CN116492498A - Double-layer wound-adherable dressing and preparation method thereof - Google Patents
Double-layer wound-adherable dressing and preparation method thereof Download PDFInfo
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- CN116492498A CN116492498A CN202310563906.3A CN202310563906A CN116492498A CN 116492498 A CN116492498 A CN 116492498A CN 202310563906 A CN202310563906 A CN 202310563906A CN 116492498 A CN116492498 A CN 116492498A
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- polyethylene glycol
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- 239000000853 adhesive Substances 0.000 claims abstract description 39
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/22—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons containing macromolecular materials
- A61L15/24—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/18—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons containing inorganic materials
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/22—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons containing macromolecular materials
- A61L15/26—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/22—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons containing macromolecular materials
- A61L15/28—Polysaccharides or their derivatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/42—Use of materials characterised by their function or physical properties
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/42—Use of materials characterised by their function or physical properties
- A61L15/46—Deodorants or malodour counteractants, e.g. to inhibit the formation of ammonia or bacteria
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/10—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing inorganic materials
- A61L2300/102—Metals or metal compounds, e.g. salts such as bicarbonates, carbonates, oxides, zeolites, silicates
- A61L2300/104—Silver, e.g. silver sulfadiazine
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
- A61L2300/404—Biocides, antimicrobial agents, antiseptic agents
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Hematology (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Materials For Medical Uses (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The invention discloses a double-layer wound-adhesive dressing and a preparation method thereof. Will DCL, PEGDA, agNO 3 Stirring continuously for 3 days after the XG and the AgNPs are dissolved together, reducing the AgNPs in situ, and crosslinking the AgNPs into glue under the action of an ultraviolet initiator I2959 to obtain the adhesion sterilization layer. Then, AM, SBMA, PEGDA and MBAA are poured onto the adhesive sterilization layer so that the upper layer gel precursor liquid diffuses toward the lower layer at the interface; finally, in the case of photoinitiator I 2959 The hydrogel precursor liquid is copolymerized under the action of the catalyst,a bilayer adhesive wound dressing is finally obtained. When the dressing is used, the dressing adhesion sterilization lower layer can absorb EDC/NHS solution to recover the hydrogel state and mediate DCL to perform amidation reaction to enhance adhesion, and AgNPs generated by internal in-situ reduction can be continuously sterilized in the release process; the hydrated zwitterionic polymer PSBMA component in the antibacterial adhesive upper layer can effectively resist adhesion and colonization of bacteria in the external environment, prevent secondary infection and promote normal repair of infected wound tissues.
Description
Technical Field
The invention belongs to the field of functional composite materials, and particularly relates to a double-layer wound-adhesive dressing and a preparation method thereof.
Background
In the biomedical field, suppurative infections, bacteremia, sepsis and the like induced by invasion of pathogenic microorganisms are a large "killer" that jeopardizes the life health and safety of patients. Bacterial attachment and proliferation at wounds caused by skin trauma, burns and various diseases can seriously prevent the wound from healing, and pathological seepage and diffusion can occur at skin tissue injury parts, so that swelling and pain, fever and inflammation of the wound can occur, and the serious patient can also suffer from coma and even death. Currently, a clinically common solution is to inject patients with antibiotic drugs to inhibit the growth of pathogenic bacteria; if the wound is infected deeply and pathogenic seepage occurs, debridement operation and antibiotic medicine supplement are needed for the patient. However, overuse of antibiotic drugs can strengthen the resistance of bacteria and reduce the efficacy of antibiotics. Debridement drainage not only can bring physical pain to patients, but also can cause a certain degree of damage to tissues to prolong the recovery time of patients, and the patients also bear the risk of secondary infection. Therefore, on one hand, bacteria attached to the wound are reduced, and on the other hand, bacteria are effectively and conveniently killed, so that the method has important significance for restraining further infection of the wound and promoting the tissue to recover as soon as possible.
In recent years, hydrogels as a matrix material are given special antibacterial functions as wound dressings, and replacement of conventional gauze materials is receiving attention. Hoque et al prepared an injectable vancomycin-loaded bifunctional hydrogel system, and bacterial experiments showed that the material had remarkable anti-methicillin-resistant staphylococcus aureus (MRSA) characteristics. The antibacterial performance of the hydrogel material system is derived from antibiotics loaded in the material, and the three-dimensional porous structure of the hydrogel is utilized to realize long-acting slow release of the antibiotics, but the problem that the use of the antibiotics further enhances the bacterial drug resistance still cannot be avoided. Guo et al are to form Polydopamine (PDA) in situ inside the polyacrylamide hydrogel, and to use PDA to respond to near infrared light to generate heat effect to realize sterilization. Besides the preparation of materials, the sterilization system not only needs expensive photo-thermal equipment, but also needs irregular photo-thermal operation on tissues to sterilize. In a word, through compounding various antibiotic functional components in the hydrogel, the material can kill pathogenic bacteria through different forms, reaches antibiotic purpose.
In fact, when the antibacterial hydrogel dressing is attached to a tissue wound for sterilization, on one hand, the material needs to be well attached to the wound to kill bacteria, and on the other hand, the material needs to be capable of preventing new bacterial infection and avoiding secondary bacteria infection at the wound. The invention discloses a double-layer dressing capable of adhering to a wound (namely DLH@AgNPs hydrogel) and a preparation method thereof. The material can be stored for a long time after drying and is convenient to use. When the adhesive sterilizing lower layer can absorb EDC/NHS solution to recover the hydrogel state and mediate DCL to generate amidation reaction to enhance adhesion, and AgNPs generated by internal in-situ reduction can continuously kill infected bacteria at a wound in a slow release process; the hydrated zwitterionic polymer PSBMA component in the antibacterial adhesive upper layer can effectively resist adhesion and colonization of bacteria in the external environment, and prevent secondary infection.
Disclosure of Invention
In view of the above-mentioned shortcomings, the present invention discloses a dual-layer wound-attachable dressing and a method of making the same. In order to achieve the above purpose, the invention adopts the following technical scheme:
the patent firstly synthesizes novel functional adhesion copolymer polymethacrylamide levodopa-co-N, N-Dimethylacrylamide (DCL) and double bond terminated polyethylene glycol diacrylate (PEGDA) through the following steps of DCL, PEGDA, agNO 3 And Xanthan Gum (XG) are dissolved together and then stirred continuously for 3 days, and reduced in situ to obtain the product with killing effectAgNPs with fungus function are added in ultraviolet initiator I 2959 Crosslinking into glue under the action to obtain the adhesive sterilizing layer. Then, filling Acrylamide (AM), sulfobetaine methacrylate (SBMA), polyethylene glycol diacrylate (PEGDA) and N, N-methylene bisacrylamide cross-linking agent (MBAA) on the adhesion sterilization layer to enable the upper gel precursor liquid to diffuse towards the lower layer at the interface, so that a good interface bonding effect is ensured; finally, in the case of photoinitiator I 2959 The hydrogel precursor liquid is copolymerized under the action of the hydrogel precursor liquid to finally obtain the double-layer adhesive wound dressing (namely DLH@AgNPs hydrogel), and the material can be stored for a long time after being dried and is convenient to use. When the adhesive sterilizing lower layer of DLH@AgNPs can absorb EDC/NHS solution to recover the hydrogel state and mediate DCL to perform amidation reaction to enhance adhesion, and the in-situ reduction generated AgNPs in the interior can continuously kill infected bacteria at a wound in a slow release process; the hydrated zwitterionic polymer PSBMA component in the antibacterial adhesive upper layer can effectively resist adhesion and colonization of bacteria in the external environment, prevent secondary infection and promote normal repair of infected wound tissues.
The preparation method of the functional composite material comprises the following steps:
(1) 480mL of deionized water was weighed into a round bottom flask, vacuum was applied while stirring, the air dissolved in the water was vented until no more bubbles were generated in the water, and then 12.1g of Na was weighed 2 B 4 O 7 ·10H 2 O and 5g Na 2 CO 3 Is dissolved in the system and is blown into N through a needle 2 30 minutes further ensure that no more excess oxygen is present in the solution system, 3.12g of weighed L-dopa (Levodopa) is added in N 2 Fully dissolved under the protection of atmosphere. After the completion of the dissolution, 10ml of a 50% (v/v) solution of acryloyl chloride in tetrahydrofuran was added dropwise to the reaction system with stirring at 0℃for 30 minutes. Next, at N 2 Adding 9g Na into the reaction system under atmosphere protection 2 CO 3 The reaction was stirred at room temperature at ph=9 for 24 hours. The reaction process is shown as (a):
(2) To H 2 O: dimethyl sulfoxide (DMSO) volume ratio of 15:35 mL of the complex solvent was purged with nitrogen for 30 minutes to ensure as much air as possible was removed from the solvent system. Then, 40mg of AIBN initiator and 388mg of LevodopaMA monomer are weighed into a complex solvent and stirred until completely dissolved (N is needed) 2 Under atmosphere protection). Finally, 2.08mL of N, N-dimethylacrylamide liquid is measured and added into the reaction system, and the temperature of N is kept at 60 DEG C 2 The reaction was stirred continuously for 5 hours under the protection of atmosphere. The reaction process is shown as (b):
(3) 20g of 35000Da PEG powder was weighed and dispersed to 100mL CH 2 Cl 2 Continuously stirring to a transparent and uniform state, then measuring 243 mu L of acrylic chloride to 100mL of PEG, uniformly mixing, finally measuring 160 mu L of triethylamine acid binding agent to the reaction system, promoting the esterification reaction between the acrylic chloride and hydroxyl to be carried out forward, and continuously stirring at normal temperature for 24 hours. The reaction process is shown in (c):
(4) 190mg DCL, 2mg XG and 1mg AgNO 3 The magnetons were dispersed in 1mL deionized water and dissolved with stirring to obtain a clear solution a. Then 2mg I 2959 And 190mg of PEGDA were dispersed in 0.6mL of deionized water to obtain solution B after complete dissolution. And uniformly mixing A, B solution, continuously stirring in a dark place to obtain AgNPs in situ, and preparing the adhesion sterilization layer after photo-crosslinking polymerization into glue. Will 5mg I 2959 The photoinitiator, 288mg SBMA, 120mg AM, 72mg PEGDA and 1mg MBAA are dissolved together in 1.6mL deionized water to form gel precursor liquid, then the precursor liquid is poured on the adhesion sterilization layer and photo-crosslinking is carried out, and finally the double-layer adhesive wound dressing is obtained, and the dressing can be stored for a long time after being dried and is convenient to use.
The invention has the advantages that:
(1) The double-layer adhesive wound dressing prepared by the invention can be stored for a long time in a dry state, and can recover the hydrogel state after hydration, thereby being convenient to use.
(2) The double-layer adhesive wound dressing prepared by the invention can recover the gel state after hydration, has good tensile mechanical toughness and tensile cycle fatigue resistance, and can meet the use requirements of wound infection at the movement parts such as joints and the like.
(3) The adhesive sterilization lower layer of the double-layer adhesive wound dressing prepared by the invention contains a levodopa structure, can adhere skin tissues at an infected wound through catechol action and amidation reaction under the mediation of 0.064 mu M EDC/NHS solution, and simultaneously releases internal in-situ reduced AgNPs to effectively kill infected bacteria.
(4) After the upper antibacterial adhesive hydrogel of the double-layer adhesive wound dressing prepared by the invention is hydrated, the inner PSBMA zwitterionic polymer component of the double-layer adhesive wound dressing can effectively resist adhesion and colonization of bacteria in the external environment, and secondary infection is prevented.
(5) The double-layer adhesive wound dressing prepared by the invention has good water absorption swelling property, is favorable for absorbing pathogenic tissue seepage exuded at wound infection positions, and keeps the moist microenvironment of wound tissues.
Drawings
FIG. 1 is a nuclear magnetic resonance spectrum of levodopa (Levodopa) of acrylamide in example 1.
FIG. 2 is a nuclear magnetic resonance spectrum of polyacrylamide L-dopa-co-N, N-Dimethylacrylamide Copolymer (DCL) of example 2.
FIG. 3 is a nuclear magnetic resonance spectrum of polyethylene glycol diacrylate (PEGDA) of example 3.
Fig. 4 is a tensile stress-strain test chart of the double-layered attachable wound dressing prepared in example 4 after hydration.
FIG. 5 is a graph of cyclic tensile testing after hydration of the bilayer adhesive wound dressing made in example 4.
FIG. 6 is a swelling test chart of the bilayer adhesive wound dressing made in example 4.
FIG. 7 is a graph of tissue adhesion performance of the bilayer adhesive wound dressing prepared in example 4 mediated by EDC/NHS solution.
FIG. 8 is a chart showing the antimicrobial adhesion/sterilization performance test of the dual layer attachable wound dressing made in example 4.
Detailed Description
The following describes specific embodiments of the present invention in detail with reference to the drawings. It should be understood that the detailed description and specific examples, while indicating and illustrating the invention, are not intended to limit the invention.
Unless defined otherwise, technical terms used in the following examples have the same meaning as commonly understood by one of ordinary skill in the art to which the inventive concepts pertain. The test reagents used in the following examples, unless otherwise specified, are all conventional biochemical reagents; the experimental methods are conventional methods unless otherwise specified.
Example 1
In this example, a detailed synthesis of levodopa (Levodopa) is provided, which is followed by the steps:
firstly, 480mL of deionized water was weighed into a round bottom flask, the flask was evacuated with stirring, the air dissolved in the water was vented until no more bubbles were generated in the water, and then 12.1g of Na was weighed 2 B 4 O 7 ·10H 2 O and 5g Na 2 CO 3 Is dissolved in the system and is blown into N through a needle 2 30 minutes further ensure that no more excess oxygen is present in the solution system, 3.12g of weighed L-dopa (Levodopa) is added in N 2 Fully dissolved under the protection of atmosphere. After the completion of the dissolution, 10ml of a 50% (v/v) solution of acryloyl chloride in tetrahydrofuran was added dropwise to the reaction system with stirring at 0℃for 30 minutes. Next, at N 2 Adding 9g Na into the reaction system under atmosphere protection 2 CO 3 The reaction was stirred at room temperature at ph=9 for 24 hours. After the reaction is completed, concentrated hydrochloric acid is gradually added into the reaction mixture to adjust the pH to be=2 until no bubbles are generated in the solution, and then the solution is repeatedly extracted with ethyl acetate for three times without usingWater MgSO 4 And (3) drying the organic solution, concentrating the product by rotary evaporation, and precipitating with n-hexane to obtain the double bond modified Levodopa monomer. As shown in FIG. 1, nuclear magnetic resonance spectroscopy showed successful synthesis of LevodopaMA monomer.
Example 2
In this example, a detailed synthesis of the polyacrylamide L-dopa-co-N, N-Dimethylacrylamide Copolymer (DCL) is provided, which is as follows:
first, to H 2 O: DMSO volume ratio of 15:35 mL of the complex solvent was purged with nitrogen for 30 minutes to ensure as much air as possible was removed from the solvent system. Then, 40mg of AIBN initiator and 388mg of LevodopaMA monomer are weighed into a complex solvent and stirred until completely dissolved (N is needed) 2 Under atmosphere protection). Finally, 2.08mL of N, N-dimethylacrylamide liquid is measured and added into the reaction system, and the temperature of N is kept at 60 DEG C 2 The reaction was stirred continuously for 5 hours under the protection of atmosphere. After the reaction time is over, the product is dialyzed for three days by a dialysis bag to remove unreacted small molecules and oligomers, and the DCL is obtained after freeze-drying. As shown in FIG. 2, nuclear magnetic resonance spectroscopy indicated that DCL copolymer was synthesized.
Example 3
In this example, a detailed synthesis of polyethylene glycol diacrylate (PEGDA) is provided, comprising the steps of:
first, 20g of 35000Da PEG powder was weighed and dispersed into 100mL of CH 2 Cl 2 Continuously stirring to a transparent and uniform state, then measuring 243 mu L of acrylic chloride, adding into 100mL of PEG organic solution system, uniformly mixing, finally measuring 160 mu L of triethylamine acid binding agent into the reaction system, promoting the esterification reaction between the acrylic chloride and hydroxyl to be carried out forward, and continuously stirring at normal temperature for 24 hours. After the reaction was completed, 30mL of a solution having a concentration of 2. 2M K was added to the reaction mixture 2 CO 3 The aqueous solution was vigorously stirred for 30 minutes; then 100mL of saturated NaCl solution is added to promote phase separation of the organic phase and the aqueous phase, and the organic phase is separated and used for CH 2 Cl 2 Repeated extraction of the aqueous phase three times ensures that there is sufficient transfer of the PEGDA product to CH 2 Cl 2 Middle%With anhydrous MgSO 4 Drying is carried out); finally, the organic solvent was removed by rotary evaporation to give a polyethylene glycol diacrylate (PEGDA) end-capped at both ends. As shown in FIG. 3, nuclear magnetic resonance spectroscopy indicated successful synthesis of the PEGDA copolymer.
Example 4
In this example, a detailed process for preparing the bilayer adhesive wound dressing is provided, comprising the steps of:
first, 190mg of DCL, 2mg of XG and 1mg of AgNO were mixed 3 The magnetons were dispersed in 1mL deionized water and dissolved with stirring to obtain a clear solution a. Then 2mg I 2959 And 190mg of PEGDA were dispersed in 0.6mL of deionized water to obtain solution B after complete dissolution. And uniformly mixing A, B solution, continuously stirring for 3 days in a dark place to obtain AgNPs in situ, and injecting the AgNPs into a mold to prepare the adhesive sterilization layer through photo-crosslinking polymerization. Will 5mg I 2959 The photoinitiator, 288mg SBMA, 120mg AM, 72mg PEGDA and 1mg MBAA are dissolved in 1.6mL deionized water together to form gel precursor liquid, then the precursor liquid is poured into a mold to be spread on an adhesion sterilization layer, and a stable and reliable bonding interface is formed after photo-crosslinking into gel, so that the double-layer adhesive wound dressing is finally obtained, and the dressing can be stored for a long time after being dried and is convenient to use.
Test example 1
This test example provides a tensile mechanical test of the bilayer adhesive wound dressing made in example 4, which test procedure is as follows:
firstly, hydrating the double-layer adhesive wound dressing prepared in the embodiment 4, clamping the double-layer adhesive wound dressing on a clamp matched with a universal mechanical testing machine (the measuring range of a sensor is 20 kg) after recovering the gel state, adjusting the position of the clamp of the mechanical testing machine to keep the state that a material is just clamped between an upper clamp and a lower clamp, and carrying out uniaxial stretching at the speed of 100mm/min until the material breaks, and stopping. The DLH@AgNPs hydrogel is clamped on a mechanical testing machine according to the same sample loading mode and kept in a state of just clamping the material, the sample is stretched to a 400% strain position at the speed of 100mm/min, the initial state is returned according to the speed of 100mm/min, and the sample is circularly stretched for 11 times. As shown in fig. 4, the tensile stress-strain test results indicate that the material has good flexibility. As shown in fig. 5, the cyclic tensile test results indicate that the material has good fatigue resistance.
Test example 2
This test example provides a swelling test for the bilayer adhesive wound dressing made in example 4, which test procedure is as follows:
the hydrogel prepared in example 4 after the double-layer adhesive wound dressing is dried is weighed, the initial mass is recorded, the material in a dry state is soaked in deionized water at room temperature for swelling, 13 different time nodes are selected within the swelling time of 0-33 hours, the hydrogel is taken out and the swelling mass of the corresponding time node is recorded after the superfluous water on the surface is wiped off, and the swelling rate is calculated. As shown in fig. 6, the double-layered attachable wound dressing has good water absorption capacity, helping to absorb pathological exudates at the wound infection site.
Test example 3
This test example provides a 180 ° tissue adhesion peel test for the dual layer attachable wound dressing prepared in example 4 under EDC/NHS solution mediation, which test procedure is as follows:
first, a pre-prepared 0.064 μm EDC/NHS solution was sprayed on the surface of pigskin to wet the surface of pigskin tissue, then the lower adhesive sterilizing layer of the double-layered adhesive wound dressing prepared in example 4 was attached to pigskin tissue and pressed with a 100g weight for 5 minutes so that adhesion was formed at the interface of the double-layered adhesive wound dressing and pigskin tissue (a 5-10mm position was reserved for clamping by a convenient jig), and after it recovered to the gel state, the test was performed. The upper and lower clamps adapted to the texture analyzer are used to hold the two layers of attachable wound dressing and the pig skin tissue in the reserved positions, respectively, the texture analyzer is started and maintained at a rate of 100mm/min for 180 DEG interfacial peel test. As shown in fig. 7, the bilayer adhesive wound dressing has better interfacial adhesion toughness under EDC/NHS solution mediation.
Test example 4
This test example provides an antimicrobial adhesion and sterilization test for the dual layer attachable wound dressing made in example 4, which test procedure is as follows:
10uL 10 8 CFU/mL of E.coliThe bacterial liquid and the staphylococcus aureus bacterial liquid are respectively dripped on the upper surface and the lower surface of the double-layer adhesive wound dressing for 24 hours to be used as an experimental group, and are dripped on a 96TCP (transmission control protocol) pore plate to be used as a control group. After the incubation time is completed, the bacteria inoculation surface and the surface of the pore plate are washed by PBS solution, free floating bacteria are removed, and then the bacteria are dyed by the compound SYTO 9-PI dye, and the anti-fouling effect and the bacterial survival state (red, dead bacteria; green, living bacteria) are observed by photographing under a fluorescence microscope. As shown in fig. 8, the upper surface of the double-layered attachable wound dressing showed good resistance to bacterial adhesion with significantly fewer green spots of fluorescence compared to the TCP orifice plate due to the anti-fouling effect of the PSBMA zwitterionic polymer after hydration; the lower surface of the double-layered attachable wound dressing also limits bacterial proliferation while killing bacteria (red) due to the release of AgNPs.
Claims (10)
1. A method of making a bilayer adhesive wound dressing comprising:
(1) Polyacrylamide L-dopa-co-N, N-dimethylacrylamide, xanthan gum and AgNO 3 Dispersing in deionized water, and stirring by a magnet to obtain a product A;
(2) Initiating the ultraviolet light initiator I 2959 And polyethylene glycol diacrylate are dispersed in deionized water and completely dissolved to obtain a product B;
(3) Uniformly mixing the product A and the product B, continuously stirring in a dark place to obtain AgNPs, and injecting the AgNPs into a mold to obtain an adhesion sterilization layer through photo-crosslinking polymerization;
(4) And pouring gel precursor liquid into the adhesive sterilization layer of the mold for diffusion, and forming a bonding interface after photo-crosslinking into gel to obtain the double-layer adhesive wound dressing.
2. The method of manufacturing according to claim 1, wherein:
the polyacrylamide L-dopa-co-N, N-dimethylacrylamide, xanthan gum and AgNO in the step (1) 3 And the mass ratio of deionized water is 190:2:1:1 respectively.
3. The method of manufacturing according to claim 1, wherein:
the polyacrylamide L-dopa-co-N, N-dimethylacrylamide in the step (1) is prepared by the following method:
under a buffer system, carrying out amidation reaction on the acryloyl chloride and the levodopa to synthesize an acrylamide levodopa monomer for standby;
and (3) copolymerizing an acrylamide levodopa monomer and N, N-dimethylacrylamide to obtain the polyacrylamide levodopa-co-N, N-dimethylacrylamide.
4. A method of manufacture according to claim 3, wherein:
the buffer system ph=9.
5. The method of manufacturing according to claim 1, wherein:
the ultraviolet initiator I in the step (2) 2959 The mass ratio of the polyethylene glycol diacrylate to the deionized water is 2:190:0.6.
6. The method of manufacturing according to claim 1, wherein:
the polyethylene glycol diacrylate in the step (2) is prepared by the following method:
and (3) carrying out esterification reaction on the acryloyl chloride and 35000Da polyethylene glycol to synthesize polyethylene glycol diacrylate for later use.
7. The method of manufacturing according to claim 1, wherein:
the continuous stirring time in the step (3) is 3 days.
8. The method of manufacturing according to claim 1, wherein:
the gel precursor liquid in the step (4) is prepared by the following method:
will I 2959 The photoinitiator, the sulfobetaine methacrylate, the acrylamide, the polyethylene glycol diacrylate and the N, N-methylene bisacrylamide cross-linking agent are dissolved in deionized water, and gel precursor liquid is obtained.
9. The method of manufacturing according to claim 8, wherein:
the I is 2959 The mass ratio of the photoinitiator to the sulfobetaine methacrylate to the acrylamide to the polyethylene glycol diacrylate to the N, N-methylene bisacrylamide crosslinking agent to the deionized water is as follows: 5:288:120:72:1:1.6.
10. A bilayer adherable wound dressing made according to the method of any one of claims 1 to 9.
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