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Photosensitive amphiphilic copolymer containing thymine and self-assembled micelle thereof

A technology of thymine and copolymers, applied in the field of photosensitive amphiphilic copolymers and self-assembled micelles, which can solve the problems of less reporting of micelles and achieve excellent heat resistance

Active Publication Date: 2015-10-14
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] At present, there are few reports on thymine-containing amphiphilic polymers, and the self-assembled micelles of the polymers are rarely reported.

Method used

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  • Photosensitive amphiphilic copolymer containing thymine and self-assembled micelle thereof
  • Photosensitive amphiphilic copolymer containing thymine and self-assembled micelle thereof
  • Photosensitive amphiphilic copolymer containing thymine and self-assembled micelle thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] A photosensitive amphiphilic copolymer containing thymine and self-assembled micelles thereof, the specific preparation method is as follows:

[0034] (1) Synthesis of 1-(4-vinylbenzyl)thymine (VBT)

[0035] Thymine (6.02g) was dissolved in an aqueous solution (200mL) of potassium hydroxide (2.64g), stirred for 24 hours, freeze-dried, and dried in a vacuum oven at 45°C for 24 hours to obtain thymine potassium salt;

[0036] Take 7.64g (0.0466mol) of thymine potassium salt, 60mg of 2,4-di-tert-butyl-p-methylphenol, 7.64g (0.0544mol) of 4-vinylbenzyl chloride in 106g of anhydrous DMF, and react at 70°C for 24h ; Use a rotary evaporator to remove the solvent at 65°C, add toluene, and filter with suction at about 110°C, keep the filtrate, cool and crystallize, filter with suction, and dry the product in vacuum to obtain pure 1-(4-vinylbenzyl) Thymine (VBT).

[0037] (2) Preparation of amphiphilic copolymer P(St / VBT-alt-MA)

[0038] Weigh 0.816g (0.00785mol) of styrene, 0...

Embodiment 2

[0045] A photosensitive amphiphilic copolymer containing thymine and self-assembled micelles thereof, the specific preparation method is as follows:

[0046] (1) Preparation of amphiphilic copolymer P(St / VBT-alt-MA)

[0047] Weighing styrene 0.539g (0.00518mol), VBT 0.301g (0.00124mol) prepared in Example 1, maleic anhydride 0.613g (0.00626mol), initiator AIBN 0.043g (0.00026mol, by monomer total molar weight 2.0% of THF) in 10 mL of anhydrous THF, stirred at 70°C for 20 h, precipitated in toluene 10 times that of THF, filtered, and dried in vacuum at 30°C, the product was dissolved in THF, precipitated, filtered, dried, and the above steps were repeated Three times, the pure amphiphilic copolymer P(St / VBT-alt-MA) (PSVM2) was obtained. For the NMR characterization of the copolymer see figure 2 (B).

[0048] From figure 2 From the chemical shift δ in (B), it can be seen that the H11 characteristic peak of -NH on VBT appears at the chemical shift δ11.41~11.18ppm, which pro...

Embodiment 3

[0054] A photosensitive amphiphilic copolymer containing thymine and self-assembled micelles thereof, the specific preparation method is as follows:

[0055] (1) Preparation of amphiphilic copolymer P(St / VBT-alt-MA)

[0056] Weigh styrene 0.417g (0.00401mol), VBT 0.610g (0.00252mol) prepared in Example 1, maleic anhydride 0.611g (0.00623mol), initiator AIBN 0.042g (0.00026mol, by monomer total molar weight 2.0%) in 10 mL of anhydrous THF, stirred at 60°C for 24h, precipitated in toluene 10 times that of THF, filtered, and dried in vacuum at 30°C, the product was dissolved in THF, precipitated, filtered, dried, and the above steps were repeated Three times, the pure amphiphilic copolymer P(St / VBT-alt-MA) (PSVM3) was obtained. For the NMR characterization of the copolymer see figure 2 (C).

[0057] From figure 2 From the chemical shift δ in (C), it can be seen that the H11 characteristic peak of -NH on VBT appears at the chemical shift δ11.41~11.18ppm, which proves that VB...

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Abstract

The invention discloses a photosensitive amphiphilic copolymer containing thymine. The photosensitive amphiphilic copolymer P(St / VBT-co-MA) is prepared from 1-(4-vinylbenzyl)thymine (VBT), styrene, maleic anhydride, azodiisobutyronitrile (AIBN) and tetrahydrofuran through a reaction in an oil bath with a temperature of 60 to 70 DEG C for 20 to 24 h and repeated purification with toluene after completion of the reaction, wherein 1-(4-vinylbenzyl)thymine (VBT), styrene and maleic anhydride are used as copolymerization monomer, azodiisobutyronitrile (AIBN) is used as an initiator and tetrahydrofuran is used as a solvent. A micelle can be prepared from the copolymer through self-assembly. The copolymer simultaneously contains a hydrophilic chain segment and a hydrophobic chain segment and can form the micelle in deionized water throughy; a thymine group on the hydrophobic chain segment can undergo photocrosslinking, which enables the copolymer to have photosensitivity; and the self-assembled micelle has good dispersibility, a controllable particle size and photosensitivity and can be used for a sensing coating.

Description

technical field [0001] The present invention relates to the technical field of macromolecular self-assembled micelles, in particular to a kind of comonomer with 1-(4-vinylbenzyl)thymine VBT, styrene and maleic anhydride, which is prepared by free radical polymerization Photosensitive amphiphilic copolymers and their self-assembled micelles. Background technique [0002] Amphiphilic polymers are polymers in which hydrophilic segments and hydrophobic segments are arranged on the same macromolecular chain in a specific way. Its biggest feature is that it can self-assemble under mild conditions to form various effective Ordered nano-microphase structure, such as spherical, rod-like, lamellar, vesicle, large composite micelles formed by small micelles, etc. With the development of polymer chemistry, a series of functionalized amphiphilic copolymers have been designed and synthesized according to individual needs, and various interesting structures have been obtained. Previous r...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F222/08C08F212/08C08F212/14C08J3/02C07D239/54
Inventor 刘敬成谢亚珍林立成王宽刘仁刘晓亚
Owner JIANGNAN UNIV
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