CN106693039B - A kind of preparation method of the medical aquogel with good biological adhesiveness - Google Patents

A kind of preparation method of the medical aquogel with good biological adhesiveness Download PDF

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CN106693039B
CN106693039B CN201710059324.6A CN201710059324A CN106693039B CN 106693039 B CN106693039 B CN 106693039B CN 201710059324 A CN201710059324 A CN 201710059324A CN 106693039 B CN106693039 B CN 106693039B
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polyethylene glycol
arm polyethylene
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solution
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CN106693039A (en
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伍国琳
单萌
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Nankai University
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61LMETHODS 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
    • A61L24/00Surgical adhesives or cements; Adhesives for colostomy devices
    • A61L24/001Use of materials characterised by their function or physical properties
    • A61L24/0031Hydrogels or hydrocolloids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61LMETHODS 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
    • A61L24/00Surgical adhesives or cements; Adhesives for colostomy devices
    • A61L24/001Use of materials characterised by their function or physical properties
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61LMETHODS 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
    • A61L24/00Surgical adhesives or cements; Adhesives for colostomy devices
    • A61L24/04Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials
    • A61L24/046Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00Processes of treating or compounding macromolecular substances
    • C08J3/02Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
    • C08J3/03Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
    • C08J3/075Macromolecular gels
    • GPHYSICS
    • G01MEASURING; TESTING
    • G01NINVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N19/00Investigating materials by mechanical methods
    • G01N19/04Measuring adhesive force between materials, e.g. of sealing tape, of coating
    • GPHYSICS
    • G01MEASURING; TESTING
    • G01NINVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N21/00Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
    • G01N21/17Systems in which incident light is modified in accordance with the properties of the material investigated
    • G01N21/25Colour; Spectral properties, i.e. comparison of effect of material on the light at two or more different wavelengths or wavelength bands
    • G01N21/29Colour; Spectral properties, i.e. comparison of effect of material on the light at two or more different wavelengths or wavelength bands using visual detection
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    • C08J2371/00Characterised by the use of polyethers obtained by reactions forming an ether link in the main chain; Derivatives of such polymers
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    • GPHYSICS
    • G01MEASURING; TESTING
    • G01NINVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N2203/00Investigating strength properties of solid materials by application of mechanical stress
    • G01N2203/0001Type of application of the stress
    • G01N2203/0003Steady
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    • G01MEASURING; TESTING
    • G01NINVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N2203/00Investigating strength properties of solid materials by application of mechanical stress
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Abstract

A kind of preparation method of the medical aquogel with good biological adhesiveness, the raw material for preparing the hydrogel includes the four arm polyethylene glycol dopamines and four arm polyethylene glycol phenyl boric acids of terminal groups modification, covalent cross-linking forms hydrogel after two kinds of group lease making blend tool physical mixeds, comprising the following steps: 1) preparation of four arm polyethylene glycol dopamines;2) preparation of four arm polyethylene glycol phenyl boric acids;3) preparation of medical aquogel;The invention has the advantages that due to the presence of DOPA amine groups, impart the stronger bioadhesive of hydrogel, it can selfreparing, the medical aquogel preparation method is simple, and compared with traditional medical adhesive, have it is reusable, it is biodegradable, good biocompatibility, the advantages that can be used for the biological environment of different parts.

Description

A kind of preparation method of the medical aquogel with good biological adhesiveness
Technical field
The invention belongs to biodegradable polymer field, more particularly to a kind of with good biological adhesiveness The preparation method of medical aquogel.
Background technique
Hydrogel has tridimensional network, is used for multiple fields, such as in bio-medical, can be used for organizational project and Drug release etc..Hydrogel with self-reparing capability can extend its service life.It is some to be similar to the natural of hydrogel Biological tissue inherently has superior self-reparing capability, such as heart valve.Usual dynamic non-covalent key, which can be prepared, to be had certainly Repair ability hydrogel allows to reuse.Phenyl boric acid and vicinal diamines can form dynamic boric acid ester bond.Bioadhesive Agent requires good bioadhesive, and describing property of biology is good, degradable.The invention is derived from the adherency of marine mussel secretion Albumen, the higher dopamine of content (DOPA) has been the main component of adhesive attraction in this protein, and its resulting structure is just It is 3,4- dihydroxy-phenylalanine.It can realize good life by forming covalent bond with functional groups such as sulfydryl, amino Object adhesive attraction.
Summary of the invention
It is an object of the invention to analyze in view of the above technology and there are problem, provide it is a kind of it is reusable, have The preparation method of the medical aquogel of good biological adhesiveness, this method is by four arm polyethylene glycol Succinimidyl glutarates It is terminal-modified that four arm polyethylene glycol amino terminals are modified to phenyl boric acid at dopamine, the four arm polyethylene glycol DOPA that will be obtained Amine and four arm polyethylene glycol phenyl boric acid solution are mixed, and polyester resin is formed in situ.And due to the formation of dynamic boric acid ester bond, So that hydrogel has self-reparing capability, the presence of DOPA amine groups also gives the good bioadhesive of hydrogel simultaneously. Hydrogel precursor polymer in the present invention is four arm polyethylene glycol dopamines and four arm polyethylene glycol phenyl boric acids.The poly- second two of four arms It is Material synthesis that alcohol dopamine, which is with the dopamine hydrochloride of four arm polyethylene glycol Succinimidyl glutarates and small molecule,. Four arm polyethylene glycol phenyl boric acids are preparing to Carboxybenzeneboronic acid pinacol ester with four arm polyethylene glycol amino and small molecule.
Technical solution of the present invention:
A kind of preparation method of the medical aquogel with good biological adhesiveness, comprising the following steps:
1) preparation of four arm polyethylene glycol dopamines
Four arm polyethylene glycol Succinimidyl glutarates and dimethyl sulfoxide are mixed to get reaction solution a, the poly- second of four arms The amount ratio of glycol Succinimidyl glutarate and dimethyl sulfoxide is 0.1mmol:4mL;By dopamine hydrochloride and diformazan Base sulfoxide is mixed to get reaction solution b, and the amount ratio of dopamine hydrochloride and dimethyl sulfoxide is 0.6mmol:1mL;By reaction solution a It is mixed with reaction solution b, adds triethylamine and be uniformly mixed, react 3 days under room temperature, precipitated with ether, filter, obtain white solid Four arm polyethylene glycol dopamines, mole of four arm polyethylene glycol Succinimidyl glutarates, dopamine hydrochloride and triethylamine Than for 1:6:6;
2) preparation of four arm polyethylene glycol phenyl boric acids
Four arm polyethylene glycol amino and methylene chloride are mixed to get mixed liquor a, four arm polyethylene glycol amino and dichloromethane The amount ratio of alkane is 0.1mmol:5mL;Mixed liquor b will be mixed to get to Carboxybenzeneboronic acid pinacol ester and methylene chloride, to carboxylic The amount ratio of base phenyl boric acid pinacol ester and methylene chloride is 0.8mmol:1mL;By DCC (N, N '-dicyclohexylcarbodiimide) It is mixed to get mixed liquor c with methylene chloride, DCC (N, N '-dicyclohexylcarbodiimide) and the amount ratio of methylene chloride are 0.8mmol:2mL;Three kinds of mixed liquors a, b, c are mixed, four arm polyethylene glycol amino, to Carboxybenzeneboronic acid pinacol ester and DCC The molar ratio of (N, N '-dicyclohexylcarbodiimide) is 0.1:0.8:0.8, and stirring at normal temperature is reacted 1 day, is first filtered to remove precipitating, Filtrate is precipitated with the ether of 70mL, and the amount ratio of four arm polyethylene glycol amino and ether is 0.1mmol:70mL, obtains after suction filtration Four arm polyethylene glycol phenyl boric acid of white solid;
3) preparation of medical aquogel
Four arm polyethylene glycol dopamines are added in the 0.01mol/L sodium borate decahydrate buffer solution of pH=9 and are configured At the solution a of 15wt%;The 0.01mol/L sodium borate decahydrate buffering that pH=9 is added in four arm polyethylene glycol phenyl boric acids is molten The solution b of 15wt% is configured in liquid;It will be mixed under solution a and solution b room temperature, the volume ratio of solution a and solution b are 1:1, system Obtain medical aquogel.
The molecular weight of the four arms polyethylene glycol Succinimidyl glutarate is 5000-50000, four arm polyethylene glycol ammonia The molecular weight of base is 10000.
The preparation method of the medical aquogel is as follows:
(A)
(B)
A kind of detection method of the prepared medical aquogel with good biological adhesiveness, steps are as follows:
1) one piece of integral gel is cut into two pieces, and uses methylene blue staining for one of, later by two blocks of hydrogels Section put together, the selfreparing of gel can be significantly observed in 30s;
2) pigskin is cut into 2.5cm × 3cm, impregnates 1h in 37 DEG C of phosphate buffered saline solution, uses cyanoacrylate Class adhesive adheres to pigskin on a glass, solidifies 1h, and the hydrogel 0.6g for weighing preparation is coated in pigskin end, covers same The glass plate of pigskin is adhered to, a complete model is formed, overlapping area is recorded with digital display calliper, then uses 100g counterweight pressure 30min, with tensilon (thinking carefully Science and Technology Co., Ltd. in length and breadth in Shenzhen) with the speed tensile of 5mm/min, record is maximum Power detects adhesion property.
The invention has the advantages that this method preparation medical aquogel have good biological adhesiveness, can selfreparing, Medical domain can play a significant role, and have a extensive future.
Detailed description of the invention
Fig. 1 is the self-healing properties detection of the Medical Adhesive hydrogel of preparation.
Fig. 2 is the adhesion property detection of the Medical Adhesive hydrogel of preparation.
Specific embodiment
The technical solution that present invention will be further explained below with reference to specific examples.These embodiments are only used for this explanation Rather than the range of limitation invention.In addition, it should also be understood that, after reading the contents of the present invention, those skilled in the art can be with The present invention is made various changes or modifications, such equivalent forms equally fall into protection scope defined by the present invention.In embodiment Test method without specific conditions, usually according to normal condition and condition described in handbook, or according to manufacturer Proposed condition;Material, reagent used etc., it is commercially available unless otherwise specified.
Embodiment:
A kind of preparation method of the medical aquogel with good biological adhesiveness, comprising the following steps:
1) preparation of four arm polyethylene glycol dopamines
It weighs 1g, the four arm polyethylene glycol Succinimidyl glutarates that molecular weight is 10000, the dimethyl of 4mL is added Sulfoxide is allowed to dissolve;Dopamine hydrochloride 0.1g is weighed, 1mL dimethyl sulfoxide is added and is allowed to dissolve;Two reaction solutions are mixed, then 83 μ L triethylamine, 83 μ L is reacted 3 days under room temperature, is precipitated with ether, is filtered, is obtained four arm polyethylene glycol dopamine white solids 0.9g, yield 90%, obtained solid vacuum save backup.
2) preparation of four arm polyethylene glycol phenyl boric acids
Weigh 1g, the four arm polyethylene glycol amino that molecular weight is 10000, the methylene chloride that 5mL is added is allowed to dissolve;It weighs To Carboxybenzeneboronic acid pinacol ester 0.2g, the methylene chloride that 1mL is added is allowed to dissolve;Weigh DCC (N, N '-dicyclohexyl carbon two Imines) 0.2g, it is allowed to dissolve with the methylene chloride of 2mL;Three kinds of mixed liquors are mixed, stirring at normal temperature is reacted 1 day, is first filtered to remove Precipitating, filtrate are precipitated with the ether of 70mL, filter, obtain) four arm polyethylene glycol phenyl boric acid white solid 0.85g, yield 85%, Obtained white solid is placed in spare in drier.
3) preparation of medical aquogel
Weigh ten water of 0.01mol/L that pH=9 is added in four arm polyethylene glycol dopamine white solids obtained in step 1) Close the four arm polyethylene glycol dopamine solution a that 15wt% is configured in sodium tetraborate buffer solution;It weighs obtained in step 2) Four arm polyethylene glycol phenyl boric acid white solids, are added in the 0.01mol/L sodium borate decahydrate buffer solution of pH=9 and are configured to The four arm polyethylene glycol phenyl boric acid solution b of 15wt%;By solution a with, mixed under solution b room temperature, be made medical aquogel.
The detection of the medical aquogel of preparation:
1) the self-healing properties detection of medical aquogel
One piece of integral gel is cut into two pieces, and uses methylene blue staining for one of, later by two blocks of hydrogels Section is put together, and the selfreparing of gel can be significantly observed in 30s.Testing result is referring to Fig. 1, in figure: a is to be cut into two The gel of block, it is one of to use methylene blue staining;B is that the section of two blocks of hydrogels is put together, places 30s;C is to use tweezer Sub-folder plays the selfreparing situation that its section is observed in hydrogel one end.As can be seen from the results, which has selfreparing function Energy.
2) the adhesion property detection of medical aquogel
Pigskin is cut into 2.5cm × 3cm, impregnates 1h in 37 DEG C of PBS.With cyano-acrylate binder by pigskin Adherency on a glass, solidifies 1h, weighs medical aquogel 0.6g obtained and is coated in pigskin end, covers same adherency pigskin Glass plate forms a complete model, records overlapping area with digital display calliper.30min is pressed with 100g counterweight later.With omnipotent Puller system (thinking carefully Science and Technology Co., Ltd. in length and breadth in Shenzhen) records maximum, force with the speed tensile of 5mm/min.Each sample is surveyed It averages for 5 times.Referring to fig. 2, in figure: a is the schematic diagram that sample is used in the detection of hydrogel adhesion property to testing result, and b is with pig Skin and glass plate are the primary and secondary adhesive strength figure of substrate surface.As can be seen from the results, the hydrogel is to pigskin Adhesion strength can reach 5kPa, and the secondary adhesion strength after selfreparing weakens there is no obvious.

Claims (2)

1. a kind of preparation method of the medical aquogel with good biological adhesiveness, it is characterised in that steps are as follows:
1) preparation of four arm polyethylene glycol dopamines
Four arm polyethylene glycol Succinimidyl glutarates and dimethyl sulfoxide are mixed to get reaction solution a, four arm polyethylene glycol The amount ratio of Succinimidyl glutarate and dimethyl sulfoxide is 0.1mmol:4mL;Dopamine hydrochloride and dimethyl is sub- Sulfone is mixed to get reaction solution b, and the amount ratio of dopamine hydrochloride and dimethyl sulfoxide is 0.6mmol:1mL;By reaction solution a and instead It answers liquid b to mix, adds triethylamine and be uniformly mixed, react 3 days under room temperature, precipitated with ether, filter, obtain four arm of white solid The molar ratio of polyethylene glycol dopamine, four arm polyethylene glycol Succinimidyl glutarates, dopamine hydrochloride and triethylamine is 1:6:6;
2) preparation of four arm polyethylene glycol phenyl boric acids
Four arm polyethylene glycol amino and methylene chloride are mixed to get mixed liquor a, four arm polyethylene glycol amino and methylene chloride Amount ratio is 0.1mmol:5mL;Mixed liquor b will be mixed to get to Carboxybenzeneboronic acid pinacol ester and methylene chloride, to carboxyl benzene The amount ratio of pinacol borate and methylene chloride is 0.8mmol:1mL;By DCC (N, N '-dicyclohexylcarbodiimide) and two Chloromethanes is mixed to get mixed liquor c, and DCC (N, N '-dicyclohexylcarbodiimide) and the amount ratio of methylene chloride are 0.8mmol: 2mL;Three kinds of mixed liquors a, b, c are mixed, four arm polyethylene glycol amino, to Carboxybenzeneboronic acid pinacol ester and DCC (N, N '-two Carbodicyclo hexylimide) molar ratio be 0.1:0.8:0.8, stirring at normal temperature is reacted 1 day, is first filtered to remove precipitating, filtrate use The ether of 70mL precipitates, and the amount ratio of four arm polyethylene glycol amino and ether is 0.1mmol:70mL, and it is solid that white is obtained after suction filtration Four arm polyethylene glycol phenyl boric acid of body;
3) preparation of medical aquogel
Four arm polyethylene glycol dopamines are added in the 0.01mol/L sodium borate decahydrate buffer solution of pH=9 and are configured to The solution a of 15wt%;Four arm polyethylene glycol phenyl boric acids are added to the 0.01mol/L sodium borate decahydrate buffer solution of pH=9 In be configured to the solution b of 15wt%;It will be mixed under solution a and solution b room temperature, the volume ratio of solution a and solution b are 1:1, are made Medical aquogel.
2. the preparation method of the medical aquogel with good biological adhesiveness according to claim 1, it is characterised in that: institute The molecular weight for stating four arm polyethylene glycol Succinimidyl glutarates is 5000-50000, the molecular weight of four arm polyethylene glycol amino It is 10000.
CN201710059324.6A 2017-01-24 2017-01-24 A kind of preparation method of the medical aquogel with good biological adhesiveness Expired - Fee Related CN106693039B (en)

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