CN113733532B - Flexible polyester patch and preparation method and application thereof - Google Patents
Flexible polyester patch and preparation method and application thereof Download PDFInfo
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- CN113733532B CN113733532B CN202110991591.3A CN202110991591A CN113733532B CN 113733532 B CN113733532 B CN 113733532B CN 202110991591 A CN202110991591 A CN 202110991591A CN 113733532 B CN113733532 B CN 113733532B
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C53/00—Shaping by bending, folding, twisting, straightening or flattening; Apparatus therefor
- B29C53/56—Winding and joining, e.g. winding spirally
- B29C53/58—Winding and joining, e.g. winding spirally helically
- B29C53/78—Winding and joining, e.g. winding spirally helically using profiled sheets or strips
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C53/00—Shaping by bending, folding, twisting, straightening or flattening; Apparatus therefor
- B29C53/02—Bending or folding
- B29C53/08—Bending or folding of tubes or other profiled members
- B29C53/086—Bending or folding of tubes or other profiled members bending radially, i.e. deformig the cross-section of the tube
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/664—Polyesters containing oxygen in the form of ether groups derived from hydroxy carboxylic acids
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29L—INDEXING SCHEME ASSOCIATED WITH SUBCLASS B29C, RELATING TO PARTICULAR ARTICLES
- B29L2031/00—Other particular articles
- B29L2031/753—Medical equipment; Accessories therefor
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- Mechanical Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Materials For Medical Uses (AREA)
Abstract
The invention discloses a flexible polyester patch and a preparation method and application thereof, and relates to the technical field of medicine. The invention relates to a preparation method of a flexible polyester patch, which comprises the following steps: (1) Cutting the PCT film, wrapping the PCT film on a circular tubular mold, heating for a period of time, and cooling to obtain a circular tubular patch; (2) And (2) heating the circular tubular patch prepared in the step (1) for a period of time, and then applying external force to knead the circular tubular patch flat to obtain a temporary-shaped patch, thereby obtaining the flexible polyester patch. The flexible polyester patch sheet prepared by the invention has good flexibility, can be well attached to the inner wall of a blood vessel through the shape memory performance of the flexible polyester patch sheet, and is not easy to damage the inner wall of the blood vessel in the transplanting process. Compared with the vascular stent, the flexible polyester patch provided by the invention is thin in thickness, easy to degrade and free from remaining in blood vessels to form new blockage.
Description
Technical Field
The invention relates to the technical field of medicine, in particular to a flexible polyester patch and a preparation method and application thereof.
Background
Ischemic diseases such as thromboembolism are important factors causing death of the global population every year. The main causes of blood embolism are atherosclerosis caused by the pathological changes of blood vessel walls and the reduction of the inner diameter of the blood vessel. Red blood cells, fibrinogen and platelets in blood tend to adhere to the affected part, so that blood vessels are obviously narrowed or even blocked. Which in turn causes a reduction in local blood flow or interruption of blood supply, which if not treated in a timely manner, can lead to death.
At present, two methods are mainly used for treating the blood embolism, one method is to implant a vascular stent at the position of the stenotic blockage of a blood vessel, and the stenotic blockage of the blood vessel is propped open by using the higher elastic modulus and strength of the vascular stent, so that the blood vessel is unblocked again, and normal blood supply is realized. However, the method has the problems that after the stent is implanted, the normal flow of blood is ensured, but because the embolus is not taken out, and if the implanted vascular stent can not be degraded in time, endothelial cells can grow into the stent to form new vascular endothelial tissues, and the stent which can not be degraded in time can become a new obstruction, so that secondary blockage is caused. According to statistics, the restenosis rate of the blood vessel of the patient after the implantation of the blood vessel stent reaches 15 to 20 percent. Another method is to take out the embolus blocking the blood vessel outside the body by mechanical method with an embolectomy device. Most of the blockage can be cleared away by the method, but the method does not repair the hardened blood vessel. In addition, the method has large damage to the vessel wall, and is easy to cause secondary damage to the vessel.
In order to ensure normal contraction and expansion of the blood vessel after operation and maintain normal blood supply, the breaking elongation of the vascular graft is more than 60%. Meanwhile, the healing period of vascular repair is about 6 months, and in order to avoid secondary blockage, the vascular graft needs to be degradable, and the degradation period of the vascular graft should be identical with the healing period of vascular repair. The current common in vivo transplantation stents such as polytetrafluoroethylene, polyamide and the like cannot meet the requirement.
Disclosure of Invention
Based on the above, the invention aims to overcome the defects of the prior art and provide a flexible polyester patch and a preparation method and application thereof.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows: a preparation method of a flexible polyester patch comprises the following steps:
(1) Cutting the PCT film, wrapping the PCT film on a circular tubular mold, heating for a period of time, and cooling to obtain a circular tubular patch;
(2) And (2) heating the round tubular patch prepared in the step (1) for a period of time, and then applying external force to knead the patch flat to obtain a temporary-shaped patch, thus obtaining the flexible polyester patch.
The invention provides a preparation method of a flexible polyester patch, which mainly adopts a mode of heating and cooling twice, better exerts the effect of the flexible polyester patch and achieves a good effect of being attached to blood vessels. The first heating is to soften the PCT film, and the PCT film is cooled to obtain a permanent memory shape; the second heating is to prepare a temporary patch with a small cross section area and a small volume, namely the flexible polyester patch, so that minimally invasive implantation is realized, and the patch is restored to be in a circular tube shape and attached to the inner wall of the blood vessel under the condition of human body temperature after being implanted into a body.
Preferably, in the step (1), the PCT film is prepared as follows:
(a) Purifying and drying 4- (ethylene glycol ketal) -epsilon-caprolactone and epsilon-caprolactone containing side cyclic ether, weighing a certain content of 4- (ethylene glycol ketal) -epsilon-caprolactone and epsilon-caprolactone containing side cyclic ether, adding stannous octoate, a toluene solution and benzyl alcohol, stirring uniformly, reacting under vacuum to obtain a mixed solution A, and sealing a reaction container after no bubbles are generated for 30 min;
(b) Stirring the sealed reaction container in an oil bath at 130 ℃ for 24 hours for reaction, purifying after the reaction is finished, and drying to constant weight to obtain a PCT sample;
(c) And adding methylene dichloride to the PCT sample to dissolve the PCT sample, placing the PCT sample in a mould, and air-drying to obtain the PCT film.
The preparation method of the PCT film is prepared according to the method in the literature, namely design synthesis of the elastic polycaprolactone based on side cyclic ether modification and application research of the elastic polycaprolactone in soft tissue engineering.
Preferably, in the step (1), the thickness of the PCT film is 0.05-0.2mm, and the outer diameter of the round tubular mould is 2-8mm. The thickness of the circular tube patch is flexibly selected according to different use scenes, and a proper circular tube-shaped die is selected according to the outer diameter of a blood vessel which is hardened or blocked.
Preferably, in the step (1), the heating temperature is 46-56 ℃, and the heating time is 5-15s; cooling to 20-25 deg.C. The heating temperature of the invention is 46-56 ℃, and after a large number of creative tests of the inventor, the invention finds that the PCT film has better softening effect and is easier to shape in the temperature range, and a permanent circular tube-shaped patch is easier to obtain after cooling.
Preferably, in the step (2), the heating temperature is 32-36 ℃, and the heating time is 1-2min. The heating temperature of the invention is 32-36 ℃, and after a great deal of creative experiments of the inventor, the inventor finds that in the temperature range, the molecular chain part moves, and the temporary shape patch is easier to obtain by applying external force to pinch and flatten, and the shape of the permanent circular tube patch after heating recovery can not be changed too much.
In addition, the invention provides the flexible polyester patch prepared by the preparation method of the flexible polyester patch. Furthermore, the invention provides application of the flexible polyester patch in preparing an antithrombotic patch.
Compared with the prior art, the invention has the beneficial effects that: the invention provides a flexible polyester patch, and the degradability and the shape memory performance of the flexible polyester patch can be better exerted through the preparation method of the flexible polyester patch. The flexible polyester patch sheet prepared by the invention has good flexibility, can be well attached to the inner wall of a blood vessel through the shape memory performance of the flexible polyester patch sheet, and is not easy to damage the inner wall of the blood vessel in the transplanting process. Compared with the vascular stent, the flexible polyester patch provided by the invention is thin in thickness, easy to degrade and free from remaining in blood vessels to form new blockage.
Drawings
FIG. 1 is a diagram of the preparation process and application of a flexible polyester patch;
figure 2 is a schematic illustration of the implantation application and degradation of a flexible polyester patch.
Detailed Description
To better illustrate the objects, aspects and advantages of the present invention, the present invention will be further described with reference to the accompanying drawings and specific embodiments.
The PCT film used in the embodiment of the invention is prepared according to a method in a literature, namely design synthesis of elastic polycaprolactone based on side cyclic ether modification and application research of elastic polycaprolactone in soft tissue engineering, wherein the mass ratio of CL to TOSUO is 85:15, linear PCT;
the preparation method comprises the following steps:
(a) Purifying and drying 4- (ethylene glycol ketal) -epsilon-caprolactone and epsilon-caprolactone containing side cyclic ether, weighing a certain content of 4- (ethylene glycol ketal) -epsilon-caprolactone and epsilon-caprolactone containing side cyclic ether, adding stannous octoate, a toluene solution and benzyl alcohol, stirring uniformly, reacting under vacuum to obtain a mixed solution A, and sealing a reaction container after no bubbles are generated for 30 min;
(b) Stirring the sealed reaction container in an oil bath at 130 ℃ for 24 hours for reaction, purifying after the reaction is finished, and drying to constant weight to obtain a PCT sample;
(c) 1.5g of PCT sample is put into a rectangular mould of 90X 90mm, 20mL of dichloromethane is added for dissolution, and the mixture is placed in a fume hood for 24 hours, and after the solvent is volatilized, a PCT film with the thickness of 0.18mm can be obtained.
The invention provides embodiments 1-3, and the preparation method of the flexible polyester patch of the embodiments 1-3 is as follows, and the preparation flow is shown in fig. 1:
example 1
A preparation method of a flexible polyester patch comprises the following steps:
(1) Cutting a PCT film, wrapping the PCT film on a round tubular mold, heating for a period of time, cooling, wherein the outer diameter of the round tubular mold is 2mm, the heating temperature is 46 ℃, and the heating time is 15s; cooling to 20 ℃ to obtain a circular tube-shaped patch;
(2) And (2) heating the circular-tube-shaped patch prepared in the step (1) for a period of time, wherein the heating temperature is 32 ℃, the heating time is 1min, and applying external force to pinch the patch to obtain a temporary-shaped patch so as to obtain the flexible polyester patch.
Example 2
A preparation method of a flexible polyester patch comprises the following steps:
(1) Cutting a PCT film, wrapping the PCT film on a round tubular mold, heating for a period of time, cooling, wherein the outer diameter of the round tubular mold is 8mm, the heating temperature is 56 ℃, and the heating time is 5s; cooling to 25 ℃ to obtain a circular tube-shaped patch;
(2) And (2) heating the circular-tube-shaped patch prepared in the step (1) for a period of time, wherein the heating temperature is 36 ℃, the heating time is 2min, and applying external force to pinch the patch to obtain a temporary-shaped patch so as to obtain the flexible polyester patch.
Example 3
A preparation method of a flexible polyester patch comprises the following steps:
(1) Cutting a PCT film, wrapping the PCT film on a circular tubular mould, heating for a period of time at 50 ℃ for 10s, wherein the outer diameter of the circular tubular mould is 5mm, and cooling the PCT film after heating for a period of time; cooling to 25 ℃ to obtain a circular tube-shaped patch;
(2) And (2) heating the round tubular patch prepared in the step (1) for a period of time, wherein the heating temperature is 34 ℃, the heating time is 2min, and applying external force to knead the patch flat to obtain a temporary-shaped patch so as to obtain the flexible polyester patch.
Meanwhile, the invention is provided with comparative examples 1-4, and the preparation method of the flexible polyester patch specifically comprises the following steps:
comparative example 1
A preparation method of a flexible polyester patch comprises the following steps:
(1) Cutting a PCT film, wrapping the PCT film on a round tubular mold, heating for a period of time, cooling, wherein the outer diameter of the round tubular mold is 5mm, the heating temperature is 60 ℃, and the heating time is 10s; cooling to 25 ℃ to obtain a circular tube-shaped patch;
(2) And (2) heating the round tubular patch prepared in the step (1) for a period of time, wherein the heating temperature is 34 ℃, the heating time is 2min, and applying external force to knead the patch flat to obtain a temporary-shaped patch so as to obtain the flexible polyester patch.
Comparative example 2
A preparation method of a flexible polyester patch comprises the following steps:
(1) Cutting a PCT film, wrapping the PCT film on a round tubular mold, heating for a period of time, cooling, wherein the outer diameter of the round tubular mold is 5mm, the heating temperature is 40 ℃, and the heating time is 10s; cooling to 25 ℃ to obtain a circular tube-shaped patch;
(2) And (2) heating the circular-tube-shaped patch prepared in the step (1) for a period of time, wherein the heating temperature is 34 ℃, the heating time is 2min, and applying external force to pinch the patch to obtain a temporary-shaped patch so as to obtain the flexible polyester patch.
Comparative example 3
A preparation method of a flexible polyester patch comprises the following steps:
(1) Cutting a PCT film, wrapping the PCT film on a round tubular mold, heating for a period of time, cooling, wherein the outer diameter of the round tubular mold is 5mm, the heating temperature is 50 ℃, and the heating time is 10s; cooling to 25 ℃ to obtain a circular tube-shaped patch;
(2) And (2) heating the round tubular patch prepared in the step (1) for a period of time, wherein the heating temperature is 30 ℃, the heating time is 2min, and applying external force to knead the patch flat to obtain a temporary-shaped patch so as to obtain the flexible polyester patch.
Comparative example 4
A preparation method of a flexible polyester patch comprises the following steps:
(1) Cutting a PCT film, wrapping the PCT film on a round tubular mold, heating for a period of time, cooling, wherein the outer diameter of the round tubular mold is 5mm, the heating temperature is 50 ℃, and the heating time is 10s; cooling to 25 ℃ to obtain a circular tube-shaped patch;
(2) And (2) heating the round tubular patch prepared in the step (1) for a period of time, wherein the heating temperature is 42 ℃, the heating time is 2min, and applying external force to knead the patch flat to obtain a temporary-shaped patch so as to obtain the flexible polyester patch.
The preparation methods and application diagrams of the flexible polyester patches of the embodiments and the comparative examples are shown in fig. 1, the flexible polyester patches of the embodiments 1 to 3 are good in flexibility, can be well attached to the inner wall of a blood vessel through the shape memory performance of the flexible polyester patches, and are not easy to damage the inner wall of the blood vessel in the transplanting process. Compared with the vascular stent, the flexible polyester patch prepared in the embodiment 1-3 of the invention has the advantages of thin thickness, easy degradation and no residue in blood vessels to form new blockage.
The heating temperature in the step (1) in the comparative example 1 is 60 ℃, and if the heating is carried out at 60 ℃, because the temperature is far higher than the melting temperature of the material (Tg =44.3 ℃), the whole molecular chain can move without limitation, so that the film is directly melted into a mass during heating, and a round pipe with a permanent shape cannot be obtained; in the comparative example 2, the heating temperature in the step (1) is 40 ℃, when the heating temperature is 40 ℃, the movement degree of molecular chains is small, and the film is difficult to close to form a circular tubular patch; in comparative example 3, the heating temperature in step (2) was 34 ℃, most of the crystals were not melted during the secondary heating and remained crystalline, resulting in fewer rearranged polymer chains, difficulty in fixing the shape, and difficulty in obtaining a patch with a temporary shape; in comparative example 4, step (2) was heated at 42 ℃ and most of the crystals were melted and more polymer chains were released to be rearranged. The molecular chains for memorizing the permanent shape are few, the driving force for shape recovery is small, and the permanent shape is difficult to recover, so that the fitting degree is low.
Test example 1 test for degree of adhesion
The test process comprises the following steps: in the preparation of the flexible polyester patch of examples 1-3, the cross-sectional area S1 of the tubular patch obtained in step (1) was recorded; the cross-sectional area S2 of the temporary patch obtained in the step (2); keeping the temporary patch (namely the flexible polyester patch) at 37-40 ℃ for a period of time to obtain a recovered flexible polyester patch, wherein the cross sectional area is marked as S3;
example 1-3 preparation method of flexible polyester patch, in the actual test process, 3 sets of tests were performed respectively;
the test formula is as follows: shape recovery rate Rr = (S3-S2)/(S1-S2);
and (3) test results: as described in table 1 below;
table 1 results of the adhesion test
In the practical application process of the flexible polyester patch, the shape recovery rate can reach more than 85 percent.
Finally, it should be noted that the above embodiments are only used for illustrating the technical solutions of the present invention and not for limiting the protection scope of the present invention, and although the present invention is described in detail with reference to the preferred embodiments, it should be understood by those skilled in the art that modifications or equivalent substitutions can be made on the technical solutions of the present invention without departing from the spirit and scope of the technical solutions of the present invention.
Claims (4)
1. A preparation method of the flexible polyester patch is characterized by comprising the following steps:
(1) Cutting the PCT film, wrapping the PCT film on a circular tubular mold, heating for a period of time, and cooling to obtain a circular tubular patch;
(2) Heating the round tubular patch prepared in the step (1) for a period of time, and then applying external force to knead the patch flat to obtain a temporary-shaped patch so as to obtain the flexible polyester patch;
in the step (1), the heating temperature is 46-56 ℃, and the heating time is 5-15s; cooling to 20-25 deg.C;
in the step (2), the heating temperature is 32-36 ℃, and the heating time is 1-2min;
in the step (1), the preparation method of the PCT film is as follows:
(a) Purifying and drying 4- (ethylene glycol ketal) -epsilon-caprolactone and epsilon-caprolactone containing side cyclic ether, weighing a certain content of 4- (ethylene glycol ketal) -epsilon-caprolactone and epsilon-caprolactone containing side cyclic ether, adding stannous octoate, a toluene solution and benzyl alcohol, stirring uniformly, reacting under vacuum to obtain a mixed solution A, and sealing a reaction container after no bubbles are generated for 30 min;
(b) Stirring the sealed reaction container in an oil bath at 130 ℃ for 24 hours for reaction, purifying after the reaction is finished, and drying to constant weight to obtain a PCT sample;
(c) And adding methylene dichloride to the PCT sample to dissolve the PCT sample, placing the PCT sample in a mould, and air-drying to obtain the PCT film.
2. The method for preparing a flexible polyester patch according to claim 1, wherein in the step (1), the thickness of the PCT film is 0.05 to 0.2mm, and the outer diameter of the circular tubular mold is 2 to 8mm.
3. A flexible polyester patch prepared by the method of any one of claims 1-2.
4. Use of the flexible polyester patch of claim 3 in the manufacture of an anti-thrombotic patch.
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