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Alkynyl hydroxypropyl cellulose and preparation method and application of temperature-sensitive hydrogel of alkynyl hydroxypropyl cellulose

A temperature-sensitive hydrogel, alkynyl hydroxypropyl technology, applied in the field of biomedical functional materials, can solve the problems of poor temperature sensitivity of hydrogel, poor mechanical strength of biocompatibility, poor automatic degradation, etc.

Active Publication Date: 2012-12-19
GUANGZHOU CHEM CO LTD CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, currently, the hydrogels prepared by the click chemical reaction of azido and alkyne groups have poor temperature sensitivity, slow response speed, poor biocompatibility and mechanical strength; in addition, most of the hydrogels prepared by click chemical reaction Hydrogels also have poor self-degradability under body fluid conditions. In addition to microgel particles, bulk hydrogels prepared by click chemistry must go through a surgical implantation-removal process to achieve their purpose. Therefore, the current click chemistry There are still many obstacles to the application of the prepared hydrogel in animals

Method used

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  • Alkynyl hydroxypropyl cellulose and preparation method and application of temperature-sensitive hydrogel of alkynyl hydroxypropyl cellulose
  • Alkynyl hydroxypropyl cellulose and preparation method and application of temperature-sensitive hydrogel of alkynyl hydroxypropyl cellulose
  • Alkynyl hydroxypropyl cellulose and preparation method and application of temperature-sensitive hydrogel of alkynyl hydroxypropyl cellulose

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0074] (1) Add 8gε-caprolactone, 5g hydroxyethyl methacrylate, 0.1g stannous octoate and 0.05g p-hydroxyanisole into the round bottom flask, pump the reactor to vacuum, seal it, and react at 110°C 3h, the product 1 was obtained.

[0075] (2) Dissolve the product 1 obtained in step (1) in 5ml tetrahydrofuran (analytically pure) to make a solution, pour this solution into 50ml methanol to precipitate a white precipitate, repeat the dissolution-precipitation process 4 times, and place the precipitate in vacuum at room temperature Product 2 was obtained after drying for 12 h.

[0076] (3) Dissolve the product 2 obtained in step (2) and 1ml of triethylamine in 15ml of dichloromethane, add 2g of dibromoisobutyryl bromide dropwise at -15°C, and react at 30°C after the addition is complete After 10 h, wash with 100 ml of saturated sodium carbonate solution for 4 times, and then with 100 ml of deionized water for 4 times, then pour the reactant into 250 ml of petroleum ether for 90 mi...

Embodiment 2

[0082] (1) Add 12gε-caprolactone, 2g hydroxyethyl methacrylate, 0.1g stannous octoate and 0.08g p-hydroxyanisole into the reactor, pump the reactor to vacuum, seal it at 130°C and react for 5h to obtain Product 1.

[0083] (2) Dissolve the product 1 obtained in step (1) in 10ml tetrahydrofuran (analytically pure) to obtain a solution, pour this solution into 100ml methanol to precipitate a white precipitate, repeat this dissolution-precipitation process 4 times, and place the precipitate at room temperature Product 2 was obtained after vacuum drying for 24 h.

[0084] (3) Dissolve the product 2 and 3ml of triethylamine obtained in step (2) in 5ml of dichloromethane, add 2.5g of dibromoisobutyryl bromide dropwise at -20°C, after the addition is complete, at 20°C After reacting for 6 hours, wash twice with 50ml saturated sodium carbonate solution, then wash twice with 50ml deionized water, then pour the reactant into 150ml petroleum ether for 30min, and then precipitate the pro...

Embodiment 3

[0090] (1) Add 10gε-caprolactone, 2g hydroxyethyl methacrylate, 0.05g stannous octoate and 0.05g p-hydroxyanisole into the reactor, pump the reactor to vacuum, seal it, and react at 120°C for 3.5 h to give product 1.

[0091] (2) Dissolve the product 1 obtained in step (1) in 5ml tetrahydrofuran (analytically pure), pour this solution into 100ml methanol to precipitate a white precipitate, repeat the dissolution-precipitation process twice, and place the precipitate at room temperature under vacuum Product 2 was obtained after drying for 20 h.

[0092] (3) Dissolve the product 2 and 3ml of triethylamine obtained in step (2) in 15ml of dichloromethane, add 1ml of dibromoisobutyryl bromide dropwise at -20°C, and react at 20°C after the addition is complete 6h, then washed twice with 50ml of saturated sodium carbonate solution, then washed twice with 50ml of deionized water, then poured the reactant into 150ml of petroleum ether for 30min to precipitate product 3.

[0093] (4) ...

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Abstract

The invention discloses alkynyl hydroxypropyl cellulose and a preparation method and an application of a temperature-sensitive hydrogel of the alkynyl hydroxypropyl cellulose. In the invention, natural biology-based high-polymer hydroxypropyl cellulose is provided firstly, and is introduced into synthesis of a temperature-sensitive hydrogel material. The method for the temperature-sensitive hydrogel comprises the following steps of: (1) preparing azidopolycaprolactone-2-hydroxyethyl methylacrylate; (2) preparing poly(azidopolycaprolactone-2-hydroxyethyl methylacrylate-co-nitroisopropyl acrylamide); (3) preparing alkynyl hydroxypropyl cellulose; and (4) performing a click chemical reaction on the poly(azidopolycaprolactone-2-hydroxyethyl methylacrylate-co-nitroisopropyl acrylamide) and the alkynyl hydroxypropyl cellulose according to a certain proportion to obtain the temperature-sensitive hydrogel finally. The hydrogel provided by the invention has a unique structure and high mechanical strength, is biodegradable, and has a potential application value in the field of biological medicine.

Description

technical field [0001] The invention belongs to the field of biomedical functional materials, and in particular relates to a preparation method and application of alkynyl hydroxypropyl cellulose and a temperature-sensitive hydrogel thereof. Background technique [0002] N-isopropylacrylamide is a common temperature-sensitive monomer, and the polymer prepared from it has a lower critical solution temperature (LCST), which is about 32°C. When the ambient temperature of the polymer is lower than the LCST, the hydrogen bond between the water molecule and the secondary amino group in the N-isopropylacrylamide molecule is strengthened, so that the prepared polymer exhibits a hydrophilic property; when polymerized When the ambient temperature of the substance is higher than the LCST, the hydrogen bond is destroyed, and the hydrophobic effect of the isopropyl group in the N-isopropylacrylamide molecule is dominant, resulting in the prepared polymer showing hydrophobic properties. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B11/08C08G81/00C08F290/06C08G63/91C08G63/08A61K47/34A61K47/38
Inventor 吕满庚苗磊
Owner GUANGZHOU CHEM CO LTD CHINESE ACADEMY OF SCI
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