A kind of organic silicon compound and its preparation method and application

Abstract

The present application relates to a kind of organosilicon compounds and its preparation method and application.The preparation method of the organosilicon compound of the present application is: by raw material heptamethyltrisiloxane and maleic acid derivative, in the presence of catalyst, carry out silicon hydrogen addition reaction preparation and form.The organosilicon compound prepared in the present application has excellent wetting and permeability, can effectively improve the wetting and permeability of product, thereby improve the use effect and user experience of product.

Description

Technical Field

[0001] This invention relates to the field of organosilicon technology, and in particular to an organosilicon compound, its preparation method, and its application. Background Technology

[0002] Siloxane compounds are widely used in various products due to their excellent thermal and chemical stability. Heptamethyltrisiloxane is a common siloxane compound, with a structure consisting of three silicon atoms and seven methyl groups. This unique structure endows it with good thermal and chemical stability. Furthermore, heptamethyltrisiloxane can impart a silky feel to solid-liquid interfaces and improve the spreadability of products, thus finding widespread use in the cosmetics, textiles, and leather industries. Maleic acid derivatives are important organic compounds that can be used as stabilizers, antistatic agents, and emulsifiers. Simultaneously, due to the variability of their diester structure, maleic acid derivatives also have wide applications in agriculture.

[0003] While heptamethyltrisiloxane and maleic acid derivatives have addressed some of the problems of existing technologies to a certain extent, other issues remain. Existing technologies primarily utilize the properties of heptamethyltrisiloxane and maleic acid derivatives separately, without fully leveraging their synergistic effect, thus limiting their application effectiveness.

[0004] Furthermore, hydrosilylation is an important chemical reaction that can yield different products by changing the reaction conditions and reactants. Although hydrosilylation can produce new compounds, it requires specific reaction conditions and equipment, such as high-temperature and high-pressure reactors, which may increase production costs and technical difficulty. Summary of the Invention

[0005] To address the above technical problems, this invention provides an organosilicon compound that can improve wetting properties, its preparation method, and its application.

[0006] To achieve the technical effects of this invention, the following technical solution is adopted:

[0007] A method for preparing an organosilicon compound, comprising: reacting heptamethyltrisiloxane and a maleic acid derivative in the presence of a catalyst via a hydrosilylation reaction. Specifically, the organosilicon compound is prepared by a hydrosilylation reaction.

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

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

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

[0011] 1) Add the raw material heptamethyltrisiloxane and maleic acid derivative to a container and mix them evenly at a molar ratio of 1:1.03 to 1.07; a molar ratio of heptamethyltrisiloxane and maleic acid derivative of 1:1.03 to 1.07 can make the reaction more complete.

[0012] 2) Add a catalyst to the well-mixed raw materials to obtain a mixture;

[0013] 3) Heat the mixture to 120-150℃ to carry out a hydrosilylation reaction to obtain the reaction product.

[0014] As a further improvement, the preparation method also includes the following steps: distilling off the unreacted raw materials and catalyst from the reaction product under reduced pressure to obtain the final product.

[0015] As a further improvement, the distillation temperature is 60-80℃ and the pressure is 0.01-0.05MPa. With a suitable distillation temperature, the product is less likely to deteriorate. Alternatively, the container can be cooled to room temperature, the reaction product removed, and then distilled under reduced pressure at 60-80℃.

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

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

[0018] The present invention also provides an organosilicon compound prepared by the method described above.

[0019] The present invention also provides the application of the above-described organosilicon compounds as wetting and penetrating agents.

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

[0021] This invention yields a novel organosilicon compound by hydrosilylation reaction of heptamethyltrisiloxane and maleic acid derivative. This compound not only retains the thermal and chemical stability of heptamethyltrisiloxane but also combines the wetting and penetrating properties of maleic acid derivative, achieving a synergistic effect between the two. This results in a new structure with excellent wetting and penetrating properties, which can effectively improve the wetting and penetrating properties of the product, thereby enhancing the product's performance and user experience.

[0022] Compared to existing technologies that require the separate use of heptamethyltrisiloxane and maleic acid derivatives, this invention obtains organosilicon compounds through a one-step reaction, simplifying the production process and reducing production costs and technical difficulties.

[0023] While existing hydrosilylation reactions can yield new compounds, they require specific reaction conditions and equipment, such as high-temperature and high-pressure reactors, which can increase production costs and technical difficulties. The hydrosilylation reaction of this invention can be performed using an atmospheric pressure device, resulting in lower production costs and lower technical barriers.

[0024] In summary, compared with the prior art, the present invention achieves synergistic effects, simplifies the process, and improves wetting and penetration performance. Detailed Implementation

[0025] Example 1

[0026] 1) Add 1 mol of heptamethyltrisiloxane and 1.07 mol of diisooctyl maleate to the reaction vessel and stir with an electric stirrer at 500 rpm for 30 minutes to ensure that the raw materials are fully mixed.

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

[0028] 3) Heat the mixture to 150°C and stir for 2 hours to obtain the reaction product; carry out the hydrosilylation reaction under these conditions;

[0029] 4) Cool the reactor to room temperature and remove the reaction product;

[0030] 5) Using a rotary evaporator under reduced pressure (pressure 0.01 MPa), distill (temperature 60℃) the unreacted raw materials and catalyst in the reaction products to obtain the final product.

[0031] The chemical equation for this reaction is:

[0032]

[0033] Example 2

[0034] 1) Add 1 mol of heptamethyltrisiloxane and 1.07 mol of dibutyl maleate to the reaction vessel and stir with an electric stirrer at 500 rpm for 30 minutes to ensure that the raw materials are fully mixed.

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

[0036] 3) Heat the mixture to 150°C and stir for 2 hours to obtain the reaction product; carry out the hydrosilylation reaction under these conditions;

[0037] 4) Cool the reactor to room temperature and remove the reaction product;

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

[0039] Example 3

[0040] 1) Add 1 mol of heptamethyltrisiloxane and 1.03 mol of maleic acid isotridecyl ester to the reaction vessel and stir with an electric stirrer at 500 rpm for 30 minutes to ensure that the raw materials are fully mixed.

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

[0042] 3) Heat the mixture to 120°C and stir for 2 hours to obtain the reaction product; carry out the hydrosilylation reaction under these conditions;

[0043] 4) Cool the reactor to room temperature and remove the reaction product;

[0044] 5) Using a rotary evaporator under reduced pressure (pressure 0.05 MPa), distill (temperature 80℃) the unreacted raw materials and catalyst in the reaction products to obtain the final product.

[0045] Example 4

[0046] 1) Add 1 mol of heptamethyltrisiloxane and 1.07 mol of maleic acid isotridecyl alcohol polyether ester to the reactor and stir with an electric stirrer at 500 rpm for 30 minutes to ensure that the raw materials are fully mixed.

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

[0048] 3) Heat the mixture to 120°C and stir for 4 hours to obtain the reaction product; carry out the hydrosilylation reaction under these conditions;

[0049] 4) Cool the reactor to room temperature and remove the reaction product;

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

[0051] Comparative Example 1

[0052] 1) Add 1 mol of heptamethyltrisiloxane and 1.07 mol of diisooctyl maleate to the reaction vessel and stir with an electric stirrer at 500 rpm for 30 minutes to ensure that the raw materials are fully mixed and homogeneous.

[0053] 2) Stir the mixture for 2 hours to obtain sample 1.

[0054] Comparative Example 2

[0055] 1) Add 1 mol of heptamethyltrisiloxane and 1.07 mol of dibutyl maleate to the reaction vessel and stir with an electric stirrer at 500 rpm for 30 minutes to ensure that the raw materials are fully mixed and homogeneous to obtain a mixture; wherein, the molar ratio of heptamethyltrisiloxane to dibutyl maleate is 1:1.07.

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

[0057] Comparative Example 3

[0058] 1) Add 1 mol of heptamethyltrisiloxane and 1.03 mol of maleic acid isotridecyl ester to the reaction vessel and stir with an electric stirrer at 500 rpm for 30 minutes to ensure that the raw materials are fully mixed and homogeneous to obtain a mixture.

[0059] 2) Stir the mixture for 2 hours to obtain sample 3.

[0060] Comparative Example 4

[0061] 1) Add 1 mol of heptamethyltrisiloxane and 1.07 mol of maleic acid isotridecyl alcohol polyether ester to the reaction vessel, and stir with an electric stirrer at 500 rpm for 30 minutes to ensure that the raw materials are fully mixed and homogeneous to obtain a mixture.

[0062] 2) Stir the mixture for 4 hours to obtain sample 4.

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

[0064] In Examples 1-4, step 3) can be carried out under normal pressure with stirring.

[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) can be to load the reaction product into a rotary evaporator and use the rotary evaporator to distill off the 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) was carried out at room temperature.

[0068] In this application, or in the examples and comparative examples, the raw materials are heptamethyltrisiloxane and maleic acid derivatives. For example, in Example 3, it is 1 mol heptamethyltrisiloxane and 1.03 mol maleic acid isotridecyl ester.

[0069] Application performance testing:

[0070] Using a dynamic surface tension instrument, the surface tension of the final products obtained in Examples 1-4, heptamethyltrisiloxane, diisooctyl maleate, dibutyl maleate, isotretinoin maleate, isotretinoin maleate polyether ester, and samples 1-4 (1000 times diluted aqueous solution) was tested using the rapid bubble method of GB / T 27842-2011, determination of dynamic surface tension of chemicals. The tested surface tension and the time required to reach equilibrium are shown in Table 1.

[0071] Table 1

[0072]

[0073]

[0074] As can be seen from Table 1, the surface tension of the final products obtained in Examples 1-4 is lower than that of the corresponding comparative examples 1-4, indicating that the organosilicon compounds prepared in this invention have excellent wetting and penetrating properties. Furthermore, the surface tension of the final products obtained in Examples 1-4 is also lower than that of heptamethyltrisiloxane, diisooctyl maleate, dibutyl maleate, isotretinoin maleate, and isotretinoin polyether maleate, resulting in unexpected technical effects.

[0075] The time required for the final products obtained in Examples 1-4 to reach equilibrium was significantly shorter than that required for Comparative Examples 1-4, heptamethyltrisiloxane, diisooctyl maleate, dibutyl maleate, isotretinoin maleate, and isotretinoin polyether maleate. This indicates that the organosilicon compounds obtained in Examples 1-4 spread easily on surfaces and have excellent wetting properties. If applied in agriculture, when pesticides using the final products of Examples 1-4 as wetting and penetrating agents are sprayed onto leaves, the liquid spreads quickly, preventing the product from dripping onto the ground and thus saving on product usage.

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

[0077] In Examples 1, 2, and 4 of this invention, heptamethyltrisiloxane and maleic acid derivatives can be added to a reaction vessel at a molar ratio of 1:1.07 for reaction; in Example 3, heptamethyltrisiloxane and maleic acid derivatives can be added to a reaction vessel at a molar ratio of 1:1.03 for reaction, and the results of product application performance tests are basically the same.

[0078] The organosilicon compounds prepared by this invention can be widely applied in materials science and engineering, chemical engineering and technology, and other fields. Firstly, this technical solution, through a hydrosilylation reaction of heptamethyltrisiloxane and maleic acid derivatives, yields a novel structure with excellent wetting and penetrating properties. This will greatly improve the product's performance and user experience, especially in industries such as cosmetics, textiles, leather, and agriculture, where it is expected to find wider applications. Secondly, by fully utilizing the synergistic effect of heptamethyltrisiloxane and maleic acid derivatives, the surface tension (mN / m) and equilibrium time (ms) of the product after hydrosilylation are significantly lower than those of heptamethyltrisiloxane, mixtures of heptamethyltrisiloxane and other maleic acid derivatives, or maleic acid derivatives. The cost of combining maleic esters is also much lower than that of heptamethyltrisiloxane. The hydrosilylation product can reduce usage costs, which is highly attractive to enterprises. Finally, the implementation of this technical solution can promote technological progress and industrial development in related fields, and is of great significance for promoting scientific and technological progress and economic development.

[0079] The above description is merely a preferred embodiment of the present invention and should not be construed as limiting the scope of the invention. Any simple equivalent changes and modifications made in accordance with the claims and specification of the present invention shall still fall within the scope of the claims. Furthermore, the abstract and headings are merely for assisting in patent document searching and are not intended to limit the scope of the present invention.

Claims

1. A method for preparing an organosilicon compound, characterized in that, Its preparation method is as follows: it is prepared by hydrosilylation reaction of raw material heptamethyltrisiloxane and maleic acid derivative in the presence of catalyst; The maleic acid derivative is one or more of diisooctyl maleate, dibutyl maleate, isotretinoin maleate, and isotretinoin polyether maleate; the method for preparing the organosilicon compound includes the following steps: 1) Add the raw material heptamethyltrisiloxane and maleic acid derivative into a container at a molar ratio of 1:1.03 to 1.07 and mix thoroughly; 2) Add a catalyst to the well-mixed raw materials to obtain a mixture; 3) Heat the mixture to 120-150℃ to carry out a hydrosilylation reaction to obtain the reaction product.

2. The method for preparing the organosilicon compound according to claim 1, characterized in that, The catalyst is One or both of the following: Karstedt catalyst and chloroplatinic acid.

3. The method for preparing the organosilicon compound according to claim 1, characterized in that, The preparation method also includes the following steps: distilling off the unreacted raw materials and catalyst from the reaction products under reduced pressure to obtain the final product.

4. The method for preparing the organosilicon compound as described in claim 3, characterized in that, During distillation, the temperature is 60-80℃ and the pressure is 0.01-0.05MPa.

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

6. The method for preparing the organosilicon compound according to claim 1, characterized in that... The container is a reaction vessel; step 3) is a hydrosilylation reaction carried out under normal pressure; the hydrosilylation reaction time is 2-4 hours; the reaction is carried out under stirring conditions.

7. An organosilicon compound, characterized in that, It is prepared by the method for preparing the organosilicon compound according to any one of claims 1-6.

8. The application of the organosilicon compound as described in claim 7, characterized in that, The organosilicon compound is used as a wetting and penetrating agent.

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