A modified organosilicon compound, and a method of making and using the same

Abstract

The application provides a modified organosilicon compound, a preparation method and application thereof, raw materials of the modified organosilicon compound include a hydroxyl-containing compound and an isocyanate single-terminated silane; the hydroxyl-containing compound includes a saturated fatty alcohol and / or a hydroxyl silicone wax. In the application, the modified organosilicon compound has good hydrophobicity and strong crosslinking capacity, can effectively improve the hydrophobicity, mechanical property and the like of a material, and obtain a material with more excellent comprehensive performance; and the raw materials of the modified organosilicon compound are widely sourced and low in price, thereby effectively reducing the production cost.

Description

Technical Field

[0001] This invention belongs to the field of organosilicon materials technology, specifically relating to a modified organosilicon compound, its preparation method, and its application. Background Technology

[0002] In materials science, coupling agents, as important surfactants, can act as a "bridge" between organic and inorganic substances. They are widely used in powder modification, rubber and plastic additives, and adhesives to improve the compatibility of the system, thereby improving the processing performance and mechanical properties of the material. For adhesives, they can also improve the bonding performance and adhesion. In addition, introducing hydrophobic groups into coupling agents can significantly improve the hydrophobicity of the material surface, thus meeting the application requirements of different scenarios.

[0003] Among them, the long-chain alkylalkoxysilane coupling agent has the structural formula YSiR. n X 3-n In this compound, n is an integer from 0 to 3, Y is a long-chain alkyl group, R is an alkyl group, and X is usually a methoxy, ethoxy, or other group. It is a highly distinctive organosilicon compound. Due to its unique structure, long-chain alkylalkoxysilane coupling agents are endowed with special properties and are excellent raw materials for preparing high-performance materials. Furthermore, long-chain alkyl groups can also give materials a special feel and can be used as a feel treatment agent to improve the feel performance of materials.

[0004] However, existing long-chain alkylalkoxysilane coupling agents have poor hydrophobicity and crosslinking ability, resulting in limited improvement on the hydrophobicity and mechanical properties of materials. Furthermore, the preparation of long-chain alkylalkoxysilane coupling agents in existing technologies mainly involves two methods: ① Under normal pressure, long-chain olefins react with trichlorosilane in the presence of a catalyst to form long-chain alkyltrichlorosilanes, which are then reacted with alcohols to obtain long-chain alkyltrialkoxysilanes. ② Under normal pressure, long-chain alkyl groups directly react with trialkoxysilanes in the presence of a catalyst to obtain long-chain alkyltrialkoxysilanes. However, both of these methods suffer from complex synthesis steps, high raw material costs, and environmental pollution, limiting their widespread application in practice.

[0005] For example, CN109824713A discloses a long-chain alkyltrialkoxysilane and its preparation method. Under nitrogen atmosphere, using chloroplatinic acid and N,N-dimethylaniline as catalysts, a long-chain olefin is reacted with a trialkoxysilane to prepare a long-chain alkylalkoxysilane coupling agent. However, this long-chain silane coupling agent has poor hydrophobicity, resulting in limited improvement on the mechanical properties of the material. Furthermore, the preparation method requires the heavy metal catalyst chloroplatinic acid and the aniline catalyst, and subsequent distillation is necessary to remove excess trialkylsilane monomers, limiting product purity and complicating the processing technology.

[0006] Therefore, developing an organosilicon material with good hydrophobic properties, a high degree of improvement in the mechanical properties of materials, and a simple and environmentally friendly preparation method is an urgent technical problem to be solved in this field. Summary of the Invention

[0007] To address the shortcomings of existing technologies, the present invention aims to provide a modified organosilicon compound, its preparation method, and its applications. The modified organosilicon compound exhibits good hydrophobicity and strong crosslinking ability, effectively improving the hydrophobic and mechanical properties of materials, resulting in materials with superior overall performance. Furthermore, the raw materials for preparing the modified organosilicon compound are widely available and inexpensive, effectively reducing production costs.

[0008] To achieve this objective, the present invention adopts the following technical solution:

[0009] In a first aspect, the present invention provides a modified organosilicon compound, wherein the raw materials for preparing the modified organosilicon compound include a hydroxyl-containing compound and an isocyanate-terminated silane; the hydroxyl-containing compound includes saturated fatty alcohols and / or hydroxyl silicone waxes.

[0010] In this invention, hydroxyl-containing compounds and isocyanate-terminated silanes are used as raw materials to introduce urethane groups into the molecular chain of organosilicon. At the same time, the hydroxyl-containing compounds are of a specific type. The resulting modified organosilicon material has good hydrophobicity and strong crosslinking ability, which can effectively improve the hydrophobic properties, mechanical properties and other properties of the material.

[0011] Preferably, the number of carbon atoms in the main chain of the saturated fatty alcohol is ≥5, for example, it can be 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, etc.; more preferably, the number of carbon atoms in the main chain is 8 to 22.

[0012] Preferably, the saturated fatty alcohol includes saturated monohydric alcohols and / or saturated dihydric alcohols, and is more preferably a saturated monohydric alcohol.

[0013] Preferably, the saturated monohydric alcohol comprises monohydric alcohol A and / or monohydric alcohol B; the number of carbon atoms in the main chain of monohydric alcohol B is greater than the number of carbon atoms in the main chain of monohydric alcohol A.

[0014] Preferably, monohydric alcohol A and monohydric alcohol B each independently comprise at least one of pentanol, hexanol, heptanol, octanol, nonanol, decanol, decacarbonol, lauryl alcohol, tetradecyl alcohol, hexadecyl alcohol, octadecanol, docosyl alcohol, or derivatives and / or isomers of the aforementioned monohydric alcohols.

[0015] Preferably, the saturated monohydric alcohol comprises monohydric alcohol A and monohydric alcohol B, wherein the molar ratio of monohydric alcohol A to monohydric alcohol B is 1:(0.5-3), wherein the specific values ​​of (0.5-3) can be, for example, 0.5, 0.55, 0.6, 0.65, 0.7, 0.75, 0.8, 0.85, 0.9, 0.95, 1, 1.2, 1.4, 1.6, 1.8, 2, 2.2, 2.4, 2.6, 2.8, 3, etc.

[0016] Preferably, the saturated diol includes at least one of pentanediol, hexanediol, heptanediol, octanediol, nonanediol, decanediol, undecanediol, dodecanediol, tetradecanediol, hexadecanediol, octadecanediol, or derivatives and / or isomers of the aforementioned diols.

[0017] Preferably, the number-average molecular weight of the hydroxyl silicone wax is 5000-7000 g / mol, for example, it can be 5000 g / mol, 5200 g / mol, 5500 g / mol, 5800 g / mol, 6000 g / mol, 6200 g / mol, 6400 g / mol, 6600 g / mol, 6800 g / mol, 7000 g / mol, etc.; the hydroxyl value is 5-15 mg KOH / g, for example, it can be 5 mg KOH / g, 6 mg KOH / g, 7 mg KOH / g, 8 mg KOH / g, 9 mg KOH / g, 10 mg KOH / g, 11 mg KOH / g, 12 mg KOH / g, 13 mg KOH / g, 14 mg KOH / g, 15 mg KOH / g, etc.

[0018] Preferably, the hydroxyl-containing compound includes saturated fatty alcohol and hydroxyl silicone wax, and the molar ratio of the saturated fatty alcohol to the hydroxyl silicone wax is 1:(0.05-0.5), wherein the specific values ​​of (0.05-0.5) can be, for example, 0.05, 0.06, 0.08, 0.1, 0.12, 0.14, 0.16, 0.18, 0.2, 0.22, 0.24, 0.26, 0.28, 0.3, 0.32, 0.34, 0.36, 0.38, 0.4, 0.42, 0.44, 0.46, 0.48, 0.5, etc.; more preferably, it is 1:(0.1-0.3).

[0019] Preferably, the isocyanate-terminated silane has the structure shown in Formula I.

[0020]

[0021] R1, R2, and R3 are each independently selected from straight-chain or branched alkyl groups or straight-chain or branched alkoxy groups of C1 to C6, and at least one of R1, R2, and R3 is selected from straight-chain or branched alkoxy groups of C1 to C6; n is an integer from 0 to 6.

[0022] In this invention, the C1-C6 straight-chain or branched alkyl groups include straight-chain or branched alkyl groups of C1, C2, C3, C4, C5, and C6, and exemplary, include but are not limited to methyl, ethyl, n-propyl, isopropyl, n-butyl, n-pentyl, n-hexyl, etc.; the C1-C6 straight-chain or branched alkoxy groups include straight-chain or branched alkoxy groups of C1, C2, C3, C4, C5, and C6, and exemplary, include but are not limited to methoxy, ethoxy, etc.

[0023] In this invention, n is an integer from 0 to 6, for example, it can be 0, 1, 2, 3, 4, 5, 6, etc.

[0024] Preferably, the isocyanate-terminated silane comprises at least one of isocyanate-trimethoxysilane, isocyanate-triethoxysilane, 3-isocyanate-propyltrimethoxysilane, 3-isocyanate-propyltriethoxysilane, 3-isocyanate-methyltrimethoxysilane, 3-isocyanate-ethyltrimethoxysilane, isocyanate-propylmethyldimethoxysilane, or isocyanate-propylmethyldiethoxysilane, and more preferably isocyanate-trimethoxysilane and / or isocyanate-triethoxysilane.

[0025] Preferably, in the raw materials for preparation, the molar ratio of isocyanate group to hydroxyl group is (1-1.5):1, wherein the specific values ​​of (1-1.5) can be, for example, 1, 1.1, 1.2, 1.3, 1.4, 1.5, etc.

[0026] In a second aspect, the present invention provides a method for preparing the modified organosilicon compound according to the first aspect, the method comprising the following steps:

[0027] The modified organosilicon compound is obtained by reacting a hydroxyl-containing compound with an isocyanate-terminated silane.

[0028] Preferably, the reaction temperature is 100-130°C, for example, 100°C, 105°C, 110°C, 115°C, 120°C, 125°C, 130°C, etc.

[0029] Preferably, the reaction time is 3 to 5 hours, for example, 3 hours, 3.3 hours, 3.4 hours, 3.5 hours, 3.6 hours, 3.8 hours, 4 hours, 4.2 hours, 4.4 hours, 4.5 hours, 4.6 hours, 4.8 hours, 5 hours, etc.

[0030] Preferably, the reaction further includes a step of dehydrating the hydroxyl-containing compound.

[0031] Preferably, the dehydration temperature is 110–120°C, for example, 110°C, 112°C, 115°C, 118°C, 120°C, etc.; the pressure is ≤0.1MPa, for example, 0.01MPa, 0.02MPa, 0.04MPa, 0.06MPa, 0.08MPa, 0.1MPa, etc.; and the time is 0.5–2h, for example, 0.5h, 0.6h, 0.8h, 1h, 1.2h, 1.4h, 1.5h, 1.6h, 1.8h, 2h, etc.

[0032] In this invention, the mass of isocyanate groups in the reaction system is 0-0.1%.

[0033] In this invention, the mass of isocyanate groups in the system is tested by titration or by using an infrared spectrometer.

[0034] In this invention, hydrophobic organosilicon can be prepared in one step. The preparation method does not require the addition of a catalyst, the reaction process is mild and controllable, the post-processing is simple, no distillation purification is required, and no waste is generated, thus reducing the generation and emission of harmful substances and conforming to the development trend of green and environmentally friendly practices.

[0035] Thirdly, the present invention provides a hydrophobic coupling agent comprising the modified organosilicon compound according to the first aspect.

[0036] The numerical range described in this invention includes not only the point values ​​listed above, but also any point values ​​within the numerical ranges not listed above. Due to space limitations and for the sake of brevity, this invention will not exhaustively list all the specific point values ​​included in the range.

[0037] Compared with the prior art, the beneficial effects of the present invention are as follows:

[0038] The modified organosilicon compound provided by this invention uses hydroxyl-containing compounds and isocyanate-terminated silanes as raw materials to introduce urethane groups into the molecular chain of organosilicon. At the same time, the hydroxyl-containing compounds are of a specific type. The resulting modified organosilicon material has good hydrophobicity and strong crosslinking ability, which can effectively improve the hydrophobic properties, mechanical properties and other properties of the material. Detailed Implementation

[0039] The technical solution of the present invention will be further illustrated below through specific embodiments. Those skilled in the art should understand that the embodiments described are merely illustrative of the present invention and should not be construed as limiting the invention in any way.

[0040] Example 1

[0041] This embodiment provides a modified organosilicon compound. The raw materials for preparing the modified organosilicon compound include a hydroxyl-containing compound and an isocyanate-based trimethoxysilane. The molar ratio of isocyanate groups to hydroxyl groups in the raw materials is 1.1:1. The hydroxyl-containing compound includes n-dodecyl alcohol and n-octadecyl alcohol in a molar ratio of 1:0.69.

[0042] This embodiment provides a method for preparing a modified organosilicon compound, specifically including the following steps:

[0043] The hydroxyl-containing compound was placed in a reactor, heated to 115°C and stirred until melted. Then, a vacuum pump was used to evacuate the system to 0.08 MPa and maintained for 1 hour for dehydration. The dehydrated hydroxyl-containing compound was then reacted with isocyanate-based trimethoxysilane at 130°C under stirring conditions for 3 hours until the mass percentage of isocyanate groups in the system was less than 0.1%, thus obtaining the modified organosilicon compound.

[0044] Example 2

[0045] This embodiment provides a modified organosilicon compound. The raw materials for preparing the modified organosilicon compound include a hydroxyl-containing compound and isocyanate-based triethoxysilane. The molar ratio of isocyanate groups to hydroxyl groups in the raw materials is 1.06:1. The hydroxyl-containing compound includes n-heptanol and n-nonanol in a molar ratio of 1:0.8.

[0046] This embodiment provides a method for preparing a modified organosilicon compound, specifically including the following steps:

[0047] The hydroxyl-containing compound was placed in a reactor, heated to 112°C, and evacuated to 0.095 MPa using a vacuum pump for 1 hour to dehydrate. Then, the dehydrated hydroxyl-containing compound was reacted with isocyanate-based triethoxysilane under stirring conditions at 118°C for 4 hours until the mass percentage of isocyanate groups in the system was less than 0.04%, thus obtaining the modified organosilicon compound.

[0048] Example 3

[0049] This embodiment provides a modified organosilicon compound. The raw materials for preparing the modified organosilicon compound include a hydroxyl-containing compound and isocyanate-based triethoxysilane. The molar ratio of isocyanate groups to hydroxyl groups in the raw materials is 1.07:1. The hydroxyl-containing compound includes n-hexanol and n-octanol in a molar ratio of 1:0.78.

[0050] This embodiment provides a method for preparing a modified organosilicon compound, specifically including the following steps:

[0051] The hydroxyl-containing compound was placed in a reactor, heated to 111°C, and evacuated to 0.085 MPa using a vacuum pump, and held for 45 min to dehydrate. Then, the dehydrated hydroxyl-containing compound was reacted with isocyanate-based triethoxysilane under stirring conditions at 124°C for 3.7 h until the mass percentage of isocyanate groups in the system was less than 0.1%, thus obtaining the modified organosilicon compound.

[0052] Example 4

[0053] This embodiment provides a modified organosilicon compound. The raw materials for preparing the modified organosilicon compound include a hydroxyl-containing compound and isocyanate-based triethoxysilane. The molar ratio of isocyanate groups to hydroxyl groups in the raw materials is 1.09:1. The hydroxyl-containing compound includes n-decyl alcohol and n-hexadecyl alcohol in a molar ratio of 1:0.65.

[0054] This embodiment provides a method for preparing a modified organosilicon compound, specifically including the following steps:

[0055] The hydroxyl-containing compound was placed in a reactor, heated to 113°C, and evacuated to 0.08 MPa using a vacuum pump for 50 min to dehydrate. Then, the dehydrated hydroxyl-containing compound was reacted with isocyanate-based triethoxysilane under stirring conditions at 126°C for 3.5 h until the mass percentage of isocyanate groups in the system was less than 0.1%, thus obtaining the modified organosilicon compound.

[0056] Example 5

[0057] This embodiment provides a modified organosilicon compound. The raw materials for preparing the modified organosilicon compound include a hydroxyl-containing compound and isocyanate-based triethoxysilane. The molar ratio of isocyanate groups to hydroxyl groups in the raw materials is 1.05:1. The hydroxyl-containing compound includes n-tetradecyl alcohol and n-hexadecyl alcohol in a molar ratio of 1:2.83.

[0058] This embodiment provides a method for preparing a modified organosilicon compound, specifically including the following steps:

[0059] The hydroxyl-containing compound was placed in a reactor, heated to 120°C, and evacuated to 0.07 MPa using a vacuum pump, and held for 45 min to dehydrate. Then, the dehydrated hydroxyl-containing compound was reacted with isocyanate-based triethoxysilane under stirring conditions at 125°C for 3.5 h until the mass percentage of isocyanate groups in the system was less than 0.02%, thus obtaining the modified organosilicon compound.

[0060] Example 6

[0061] This embodiment provides a modified organosilicon compound, which differs from Example 1 only in that the total molar amount of n-dodecyl alcohol and n-octadecyl alcohol remains unchanged, the molar ratio is 1:0.4, and the other components, amounts and preparation methods are the same as in Example 1.

[0062] Example 7

[0063] This embodiment provides a modified organosilicon compound, which differs from Example 1 only in that the total molar amount of n-dodecyl alcohol and n-octadecyl alcohol remains unchanged, the molar ratio is 1:3.4, and the other components, amounts and preparation methods are the same as in Example 1.

[0064] Example 8

[0065] This embodiment provides a modified organosilicon compound, which differs from Example 1 only in that the total molar amount of the hydroxyl-containing compound remains unchanged, consisting of n-pentanol and n-hexanol in a molar ratio of 1:0.69. The other components, amounts, and preparation methods are the same as in Example 1.

[0066] Example 9

[0067] This embodiment provides a modified organosilicon compound, which differs from Example 1 only in that the total molar amount of the hydroxyl-containing compound remains unchanged, consisting of n-docodiol and n-tetracodol in a molar ratio of 1:0.69. The other components, amounts, and preparation methods are the same as in Example 1.

[0068] Example 10

[0069] This embodiment provides a modified organosilicon compound, which differs from Example 1 only in that the total molar amount of the hydroxyl-containing compound remains unchanged, and it is n-octadecyl alcohol. The other raw materials, amounts, and preparation methods are the same as in Example 1.

[0070] Example 11

[0071] This embodiment provides a modified organosilicon compound, which differs from Example 1 only in that the total molar amount of the hydroxyl-containing compound remains unchanged, and it is n-dodecyl alcohol. Other raw materials, amounts, and preparation methods are the same as in Example 1.

[0072] Example 12

[0073] This embodiment provides a modified organosilicon compound, which differs from Example 1 only in that the total molar amount of the hydroxyl-containing compound remains unchanged, and it is n-decyl alcohol. Other raw materials, amounts, and preparation methods are the same as in Example 1.

[0074] Example 13

[0075] This embodiment provides a modified organosilicon compound, which differs from Example 1 only in that the total molar amount of the hydroxyl-containing compound remains unchanged, and it is n-tetradecyl alcohol. The other raw materials, amounts, and preparation methods are the same as in Example 1.

[0076] Example 14

[0077] This embodiment provides a modified organosilicon compound, which differs from Example 1 only in that the total molar amount of the hydroxyl-containing compound remains unchanged, and it is n-pentanol. The other raw materials, amounts, and preparation methods are the same as in Example 1.

[0078] Example 15

[0079] This embodiment provides a modified organosilicon compound, which differs from Example 1 only in that the total molar amount of the hydroxyl-containing compound remains unchanged, and it is n-tetracosyl alcohol. The other raw materials, amounts, and preparation methods are the same as in Example 1.

[0080] Example 16

[0081] This embodiment provides a modified organosilicon compound, which differs from Example 1 only in that the total molar amount of the hydroxyl-containing compound remains unchanged, and it is decanediol. The other raw materials, amounts, and preparation methods are the same as in Example 1.

[0082] Example 17

[0083] This embodiment provides a modified organosilicon compound, which differs from Example 1 only in that isocyanate-trimethoxysilane is replaced with 3-isocyanate-propyltrimethoxysilane in an equal molar amount of isocyanate. Other raw materials, amounts, and preparation methods are the same as in Example 1.

[0084] Example 18

[0085] This embodiment provides a modified organosilicon compound, which differs from Example 1 only in that the total molar amount of the hydroxyl-containing compound remains unchanged. The hydroxyl-containing compound includes a saturated polyol and a hydroxyl silicone wax (Silok 6039P1 from Guangzhou Silok Polymer Co., Ltd., with a number average molecular weight of 6000 g / mol and a hydroxyl value of 10 mg KOH / g) in a molar ratio of 1:0.69. The other raw materials, amounts, and preparation methods are the same as in Example 1.

[0086] Example 19

[0087] This embodiment provides a modified organosilicon compound, which differs from Example 1 only in that the total molar amount of the hydroxyl-containing compound remains unchanged. The hydroxyl-containing compound includes a saturated polyol and a hydroxyl silicone wax (Silok 6039P1 from Guangzhou Silok Polymer Co., Ltd., with a number average molecular weight of 6000 g / mol and a hydroxyl value of 10 mg KOH / g) in a molar ratio of 1:0.05. The saturated polyol includes n-dodecyl alcohol and n-octadecyl alcohol in a molar ratio of 1:0.69. Other raw materials, amounts, and preparation methods are the same as in Example 1.

[0088] Example 20

[0089] This embodiment provides a modified organosilicon compound, which differs from Example 1 only in that the total molar amount of the hydroxyl-containing compound remains unchanged. The hydroxyl-containing compound includes a saturated polyol and a hydroxyl silicone wax (Silok 6039P1 from Guangzhou Silok Polymer Co., Ltd., with a number average molecular weight of 6000 g / mol and a hydroxyl value of 10 mg KOH / g) in a molar ratio of 1:0.69. The other raw materials, amounts, and preparation methods are the same as in Example 1.

[0090] Comparative Example 1

[0091] This comparative example provides a modified organosilicon compound, which differs from Example 1 only in that the total molar amount of the hydroxyl-containing compound remains unchanged, and is allyl alcohol. Other raw materials, amounts, and preparation methods are the same as in Example 1.

[0092] Comparative Example 2

[0093] This comparative example provides a modified organosilicon compound, which differs from Example 1 only in that isocyanate-based trimethoxysilane is replaced with an equal molar amount of isocyanate. (CAS No. 37601-26-6, purchased from Hong Kong Chemhere), other raw materials, dosages and preparation methods are the same as in Example 1.

[0094] Comparative Example 3

[0095] This comparative example provides an organosilicon compound, namely dodecyltrimethoxysilane.

[0096] Application examples

[0097] This application example provides a modified plastic comprising, by weight, 100 parts polypropylene (PP, Shell HP500N-Z), 5 parts coupling agent, 0.5 parts antioxidant (IRGANOX 1010), and 0.3 parts ultraviolet absorber (TINUVIN328); the coupling agent being the modified organosilicon compound provided in Examples 1-20, Comparative Examples 1 and 2, and the hydrophobic organosilicon provided in Comparative Example 3.

[0098] The method for preparing the modified plastic includes: mixing polypropylene with a coupling agent evenly, then adding an antioxidant and an ultraviolet absorber, melting and mixing at 200°C, and injection molding to obtain the modified plastic.

[0099] Performance testing

[0100] The modified plastic was then subjected to the following tests:

[0101] (1) Hydrophobicity test: Place the sample to be tested on a water platform, and use a microsyringe to drop a certain amount of deionized water (about 5 μL) onto the sample surface. Test the contact angle using a contact angle meter; the larger the contact angle, the better the hydrophobicity of the material.

[0102] (2) Mechanical properties: The tensile strength and elongation at break of the material are tested; high tensile strength and moderate elongation at break indicate good cross-linking properties and excellent mechanical properties; the specific test methods are as follows:

[0103] Using a universal testing machine, the sample (10 mm wide and 5 mm thick) was clamped in upper and lower fixtures (115 mm apart) and stretched at a constant speed (25 m / min) until it broke. The maximum tensile force at fracture was recorded, and the tensile strength was calculated based on the sample size. Tensile strength = maximum tensile force / (sample width × sample thickness). The elongation of the sample from its original length to the point of fracture was also recorded, and the elongation at break was calculated.

[0104] The specific test results are shown in Table 1.

[0105] Table 1

[0106]

[0107]

[0108] As shown in Table 1, the modified organosilicon compound provided by this invention uses hydroxyl-containing compounds and isocyanate-terminated silanes as raw materials to introduce urethane groups into the molecular chain of organosilicon. Simultaneously, the hydroxyl-containing compounds are of a specific type. The resulting modified organosilicon material exhibits good hydrophobicity and strong crosslinking ability, effectively improving the hydrophobic properties and mechanical properties of the material. Plastics containing the modified organosilicon compound have a contact angle ≥104°, tensile strength ≥28 MPa, and elongation at break ≥195%.

[0109] As can be seen from the comparison of the examples with Comparative Examples 1 and 2, the modified organosilicon compounds obtained from non-specific raw materials have poor hydrophobic and mechanical properties of plastics. As can be seen from Comparative Example 3, compared with conventional long carbon chain organosilicon, the modified organosilicon compounds obtained by introducing urethane structures and using specific raw materials in this invention can effectively improve the hydrophobic and mechanical properties of plastics.

[0110] The specific embodiments described above further illustrate the purpose, technical solution, and beneficial effects of the present invention. It should be understood that the above descriptions are merely specific embodiments of the present invention and are not intended to limit the present invention. Any modifications, equivalent substitutions, improvements, etc., made within the spirit and principles of the present invention should be included within the protection scope of the present invention.

Claims

1. A modified organosilicon compound, characterized in that, The raw materials for preparing the modified organosilicon compound include hydroxyl-containing compounds and isocyanate-terminated silanes; The hydroxyl-containing compound includes saturated fatty alcohols or a combination of saturated fatty alcohols and hydroxyl silicone waxes; The saturated fatty alcohol is composed of monohydric alcohol A and monohydric alcohol B; the number of carbon atoms in the main chain of monohydric alcohol B is greater than the number of carbon atoms in the main chain of monohydric alcohol A; the molar ratio of monohydric alcohol A to monohydric alcohol B is 1:(0.5~3); the number of carbon atoms in the main chain of the saturated fatty alcohol is ≥5. The number-average molecular weight of the hydroxyl silicone wax is 5000~7000 g / mol, and the hydroxyl value is 5~15 mg KOH / g; The isocyanate-terminated silane has the structure shown in Formula I. Equation I; R1, R2, and R3 are each independently selected from C1 to C6 straight-chain or branched alkyl groups or C1 to C6 straight-chain or branched alkoxy groups, and at least one of R1, R2, and R3 is selected from C1 to C6 straight-chain or branched alkoxy groups; n is an integer from 0 to 6.

2. The modified organosilicon compound according to claim 1, characterized in that, The saturated fatty alcohol backbone has 8 to 22 carbon atoms.

3. The modified organosilicon compound according to claim 1, characterized in that, The monohydric alcohol A and monohydric alcohol B are each independently selected from pentanol, hexanol, heptanol, octanol, nonanol, decanol, decacarbonol, lauryl alcohol, tetradecyl alcohol, hexadecyl alcohol, octadecyl alcohol, or docosyl alcohol.

4. The modified organosilicon compound according to claim 1, characterized in that, The molar ratio of the saturated fatty alcohol to the hydroxyl silicone wax is 1:(0.05~0.5).

5. The modified organosilicon compound according to claim 1, characterized in that, The molar ratio of the saturated fatty alcohol to the hydroxyl silicone wax is 1:(0.1~0.3).

6. The modified organosilicon compound according to claim 1, characterized in that, The isocyanate-terminated silane is selected from at least one of isocyanate-trimethoxysilane, isocyanate-triethoxysilane, 3-isocyanate-propyltrimethoxysilane, 3-isocyanate-propyltriethoxysilane, 3-isocyanate-methyltrimethoxysilane, 3-isocyanate-ethyltrimethoxysilane, isocyanate-propylmethyldimethoxysilane, or isocyanate-propylmethyldiethoxysilane.

7. The modified organosilicon compound according to claim 6, characterized in that, The isocyanate-terminated silane is isocyanate-based trimethoxysilane and / or isocyanate-based triethoxysilane.

8. The modified organosilicon compound according to claim 1, characterized in that, In the raw materials used for preparation, the molar ratio of isocyanate groups to hydroxyl groups is (1~1.5):

1.

9. A method for preparing a modified organosilicon compound according to any one of claims 1 to 8, characterized in that, The preparation method includes the following steps: The modified organosilicon compound is obtained by reacting a hydroxyl-containing compound with an isocyanate-terminated silane.

10. The preparation method according to claim 9, characterized in that, The reaction temperature is 100~130℃.

11. The preparation method according to claim 9, characterized in that, The reaction time is 3-5 hours.

12. The preparation method according to claim 9, characterized in that, The reaction also includes a step of dehydrating the hydroxyl-containing compound.

13. The preparation method according to claim 12, characterized in that, The dehydration temperature is 110~120℃, the pressure is ≤0.1MPa, and the time is 0.5~2 h.

14. A hydrophobic coupling agent, characterized in that, The hydrophobic coupling agent includes the modified organosilicon compound according to any one of claims 1 to 8.

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