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Dendrimer-like polymer and synthetic method and application thereof

A synthetic method and polymer technology, applied in the field of dendritic polymers, can solve the problems of low density of grafting points, complicated steps, limiting the application performance of dendritic polymers, etc., and achieve the effect of high graft density

Active Publication Date: 2019-04-05
FUDAN UNIV
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

In the existing synthetic methods of dendrimer-like polymers, the formation of graft points at the end of polymer molecular chains mostly needs to go through the process of protection and deprotection. Target polymer yield is low
(J. Six, Y. Gnanou. Macromol. Symp. ,1995, 95, 137−150; V.Percec, B.Barboiu, C.Grigoras, T.K.Bera. J. Am. Chem. soc ., 2003, 125, 6503−6516; A. Matsuo, T. Watanabe, A. Hirao. Macromolecules ,2004, 37, 6283−6290; C. A. Bell, Z. Jia, J. Kulis, M. J. Monteiro. Macromolecules ,2011, 44, 4814−4827; H. Zhang, J. He, C. Zhang, Z. Ju, J. Li, Y. Yang. Macromolecules , 2012, 45(2), 828−841; G. Polymeropoulos, G. Zapsas, K. Ntetsikas, P. Bilalis, Y. Gnanou, N. Hadjichristidis. Macromolecules , 2017,90, 1253−1290) Therefore, these currently reported methods are not conducive to the large-scale synthesis of dendrimers
In addition, the activity of the grafting sites selected by many synthetic methods is often low, which is not conducive to the synthesis of dendritic polymers with multi-component graft chains, thus limiting the application performance of dendritic polymers and their application in industry. Application prospects in production (H. Zhang, J. Zhu, J. He,; F. Qiu, H. Zhang, Y. Yang, H. Lee, T. Chang. Polym. Chem. , 2013, 4,830−839)

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0034] Embodiment 1: synthetic VSt

[0035] VSt can be generated by coupling 4-chloromethylstyrene (CMS) with allylmagnesium chloride. Under the protection of argon, add 200 mL THF solution (1.0 mol / L) of allylmagnesium bromide into the four-neck flask equipped with a constant pressure dropping funnel, and then add 23 mL CMS (0.16 mol) and 50 mL THF. After the reaction system was cooled to 0 °C with ice-water mixture, the THF solution of CMS was slowly dropped into the flask, and the reaction system was raised to room temperature, and magnetically stirred for 12 h under the protection of argon. After the reaction, slowly add 20 mL of saturated ammonium chloride (NH 4 Cl) solution. The reaction solution was poured into a separatory funnel, the product was extracted with ether, and saturated NH 4 Cl solution was washed three times. Finally, put VSt and appropriate amount of CaH 2 Add it into a round bottom flask, stir at room temperature for 12 h, then distill it off with ...

Embodiment 2

[0036] Embodiment 2: Synthesis of three generations of dendrimers (G3- g -SiCl)

[0037] In a vacuum system, use 100 mL of n -BuLi decontaminated toluene and 50 mL n -BuLi-purified THF was flash evaporated into the anion reaction vial. Fill the reaction bottle with dry argon until the pressure in the bottle is slightly higher than atmospheric pressure, and add 2.8 mL VSt (15.9 mmol) into the bottle with a syringe, cool the reaction solution to -45°C with an acetonitrile / liquid nitrogen bath, and then add to the reaction bottle. Add 1.5 mL to the solution s -BuLi in n-hexane solution, the reaction solution immediately turns orange. Under the condition of -45°C, magnetically stir for 30 minutes to obtain the active anion chain PVStLi. Add 16.8 mL of styrene (146.2 mmol) that had been removed with dibutylmagnesium to the reaction solution, and the color of the reaction solution darkened slightly. - At 45°C, magnetically stirred for 1 h to obtain the active anion chain PVSt-...

Embodiment 3

[0040] Example 3: Synthesis of four generations of dendritic polystyrene (G4-PS)

[0041] In a vacuum system, the n - The THF from which BuLi was removed and the St from which Dibutyl Magnesium was removed were flashed into the reaction bottle, and dry argon was filled into the reaction bottle until the pressure in the bottle was slightly higher than the atmospheric pressure. After the reaction system cools down to -78°C, add s -BuLi, the solution immediately becomes orange-red. Under the condition of -78°C, magnetically stirred for 1 h to obtain the active anion chain PSLi. A small amount of reaction liquid was taken and terminated with degassed methanol, and the resulting polymer was used to analyze the degree of polymerization of grafted PS. Add G3- to the THF solution of PSLi g-SiCl in toluene solution, and gradually warmed to -45 °C, magnetically stirred for 2 h, and the excess PSLi was terminated with degassed methanol. With methanol as a poor solvent and toluene as...

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Abstract

The invention belongs to the technical field of dendrimer-like polymers and particularly relates to a dendrimer-like polymer and a synthetic method and application thereof. The dendrimer-like polymerwith multiple components is prepared by: using 4-(vinylphenyl)-1-butene as a repeat unit to construct an outer chain segment of the polymer herein; using sec-butyllithium to trigger VSt polymerization; subjecting double bonds and dimethylchlorosilane to hydrosilylation under the action of Karstedt's catalyst to generate high-activity grafting sites; subjecting the high-activity grafting sites to coupling reaction with various active anionic chains. In addition, the quantity of the grafting sites may also be controlled by adjusting the polymerization degree of the PVSt chain segment to preparethe dendrimer-like polymer with high grafting density. The dendrimer-like polymer herein has a good application prospect in terms of reducing polymer processing viscosity. In addition, G4-P2VP is dissoluble in trifluoroacetic acid solution; pyridine groups in the molecules have good coordination capacity; the dendrimer-like polymer has a good application prospect in polymer micelles.

Description

technical field [0001] The invention belongs to the technical field of dendrimers, and in particular relates to a dendrimer and its synthesis method and application. Background technique [0002] Dendritic polymers have many unique properties, such as: high density, low intrinsic viscosity, large cavity inside the molecule, and so on. These unique properties endow this type of polymer with broad application prospects, for example, it can be used as a drug-localized sustained-release agent, a rheology modifier for polymer processing, and a catalyst carrier, etc., so the synthesis of dendrimers has always been much attention. [0003] Since Yves Gnanou first reported the synthesis of dendritic polyethylene oxide in 1995, some synthetic methods of dendritic polymers have been reported. In the existing synthetic methods of dendrimer-like polymers, the formation of graft points at the end of polymer molecular chains mostly needs to go through the process of protection and depro...

Claims

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Application Information

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IPC IPC(8): C08G83/00
CPCC08G83/003
Inventor 何军坡郑轲曲程科
Owner FUDAN UNIV
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