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Temperature-induced gelatinizing-in-situ triblock copolymer, preparation method and applications

An in-situ gel and temperature-induced technology, applied in the field of vascular embolization materials, can solve the problems of easy precipitation, dehydration and collapse of polymer chain segments, and the inability to pre-design the molecular structure of copolymer materials, etc., to achieve fast transformation and good biological compatibility effect

Inactive Publication Date: 2008-11-19
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Recently, our research group [4, 5] prepared a terpolymer vascular embolization material based on isopropylacrylamide, which successfully embolized the network of cerebral arterial malformation in domestic pigs (Chinese invention patent ZL200510013133.3) , but because the above two materials use random free radical copolymerization, the molecular structure of the copolymer material cannot be pre-designed, and the molecular weight and distribution index of the copolymer cannot be controlled
In addition, when the temperature of the temperature-sensitive random copolymer exceeds the LCST, the polymer chain segment dehydrates and collapses, and it is easy to precipitate out.

Method used

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  • Temperature-induced gelatinizing-in-situ triblock copolymer, preparation method and applications
  • Temperature-induced gelatinizing-in-situ triblock copolymer, preparation method and applications
  • Temperature-induced gelatinizing-in-situ triblock copolymer, preparation method and applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Add the bifunctional initiator diethyl m-2,5-dibromoadipate (9.1mg, 0.025mmol), the catalyst cuprous chloride (4.9mg, 0.05mmol) and 2mL of methanol into the Schleck tube, and use liquid Nitrogen freezing (-198°C), degassing, and then thawing the system at 25°C while blowing nitrogen, repeated freezing and thawing three times in order to remove oxygen in the reaction system. The monomer isopropylacrylamide (NIPAAm) (1.3578g, 11.998mmol, theoretical degree of polymerization: 480) and the ligand 1,4,8,11-tetramethyl-1,4,8,11-tetrazaza Cyclotetradecane (12.8 mg, 0.050 mmol) was dissolved in 6 mL of methanol and transferred to the reaction vessel with a syringe under nitrogen protection. After the reaction mixture was repeatedly frozen and thawed three times, it was returned to room temperature (25° C.), and the reaction vessel was vacuum-sealed. After reacting for 6 hours, nitrogen gas with a purity of 99.99% was passed into the reaction system. Dissolve 2-hydroxyethyl met...

Embodiment 2

[0032] Add the bifunctional initiator diethyl m-2,5-dibromoadipate (9.1mg, 0.025mmol), the catalyst cuprous chloride (4.9mg, 0.05mmol) and 2mL of methanol into the Schleck tube, and use liquid Nitrogen freezing (-198°C), degassing, and then dissolving with nitrogen gas, repeated freezing and thawing three times in order to remove oxygen in the reaction system. The monomer isopropylacrylamide (NIPAAm) (1.8103g, 16mmol, theoretical degree of polymerization: 640) and the ligand 1,4,8,11-tetramethyl-1,4,8,11-tetrazazacyclo Tetradecane (12.8 mg, 0.050 mmol) was dissolved in 6 mL of methanol and transferred to the reaction vessel with a syringe under nitrogen protection. After the reaction mixture was repeatedly frozen and thawed three times, it was returned to room temperature, vacuum-sealed, and after 6 hours of magnetic stirring reaction, 99.99% nitrogen was passed into the reaction system, and 2ml of 2-hydroxyethyl methacrylate (HEMA) (0.2603 g, 2.0mmol, the theoretical polymer...

Embodiment 3

[0037] Diethyl m-2,5-dibromoadipate (9.1mg, 0.025mmol) and cuprous chloride (12.8mg, 0.050mmol) were used to add the bifunctional initiator into the Schleck tube, and frozen with liquid nitrogen (- 198°C), degassed, and then dissolved in nitrogen, so repeated freezing and thawing three times to remove oxygen in the reaction system. The monomer 2-hydroxyethyl methacrylate (HEMA) (0.2603g, 2.000mmol, theoretical degree of polymerization: 80) and the ligand 1,4,8,11-tetramethyl-1,4,8,11 - Tetrazaazacyclotetradecane (12.8 mg, 0.050 mmol) was dissolved in 6 mL of methanol at 25° C. in methanol and transferred to the reaction vessel with a syringe under nitrogen protection. After the reaction mixture was repeatedly frozen and thawed three times, it was returned to room temperature, and the reaction vessel was vacuum-sealed. After 6 hours of magnetic stirring reaction, 99.99% nitrogen was passed into the reaction system, and 6ml of isopropylacrylamide (NIPAAm) (1.810g, 16 mmol, each...

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Abstract

The invention discloses a triblock copolymer by temperature induction and in-situ gelation, a method for preparing the triblock copolymer and an application of the triblock copolymer. The triblock copolymer comprises an ABA type and a BAB type, wherein, a section A is a polyN-isopropyl acrylamide; a section B is polymethacrylic acid-2-hydroxylethyl ester. The copolymer preparation process comprises the following steps that: the N-isopropyl acrylamide and the polymethacrylic acid-2-hydroxylethyl ester are used as monomers; m-2,5- dibromo adipate diethyl ester is used as a bifunctional initiator; and cuprous chloride, 1,4,8,11- tetramethyl-1,4,8,11-tetranitrogen heterocyclic ring tetradecane are used as a catalytic system; various compositions are prepared to a methanol solution and added into a mesonephric tube; oxygen in the system is removed by liquid nitrogen; and the ABA or the BAB type triblock copolymer is synthesized in the methanol solution at a temperature of 25 DEG C through feeding in sequence. The triblock copolymer, the method and the application have the advantages that: LCST(lower critical solution temperature) of the copolymer is controlled to between 26 and 34 DEG C, which is close to human temperature; the time for sol-gel transition is controlled within 60 minutes; and the copolymer has good biocompatibility and can be used as a vascular embolization material.

Description

technical field [0001] The invention relates to a temperature-induced in-situ gelation tri-block copolymer, a preparation method and application thereof, and belongs to the technology of vascular embolization materials in the field of biomedical engineering. Background technique [0002] Endovascular interventional therapy is one of the important measures to treat cerebrovascular malformation (AVM). In the past, people have been trying to use various embolization materials to treat cerebral AVM, such as solid particles, silk threads, alcohol, microcoils, etc., but due to the unreliable embolization effect and high recanalization rate, they are only used for embolization before surgery and cannot be used as Permanent embolism. At present, the liquid embolic agent widely used clinically is n-butyl cyanoacrylate (NBCA), which can rapidly polymerize after contacting with blood, thereby achieving the effect of permanent embolism. However, due to its adhesiveness, it has high re...

Claims

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Application Information

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IPC IPC(8): C08F293/00A61K47/32A61L31/04A61L31/14C08F220/54C08F220/28
Inventor 刘文广代凤英赵晓丽陈光
Owner TIANJIN UNIV
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