CN112030566B - Sustained-release ectoin microcapsule and preparation method and application thereof - Google Patents
Sustained-release ectoin microcapsule and preparation method and application thereof Download PDFInfo
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- CN112030566B CN112030566B CN202011061177.4A CN202011061177A CN112030566B CN 112030566 B CN112030566 B CN 112030566B CN 202011061177 A CN202011061177 A CN 202011061177A CN 112030566 B CN112030566 B CN 112030566B
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- hyaluronic acid
- sustained
- ectoin
- release
- microcapsule
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- 239000003094 microcapsule Substances 0.000 title claims abstract description 75
- WQXNXVUDBPYKBA-YFKPBYRVSA-N ectoine Chemical compound CC1=[NH+][C@H](C([O-])=O)CCN1 WQXNXVUDBPYKBA-YFKPBYRVSA-N 0.000 title claims abstract description 54
- 238000013268 sustained release Methods 0.000 title claims abstract description 54
- 239000012730 sustained-release form Substances 0.000 title claims abstract description 54
- 238000002360 preparation method Methods 0.000 title claims abstract description 20
- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 claims abstract description 61
- 229920002674 hyaluronan Polymers 0.000 claims abstract description 60
- 229960003160 hyaluronic acid Drugs 0.000 claims abstract description 60
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims abstract description 58
- 238000006243 chemical reaction Methods 0.000 claims abstract description 40
- 229960003692 gamma aminobutyric acid Drugs 0.000 claims abstract description 29
- OGNSCSPNOLGXSM-UHFFFAOYSA-N (+/-)-DABA Natural products NCCC(N)C(O)=O OGNSCSPNOLGXSM-UHFFFAOYSA-N 0.000 claims abstract description 27
- WQXNXVUDBPYKBA-UHFFFAOYSA-N Ectoine Natural products CC1=NCCC(C(O)=O)N1 WQXNXVUDBPYKBA-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000000376 reactant Substances 0.000 claims abstract description 23
- 239000000463 material Substances 0.000 claims abstract description 12
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- 239000000243 solution Substances 0.000 claims description 34
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- 238000003756 stirring Methods 0.000 claims description 19
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- 238000005406 washing Methods 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 239000000725 suspension Substances 0.000 claims description 13
- 238000001035 drying Methods 0.000 claims description 12
- NWGKJDSIEKMTRX-AAZCQSIUSA-N Sorbitan monooleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O NWGKJDSIEKMTRX-AAZCQSIUSA-N 0.000 claims description 11
- 239000003995 emulsifying agent Substances 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 239000011259 mixed solution Substances 0.000 claims description 11
- 238000000502 dialysis Methods 0.000 claims description 10
- AZKVWQKMDGGDSV-BCMRRPTOSA-N Genipin Chemical compound COC(=O)C1=CO[C@@H](O)[C@@H]2C(CO)=CC[C@H]12 AZKVWQKMDGGDSV-BCMRRPTOSA-N 0.000 claims description 8
- AZKVWQKMDGGDSV-UHFFFAOYSA-N genipin Natural products COC(=O)C1=COC(O)C2C(CO)=CCC12 AZKVWQKMDGGDSV-UHFFFAOYSA-N 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 239000008367 deionised water Substances 0.000 claims description 7
- 229910021641 deionized water Inorganic materials 0.000 claims description 7
- 238000007037 hydroformylation reaction Methods 0.000 claims description 7
- WCDDVEOXEIYWFB-VXORFPGASA-N (2s,3s,4r,5r,6r)-3-[(2s,3r,5s,6r)-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5,6-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@@H]1C[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](C(O)=O)O[C@@H](O)[C@H](O)[C@H]1O WCDDVEOXEIYWFB-VXORFPGASA-N 0.000 claims description 6
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- 229940014041 hyaluronate Drugs 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 238000000967 suction filtration Methods 0.000 claims description 6
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
- 229920002385 Sodium hyaluronate Polymers 0.000 claims description 3
- 239000011575 calcium Substances 0.000 claims description 3
- 229910052791 calcium Inorganic materials 0.000 claims description 3
- 229960005069 calcium Drugs 0.000 claims description 3
- 239000011777 magnesium Substances 0.000 claims description 3
- 229910052749 magnesium Inorganic materials 0.000 claims description 3
- 229940010747 sodium hyaluronate Drugs 0.000 claims description 3
- YWIVKILSMZOHHF-QJZPQSOGSA-N sodium;(2s,3s,4s,5r,6r)-6-[(2s,3r,4r,5s,6r)-3-acetamido-2-[(2s,3s,4r,5r,6r)-6-[(2r,3r,4r,5s,6r)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2- Chemical compound [Na+].CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 YWIVKILSMZOHHF-QJZPQSOGSA-N 0.000 claims description 3
- 239000002357 osmotic agent Substances 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 238000004132 cross linking Methods 0.000 abstract description 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 3
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- 238000010998 test method Methods 0.000 description 3
- 235000010894 Artemisia argyi Nutrition 0.000 description 2
- 241001435059 Artemisia argyi Species 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
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- 239000004677 Nylon Substances 0.000 description 2
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- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- 241001116389 Aloe Species 0.000 description 1
- 241000723436 Chamaecyparis obtusa Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
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- 241000208152 Geranium Species 0.000 description 1
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- 235000011399 aloe vera Nutrition 0.000 description 1
- 150000003862 amino acid derivatives Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000002082 anti-convulsion Effects 0.000 description 1
- 201000008937 atopic dermatitis Diseases 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000004531 blood pressure lowering effect Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
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- 230000007613 environmental effect Effects 0.000 description 1
- 235000008524 evening primrose extract Nutrition 0.000 description 1
- 229940089020 evening primrose oil Drugs 0.000 description 1
- 239000010475 evening primrose oil Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
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- 229930182852 proteinogenic amino acid Natural products 0.000 description 1
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- 230000002936 tranquilizing effect Effects 0.000 description 1
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- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 230000007279 water homeostasis Effects 0.000 description 1
Images
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M23/00—Treatment of fibres, threads, yarns, fabrics or fibrous goods made from such materials, characterised by the process
- D06M23/12—Processes in which the treating agent is incorporated in microcapsules
-
- 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
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/35—Heterocyclic compounds
- D06M13/355—Heterocyclic compounds having six-membered heterocyclic rings
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/01—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with natural macromolecular compounds or derivatives thereof
- D06M15/03—Polysaccharides or derivatives thereof
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/20—Treatment influencing the crease behaviour, the wrinkle resistance, the crease recovery or the ironing ease
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- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Preparation (AREA)
Abstract
The invention discloses a preparation method of an ectoine sustained-release microcapsule, which comprises the following steps: (1) Performing an aldehyde reaction on hyaluronic acid or a derivative thereof to obtain aldehyde-based hyaluronic acid; (2) Reacting the aldehyde hyaluronic acid with gamma-aminobutyric acid to obtain a first reactant; (3) And (3) taking the first reactant as a skin material and the ectoine as a core material to prepare the ectoine sustained-release microcapsule. The invention takes the first reactant obtained after the cross-linking treatment of hyaluronic acid and gamma-aminobutyric acid as a skin material and the ectoin as a core material to prepare the slow-release microcapsule with better slow-release performance.
Description
Technical Field
The invention relates to the technical field of sustained-release microcapsule preparation, in particular to an ectoine sustained-release microcapsule and a preparation method and application thereof.
Background
Sustained-release microcapsules (microcapsules) are semipermeable or sealed micron-sized "containers" with a core-shell structure, which are capable of coating and protecting certain substances, and whose diameter is generally 1-1000 μm.
The sustained-release capsule has wide application in medicine, food, agriculture and animal husbandry, new material and textile. At present, the application in textile is mainly in the aspects of printing dyeing and functional after-finishing, such as electrostatic dyeing, transfer printing, three-dimensional foaming printing, thermosensitive color-changing printing, multi-color-point printing, automatic temperature-adjusting function of fabric, fragrance-retaining finishing, antibacterial and deodorant finishing, flame-retardant finishing and the like. The microcapsule prepared by the artemisia argyi extract is reported to be processed and fixed on nylon fabric, so that the nylon fabric has the functions of moisture retention, antibiosis, deodorization and the like, and has medical value on dermatitis such as eczema, miliaria and the like and skin allergy; the microcapsule prepared from the Artemisia argyi and Chamaecyparis obtusa fabric extracts is used for treating cotton fabric, and has the functions of treating allergic dermatitis and inhibiting pruritus; the health finishing textile produced by the microencapsulated vitamin, the aloe and the evening primrose oil has good health care and skin care effects and is a newly developed medical health care textile variety.
Gamma-aminobutyric acid (CAS number: 56-12-2), also known as 4-aminobutyric acid, GABA for short, is a four-carbon, non-proteinogenic amino acid. Has tranquilizing, hypnotic, anticonvulsive, and blood pressure lowering effects.
Ectoin (Ectoine): is a natural amino acid derivative produced by bacteria living under extreme environmental conditions, can be used as an osmoregulation compatible solute, and can stabilize the barrier function of epithelial tissues. The structural formula is as follows:
ectoin is used as an ingredient in extreme halophilic bacteria, and the most basic function of ectoin is to preserve moisture. It also has many additional functions such as anti-aging, repairing skin barrier, repairing UV damage, etc.
At present, no related report that the sustained-release microcapsule containing gamma-aminobutyric acid and ectoin is applied to textiles is found.
Disclosure of Invention
Aiming at the prior art, the invention aims to provide a preparation method of an ectoine sustained-release microcapsule, which comprises the following steps:
(1) Performing an aldehyde reaction on hyaluronic acid or a derivative thereof to obtain aldehyde-based hyaluronic acid;
(2) Reacting the aldehyde hyaluronic acid with gamma-aminobutyric acid to obtain a first reactant;
(3) And (3) preparing the sustained-release ectoin microcapsule by taking the first reactant as a skin material and the ectoin as a core material.
Specifically, the hyaluronic acid or the derivative thereof comprises one or more of hyaluronic acid, sodium hyaluronate, calcium hyaluronate and magnesium hyaluronate.
Specifically, the step (1) includes: dissolving the hyaluronic acid or the derivative thereof in deionized water to obtain a hyaluronic acid or derivative solution; adding sodium periodate into the hyaluronic acid or the derivative solution thereof, stirring and then carrying out an hydroformylation reaction to obtain a reaction mixed solution; and transferring the reaction mixed solution into a dialysis bag for dialysis to obtain an aldehyde hyaluronic acid solution.
Specifically, the step (2) includes: and adding gamma-aminobutyric acid into the aldehyde hyaluronic acid solution, and reacting for 1-2h at 40-60 ℃ to obtain the first reactant.
Specifically, the step (3) includes: mixing the first reactant with an ectoine aqueous solution with the mass concentration of 10-20%, adding an emulsifier Span-80, stirring for 10-20min at 40-50 ℃, then heating to 60 ℃, adding a glutaraldehyde solution with the mass fraction of 25% as a cross-linking agent, continuing stirring for 20-40min, adjusting the pH of a reaction system to 7-7.5 after the reaction is finished, and obtaining a microcapsule suspension by an interfacial polymerization method; and carrying out suction filtration, washing and drying on the microcapsule suspension to obtain the microcapsule.
Further, in the step (1), the ratio of the hyaluronic acid or the derivative thereof, the deionized water and the sodium periodate is 1g: (40-60) ml: (1.5-2.5) g.
Further, in the step (1), the conditions of the hydroformylation reaction are as follows: reacting for 2-4h at 35-45 ℃.
Further, in the step (2), the addition amount of the gamma-aminobutyric acid is 1-3% of the weight of the aldehydic hyaluronic acid solution.
Further, in the step (3), the first reactant and the aqueous solution of ectoin are added in a volume ratio of 2: (0.5-1).
Further, in the step (3), the emulsifier Span-80 is added in an amount of 0.2-0.6% by weight of the first reactant.
The invention also provides the sustained-release ectoine microcapsule prepared by the preparation method.
The invention also provides an ectoine sustained-release microcapsule, which comprises:
skin material: the leather material is prepared by reacting aldehyde hyaluronic acid with gamma-aminobutyric acid by using aldehyde group and amino group reaction;
core material: is ectoin; wherein the ectoin is wrapped by the skin material to form a sustained-release microcapsule.
Optionally, the microcapsules have a particle size of 0.1um to 100um, preferably 1um to 30um in embodiments of the invention.
Specifically, the hyaluronic acid or the derivative thereof comprises one or more of hyaluronic acid, sodium hyaluronate, calcium hyaluronate and magnesium hyaluronate.
Further, the molecular weight of the hyaluronic acid or the derivative thereof is 6-8 ten thousand.
Specifically, the aldehyde-based hyaluronic acid is prepared by performing an aldehyde reaction on hyaluronic acid or a derivative thereof, and aldehyde groups can be introduced into a polymer skeleton of the hyaluronic acid after the hyaluronic acid is subjected to aldehyde treatment; wherein, optionally, sodium periodate is added to the hyaluronic acid to prepare the aldehyde-modified hyaluronic acid.
The invention also provides the application of the sustained-release ectoine microcapsule in the medical textiles.
The invention also provides a medical textile containing the sustained-release ectoin microcapsule. Wherein the medical textile comprises the ectoine sustained-release microcapsule and a fabric attached with the ectoine sustained-release microcapsule.
Further, the aforementioned medical textile further comprises: osmotic agents JFC and genipin.
The invention also provides a preparation method of the medical textile, which comprises the following steps:
immersing the fabric to be finished into finishing liquid containing the sustained-release microcapsule, and padding for 20-40min; then placing the medical textile in a sizing dryer to pre-dry for 2-4min at 70-80 ℃, then drying for 2-3min at 120-140 ℃, cooling to room temperature, washing with water, and airing to obtain the medical textile.
Furthermore, the finishing liquid contains 150-200g/L of sustained-release microcapsules, 1.0-1.5g/L of penetrating agent JFC and 20-40g/L of genipin.
The invention has the beneficial effects that:
(1) According to the invention, hyaluronic acid and gamma-aminobutyric acid are subjected to cross-linking treatment, so that the gel mechanical strength and stability of hyaluronic acid can be improved; on the other hand, the side effect caused by the contact of the gamma-aminobutyric acid and the skin can be relieved. Then, a first reactant obtained after cross-linking treatment of hyaluronic acid and gamma-aminobutyric acid is used as a skin material, and ectoin is used as a core material, so that the slow-release microcapsule with better slow-release performance is prepared.
(2) According to the invention, genipin is used as a cross-linking agent, the prepared sustained-release microcapsule containing gamma-aminobutyric acid and ectoine is used for carrying out functional finishing on the fabric, and the sustained-release microcapsule is fixed on the fabric, so that the textile with medical and health care effects is prepared, the washing resistance effect of the textile is improved, and meanwhile, the textile is endowed with excellent crease-resistant performance.
Detailed Description
In the prior art, the sustained release technology of the ectoin is less, the release speed of the ectoin is high, and the functions of stabilizing the epithelial tissue barrier and the like of the ectoin cannot be exerted for a long time. The invention aims to provide an ectoine sustained-release microcapsule, a preparation method thereof and a medical textile containing the microcapsule.
In order to make the technical solutions of the present application more clearly understood by those skilled in the art, the technical solutions of the present application will be described in detail below with reference to specific embodiments. The textile fabric of the invention can be pillow towels, bed sheets, hospital gowns and the like, and the examples take the fabric for the pillow towels as an example. The test materials used in the examples of the present invention are all conventional in the art and commercially available. The experimental procedures without specifying the detailed conditions were carried out according to the conventional experimental procedures or according to the instructions recommended by the suppliers.
It should be noted that the following detailed description is exemplary and is intended to provide further explanation of the disclosure. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this application belongs.
Drawings
FIG. 1 shows the results of the sustained-release performance test of example 1 and comparative example 1.
Example 1: preparation of sustained-release microcapsule containing gamma-aminobutyric acid and ectoine
(1) Dissolving 1g of hyaluronic acid (molecular weight is 6-8 ten thousand) in 50ml of deionized water to obtain a hyaluronic acid solution; adding 2.0g of sodium periodate into the hyaluronic acid solution, uniformly stirring, and then carrying out an hydroformylation reaction at the reaction temperature of 40 ℃ for 3 hours to obtain a reaction mixed solution; transferring the reaction mixed solution into a dialysis bag for dialysis to obtain an aldehyde hyaluronic acid solution; adding gamma-aminobutyric acid into the aldehyde hyaluronic acid solution, wherein the addition amount of the gamma-aminobutyric acid is 2% of the weight of the aldehyde hyaluronic acid solution, and reacting for 1.5h at 50 ℃ to obtain a first reactant;
(2) Mixing 30ml of a first reactant with 15ml of an ectoine aqueous solution with the mass concentration of 15%, and adding an emulsifier Span-80, wherein the adding amount of the emulsifier Span-80 is 0.4% of the weight of the first reactant; stirring for 15min at the temperature of 45 ℃, then heating to 60 ℃, adding 5ml of glutaraldehyde solution with the mass fraction of 25%, continuing stirring for reaction for 30min, and adjusting the pH of the reaction system to 7-7.5 after the reaction is finished to obtain microcapsule suspension; and carrying out suction filtration, washing and drying on the microcapsule suspension to obtain the sustained-release microcapsule containing the gamma-aminobutyric acid and the ectoine.
Example 2: preparation of sustained-release microcapsule containing gamma-aminobutyric acid and ectoine
(1) Dissolving 1g of hyaluronic acid (molecular weight is 6-8 ten thousand) in 40ml of deionized water to obtain a hyaluronic acid solution; adding 1.5g of sodium periodate into the hyaluronic acid solution, uniformly stirring, and then carrying out an hydroformylation reaction at the reaction temperature of 35 ℃ for 4 hours to obtain a reaction mixed solution; transferring the reaction mixed solution into a dialysis bag for dialysis to obtain an aldehyde hyaluronic acid solution; adding gamma-aminobutyric acid into the aldehyde hyaluronic acid solution, wherein the addition amount of the gamma-aminobutyric acid is 1% of the weight of the aldehyde hyaluronic acid solution, and reacting for 2h at 40 ℃ to obtain a first reactant;
(2) Mixing 30ml of first reactant with 15ml of 10% aqueous solution of ectoin, and adding an emulsifier Span-80, wherein the addition amount of the emulsifier Span-80 is 0.2% of the weight of the first reactant; stirring for 20min at 40 ℃, then heating to 60 ℃, adding 5ml of glutaraldehyde solution with the mass fraction of 25%, continuing stirring for reaction for 30min, and adjusting the pH of the reaction system to 7-7.5 after the reaction is finished to obtain microcapsule suspension; and carrying out suction filtration, washing and drying on the microcapsule suspension to obtain the sustained-release microcapsule containing the gamma-aminobutyric acid and the ectoine.
Example 3: preparation of sustained-release microcapsule containing gamma-aminobutyric acid and ectoine
(1) Dissolving 1g of hyaluronic acid (molecular weight is 6-8 ten thousand) in 60ml of deionized water to obtain a hyaluronic acid solution; adding 2.5g of sodium periodate into the hyaluronic acid solution, uniformly stirring, and then carrying out an hydroformylation reaction at the reaction temperature of 45 ℃ for 3 hours to obtain a reaction mixed solution; transferring the reaction mixed solution into a dialysis bag for dialysis to obtain an aldehyde hyaluronic acid solution; adding gamma-aminobutyric acid into the aldehyde hyaluronic acid solution, wherein the addition amount of the gamma-aminobutyric acid is 3% of the weight of the aldehyde hyaluronic acid solution, and reacting for 2h at 40 ℃ to obtain a first reactant;
(2) Mixing 30ml of a first reactant with 15ml of an ectoine aqueous solution with the mass concentration of 20%, and adding an emulsifier Span-80, wherein the adding amount of the emulsifier Span-80 is 0.6% of the weight of the first reactant; stirring for 20min at 40 ℃, then heating to 60 ℃, adding 5ml of glutaraldehyde solution with the mass fraction of 25%, continuing stirring for reaction for 30min, and adjusting the pH of the reaction system to 7-7.5 after the reaction is finished to obtain microcapsule suspension; and carrying out suction filtration, washing and drying on the microcapsule suspension to obtain the sustained-release microcapsule containing the gamma-aminobutyric acid and the ectoine.
Example 4: preparation of medical health care textile
Immersing the fabric to be finished into finishing liquid containing the sustained-release microcapsules prepared in the example 1, and padding for 30min; and then placing the fabric in a shaping dryer to pre-dry for 3min at the temperature of 75 ℃, then drying for 2min at the temperature of 130 ℃, cooling to room temperature, washing with water, and airing to obtain the medical health care textile.
The finishing liquid contains 180g/L of slow release microcapsules, 1.2g/L of penetrant JFC and 30g/L genipin.
Example 5: preparation of medical health care textile
Immersing the fabric to be finished into finishing liquid containing the sustained-release microcapsules prepared in the example 1, and padding for 20min; and then placing the fabric in a shaping dryer to pre-dry for 2min at the temperature of 80 ℃, then drying for 2min at the temperature of 140 ℃, cooling to room temperature, washing with water, and airing to obtain the medical health care textile.
The finishing liquid contains 150g/L of slow release microcapsules, 1.5g/L of penetrant JFC and 20g/L of genipin.
Example 6: preparation of medical health care textile
Immersing the fabric to be finished into finishing liquid containing the sustained-release microcapsules prepared in the example 1, and padding for 40min; and then placing the fabric in a shaping dryer to pre-dry for 4min at 70 ℃, then drying for 3min at 120 ℃, cooling to room temperature, washing with water, and airing to obtain the medical health care textile.
The finishing liquid contains 200g/L of slow release microcapsules, 1.0g/L of penetrant JFC and 40g/L genipin.
Comparative example 1: preparation of sustained-release microcapsules
(1) Dissolving 1g of hyaluronic acid (with the molecular weight of 6-8 ten thousand) in 50ml of deionized water to obtain a hyaluronic acid solution; adding 2.0g of sodium periodate into the hyaluronic acid solution, uniformly stirring, and then carrying out an hydroformylation reaction at the reaction temperature of 40 ℃ for 3 hours to obtain a reaction mixed solution;
(2) Mixing 30ml of reaction mixed liquor with 15ml of an ectoin aqueous solution with the mass concentration of 15%, and adding an emulsifier Span-80, wherein the adding amount of the emulsifier Span-80 is 0.4% of the weight of the reaction mixed liquor; stirring for 15min at the temperature of 45 ℃, then heating to 60 ℃, adding 5ml of glutaraldehyde solution with the mass fraction of 25%, continuing stirring for reaction for 30min, and adjusting the pH of the reaction system to 7-7.5 after the reaction is finished to obtain microcapsule suspension; and carrying out suction filtration, washing and drying on the microcapsule suspension to obtain the sustained-release microcapsule.
Comparative example 2: preparation of medical health care textile
Soaking the fabric to be finished into the finishing liquid containing the sustained-release microcapsules prepared in the comparative example 1, and padding for 30min; and then placing the fabric in a shaping dryer to pre-dry for 3min at the temperature of 75 ℃, then drying for 2min at the temperature of 130 ℃, cooling to room temperature, washing with water, and airing to obtain the medical health care textile.
The finishing liquid contains 180g/L of slow release microcapsules, 1.2g/L of penetrant JFC and 30g/L genipin.
Comparative example 3: preparation of medical health care textile
Immersing the fabric to be finished into finishing liquid containing the sustained-release microcapsules prepared in the example 1, and padding for 30min; and then placing the fabric in a sizing dryer to pre-dry for 3min at the temperature of 75 ℃, then drying the fabric for 2min at the temperature of 130 ℃, cooling the fabric to room temperature, washing the fabric with water, and airing the fabric to obtain the medical health care textile.
The finishing liquid contains 180g/L of slow release microcapsules, 1.2g/L of penetrant JFC and 30g/L of adhesive.
The adhesive is APF101 (Zhejiang chemical Co., ltd.).
Test example 1: drug loading and sustained release performance testing
1. The test method comprises the following steps:
the slow release microcapsules prepared in examples 1 to 3 and comparative example 1 were tested for drug-loading rate, and example 1 and comparative example 1 were also tested for slow release performance, with reference to the method of "preparation of geranium microcapsule composite fabric and its drug release mechanism" (journal of textile, vol.39, no. 2, 2018, month 2), wherein the test for drug-loading rate was performed with reference to the method of "1.4.4 drug-loading rate test"; the slow release performance test is adjusted on the basis of '1.4.5 slow release performance test and slow release model fitting', and the method comprises the following steps:
adding 2mg of the sustained-release microcapsule samples prepared in different embodiments and comparative examples into 20ml of PBS, dissolving in water bath at 36 ℃ and at a stirring speed of 100r/min, sampling according to a certain time in the dissolving process, sampling at a sampling interval of 1-12h, sampling at a sampling interval of 3h in 12-24h, sampling at a sampling interval of 4h over 24h, sampling 5ml each time, supplementing volume of PBS into the dissolving system after sampling is finished, and calculating the concentration of ectoin in the dissolving liquid according to an absorbance-concentration standard curve.
2. And (3) test results:
2.1 drug Loading Rate test results
The drug loading rates of the sustained-release microcapsules prepared in example 1 and comparative example 1 are shown in table 1:
table 1: drug loading rate test results
2.2 test results of sustained release performance:
the sustained-release microcapsule prepared in example 1 can realize sustained release for more than 32 hours under the condition of complete infiltration; while the sustained-release microcapsule prepared in comparative example 1 has a sustained-release time of 18 hours under the condition of complete infiltration. Therefore, by adopting the technical scheme of the invention, the sustained-release time of the ectoin is prolonged, and the effect of the ectoin can be exerted for a longer time. The test results are shown in fig. 1.
Test example 2: textile washability test
1. The test method comprises the following steps:
the textiles prepared in example 4, comparative example 2 and comparative example 3 were washed according to the method of GB/T3921.1-1997 and after washing tested for the presence of slow-release microencapsulated ingredients on the fabric surface under IR spectroscopy. The number of washes were recorded when the slow release microcapsule composition on the fabric was washed completely.
2. And (3) test results:
the results of the textile wash durability test are shown in table 2.
Table 2: textile washability test results
| Group of | Number of washes |
| Example 4 | 62 |
| Comparative example 2 | 34 |
| Comparative example 3 | 41 |
Test example 3: evaluation of contact skin sensitization
1. The test method comprises the following steps:
the textile prepared in example 4 was evaluated for contact skin sensitization by reference to the method of "evaluation of contact skin sensitization of nonwoven surgical drape" (modern silk science and technology, 2019 (volume 34), stage 6).
2. And (3) test results:
the animal application test reaction of the textile prepared in the embodiment 4 of the invention has Magnus and Kligman grades of 0; the textile prepared in the embodiment 4 of the invention can not cause contact skin allergic reaction and meets the requirements of medical and health products.
The above description is only a preferred embodiment of the present application and is not intended to limit the present application, and various modifications and changes may be made by those skilled in the art. Any modification, equivalent replacement, improvement and the like made within the spirit and principle of the present application shall be included in the protection scope of the present application.
Claims (9)
1. A preparation method of an ectoine sustained-release microcapsule is characterized by comprising the following steps:
(1) Performing an aldehyde reaction on hyaluronic acid or a derivative thereof to obtain aldehyde-based hyaluronic acid;
(2) Reacting the aldehyde hyaluronic acid with gamma-aminobutyric acid to obtain a first reactant;
(3) Preparing an ectoin sustained-release microcapsule by taking the first reactant as a skin material and the ectoin as a core material; the hyaluronic acid or the derivative thereof is selected from one or more of hyaluronic acid, sodium hyaluronate, calcium hyaluronate and magnesium hyaluronate.
2. The method of claim 1, wherein the step (1) comprises:
dissolving the hyaluronic acid or the derivative thereof in deionized water to obtain a hyaluronic acid or derivative solution; adding sodium periodate into the hyaluronic acid or the derivative solution thereof, stirring and then carrying out an hydroformylation reaction to obtain a reaction mixed solution; and transferring the reaction mixed solution into a dialysis bag for dialysis to obtain an aldehyde hyaluronic acid solution.
3. The method of claim 1, wherein the step (2) comprises:
and adding gamma-aminobutyric acid into the aldehyde hyaluronic acid solution, and reacting for 1-2h at 40-60 ℃ to obtain the first reactant.
4. The method of claim 1, wherein the step (3) comprises:
mixing the first reactant with an ectoine aqueous solution with the mass concentration of 10-20%, adding an emulsifier Span-80, stirring for 10-20min at 40-50 ℃, then heating to 60 ℃, adding a glutaraldehyde solution with the mass fraction of 25%, continuing stirring for reaction for 20-40min, and adjusting the pH of a reaction system to 7-7.5 after the reaction is finished to obtain a microcapsule suspension; and carrying out suction filtration, washing and drying on the microcapsule suspension to obtain the microcapsule suspension.
5. The sustained-release microcapsules of ectoin obtained by the process according to any one of claims 1 to 4.
6. An ectoin sustained-release microcapsule, comprising:
skin material: prepared by reacting aldehyde hyaluronic acid with gamma-aminobutyric acid;
core material: is ectoin; wherein the ectoin is wrapped by the skin material to form a sustained-release microcapsule.
7. Use of the sustained-release microcapsules of ectoin according to claim 6 or 5 in medical textiles.
8. A medical textile comprising the sustained-release microcapsules of ectoin according to claim 6 or 5.
9. The medical textile according to claim 8, further comprising: osmotic agents JFC and genipin.
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| WO2011116962A1 (en) * | 2010-03-24 | 2011-09-29 | Lipotec S.A. | Process of treatment of fibers and/or textile materials |
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| CN110237054A (en) * | 2019-07-11 | 2019-09-17 | 华熙生物科技股份有限公司 | A kind of scar repair material and preparation method thereof |
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| CN1342171A (en) * | 1999-02-03 | 2002-03-27 | 维特罗莱夫英国有限公司 | Process for production of multiple cross-linked hyaluronic acid derivatives |
| WO2011116962A1 (en) * | 2010-03-24 | 2011-09-29 | Lipotec S.A. | Process of treatment of fibers and/or textile materials |
| CN102822413A (en) * | 2010-03-24 | 2012-12-12 | 利普泰股份公司 | Process of treatment of fibers and/or textile materials |
| WO2014023272A1 (en) * | 2012-08-08 | 2014-02-13 | Contipro Biotech S.R.O. | Hyaluronic acid derivative, method of preparation thereof, method of modification thereof and use thereof |
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