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Hydroxyl compound terminal modified functional group and method for modifying hydroxyl compound by using hydroxyl compound terminal modified functional group

A hydroxyl compound and terminal modification technology, applied in the field of polymer materials, can solve the problems of product stability and performance, storage cycle impact, high pKa of preparation process, lack of unified and effective means, etc.

Pending Publication Date: 2021-12-24
UNIV OF SCI & TECH OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Currently commonly used terminal amino-modified polyethylene glycol, due to its preparation process and the high pKa of the amino group, has a great impact on the stability and storage period of the product
And the method of commercialized functionalized polyethylene glycol is various at present, lacks a unified and effective means

Method used

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  • Hydroxyl compound terminal modified functional group and method for modifying hydroxyl compound by using hydroxyl compound terminal modified functional group
  • Hydroxyl compound terminal modified functional group and method for modifying hydroxyl compound by using hydroxyl compound terminal modified functional group
  • Hydroxyl compound terminal modified functional group and method for modifying hydroxyl compound by using hydroxyl compound terminal modified functional group

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0069] Example 1: Preparation method of the acid benzymonyl moisture molecule of benzyloxycarbonyl-protected.

[0070]

[0071] Compound 1 (5 g, 175.4 mmol) is dissolved in 100 ml of tetrahydrofuran, an ice bath, add anhydrous triethylamine (2.66 g, 263 mmol), adding azurizophosphate diphenyl ester (DPPA), an ice bath After stirring for 30 minutes, it was stirred at room temperature for 2 h. Carnation solvent, column chromatography (5 / 1, volume ratio) of petroleum ether / ethyl acetate, to obtain product 2 (3.5 g, yield 65%).

Embodiment 2

[0072] Example 2: a method of functionalized benzoxyl oxycarbonyl-protected benzylamine in a hydroxyl terminal having a polyethylene glycol monomethyl ether (n of approximately 45) having a molecular weight of 2000.

[0073]

[0074] Polyethylene glycol monomethyl ether (2.0 g, 1 mmol), benzyl oxycarbonyl-protected benzyl oxycarbonyl, and dibutyltin (DBTL) (40 μl) (40 μl) (40 μl) (40 μl) Unequarabone (100 mL), azeotrophone, 30 ml of non-toluene, and at 85 ° C for 6 h. At the end of the reaction, concentrated toluene, 10 ml of tetrahydrofuran dissolved, precipitated into 100 mL of anhydrous ether, repeatedly dissolved - precipitate 3 times, dried to give a white powder (2.10 g, yield, yield 91.0%).

Embodiment 3

[0075] Example 3: a method of functioning benzylamine on a hydroxyl terminal having a polyethylene glycol monomethyl ether (n of approximately 45) having a molecular weight of 2000.

[0076]

[0077] The final product (2.0 g, 0.9 mmol) in Example 2 (2.0 g, 0.9 mmol) was added to 10% PD / C (0.2 g), and 15 ml of toluene is an azeotropic water. 20 ml of anhydrous methanol, nitrogen protection was added, and then resembled as hydrogen, reacted at 25 ° C for 2 hours, and after the solution had a solution of 220 nm, the solvent had a white powder (1.66 g, yield 87%).

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PUM

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Abstract

The invention provides a hydroxyl compound terminal modified functional group and a method for modifying a hydroxyl compound by using the hydroxyl compound terminal modified functional group. Specifically, the modified functional group is a functional group molecule containing acyl azide or a functional group molecule containing isocyanate converted from the functional group molecule. The modified functional group reacts with terminal hydroxyl groups of polyethylene glycol (PEG), polylactic acid (PLA), polycaprolactone (PCL), polycarbonate (PC) or polyethylene glycol terephthalate (PET) compounds with various topological structures, and a terminal functionalized product containing stable carbamate connection is obtained. Compared with hydroxyl esterification or etherification modification which is mostly researched at present, the method disclosed by the invention is thorough in reaction, short in reaction time and high in functionalization rate, the functionalization rate is greater than 99%, and the obtained functionalized product is high in stability.

Description

Technical field [0001] The present invention relates to the field of polymeric materials, and more particularly to a method of modifying a hydroxy compound and a method of modifying a hydroxy compound thereof. Background technique [0002] With the advancement of technology and the continuous improvement of living, people pay more attention to life, which continues to promote the progress and improvement of society. In recent years, the rapid development of polymer materials has enabled polymeric materials to have a wide range of people in various fields in people's lives, and become a very promising material. [0003] Poly (Ethylene Glycol), PEG is a type of nonionic polymer, with high water soluble, good biocompatibility, is approved by the US Food and Drug Administration (FDA) A type of synthetic polymer used in human clinical (Simon R. Corrie et al, Pharmaceutical Research.2016, 33, 2373-2387). The PEG has a hydroxyactive end, which can functionically modify or be attached to...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C269/06C07C271/22C08G65/333
CPCC07C269/06C08G65/33396C07C271/22Y02P20/55
Inventor 刘世勇史声宇
Owner UNIV OF SCI & TECH OF CHINA
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