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Surfactant, composition containing the surfactant, use of the surfactant and fluorine-containing compound

A technology of surfactants and surface modifiers, applied in the field of surfactants, can solve the problems of difficult compound acquisition and use, and achieve the effect of excellent reducing ability and ensuring safety

Active Publication Date: 2015-07-29
AGC SEIMI CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] As a polymer containing the above-mentioned perfluoroalkyl group, generally, the longer the chain length of the group, the more hydrophobic and oleophobic it is, but as mentioned above, the compound having a perfluoroalkyl group with a chain length of 8 or more is obtained. and it becomes increasingly difficult to use

Method used

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  • Surfactant, composition containing the surfactant, use of the surfactant and fluorine-containing compound
  • Surfactant, composition containing the surfactant, use of the surfactant and fluorine-containing compound
  • Surfactant, composition containing the surfactant, use of the surfactant and fluorine-containing compound

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Embodiment

[0328] The present invention will be specifically described below through examples, but the present invention is not limited by the following examples. Hereinafter, unless otherwise specified, the units represented by "parts" and "%" are "parts by mass" and "% by mass".

Synthetic example 1

[0329] (Synthesis Example 1) Synthesis of Compound (a1) (see Table 1)

[0330] 79.9 g of iminodiacetic acid, 490.4 g of 2-perfluorohexyl ethanol, 707 g of cyclohexane, and 171.1 g of p-toluenesulfonic acid monohydrate were put into a 2 L four-necked flask, and refluxed for 14 hours while removing generated water. Then, when the solution was concentrated under reduced pressure to 885 g, 741.2 g of isopropanol was added, stirred overnight, and filtered under reduced pressure while washing the precipitated solid with isopropanol to obtain 531.3 g of a white solid.

[0331] 565.6 g of hexafluoro-m-xylene, 848.8 g of water, 53.0 g of sodium carbonate, and 212 g of isopropanol were added to the white solid, and after stirring well, the lower layer divided into two layers was recovered. In addition, after washing|cleaning with water-isopropanol, it dried with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to obtain 375.0 g of white solids.

[0332] In...

Synthetic example 2

[0336] (Synthesis Example 2) Synthesis of Compound (a2) (see Table 1)

[0337] 110.3 g of 2-perfluorohexyl ethanol, 16.65 g of L-aspartic acid, 62.4 g of cyclohexane, and 28.46 g of p-toluenesulfonic acid monohydrate were put into a 300 ml four-necked flask, and refluxed for 20 g while removing the generated water. Hour. The reaction liquid was cooled to 60° C. or lower, and the precipitated solid was filtered under reduced pressure while washing the precipitated solid with acetone and IPA. The obtained solid was vacuum-dried to obtain 88.5 g of a white solid.

[0338] 79.78 g of the obtained solid, 199.44 g of dichloromethane, and 17.8 g of triethylamine were poured into a 300 ml four-necked flask, and cooled to 0.3° C. with ice water. Here, 8.69 g of acryloyl chloride was slowly added dropwise. After stirring at room temperature for 2 hours, it was filtered. After adding 0.01 g of hydroquinone here, it was washed with water twice, and the lower layer was recovered and con...

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Abstract

Provided are: uses of a polymer that includes structural units derived from compounds represented by formula (a), as a surfactant having a superior ability to reduce surface tension or as a surface modifier and coating material for imparting antifouling properties; and a composition in each of these uses. Further provided is a novel fluorine-containing compound which is useful as a surfactant from among the aforesaid compounds. CH2=CR1-COX-CR2R3-(CH2)n-COO-Q1-Rf1 (a) In the formula, X is -0- or -NR4-; R1 is a hydrogen atom or methyl group; R2, R3, and R4 are each independently a hydrogen atom, a C1-3 alkyl group, or a group represented by formula (r) -(CH2)m-COO-Q2-Rf2 (r); n and m are each independently an integer 0-4; Rf1 and Rf2 are each independently a C1-6 polyfluoroalkyl group or polyfluoroether group; and Q1 and Q2 are each independently a single bond or divalent linking group.

Description

technical field [0001] The present invention relates to surfactants, in particular to polymeric fluorine-containing surfactants and compositions containing the surfactants. Furthermore, it relates to a fluorine-containing compound that can be used as the surfactant. It also relates to the use of the surfactant, specifically, to a surface modifier for imparting oil repellency and hydrophilicity or water repellency to a resin, a resin composition and a paint containing the surfactant. Background technique [0002] A fluorine-containing compound having a fluorine-containing alkyl group as a hydrophobic group has a high ability to reduce surface tension, so when it is added as a surfactant to a coating composition, etc., it can exhibit excellent penetrability, wettability, The effect of smoothness, etc. As the fluorine-containing compound, fluorine-containing compounds of various structures have been proposed so far. [0003] Among such fluorine-containing compounds, polymeri...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K3/00B01F17/52C07C233/49C08F20/28C08F20/58C08F220/24C08F220/58C09D7/12C09D201/00C09K23/22C09K23/42C09K23/52
CPCC09D5/1668C08F220/36C08F220/58C07C233/49C09D7/02C08F220/60C09D7/45
Inventor 石渡房惠三桥雅人川手朝海
Owner AGC SEIMI CHEM CO LTD