution, then adding an emulsifier or stabilizer to the solution, and finally chain-extending with polyol or polyamine compounds to form a wall material.
Organic solvents are generally used in the preparation process of the polyurethane microcapsules, which limits the application range of the microcapsules to a certain extent. Patent publication No. CN101392460A reports a preparation method of polyurethane skin-care microcapsules, under the premise of not using any organic solvent, oil-soluble skin-care substances and isocyanate are uniformly mixed according to a proportion, then an emulsifier aqueous solution is added to obtain a dispersion system, and finally the polyurethane microcapsules are prepared under the action of a polyglycol chain extender. The patent with the publication number of CN106753253A discloses a preparation method of an environment-friendly polyurea/polyurethane wall microcapsule, which is prepared by polymerization of polyisocyanate and polyamine/polyalcohol interface, does not contain harmful substances such as formaldehyde and the like, and is healthy and environment-friendly.
The application of the traditional polyurethane microcapsule is mainly limited by monomer toxicity, easy pollution in the preparation process and the like, and the safety and the environmental protection are not fully paid attention. Therefore, there is still a need to further improve the safety and environmental protection of the raw materials and preparation processes of the microcapsules, especially to research polyurethane microcapsules which can be widely applied.
Disclosure of Invention
The technical problem to be solved by the invention is as follows: the loss of the existing peppermint oil caused by volatilization and instability during use is a technical problem.
In order to solve the technical problems, the invention provides a polyurethane peppermint oil microcapsule which is characterized by comprising the following components in percentage by mass:
preferably, the polyisocyanate is a prepolymer of toluene diisocyanate.
Preferably, the polysaccharide is xylitol.
The invention also provides a preparation method of the polyurethane peppermint oil microcapsule, which is characterized by comprising the following steps:
step 1): mixing polybasic isocyanate and peppermint oil to obtain oil phase;
step 2): uniformly mixing Arabic gum with deionized water to obtain a water phase;
step 3): slowly adding water phase into the oil phase, and emulsifying with ultrasonic cell pulverizer to obtain oil-in-water stable emulsion containing peppermint oil;
step 4): adding a polysaccharide solution into the emulsion obtained in the step 3) under the condition of heating and stirring, and reacting to obtain a suspension containing the polyurethane peppermint oil microcapsule;
step 5): and (3) sequentially centrifuging, decanting, filtering, washing and drying the suspension to collect the polyurethane peppermint oil microcapsules.
Preferably, the mixing in step 1) is specifically: mixing for 2-4 min under magnetic stirring at 300-600 r/min; and (4) carrying out ultrasonic treatment for 1-3 min.
Preferably, the step 2) is specifically: adding the Arabic gum solution into the oil phase at the speed of 30-80 mL/h, mixing for 10-15 min under the magnetic stirring of 300-600 r/min, and then carrying out ultrasonic cell crushing treatment for 10-15 min.
Preferably, the step 4) is specifically: adding the polysaccharide solution into the emulsion at 40-50 ℃ under magnetic stirring at 300-600 r/min, and then reacting for 1.0-2.5 h at 60-70 ℃.
Preferably, the rotating speed of centrifugation in the step 5) is 7000-11000 r/min; the washing times are 2-4 times; the drying adopts vacuum freeze drying for 24 h.
Preferably, the average particle size of the polyurethane peppermint oil microcapsule obtained in the step 5) is 1.68-8.11 microns, the loading rate is 22-29%, the polyurethane peppermint oil microcapsule is regular spherical, the surface is smooth, and the particle size distribution is uniform.
The invention adopts Arabic gum to emulsify the mixed oil phase of peppermint oil and isocyanate monomer, then adds polysaccharide monomer, and forms a polyurethane shell layer through interfacial polymerization reaction under the conditions of heating and stirring.
Compared with the prior art, the invention has the beneficial technical effects that:
(1) the polyurethane peppermint oil microcapsule prepared by the invention does not use any organic solvent, and adopts polysaccharide monomers with good biocompatibility, safety and environmental protection to prepare polyurethane as a microcapsule shell layer. Therefore, the finally obtained polyurethane peppermint oil microcapsule has low toxicity, environmental protection and good biocompatibility, and can be widely applied to the fields of textile, daily chemicals, paint and the like.
(2) The invention adopts an interface polymerization method to form a polyurethane shell layer on an oil-water interface, has better compactness and smoothness, and has uniform particle size.
(3) The invention can improve the environmental tolerance of the peppermint oil and continuously release the fragrance, thereby expanding the application range of the peppermint oil.
Drawings
FIG. 1 is an optical microscope photograph of the polyurethane peppermint oil microcapsules obtained in example 1;
fig. 2 is an optical microscope photograph of the polyurethane peppermint oil microcapsule obtained in example 5.
Detailed Description
In order to make the invention more comprehensible, preferred embodiments are described in detail below with reference to the accompanying drawings.
The average particle size of the polyurethane peppermint oil microcapsules obtained in examples 1 to 5 was measured using a particle size analyzer (MASTERSIZER-3000, malvern).
The loading ratios of the polyurethane peppermint oil microcapsules obtained in examples 1 to 5 were measured by thermogravimetric analysis (TGA-Q5000, TA instruments, USA) according to the method of thermogravimetric analysis (Hu et al, Journal of Applied Polymer science 2014(131):631- > 644).
Example 1
The polyurethane peppermint oil microcapsule comprises the following raw materials:
the preparation method of the polyurethane peppermint oil microcapsule comprises the following specific steps:
(a) weighing arabic gum and dissolving the arabic gum in deionized water to prepare a arabic gum solution; weighing the isocyanate prepolymer and peppermint oil, mixing for 2min under magnetic stirring of 400r/min, and performing ultrasonic treatment for 1min to obtain an isocyanate prepolymer-peppermint oil mixed oil phase;
(b) b, adding the Arabic gum solution prepared in the step a into the oil phase prepared in the step a at the speed of 30mL/h, and mixing for 10min under the condition of magnetic stirring at 300 r/min; then ultrasonic cell crushing treatment is carried out for 10min to obtain O/W emulsion of isocyanate prepolymer-peppermint oil-Arabic gum;
(c) weighing polysaccharide, and dissolving the polysaccharide in deionized water to obtain a polysaccharide solution;
(d) c, under the condition of magnetic stirring at 800r/min, adding the polysaccharide solution prepared in the step c into the O/W emulsion obtained in the step b at the temperature of 50 ℃; heating to 70 ℃ and reacting for 2h to obtain polyurethane peppermint oil microcapsule suspension;
(e) cooling the polyurethane peppermint oil microcapsule suspension obtained in the step d to room temperature, and centrifuging at 11000 r/min; decanting, filtering, washing with water for 3 times, and vacuum freeze drying the suspension for 24 hr to obtain polyurethane peppermint oil microcapsule.
The average particle size of the prepared polyurethane peppermint oil microcapsule is 5.71 mu m, and the load rate is 22.38%.
The appearance of the obtained polyurethane peppermint oil microcapsule is shown in figure 1 by observing the obtained polyurethane peppermint oil microcapsule through a metallographic microscope (LW600LJT, Shanghai Measure vitamin photoelectric technology Co., Ltd.), and the microcapsule is spherical, has a smooth surface and is poor in uniformity.
Example 2
The polyurethane peppermint oil microcapsule comprises the following raw materials:
the preparation method of the polyurethane peppermint oil microcapsule comprises the following specific steps:
(a) weighing arabic gum and dissolving the arabic gum in deionized water to prepare a arabic gum solution; weighing the isocyanate prepolymer and peppermint oil, mixing for 2min under magnetic stirring of 600r/min, and performing ultrasonic treatment for 2min to obtain an isocyanate prepolymer-peppermint oil mixed oil phase;
(b) b, adding the Arabic gum solution prepared in the step a into the oil phase prepared in the step a at the speed of 50mL/h, and mixing for 10min under the magnetic stirring of 500 r/min; then ultrasonic cell crushing treatment is carried out for 10min to obtain O/W emulsion of isocyanate prepolymer-peppermint oil-Arabic gum;
(c) weighing polysaccharide, and dissolving the polysaccharide in deionized water to obtain a polysaccharide solution;
(d) c, under the condition of magnetic stirring at 800r/min, adding the polysaccharide solution prepared in the step c into the O/W emulsion obtained in the step b at the temperature of 50 ℃; heating to 70 ℃ and reacting for 2h to obtain polyurethane peppermint oil microcapsule suspension;
(e) cooling the polyurethane peppermint oil microcapsule suspension obtained in the step d to room temperature, and centrifuging at 11000 r/min; decanting, filtering, washing with water for 3 times, and vacuum freeze drying the suspension for 24 hr to obtain polyurethane peppermint oil microcapsule.
The average particle size of the prepared polyurethane peppermint oil microcapsule is 8.7 mu m, and the load rate is 23.37%.
Example 3
The polyurethane peppermint oil microcapsule comprises the following raw materials:
the preparation method of the polyurethane peppermint oil microcapsule comprises the following specific steps:
(a) weighing arabic gum and dissolving the arabic gum in deionized water to prepare a arabic gum solution; weighing the isocyanate prepolymer and the peppermint oil, mixing for 2min under the condition of magnetic stirring at 500r/min, and carrying out ultrasonic treatment for 1min to obtain an isocyanate prepolymer-peppermint oil mixed oil phase;
(b) b, adding the Arabic gum solution prepared in the step a into the oil phase prepared in the step a at the speed of 50mL/h, and mixing for 10min under the magnetic stirring of 500 r/min; then ultrasonic cell crushing treatment is carried out for 10min to obtain O/W emulsion of isocyanate prepolymer-peppermint oil-Arabic gum;
(c) weighing polysaccharide, and dissolving the polysaccharide in deionized water to obtain a polysaccharide solution;
(d) c, under the condition of magnetic stirring at 800r/min, adding the polysaccharide solution prepared in the step c into the O/W emulsion obtained in the step b at the temperature of 50 ℃; heating to 70 ℃, and reacting for 2h to obtain polyurethane peppermint oil microcapsule suspension;
(e) d, cooling the polyurethane peppermint oil microcapsule suspension obtained in the step d to room temperature, and centrifuging at 11000 r/min; decanting, filtering, washing with water for 3 times, and vacuum freeze drying the suspension for 24 hr to obtain polyurethane peppermint oil microcapsule.
The average particle size of the prepared polyurethane peppermint oil microcapsule is 8.11 mu m, and the load rate is 22.79 percent.
Example 4
The polyurethane peppermint oil microcapsule comprises the following raw materials:
the preparation method of the polyurethane peppermint oil microcapsule comprises the following specific steps:
(a) weighing arabic gum and dissolving the arabic gum in deionized water to prepare a arabic gum solution; weighing the isocyanate prepolymer and the peppermint oil, mixing for 2min under magnetic stirring of 400r/min, and carrying out ultrasonic treatment for 3min to obtain an isocyanate prepolymer-peppermint oil mixed oil phase;
(b) adding the Arabic gum solution prepared in the step a into the oil phase prepared in the step a at the speed of 50mL/h, and mixing for 15min under the magnetic stirring of 500 r/min; then ultrasonic cell crushing treatment is carried out for 10min to obtain O/W emulsion of isocyanate prepolymer-peppermint oil-Arabic gum;
(c) weighing polysaccharide, and dissolving the polysaccharide in deionized water to obtain a polysaccharide solution;
(d) under the condition of magnetic stirring at 800r/min, adding the polysaccharide solution prepared in the step c into the O/W emulsion obtained in the step b at the temperature of 60 ℃; heating to 70 ℃, and reacting for 1.5h to obtain polyurethane peppermint oil microcapsule suspension;
(e) cooling the polyurethane peppermint oil microcapsule suspension obtained in the step d to room temperature, and centrifuging at 11000 r/min; decanting, filtering, washing with water for 3 times, and vacuum freeze drying the suspension for 24 hr to obtain polyurethane peppermint oil microcapsule.
The average particle size of the prepared polyurethane peppermint oil microcapsule is 3.08 mu m, and the load rate is 25.14%.
Example 5
The polyurethane peppermint oil microcapsule comprises the following raw materials:
the preparation method of the polyurethane peppermint oil microcapsule comprises the following specific steps:
(a) weighing arabic gum and dissolving the arabic gum in deionized water to prepare a arabic gum solution; weighing the isocyanate prepolymer and the peppermint oil, mixing for 2min under magnetic stirring at 500r/min, and performing ultrasonic treatment for 1min to obtain an isocyanate prepolymer-peppermint oil mixed oil phase;
(b) b, adding the Arabic gum solution prepared in the step a into the oil phase prepared in the step a at the speed of 50mL/h, and mixing for 10min under the magnetic stirring of 500 r/min; then ultrasonic cell crushing treatment is carried out for 10min to obtain O/W emulsion of isocyanate prepolymer-peppermint oil-Arabic gum;
(c) weighing polysaccharide, and dissolving the polysaccharide in deionized water to obtain a polysaccharide solution;
(d) c, under the condition of magnetic stirring at 800r/min, adding the polysaccharide solution prepared in the step c into the O/W emulsion obtained in the step b at the temperature of 50 ℃; heating to 70 ℃ and reacting for 1.5h to obtain polyurethane peppermint oil microcapsule suspension;
(e) d, cooling the polyurethane peppermint oil microcapsule suspension obtained in the step d to room temperature, and centrifuging at 11000 r/min; decanting, filtering, washing with water for 3 times, and vacuum freeze drying the suspension for 24 hr to obtain polyurethane peppermint oil microcapsule.
The average particle size of the prepared polyurethane peppermint oil microcapsule is 1.68 mu m, and the loading rate is 26.79 wt%.
The obtained polyurethane peppermint oil microcapsule is observed by a metallographic microscope (LW600LJT, Shanghai Megaku photo-electro technology Co., Ltd.), and the appearance of the obtained polyurethane peppermint oil microcapsule is shown in figure 2, and the capsule is spherical, has a smooth surface, small particle size and is uniformly distributed.
In summary, the particle size and the loading rate of the polyurethane peppermint oil microcapsule can be controlled by changing the dosage, the temperature, the stirring speed and the like of the arabic gum, the isocyanate prepolymer, the peppermint oil and the polysaccharide. Finally, the polyurethane peppermint oil microcapsule with uniform particle size and good shape is obtained, the average particle size is 1.68-8.11 mu m, and the load rate is 22-29%.
Claims (9)
1. The polyurethane peppermint oil microcapsule is characterized in that the raw materials comprise the following components in percentage by mass:
2. the polyurethane peppermint oil microcapsule according to claim 1, wherein the polyisocyanate is a prepolymer of toluene diisocyanate.
3. The polyurethane peppermint oil microcapsule according to claim 1, wherein said polysaccharide is xylitol.
4. A process for the preparation of polyurethane peppermint oil microcapsules according to any of claims 1 to 3, comprising the steps of:
step 1): mixing polybasic isocyanate and peppermint oil to obtain oil phase;
step 2): uniformly mixing Arabic gum with deionized water to obtain a water phase;
step 3): slowly adding water phase into the oil phase, and emulsifying with ultrasonic cell pulverizer to obtain oil-in-water stable emulsion containing peppermint oil;
step 4): adding a polysaccharide solution into the emulsion obtained in the step 3) under the condition of heating and stirring, and reacting to obtain a suspension containing the polyurethane peppermint oil microcapsule;
step 5): and (3) sequentially centrifuging, decanting, filtering, washing and drying the suspension to collect the polyurethane peppermint oil microcapsules.
5. The preparation method according to claim 4, wherein the mixing in step 1) is specifically: mixing for 2-4 min under magnetic stirring at 300-600 r/min; and (4) carrying out ultrasonic treatment for 1-3 min.
6. The preparation method according to claim 4, wherein the step 2) is specifically: adding the Arabic gum solution into the oil phase at the speed of 30-80 mL/h, mixing for 10-15 min under the magnetic stirring of 300-600 r/min, and then carrying out ultrasonic cell crushing treatment for 10-15 min.
7. The preparation method according to claim 4, wherein the step 4) is specifically: adding the polysaccharide solution into the emulsion at 40-50 ℃ under magnetic stirring at 300-600 r/min, and then reacting for 1.0-2.5 h at 60-70 ℃.
8. The preparation method according to claim 4, wherein the rotation speed of the centrifugation in the step 5) is 7000 to 11000 r/min; the washing times are 2-4 times; the drying adopts vacuum freeze drying for 24 h.
9. The preparation method according to claim 4, wherein the average particle size of the polyurethane peppermint oil microcapsule obtained in step 5) is 1.68 to 8.11 μm.
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| CN115301171A (en) * | 2022-08-15 | 2022-11-08 | 扬州市祥华新材料科技有限公司 | Preparation method of waterborne polyurethane microcapsule emulsion based on peppermint oil as core and application of waterborne polyurethane microcapsule emulsion to printing ink |
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| CN113174759A (en) * | 2021-04-22 | 2021-07-27 | 南通欣颐家纺有限公司 | Preparation method of plant-derived slow-release mosquito-proof microcapsule |
| CN115301171A (en) * | 2022-08-15 | 2022-11-08 | 扬州市祥华新材料科技有限公司 | Preparation method of waterborne polyurethane microcapsule emulsion based on peppermint oil as core and application of waterborne polyurethane microcapsule emulsion to printing ink |
| CN115301171B (en) * | 2022-08-15 | 2023-12-29 | 扬州市祥华新材料科技有限公司 | Preparation method of aqueous polyurethane microcapsule emulsion based on peppermint oil as core and application of aqueous polyurethane microcapsule emulsion to printing ink |
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