CN111569793A - Cationic self-dispersion stable closed essence microcapsule and preparation and application thereof - Google Patents

Cationic self-dispersion stable closed essence microcapsule and preparation and application thereof Download PDF

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CN111569793A
CN111569793A CN202010365973.0A CN202010365973A CN111569793A CN 111569793 A CN111569793 A CN 111569793A CN 202010365973 A CN202010365973 A CN 202010365973A CN 111569793 A CN111569793 A CN 111569793A
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essence
diisocyanate
essential oil
microcapsule
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CN111569793B (en
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闵洁
陈晓旋
郑丽娟
苏梦
许晓敏
孙潇
夏浩宇
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Guangdong Nikeer Clothing Co ltd
Donghua University
National Dong Hwa University
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Donghua University
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    • 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
    • A—HUMAN NECESSITIES
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Abstract

The invention relates to a cationic high-self-dispersion stable closed essence microcapsule and a preparation method and application thereof. The microcapsule takes a polyurethane compound containing a tertiary amine cationic group structure as a shell material and natural plant essential oil as a core material. The method comprises the following steps: diisocyanate, dihydroxyethyl fatty amine and a catalyst react in a solvent, the obtained diisocyanate prepolymer containing fatty tertiary amine and natural essence oil are mixed, an acidic aqueous solution containing polyol is added, emulsification is carried out, and then addition polymerization reaction is carried out under certain temperature and time conditions, so as to form a high-molecular shell structure. The method ensures that the essence microcapsule is in a cationic characteristic in a weak acid solution through the cationic structure of the tertiary amine, increases the surface potential of microcapsule particles, and improves the dispersion stability of the essence microcapsule.

Description

Cationic self-dispersion stable closed essence microcapsule and preparation and application thereof
Technical Field
The invention belongs to the field of microcapsule materials and preparation and application thereof, and particularly relates to a cationic high-self-dispersion stable closed essence microcapsule and a preparation method and application thereof.
Background
The microcapsule technology is a technology for coating solid or liquid with a film-forming material to form small particles, and the essence is to isolate a core material from the external environment through a closed or semi-closed wall film, so that the purposes of protecting and stabilizing the core material, shielding odor and color and controlling the release of the core material are achieved. The microencapsulation has the significance of effectively and durably reducing the influence of external environmental factors such as oxygen, humidity, heat, light and other substances on the core material, effectively preventing the external factors from damaging the core material substance, reducing the diffusion or volatilization of the core material to the environment, inhibiting the volatilization loss of effective active ingredients in the core material, improving the stability of the core material, keeping the quality lasting, manually and effectively controlling the release of the core material, exerting the original effect of the core material to the maximum extent, improving the stability of the physical and chemical properties of the core material, and converting liquid or semisolid fluid into free-flowing solid powder.
The textile with fragrant smell gives a fragrant and pleasant feeling to consumers, but the essence has very complex composition, contains most of volatile organic components and unstable chemical properties, so in order to protect the essence from the influence of external environment during use and storage, the fragrance is slowly released, and the purpose of prolonging the fragrance preservation period is achieved, and the essence is preferably microencapsulated.
The essence microcapsule is used as a functional finishing agent for textiles, is prepared into finishing agents of various textile products in manners of emulsification, dispersion and the like to process the textile products, and is stored in a water dispersion system in the storage process.
The surface structure of the essence microcapsules and the particle size of the essence microcapsules determine that most of the essence microcapsules have the defect of easy delamination, and although the addition of the dispersing agent and the use of the protective colloid can improve the dispersion stability of the essence microcapsules to a certain extent, the dispersing agent on the surfaces of the essence microcapsules is easy to desorb along with the prolonging of the storage time, and finally the precipitation delamination of the essence microcapsules is caused, and the delamination phenomenon brings difficulty to the application of consumers.
Meanwhile, the shell structure of most essence microcapsules does not have charge characteristics, so that the weight of the essence microcapsule particles in an aqueous solution is influenced, and the reasonable use of consumers is influenced; meanwhile, as the electrical characteristics of the essence microcapsule particles, the fabric surface is difficult to adhere through the action of charges due to the lack of adsorbability to fibers, so that the synthesized essence microcapsule with the cationic characteristic can effectively adhere to the surface of the fabric by utilizing the adsorption characteristic of opposite charges, the transfer efficiency of the essence microcapsule to the fabric in aqueous solution is improved, and the utilization rate of the essence microcapsule is increased.
The preparation of the cationic essence microcapsule is that the surface of the microcapsule particle forms the charge characteristic of cation, which increases the charge repulsion among the microcapsule particles and can ensure the dispersion stability of the microcapsule dispersion liquid.
Disclosure of Invention
The invention aims to solve the technical problem of providing a cationic high-self-dispersion stable closed essence microcapsule and preparation and application thereof, so as to overcome the defect of poor dispersion stability of the essence microcapsule in the prior art.
The invention provides a cationic essence microcapsule, which takes a polyurethane compound containing a tertiary amine cationic group structure as a shell material and natural plant essential oil as a core material; the polyurethane compound containing the tertiary amine cationic group structure is obtained by reacting diisocyanate, dihydroxyethyl fatty amine and a catalyst, and carrying out addition polymerization on the obtained diisocyanate prepolymer containing the fatty tertiary amine and polyol under an acidic condition.
The polyurethane compound containing the tertiary amine cationic group structure plays a role in sealing volatilization of low-molecular essence.
The invention also provides a preparation method of the cationic essence microcapsule, which comprises the following steps:
(1) reacting diisocyanate, dihydroxyethyl fatty amine and a catalyst in a solvent to obtain a diisocyanate prepolymer containing fatty tertiary amine, wherein the ratio of the diisocyanate to the dihydroxyethyl fatty amine to the catalyst to the solvent is 165-265g, 160-170g, 0.002-0.08g and 90-250 mL;
(2) and (2) mixing the diisocyanate prepolymer containing the fatty tertiary amine in the step (1) with natural essence essential oil, adding an acidic aqueous solution containing polyol, emulsifying, and performing addition polymerization reaction to obtain the cationic essence microcapsule, wherein the mass ratio of the diisocyanate prepolymer containing the fatty tertiary amine in the step (1), the natural essence essential oil, the polyol and the acid is 32-36:30-50:5-7: 5-7.
The diisocyanate in the step (1) is at least one of aromatic diisocyanate and aliphatic diisocyanate.
The aromatic diisocyanate is TDI, hydrogenated MDI or MDI; the aliphatic diisocyanate is HDI or IPDI.
The dihydroxyethyl fatty amine in the step (1) is dihydroxyethyl fatty amine with the carbon length of between 8 and 18, and preferably dihydroxyethyl hexadecylamine or dihydroxyethyl octadecylamine.
The catalyst in the step (1) is dibutyltin dilaurate; the solvent is anhydrous acetone.
The reaction temperature in the step (1) is 50-70 ℃, and the reaction time is 3-12 h.
The natural essence essential oil in the step (2) is at least one of lavender essential oil, geranium essential oil, chamomile essential oil, mint essential oil and honeysuckle essential oil.
The polyhydric alcohol in the step (2) is ethylene glycol or glycerol; the acid is acetic acid, succinic acid or lactic acid.
The emulsification time in the step (2) is 30-90 min; the addition polymerization reaction is carried out by heating to 30-45 ℃ and keeping the temperature for 5-7 h.
The invention also provides application of the cationic essence microcapsule in fabric finishing.
The cationic essence microcapsule is padded, printed, coated or sprayed on the textile, and is adhered by a cationic polyurethane adhesive for after-finishing of bedsheets, towels and clothes, and the essential oil components in the perfume microcapsule can be released by mild mechanical friction in daily use to adjust the emotion of a user.
Preparing a finishing agent from the cationic type essence microcapsule, the cationic PU, the non-ionic penetrant and the softening agent, padding the fabric into the finishing agent, and drying to obtain the finished fabric.
The shell material of the microcapsule is a polyurethane compound containing a tertiary amine cationic group structure, and the tertiary amine cationic group on the shell structure of the essence microcapsule increases the positive potential value of the double electric layers on the surfaces of the microcapsule particles, so that larger electrostatic repulsion is generated among the microcapsule particles, and the dispersion stability of the microcapsule in a weakly acidic aqueous solution is improved. Due to the existence of the tertiary amine structure in the diisocyanate prepolymer, the synthesized essence microcapsule can be ensured to have the tertiary amine structure which can play a role in stable dispersion on the shell structure, and in a weak acidic aqueous solution system, the essence microcapsule particles have the characteristic of high dispersion stability by self with positive charges, so that the blending compatibility of the essence microcapsule particles and a cationic compound is improved.
The invention adopts diisocyanate as a shell forming material to synthesize the essence microcapsule shell structure with a polyurethane structure, introduces a tertiary amine structure into the polyurethane shell structure of the essence microcapsule, is combined with the microcapsule shell through a covalent bond, has high physical and chemical stability, and has high fastness in the use process of the essence microcapsule, so that the stable tertiary amine structure ensures that the surface of the essence microcapsule has a stable cation protective layer, stabilizes the electrostatic repulsion among the essence microcapsule particles, and improves the stability of the essence microcapsule in a weak acid aqueous solution system.
The reaction equation for synthesizing the diisocyanate prepolymer containing the tertiary amine structure is as follows:
Figure BDA0002476751960000031
wherein the R group is long chain aliphatic hydrocarbon, the carbon length is between 8 and 18, and the carbon is 16 or 18.
In the water emulsification process of the oil phase system, a certain amount of polyol compounds and organic acids such as ethylene glycol, glycerol, acetic acid, succinic acid, lactic acid and the like are added into an aqueous solution, under the action of mechanical stirring, the oil phase system is dispersed into small oily particles, and a tertiary amine group in a diisocyanate prepolymer containing a tertiary amine structure in the acidic solution is cationized, so that the emulsification and the emulsion stability of the oil phase in a water phase are accelerated, the water solubility of the prepolymer is improved, but the hydrophobicity of the diisocyanate structure in the prepolymer enables the diisocyanate prepolymer containing the tertiary amine structure to be more effectively distributed on the surface layer of the oil phase particles to form oily particles with an inner structure and an outer structure, wherein the inner layer mainly contains essence essential oil components and becomes an essence microcapsule core material structure, and the outer layer mainly contains the diisocyanate prepolymer containing the tertiary amine structure to form a shell structure of an essence microcapsule; in an oil phase water emulsification system, at the interface of oil particles, diisocyanate prepolymer with a cation structure and polyol are subjected to addition reaction to form a macromolecular shell material with a polyurethane structure, so that the stability of essence is protected, the water dispersibility of the essence microcapsules is stabilized, and the chemical reaction equation is as follows:
Figure BDA0002476751960000032
the synthesized essence microcapsule takes natural essence oil as a core material, such as fragrance emitted by lavender essential oil, geranium essential oil, chamomile essential oil and the like, and has the effects of eliminating fatigue and improving sleep quality; or selecting peppermint essential oil, flos Lonicerae essential oil, etc. to play the effects of tranquilizing mind.
The synthesized essence microcapsule has uniform particle size distribution, and meanwhile, the essence microcapsule has high compactness and has airtightness at the temperature of 100-105 ℃, so that the fabric after finishing has fragrance durability in the textile finishing process, and the fragrance durability shows that the fabric still has the effect of releasing fragrance under the condition of mechanical friction after being stored for a long time (6 months).
Advantageous effects
The prepolymer containing the tertiary amine cationic group structure is a shell structure raw material of the microcapsule and has the functions of emulsification and dispersion in the microcapsule synthesis process, and the dispersion stability of the essence microcapsule in a weak acid solution can be ensured through the cationic structure of the tertiary amine, and is independent of the dilution multiple of the solution.
Detailed Description
The invention will be further illustrated with reference to the following specific examples. It should be understood that these examples are for illustrative purposes only and are not intended to limit the scope of the present invention. Further, it should be understood that various changes or modifications of the present invention may be made by those skilled in the art after reading the teaching of the present invention, and such equivalents may fall within the scope of the present invention as defined in the appended claims.
Unless otherwise specified, the reagents used in the following examples are those conventionally commercially available or commercially available, and unless otherwise specified, the methods and apparatuses used in the following examples are those conventionally used in the art.
Example 1
At room temperature, 250 g of MDI is measured and added into a three-neck flask, 250 g of anhydrous acetone is added simultaneously, 165 g of anhydrous dihydroxyethyl octadecylamine is added after uniform stirring, the mixture is heated to 50 ℃ at the speed of 2 ℃/min under the stirring condition, 0.04 g of dehydrated dibutyltin dilaurate is added after reaction for 120 minutes, the reaction is continued for 4 hours, after the NCO group of the reaction system is measured to reach the theoretical value, the temperature is raised to 80 ℃ under the decompression condition, the acetone solvent in the system is removed, and the temperature is reduced to 15 ℃.
250 g of natural lavender essential oil is added into the system, after uniform stirring, a mixed solution of 30 g of ethylene glycol, 29 g of acetic acid and 600 g of water is added, emulsification is carried out under the condition of 3000 r/min of 2000-.
The natural lavender essence microcapsule with the particle size of 2.1-5.0 microns can be obtained through the embodiment; the essence microcapsule solution is stored for 6 months without layering.
Example 2
At room temperature, 262.35 g of hydrogenated MDI is measured and added into a three-neck flask, 200 g of anhydrous acetone is added at the same time, 165 g of anhydrous dihydroxyethyl octadecylamine is added after uniform stirring, the mixture is heated to 70 ℃ at the speed of 2 ℃/min under the stirring condition, 0.045 g of dehydrated dibutyltin dilaurate is added after reaction for 120 minutes, the reaction is continued for 4 hours, after the NCO group of the reaction system is determined to reach the theoretical value, the temperature is raised to 80 ℃ under the decompression condition, the acetone solvent in the system is removed, and then the temperature is reduced to 10 ℃.
160 g of natural chamomile essential oil is added into the system, after the natural chamomile essential oil is uniformly stirred, a mixed solution of 30 g of ethylene glycol, 29 g of acetic acid and 600 g of water is added, emulsification is carried out under the condition of 3000 r/m of 2000-plus materials, heat preservation is carried out for 60 minutes at 10 ℃, then the temperature is raised to 45 ℃, heat preservation is continuously carried out at low speed (400 r/m), and the reaction is finished after stirring is carried out for 8 hours.
The natural chamomile essence microcapsule with the particle size of 2.3-6.2 microns can be obtained through the embodiment, and the essence microcapsule solution is stored for 6 months without layering.
Example 3
Taking the natural fumigation of the above example 1The fine capsule solution of the grass flavor is prepared into a padding solution of a functional finishing agent according to the following formula, and plain all-cotton woven fabric (150 g/m)2) Padding the finishing working solution, and drying at 105 ℃ for 3 minutes to obtain the fabric with recognizable lavender fragrance under the mechanical friction condition.
Figure BDA0002476751960000051
Example 4
The natural chamomile essence microcapsule solution obtained in the example 2 is prepared into a functional finishing agent padding solution according to the following formula, and plain all-cotton woven fabric (150 g/m)2) Padding the finishing working solution, and drying at 105 ℃ for 3 minutes to obtain the fabric which has a recognizable chamomile fragrance under the mechanical friction condition.
Figure BDA0002476751960000052

Claims (8)

1. The cationic essence microcapsule is characterized in that a polyurethane compound containing a tertiary amine cationic group structure is taken as a shell material, and natural plant essential oil is taken as a core material; the polyurethane compound containing the tertiary amine cationic group structure is obtained by reacting diisocyanate, dihydroxyethyl fatty amine and a catalyst, and carrying out addition polymerization on the obtained diisocyanate prepolymer containing the fatty tertiary amine and polyol under an acidic condition.
2. A preparation method of a cationic essence microcapsule comprises the following steps:
(1) reacting diisocyanate, dihydroxyethyl fatty amine and a catalyst in a solvent to obtain a diisocyanate prepolymer containing fatty tertiary amine, wherein the ratio of the diisocyanate to the dihydroxyethyl fatty amine to the catalyst to the solvent is 165-265g, 160-170g, 0.002-0.08g and 90-250 mL;
(2) and (2) mixing the diisocyanate prepolymer containing the aliphatic tertiary amine in the step (1) with natural essence essential oil, adding an acidic aqueous solution containing polyol, emulsifying, and performing addition polymerization reaction to obtain the cationic essence microcapsule, wherein the mass ratio of the diisocyanate prepolymer containing the aliphatic tertiary amine in the step (1), the natural essence essential oil, the polyol and the acetic acid is 32-36:30-50:5-7: 5-7.
3. The method according to claim 2, wherein the diisocyanate in the step (1) is at least one of aromatic diisocyanate and aliphatic diisocyanate; the dihydroxyethyl fatty amine is a dihydroxyethyl fatty amine with a carbon length of between 8 and 18.
4. The method of claim 2, wherein the catalyst in step (1) is dibutyltin dilaurate; the solvent is anhydrous acetone.
5. The method of claim 2, wherein the reaction temperature in step (1) is 50-70 ℃ and the reaction time is 3-12 h.
6. The method according to claim 2, wherein the natural essence essential oil in the step (2) is at least one of lavender essential oil, geranium essential oil, chamomile essential oil, mint essential oil and honeysuckle essential oil; the polyalcohol is ethylene glycol or glycerol; the acid is acetic acid, succinic acid or lactic acid.
7. The method according to claim 2, wherein the emulsification time in step (2) is 30-90 min; the addition polymerization reaction is carried out by heating to 30-45 ℃ and keeping the temperature for 5-7 h.
8. Use of microcapsules according to claim 1 in the finishing of fabrics.
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CN114108316A (en) * 2021-12-13 2022-03-01 罗莱生活科技股份有限公司 Preparation method of antibacterial textile and antibacterial textile
CN114108316B (en) * 2021-12-13 2023-09-15 罗莱生活科技股份有限公司 Preparation method of antibacterial textile and antibacterial textile

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