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Preparation method and application of N-isopropylacrylamide polymer

A technology of azidopropylacrylamide and polymers, which is applied in the field of preparation of azidopropylacrylamide polymers, can solve problems such as restricting applications, and achieve the effect of convenient and simple method and intelligent controllability of LCST

Inactive Publication Date: 2017-07-25
SHENZHEN ELDERLY MEDICAL RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the immobilized response temperature of polyazisopropylacrylamide is 32.8°C, which is lower than the human body temperature, which restricts its application in drug carriers and drug release.

Method used

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  • Preparation method and application of N-isopropylacrylamide polymer
  • Preparation method and application of N-isopropylacrylamide polymer
  • Preparation method and application of N-isopropylacrylamide polymer

Examples

Experimental program
Comparison scheme
Effect test

experiment example 1

[0026] Take the molar ratio of azido-β-cyclodextrin and monomer N-isopropylacrylamide as 1:50, and monomer N-isopropylacrylamide, azido-β-cyclodextrin, propyne, Ligands Me6TREN and cuprous bromide were dissolved in DMF solution, after repeated freeze-drying-pumping-thawing treatment, the oxygen in the solution was removed, then the mixed solution was put into a safety bottle, and the initiator 2-bromopropionic acid The benzyl ester is poured into a safety bottle under the protection of nitrogen to initiate polymerization, and reacted at 60°C for two days under the protection of nitrogen to obtain a polymer, which is then dialyzed and freeze-dried to obtain the finished product.

[0027] The ratio of monomeric N-isopropylacrylamide to azido-β-cyclodextrin was about 47:1 by NMR analysis. 1 H NMR (500MHz,D 2 O): δ4.04-3.50(m,42H,CD and 47H,NIPAM),7.5-8.5(m,6H,dansyl),5.12-5.02(m,7H,CD),2.20-0.80(m,423H, NIPAM).

[0028] Its LCST is 35 degrees Celsius.

experiment example 2

[0030] The molar ratio of azido-β-cyclodextrin and monomer N-isopropylacrylamide is 1:100, and the monomer N-isopropylacrylamide, azido-β-cyclodextrin, propargyl, Ligands Me6TREN and cuprous bromide were dissolved in DMF solution, after repeated freeze-drying-pumping-thawing treatment, the oxygen in the solution was removed, then the mixed solution was put into a safety bottle, and the initiator 2-bromopropionic acid The benzyl ester is poured into a safety bottle under the protection of nitrogen to initiate polymerization, and reacted at 60°C for two days under the protection of nitrogen to obtain a polymer, which is then dialyzed and freeze-dried to obtain the finished product.

[0031] The ratio of monomeric N-isopropylacrylamide to azido-β-cyclodextrin was about 102:1 by NMR analysis. 1 H NMR (500MHz,D 2 O): δ4.04-3.50 (m, 42H, CD and 102H, NIPAM), 5.12-5.02 (m, 7H, CD), 2.20-0.80 (m, 918H, NIPAM).

[0032] Its LCST is 37 degrees Celsius.

experiment example 3

[0034] The molar ratio of azido-β-cyclodextrin and monomer N-isopropylacrylamide is 1:150, and the monomer N-isopropylacrylamide, azido-β-cyclodextrin, propargyl, Ligands Me6TREN and cuprous bromide were dissolved in DMF solution, after repeated freeze-drying-pumping-thawing treatment, the oxygen in the solution was removed, then the mixed solution was put into a safety bottle, and the initiator 2-bromopropionic acid The benzyl ester is poured into a safety bottle under the protection of nitrogen to initiate polymerization, and reacted at 60°C for two days under the protection of nitrogen to obtain a polymer, which is then dialyzed and freeze-dried to obtain the finished product.

[0035] The ratio of monomeric N-isopropylacrylamide to azido-β-cyclodextrin was about 150:1 by NMR analysis. 1 H NMR (500MHz,D 2 O): δ4.04-3.50(m,42H,CD and 150H,NIPAM),7.5-8.5(m,6H,dansyl),5.12-5.02(m,7H,CD),2.20-0.80(m,1350H, NIPAM).

[0036] Its LCST is 40 degrees Celsius.

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Abstract

The invention discloses a preparation method and application of a N-isopropylacrylamide polymer, azido beta-cyclodextrin is first prepared from beta-cyclodextrin, then an atom transfer radical polymerization (ATRP) and click chemistry one-pot reaction method are used, monomer N-Isopropyl acrylamide, the azido beta-cyclodextrin, propargyl ene, ligand Me6TREN and cuprous bromide are dissolved in a DMF solution, the solution is frozen for a plurality of times for oxygen removal, 2-Bromopropionic acid benzyl ester is added into the solution for initiation of polymerization under the protection of nitrogen, and the required polymer is obtained by stirring for 48 hours at temperature of 60 DEG C. Compared with the prior art, the LCST (lower critical solution temperature) of the polymer is intelligently controlled by adjustment of the proportion of the beta-cyclodextrin and the N-Isopropylacrylamide, functional molecules are added, the method is simple and convenient, and meanwhile by introducing of the cyclodextrin, the biocompatibility of the polymer is improved, and the biological toxicity is reduced.

Description

technical field [0001] The invention relates to polymer nitrogen isopropylacrylamide, in particular to a preparation method and application of nitrogen isopropylacrylamide polymer. Background technique [0002] The phase transition temperature of N-isopropylacrylamide polymer is basically not affected by the molecular weight and concentration of the polymer. The reason why it has LCST characteristics is mainly because there is an amide bond -CONH- which acts as a hydrophilic function on its monomer molecule. , and the hydrophobic isopropyl-CH(CH3) 2 , when the temperature is lower than the LCST, the amide bond in the molecule can form a good hydrogen bond with water, so that the whole polymer dissolves in the aqueous solution and appears clear. When the temperature rises above the LCST temperature, the hydrophilic group amide in the molecule The hydrogen bond between the bond and water is destroyed, so that the hydrophobic part of the isopropyl group in the whole polymer pl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F251/00C08F220/54C08B37/16A61K47/69
CPCC08F251/00C08B37/0012C08F220/54
Inventor 王亮吴正治刘俊秋
Owner SHENZHEN ELDERLY MEDICAL RES INST
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