Functional organosiloxane containing asymmetrical substituted urea and preparation method thereof

A technology of organosiloxane and substituted urea, which is applied in the field of functional organosiloxane and its preparation, can solve the problems of single special function and rare varieties, and achieves a product with good interfacial compatibility, easy hydrolysis and high conversion rate. Effect

Inactive Publication Date: 2014-04-30
FUJIAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In order to overcome the shortcomings of functional siloxanes with single special functions and few varieties, the purpose of ...

Method used

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  • Functional organosiloxane containing asymmetrical substituted urea and preparation method thereof
  • Functional organosiloxane containing asymmetrical substituted urea and preparation method thereof
  • Functional organosiloxane containing asymmetrical substituted urea and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0033] Synthesize 1,1-bis(4-bromobenzene)-3-(3-triethoxysilyl)propylurea according to the following method, and the synthetic route is as follows:

[0034]

[0035] Concrete synthetic steps are as follows:

[0036] (1) N,N -Synthesis of two (4-bromophenyl) carbamoyl chlorides

[0037] In a 100ml three-neck flask equipped with electromagnetic stirring and temperature control device, 4,4 ， -Dibromodiphenylamine (0.8175g, 2.5mmol) was dissolved in 50ml of dichloromethane, continued to add triethylamine (1.515g, 15mmol), then added solid triphosgene (2.673g, 9mmol), refluxed and stirred at room temperature, The reaction was detected by TLC tracking, and the reaction was stopped after 24 hours. After the reaction was over, dichloromethane was distilled off under reduced pressure, and the crude product was separated and purified by column chromatography (petroleum ether: dichloromethane=2:1) ​​to obtain 0.84 g of a light yellow solid intermediate, which was purified by 1...

Embodiment 2

[0046] Synthesis of 1,1-bis(4-bromophenyl)-3-(3-trimethoxysilyl)propylurea

[0047] In a 100ml three-necked flask equipped with electromagnetic stirring, the intermediate N,N-bis(4-bromophenyl)carbamoyl chloride (0.934g, 2.4mmol), 50ml of ether, and triethylamine (0.606g , 6mmol), 3-aminopropyltrimethoxysilane (0.72g, 4mmol), pass into N 2 Protection, TLC detection reaction, stop after 12 hours at room temperature. After the reaction, the white precipitate was filtered off, the filtrate was distilled off under reduced pressure to remove ether, and the crude product was separated and purified by column chromatography (petroleum ether: ethyl acetate = 3:1) to obtain 1.08 g of a light yellow solid product with a yield of 84.4%. The infrared spectrum, ultraviolet spectrum of example 1, 1 H-NMR and 13 C-NMR determined it to be 1,1-bis(4-bromophenyl)-3-(3-trimethoxysilyl)propylurea.

Embodiment 3

[0049] Synthesis of 1,1-diphenyl-3-(3-triethoxysilyl)propylurea

[0050] In a 100ml three-necked flask equipped with electromagnetic stirring and a temperature control device, diphenylamine (1.69g, 10mmol) was dissolved in 50ml of dichloromethane, triethylamine (3.03g, 30mmol) was added continuously, and then solid triphosgene (5.346 g, 18mmol), reflux and stir at room temperature, TLC detection reaction, stop the reaction after 24h. After the end of the reaction, dichloromethane was distilled off under reduced pressure to obtain the intermediate N,N -diphenylcarbamoyl chloride; add the N,N -diphenylcarbamoyl chloride (1.15g, 5mmol), ether 50mL, pyridine (0.48g, 6mmol), 3-aminopropyl triethoxysilane (1.1g, 5mmol), pass into N 2 Protection, TLC detection reaction, stop after 12 hours at room temperature. After the reaction, the yellow precipitate was filtered off, the filtrate was distilled off under reduced pressure to remove diethyl ether, and the crude product was separ...

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Abstract

The invention discloses functional organosiloxane containing asymmetrical substituted urea and a preparation method thereof. The preparation method comprises the following steps: carrying out reaction between 4, 4'-dibromodiphenylamine and triphosgene to obtain (i) N, N(/i)-di(4-bromo phenyl) carbamyl chloride; and then, carrying out reaction with 3-aminopropyl triethoxysilane to obtain functional organosiloxane, wherein the organosiloxane is the functional organosiloxane containing asymmetrical substituted urea through the verification of infrared spectrum, ultraviolet spectrum, 1H-NMR (1Hydrogen-Nuclear Magnetic Resonance) and 13C-NMR. The structure of the compound contains a plurality of functional groups such as siloxane, amide, urea groups and bromoaryl. The functional organosiloxane has a potential application value on the respects of molecular imprinting recognition materials, structural flame retardant materials, rare earth light emitting materials, white carbon black and the like. The functional organosiloxane disclosed by the invention is reasonable in synthetic line, mild in condition, easy to operate, low in cost of raw materials and high in product yield.

Description

technical field [0001] The invention relates to a functional organosiloxane containing an asymmetric substituted urea and a preparation method thereof. Specifically, it relates to 1,1-bis(4-bromophenyl)-3-(3-triethoxysilyl)propylurea and its preparation method. Background technique [0002] Functional organosiloxane is an important class of organosilicon compounds. It is a class of compounds developed for some special purposes. Its molecules have reactive groups that can chemically bond with inorganic substances and chemically bond with organic substances. The reactive group, its structural formula can be expressed as (OR) 3 Si(CH 2 ) n Y, n=0~3: R is an alkyl group, usually methyl, ethyl, etc.; Y is an organic functional group, usually vinyl, amino, epoxy, mercapto or ureido, etc. Functional organosiloxanes are mainly used in surface treatment of inorganic materials, modification of polymer materials and surface protection of metal materials. Commonly used functional or...

Claims

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Application Information

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IPC IPC(8): C07F7/18C09C1/28C09C3/12B01J20/26B01J20/285B01J20/30
Inventor 童跃进郑锦华关怀民高勇戴宏邹行郭静
Owner FUJIAN NORMAL UNIV
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