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Alkoxy ether thermosensitive chiral polymer nano-microspheres and preparation method thereof

A technology of nano-microspheres and alkoxy ethers, which is applied in the field of alkoxy-ether thermosensitive chiral polymer nano-microspheres and its preparation, can solve the problems of stabilizing single-chiral nano-microspheres, which have not been reported, and achieve excellent results. Temperature-sensitive behavior, stable and single conformation, and good dispersion

Inactive Publication Date: 2016-08-31
SHANGHAI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] At present, some progress has been made in the research work on nano-microspheres, but there are few reports on stable and single chiral nano-microspheres, and the preparation of chiral nano-microspheres and the control of the particle size of nano-microspheres through their temperature-sensitive properties job not yet reported

Method used

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  • Alkoxy ether thermosensitive chiral polymer nano-microspheres and preparation method thereof
  • Alkoxy ether thermosensitive chiral polymer nano-microspheres and preparation method thereof
  • Alkoxy ether thermosensitive chiral polymer nano-microspheres and preparation method thereof

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preparation example Construction

[0028] For the preparation method of the first-generation alkoxyether dendron, please refer to the literature Li, W.; Zhang, A.; Schlüter, A. D. Chem. Commun. 2008, 5523 and Yan J T; Liu K; Wu D L; Chen F; Wu P Y; Zhang A. Chem. Asian J. , 2011, 6, Synthesis of 3260.

[0029] For the preparation method of p-alkynylbenzaldehyde, please refer to the literature Zhang, Y; Gao, K; Zhao, Z; Yue, D; Hu, Y; Masuda T. J. Polym. Science. Part A: Polym. Chem. , 2013, 51(24), 5248 Synthesis.

[0030] For the preparation method of p-alkynylbenzoic acid, please refer to literature E, Yashima; T, Matsushima; and Y, Okamoto. J. Am. Chem. Soc., 1997, 119 (27), 6345 Synthesis.

[0031] The preparation method of pentafluorophenol active ester of p-alkynylbenzoic acid refers to the literature B. Z. Tang, et al. Macromolrcules, 2011, 6724.

[0032] The preparation method of PA-N-ALA-G1-Et refers to the patent Zhang Afang. Polyphenylene vinylene derivatives with reversible regulation of tempe...

Embodiment 1

[0033] Embodiment one: concrete steps are:

[0034] 1. Synthesis of Polymer P(PA-N-ALA-G1-Et-co-PA-CHO)

[0035] Weigh p-alkynylbenzaldehyde and the alkoxyether first-generation dendritic phenylacetylene macromonomer containing chiral inducing groups at a molar ratio of 5:1 and dissolve them in a small amount of dry tetrahydrofuran, slowly add 1 / 50 equivalents of [Rd(nbd)Cl] aged and added dropwise with 1 drop of triethylamine 2 THF solution, the reaction was stirred at room temperature for 5 hours until the reaction was complete. After the THF was spin-dried, DCM was used to purify the crude product by column chromatography to obtain the target copolymer. attached by figure 2 1 HNMR at room temperature and high temperature (DMSO, 25ºC, 80ºC): By integrating the aldehyde group and comparing the ratio of the hydrogen of the methylene group on the side group of the methine group and the first-generation alkoxyether side group of the amino acid, and the methyl group of the...

Embodiment 2

[0039] The size of the copolymer and the polymer nanospheres in aqueous solution were characterized by dynamic light scattering. as attached image 3 As shown, at room temperature (lower than 27°C), the size radius of the copolymer is about 10nm, and the dispersion is wide. When the temperature reaches 27°C, the polymer begins to dehydrate, followed by chain segment collapse and aggregation, forming aggregates with a narrow distribution of about 100nm. attached Figure 4 For the prepared polymer nanospheres, after diluting from 0.05mg / ml to 0.025mg / ml, 0.01mg / ml, dynamic light scattering shows that it basically maintains about 100nm. Therefore, it was proved that the polymer nanospheres were successfully prepared.

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Abstract

The invention relates to alkoxy ether thermosensitive chiral polymer nano-microspheres and a preparation method thereof. The nano-microspheres are prepared by carrying out copolymerization reaction on alkoxy ether dendronized macromonomer with chiral induction primitive and p-alkynyl benzaldehyde to obtain a copolymer, and cross-linking the copolymer by using adipic dihydrazide as a cross-linking agent to form the alkoxy ether chiral polymer nano-microspheres, wherein the mol ratio of the aldehyde group in the copolymer to the cross-linking agent is 2:1. The nano-microspheres have good dispersibility in water solution and excellent thermosensitive behavior, and by adjusting temperature, concentration and molecular weight, chiral nano-microspheres with different particle sizes can be prepared. Simultaneously, compared with variable helical conformation of copolymers, the conformation of the obtained nano-microspheres is stable and single. The nano-microspheres are constructed by cross-linking a dynamic bond with a thermosensitive polymer, chiral transference of the chiral induction primitive provides a theoretical basis, and the nano-microspheres are of important significance in fields of realizing selectivity, identification or function control of some protein and amino acid, medicine release, envelop and the like.

Description

technical field [0001] The invention relates to a stable single-chiral nano-microsphere and a preparation method thereof, in particular to an alkoxy ether-based temperature-sensitive chiral polymer nano-microsphere and a preparation method thereof. Background technique [0002] The preparation and application of smart polymer nanospheres have made breakthroughs in the past ten years, and the preparation methods and systems have become increasingly perfect, making them of great research value in new functional materials and special materials. Smart polymers, such as temperature-sensitive polymers, usually have a minimum critical solution temperature. When the temperature of the external environment is lower than its minimum critical solution temperature, it is well-dissolved and transparent in water; when the temperature rises to the minimum critical solution temperature At temperatures above and above, the polymer segments begin to dehydrate, collapse, aggregate, and the sol...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F238/00C08F8/30
CPCC08F8/30C08F238/00
Inventor 张阿方赵元博张培楠徐刚祝润朗李文肖莉
Owner SHANGHAI UNIV
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