CN115819671A - Copolymer containing NVP structure and application thereof in lubricating coating for interventional catheter - Google Patents
Copolymer containing NVP structure and application thereof in lubricating coating for interventional catheter Download PDFInfo
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- CN115819671A CN115819671A CN202211598765.0A CN202211598765A CN115819671A CN 115819671 A CN115819671 A CN 115819671A CN 202211598765 A CN202211598765 A CN 202211598765A CN 115819671 A CN115819671 A CN 115819671A
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- Materials For Medical Uses (AREA)
Abstract
The invention discloses a copolymer containing an NVP structure, which is characterized by being formed by copolymerizing two monomers, wherein one monomer is NVP, and the other monomer is substituted olefin containing catechol and double bond structures in the structure. Also disclosed is the use thereof as a lubricious coating for interventional catheters, as well as corresponding lubricious coating mixtures for interventional catheters and interventional catheters. The copolymer containing NVP structure provided by the invention can rapidly absorb water to generate lubricating property when contacting water or water in blood, tissue fluid and the like, so that the friction force on the surface of a catheter is reduced to 1/10 or even lower than the original friction force, thereby generating lubricating effect, and can endure repeated friction and keep low friction force in continuous friction, and compared with polyvinylpyrrolidone containing NVP structure but not containing catechol structure, the durable friction number is improved by 5 times or more, thereby showing better firmness.
Description
Technical Field
The invention relates to a copolymer containing an NVP structure and application thereof as a lubricating coating for an interventional catheter, belonging to the technical field of medical instruments.
Background
The interventional therapy is a treatment method which is developed aiming at local lesions based on the fact that an access channel is established through a guide wire, a catheter and the like on the basis of original cavities of a human body such as blood vessels, trachea, esophagus, urethra and the like, and the specific treatment scheme of the used method comprises ablation, expansion, embolism, even excision and the like. In interventional therapy instruments, guide wires are often metal wires and are made of materials such as stainless steel and nickel-titanium alloy, and catheters are often made of various materials such as nylon, polyolefin and polyurethane. When entering the lumen, the guide wire or the catheter can rub against the wall of the lumen, which may cause injury and even spasm of the wall of the lumen, and is often not favorable for treatment. Therefore, such interventional devices often need to have a low coefficient of friction to reduce friction. In addition to the optimization of the catheter material itself, possibly with materials having a lower coefficient of friction, the use of coating techniques to provide lubricity is one of the most important means to reduce the coefficient of friction between the catheter and the wall of the lumen.
The coating materials commonly used at present comprise polyvinylpyrrolidone (PVP), namely a polymer polymerized by vinylpyrrolidone (NVP), polyacrylic acid and a copolymer thereof, polyacrylamide, sodium alginate, hyaluronic acid, polyethylene glycol and the like, wherein PVP is mostly used for practical reuse, and the friction coefficient between the catheter and the cavity wall can be obviously reduced. However, it is not resistant to repeated use, and the coefficient of friction rapidly decreases in the case of multiple uses. Therefore, it is currently critical to find a coating material that has both good lubricating properties and long-term repeated use.
Disclosure of Invention
The invention aims to provide a copolymer based on a vinyl pyrrolidone (NVP) monomer, which has hydrophilicity and can be dissolved in water and alcohol solvents. The copolymer and other additives are dissolved in an alcohol solvent to obtain a coating solution, then the coating solution is coated on the surface of the catheter and is solidified and dried to form a coating surface, and the coating surface rapidly absorbs water when contacting water to generate good lubricity and wear resistance, so that a lubricating effect is achieved.
The purpose of the invention is realized by the following technical scheme:
a copolymer containing an NVP structure is characterized by being formed by copolymerizing two monomers, wherein one monomer is NVP, and the other monomer is substituted olefin of which the structure simultaneously contains catechol and a double-bond structure.
Preferably, the structure is shown as the general formula (I):
wherein R is an alkyl group, an ester group or an amide group;
m/(m+n)>0.5；
the molecular weight of the copolymer is between 1000 and 200 ten thousand.
Preferably, the copolymer has a molecular weight of 5 to 150 ten thousand.
Preferably, the molecular weight of the copolymer is from 60 to 150 ten thousand.
Preferably, m/(m + n) >0.8.
Preferably, the R is methylene, an acetyl ester group or an acetamide group.
The invention also discloses application of the copolymer containing the NVP structure in a lubricating coating for an interventional catheter.
The invention also discloses a lubricating coating for an interventional catheter, which is characterized by comprising the copolymer containing the NVP structure and a solvent.
Preferably, the mass-volume concentration of the copolymer containing NVP structures is 1 to 20%.
Preferably, the solvent is water, or a mixture of water and an alcohol solvent.
Preferably, the liquid also comprises a leveling agent and a stabilizing agent, and the sum of the mass concentrations of the leveling agent and the stabilizing agent is not more than 1%.
The invention also discloses a preparation method of the copolymer containing the NVP structure, which is characterized by comprising the steps of dissolving the NVP monomer in a solvent, adding substituted olefin containing catechol and double bond structures in the structure, stirring uniformly, adding an initiator, carrying out copolymerization reaction, and purifying to obtain the copolymer.
Usable solvents include, but are not limited to, water, alcohol solvents such as methanol, ethanol, isopropanol and the like, ketone solvents such as acetone, butanone and the like can be used as solvents, and can be selected according to different monomer composition systems according to specific conditions such as solubility, reaction temperature and the like; the reaction temperature which can be used is between 40 and 100 ℃, the reaction time generally takes from a few hours to a few tens of hours, the time which is more preferably 2 to 24 hours, and the time which is more preferably 6 to 12 hours.
Purification may be carried out by conventional purification methods, such as dialysis or precipitation washing, to remove residual small molecules.
The invention also discloses an interventional catheter, the surface of which is provided with a coating, the coating is obtained after coating the surface of the catheter with a solution containing NVP copolymer and drying to remove the solvent, the thickness of the coating is about 1-50 μm, preferably 5-20 μm, heating is needed during drying, the heating temperature is higher than room temperature but not more than 60 ℃, preferably 50 +/-5 ℃, the temperature is 50 +/-5 ℃, the solvent is gradually volatilized to remove, the coating is formed on the surface of the catheter, and the contact with water is avoided during the storage process.
The copolymer containing NVP structure and the coating solution formed based on the copolymer series form a coating on the surface of a catheter, when the coating is contacted with water or water in blood, tissue fluid and the like, the coating can rapidly absorb water to generate lubricating property, so that the friction force on the surface of the catheter is reduced to 1/10 or even lower than the original friction force, thereby generating lubricating effect, and in continuous friction, the low friction force can be maintained by enduring repeated friction for many times, compared with polyvinylpyrrolidone containing NVP structure but not containing catechol structure, the durable friction coefficient is improved by 5 times or even more, and the firmer degree is shown. The low friction state can be maintained longer by the introduction of the monomer containing a catechol structure, showing a better degree of firmness. The device has remarkable intentional effects on reducing friction in the interventional therapy process, reducing the damage of the cavity of the human body caused by the friction and improving the experience of patients and medical care personnel in the therapeutic process.
The copolymer is obtained by copolymerization and combination of NVP and different monomers, lubricating performance is brought by utilizing hydrophilic characteristic of PVP, better abrasion resistance and firmness of a hydrophilic coating can be obtained by enhancing adhesive force with a base material by introducing the comonomer, and the lubricating coating can be obtained when the hydrophilic coating is used for an interventional catheter.
Drawings
FIG. 1 shows a general structural formula of a copolymer containing NVP structure.
FIG. 2 is a schematic diagram of the structure of a monomer having both catechol and double bond structures.
FIG. 3 is a structural diagram of a typical monomer containing both catechol and double bond structures, where the boxed portion is an embodiment of R in FIG. 2, (a) is 4-allylcatechol, (b) is 3, 4-dihydroxyphenethylacrylate, and (c) is dopamine methacrylamide.
Fig. 4 shows the results of the friction test of the dried coating.
FIG. 5 is the result of the friction force measured after the water absorption of the coating in example 1.
FIG. 6 is the results of the friction force measured after water absorption of the coating of example 2.
Fig. 7 is a result of the friction force measured after the water absorption of the coating in comparative example 1.
The specific implementation method comprises the following steps:
the present invention is further illustrated by the following examples, which are not intended to limit the scope of the present invention.
FIG. 1 is a general structural formula of the copolymer containing NVP structure of the present invention, FIG. 2 is a schematic structural diagram of a substituted olefin in which one monomer contains both catechol and double bond structures, several typical monomers are shown in FIG. 3, and the boxes on the structural formula of each monomer are R with different structures.
Example 1:11.1g (0.1 mol) of commercially available NVP monomer with a purity of 99% is dissolved in 20mL of pure water, 1.5g (0.01 mol) of 4-allylcatechol is added, the mixture is stirred and dissolved uniformly, 0.1mL of 30% hydrogen peroxide is added, the temperature is gradually raised to 50 +/-5 ℃ for reaction for 4 hours, and the system gradually becomes viscous. Putting the system into a dialysis bag with molecular weight cutoff of 3500, dialyzing with pure water for 24 hours, changing water for many times during the dialysis to remove residual micromolecules, and freeze-drying to obtain white solid. The total molecular weight of the finished product is about 80 ten thousand, wherein the NVP ratio is about 90%.
The white solid polymer is dissolved in 95% ethanol solution according to the concentration of 5%, 0.2% Tego Flow 370 flatting agent and 0.05% antioxidant 1010 are added, and the mixture is stirred and dissolved uniformly. The nylon catheter is immersed in the solution for 1 minute, taken out and aired until no obvious surface solvent is visible, and then suspended in an oven at 50 +/-5 ℃ for heat preservation for 1 hour to obtain the catheter coated with the hydrophilic solution coating. The catheter had no visible coating on it, and the friction was checked in the dry state, similar to uncoated catheters, with no significant difference. The frictional force was measured at about 150gf under a load of 1Kg on a frictional force tester, as shown in FIG. 4.
The coated catheter described above was immersed in water for 30 seconds, taken out to measure the frictional force, and it was found that the frictional force had been reduced to 0.3gf, showing a remarkable lubricating property. Repeated friction testing with a friction tester, the friction force on the catheter surface was observed to increase gradually at the later stages, but before that, the catheter exhibited significant low friction, high lubricity characteristics and was able to sustain a friction force below 5gf after 40 cycles of reciprocation (fig. 5).
Example 2: similar to example 1, but using 3, 4-dihydroxyphenethylacrylate in an amount of 1g (5 mmol), the polymerization gave a similar white solid powder of example 1 having a molecular weight of about 100 million with NVP in the ratio of about 95%. Dissolved in 85% isopropyl alcohol at a concentration of 3% to form a solution, which is applied to the catheter, and the measured frictional force after water absorption may be below 1gf after 40 cycles of reciprocal rubbing (as shown in fig. 6).
Example 3: similar to example 1, but using dopamine methacrylamide in an amount of 1g (5 mmol) as the second monomer, a white solid powder similar to example 1 was obtained after polymerization, having a molecular weight of about 80 ten thousand and a NVP content of about 95%. Can be dissolved in ethanol-water mixed solvent, prepared into 4% solution, coated on catheter, and dried to obtain coating with 1Kg weight friction force lower than 2gf after absorbing water.
Comparative example 1: as a comparative example, using commercially available PVP having a molecular weight of 130 ten thousand dissolved at a concentration of 5% in 90% isopropyl alcohol solution, 0.2% Tego Flow 370 leveling agent and 0.05% antioxidant 1010 were added, dissolved uniformly with stirring, coated on a catheter, and after absorption the friction was measured to be lower than 2gf at the initial stage, but after 6 cycles the friction had risen to about 100gf, and after about 20 cycles the friction had recovered to about 150gf.
The above embodiments are merely illustrative of the technical concept and features of the present invention, and the purpose thereof is to enable those skilled in the art to understand the content of the present invention and implement the invention, and not to limit the scope of the invention, and all equivalent changes or modifications made according to the spirit of the present invention should be covered by the scope of the present invention.
Claims (15)
1. A copolymer containing an NVP structure is characterized by being formed by copolymerizing two monomers, wherein one monomer is NVP, and the other monomer is substituted olefin of which the structure simultaneously contains catechol and a double-bond structure.
2. The NVP structure-containing copolymer according to claim 1, characterized by having a structure represented by the general formula (i):
wherein R is an alkyl group, an ester group or an amide group;
m/（m+n）>0.5；
the molecular weight of the copolymer is between 1000 and 200 ten thousand.
3. The copolymer containing NVP structure of claim 2, wherein the copolymer has a molecular weight of 5 to 150 ten thousand.
4. The NVP structure-containing copolymer according to claim 2, characterized in that the copolymer has a molecular weight of 60 to 150 ten thousand.
5. A copolymer containing NVP structures according to claim 2, characterized in that m/(m + n) >0.8.
6. The NVP structure-containing copolymer according to claim 1, characterized in that R is a methylene group, an acetyl ester group or an acetamide group.
7. Use of the NVP structure-containing copolymer of any one of claims 1 to 6 in a lubricious coating for an interventional catheter.
8. A lubricious coating mixture for an interventional catheter comprising the NVP structure-containing copolymer of any of claims 1-6, and a solvent.
9. The lubricious coating mixture for interventional catheters as defined in claim 8, wherein the mass-to-volume concentration of the copolymer containing NVP structures is 1-20%.
10. The lubricious coating mixture for interventional catheters as defined in claim 8, wherein the solvent is water or a mixture of water and an alcohol solvent.
11. The lubricious coating mixture for interventional catheters as defined in claim 8, further comprising a leveling agent and a stabilizer, wherein the sum of the mass concentrations of the leveling agent and the stabilizer is not more than 1%.
12. An interventional catheter, characterized in that its surface is provided with a coating of a lubricious coating mixture for interventional catheters as claimed in any of claims 8-11.
13. The interventional catheter of claim 12, wherein the surface coating is formed by applying a lubricious coating mixture for the interventional catheter and drying to remove the solvent.
14. The interventional catheter of claim 13, wherein the coating has a thickness of 1-50 μm.
15. The interventional catheter of claim 13, wherein the coating has a thickness of 5-20 μm.
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