CN106700080B - Modified silicone oil containing carboxylic betaine zwitter ion precursor, preparation method thereof and organic silicon material - Google Patents

Abstract

The invention discloses a modified silicone oil containing carboxybetaine zwitterion precursors, a preparation method thereof and an organic silicon material. Among them, the structural formula of the modified silicone oil is shown in formula I (0<n≤800): The organosilicon material prepared by the modified silicone oil of the present invention through cross-linking and film-forming reaction has good anti-protein non-specific adsorption properties and water resistance.

Description

A kind of modified silicone oil containing carboxybetaine zwitterion precursor and preparation method thereof methods and silicone materials

technical field

The invention relates to a modified silicone oil containing a carboxybetaine zwitterion precursor, a preparation method thereof, and a corresponding organosilicon material.

Background technique

The non-specific adsorption of proteins on the surface of materials has always been an important problem in many fields, and it cannot be ignored in various aspects such as medical implants, drug carriers, ship coatings, and biosensors. In order to solve this series of problems, anti-protein nonspecific adsorption (nonfouling) materials came into being. Studies have found that anti-protein non-specific adsorption materials can not only effectively prevent the coagulation process in the blood contact system, but also can be applied to prevent human body rejection and clearance reactions caused by the adsorption process of biomacromolecules at a wide range of solid-liquid interfaces, bacteria Adsorption, and the generation of various biofouling phenomena, including the formation of biofilm, the growth of algae, and even the growth of shellfish adsorbed on the surface. Preventing bacterial adsorption and biofilm formation alone can buy valuable time in preventing infection from bioimplants.

In recent years, scientists and scholars have attached great importance to and popularized the research on nonfouling materials. However, the materials that can play a good role in practical applications are relatively limited. The polyethylene glycol (PEG) materials that were widely used before are also used in use. More and more limitations have emerged, so the research on zwitterionic materials has received more and more attention. Zwitterionic polymer materials are currently considered to be the most promising nonfouling materials, which include polybetaine materials that carry a positive charge and a negative charge on each unit and carry equal amounts of positive and negative charges on two different units. Charged polyampholyte materials fall into two categories. Different from the hydrophilic polymer material PEG, the zwitterionic polymer material does not rely on hydrogen bonds to combine with water molecules, but tightly binds water molecules through the solvation of ions, forming a dense hydration layer on the surface of the material, thus giving the material Anti-protein non-specific adsorption properties. The synthesis route of zwitterionic polymer materials is simple and convenient, the raw materials are abundant and easy to obtain, the application is wide, and the cost is low. With the deepening of its research, it has received more and more attention and recognition in recent years.

Ship antifouling coatings are an important aspect of the application of nonfouling materials. Traditional antifouling coatings, such as organotin and copper-containing compounds, are very toxic to the environment, so they are gradually abandoned by people. The rise of nonfouling materials can be effective It is an environmentally friendly anti-fouling coating for ships to solve the problem of environmental pollution caused by traditional coatings. However, its poor hydrophobicity and water resistance have always been the main reasons that limit its wide application.

Contents of the invention

The technical problem to be solved by the present invention is to provide a modified silicone oil containing carboxybetaine zwitterion precursor, its preparation method and organic silicon material.

The technical scheme adopted by the present invention to solve its technical problems is: the modified silicone oil containing carboxybetaine zwitterion precursors of the present invention has a structure as shown in the following formula I:

In Formula I, 0<n≤800.

The preparation method of modified silicone oil of the present invention comprises:

Step a: mixing the first compound having the structure shown in formula II, the second compound having the structure shown in formula III, the platinum-containing catalyst, the phenolic polymerization inhibitor and the first solvent, and performing hydrosilylation reaction to obtain The third compound with the structure shown in formula IV, in formula III and formula IV, 0<n≤800;

Step b: Mixing the third compound, the tin-containing catalyst, sarcosinate and the second solvent, and performing an epoxy group ring-opening reaction to obtain the modified silicone oil;

Further, in step a of the present invention, the molar ratio of the Si-H bond in the first compound to the second compound is 1:0.6-0.7, the first compound, the platinum-containing catalyst, and the phenolic polymerization inhibitor The mass ratio to the first solvent is 1:0.001-0.005:0.001-0.005:2-15, the reaction temperature of the hydrosilylation reaction is 80-110° C., and the reaction time is 4-8 hours.

Further, in step b of the present invention, the molar ratio of the sarcosinate to the epoxy group in the third compound is 1:1, and the reaction temperature of the ring-opening reaction of the epoxy group is 70 ~80°C, the reaction time is 8~12h.

Further, the sarcosinate described in the present invention is tert-butyl sarcosinate.

Further, the first compound of the present invention is allyl glycidyl ether, and the second compound is hydrogen-containing silicone oil.

Further, the tin-containing catalyst described in the present invention is stannous octanoate (Sn(Oct) ₂ ), the platinum-containing catalyst is a Karetedt platinum catalyst, and the phenolic polymerization inhibitor is 2,6-di-tert-butyl-4-methyl phenol.

The method for preparing the organosilicon material by utilizing the modified silicone oil of the present invention is as follows: the organosilicon material is obtained through cross-linking reaction of the modified silicone oil.

Furthermore, a volatile organic solvent without active hydrogen and a crosslinking agent are added to the modified silicone oil of the present invention, and the silicone material is obtained by curing after a crosslinking reaction.

Further, the crosslinking agent in the present invention is a molecule containing polyisocyanate groups.

Compared with prior art, the beneficial effect of the present invention is:

Based on the research and development of anti-protein non-specific adsorption materials, the present invention improves the defects of traditional zwitterionic polymer materials in terms of water resistance, and discloses a modified silicone oil containing carboxybetaine zwitterionic precursors and Its preparation method and application, the organosilicon material obtained after the modified silicone oil is cross-linked and cured to form a film, has good anti-protein non-specific adsorption properties and water resistance. details as follows:

(1) The traditional zwitterionic polymer material improves the long-term performance of PEG and has good anti-protein non-specific adsorption performance, but often has poor water resistance. When applied in an aqueous environment, water molecules can easily enter the material Internally, it will swell and deform, reduce mechanical strength, and change physical and chemical properties. For example, in the field of ship antifouling coatings, it is easy to cause the coating to swell and scratch easily, or even fall off from the surface of the hull. Due to its hydrophobic structure of siloxane, traditional organosilicon materials have excellent water resistance, good biological safety and chemical inertness, but lack the ability to resist the adsorption of proteins, cells and bacteria, so they are used in biological materials. There are still obvious deficiencies in the field. The modified silicone oil of the present invention not only provides the organosilicon main chain structure and easy cross-linking groups for the preparation of organosilicon materials, but also is rich in acid carboxybetaine zwitterion precursor esters, so that the organosilicon materials can be degraded through organosilicon The main chain structure is degraded, and the degradation products have better environmental and biocompatibility. However, the acid-rich carboxybetaine zwitterionic precursor esters can produce anti-nonspecific adsorption properties after hydrolysis. The organosilicon material of the present invention is based on the organosilicon hydrophobic main chain, and the side chain introduces a zwitterion precursor structure, and after cross-linking and forming a film, both good anti-protein non-specific adsorption performance and water resistance are taken into account. Its anti-protein non-specific adsorption performance is at the same level as that of polymethacrylic acid carboxybetaine zwitterion precursor ester and polyacrylic acid carboxybetaine zwitterion precursor ester, etc., while its water resistance is significantly improved.

(2) The organosilicon material of the present invention still maintains the main chain structure of the organosilicon material, so that it can retain the oxygen permeability and degradation ability of the organosilicon material. Compared with polymethacrylic acid carboxybetaine zwitterion precursor ester and polyacrylic acid carboxybetaine zwitterion precursor ester, it has better oxygen permeability and degradation ability.

Therefore, the modified silicone oil containing carboxybetaine zwitterion precursors of the present invention has broad application prospects in the research of ship antifouling coatings, biological materials, and the like.

Description of drawings

Fig. 1 is the nuclear magnetic spectrum of the third compound (epoxy-modified silicone oil) synthesized in embodiment 1;

Fig. 2 is the nuclear magnetic spectrogram of the organic silicone oil synthesized by embodiment 1;

Fig. 3 is a graph showing the test results of the anti-nonspecific protein adsorption performance of the organosilicon material synthesized in Example 5.

Detailed ways

The synthetic route of organosilicon material of the present invention is as follows:

A modified silicone oil containing carboxybetaine zwitterion precursors and its preparation method and application in the present invention will be described in detail below with specific examples.

Example 1:

(1) Hydrosilylation reaction of hydrogen-containing silicone oil: Add 13.38g (0.116mol, denoted as 1.5eq) of the first compound (allyl glycidyl ether), 55mg of Karstedt catalyst, and 66.9mg of polymerization inhibitor into a three-necked flask 2,6-di-tert-butyl-4-methylphenol (BHT) and 100g of anhydrous toluene, fully stirred evenly. Under the airtight condition of _N2 protection, preheat the temperature to 60°C, after 30min, raise the temperature to 80°C, stir, and slowly add 5.00g of the second compound (hydrogen-containing silicone oil) (containing Si-H bond 0.077mol, 1.0 eq, the 50g anhydrous toluene solution of structural formula as shown in formula III). The reaction was stirred for 5h to obtain a light yellow solution. The above-mentioned pale yellow solution was subjected to rotary evaporation, and the resulting viscous solution was precipitated twice in a methanol-water mixture (the volume ratio for the first time was V _methanol : V _water = 1:1, and the second time was V _methanol : V _water =1:2), precipitated with distilled water for the third time, and discarded the supernatant. Dissolve it in an appropriate amount of ethyl acetate, add anhydrous sodium sulfate and dry it. The insoluble matter was removed by suction filtration, and the filtrate was rotary evaporated at 30°C to remove the solvent, and the obtained oily liquid was the third compound. The third compound is epoxy-modified silicone oil. The ¹ H-NMR spectrum of the third compound in deuterated chloroform is shown in FIG. 1 . The peaks corresponding to each H atom in the product have been marked in Figure 1, and the unmarked peaks are impurity peaks. Among them, the peak at the chemical shift of 4.67ppm is the hydrogen atom on the Si-H bond left due to the incomplete hydrosilylation reaction. Compare this Figure 1 with the standard substance spectrum, and calculate the conversion rate of the hydrosilylation reaction according to the peak area. As can be seen from Figure 1, there are fewer impurity peaks, the impurity is mainly solvent ethyl acetate, and the reaction conversion rate is about 90%.

(2) Ring-opening reaction of epoxy group: fully dissolve 2.56g (0.0167mol, recorded as 1.5eq) tert-butyl sarcosine hydrochloride in 50mL DMF, add 3.37g (0.0333mol, 3.0eq) Ethylamine, white crystals were precipitated, and the insoluble matter was removed by suction filtration. The filtrate was placed in a 100 mL round bottom flask, 2.00 g (0.0111 mol, 1.0 eq) of the third compound and catalyst Sn(Oct) ₂ were added, and the reaction was stirred at 75° C. for 8 h to obtain a yellow solution. Use a rotary evaporator (65°C) to remove triethylamine and most of the DMF, and the viscous liquid obtained is the crude product of silicone oil. Dissolve the crude product in a small amount of dichloromethane, precipitate with ether 2-3 times, discard the supernatant, dissolve the lower precipitate in ethyl acetate, and add anhydrous sodium sulfate to dry. The insoluble matter was removed by suction filtration, and the filtrate was rotary evaporated at 30°C to remove the solvent, and the obtained viscous liquid was modified silicone oil. The ¹ H-NMR spectrum of the modified silicone oil in deuterated chloroform is shown in Figure 2. The peaks corresponding to the main hydrogen atoms in the product have been marked in Figure 2, and the impurity peaks and some methyl peaks have not been marked. The impurity peaks are mainly solvent ethyl acetate and dichloromethane. Example 2:

(1) Hydrosilylation reaction of hydrogen-containing silicone oil: add 13.38g (0.116mol, denoted as 1.5eq) of the first compound (allyl glycidyl ether), 13mg Karstedt catalyst, 13mg inhibitor 2 into a three-necked flask , 6-di-tert-butyl-4-methylphenol (BHT) and 17.84g of anhydrous toluene, fully stirred evenly. Under the airtight condition of _N2 protection, preheat the temperature to 65°C, after 30min, raise the temperature to 110°C, stir, slowly add 4.50g of the second compound (hydrogen-containing silicone oil) (containing Si-H bond 0.069mol, 0.9 eq, 8.92 g of anhydrous toluene solution shown in structural formula III). The reaction was stirred for 4h to obtain a light yellow solution. The above-mentioned pale yellow solution was subjected to rotary evaporation, and the resulting viscous solution was precipitated twice in a methanol-water mixture (the volume ratio for the first time was V _methanol : V _water = 1:1, and the second time was V _methanol : V _water =1:2), precipitated with distilled water for the third time, and discarded the supernatant. Dissolve it in an appropriate amount of ethyl acetate, add anhydrous sodium sulfate and dry it. The insoluble matter was removed by suction filtration, and the filtrate was rotary evaporated at 30°C to remove the solvent, and the obtained oily liquid was the third compound.

(2) Ring-opening reaction of epoxy group: fully dissolve 2.56g (0.0167mol, recorded as 1.5eq) tert-butyl sarcosine hydrochloride in 50mL DMF, add 3.37g (0.0333mol, 3.0eq) Ethylamine, white crystals were precipitated, and the insoluble matter was removed by suction filtration. The filtrate was placed in a 100 mL round bottom flask, 3.00 g (0.0167 mol, 1.5 eq) of the third compound and the catalyst Sn(Oct) ₂ were added, and the reaction was stirred at 70° C. for 12 h to obtain a yellow solution. Use a rotary evaporator (65°C) to remove triethylamine and most of the DMF, and the viscous liquid obtained is the crude product of silicone oil. Dissolve the crude product in a small amount of dichloromethane, precipitate with ether 2-3 times, discard the supernatant, dissolve the lower precipitate in ethyl acetate, and add anhydrous sodium sulfate to dry. The insoluble matter was removed by suction filtration, and the filtrate was rotary evaporated at 30°C to remove the solvent, and the viscous liquid obtained was the modified silicone oil.

Example 3:

(1) Hydrosilylation reaction of hydrogen-containing silicone oil: add 13.38g (0.116mol, denoted as 1.5eq) of the first compound (allyl glycidyl ether), 67mg Karstedt catalyst, 67mg inhibitor 2 into a three-necked flask , 6-di-tert-butyl-4-methylphenol (BHT) and 134g of anhydrous toluene, fully stirred evenly. Under the airtight condition of _N2 protection, preheat the temperature to 60°C, after 30min, raise the temperature to 80°C, stir, and slowly add 5.00g of the second compound (hydrogen-containing silicone oil) (containing Si-H bond 0.077mol, 1.0 eq, shown in structural formula III) 72g anhydrous toluene solution. The reaction was stirred for 8h to obtain a light yellow solution. The above-mentioned pale yellow solution was subjected to rotary evaporation, and the resulting viscous solution was precipitated twice in a methanol-water mixture (the volume ratio for the first time was V _methanol : V _water = 1:1, and the second time was V _methanol : V _water =1:2), precipitated with distilled water for the third time, and discarded the supernatant. Dissolve it in an appropriate amount of ethyl acetate, add anhydrous sodium sulfate and dry it. The insoluble matter was removed by suction filtration, and the filtrate was rotary evaporated at 30°C to remove the solvent, and the obtained oily liquid was the third compound.

(2) Ring-opening reaction of epoxy group: fully dissolve 2.56g (0.0167mol, recorded as 1.5eq) tert-butyl sarcosine hydrochloride in 50mL DMF, add 3.37g (0.0333mol, 3.0eq) Ethylamine, white crystals were precipitated, and the insoluble matter was removed by suction filtration. The filtrate was placed in a 100 mL round bottom flask, 3.00 g (0.0167 mol, 1.5 eq) of the third compound and the catalyst Sn(Oct) ₂ were added, and the reaction was stirred at 80° C. for 8 h to obtain a yellow solution. Use a rotary evaporator (65°C) to remove triethylamine and most of the DMF, and the viscous liquid obtained is the crude product of silicone oil. Dissolve the crude product in a small amount of dichloromethane, precipitate with ether 2-3 times, discard the supernatant, dissolve the lower precipitate in ethyl acetate, and add anhydrous sodium sulfate to dry. The insoluble matter was removed by suction filtration, and the filtrate was rotary evaporated at 30°C to remove the solvent, and the viscous liquid obtained was the modified silicone oil.

Example 4:

(1) Hydrosilylation reaction of hydrogen-containing silicone oil: add 13.38g (0.116mol, denoted as 1.5eq) of the first compound (allyl glycidyl ether), 40mg Karstedt catalyst, 40mg inhibitor 2 into a three-necked flask , 6-di-tert-butyl-4-methylphenol (BHT) and 100g of anhydrous toluene, fully stirred evenly. Under the airtight condition of _N2 protection, preheat the temperature to 60°C, after 30min, raise the temperature to 80°C, stir, and slowly add 6.00g of the second compound (hydrogen-containing silicone oil) (containing Si-H bond 0.092mol, 1.0 eq, shown in structural formula III) 50g anhydrous toluene solution. The reaction was stirred for 6h to obtain a light yellow solution. The above-mentioned pale yellow solution was subjected to rotary evaporation, and the resulting viscous solution was precipitated twice in a methanol-water mixture (the volume ratio for the first time was V _methanol : V _water = 1:1, and the second time was V _methanol : V _water =1:2), precipitated with distilled water for the third time, and discarded the supernatant. Dissolve it in an appropriate amount of ethyl acetate, add anhydrous sodium sulfate and dry it. The insoluble matter was removed by suction filtration, and the filtrate was rotary evaporated at 30°C to remove the solvent, and the obtained oily liquid was the third compound.

(2) Ring-opening reaction of epoxy group: fully dissolve 2.56g (0.0167mol, recorded as 1.5eq) tert-butyl sarcosine hydrochloride in 50mL DMF, add 3.37g (0.0333mol, 3.0eq) Ethylamine, white crystals were precipitated, and the insoluble matter was removed by suction filtration. The filtrate was placed in a 100 mL round bottom flask, 3.00 g (0.0167 mol, 1.5 eq) of the third compound and the catalyst Sn(Oct) ₂ were added, and the reaction was stirred at 80° C. for 8 h to obtain a yellow solution. Use a rotary evaporator (65°C) to remove triethylamine and most of the DMF, and the viscous liquid obtained is the crude product of silicone oil. Dissolve the crude product in a small amount of dichloromethane, precipitate with ether 2-3 times, discard the supernatant, dissolve the lower precipitate in ethyl acetate, and add anhydrous sodium sulfate to dry. The insoluble matter was removed by suction filtration, and the filtrate was rotary evaporated at 30°C to remove the solvent, and the viscous liquid obtained was the modified silicone oil.

Example 5:

(1) Preparation of coating film (ie, silicone material): Add 1.00 g of the silicone oil prepared in Example 1 and 2 mL of ethyl acetate into a 5 mL centrifuge tube, shake on a vortex mixer to fully dissolve it. Add 70 μg HDI to the centrifuge tube and mix by ultrasonic. The mixed solution is injected into the mold, and the ethyl acetate is volatilized and dried, so that it is fully formed into a film to obtain a coating (ie, a silicone material).

(2) Evaluation of the anti-protein non-specific adsorption performance of organosilicon materials: the organosilicon materials were evenly cut into square slices with a side length of about 5 mm, and hydrolyzed in 0.2 mol/L NaOH solution for different times. Measure and record the side lengths of each sample and tissue culture polystyrene (TCPS) sheet. The hydrolyzed samples and TCPS sheets were placed in a 24-well plate, 1 mL of PBS buffer solution with an HRP-IgG concentration of 1 μg/mL was added to each well, and placed on a horizontal shaker for 1 h. The samples were washed 5 times with PBS buffer solution, 1 mL each time, and placed in new wells. Prepare a disodium hydrogen phosphate-citric acid buffer solution with a concentration of 1 mg/mL o-phenylenediamine + 1 μL/mL 0.03% hydrogen peroxide, add 1 mL to each well, and add the same solution to another well as a blank control group, and place in a horizontal Shake on a shaker for 15 minutes for color reaction. Add 1 mL of 2 mol/L H ₂ SO ₄ solution to each well to terminate the reaction. 200 μL of each solution was added to a 96-well plate, and the absorbance (OD value) at 492 nm was detected with a microplate reader. The anti-protein non-specific adsorption of silicone materials is shown in Figure 3.

It can be seen from Figure 3 that the relative protein adsorption capacity of the organosilicon material before hydrolysis is about 78.9%. After being hydrolyzed in 0.2mol/L NaOH solution for 1 hour, a good anti-protein non-specific adsorption effect can be achieved, which is reduced to about 22.0%. When hydrolyzed for 3 hours, the best anti-protein adsorption effect can be achieved, which is about 18.2%. As the hydrolysis time continues to increase, it can still maintain a good anti-protein adsorption capacity within 4.5h, and when the hydrolysis time reaches 6h and above, the relative adsorption amount of protein begins to increase, which may be due to the long-term hydrolysis It is caused by the destruction of the zwitterionic structure of the organosilicon material. In general, silicone materials have excellent anti-protein non-specific adsorption ability after hydrolysis.

(3) Evaluation of the swelling performance of silicone materials: Cut the silicone materials synthesized in Application Example 1 into samples of appropriate size (about 5mm×5mm), soak them in PBS buffer solution with pH=7.4, and observe their swelling properties by taking regular photos. Changes in size, transparency, and other morphology should be monitored long-term. According to the morphology of the samples soaked in the PBS buffer solution of pH=7.4 for different time, it can be seen that the size of the samples after soaking for one month, two months, three months and six months compared with that before soaking (0month) , color, transparency, and strength were not significantly different. This shows that during the immersion process, not too many water molecules enter the interior of the sample, causing the sample to swell, and the synthesized organosilicon material containing zwitterionic precursors has good swelling resistance.

Embodiment 6:

Preparation of coating film (ie, silicone material): Add 1.00 g of the silicone oil prepared in Example 1 and 2 mL of ethyl acetate into a 5 mL centrifuge tube, shake on a vortex mixer to fully dissolve it. Add 120 μg MDI to the centrifuge tube, and mix well by ultrasonic. The mixed solution was poured into the mold, and dried in a 37°C drying oven for 24 hours to fully form a film. The hardness of the obtained silicone material was improved to a certain extent, and it had good anti-protein non-specific adsorption ability and anti-swelling performance.

Claims (16)

1. A modified silicone oil containing carboxybetaine zwitterionic precursors, characterized in that it has a structure as shown in the following formula I: In Formula I, 0<n≤800. 2. a preparation method of modified silicone oil as claimed in claim 1, is characterized in that, comprises: Step a: mixing the first compound having the structure shown in formula II, the second compound having the structure shown in formula III, the platinum-containing catalyst, the phenolic polymerization inhibitor and the first solvent, and performing hydrosilylation reaction to obtain The third compound with the structure shown in formula IV, in formula III and formula IV, 0<n≤800; Step b: Mixing the third compound, the tin-containing catalyst, sarcosinate and the second solvent, and performing an epoxy group ring-opening reaction to obtain the modified silicone oil; 3. the preparation method of modified silicone oil according to claim 2 is characterized in that: in described step a, the mol ratio of the Si-H bond in the first compound and the second compound is 1:0.6～ 0.7, the mass ratio of the first compound, the platinum-containing catalyst, the phenolic polymerization inhibitor and the first solvent is 1:0.001～0.005:0.001～0.005:2～15, and the reaction temperature of the hydrosilylation reaction is 80～ 110°C, the reaction time is 4 to 8 hours. 4. according to the preparation method of claim 2 or 3 described modified silicone oils, it is characterized in that: in described step b, the mol ratio of described sarcosinate and the epoxy group in the 3rd compound is 1 : 1, the reaction temperature of the ring-opening reaction of the epoxy group is 70-80°C, and the reaction time is 8-12h. 5. The preparation method of modified silicone oil according to claim 2 or 3, characterized in that: the sarcosinate is tert-butyl sarcosinate. 6. the preparation method of modified silicone oil according to claim 4 is characterized in that: described sarcosinate is t-butyl sarcosinate. 7. The method for preparing modified silicone oil according to claim 2, 3 or 6, characterized in that: the first compound is allyl glycidyl ether, and the second compound is hydrogen-containing silicone oil. 8. The preparation method of modified silicone oil according to claim 4, characterized in that: the first compound is allyl glycidyl ether, and the second compound is hydrogen-containing silicone oil. 9. The preparation method of modified silicone oil according to claim 5, characterized in that: the first compound is allyl glycidyl ether, and the second compound is hydrogen-containing silicone oil. 10. according to the preparation method of the described modified silicone oil of claim 2,3,6,8 or 9, it is characterized in that: described tin-containing catalyst is stannous isooctanoate, and platinum-containing catalyst is Karetedt platinum catalyst, phenolic inhibitor The polymerization agent is 2,6-di-tert-butyl-4-methylphenol. 11. The preparation method of modified silicone oil according to claim 4, characterized in that: the tin-containing catalyst is stannous isooctanoate, the platinum-containing catalyst is a Karetedt platinum catalyst, and the phenolic polymerization inhibitor is 2,6-di tert-butyl-4-methylphenol. 12. The preparation method of modified silicone oil according to claim 5, characterized in that: the tin-containing catalyst is stannous isooctanoate, the platinum-containing catalyst is a Karetedt platinum catalyst, and the phenolic polymerization inhibitor is 2,6-di tert-butyl-4-methylphenol. 13. The preparation method of modified silicone oil according to claim 7, characterized in that: the tin-containing catalyst is stannous isooctanoate, the platinum-containing catalyst is a Karetedt platinum catalyst, and the phenolic polymerization inhibitor is 2,6-di tert-butyl-4-methylphenol. 14. A method for preparing an organosilicon material by using the modified silicone oil according to claim 1, characterized in that: the organosilicon material is obtained by cross-linking the modified silicone oil. 15. The method according to claim 14, characterized in that: add a volatile organic solvent without active hydrogen and a cross-linking agent to the modified silicone oil, and solidify after cross-linking reaction to obtain the organosilicon material . 16. The method according to claim 15, characterized in that the crosslinking agent is a molecule containing polyisocyanate groups.