CN117065080A - Medical adhesive and preparation method thereof - Google Patents

Medical adhesive and preparation method thereof Download PDF

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Publication number
CN117065080A
CN117065080A CN202210505890.6A CN202210505890A CN117065080A CN 117065080 A CN117065080 A CN 117065080A CN 202210505890 A CN202210505890 A CN 202210505890A CN 117065080 A CN117065080 A CN 117065080A
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compound
medical adhesive
functional group
carbon double
double bond
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程继业
金朝阳
王海梅
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Wanhua Chemical Group Co Ltd
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Wanhua Chemical Group Co Ltd
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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
    • C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
    • C08G75/02—Polythioethers
    • C08G75/04—Polythioethers from mercapto compounds or metallic derivatives thereof
    • C08G75/045—Polythioethers from mercapto compounds or metallic derivatives thereof from mercapto compounds and unsaturated compounds
    • 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
    • A61L24/001—Use of materials characterised by their function or physical properties
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
    • A61L24/04—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials
    • A61L24/046—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Surgery (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)

Abstract

The invention discloses a medical adhesive and a preparation method thereof. The medical adhesive comprises the reaction product of the following raw materials: 30% -55% of a compound of a polythiol functional group; 20-30 mole percent of compound with multi-carbon double bond functional groups; 20% -45% by mole of an adhesive compound; 0.001% -0.05% of catalyst. The medical adhesive takes hydrophobic aliphatic polyester as main resin and contains hydrophilic adhesion functional groups. The method has the advantages of strong operability in the actual use process, simple construction method, good adhesion performance and water soaking and flushing resistance.

Description

Medical adhesive and preparation method thereof
Technical Field
The invention belongs to the field of biomedical materials, and particularly relates to a medical adhesive and a preparation method thereof.
Background
Billions of suture operations are performed annually worldwide to close wounds or surgical incisions. Improper wound treatment not only results in slow healing but also can cause wound infection, which in severe cases can even be life threatening to the patient. However, the suture wound has complex operation and poor sealing property, and is easy to leak body fluid and cause infection. To solve the above problems, a specific polymer material is stuck to a wound site as an adhesive, which can effectively stop bleeding, seal a wound, prevent infection and promote wound healing. The medical adhesive has simple use method, improves the nursing quality, is not easy to generate scars, and is particularly suitable for the fields of surgery, dentistry, plastic cosmetology and the like.
Ideally, the medical adhesive is a liquid material that hardens the assembly after application to the wound surfaceThe fabrics are bonded together. And the surface of the biological tissue is rich in a large number of active groups (such as-NH) 2 The materials containing adhesion groups such as succinimide, aldehyde group, isocyanate, anhydride and catechol can achieve a strong tissue adhesion effect. To achieve the above object, the preparation of aqueous bioadhesives by dispersing functional polymeric materials in water is currently a common method in the art. The aqueous medical adhesive is poor in water adhesion due to inherent hydrophilicity and is not resistant to water washing. In addition, aqueous adhesives are also prone to fouling and bacterial attack on the body surface, causing wound infections. Based on the above problems, the university of Harvey medical institute (Ablood-resistant surgical glue for minimally invasive repair of vessels and heart defects [ J)]Sci.Transl.Med.,2014,6 (218): 218ra 6) a non-aqueous bioadhesive based on a hydrophobic aliphatic polyester material was developed. The hydrophobic adhesive material is itself in a liquid state, adheres to tissue under water, and resists water-washing. The adhesive material is an acrylate group with a hydrophobic end group, and the chain segment is aliphatic polyester containing eight methylene groups. The adhesive material hardens under light irradiation, thereby bonding the objects together. However, the light curing method is often limited by complex surface contours of the wound, poor light penetration, insufficient hardening adhesion, and reduced adhesion. In addition, the adhesive material lacks an adhesive functional group, and has poor adhesion effect to biological tissues. While the university of Jiangnan (CN 202010268527.8, CN202010271866.1 and CN 202011049135.9) develops a liquid polymer material which takes hydrophobic hyperbranched polythioether as a framework and takes hydrophobic thiol groups as terminal groups, and then the liquid polymer material and polyethylene glycol materials which respectively take acrylic ester, isocyanate and benzaldehyde as terminal groups are mixed to develop the non-aqueous polyether type biological adhesive which is light-cured, double-component mixed-cured and hot melt injected. However, the hydrophilic polyethylene glycol material contained in the adhesive may impair the adhesive effect and water resistance of the adhesive in water. Moreover, the adhesive material often suffers from uneven mixing of components, poor operability in actual use, narrow operation window, and the like in use.
Disclosure of Invention
In order to solve the defects and the shortcomings existing in the prior art, the invention provides the medical adhesive which has good tissue bonding effect, strong practical use operability and water resistance and the preparation method thereof. In order to achieve the aim of the invention, the adhesive material takes hydrophobic hyperbranched polyester as a framework structure and has hydrophilic adhesion groups modified on molecular chain side groups or end groups, thereby achieving the effect.
As one aspect of the present invention, the present invention provides the following technical solutions:
a medical adhesive comprising the reaction product of:
30-55 mole percent of polythiol functional group compound;
20-30 mole percent of compound with multiple carbon-carbon double bond functional groups;
20-45 mole percent of an adhesive compound;
0.001 to 0.05 mole percent of catalyst.
As a preferred embodiment, the medical adhesive comprises the reaction product of:
30-55 mol% of linear or multi-arm aliphatic polyester macromolecular monomer which takes the combination of saturated hydrocarbon chains containing five to ten carbons and ester bonds as a repeating unit and has the molecular weight of 500-2000 g/mol, wherein the end group is a mercaptan group;
20-30 mole percent of compound with multiple carbon-carbon double bond functional groups;
20-45 mole percent of an adhesive compound;
0.001 to 0.05 mole percent of catalyst.
As another preferred embodiment, the medical adhesive comprises the reaction product of:
30-55 mole percent of polythiol functional group compound;
20-30 mol% of linear or multi-arm aliphatic polyester macromolecular monomers with end groups of carbon-carbon double bond groups, a combination of saturated hydrocarbon chains containing five to ten carbons and ester bonds as a repeating unit and a molecular weight of 500-2000 g/mol;
20-45 mole percent of an adhesive compound;
0.001 to 0.05 mole percent of catalyst.
A preparation method of a medical adhesive comprises the following steps:
(1) Dissolving a compound with a polythiol functional group in an organic solvent, adding a catalyst, adding a compound with a multi-carbon double bond functional group, and reacting for 3-24 hours;
(2) Adding an adhesive compound into the reaction solution obtained in the step (1) for reaction for 6-24 hours.
As a preferable mode, the method of the invention further comprises (3) purifying the reaction liquid obtained in the step (2).
The compound with the polythiol functional group is a linear or multi-arm aliphatic polyester macromolecular monomer which has more than two thiol groups per molecule, has a molecular weight of less than 500g/mol, takes a small molecular monomer or a terminal group as a thiol group, takes a combination of a saturated hydrocarbon chain containing five to ten carbons and an ester bond as a repeating unit, and has a molecular weight of 500 to 2000 g/mol.
As a preferred embodiment, the polythiol functional compound is a polythiol functional compound having two or three thiol groups per molecule, such as ethylene dithiol, ethylene glycol bis (3-mercaptopropionate), trimethylolpropane tris (3-mercaptopropionate), or a compound of formula I:
wherein m=5 to 10, n=5 to 30, and at least two R 3 A group.
The compound with multiple carbon-carbon double bond functional groups is a small molecular monomer with more than two carbon-carbon double bonds per molecule and molecular weight less than 500g/mol, or a linear or multi-arm aliphatic polyester macromolecular monomer with a terminal group of carbon-carbon double bond groups, a combination of saturated hydrocarbon chains containing five to ten carbons and ester bonds as a repeating unit and molecular weight of 500-2000 g/mol.
As a preferred embodiment, the compound having a multi-carbon double bond functional group is a compound having two or three carbon-carbon double bonds per molecule, such as 3- (acryloyloxy) -2-hydroxypropyl methacrylate, 2- (acryloyloxy) ethyl methacrylate, trimethylolpropane trimethacrylate, or a compound of formula II:
wherein x=5 to 10, y=5 to 30, and there are at least 2R 6 A group.
The adhesive compound of the present invention refers to a compound containing both a thiol-reactive group including a carbon-carbon double bond, a halogen functional group, and the like, and an adhesive group including an acid anhydride group, a succinimidyl ester group, an aldehyde group, a phenylboronic acid group, a catechol group, and the like.
As a preferred embodiment, the adhesive compound of the present invention is selected from one or more of maleic anhydride, 4-bromomethylphenylboronic acid, 3-acrylamido dopamine.
The catalysts of the present invention include, but are not limited to, free radical thermal initiators commonly used in thiol-ene addition reactions, such as; azobisisobutyronitrile, benzoyl peroxide, free radical photoinitiators, such as; benzophenone, 2-hydroxy-4' - (2-hydroxyethoxy) -2-methylpropenone, 2-hydroxy-2-methyl-1-phenylpropion, 1-hydroxycyclohexylphenyl ketone, and the like, nucleophilic addition catalysts such as: triethylamine, triethylphosphorus, triphenylphosphine, tetramethylimidazole, and the like.
Wherein, the compound with polythiol functional group and the compound with multi-carbon double bond functional group are preferably selected to match, one with 2 degrees of functionality and one with 3 degrees of functionality, and one with small molecular monomer and one with large molecular monomer.
Wherein, when the catalyst is a free radical thermal initiator, the reaction condition is 50-100 ℃; when the catalyst is a free radical photoinitiator, the reaction condition is room temperature reaction under ultraviolet irradiation; when the catalyst is a nucleophilic addition catalyst, the reaction condition is room temperature.
The organic solvent includes, but is not limited to, one or more of N' N-dimethylformamide solution, acetonitrile, tetrahydrofuran, dichloromethane and the like.
As a preferred embodiment, the purification comprises the steps of: concentrating the reaction solution obtained in the step (2), adding a small amount of reaction solvent for redissolving, then dripping into absolute methanol for precipitation, taking the precipitate, repeating the dissolving-precipitating operation, and drying the precipitate in vacuum to obtain the adhesive.
The medical adhesive of the invention is in liquid state at room temperature, and the glass transition temperature is-60 to-20 ℃.
Wherein the chemical structure of the adhesive takes hydrophobic hyperbranched polyester as a framework and is modified with hydrophilic adhesive groups. The binder may cure the bonded object by spontaneously hydrophilic and hydrophobic association between the polymer segments.
As another aspect of the present invention, there is also provided a medical adhesive, which is prepared according to the method of preparing a medical adhesive as described in any one of the above.
The invention has the following beneficial effects:
(1) The adhesive provided by the invention is a water-insoluble liquid material, can directly bond biological tissues in water environment and can resist soaking and flushing of body fluid.
(2) The adhesive provided by the invention uses the aliphatic polyester material as the main resin, and the chemical structure of the adhesive contains a large number of hydrophilic adhesion functional groups, so that the adhesive has good adhesion performance to tissues.
(3) After the adhesive provided by the invention is coated on an object in a water environment, the adhesive can be spontaneously crosslinked and hardened through hydrophilic-hydrophobic association, so that the adhesive has strong operability in the actual use process and simple construction method.
Detailed Description
Adhesive strength test method: the hairless pigskin is cut into strips of 2.5cm x 5cm, the surface of the pigskin is sequentially wiped with isopropyl alcohol and water, the strips are dried to obtain the pigskin strips for testing, the adhesive materials in the following examples are coated on one ends of the two strips, the adhesive-coated parts are bonded together, and then the strips are placed in normal saline for 1 hour to enable the strips to be fully bonded together. The maximum adhesion was then determined by a tensile test, with a tensile rate of 5mm/min. The maximum adhesion was divided by the adhesion area to give the adhesion strength. Meanwhile, the bonded leather strips are placed in normal saline, antibacterial agents are added, and the leather strips are placed in a refrigerator at the temperature of 4 ℃ for soaking and storage for two weeks. The bond strength after soaking was then tested by the test method described above. The ratio of the adhesive strength after soaking to that before soaking is the water resistance of the adhesive.
Example 1
30g of polycaprolactone diol (Sigma-Aldrich, M) are weighed out n =500 g/mol) and 15g of methacryloyl chloride were dissolved in 200mL of dry dichloromethane, followed by dropwise addition of 12mL of triethylamine, and the reaction was carried out at room temperature for 24h. After the reaction was completed, the reaction solution was concentrated by rotary evaporation, and then the reaction solution was added dropwise to 500mL of anhydrous methanol. The lower precipitate was taken, redissolved with 50mL of dichloromethane, added dropwise again to 500mL of anhydrous methanol, and dried under vacuum to give polycaprolactone dimethacrylate.
9.964g of trimethylolpropane tris (3-mercaptopropionate) was dissolved in 300mL of tetrahydrofuran, followed by the addition of 19.2g of polycaprolactone dimethacrylate and 50mg of 2-hydroxy-4' - (2-hydroxyethoxy) -2-methylpropionne and reaction at room temperature under UV irradiation for 6 hours; then, 4.2g of maleic anhydride was added and the reaction was continued for 6 hours. The reaction solution was concentrated by distillation under reduced pressure, and then the product was redissolved with 40mL of tetrahydrofuran, followed by dropwise addition to 400mL of anhydrous methanol for precipitation. And taking the precipitate at the lower layer, repeating the dissolving-precipitating operation for 3 times, and vacuum drying to obtain the adhesive material.
Example 2
45g of polycaprolactone triol (Sigma-Aldrich, M) was weighed out n =900 g/mol), 15.18g of thioglycolic acid and 2.4g of 4-dimethylaminopyridine were dissolved in 300mL of dry dichloromethaneSubsequently, 100mL of a methylene chloride solution containing 34g of dicyclohexylcarbodiimide was added dropwise thereto, and the mixture was reacted at room temperature for 24 hours. After the reaction was completed, the reaction solution was concentrated by rotary evaporation, and then the reaction solution was added dropwise to 1000mL of anhydrous methanol. The lower precipitate was taken, redissolved with 50mL of dichloromethane, added dropwise again to 500mL of anhydrous methanol, and dried under vacuum to give polycaprolactone trithiol.
30g of polycaprolactone trithiol was dissolved in 500mL of tetrahydrofuran, followed by addition of 5.52g of 2- (acryloyloxy) ethyl methacrylate and 50mg of 2-hydroxy-4' - (2-hydroxyethoxy) -2-methylpropionate and reaction at room temperature under UV irradiation for 6h; then, 4.2g of maleic anhydride was added and the reaction was continued for 6 hours. The reaction solution was concentrated by distillation under reduced pressure, and then the product was redissolved with 40mL of tetrahydrofuran, followed by dropwise addition to 400mL of anhydrous methanol for precipitation. And taking the precipitate at the lower layer, repeating the dissolving-precipitating operation for 3 times, and vacuum drying to obtain the adhesive material.
Example 3
45g of polycaprolactone triol (Sigma-Aldrich, M) was weighed out n =900 g/mol), 17.3g of methacryloyl chloride was dissolved in 300mL of dry dichloromethane, followed by dropwise addition of 18mL of triethylamine, and the reaction was carried out at room temperature for 24h. After the reaction was completed, the reaction solution was concentrated by rotary evaporation, and then the reaction solution was added dropwise to 1000mL of anhydrous methanol. The lower precipitate was taken, redissolved with 50mL of dichloromethane, added dropwise again to 500mL of anhydrous methanol, and dried under vacuum to give polycaprolactone trimethacrylate.
3.53g of ethanedithiol was dissolved in 300mL of tetrahydrofuran, followed by addition of 21g of polycaprolactone trimethacrylate and 50mg of 2-hydroxy-4' - (2-hydroxyethoxy) -2-methylpropionate, and reaction was carried out at room temperature under UV irradiation for 6 hours; then, 1.467g of maleic anhydride was added, and the reaction was continued for 6 hours. The reaction solution was concentrated by distillation under reduced pressure, and then the product was redissolved with 40mL of tetrahydrofuran, followed by dropwise addition to 400mL of anhydrous methanol for precipitation. And taking the precipitate at the lower layer, repeating the dissolving-precipitating operation for 3 times, and vacuum drying to obtain the adhesive material.
Example 4
30g of poly (ethylene-propylene) is weighedCaprolactone diol (sigma-aldrich, M n =500 g/mol), 13.7g of thioglycolic acid and 1.8g of 4-dimethylaminopyridine were dissolved in 200mL of dried dichloromethane, followed by dropwise addition of 50mL of a dichloromethane solution containing 26g of dicyclohexylcarbodiimide, and reaction was carried out at room temperature for 24 hours. After the reaction was completed, the reaction solution was concentrated by rotary evaporation, and then the reaction solution was added dropwise to 1000mL of anhydrous methanol. The lower precipitate was taken, redissolved with 50mL of dichloromethane, added dropwise again to 500mL of anhydrous methanol, and dried under vacuum to give polycaprolactone dithiol.
19.5g of polycaprolactone dithiol was dissolved in 200mL of tetrahydrofuran, followed by addition of 4.72g of trimethylolpropane trimethacrylate and 50mg of 2-hydroxy-4' - (2-hydroxyethoxy) -2-methylpropionate, and reacted at room temperature under UV irradiation for 6 hours; then, 1.17g of maleic anhydride was added and the reaction was continued for 6 hours. The reaction solution was concentrated by distillation under reduced pressure, and then the product was redissolved with 50mL of tetrahydrofuran, followed by dropwise addition to 500mL of anhydrous methanol for precipitation. And taking the precipitate at the lower layer, repeating the dissolving-precipitating operation for 3 times, and vacuum drying to obtain the adhesive material.
Example 5
30g of the polycaprolactone trithiol prepared in example 2 was dissolved in 500mL of tetrahydrofuran, followed by the addition of 5.52g of 2- (acryloyloxy) ethyl methacrylate and 50mg of 2-hydroxy-4' - (2-hydroxyethoxy) -2-methylpropionne, and reacted for 6 hours at room temperature under UV irradiation; then, 8.4g of 4-bromomethylphenylboronic acid was added thereto, and the reaction was continued for 6 hours. The reaction solution was concentrated by distillation under reduced pressure, and then the product was redissolved with 40mL of tetrahydrofuran, followed by dropwise addition to 400mL of anhydrous methanol for precipitation. And taking the precipitate at the lower layer, repeating the dissolving-precipitating operation for 3 times, and vacuum drying to obtain the adhesive material.
Example 6
30g of the polycaprolactone trithiol prepared in example 2 was dissolved in 500mL of tetrahydrofuran, followed by the addition of 5.52g of 2- (acryloyloxy) ethyl methacrylate and 50mg of 2-hydroxy-4' - (2-hydroxyethoxy) -2-methylpropionne, and reacted for 6 hours at room temperature under UV irradiation; 16.8g of 3-acrylamido dopamine are then added and the reaction is continued for 6h. The reaction solution was concentrated by distillation under reduced pressure, and then the product was redissolved with 40mL of tetrahydrofuran, followed by dropwise addition to 400mL of anhydrous methanol for precipitation. And taking the precipitate at the lower layer, repeating the dissolving-precipitating operation for 3 times, and vacuum drying to obtain the adhesive material.
Comparative example 1
9.964g of trimethylolpropane tris (3-mercaptopropionate) was dissolved in 300mL of tetrahydrofuran, followed by addition of 22.4g of polycaprolactone dimethacrylate and 50mg of 2-hydroxy-4' - (2-hydroxyethoxy) -2-methylpropionne and reaction at room temperature under UV irradiation for 6 hours; then, 4.2g of maleic anhydride was added and the reaction was continued for 6 hours. The reaction solution was concentrated by distillation under reduced pressure, and then the product was redissolved with 40mL of tetrahydrofuran, followed by dropwise addition to 400mL of anhydrous methanol for precipitation. And taking the precipitate at the lower layer, repeating the dissolving-precipitating operation for 2 times, and vacuum drying to obtain the adhesive material.
Comparative example 2
9.964g of trimethylolpropane tris (3-mercaptopropionate) was dissolved in 300mL of tetrahydrofuran, followed by the addition of 19.2g of polycaprolactone dimethacrylate and 50mg of 2-hydroxy-4' - (2-hydroxyethoxy) -2-methylpropionne and the reaction at room temperature under UV irradiation for 6 hours. The reaction solution was concentrated by distillation under reduced pressure, and then the product was redissolved with 40mL of tetrahydrofuran, followed by dropwise addition to 400mL of anhydrous methanol for precipitation. And taking the precipitate at the lower layer, repeating the dissolving-precipitating operation for 3 times, and vacuum drying to obtain the adhesive material.
Comparative example 3
9.965g of trimethylolpropane tris (3-mercaptopropionate) was dissolved in 300mL of tetrahydrofuran, and then 14g of polyethylene glycol dimethacrylate (sigma-aldrich, m=700 g/mol) and 50mg of 2-hydroxy-4' - (2-hydroxyethoxy) -2-methylpropionne were added and reacted at room temperature under ultraviolet irradiation for 6 hours; then, 3.5g of maleic anhydride was added and the reaction was continued for 6 hours. The reaction solution was distilled off under reduced pressure to dryness, and then the product was redissolved with 40mL of tetrahydrofuran, followed by dropwise addition to 400mL of anhydrous diethyl ether for precipitation. And taking the precipitate at the lower layer, repeating the dissolving-precipitating operation for 3 times, and vacuum drying to obtain the adhesive material.
The material properties of the examples and comparative examples are shown in Table 1.
Table 1 material properties of examples and comparative examples

Claims (10)

1. A medical adhesive comprising the reaction product of:
30-55 mole percent of polythiol functional group compound;
20-30 mole percent of compound with multiple carbon-carbon double bond functional groups;
20-45 mole percent of an adhesive compound;
0.001 to 0.05 mole percent of catalyst.
2. The medical adhesive according to claim 1, wherein the polythiol functional compound is a linear or multi-arm aliphatic polyester-based macromer having a thiol group as a terminal group, a combination of a saturated hydrocarbon chain having five to ten carbons and an ester bond as a repeating unit, and a molecular weight of 500 to 2000 g/mol.
3. The medical adhesive according to claim 1, wherein the compound having a multi-carbon double bond functional group is a linear or multi-arm aliphatic polyester-based macromer having a terminal carbon-carbon double bond group, a combination of saturated hydrocarbon chains having five to ten carbons and ester bonds as a repeating unit, and a molecular weight of 500 to 2000 g/mol.
4. The medical adhesive according to claim 2, wherein the compound having a multi-carbon double bond functional group is a small molecular monomer having more than two carbon-carbon double bonds per molecule and a molecular weight of less than 500 g/mol; preferably one or more of 3- (acryloyloxy) -2-hydroxypropyl methacrylate, 2- (acryloyloxy) ethyl methacrylate and trimethylolpropane trimethacrylate.
5. The medical adhesive according to claim 2 or 4, wherein the polythiol functional compound is a compound of formula I:
wherein m=5 to 10, n=5 to 30, and at least two R 3 A group.
6. The medical adhesive according to claim 3, wherein the polythiol functional group compound is a small molecular monomer having more than two thiol groups per molecule and a molecular weight of less than 500 g/mol; preferably one or more of ethanedithiol, ethylene glycol bis (3-mercaptopropionate), and trimethylolpropane tris (3-mercaptopropionate).
7. The medical adhesive according to claim 3 or 6, wherein the compound having a multi-carbon double bond functional group is a compound represented by formula II:
wherein x=5 to 10, y=5 to 30, and there are at least 2R 6 A group.
8. The medical adhesive according to any one of claims 1-7, wherein the adhesion compound is selected from one or more of maleic anhydride, 4-bromomethylphenylboronic acid, 3-acrylamido dopamine.
9. The medical adhesive according to any one of claims 1 to 8, wherein one of the materials of the polythiol functional group compound and the multi-carbon double bond functional group compound has a functionality of 2, the other material has a functionality of 3, and one material is a small molecular monomer and the other material is a large molecular monomer.
10. A method of preparing the medical adhesive of any one of claims 1-9, comprising the steps of:
(1) Dissolving a compound with a polythiol functional group in an organic solvent, adding a catalyst, adding a compound with a multi-carbon double bond functional group, and reacting for 3-24 hours;
(2) Adding an adhesive compound into the reaction solution obtained in the step (1) for reaction for 6-24 hours.
CN202210505890.6A 2022-05-10 2022-05-10 Medical adhesive and preparation method thereof Pending CN117065080A (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN118059327A (en) * 2024-01-25 2024-05-24 明澈生物科技(苏州)有限公司 Photo-curing material, glaucoma drainage device and preparation method thereof
CN118059326A (en) * 2024-01-25 2024-05-24 明澈生物科技(苏州)有限公司 Photo-curing material, ophthalmic drainage device and preparation method thereof

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN118059327A (en) * 2024-01-25 2024-05-24 明澈生物科技(苏州)有限公司 Photo-curing material, glaucoma drainage device and preparation method thereof
CN118059326A (en) * 2024-01-25 2024-05-24 明澈生物科技(苏州)有限公司 Photo-curing material, ophthalmic drainage device and preparation method thereof

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