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Perfluoralkylene-containing acrylate monomer and preparation method and application thereof

A technology for olefin-based acrylates and monomers, which is applied in the field of perfluoro-olefin-based acrylate monomers and their preparation and application, can solve problems such as danger, and achieve the effects of less by-products and simple synthesis methods

Active Publication Date: 2012-12-12
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, perfluorooctane sulfonic acid (PFOS) and its derivatives are subject to strict restrictions in the United States, the European Union and other developed countries due to their high persistence and accumulation in the environment and potential dangers.

Method used

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  • Perfluoralkylene-containing acrylate monomer and preparation method and application thereof
  • Perfluoralkylene-containing acrylate monomer and preparation method and application thereof
  • Perfluoralkylene-containing acrylate monomer and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Add 15mL of 1,2-dichloroethane, 1.74g (10mmol) of toluene-2,4-diisocyanate, 0.19g (0.8mmol) of tetraethyltin, and 0.02g of hydroquinone into a 50mL four-necked flask as a polymerization inhibitor 1.30 g (10 mmol) of hydroxyethyl methacrylate was added dropwise. After the dropwise addition, TLC was used to detect the reaction progress, and the temperature was kept and stirred for 4 hours. 6.11 g (10 mmol) of N-methyl-N-hydroxyethyl-4-perfluorononenyloxybenzylamine was added dropwise. After the dropwise addition was completed, TLC was detected to track the reaction progress, and the reaction was carried out while maintaining the temperature and stirring for 5 hours. Reaction is completed, and solvent extraction is separated by silica gel column chromatography (V 二氯甲烷 :V 乙酸乙酯 :V环己烷 =5:4:1), after removing the solvent, yellow viscous paste I was obtained 1 , (n=9, R is CH 3 ), yield 63.79%, purity 99.7%.

[0024] FT-IR (cm -1 ): 3332, 2957, 2857, 2798, 1714, 1618, 1601...

Embodiment 2

[0028] Carry out the reaction according to the method of Example 1, but N-methyl-N-hydroxyethyl-4-perfluorononenyloxybenzylamine is changed to N-methyl-N-hydroxyethyl-4-perfluorohexene Base oxybenzylamine 4.61g (10mmol), other reaction conditions are with embodiment 1, obtain pale yellow paste I 2 (n=6, R is CH 3 ), yield 61.8%, purity 99.5%.

[0029] 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

[0031] Carry out reaction according to embodiment 1 method, but hydroxyethyl methacrylate is changed into hydroxyethyl acrylate 1.16g (10mmol), other reaction conditions are with embodiment 1, get yellow paste I 3 (n=9, R is H), yield 66.1%, purity 99.3%

[0032] 1 H NMRδ(CDCl 3 ): 7.83(s, 1H), 7.33(d, 2H), 7.20(s, 1H), 7.08(d, 1H), 6.85(d, 2H), 6.72(s, 1H), 6.49(s, 1H) , 6.15(s, 1H), 6.05(s, 1H), 5.59(s, 1H), 4.40(m, 4H), 4.31(t, 2H), 3.56(s, 2H), 2.74(t, 2H), 2.28(s, 3H), 2.19(s, 3H).

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Abstract

The invention discloses a perfluoralkylene-containing acrylate monomer and a preparation method and application thereof. The preparation method comprises the following steps: (1) taking toluene-2,4-diisocyanate shown in a formula (II) as a raw material to perform first-step addition reaction with 2-hydroxyethyl methacrylate shown in a formula (III) by taking organic tin as a catalyst in a polar aprotic solvent, and reacting until the II basically disappears to obtain reaction liquid A of an intermediate shown in a formula (IV); and (2) directly adding the reaction liquid A to N-methyl-N-ethoxyl-p-perfluoralkenyl oxyl benzylamine shown in a formula (V) to perform second-step addition reaction, obtaining reaction liquid B after the reaction is over, and performing solvent removal and columnchromatography on the reaction liquid B to obtain the perfluoralkylene-containing acrylate monomer (I). The invention provides the perfluoralkylene-containing acrylate monomer (I) which is provided with a brand-new structure and can be used for preparing a surfactant; and the synthesis method for the substance is simple, and has less byproducts.

Description

(1) Technical field [0001] The invention relates to a novel polymer perfluoroalkene-based acrylate monomer and its preparation method and application. (2) Background technology [0002] Polymer surfactants usually refer to substances with a relative molecular mass of more than several thousand and significant surface activity. They have a long history of application, and some natural polymers have been used as polymer surfactants [Leather Science and Engineering, 2004, 14(6):24-30]. Compared with low-molecular-weight surfactants, polymer surfactants have the advantages of poor permeability, good film-forming properties, low or no toxicity, environmental friendliness, good dispersion, emulsification, and stability [Chemical Progress, 2005, 17(1 ): 151-156]. The introduction of fluorine atoms into polymer surfactants produces polymer fluorine-containing surfactants. Polymer fluorine-containing surfactants not only have the excellent performance of polymer surfactants, but al...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C271/28C07C269/02C08F220/36C08F220/18C08F220/14B01F17/52C09K23/52
Inventor 史鸿鑫沈海民
Owner ZHEJIANG UNIV OF TECH
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