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Fluorine-containing maleimide compound and its production method

A technology of maleimide and manufacturing method, which is applied in the direction of silicon organic compounds, chemical instruments and methods, compounds of group 4/14 elements of the periodic table, etc., which can solve problems such as obstacles and achieve high yield effects

Active Publication Date: 2016-09-14
SHIN ETSU CHEM IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, radical polymerization of acrylic compounds using ultraviolet light is affected by barriers caused by oxygen when curing in air

Method used

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  • Fluorine-containing maleimide compound and its production method
  • Fluorine-containing maleimide compound and its production method
  • Fluorine-containing maleimide compound and its production method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0123] Heat up 20.0 g of the following compound (5), 10.6 g of 4-bromo-1-butene, and 20 g of m-ditrifluorotoluene in a flask equipped with a stirring and reflux device to 90° C., and mix chloroplatinic acid / ethylene 0.040g toluene solution of siloxane complex (containing 1.0×10 -7 moles of Pt monomer), heating and stirring continued for 12 hours. After adding 1 part by mass of activated carbon to the mixed solution obtained after the heating was stopped, and stirring for 1 hour, pressure filtration was performed. The organic solvent was evaporated from the filtrate with an evaporator at 110° C. / 2 Torr to obtain 29.5 g of a light yellow transparent liquid. The obtained liquid according to 1 H NMR, 13 C NMR identified the compound as the following (6).

[0124]

[0125] 10.0 g of the obtained compound (6), 4.24 g of the compound represented by the general formula (3), 17.3 g of potassium carbonate, and 30 g of DMF were stirred at 50° C. for 48 hours in a flask equipped wi...

Embodiment 2

[0130] Heat 20.0 g of the following compound (11), 13.5 g of 4-bromo-1-butene, and 20 g of m-trifluorotoluene in a flask equipped with a stirring and reflux device to 90° C., and mix chloroplatinic acid / vinyl Toluene solution of siloxane complex 0.040g (containing 1.0×10 -7 moles of Pt monomer), heating and stirring continued for 12 hours. Thereafter, volatile parts were removed from the reaction solution by distillation under reduced pressure at 110° C. / 2 Torr to obtain 30.2 g of a pale yellow transparent liquid. The obtained liquid according to 1 H NMR, 13 C NMR identified the following compound (12).

[0131]

[0132] 10.0 g of the obtained compound (12), 4.92 g of the compound represented by the general formula (3), 20.6 g of potassium carbonate, and 30 g of DMF were stirred at 50° C. for 48 hours in a flask equipped with a stirring device and a reflux device. To the solution after the stirring was stopped, 50 ml of ethyl acetate was added, followed by washing with ...

Embodiment 3

[0139] Heat 20.0 g of the following compound (15), 15.0 g of 4-bromo-1-butene, and 20 g of m-trifluorotoluene in a flask equipped with a stirring and reflux device to 90° C., and mix chloroplatinic acid / vinyl Toluene solution of siloxane complex 0.040g (containing 1.0×10 -7 moles of Pt monomer), heating and stirring continued for 12 hours. Thereafter, volatile parts were removed from the reaction solution by distillation under reduced pressure at 110° C. / 2 Torr to obtain 33.4 g of a pale yellow transparent liquid. The obtained liquid according to1 H NMR, 13 C NMR identified the following compound (16).

[0140]

[0141] 10.0 g of the obtained compound (16), 3.49 g of the compound represented by the general formula (3), 14.6 g of potassium carbonate, and 30 g of DMF were stirred at 50° C. for 48 hours in a flask equipped with a stirring device and a reflux device. To the solution after the stirring was stopped, 50 ml of ethyl acetate was added, followed by washing with 10...

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Abstract

PROBLEM TO BE SOLVED: To provide a fluorine-containing maleimide compound having a fluorine group and a sufficiently controlled structure, and a method of producing the fluorine-containing maleimide compound in high yield.SOLUTION: A fluorine-containing maleimide compound has at least one fluoroalkyl group and / or a fluoropolyether group in one molecule, has at least one residue bonded to a silicone atom, and is represented by formula (8). When the fluorine-containing maleimide compound is added to a hard coating agent and a coated surface is irradiated with ultraviolet rays, a cured coating film, wherein fluorine groups are unevenly distributed on the outermost surface, is formed, and superior functions such as water repellency, oil repellency, and abrasion resistance can be exhibited.

Description

technical field [0001] The invention relates to a fluorine-containing maleimide compound and a production method thereof. Background technique [0002] Previously, polymerizable monomers having perfluoroalkyl groups in branched chains have been known as fluorine compounds curable by irradiation with light such as ultraviolet rays, for example, polymerizations including fluorine-containing alkyl acrylates and fluorine-containing alkyl methacrylates. thing. Such so-called fluorine-containing acrylic compounds, as additives to improve the surface properties of the surface, have attracted attention in recent years to hard coat protective films obtained from ultraviolet-curable hard coat materials, and high-performance The requirements are also gradually increasing. For example, Patent Documents 1, 2 and the like describe fluorine-containing acrylates and the like in which the functionality is improved by controlling the structure using a polyfunctional Si—H compound. [0003]...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/21
CPCC07F7/12C07F7/21
Inventor 坂野安则
Owner SHIN ETSU CHEM IND CO LTD