CN115558078A - Degradable polyurethane and application thereof - Google Patents
Degradable polyurethane and application thereof Download PDFInfo
- Publication number
- CN115558078A CN115558078A CN202211212033.3A CN202211212033A CN115558078A CN 115558078 A CN115558078 A CN 115558078A CN 202211212033 A CN202211212033 A CN 202211212033A CN 115558078 A CN115558078 A CN 115558078A
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- CN
- China
- Prior art keywords
- degradable polyurethane
- ethyl ester
- methyl
- degradable
- polyurethane
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Abstract
The invention discloses degradable polyurethane and application thereof, the degradable polyurethane improves the processability and biocompatibility of materials by a specific proportion of structures and grafting specific compounds, the materials are coated on the surface of medical products or independently processed into medical device products, and the degradable polyurethane has wide application prospect in the field of plant intervention medical devices.
Description
Technical Field
The invention belongs to the field of degradable biological materials, and particularly relates to degradable polyurethane and application thereof.
Background
Polyurethane (PU) is a general name for macromolecular compounds having a urethane (-NHC 00-) group in the main chain, and is entirely known as polyurethane. It is prepared by the polyaddition of organic diisocyanate or polyisocyanate and dihydroxy or polyhydroxy compound. The typical PU chemical structure shows that the polymer backbone is composed of blocks of soft segments (soft segments) with a glass transition temperature below room temperature and hard segments (hard segments) with a glass transition temperature above room temperature. Generally, polyether or polyester diols are used for synthesis to form soft segments of polymers, which have low glass transition temperature and weak polarity, and which constitute the continuous phase of the material, impart elasticity to PU and control the low temperature resistance, solvent resistance, weather resistance, etc. of PU; the chain segment generated by the reaction of the diisocyanate and the chain extender is a hard segment, the generally formed hard segment chain has high glass transition temperature and strong polarity, and a large amount of hydrogen bonds are formed among molecular chains due to-CO-NH-functional groups in the hard segment, so that the interaction force is strong, the molecular chains exist in a crystalline state, and the properties of the PU such as strength, heat resistance and the like are controlled. The difference in polarity between the hard and soft segments of PU and the crystallization of the hard segment itself cause them to be thermodynamically incompatible and to have a tendency to spontaneously separate, so that the hard segments are easily aggregated to form domains dispersed in the continuous phase formed by the soft segments to form a microphase-separated structure. The advantage of this material is that the properties of PU, such as elasticity, modulus, strength, elongation at break, wear resistance, lubricity, hydrophilicity and hydrophobicity, biocompatibility and biostability, etc., can be changed in a wide range by designing the structure, length and distribution, relative proportion and relative molecular mass of different soft and hard segments.
Based on a specific microphase separation structure of degradable polyurethane, the degradable polyurethane is processed into medical products such as a micro-nano fiber membrane, a microsphere or a coating, the surface structure of the degradable polyurethane is similar to that of a biological membrane, and a plurality of literature researches at home and abroad report that the polyurethane material has the characteristics of good mechanical property, biocompatibility, blood compatibility, easy processing and the like, and the degradable polyurethane is a very promising degradable medical material in the fields of drug sustained release carriers, medical surgical materials, tissue engineering scaffolds and the like.
Many documents both at home and abroad disclose the scheme of preparing degradable polyurethane, such as polyurethane synthesized by using 1, 6-Hexamethylene Diisocyanate (HDI) as a hard segment, polycarbonate diol (PCDL) as a soft segment and lysine ethyl ester hydrochloride (Lys-OEt) as a chain extender; taking L-lysine as a raw material, converting carboxyl on the L-lysine into ester groups, and synthesizing polyurethane obtained by copolymerizing L-lysine (ethyl ester/methyl ester) diisocyanate (LDI) with polyethylene glycol (PEG) or p-hydroxyethyl piperazine (HEP) with different molecular weights respectively under the action of a catalyst; poly (epsilon-caprolactone) diol (PCL) with molecular weight of 2000 reacts with LDI to generate prepolymer, and then reacts with chain extender 1, 4-Butanediol (BDO) to synthesize Polyurethane (PU) and the like, wherein the degradable polyurethane material with the basic structure of polycaprolactone polyurethane taking LDI as a hard end is regarded as the most promising industrial transformation material in materials implanted into human bodies by researchers in the field, and the improvement of the processing performance and the biocompatibility of the material by further optimizing the structure of the material is the direction of the research of the researchers in the field.
The present inventors have conducted synthetic research and improvement based on the chemical structure since 2015 to date, such as (cn201610762899. X) a tissue-inducible biomedical material and (CN 201610188084.5) a long-acting subcutaneous implant and a preparation method thereof, and the biocompatibility of the synthesized degradable polyurethane material needs to be further optimized. In order to further improve the processing performance and biocompatibility of the material, the medical degradable polyurethane with controllable degradation time and adjustable elongation at break (CN 201710971002.9) is designed and developed in 2017, the medical degradable polyurethane with antibacterial activity (CN 201811263478.8) is synthesized in 2018, and the degradable polyurethane with the novel structure is obtained through a series of experimental researches and experimental screening for many years.
Disclosure of Invention
The invention aims to solve the technical problem of providing degradable polyurethane and application thereof, wherein the degradable polyurethane material with better processing performance and biocompatibility can be obtained by accurately regulating and controlling the proportion of each component in the polyurethane structure and grafting a D compound, and can be applied to different products for plant intervention in various medical or plastic cosmetology of human bodies.
In order to solve the above technical problems, an embodiment of the present invention provides a degradable polyurethane, where the degradable polyurethane has a structure containing an implant material and a compound D, and the structural formula of the degradable polyurethane is as shown in formula:
The chemical structure of the compound D is as shown in the formula
Shown in the specification:
Formula (II)
The method comprises the following steps:
LDI is L-lysine (ethyl ester/methyl ester) diisocyanate, CL is caprolactone open ring, and the chemical bond between LDI and CL is a carbamate bond;
a: one selected from polyethylene glycol (200-1000) and small molecular diol monomer;
c: is a chain extender and is selected from one or two of compounds with two hydroxyl groups, two amino groups or as shown in E;
m, n and p are numbers 2-100;
is of the formula
The method comprises the following steps:
r: one selected from H, ethyl ester and methyl ester.
The degradable polyurethane comprises the following components in percentage by weight:
A：0.5%~15%
CL：50%~80%
LDI：5%~50%
C：0.5%~5%
D：0.01%~5%。
the degradable polyurethane can also comprise the following components in percentage by weight:
A：0.5%~15%
CL：50%~80%
LDI：5%~50%
C：0.5%~5%
D：0.01%~5%
E：0.01%~5%
wherein E is a compound obtained by reacting 2 molecules of chain extender and 1 molecule of LDI or 1 or more repeating units of the compound.
The degradable polyurethane can also comprise the following components in percentage by weight: :
A：0.5%~10%
CL：50%~80%
LDI：5%~50%
C：0.5%~5%
D：0.01%~5%
E：0.01%~5%
wherein, the percentage content of E in C is 20% -100%.
Among them, the numbers of m, n, and p are more preferably:
m：5~50
n：5~50
P：5~50。
wherein, the degradable polyurethane contains trace (the percentage content in the material is less than two ten-thousandths) of catalyst, in particular one or two combinations of nontoxic organic metal catalysts;
c is selected from one or more of ethylene glycol, propylene glycol, butanediol, pentanediol, butanediamine, pentanediamine, diamine-like, hydroxyprogenic acid (methyl ester/ethyl ester), arginine (methyl ester/ethyl ester), cysteine (methyl ester/ethyl ester), cystine (methyl ester/ethyl ester), serine (methyl ester/ethyl ester), glutamic acid (methyl ester/ethyl ester), threonine (methyl ester/ethyl ester), aspartic acid (methyl ester/ethyl ester), tyrosine (methyl ester/ethyl ester), lysine (methyl ester/ethyl ester) and arginine (methyl ester/ethyl ester).
The invention also provides an application of the degradable polyurethane, which comprises the following applications:
(1) Preparing a tissue repair membrane material by an electrostatic spinning technology;
(2) Preparing soft tissue filling material by microsphere preparation technology;
(3) The titanium alloy is used as a coating material of medical appliance products implanted into the body, and is coated on titanium alloy non-degradable implanted metal materials or degradable metal materials through dip coating and spraying technologies so as to improve the biocompatibility of implanted appliances.
Wherein, the application of the degradable polyurethane also comprises:
(4) Preparing tissue filling materials with different shapes by a 3D printing technology;
(5) The wire or the covered wire is prepared by a melt extrusion drawing technique.
The degradable polyurethane can be used as follows: materials made from degradable polyurethanes are used in medical and cosmetic products, including but not limited to, soft tissue regeneration repair, including: peripheral nerve repair sleeve, peripheral nerve repair covering film, peripheral nerve repair protection sheet, artificial skin, biodegradable coating, operation anti-adhesion film, craniocerebral membrane, cartilage repair bracket, bone filling material, meniscus repair porous plate, spinal fibrous ring, wound repair film and dressing, elastic absorbable operation suture, hernia repair patch, soft tissue lifting belt (thread) and the like.
The use of degradable polyammonia may further comprise: adding polypeptide, collagen, protein and active ingredient which are commercially available or already disclosed into degradable polyurethane, and preparing into medicine with antiproliferative, anti-migration, anti-angiogenesis, anti-inflammation, cell growth inhibition, cytotoxicity or physiological activity added according to treatment requirement.
Compared with the prior art, the invention has the beneficial effects that:
1. the polycaprolactone type polyurethane with LDI as a hard end is further optimized and improved to be a basic structure, and when the weight percentage of E in C is screened out through experiments to be more than 20%, the softening point of the obtained material is improved, the elastic modulus is increased, and the processing performance is better.
2. Compared with the traditional glycol-terminated material, the material of the grafted D compound has smaller contact angle, better hydrophilicity, higher speed of inducing the growth of fibroblasts than the material terminated by glycol and better biocompatibility.
Description of the drawings:
FIG. 1 is an infrared spectrum of a hydroxyl terminated polyurethane structure;
FIG. 2 is an infrared spectrum of a polyurethane blocked with compound D;
FIG. 3 is a schematic diagram showing contact angles of components in degradable polyurethane;
fig. 4 is a culture picture of fibroblasts on a micro-nanofiber membrane.
The specific implementation mode is as follows:
while the present invention has been described with reference to specific examples, it will be understood by those skilled in the art that these examples are intended in an illustrative manner and are not intended to limit the scope of the invention.
The degradable polyurethane with good processing performance and biocompatibility provided by the invention is realized by the following steps:
the main structural formula of the degradable polyurethane grafted with the D compound is as follows:
wherein, the chemical structure of the compound D is as follows:
the free amino group of the compound D reacts with LDI and is connected through carbamido;
LDI is L-lysine (ethyl ester/methyl ester) diisocyanate, CL is a caprolactone ring-opening structure, and a chemical bond between LDI and CL is a carbamate bond;
wherein:
a: one selected from polyethylene glycol (200-1000), small molecule diol (ethylene glycol, 1,3 propylene glycol, 1.4 butylene glycol and 1, 5-pentanediol);
c: is a chain extender and is selected from one or two of compounds with two hydroxyl groups, two amino groups or as shown in E;
r: one selected from H, ethyl ester and methyl ester;
m, n and p are numbers 2-100.
Preferably, the weight ratio of each component is as follows:
A：0.5%~15%
CL：50%~80%
LDI：5%~50%
C：0.5%~5%
D：0.01%~5%。
further, the weight ratio of each component is as follows:
A：0.5%~15%
CL：50%~80%
LDI：5%~50%
C：0.5%~5%
D：0.01%~5%
E：0.1%~5%。
wherein E: selected from the group consisting of a compound obtained by reacting two molecules of chain extender with 1 molecule of LDI or 2 or more repeating units of the compound;
the weight ratio of each component can also be as follows:
A：0.5%~15%
CL：50%~80%
LDI：10%~50%
C：0.5%~5%
D：0.1%~5%
E：0.1%~5%
wherein the percentage content of E in C is 20% -100%.
The numbers of m, n, p are more preferably:
m：5~50
n：5~50
P：5~50。
c is a chain extender: the specific structure is selected according to the requirement of applying the material in different medical products to induce tissue regeneration, wherein the diamine is selected from two molecules of amino acid (one of 20 common amino acids) and a compound synthesized by an ester bond of one molecule of ethylene glycol or 1,3 propylene glycol through an esterification reaction, such as: the compound which is obtained by esterification reaction of two molecules of phenylalanine and one molecule of 1 and 3 propanediol and is connected by two ester bonds and has two active amino groups is as follows:
the structure of E: 2 molecules of diol and 1 molecule of LDI are in a structure or a plurality of repeating units obtained by urethane bond, and the structural formula is shown as the following figure:
wherein q is a number between 1 and 10, and within the range of 1< -q < -6, the synthesized material has excellent processability.
As some byproducts are inevitably generated in the reaction process of the high polymer material, the degradable polyurethane has the following main structure:
the content of the compound of the structure in the material is more than 80 percent.
The degradable polyurethane with good processing performance and biocompatibility is prepared by adding a small amount of catalysts (0.01-0.03 wt% of the total amount) such as organotin and organobismuth, preferably catalysts with low toxicity, such as: stannous octoate, dibutyltin diacetate, dibutyltin dilaurate, MB20 and DY-20 or a combination of two of the above.
Wherein the implantable medical product further comprises a contrast agent selected from the group consisting of: radiocontrast agents (positive and negative contrast agents) and the like are commonly used, usually also in ionic form in bound or complexed form of zirconium, barium, iodine, manganese, iron, lanthanum, cerium, praseodymium, etc., preferably a barium or iodine containing contrast agent, more preferably one of zirconium dioxide, barium sulfate and iodine preparations.
The organic solvent in the preparation method is selected from one or more of DMF, DMSO, tetrahydrofuran, ethanol, isopropanol, n-butanol, acetone, butanone, cyclohexanone, isoamyl acetate, ethyl acetate, dichloromethane, chloroform, 1, 4-dioxane or hexafluoroisopropanol.
The invention aims to develop degradable polyurethane with good processability and biocompatibility and application thereof.
One of the applications is as follows:
the titanium alloy biodegradable implant film can be made into a tissue repair film material by an electrostatic spinning technology, can also be made into a soft tissue filling material by a microsphere preparation technology, can also be used as a coating material of a medical appliance product implanted into a body, can be coated on a titanium alloy non-degradable implant metal material and can also be coated on a degradable metal material, and therefore, the biocompatibility of the implant appliance is improved.
The second application is as follows: preparation of 3D printed or melt extruded stretched materials
The tissue filling material with different shapes can be prepared by 3D printing, and the wire rod can also be prepared by a melt extrusion stretching technology.
The third application is as follows: the film, the ball, the line, the coating and the 3D printing material are applied to medical and plastic beauty products, and the specific application comprises the following steps: the device comprises a nerve repair sleeve, a nerve repair coating film, a nerve repair protection sheet, a biodegradable coating cartilage repair bracket, an implant device, an implantable artificial organ, a contact artificial organ, a bracket, an interventional catheter and an organ auxiliary device, and specifically comprises a bone plate, a bone nail, a bone needle, a bone rod, a bone filling material, a spinal internal fixing material, a ligature wire, a patellar concentrator, bone wax, a bone repair material, a meniscus repair porous plate, a cerebral aneurysm clip, a silver clip, a vascular anastomosis clip (device), an orthopedic material, a heart or tissue repair material, an intra-ocular filling material, an eyelid repair reconstruction bracket, an intrauterine device and a nerve patch; the implantable artificial organ specifically includes: artificial esophagus, artificial skin, artificial blood vessel, artificial vertebral body, artificial joint, artificial urethra, artificial valve, artificial kidney, artificial breast, artificial skull, artificial jaw bone, artificial heart, artificial tendon, artificial cochlea and artificial anus sealer; the touch type artificial organ specifically comprises: artificial larynx, artificial skin, artificial cornea; the stent vessel specifically includes: stents, prostatic stents, biliary stents, esophageal stents, and ureteral stents; the organ assisting device specifically includes: implantable hearing aids, artificial liver support devices; extracorporeal circulation and blood treatment apparatus: pump, blood storage and filter, water filter (ultrafiltration), bubble remover, pump tube, blood circuit; a hemodialysis device, a hemodiafiltration device, a hemofiltration device, a blood purification pipeline, a dialysis blood circuit, a blood circuit plastic pump pipe, an arteriovenous puncture device, a multilayer flat plate type dialyzer, a hollow fiber filter, an adsorber, a plasma separator, a blood detoxification (perfusion) device, a blood purification extracorporeal circulation blood circuit (pipeline) and an intraoperative autoblood back transfusion machine; intervention equipment: an intravascular catheter: an intravascular angiography catheter, a balloon dilatation catheter, a central venous catheter, a trocar peripheral catheter, a micro floating catheter and an arteriovenous manometry catheter; the guide wire and the tube sheath specifically comprise: the device comprises a hard guide wire, a soft-head guide wire, a renal artery guide wire, a micro guide wire, a pushing guide wire, an ultra-smooth guide wire, an artery sheath, a vein sheath and a micro puncture sheath; an embolic device, comprising: filters, spring emboli, embolic microspheres, platinum microemboli, occluders, intravenous (IV), central Veins (CV), vascular access, pulmonary heat buffer balloons, angiography, angioplasty balloons, urology, specialty catheters, pacemaker lead insulation, vascular prostheses, heart valves, cardiac assist devices, left ventricular assist devices, intra-aortic balloon counterpulsation, total artificial heart, artificial kidney, hemodialysis, artificial lung, blood oxygen exchanger, blood perfusion, hemofiltration, blood washout, artificial pancreas, breast fillers, wound dressings, surgical anti-adhesion membranes, craniocerebral membranes, facial reconstruction materials, surgical adhesives, repair stents, resilient absorbable surgical sutures, hernia repair patches, soft tissue lifting straps (wires), drug controlled release, artificial tubes, for enhancing the flow and excretion of bodily fluids, contraceptives, penile prostheses, and the like.
The fourth application is as follows:
the composite of degradable polyurethane and a metal material or a polymer material is made into a structure, composition and shape suitable for a blood vessel, a vein, an esophagus, a biliary tract, a trachea, a bronchus, a small intestine, a large intestine, a urethra, a ureter or other segments close to the passageway of a tubular body, for example, as a vascular stent, a tracheal stent, a bronchial stent, a urethral stent, an esophageal stent, a biliary stent, a ureter stent (double J-tube), a ureter stenosis stent, a stent for a small intestine, a stent for a large intestine, a laryngeal implant, a bypass catheter or an ileostomy.
The application is as follows:
the medical apparatus or cosmetic product prepared from the degradable polyurethane can be added with commercially available or published polypeptides, proteins and active ingredients, including antiproliferative, anti-migratory, anti-angiogenic, anti-inflammatory, cytostatic, cytotoxic or antithrombotic drugs with physiological activities, such as: growth factors, doxorubicin, taxol, heparin, insulin-like growth factor, rapamycin, and the like.
The technical solution of the present invention is further illustrated below with reference to several specific examples.
Example one comparative test of physical Properties of degradable polyurethane of different structures
(1) Preparation of hydroxy-terminated degradable polyurethanes: respectively weighing epsilon-caprolactone, PEG-400 and stannous octoate (0.01 wt% of the total amount) as catalysts, adding the catalysts into a vacuum reaction bottle, adding a magnetic stirrer, vacuumizing/filling nitrogen for 3 times, sealing the opening of the vacuum reaction bottle under the vacuumizing condition, and placing the vacuum reaction bottle into an oil bath kettle at the temperature of between 100 and 140 ℃ for reaction for 12 to 24 hours to obtain the linear polymer. And adding L-lysine ethyl ester diisocyanate (LDI) and a proper amount of DMSO/DMF, vacuumizing and sealing the bottle mouth, putting the bottle mouth into an oil bath kettle at the temperature of 50-100 ℃ for reaction for 2-5h, adding a chain extender 1.4-butanediol, vacuumizing and sealing the oil bath kettle at the temperature of 50-100 ℃ for reaction for 4-20h to obtain a final product.
(2) D, preparing degradable polyurethane blocked by a compound: respectively weighing epsilon-caprolactone, PEG-400 and stannous octoate (0.01 wt% of the total amount) as catalysts, adding the catalysts into a vacuum reaction bottle, adding a magnetic stirrer, vacuumizing/filling nitrogen for 3 times, sealing the opening of the vacuum reaction bottle under the vacuumizing condition, and putting the vacuum reaction bottle into an oil bath kettle at the temperature of between 100 and 140 ℃ for reaction for 12 to 24 hours to obtain a linear polymer; adding L-lysine ethyl ester diisocyanate (LDI) and a proper amount of DMSO/DMF, vacuumizing and sealing the bottle mouth, putting the bottle mouth into an oil bath kettle at 50-100 ℃ for reaction for 2-5h, adding a chain extender (1.4-butanediol), reacting in the oil bath kettle at 50-100 ℃ for 4-20h, adding a compound with a structure D, vacuumizing and sealing the bottle mouth, and continuously reacting in the oil bath kettle at 50-100 ℃ for 2-10h to obtain a final product.
The specific addition of each component is shown in the following table:
the above structures are merely illustrative of the present invention, and include, but are not limited to, other materials mentioned in the present invention for improving the processability and biocompatibility of degradable polyurethane, without affecting the ratio and composition of each structure.
The infrared spectrums of the polyurethane with the two structures are shown in figures 1 and 2.
The melting temperature measured by the DSC and the contact angle measured by the surface contact angle measuring apparatus (shown in FIG. 3) were compared as follows:
the test results show that: when the q value is 1, the melting temperature of materials numbered 1 and 2 is lower than 40 ℃, the melting temperature of 5 x 1 cm sample strips quickly collapse under the environment of 37 ℃, the sample strips shrink into a ball and cannot keep the original state, the processing requirements of medical devices implanted into human bodies cannot be met, the synthesized materials have no practical application value, the contact angle of the materials grafted with the D compound is gradually reduced along with the increase of the q value, the hydrophilic performance of the materials is improved, when the q value reaches 6, the breaking elongation of the synthesized materials is reduced, the processing performance of the materials is reduced, the materials grafted with the D compound have good processing performance within the range that E/C is more than or equal to 20 percent and 1 is less than q & lt 6, and the biocompatibility of the degradable polyurethane material is correspondingly increased.
One of the application examples is as follows: preparing an electrostatic spinning micro-nano fiber film and evaluating the biocompatibility of degradable polyurethane with different structures:
dissolving the materials synthesized according to the formulas 3, 4, 5 and 6 in the embodiment 1 in an organic solvent (a mixed solvent of trichloromethane and DMF) to prepare a solution with the concentration of 10-15%, preparing a micro-nano fiber membrane with the thickness of 0.05-0.25 mm by adopting an electrostatic spinning process at the working voltage of 10-30KV, the distance between receiving plates of 10-20 cm and the sampling rate of 3.0-20 mL/h, placing the membrane in a vacuum drying box with the temperature of 40 ℃, drying until the solvent residue is less than 60ppm, paving the membrane in a cell culture plate, soaking the membrane in a culture medium for 8-12 hours, planting the 3 rd generation fibroblasts in the logarithmic growth phase in the subcutaneous rat, placing the membrane in a bovine serum containing 10% of fetal serum at 37 ℃, and 5% of CO ２ And culturing for 48 hours in a 95% humidity culture box, observing the form of the fibroblast under an inverted microscope, and taking a picture as shown in figure 4.
The second application example: the microspheres are prepared for repairing soft tissues or muscle tissues, and the specific implementation method is briefly introduced as follows:
(1) Dissolving degradable polyurethane in trichloromethane solution to prepare 5-25% solution;
(2) Adding the (1) into PVA solution with the concentration of 0.5-2%, fully stirring to prepare microspheres with the size of 10-100 um, and drying at 40 ℃ in vacuum until the solvent residue is qualified, so as to prepare the material for tissue filling or repairing.
The third application example: the coating of the medical appliance product implanted into the body is prepared for improving the biocompatibility of the product, and the specific implementation method is briefly introduced as follows:
(1) Dissolving degradable polyurethane in trichloromethane solution to prepare 5-50% solution;
(2) And (2) coating the non-degradable implanted metal material such as titanium alloy or the degradable metal material with the coating (1) by adopting the spraying, electrostatic spraying, dip-coating or plasma spraying technology to prepare the required coating.
The above description is only an example of the present invention and is not intended to limit the scope of the present invention, and all similar structures or processes used in the present specification or directly or indirectly applied to other related technical fields are encompassed by the present invention.
Claims (10)
1. The degradable polyurethane is characterized in that the degradable polyurethane contains an implant material and a compound D in the structure, and the structural formula of the degradable polyurethane is as shown in the formula
Shown in the figure:
The chemical structure of the compound D is as shown in the formula
Shown in the figure:
Formula (II)
The method comprises the following steps:
LDI is L-lysine (ethyl ester/methyl ester) diisocyanate, CL is caprolactone open ring, and the chemical bond between LDI and CL is a carbamate bond;
a: one selected from polyethylene glycol (200-1000) and small molecular diol monomer;
c: is a chain extender and is selected from one or two of compounds with two hydroxyl groups, two amino groups or as shown in E;
m, n and p are numbers 2-100;
is of the formula
The method comprises the following steps:
r: one selected from H, ethyl ester and methyl ester.
2. The degradable polyurethane of claim 1, wherein the degradable polyurethane comprises the following components in percentage by weight:
A：0.5%~15%
CL：50%~80%
LDI：5%~50%
C：0.5%~5%
D：0.01%~5%。
3. the degradable polyurethane of claim 1, wherein the degradable polyurethane comprises the following components in percentage by weight:
A：0.5%~15%
CL：50%~80%
LDI：5%~50%
C：0.5%~5%
D：0.01%~5%
E：0.01%~5%
wherein E is a compound obtained by reacting 2 molecules of chain extender and 1 molecule of LDI or 1 or more repeating units of the compound.
4. The degradable polyurethane of claim 1, comprising the following components in weight percent: :
A：0.5%~10%
CL：50%~80%
LDI：5%~50%
C：0.5%~5%
D：0.01%~5%
E：0.01%~5%
wherein, the percentage content of E in C is 20% -100%.
5. Degradable polyurethane according to claim 1, characterized in that the numbers of m, n, p further preferably:
m：5~50
n：5~50
P：5~50。
6. the degradable polyurethane of claim 1, wherein the degradable polyurethane contains trace amount of catalyst, specifically one or two of non-toxic organic metal catalyst;
c is selected from one or more of ethylene glycol, propylene glycol, butanediol, pentanediol, butanediamine, pentanediamine, diamine-like, hydroxyproline (methyl/ethyl ester), arginine (methyl/ethyl ester), cysteine (methyl/ethyl ester), cystine (methyl/ethyl ester), serine (methyl/ethyl ester), glutamic acid (methyl/ethyl ester), threonine (methyl/ethyl ester), aspartic acid (methyl/ethyl ester), leucine (methyl/ethyl ester), lysine (methyl/ethyl ester) and arginine (methyl/ethyl ester).
7. The use of degradable polyurethane is characterized by comprising the following uses:
(1) Preparing a tissue repair membrane material by an electrostatic spinning technology;
(2) Preparing soft tissue filling material by microsphere preparation technology;
(3) The titanium alloy coating material is used as a coating material of a medical appliance product implanted in a body, and is coated on a titanium alloy non-degradable implanted metal material or a degradable metal material through dip coating and spraying technologies so as to improve the biocompatibility of an implanted intervention appliance.
8. Use of the degradable polyurethane according to claim 7, characterized by further comprising the use of:
(4) Preparing tissue filling materials with different shapes by a 3D printing technology;
(5) The wire or the covered wire is prepared by a melt extrusion drawing technique.
9. Use of the degradable polyurethane according to claim 7 or 8, characterized in that the materials made of degradable polyurethane are used in medical and cosmetic products, including but not limited to, soft tissue regeneration repair, including: peripheral nerve repair sleeve, peripheral nerve repair coating film, peripheral nerve repair protective sheet, artificial skin, biodegradable coating, operation anti-adhesion film, craniocerebral membrane, cartilage repair bracket, bone filling material, meniscus repair porous plate, spinal annulus, wound repair film and dressing, elastic absorbable operation suture, hernia repair patch, and soft tissue lifting belt.
10. The use of degradable polyurethane is characterized in that polypeptide, collagen, protein and active ingredients are added into the degradable polyurethane to prepare the drugs with antiproliferative, anti-migration, anti-angiogenesis, anti-inflammation, cell growth inhibition, cytotoxicity or physiological activity added according to treatment needs.
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