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Surface active agent containing hexafluoropropylene tripolymer group and preparation method thereof

A technology of surfactant and hexafluoropropylene, which is applied in the preparation of organic compounds, amino hydroxyl compounds, sulfate esters, etc., can solve the problem of poor surface activity and poor stability of hexafluoropropylene trimer derivatives, which cannot meet the requirements of the application. Requirements and other issues to achieve good surface activity and thermal stability

Active Publication Date: 2013-12-11
HUAZHONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] There are two main problems in the synthesis of fluorine-containing surfactants using hexafluoropropylene trimer as a fluorine-containing precursor material: one is that the perfluoroalkyl chain of hexafluoropropylene trimer is shorter than that of PFOS and PFOA, and it has branched chain structure, so the surface activity of hexafluoropropylene trimer derivatives is relatively poor, and has not been widely used; the second is that hexafluoropropylene trimer is derivatized as a fluorine-containing precursor material, and the reaction type is mainly vinyl fluoride Nucleophilic substitution, generally, compounds derived from alkyl nucleophiles have poor stability and cannot meet the requirements of specific use occasions

Method used

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  • Surface active agent containing hexafluoropropylene tripolymer group and preparation method thereof
  • Surface active agent containing hexafluoropropylene tripolymer group and preparation method thereof
  • Surface active agent containing hexafluoropropylene tripolymer group and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Embodiment 1 intermediate (M 1 ~ M 7 ) preparation

[0036] Intermediate (M 1 ~ M 7 ) synthetic route map as figure 1 shown.

[0037] Intermediate M 1 preparation of

[0038] Add 12.4g (0.1mol) p-hydroxybenzyl alcohol, 17.9g (0.13mol) potassium carbonate, 200mL THF (tetrahydrofuran) into a 1000mL three-necked flask, heat to reflux, and slowly add 58.5g (0.13mol) hexafluoropropylene trimer dropwise , continue to react for 2.5h, and TCL monitors the end of the reaction. Add 150mL ethyl acetate to the reaction solution, wash 3 times with saturated NaCl solution, and the organic layer is dried and precipitated to obtain the yellow liquid intermediate 4-perfluoro(4-methyl-3-isopropyl-2-pentane En-2-yl)oxybenzyl alcohol (M 1 ), 47.60g, and the yield was 86%. 1 H NMR (400MHz, CDCl 3 ):δ2.50(s,1H,-OH),4.61(s,2H,-CH 2 -),6.89(d,2H,J=7.8Hz,PhH),7.33(d,2H,J=7.8Hz,PhH); 19 F NMR (376MHz, CDCl 3 ):δ-56.93(d,3F,J=64.8Hz),-72.12(s,6F),-72.27(d,6F,J=38.8Hz),-168.27(d,6F,J...

Embodiment 2

[0055] The preparation of the surfactant containing hexafluoropropylene trimer base of embodiment 2 cationic series

[0056] N,N,N-Trimethyl-4-perfluoro(4-methyl-3-isopropyl-2-penten-2-yl)oxybenzyl ammonium iodide (A 1 ) preparation

[0057] Add 8.7 g (0.015 mol) of N,N-dimethyl-4-perfluoro(4-methyl-3-isopropyl-2-penten-2-yl)oxybenzylamine to a dry 250 mL flask (M 3 ), 4.3 g (0.03 mol) CH 3 I, 150 mL anhydrous CH 2 Cl 2 , react overnight at room temperature, filter with suction, and wash three times with ether to obtain a white solid as the target compound (A 1 ), 10.52g, the yield is 97%. 1 H NMR (400MHz,DMSO,δ,ppm):δ3.18(s,6H,N(CH 3 ) 2 ),δ4.44(s,2H,CH 2 ),δ6.96(d,2H,J=2.0Hz,PhH),δ7.62(d,2H,J=2.0Hz,PhH); 19 FNMR(376MHz,DMSO):δ-55.70(d,3F,J=60.9Hz),-70.92(s,6F),-71.99(s,6F),-167.31to-167.44(m,1F),-169.58 (s,1F);HPLC / MS(ESI):596.2(M + ) (calculated value: 596.09).

[0058]

[0059] N,N-Dimethyl-N-ethyl-4-perfluoro(4-methyl-3-isopropyl-2-penten-2-yl)oxybenzyl am...

Embodiment 3

[0092] Preparation of the hexafluoropropylene trimer-based surfactant of the amine oxide series of embodiment 3

[0093] N,N-Dimethyl-4-perfluoro(4-methyl-3-isopropyl-2-penten-2-yl)oxybenzylamine oxide (B 1 ) preparation

[0094] Add 6.4g (0.01mol) N,N-dimethyl-4-perfluoro(4-methyl-3-isopropyl-2-penten-2-yl)oxybenzylamine (M 3 ), 20mL30% (mass concentration) H 2 o 2 , 50mL methanol, reacted overnight at room temperature, desolvated, washed three times with ether to obtain a white solid as the target compound (B 1 ), 5.13g, the yield was 86%. 1 H NMR (600MHz, DMSO, δ, ppm): δ3.18(s, 6H, N-CH 3 ),δ4.44(s,2H,Ph-CH 2 -),δ6.96(d,2H,J=6.0Hz,PhH),δ7.62(d,2H,J=6.0Hz,PhH); 19 FNMR(376MHz,DMSO):δ-56.06(d,3F,J=36.5Hz),-70.73(d,6F),-72.90(s,6F),-167.51(s,1F),--169.71to- 170.78(m,1F);HPLC / MS(ESI):596.4(M + ) (calculated value: 597.06).

[0095]

[0096] N,N-diethyl-4-perfluoro(4-methyl-3-isopropyl-2-penten-2-yl)oxybenzylamine oxide (B 2 ) preparation

[0097] Add 7.3g (0.01m...

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Abstract

The invention discloses a surface active agent containing a hexafluoropropylene tripolymer group and a preparation method thereof. The hexafluoropropylene tripolymer is a fluorine-containing precursor material, and the surface active agent is prepared by taking a benzene ring as a rigid connecting chain. The surface active agent comprises a cation series, an amine oxide series and an anion series which are respectively in the form of 4-perfluoro-(4-methyl-3-isopropyl-2-amylene-2-group) oxygen benzyl ammonium cation, 4-perfluoro-(4-methyl-3-isopropyl-2-amylene-2-group) oxygen benzyl amine oxide and 4-perfluoro-(4-methyl-3-isopropyl-2-amylene-2-group) oxygen benzyl sulphonate (sulfate). The surface active agent disclosed by the invention has the advantages of no harm characteristic of a lasting organic pollutant, high surface activity, low critical micelle concentration and high heat stability; the fluorine-containing surface active agent disclosed by the invention has potential application value in special application fields of tertiary oil extraction, fluorine-containing polymer polymerization, and the like, and the fields of common surface active agents and the like.

Description

technical field [0001] The invention relates to a surfactant, in particular to a hexafluoropropylene trimer-based surfactant and a preparation method thereof. Background technique [0002] Surfactants are substances that contain both hydrophilic and hydrophobic groups. According to the different hydrophobic groups, it can be divided into hydrocarbon surfactants, fluorine-containing surfactants, etc. According to the different hydrophilic groups, it can be divided into cationic, anionic, nonionic, and amphoteric. Fluorosurfactants are compounds containing hydrophobic long-chain perfluoroalkyl or perfluoropolyethers and hydrophilic groups. Compared with general hydrocarbon surfactants, fluorine-containing surfactants have high surface activity, high thermal stability and high chemical stability, and excellent hydrophobic and oil-repellent properties, which are the so-called "three highs" and "two highs". It is suitable for various occasions where ordinary hydrocarbon surfac...

Claims

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Application Information

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IPC IPC(8): B01F17/18B01F17/42B01F17/12C07C305/18C07C303/24C07C303/32C07C309/24C07C291/04C07C227/08C07C229/14C07C213/08C07C217/58C09K23/18C09K23/12C09K23/42
Inventor 张爱东张少凯涂海洋王珊王乾有
Owner HUAZHONG NORMAL UNIV
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