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Partially fluorinated aromatic esters

A technology of aryl and composition, applied in the field of polymer composition, can solve the problems of expensive, poor thermal stability, etc.

Active Publication Date: 2019-04-26
3M INNOVATIVE PROPERTIES CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] Although these fluorochemical melt additives can in some cases impart satisfactory hydrophobicity and / or oleophobicity to thermoplastic resins, they generally have poor thermally stable, and they can also be very expensive, leading to limitations in their commercial utility

Method used

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  • Partially fluorinated aromatic esters
  • Partially fluorinated aromatic esters
  • Partially fluorinated aromatic esters

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0089] Material

[0090] All chemicals were obtained or are generally commercially available from chemical companies such as Sigma-Aldridge Chemical Company, St. Louis, MO, unless otherwise indicated.

[0091] C18 diester (C 4 f 9 SO 2 N(CH 3 )CH 2 CH 2 OOC (CH 2 ) 16 COOCH 2 CH 2 (CH 3 ) NSO 2 C 4 f 9 ) was prepared by the method described in F-4 of the following US Patent No. 7,396,866 B2.

[0092] method

[0093] Water repellency test method

[0094] For the water repellency test, film samples prepared according to the Examples and Comparative Examples described below were placed on a flat, horizontal surface. Five small drops of water or a water / isopropanol (IPA) mixture were gently placed on a spot at least two inches (approximately 5 cm) away from the film sample. The film sample was considered to pass the test if four out of five drops were visible as spheres or hemispheres after ten seconds of viewing at a 45° angle. The reported water repellenc...

preparation example 1

[0098] Preparation Example 1 (PE1)

[0099]

[0100] 1,1,2,2,3,3,4,4,4-nonafluoro-N-(2-hydroxyethyl)-N-methyl-butane-1-sulfonamide (249g, 697.11mmol) , methanesulfonic acid (1.73mL, 26.1mmol), isobenzofuran-1,3-dione (51.5g, 348mmol) and toluene (174mL, 1630mmol) were added to a 500mL circle equipped with a magnetic stirring bar and reflux condenser in the bottom flask. The reaction mixture was stirred at 110 °C for 18 hours. Triethylamine (3.67 mL, 26.1 mmol) was then added to the resulting pale yellow solution, and the reaction mixture was allowed to cool to room temperature. The resulting precipitate was collected by filtration, washed with toluene, and dried under vacuum to afford benzene-1,2-dicarboxylic acid bis[2[methyl(1,1,2,2,3,3, 4,4,4-Nafluorobutylsulfonyl)amino]ethyl]ester (273 g, 323.3 mmol, 93.0% yield). The identity of the material was confirmed by LC / MS and NMR techniques.

preparation example 2

[0101] Preparation example 2 (PE2)

[0102]

[0103]1,1,2,2,3,3,4,4,4-nonafluoro-N-(2-hydroxyethyl)-N-methylbutane-1-sulfonamide (2.01 equivalents, 566mmol), Triethylamine (2.2 equivalents, 620 mmol) and toluene (0.5 M, 5280 mmol) were added to a mixture equipped with a mechanical stirrer, reflux condenser and benzene-1,3-dicarbonyl chloride dissolved in a mixture of toluene and dichloromethane ( 57.2g, 282mmol) in a 1L 3-neck flask with an addition funnel. Dissolved ethanol was added to the stirred reaction mixture under positive nitrogen pressure. An exotherm was observed and a white precipitate started to form. After the addition was complete, the reaction mixture was allowed to stir at room temperature for 18 hours, at which time water (300 mL) was added. The mixture was allowed to stir for 5 minutes, and the resulting white solid was collected by filtration and washed sequentially with dichloromethane (300 mL, 3x) and water (300 mL, 3x). The resulting white powde...

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Abstract

Described are compounds of the formula shown in the specification, wherein RAryl is an aryl group; R1 is a linear or branched C2-C40 hydrocarbyl group; R2 is a C1-C4 alkyl; Rf is a perfluorinated group of having an average of 3 to 5 carbon atoms; and the subscript x is 1 to 3.

Description

Background technique [0001] The present invention relates to partially fluorinated sulfonamide compounds having fluoroaliphatic and fluoroaliphatic groups. The invention also relates to a polymer composition comprising a fluorochemical composition and a shaped article made from the thermoplastic composition. [0002] According to H.C. Fielding, "Organofluorine Compounds and Their Applications," edited by R.E. Banks, Society of Chemical Industry, p. 214, 1979, organofluorine compounds as surface-active agents ( ie surfactants) and surface treatment agents are largely due to the C 6 -C 12 The extremely low surface free energy of the fluorocarbon group. Generally, the aforementioned organofluorine species are those having carbon-bonded fluorine in the form of a monovalent fluoroaliphatic group such as a perfluoroalkyl group, typically -C n f 2n+1 , wherein n is at least 3, and the terminal moiety of said group is trifluoromethyl, -CF 3 . [0003] A number of patents have p...

Claims

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Application Information

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IPC IPC(8): C07C311/09C08K5/17
CPCC08K5/435C07C311/09C08L75/04C08K5/175
Inventor G·特维罗维斯基C·P·贾里瓦拉T·P·科伦
Owner 3M INNOVATIVE PROPERTIES CO
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