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Perfluoro-substituted micromolecular terminal diol as well as preparation method and application thereof

A technology of small molecule and base diol, which is applied in the field of perfluoro-substituted small-molecule end-group diol and its preparation, can solve the problem of limited side chain fluorine-containing polyurethane preparation and application, rare varieties of fluorine-substituted small-molecule end-group diol, etc. problem, to achieve the effect of strong adhesion, simple preparation method, good chemical corrosion resistance and weather resistance

Active Publication Date: 2019-07-19
NANJING UNIV OF INFORMATION SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, affected by various factors, the fluorine-substituted small-molecule terminal diols that can be used to prepare side-chain fluorine-containing polyurethanes are currently rare, which limits the preparation and application of side-chain fluorine-containing polyurethanes to a certain extent.

Method used

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  • Perfluoro-substituted micromolecular terminal diol as well as preparation method and application thereof
  • Perfluoro-substituted micromolecular terminal diol as well as preparation method and application thereof
  • Perfluoro-substituted micromolecular terminal diol as well as preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0024] Example 1: Preparation of perfluorinated substituted small molecule terminal diols

[0025] Add perfluorobutyl ethyl glycidyl ether, ethyl-substituted ethanolamine and tetrabutylammonium bromide into the reaction kettle in a molar ratio of 1:1.02:0.02, heat up to 65°C, stir for 5 hours, then stop the reaction. The reaction solution was distilled off under reduced pressure to remove unreacted raw materials, and the target product 1 was obtained as a pale yellow liquid with a conversion rate of 95%.

Embodiment 2

[0026] Example 2: Preparation of perfluorinated substituted small molecule terminal diols

[0027] Add perfluorohexyl ethyl glycidyl ether, ethyl-substituted ethanolamine and tetrabutylammonium bromide into the reaction kettle according to the molar ratio of 1:1.05:0.03, heat up to 75°C, stir the reaction for 7 hours, stop the reaction, and put the reaction The liquid was distilled off under reduced pressure to remove unreacted raw materials, and the light yellow liquid was obtained as the target product 2, and the conversion rate was 96%. The nuclear magnetic characterization of the target product 2 proved that its molecular structure is as shown in structural formula I, and it was named 1-(ethyl(2-hydroxyethyl)amino)-3-(3,3,4,4,5,5, 6,6,7,7,8,8,8-Tridecafluorooctyloxy)propan-2-ol (FPO), its NMR spectrum is shown in figure 1 .

Embodiment 3

[0028] Example 3: Preparation of perfluorinated substituted small molecule terminal diols

[0029] Add perfluorodecyl ethyl glycidyl ether, ethyl-substituted ethanolamine and tetrabutylammonium bromide into the reaction kettle according to the molar ratio of 1:1.07:0.05, heat up to 90°C, and stop the reaction after stirring for 10 hours. The reaction solution was distilled under reduced pressure to remove unreacted raw materials, ethyl acetate and methanol (V / V=10 / 1) were used as developing solvents, and separated by a chromatographic column to obtain a light yellow liquid as the target product 3 with a conversion rate of 97%.

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Abstract

The invention discloses perfluoro-substituted micromolecular terminal diol which has a molecular structure shown as a structural formula I. The diol with the structural formula I is colorless or slightly yellow transparent liquid; and in the formula I, n is any natural number in the range of 2-11; m is 1 or 2; and R is any one of methyl, ethyl, propyl, butyl isopropyl or isobutyl. The perfluoro-substituted micromolecular terminal diol prepared by the invention is high in purity, almost no side reaction exists, the preparation method is simple, the product conversion rate is high, the single-component normal-temperature self-crosslinkeing side-chain fluorine-containing polyurethane which is uniform in synthesis performance and capable of being stored for a long time can be used, and a super-hydrophobic oleophobic self-cleaning coating prepared from the side-chain fluorine-containing polyurethane has the advantages of being high in adhesive force with a base material, resistant to surface abrasion, resistant to solvent soaking, resistant to chemical corrosion, good in weather resistance and the like.

Description

technical field [0001] The invention relates to a perfluorinated substituted small molecule end group diol, in particular to a perfluorinated substituted small molecule end group diol and its preparation method and application. Background technique [0002] Fluorine is located in the main group VII of the second period of the periodic table, and the distribution of electrons outside the nucleus is 1S 2 2S 2 2P 5 That is to say, the extranuclear electrons of the fluorine atom are all distributed in the first and second layers of atomic orbitals, which are relatively close to the nucleus. The nine positive charges in the nucleus firmly attract the extranuclear electrons around the nucleus, which determines The atomic radius of fluorine atoms is relatively small. When forming a covalent bond with a carbon atom, due to the high electronegativity of fluorine, the bond length of the C-F bond Only slightly longer than the C-H bond, the bond energy of the C-F bond is larger, re...

Claims

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Application Information

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IPC IPC(8): C07C213/06C07C217/28C08G18/66C08G18/48C08G18/32C09D175/08C09D5/16
CPCC07C217/28C08G18/3206C08G18/3812C08G18/4854C08G18/6666C09D5/1662C09D175/08
Inventor 孔庆刚孔繁昕张龙
Owner NANJING UNIV OF INFORMATION SCI & TECH