CN118852994B - Gel adhesive patch, preparation method and application - Google Patents
Gel adhesive patch, preparation method and application Download PDFInfo
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- CN118852994B CN118852994B CN202411336327.6A CN202411336327A CN118852994B CN 118852994 B CN118852994 B CN 118852994B CN 202411336327 A CN202411336327 A CN 202411336327A CN 118852994 B CN118852994 B CN 118852994B
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- adhesive patch
- gel adhesive
- acrylic acid
- cyclohexylcarbamoyl
- cyclohexyl
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
-
- 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
- A61L15/42—Use of materials characterised by their function or physical properties
- A61L15/58—Adhesives
-
- 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
- A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
- A61L24/04—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials
- A61L24/06—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
- C09J7/10—Adhesives in the form of films or foils without carriers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Hematology (AREA)
- Surgery (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Materials For Medical Uses (AREA)
Abstract
本发明公开了一种凝胶粘合贴片，其组分为N‑环己基‑N‑环己基氨基甲酰基的酰胺化合物、丙烯酸N‑羟基琥珀酰亚胺脂、丙烯酸和光引发剂，其制备方法是将N‑环己基‑N‑环己基氨基甲酰基的酰胺化合物，丙烯酸N‑羟基琥珀酰亚胺脂，丙烯酸，光引发剂溶解至超纯水中得到均匀的前体溶液；将前体溶液注入至模具中并采用光照使其固化；固化后即得凝胶粘合贴片。本发明的凝胶粘合贴片具有优异的力学性能、抗溶胀性能和粘合强度，可应用在皮肤和内脏上，具有良好的应用前景。
The invention discloses a gel adhesive patch, the components of which are an amide compound of N-cyclohexyl-N-cyclohexylcarbamoyl, acrylic acid N-hydroxysuccinimide fat, acrylic acid and a photoinitiator, and the preparation method thereof is to dissolve the amide compound of N-cyclohexyl-N-cyclohexylcarbamoyl, acrylic acid N-hydroxysuccinimide fat, acrylic acid and a photoinitiator in ultrapure water to obtain a uniform precursor solution; the precursor solution is injected into a mold and cured by light; after curing, a gel adhesive patch is obtained. The gel adhesive patch of the present invention has excellent mechanical properties, anti-swelling properties and bonding strength, can be applied to skin and internal organs, and has good application prospects.
Description
Technical Field
The invention relates to the technical field of medical patches, in particular to a gel adhesive patch and a preparation method and application thereof.
Background
The skin is damaged or is subjected to a large area of wound, burn or infectious wound and other common dressings such as gauze to isolate bacteria, so that the healing speed of the skin is slow, and serious consequences can be caused by untimely treatment. In recent years, hydrogels have been used in various fields because of their low cost, skin-friendly, moisture-retaining and good biocompatibility.
For example, chinese patent document CN116392629A, publication No. 2023.7.07 discloses a multifunctional hydrogel dressing, a preparation method and application thereof, wherein the hydrogel dressing has good mechanical properties, excellent biological tissue adhesiveness, broad-spectrum antibacterial property and oxidation resistance. As another example, patent document CN115350321a, publication No. 2022.11.18, discloses a hydrogel dressing and a preparation method thereof, wherein the hydrogel dressing has excellent film forming property and moisture retention property, and has remarkable capability of promoting wound healing rate. However, the hydrogel dressing is mainly used for skin wounds and cannot be applied to wet environments such as viscera.
Although there are many hydrogel adhesive materials with different excellent properties, it is still necessary to develop a gel adhesive product with comprehensive properties and simple preparation method.
Disclosure of Invention
Aiming at the problem that the existing hydrogel adhesive material cannot be applied to wet environments, the invention aims to provide a gel adhesive patch, a preparation method and application thereof, which have excellent mechanical, swelling-resistant and strong adhesive effects and can be applied to the wet environments such as skin or viscera for adhesion.
In a first aspect, the invention provides a gel adhesive patch, which comprises, by mass, 1-12% of an amide compound of N-cyclohexyl-N-cyclohexylcarbamoyl, 30-70% of acrylic acid, 1-10% of N-hydroxysuccinimide ester of acrylic acid, 0.1-1% of a photoinitiator and the balance of ultrapure water.
More preferably, the gel adhesive patch comprises, by mass, 1-4% of an amide compound of N-cyclohexyl-N-cyclohexylcarbamoyl, 56% of acrylic acid, 4% of N-hydroxysuccinimide ester of acrylic acid, 0.1% of a photoinitiator and the balance of ultrapure water.
More preferably, the photoinitiator is selected from any one of phenyl-2, 4, 6-trimethylbenzoyl lithium phosphite (CAS number: 85073-19-4), 2-hydroxy-2-methyl-1- [4- (2-hydroxyethoxy) phenyl ] -1-propanone (CAS number: 106797-53-9), phenylbis (2, 4, 6-trimethylbenzoyl) phosphine oxide (CAS number: 162881-26-7), 1-hydroxycyclohexyl phenyl ketone (CAS number: 947-19-3), 2-dimethoxy-phenyl acetophenone (CAS number: 24650-42-8), or a combination thereof.
More preferably, the photoinitiator is lithium phenyl-2, 4, 6-trimethylbenzoyl phosphite.
More preferably, the amide compound of N-cyclohexyl-N-cyclohexylcarbamoyl has a structure represented by formula II:
,
Formula II.
In a second aspect, the present invention provides a method for preparing the gel adhesive patch, which specifically includes the following steps:
dissolving an amide compound of N-cyclohexyl-N-cyclohexylcarbamoyl, N-hydroxysuccinimide acrylate, acrylic acid and a photoinitiator into ultrapure water to obtain a uniform precursor solution, injecting the precursor solution into a mold, curing the precursor solution by adopting illumination, and curing the precursor solution to obtain the gel adhesive patch.
As a preferable example, the wavelength of light is 300-700 nm and the illumination time is 2-60 min during curing.
More preferably, the wavelength of light is 365nm and the illumination time is 10min during curing.
In a third aspect, the present invention provides the use of an amide compound or gel adhesive patch as described above for the preparation of a skin or viscera adhesive product.
The invention has the beneficial effects that:
The invention provides a novel amide compound for preparing gel materials, which has excellent anti-swelling performance, the swelling rate of the gel adhesive patch containing the amide compound is 128.3% at the minimum after 24 hours, the gel adhesive patch tends to be stable after 24 hours, the tensile strength of the gel adhesive patch can reach 14.68MPa before swelling balance, the mechanical property is excellent, the adhesive strength of the gel adhesive patch is high, the adhesive strength of the gel adhesive patch on the surface of pig skin can reach 105.1kPa, the adhesive strength of the gel adhesive patch on the surface of pig liver can reach 57.2kPa, and the gel adhesive patch also has better adhesive force on skin and viscera and has good application prospect.
Drawings
FIG. 1 is an H1NMR spectrum of an amide compound of N-cyclohexyl-N-cyclohexylcarbamoyl group.
FIG. 2 is an LC-MS spectrum of an amide compound of N-cyclohexyl-N-cyclohexylcarbamoyl.
Detailed Description
The technical contents of the present invention will be further described with reference to the following examples, which are illustrative, not limiting, and are not intended to limit the scope of the present invention. The test methods used in the examples described below are generally carried out under conventional conditions or under conditions recommended by the manufacturer unless otherwise specified. Materials, reagents and the like used in the examples described below are commercially available unless otherwise specified.
EXAMPLE 1 preparation of N-cyclohexyl-N-cyclohexylcarbamoyl amide compound
122.4G Dicyclohexylcarbodiimide (DCC) and 12.32g 4-Dimethylaminopyridine (DMAP) were added to 122mL Dichloromethane (DCM), 35.75g acrylic acid was slowly added under ice-bath conditions and reacted at room temperature for 12h. The reaction solution is filtered, filtered and mixed, and then dried under reduced pressure to obtain a crude product. The crude product is separated and purified by TLC method with methanol/dichloromethane volume ratio of 1:7 as developing agent and column chromatography with eluent with methanol/dichloromethane volume ratio of 1:10, and concentrated and dried to obtain white solid with 76% yield, and the prepared amide compound of N-cyclohexyl-N-cyclohexylcarbamoyl is N-cyclohexyl-N- (cyclohexylcarbamoyl) acrylamide with the following structural formula:
,
Its H 1 NMR spectrum is shown in FIG. 1 and its ,H1NMR（400MHz, DMSO）：δ8.35(m,1H),δ6.32(m,1H),δ6.16(m,1H),δ5.69(dd,1H),δ4.01(m,1H),δ3.47(m,1H),δ1.73(m,8H),δ1.47(m,4H),δ1.14(m,8H).LC-MS spectrum is shown in FIG. 2, MS (EI): M/z 279 (M+H +).
Example 2 preparation of gel adhesive patches
The N-cyclohexyl-N- (cyclohexylcarbamoyl) acrylamide, the N-hydroxysuccinimide acrylate, the lithium phenyl-2, 4, 6-trimethylbenzoyl phosphite and the ultra pure water prepared in example 1 were prepared in the proportions of table 1 to prepare a uniform precursor solution, and then the precursor solution was injected into a mold and cured with light, with percentages in table 1 being mass%. Wherein the wavelength of light is 365nm, the illumination time is 10min, and the gel adhesive patch is obtained after curing.
Table 1 preparation ratio comparison table of each gel adhesive patch
Example 3 Performance test of gel adhesive patches
1. Swelling Performance test
0.1G of the gel adhesive patch prepared in example 2 was weighed and recorded as an initial weight (W 0), placed in 15mL of physiological saline, respectively, and the swollen hydrogel was taken out of the physiological saline for a fixed period of time, excess water on the surface was gently wiped off and the mass of the gel was recorded, recorded as W t, and then the hydrogel was replaced in physiological saline.
The Swelling Ratio (SR) of the hydrogels was calculated by the formula SR= (W t-W0)/W0 X100%) fixed mass of the gel patches were placed in physiological saline solution and the mass of the gel was observed and recorded for a fixed period of time as shown in Table 2, the swelling ratio was reduced with the addition of N-cyclohexyl-N- (cyclohexylcarbamoyl) acrylamide, the swelling ratio was inversely proportional to the amount of N-cyclohexyl-N- (cyclohexylcarbamoyl) acrylamide added, and a steady state was reached after 24 hours, probably because the addition of the new compound increased the crosslinked gel network crosslinking density, thus inhibiting further swelling of the gel, while the low swelling hydrogels maintained their original shape and mechanical properties, and low swelling gel products were needed when high swelling was not needed in the stricture of the organism or bioadhesion.
TABLE 2 comparison of swelling Properties of gel adhesive patches
2. Tensile Property test
The tensile properties of the hydrogel bars before and after the swelling balance were tested by using an intelligent electronic tensile tester, and the tensile speed was set to be constant at 100mm/min. The hydrogel bars were cut into dumbbell shapes prior to testing. The dumbbell type gel patch has a gauge length of 12mm, a width of 2mm and a thickness of 0.5mm. The tensile strength of the gel patch is determined by the ratio of the maximum force to the cross-sectional area. Each group was repeated 3 times to reduce errors. The results are shown in Table 3, and the tensile strength of groups 2-6 increases before and after the swelling equilibrium after the addition of N-cyclohexyl-N- (cyclohexylcarbamoyl) acrylamide, indicating that the addition of the novel compound enhances the tensile strength of the gel patch.
TABLE 3 tensile Strength control Table for gel adhesive patches
3. Adhesion Performance test
Tensile shear property test was performed on the adhesive strength between the gel adhesive patch and moist tissue (pigskin or pork liver) using a tensile machine to evaluate the adhesive property of the gel adhesive patch. All moist tissues (pigskin or pork liver) are 7cm in length and 2.5cm in width, a poly (methyl methacrylate) film is used as hard back tissue, krazy glue is applied, the length is 10cm, the width is 2.5cm, and the adhesive area of a gel patch is 2.5cm multiplied by 1cm. Before the pigskin or pork liver was adhered, the pigskin was soaked with PBS to simulate a wet physiological environment in vivo. Specifically, the gel adhesive patch was sandwiched between moist tissues and tested after an initial pressurization of 24 hours to ensure balanced expansion of the adhered gel adhesive patch in a moist environment. The self-sealing bag is used for covering the adhesive part in the adhesive process to prevent the tissues and the adhesive film from drying. And (3) testing the gel adhesive patch by adopting a pulling machine at room temperature, setting the constant stretching rate to be 50mm/min, and stretching until the adhesive area is separated from the gel adhesive patch. The tensile shear strength of a gel adhesive patch is determined by dividing the maximum force by the initial adhesion area. Each group was repeated 3 times and the results averaged. As shown in Table 4, the surface adhesion strength of the pigskin and the pig liver of the group 1 is highest, and the adhesion strength is reduced after the N-cyclohexyl-N- (cyclohexylcarbamoyl) acrylamide is added, but the adhesion strength of the group 2 and the group 3 on the surfaces of the pigskin and the pig liver is still higher than that of the group 4-6, which shows that the group can have higher adhesion strength under a wet environment.
TABLE 4 comparison of adhesive strength of gel adhesive patches
The foregoing describes in detail preferred embodiments of the present invention. It should be understood that numerous modifications and variations can be made in accordance with the concepts of the invention without requiring creative effort by one of ordinary skill in the art. Therefore, all technical solutions which can be obtained by logic analysis, reasoning or limited experiments based on the prior art by the person skilled in the art according to the inventive concept shall be within the scope of protection defined by the claims.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018150186A1 (en) * | 2017-02-15 | 2018-08-23 | Tissuemed Limited | Tissue-adhesive materials |
| CN118598790A (en) * | 2024-04-22 | 2024-09-06 | 韦尔通科技股份有限公司 | A modified acrylate and acrylic adhesive composition and its preparation method and application |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6184264B1 (en) * | 1995-08-11 | 2001-02-06 | Smith & Nephew Plc | Adhesives |
| US20130187095A1 (en) * | 2005-12-29 | 2013-07-25 | Designer Molecules, Inc. | Thermosetting adhesive compositions |
| KR20220110797A (en) * | 2019-12-03 | 2022-08-09 | 메사추세츠 인스티튜트 오브 테크놀로지 | fluid resistant tissue adhesive |
| CN116036345A (en) * | 2023-02-16 | 2023-05-02 | 安徽医科大学 | Biocompatible Adhesive Patches for Wet Environments |
| CN118542964A (en) * | 2024-05-15 | 2024-08-27 | 无锡中科光远生物材料有限公司 | A tissue sealant patch and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018150186A1 (en) * | 2017-02-15 | 2018-08-23 | Tissuemed Limited | Tissue-adhesive materials |
| CN118598790A (en) * | 2024-04-22 | 2024-09-06 | 韦尔通科技股份有限公司 | A modified acrylate and acrylic adhesive composition and its preparation method and application |
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