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Perfluor-vinyl-containing amino-allyl formate as well as preparation method and application thereof

A carbamic acid and perfluoroalkenyl technology, which is applied in the field of new polymer monomer containing allyl carbamate containing perfluoroalkenyl carbamate and its preparation, can solve problems such as danger and restrictions, and achieve convenient operation and simple intermediate process Effect

Active Publication Date: 2012-11-14
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Perfluorooctane sulfonic acid (PFOS) and its derivatives, due to their high persistence and accumulation in the environment, are potentially dangerous, so they are strictly restricted in developed countries such as the United States and the European Union

Method used

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  • Perfluor-vinyl-containing amino-allyl formate as well as preparation method and application thereof
  • Perfluor-vinyl-containing amino-allyl formate as well as preparation method and application thereof
  • Perfluor-vinyl-containing amino-allyl formate as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027]Add 1,2-dichloroethane 50mL, toluene-2,4-diisocyanate 17.4g (2,4-TDI, 0.1mol), tetraethyltin 1.9g (0.008mol), 0.5g in a 250mL four-necked flask Hydroquinone was used as a polymerization inhibitor, stirred, and the temperature was raised to 75 ° C, and 5.8 g (0.1 mol) of allyl alcohol was added dropwise. After the addition was completed, TLC was used to detect the reaction process, and the temperature was kept to stir for 4 hours. 53.6 g (0.1 mol) of 2-methoxy-3-perfluorononenyloxypropanol was added dropwise. After the dropwise addition was completed, TLC detection was carried out to track the reaction progress, and the reaction was carried out while maintaining the temperature and stirring for 5 h. After completion of the reaction, the desolvation by distillation under reduced pressure was separated by silica gel column chromatography (V 环己烷 :V 乙酸乙酯 =4:1), after removing the solvent, yellow viscous paste I was obtained 1 (n=9), yield 61.2%, purity 99.7%.

[0028] FT-I...

Embodiment 2

[0032] React according to the method of Example 1, but 2-methoxyl-3-perfluorononenyloxypropanol is changed to 2-methoxyl-3-perfluorohexenyloxypropanol 38.6g (0.1mol), Other conditions are identical with embodiment 1, obtain pale yellow paste I 2 (n=6), yield 65.3%, purity 99.5%.

[0033] 19 F NMRδ(CDCl 3 ): -129.4(t, 3F), -127.4(s, 3F), -121.6(m, 2F), -83.3(s, 2F), -78.1(t, 1F).

Embodiment 3

[0035] Add N,N-dimethylacetamide 50mL, 2,4-TDI 17.4g (0.1mol), tetraphenyltin 4.27g (0.01mol), 0.5g hydroquinone as polymerization inhibitor in 250mL four-neck flask, Stir, raise the temperature to 100°C, add 8.13g (0.14mol) of allyl alcohol dropwise. After the completion of the dropwise addition, TLC detection, follow the reaction progress, keep the temperature and stir the first step for 4h. 75.04 g (0.14 mol) of 2-methoxy-3-perfluorononenyloxypropanol was added dropwise. After the dropwise addition was completed, TLC was detected to track the reaction progress, and the second reaction was stirred for 5 hours while maintaining the temperature. Reaction is completed, and solvent extraction is separated by silica gel column chromatography (V 环己 烷 :V 乙酸乙酯 = 7: 3), the yellow paste I was obtained after removing the solvent 1 (n=9), yield 67.7%, purity 99.5%.

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Abstract

The invention discloses a perfluor-vinyl-containing amino-allyl formate as well as a synthesizing method and an application thereof. The method is carried out according to the following steps of: (1) causing methylbenzene-2,4-diisocyanate shown by a formula (II) and propenol shown by a formula (III) to carry out primary addition reaction in a polar aprotic solvent by taking organotin as a catalyst, continuing the reaction till II substantially disappears, and obtaining a reaction liquid A of an intermediate shown by a formula (IV); and (2) directly adding the reaction liquid A into 2-methoxyl-3-perfluor-vinoxyl propanol shown by a formula (V) to realize secondary addition reaction, obtaining a reaction liquid B after the reaction is finished, and obtaining the perfluor-vinyl-containing amino-allyl formate shown by a formula (I) after the reaction liquid B is carried out by desolventizing and column chromatography separation. The invention has the advantage that a polymer monomer perfluor-vinyl-containing amino-allyl formate (I) which has an absolutely new structure and is waterproof and grease-proof is provided; in addition, one-pot synthesizing is adopted, the intermediate process is simple, and the operation is convenient.

Description

1. Technical field [0001] The present invention relates to a novel polymer monomer containing perfluoroalkenyl allyl carbamate and its preparation method and application, in particular to perfluorononenyl-containing allyl carbamate and perfluorohexenyl-containing allyl carbamate Allyl carbamate. 2. Background technology [0002] Fluoropolymer refers to a C-C chain as the main chain, with one or more fluorine atoms connected to the side chain or branch chain, or even all fluorine atoms, mainly including fluororubber and fluoroplastic. The strong electronegativity of fluorine, high C-F bond energy (540kJ / mol), the smallest van der Waals radius except hydrogen, and the shielding effect on carbon chains endow fluoropolymers with superior thermal stability, weather resistance and chemical inertness. And special electrical properties (low conductivity constant), water and oil repellency [Chemical New Materials, 2004, 32 (8): 46], optical properties (low reflectivity), so in const...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C271/28C07C269/02C08F216/14C08F220/18C08F220/14B01F17/52C09K23/52
Inventor 史鸿鑫沈海民
Owner ZHEJIANG UNIV OF TECH
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