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Poly L-glutamic acid-poly N-isopropylacrylamide graft copolymer and preparation method thereof

A technology of isopropyl acrylamide and graft copolymer, which is applied in the field of poly-L-glutamic acid-poly-N-isopropyl acrylamide graft copolymer and its preparation, can solve the problem of unseen copolymer, polyamino acid Problems such as the lack of reports on co-polymerization

Inactive Publication Date: 2007-10-24
CHANGZHOU INST OF ENERGY STORAGE MATERIALS &DEVICES
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, so far, there are few reports on the copolymerization of poly-N-isopropylacrylamide and polyamino acids with carboxyl side chains.
Macromol.RapidCommun.Vol.18, p.361-369 (1997) only reported that γ-benzyl-L-glutamic acid-N-carboxylic acid anhydride (BLG- NCA) ring-opening polymerization to obtain a poly-N-isopropylacrylamide-poly-γ-benzyl-L-glutamate diblock copolymer with only temperature response, and only studied its micellar behavior, while There is no further research on the preparation of copolymers with dual sensitivity to temperature and pH

Method used

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  • Poly L-glutamic acid-poly N-isopropylacrylamide graft copolymer and preparation method thereof
  • Poly L-glutamic acid-poly N-isopropylacrylamide graft copolymer and preparation method thereof
  • Poly L-glutamic acid-poly N-isopropylacrylamide graft copolymer and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0054] Example 1: Preparation of poly-L-glutamic acid homopolymers with different molecular weights.

[0055] (1) Weigh 5 parts of 0.076mol of γ-benzyl-L-glutamate-N-carboxylic acid anhydride (BLG-NCA) monomer into 5 dry reaction flasks, add 400ml of dry dioxane respectively The ring dissolves the monomer. Under vigorous stirring, 0.015, 0.0076, 0.0038, 0.0030 and 0.00076 mol of triethylamine were added, and the solution was allowed to stand at room temperature for 72 hours. The product was settled with ethanol, filtered, washed, and vacuum-dried at room temperature for 24 hours to obtain five kinds of polyγ-benzyl-L-glutamate homopolymers with different molecular weights. The yield is 81-92%.

[0056] (2) 5 kinds of poly-γ-benzyl-L-glutamate obtained in (1) are respectively weighed 10g, dissolved in 150ml dichloroacetic acid respectively, and 30ml hydrogen bromide content is added respectively at room temperature and is 33wt% Hydrogen bromide / glacial acetic acid solution (...

Embodiment 2

[0059] Example 2: Preparation of poly-N-isopropylacrylamide homopolymers with different molecular weights and one terminal being an amino terminal.

[0060]Weigh 4 parts of 0.2mol of N-isopropylacrylamide and 0.002mol of azobisisobutyronitrile, add them to 4 reaction ampoules respectively, then add 0.003, 0.006, 0.012 and 0.02mol of Mercaptoethylamine. After dissolving with 40ml of methanol respectively, the gas in the bottle was removed through 3 freeze-vacuum-melt cycles, and the ampoule was sealed. The solution was stirred at 50, 60, 60 and 80°C for 24 hours, and the product was settled with excess ether, filtered, washed, and vacuum-dried to obtain poly-N-isopropylacrylamide homopolymers of different molecular weights with one end being an amino terminal. The results are shown in Table 2.

[0061] Numbering

[0062] In the above table, A / I / T refers to the molar ratio of N-isopropylacrylamide monomer / azobisisobutyronitrile / mercaptoethylamine; DP (PNIPAM) is the...

Embodiment 3

[0063] Example 3: Poly L-glutamic acid-poly N-isopropylacrylamide graft copolymer was synthesized by using an oil-soluble coupling agent and N-hydroxysuccinimide (NHS) to activate the carboxyl group.

[0064] Add 0.2g of poly-L-glutamic acid (viscosity-average molecular weight 27800Da, DP=215) and N-hydroxysuccinimide (NHS) into reaction ampoules with different numbers, and the amount of N-hydroxysuccinimide See Table 3 for the molar ratio of the amino-terminal poly-N-isopropylacrylamide that is expected to be added. Add 10ml of N, N-dimethylformamide to gradually dissolve the solid, cool the solution to 0°C, and add N-hydroxyl Dicyclohexylcarbodiimide in an equimolar amount of succinimide was stirred at room temperature for 24 hours. Then, 0.25 g of poly-N-isopropylacrylamide (number-average molecular weight: 1800 Da, DP=15) with one terminal being an amino terminal was added, and the reaction was continued to stir at room temperature for 72 hours. After the reaction, filter...

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Abstract

The invention discloses a two-block copolymer of poly-N-isopropyl acrylamide-polyamino acid and making method, which is characterized by the following: the number average molecular weight of poly-N-isopropyl acrylamide-polyamino acid is 1000-10000; the polyamino acid is poly-L-glutamic acid or poly-L-aspartic acid with number average molecular weight at 1000-30000; the molar percentage of amino acid carbobenzoxy is 0-90%; the invention uses hydrogen bromide or reducing method to strip benzyl through catalyzing and hydrogenating to obtain the product, which possesses double response for temperature and pH value in the solution; the copolymer can be biological decomposed to be discharged out of body through kidney directly, which can be carrier of target drug release and injectable intellectual response aquagel.

Description

technical field [0001] The present invention relates to poly-L-glutamic acid-poly-N-isopropylacrylamide graft copolymer and its preparation method, in particular to poly-L-glutamic acid-poly-N-isopropylacrylamide graft copolymer and photosensitive Cross-linked poly-L-glutamic acid-poly-N-isopropylacrylamide graft copolymer and its preparation method. Background technique [0002] Intelligent water-soluble polymer materials can suddenly produce reversible physical or chemical responses to external stimuli (such as changes in temperature, pH, solution ionic strength, and electric field strength), and their shape, volume, and water absorption will change dramatically. Therefore, this kind of polymer materials has very important application value in medicine, biotechnology, industry and environment. Among them, water-soluble polymer materials that are sensitive to temperature and pH changes are particularly widely used in the fields of biomedicine and pharmacy, such as temperat...

Claims

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Application Information

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IPC IPC(8): C08G81/02C08G69/08C08G69/48C08F220/56
Inventor 庄秀丽贺超良陈学思郭召军赵长稳景遐斌
Owner CHANGZHOU INST OF ENERGY STORAGE MATERIALS &DEVICES
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