Organosilicon compound and preparation method and application thereof

Abstract

The invention relates to an organosilicon compound and a preparation method and application thereof. The preparation method of the organosilicon compound comprises the step of carrying out hydrosilylation reaction on raw materials of heptamethyltrisiloxane and a maleic acid derivative in the presence of a catalyst. The organosilicon compound prepared by the invention has excellent wetting and penetrating performance, and the wetting and penetrating performance of a product can be effectively improved, so that the use effect and user experience of the product are improved.

Description

Technical Field

[0001] The present invention relates to the technical field of organosilicon, and in particular to an organosilicon compound and a preparation method and application thereof. Background Art

[0002] Siloxane compounds are widely used in various products due to their excellent thermal and chemical stability. Among them, heptamethyltrisiloxane is a common siloxane compound, and its structure consists of three silicon atoms and seven methyl groups. This special structure gives it good thermal and chemical stability. In addition, heptamethyltrisiloxane can also give the solid-liquid contact surface a silky touch and improve the ductility of the product. Therefore, it is widely used in the cosmetics, textiles, leather and other industries. Maleic acid derivatives are an important organic compound that can be used as stabilizers, antistatic agents and emulsifiers. At the same time, due to the variability of its diester structure, maleic acid derivatives are also widely used in agriculture.

[0003] Although heptamethyltrisiloxane and maleic acid derivatives have solved some problems of the prior art to a certain extent, other problems still exist. The prior art mainly uses the characteristics of heptamethyltrisiloxane and maleic acid derivatives separately, but does not fully utilize the synergistic effect of the two, thereby limiting the application effect.

[0004] In addition, the hydrosilylation reaction is an important chemical reaction that can produce different products by changing the reaction conditions and raw materials. Although the hydrosilylation reaction can produce new compounds, the reaction requires special reaction conditions and equipment, such as a high-temperature and high-pressure reactor, which may increase production costs and technical difficulties. Summary of the invention

[0005] In order to solve the above technical problems, the present invention provides an organosilicon compound capable of improving wetting performance, and a preparation method and application thereof.

[0006] In order to achieve the technical effects of the present invention, the following technical solutions are adopted:

[0007] A method for preparing an organosilicon compound comprises: preparing the organosilicon compound by carrying out a hydrosilylation reaction of raw materials heptamethyltrisiloxane and a maleic acid derivative in the presence of a catalyst. That is, the organosilicon compound is prepared by carrying out a hydrosilylation reaction.

[0008] As a further improvement, the maleic acid derivative is one or more of diisooctyl maleate, dibutyl maleate, isomeric tridecyl maleate, and isomeric tridecyl maleate polyether ester.

[0009] As a further improvement, the catalyst is one or both of Kar Stedt catalyst and chloroplatinic acid.

[0010] As a further improvement, the preparation method comprises the following steps:

[0011] 1) Add the raw materials heptamethyltrisiloxane and maleic acid derivative in a molar ratio of 1:1.03-1.07 into a container and mix them evenly; the molar ratio of heptamethyltrisiloxane and maleic acid derivative is 1:1.03-1.07, which can make the reaction more complete.

[0012] 2) adding a catalyst to the uniformly mixed raw materials to obtain a mixture;

[0013] 3) The mixture is heated to 120-150° C. to carry out a hydrosilylation reaction to obtain a reaction product.

[0014] As a further improvement, the preparation method further comprises the following steps: distilling out unreacted raw materials and catalysts in the reaction product under reduced pressure to obtain a final product.

[0015] As a further improvement, during distillation, the temperature is 60-80°C and the pressure is 0.01-0.05MPa. The distillation temperature is appropriate and the product is not easy to deteriorate. The container can be cooled to room temperature, the reaction product is taken out, and then vacuum distillation is performed at 60-80°C.

[0016] As a further improvement, the added amount of the catalyst is 0.05-0.1% of the total mass of the raw materials.

[0017] As a further improvement, the container is a reactor; the step 3) is to carry out the hydrosilylation reaction under normal pressure; the hydrosilylation reaction time is 2-4 hours; and the reaction is carried out under stirring conditions.

[0018] The present invention also provides an organosilicon compound prepared by the above-mentioned method for preparing the organosilicon compound.

[0019] The present invention also provides the use of the above-mentioned organosilicon compound as a wetting and penetrating agent.

[0020] The present invention has the following beneficial effects:

[0021] The present invention obtains a new organosilicon compound by subjecting heptamethyltrisiloxane and a maleic acid derivative to a hydrosilylation reaction. The compound not only retains the thermal stability and chemical stability of heptamethyltrisiloxane, but also combines the wetting and penetration properties of the maleic acid derivative, thereby achieving a synergistic effect of the two and obtaining a new structure with excellent wetting and penetration properties, which can effectively improve the wetting and penetration properties of the product, thereby improving the use effect and user experience of the product.

[0022] Compared with the prior art which requires the use of heptamethyltrisiloxane and maleic acid derivatives respectively, the present invention obtains the organosilicon compound through a one-step reaction, simplifies the production process, and reduces the production cost and technical difficulty.

[0023] Although the hydrosilylation reaction in the prior art can produce new compounds, the reaction requires special reaction conditions and equipment, such as a high-temperature and high-pressure reactor, which may increase production costs and technical difficulties. The production equipment for the hydrosilylation reaction of the present invention can be a normal pressure device, which has lower production costs and technical barriers.

[0024] In general, compared with the prior art, the present invention achieves synergistic effect, simplifies the process and improves the wetting and penetration performance. DETAILED DESCRIPTION

[0025] Example 1

[0026] 1) Add 1 mol of heptamethyltrisiloxane and 1.07 mol of diisooctyl maleate into a reaction kettle, and stir at 500 rpm for 30 minutes using an electric stirrer to mix the raw materials thoroughly;

[0027] 2) adding chloroplatinic acid as a catalyst to the uniformly mixed raw materials to obtain a mixture; the added mass of the chloroplatinic acid is 0.05% of the total mass of the raw materials;

[0028] 3) heating the mixture to 150° C. and stirring for 2 hours to obtain a reaction product; and performing a hydrosilylation reaction under this condition;

[0029] 4) Cooling the reactor to room temperature and taking out the reaction product;

[0030] 5) Using a rotary evaporator under reduced pressure (pressure of 0.01 MPa), the unreacted raw materials and catalyst in the reaction product were distilled (temperature of 60° C.) to obtain the final product.

[0031] The chemical reaction formula of this reaction is:

[0032]

[0033] Example 2

[0034] 1) Add 1 mol of heptamethyltrisiloxane and 1.07 mol of dibutyl maleate into a reaction kettle, and stir at 500 rpm for 30 minutes using an electric stirrer to fully mix the raw materials;

[0035] 2) adding chloroplatinic acid as a catalyst to the uniformly mixed raw materials to obtain a mixture; the added mass of the chloroplatinic acid is 0.1% of the total mass of the raw materials;

[0036] 3) heating the mixture to 150° C. and stirring for 2 hours to obtain a reaction product; and performing a hydrosilylation reaction under this condition;

[0037] 4) Cooling the reactor to room temperature and taking out the reaction product;

[0038] 5) Using a rotary evaporator under reduced pressure (pressure of 0.01 MPa), the unreacted raw materials and catalyst in the reaction product were distilled (temperature of 60° C.) to obtain the final product.

[0039] Example 3

[0040] 1) Add 1 mol of heptamethyltrisiloxane and 1.03 mol of isomeric tridecyl maleate into a reaction kettle, and stir at 500 rpm for 30 minutes using an electric stirrer to fully mix the raw materials;

[0041] 2) adding chloroplatinic acid as a catalyst to the uniformly mixed raw materials to obtain a mixture; the added mass of the chloroplatinic acid is 0.1% of the total mass of the raw materials;

[0042] 3) heating the mixture to 120° C. and stirring for 2 hours to obtain a reaction product; and performing a hydrosilylation reaction under this condition;

[0043] 4) Cooling the reactor to room temperature and taking out the reaction product;

[0044] 5) Using a rotary evaporator under reduced pressure (pressure of 0.05 MPa), the unreacted raw materials and catalyst in the reaction product were distilled (temperature of 80° C.) to obtain the final product.

[0045] Example 4

[0046] 1) Add 1 mol of heptamethyl trisiloxane and 1.07 mol of maleic acid isomeric tridecanol polyether ester into a reaction kettle, and stir at a speed of 500 rpm for 30 minutes using an electric stirrer to fully mix the raw materials;

[0047] 2) adding a karstedt catalyst to the uniformly mixed raw materials to obtain a mixture; the added mass of the karstedt catalyst is 0.1% of the total mass of the raw materials;

[0048] 3) heating the mixture to 120° C. and stirring for 4 hours to obtain a reaction product; and performing a hydrosilylation reaction under this condition;

[0049] 4) Cooling the reactor to room temperature and taking out the reaction product;

[0050] 5) Using a rotary evaporator under reduced pressure (pressure of 0.01 MPa), the unreacted raw materials and catalyst in the reaction product were distilled (temperature of 60° C.) to obtain the final product.

[0051] Comparative Example 1

[0052] 1) adding 1 mol of heptamethyltrisiloxane and 1.07 mol of diisooctyl maleate into a reaction kettle, and stirring at 500 rpm for 30 minutes with an electric stirrer to fully mix the raw materials to obtain a mixture;

[0053] 2) The mixture was stirred for 2 hours to obtain sample 1.

[0054] Comparative Example 2

[0055] 1) adding 1 mol of heptamethyltrisiloxane and 1.07 mol of dibutyl maleate into a reaction kettle, and stirring at 500 rpm for 30 minutes with an electric stirrer to fully mix the raw materials to obtain a mixture; wherein the molar ratio of heptamethyltrisiloxane to dibutyl maleate is 1:1.07;

[0056] 2) stirring the mixture for 2 hours to obtain sample 2;

[0057] Comparative Example 3

[0058] 1) adding 1 mol of heptamethyltrisiloxane and 1.03 mol of isomeric tridecanol maleate into a reaction kettle, and stirring at a speed of 500 rpm for 30 minutes with an electric stirrer to fully mix the raw materials to obtain a mixture;

[0059] 2) The mixture was stirred for 2 hours to obtain sample 3.

[0060] Comparative Example 4

[0061] 1) adding 1 mol of heptamethyltrisiloxane and 1.07 mol of maleic acid isomeric tridecanol polyether ester to a reaction kettle, and stirring at a speed of 500 rpm for 30 minutes with an electric stirrer to fully mix the raw materials to obtain a mixture;

[0062] 2) The mixture was stirred for 4 hours to obtain sample 4.

[0063] In Examples 1-4, the stirring in step 3) can be carried out at a speed of 500 rpm.

[0064] In Examples 1-4, step 3) may be carried out by stirring the reaction under normal pressure.

[0065] In Examples 1-4, when the pressure is 0.01 MPa, the distillation time can be 0.5 hours, and when the pressure is 0.05 MPa, the distillation time can be 1 hour.

[0066] In Examples 1-4, step 5) may be to load the reaction product into a rotary evaporator, and use the rotary evaporator to distill out unreacted raw materials and catalyst in the reaction product under reduced pressure to obtain the final product.

[0067] In Comparative Examples 1-4, the stirring in step 2) is carried out at room temperature.

[0068] In the present application or in the examples and comparative examples, the raw materials are heptamethyltrisiloxane and a maleic acid derivative. For example, in Example 3, 1 mol of heptamethyltrisiloxane and 1.03 mol of isomeric tridecyl maleate are used.

[0069] Application performance testing:

[0070] A dynamic surface tension instrument was used to test the surface tension of the final product obtained in Examples 1-4, heptamethyl trisiloxane, diisooctyl maleate, dibutyl maleate, isotridecyl maleate, isotridecyl maleate polyether maleate and samples 1-4 (1000 times diluted aqueous solution) using the rapid bubble method for determination of dynamic surface tension of chemicals in accordance with GB / T 27842-2011. The surface tension of the test and the time required to reach equilibrium are shown in Table 1.

[0071] Table 1

[0072]

[0073]

[0074] From Table 1, it can be seen that the surface tension of the final products obtained in Examples 1-4 is less than the surface tension of Samples 1-4 prepared in the corresponding Comparative Examples 1-4, indicating that the organosilicon compound prepared in the present invention has good wetting and penetration properties. At the same time, the surface tension of the final products obtained in Examples 1-4 is also less than the surface tension of heptamethyltrisiloxane, diisooctyl maleate, dibutyl maleate, isomeric tridecanol maleate and isomeric tridecanol maleate polyether ester, producing unexpected technical effects.

[0075] The time required for the final product obtained in Example 1-4 to reach equilibrium is significantly shorter than that of Comparative Example 1-4, heptamethyl trisiloxane, diisooctyl maleate, dibutyl maleate, isotridecyl maleate and isotridecyl maleate polyether ester, indicating that the organosilicon compound obtained in Example 1-4 is easy to spread on the surface and has good wetting properties. If this substance is used in agriculture, when the pesticide using the final product obtained in Example 1-4 as a wetting and penetrating agent is sprayed on leaves, the liquid can be spread quickly, and it is not easy for the product to fall to the ground, thereby saving the amount of the product.

[0076] The surface tension of the newly synthesized substance is lower. The reason may be that after the new substance is synthesized by reaction, the new substance contains hydrophilic groups and lipophilic groups, that is, it has both hydrophilic and hydrophobic (lipophilic) properties. This property enables the molecules to form a directional arrangement on the surface of the liquid, thereby reducing the surface tension of the liquid.

[0077] In Example 1.2.4 of the present invention, heptamethyltrisiloxane and a maleic acid derivative may be added to a reactor at a molar ratio of 1:1.07 for reaction; in Example 3, heptamethyltrisiloxane and a maleic acid derivative may be added to a reactor at a molar ratio of 1:1.03 for reaction, and the product application performance test results are basically the same.

[0078] The organosilicon compound prepared by the present invention can be widely used in application fields such as materials science and engineering, chemical engineering and technology. First, the present technical solution obtains a new structure with excellent wetting and penetration properties by subjecting heptamethyl trisiloxane and maleic acid derivatives to hydrosilylation reaction, which will greatly improve the use effect and user experience of the product, especially in the industries of cosmetics, textiles, leather, agriculture, etc., and is expected to be more widely used. Secondly, the present technical solution makes full use of the synergistic effect of heptamethyl trisiloxane and maleic acid derivatives. After hydrosilylation, the surface tension mN / m and the time required to reach equilibrium / ms of the product are much lower than heptamethyl trisiloxane or a mixture of heptamethyl trisiloxane and other maleic acid derivatives or maleic acid derivatives. The cost of combining maleic acid esters is also much lower than heptamethyl trisiloxane. The hydrosilylation product can reduce the cost of use, which is very attractive to enterprises. Finally, the implementation of the present technical solution can promote technological progress and industrial development in related fields, which is of great significance for promoting scientific and technological progress and economic development.

[0079] The above is only a preferred embodiment of the present invention, and it cannot be used to limit the scope of the present invention. That is, all simple equivalent changes and modifications made according to the contents recorded in the claims and the invention specification are still within the scope of the claims of the present invention. In addition, the abstract and title are only used to assist in searching patent documents, and are not used to limit the scope of the rights of the present invention.

Claims

1. A method for preparing an organosilicon compound, It is characterized in that The preparation method is as follows: raw materials heptamethyltrisiloxane and maleic acid derivatives are subjected to hydrosilylation reaction in the presence of a catalyst to prepare the product.

2. The method for preparing the organosilicon compound according to claim 1, It is characterized in that The maleic acid derivative is one or more of diisooctyl maleate, dibutyl maleate, isomeric tridecyl maleate, and isomeric tridecyl maleate polyether ester.

3. The method for preparing the organosilicon compound according to claim 1, It is characterized in that The catalyst is one or both of a karstedt catalyst and chloroplatinic acid.

4. The method for preparing the organosilicon compound according to claim 1, It is characterized in that The preparation method comprises the following steps: 1) adding raw materials heptamethyltrisiloxane and maleic acid derivative into a container at a molar ratio of 1:1.03-1.07 and mixing them evenly; 2) adding a catalyst to the uniformly mixed raw materials to obtain a mixture; 3) The mixture is heated to 120-150° C. to carry out a hydrosilylation reaction to obtain a reaction product.

5. The method for preparing the organosilicon compound according to claim 1, It is characterized in that The preparation method also includes the following steps: distilling out unreacted raw materials and catalysts in the reaction product under reduced pressure to obtain the final product.

6. The method for preparing the organosilicon compound according to claim 5, It is characterized in that During distillation, the temperature is 60-80°C and the pressure is 0.01-0.05MPa.

7. The method for preparing the organosilicon compound according to claim 1, Features , the amount of the catalyst added is 0.05-0.1% of the total mass of the raw materials.

8. The method for preparing the organosilicon compound according to claim 4, Features , the container is a reactor; the step 3) is to carry out a hydrosilylation reaction under normal pressure; the hydrosilylation reaction time is 2-4 hours; the reaction is carried out under stirring conditions.

9. An organosilicon compound, It is characterized in that The organic silicon compound is prepared by the method for preparing the organic silicon compound according to any one of claims 1 to 8.

10. Use of the organosilicon compound as claimed in claim 9, It is characterized in that The organosilicon compound is used as a wetting and penetrating agent.

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