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Nitrogen-containing organoxysilane compound and method for producing same

A manufacturing method and compound technology, applied in the field of nitrogen-containing polyfunctional organooxysilane compound and its manufacturing, can solve the problems that the effect cannot be fully exerted, and achieve the effect of excellent additive effect

Pending Publication Date: 2017-11-03
SHIN ETSU CHEM IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] When these silane compounds having amino groups are used in the above-mentioned various applications, even if there are many organooxy groups functioning as reaction sites, there are only three, and there is only one silicon atom to which the organooxy group is bonded. Therefore, there are The possibility that the effect brought by the addition cannot be fully exerted

Method used

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  • Nitrogen-containing organoxysilane compound and method for producing same
  • Nitrogen-containing organoxysilane compound and method for producing same
  • Nitrogen-containing organoxysilane compound and method for producing same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0071] Put 204.9 g (0.6 mol) of bis(3-trimethoxysilylpropyl)amine (manufactured by Shin-Etsu Chemical Co., Ltd.), triethyl Amine 66.8g (0.66mol), heated to 80°C. After the internal temperature became stable, 63.6 g (0.32 mol) of 1,3-dibromopropane was dripped over 1 hour, and it stirred at this temperature for 20 hours. The salt produced by the reaction was removed by filtration, and the low boiling point compound was distilled off from the filtrate under heating at 90° C. / 0.4 kPa under reduced pressure to obtain 192.5 g of a liquid compound.

[0072] For the obtained compounds, the determination 1 H-NMR spectrum (deuterated chloroform solvent) and IR spectrum. The results are shown in image 3 , 4 in.

[0073] From the above results, it was confirmed that the obtained compound was N,N,N',N'-tetrakis(3-trimethoxysilylpropyl)-1,3-propanediamine.

Embodiment 2

[0075] Put [3-dimethoxy(4-pentenyloxy)silylpropyl]-(3-trimethoxysilylpropyl) into a flask equipped with stirrer, reflux, dropping funnel and thermometer 197.9 g (0.5 mol) of amine (manufactured by Shin-Etsu Chemical Co., Ltd.) and 71.1 g (0.55 mol) of ethyldiisopropylamine were heated to 80°C. After the internal temperature became stable, 53.0 g (0.27 mol) of 1,3-dibromopropane was dripped over 1 hour, and it stirred at this temperature for 20 hours. The salt produced by the reaction was removed by filtration, and the low boiling point compound was distilled off from the filtrate under heating at 90° C. / 0.4 kPa under reduced pressure to obtain 204.9 g of a liquid compound.

[0076] For the obtained compounds, the determination 1 H-NMR spectrum (deuterated chloroform solvent) and IR spectrum. The results are shown in image 3 , 4 in.

[0077] From the above results, it was confirmed that the obtained compound was N,N'-bis[3-dimethoxy(4-pentenyloxy)silylpropyl]-N,N'-bis(3-tr...

Embodiment 3

[0079] Put [3-dimethoxy(1-methyl-2-methoxyethoxy)silylpropyl]-(3- 199.9 g (0.5 mol) of trimethoxysilylpropyl)amine (manufactured by Shin-Etsu Chemical Co., Ltd.), and 55.7 g (0.55 mol) of triethylamine were heated to 80°C. After the internal temperature became stable, 53.0 g (0.27 mol) of 1,3-dibromopropane was dripped over 1 hour, and it stirred at this temperature for 20 hours. The salt produced by the reaction was removed by filtration, and the low boiling point compound was distilled off from the filtrate under heating at 90° C. / 0.4 kPa under reduced pressure to obtain 204.0 g of a liquid compound.

[0080] For the obtained compounds, the determination 1 H-NMR spectrum (deuterated chloroform solvent) and IR spectrum. The results are shown in Figure 5 ,6 in.

[0081] From the above results, it was confirmed that the obtained compound was N,N'-bis[3-dimethoxy(1-methyl-2-methoxyethoxy)silylpropyl]-N,N'-bis (3-Trimethoxysilylpropyl)-1,3-propanediamine.

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Abstract

The invention provides a nitrogen-containing organoxysilane compound which can express an excellent addition effect in case of using as a silane coupling agent, a surface treating agent, a resin additive, a coating additive, and an adhesive, and a method for producing the same. The nitrogen-containing organoxysilane compound is represented as a following general formula (1). (R1 to R4 mutually independently represent plus-1 substituted or unsubstituted hydrocarbyl with 1 to 20 carbon atoms , R5 and R6 mutually independently represent plus-2 hydrocarbyl that may include 1 to 10 hetero atoms, R7 represents plus-2 hydrocarbyl that may include 3 to 20 hetero atoms, and m and n mutually independently represent the integer of 0, 1 or 2.

Description

technical field [0001] The present invention relates to a nitrogen-containing polyfunctional organooxysilane compound and a manufacturing method thereof, more specifically, to a nitrogen-containing polyfunctional organic oxygen silane compound used as a silane coupling agent, a surface treatment agent, a resin additive, a coating additive, a binder, etc. Silane compound and its production method. Background technique [0002] Nitrogen-containing organooxysilane compounds are useful as silane coupling agents, surface treatment agents, resin additives, paint additives, adhesives, and the like. [0003] As such nitrogen-containing organooxysilane compounds, organooxysilane compounds having primary amino groups such as aminopropyltrimethoxysilane, and organooxysilane compounds having secondary amino groups such as N-phenylaminopropyltrimethoxysilane are known. , dimethylaminopropyltrimethoxysilane and other organooxysilane compounds having tertiary amino groups. [0004] When ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/18
CPCC07F7/1804C07F7/1892
Inventor 殿村洋一久保田透本间孝之
Owner SHIN ETSU CHEM IND CO LTD
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