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Block copolymer and preparation method thereof and hydrogel and preparation method thereof

A technology of block copolymer and hydrogel, which is applied in the field of block copolymer, its preparation, hydrogel and its preparation, can solve the problem that it is difficult to realize the reversible conversion of gel into solution state, non-degradable, polymerized monomer Toxicity and other issues, to achieve the effect of good biodegradability, good fluidity, good biocompatibility

Active Publication Date: 2016-03-23
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

However, there are still many limitations in the injectable temperature-sensitive hydrogels that are currently being studied internationally.
For example, Yu-LingCheng of the University of Toronto in Canada reported a polyethylene glycol-poly(N-isopropylacryloyl) (PEG-PNIPAAm) block copolymer hydrogel in 2001, which has reversible temperature-sensitive properties. , but this temperature-sensitive hydrogel based on PNIPAAm cannot be degraded in vivo, and its polymerized monomers have side effects such as toxicity, tumorigenicity, and teratogenicity, so the application of such materials in vivo is limited.
In addit

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  • Block copolymer and preparation method thereof and hydrogel and preparation method thereof
  • Block copolymer and preparation method thereof and hydrogel and preparation method thereof
  • Block copolymer and preparation method thereof and hydrogel and preparation method thereof

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preparation example Construction

[0043] The application also provides a kind of preparation method of block copolymer, comprises the following steps:

[0044] One of the end-aminated polyethylene glycol monomethyl ether with formula (IV) structure and the end-amination polyethylene glycol with formula (V) structure and γ-ethoxydiethylene glycol- L-glutamate-N-carboxylic acid internal anhydride is polymerized to obtain a block copolymer;

[0045]

[0046] Among them, 10≤m≤227; 10≤n≤226.

[0047] According to the present invention, in order to make the polyethylene glycol monomethyl ether in the block polymer and one of the polyethylene glycol and the γ-ethoxydiethylene glycol-L-glutamic acid Ester-N-carboxylic acid internal anhydride reaction is sufficient, and the preparation process of described block copolymer is specifically:

[0048] One of the aminated polyethylene glycol monomethyl ether having the structure of formula (IV) and the aminated polyethylene glycol having the structure of formula (V) is d...

Embodiment 1

[0087] Preparation of γ-Ethoxydiethylene Glycol-L-Glutamate-N-Carboxylidene Anhydride:

[0088] Mix and stir 30gL-glutamic acid and 120ml diethylene glycol ethyl ether, and add 18ml concentrated sulfuric acid dropwise thereto under stirring conditions, in the presence of concentrated sulfuric acid and stirring conditions, L-glutamic acid and diethylene glycol Ether was esterified, and the reaction time was 24h. After completion of the reaction, neutralize the resulting reaction solution with a mixed solution of 97ml triethylamine and 300ml isopropanol, then centrifuge, recrystallize and dry the resulting mixed solution to obtain γ-ethoxydiethylene glycol-L- Glutamate, the yield was 46.6%.

[0089] Take 20 g of the obtained γ-ethoxydiethylene glycol-L-glutamate and put it into 150 ml of tetrahydrofuran, slowly add 11 g of bis(trichloromethyl)carbonate, the reaction temperature is 50°C, and the reaction time is preferably 0.5 h. After the reaction, the reaction solution was p...

Embodiment 2

[0091] Azeotrope 1.5 g of aminated polyethylene glycol monomethyl ether with a number average molecular weight of 750 and 60 mL of anhydrous toluene at 130 ° C for 2 h to remove water, then drain the remaining toluene under reduced pressure, and dissolve the obtained solid in In 20 mL of dry N,N-dimethylformamide, the first solution was obtained; 4.05 g of γ-ethoxydiethylene glycol-L-glutamate-N-carboxylate anhydride was dissolved in 40 mL of dry In N,N-dimethylformamide, the second solution was obtained; in a nitrogen atmosphere, the first solution was mixed with the second solution, and the reaction was stirred and reacted at 40°C for 72h under nitrogen protection conditions. After the reaction was completed, use Diethyl ether was settled, suction filtered, and dried to obtain a polyethylene glycol monomethyl ether-poly(γ-ethoxydiethylene glycol-L-glutamate) block copolymer having a structure of formula (VI).

[0092] The block copolymer obtained above is carried out nuclear...

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Abstract

The invention provides a block copolymer and a preparation method thereof and hydrogel and a preparation method thereof. The block copolymer comprises a first block with the structure shown in a formula (I) or a formula (II) and a second block with the structure shown in a formula (III). The forming process of the hydrogel formed by block copolymers is reversible, and the adjusting means of the gel forming behavior of temperature-sensitive type hydrogel is expanded; meanwhile, the hydrogel can be degraded in vivo, degradation products are amino acid and polyethylene glycol which can be directly discharged out of a body through kidneys, and damage to human bodies does not exist; in addition, the phase-transition temperature of the formed temperature-sensitive type hydrogel can be adjusted by adjusting the length of the second block chain segment, and therefore further application of the temperature-sensitive type hydrogel is facilitated.

Description

technical field [0001] The invention relates to the technical field of polymer materials, in particular to a block copolymer, a preparation method thereof, and a hydrogel and a preparation method thereof. Background technique [0002] Hydrogels are a class of polymers with a cross-linked network structure capable of absorbing and retaining large amounts of water. Temperature-sensitive hydrogels are a class of polymer materials that are sensitive to temperature changes. If the phase transition temperature of the hydrogels can be controlled to be close to the body temperature of the human body, the temperature-sensitive hydrogels can be prepared into biomedical applications. Injectable hydrogel. For example, the temperature-sensitive injectable hydrogel exists in a solution state when it is lower than the body temperature, and can be well mixed with drugs, peptides, proteins, cells or biologically active substances; when injected into the human body, due to the temperature C...

Claims

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Application Information

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IPC IPC(8): C08G69/40C08J3/075
CPCC08G69/40C08J3/075C08J2377/02
Inventor 贺超良权奋丽张瑜陈莉陈学思
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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