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Method for preparing hydroxyimino organosilicon compounds

A technology of organosilicon compounds and organoalkoxysilanes, which is applied in the field of preparation of oxime-based organosilicon compounds, can solve problems such as difficult product quality assurance, process complexity, and difficult control, so as to improve effectiveness and conversion rate, shorten Response time and the effect of removing potential safety hazards

Active Publication Date: 2012-07-04
TONSAN ADHESIVES INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Organoxime-based silanes are generally obtained by reacting corresponding organochlorosilanes with corresponding oximes. For example, a reaction with chlorosilane or chlorosiloxane and oxime is described in US3189576, and pyridine is used as a neutralizing agent; US4918209 A synthetic method using ammonia as a neutralizing agent is described; and in US4400527 and US4380660, organic oximes are not only used as reactants, but also act as acid absorbents; but the above methods all have complex processes and safety hazards; the coexistence of organic oximes and acidic substances often results in the existence of this danger. For example, the acidification of methyl ethyl ketone oxime and hydrochloric acid will decompose violently at a lower temperature and is difficult to control. Under certain circumstances, this type of compound has risk of explosion;
[0004] In another attempt, US4766231 provides a method for preparing organoalkoxyxime silane, which is obtained by reacting organoalkoxysilane and oxime in the presence of a catalyst. However, due to the solvent-free nature of the system, the reaction is not effective; in order to increase the conversion rate and yield of the reaction, one or more solvents are used in the reaction system, and the solvent not only provides the reaction and heating medium, and the solvent system can form an azeotrope with the removal molecule, which makes the reaction easier to carry out; for example, in US4705877, toluene is used for the reaction of aminopropyltrimethoxysilane and methyl ethyl ketone The corresponding oxime-based compounds are prepared by heating; however, due to the requirements of heating time and temperature, it is difficult to guarantee the quality of the product in order to obtain a high reaction conversion rate, especially for those with high reactivity and temperature sensitivity. substances, in particular;

Method used

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  • Method for preparing hydroxyimino organosilicon compounds

Examples

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Effect test

example 1

[0027] The reaction device includes a 5-liter glass reaction kettle, an upper mechanical stirring device, a reflux column, a condensation column and a receiving bottle. The system is connected to a vacuum controller through a buffer bottle, and the vacuum controller is connected to a vacuum system with a vacuum degree of 0.01 mbar. Into the kettle were charged 430 g (2.4 moles) of aminopropyltrimethoxysilane, 2.43 liters of toluene, 1.365 liters (14.43 moles) of methyl ethyl ketoxime and 170 mg of calcium oxide. The entire reaction system should be under the protection of inert gas to prevent the generation of by-products. Before heating, the pressure of the system was adjusted to 350 to 500 mmHg by a pressure controller. And heating the reaction mixture under this pressure until reflux, control the temperature of the reflux head between 35 degrees Celsius and 80 degrees Celsius, after heating for 8 hours, obtain 435 grams of distilled light components, flow out into the rece...

example 2

[0029] Using the same preparation method as in Example 1, 1.2 kg (16.5 moles) of acetone oxime, 478 milliliters (2.74 moles) of aminopropyltrimethoxysilane, 2.35 liters of toluene and 180 mg of calcium oxide were added.

example 3

[0031] Using the same preparation method as in Example 1, 1 kg (11.5 moles) of butanone oxime, 414 milliliters (1.92 moles) of (trimethoxysilylpropyl) ethylenediamine, 1.98 liters of toluene and 150 mg of calcium oxide were added.

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Abstract

The invention provides a method for preparing hydroxyimino organosilicon compounds, which comprises the steps as follows: firstly, the mixture comprising RaSi(OR1)4-a and HON(R2)(R3) is heated; and secondly, by-products are removed under pressure-relief condition, wherein R refers to straight-chain or branched or ring-shaped saturated or unsaturated alkanes or aromatics or organic hydrocarbon containing other substituent groups, and the alkanes comprise 1 to 20 carbons; R1 refers to the alkanes comprising 1 to 6 carbons, and comprises methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl; R2 and R3 are the same or different alkanes comprising 0 to 10 carbons; and a is an integer ranging from 0 to 3. The preparation process cannot generate acidic materials so as to eliminate potential safety hazards, can also lead the reaction to be performed effectively, improves the effectiveness and the conversion rate of the reaction, reduces the reaction temperature, shortens the reaction time, can be used for preparing hydroxyimino organosilan, and is particularly suitable for synthesizing hydroxyimino silane that has high reaction activity and is sensitive to temperature.

Description

technical field [0001] The invention relates to a preparation method of an oxime-based organosilicon compound. The oxime-based organosilicon compound can be used as a crosslinking agent, a coupling agent and an additive for sealants or other industries. Background technique [0002] Oxime-based organosilicon compounds can be used as cross-linking agents, coupling agents and functional additives to cure and cross-link silicone materials, or to improve and adjust other properties; room temperature-curable silicone materials can be exposed to In the atmosphere, it reacts with water in the air to cross-link and solidify to become an elastomer, and in the case of isolation from water, it is stable in storage; this type of product is generally achieved by mixing a certain proportion of diorganopolysiloxane and cross-linking agent ; The silicone crosslinking agent has multiple hydrolyzable groups, such as alkoxy, oxime, amine, carboxyl, etc.; in addition, in many cases, according t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/18
Inventor 刘川林新松王兵翟海潮李印柏
Owner TONSAN ADHESIVES INC