Modified organosilicon compound and preparation method and application thereof

Abstract

The invention provides a modified organosilicon compound as well as a preparation method and application thereof. The modified organosilicon compound is prepared from the following raw materials: a hydroxyl-containing compound and isocyanate single-terminated silane, the hydroxyl-containing compound comprises saturated fatty alcohol and / or hydroxyl silicone wax. According to the invention, the modified organosilicon compound has good hydrophobicity and strong cross-linking ability, can effectively improve the hydrophobicity, mechanical properties and the like of the material, and obtains the material with better comprehensive properties; the preparation raw materials of the modified organosilicon compound are wide in source and low in price, and the production cost is effectively reduced.

Description

Technical Field

[0001] The invention belongs to the technical field of organosilicon materials, and specifically relates to a modified organosilicon compound and a preparation method and application thereof. Background Art

[0002] In materials science, coupling agents, as an important surfactant, can serve as a "bridge" between organic and inorganic substances and are widely used in powder modification, rubber and plastic additives, adhesives and other fields. They can 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 properties of the adhesive and enhance its adhesion. In addition, the introduction of hydrophobic groups in the coupling agent can significantly improve the hydrophobicity of the material surface, thereby meeting the usage requirements of different scenarios.

[0003] Among them, the long-chain alkyl alkoxy silane coupling agent has the structural formula YSiR n X 3-n , where n is an integer of 0-3, Y is a long-chain alkyl group, R is an alkyl group, and X is usually a methoxy group, an ethoxy group or other groups. It is a very distinctive organosilicon compound. Due to its unique structure, it gives the long-chain alkyl alkoxysilane coupling agent special properties and is an excellent raw material for preparing high-performance materials. In addition, the long-chain alkyl group can also give the material a special feel, and can be used as a feel treatment agent to improve the feel performance of the material.

[0004] However, the existing long-chain alkyl alkoxysilane coupling agents have poor hydrophobicity and poor cross-linking ability, and have little improvement on the hydrophobicity and mechanical properties of the materials; and the preparation of long-chain alkyl alkoxysilane coupling agents in the prior art mainly includes two methods: ① Addition of long-chain olefins and trichlorosilane under normal pressure in the presence of a catalyst to form long-chain alkyl trichlorosilane, and then reacting the generated long-chain alkyl trichlorosilane with an alcohol to obtain a long-chain alkyl trialkoxysilane. ② Direct addition of a long-chain alkyl group with a trialkoxyhydrosilane under normal pressure in the presence of a catalyst to obtain a long-chain alkyl trialkoxysilane. However, the aforementioned methods all have problems such as complex synthesis steps, high raw material costs, and environmental pollution, which limit their promotion in practical applications.

[0005] For example, CN109824713A discloses a long-chain alkyltrialkoxysilane and a preparation method thereof, wherein a long-chain olefin is reacted with a trialkoxyhydrosilane using chloroplatinic acid and N,N-dimethylaniline as catalysts in a nitrogen environment to prepare a long-chain alkylalkoxysilane coupling agent. However, the long carbon chain silane coupling agent has poor hydrophobicity, and has a low degree of improvement on the mechanical properties of the material. In addition, the preparation method requires a heavy metal catalyst chloroplatinic acid and an aniline catalyst, and the excess trialkylhydrosilane monomer needs to be distilled off in the later stage, so the product purity is limited and the processing process is also relatively complicated.

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

[0007] In view of the shortcomings of the prior art, the present invention aims to provide a modified organosilicon compound and a preparation method and application thereof. The modified organosilicon compound has good hydrophobicity and strong cross-linking ability, and can effectively improve the hydrophobicity and mechanical properties of the material to obtain a material with better comprehensive performance; and the raw materials for the preparation of the modified organosilicon compound are widely available and inexpensive, which effectively reduces the production cost.

[0008] To achieve this object, the present invention adopts the following technical solutions:

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

[0010] In the present invention, hydroxyl-containing compounds and isocyanate mono-terminated silane are used as raw materials to introduce carbamate groups into the molecular chain of silicone. At the same time, the hydroxyl-containing compounds are of specific types, and the obtained modified silicone material has good hydrophobicity and strong cross-linking ability, which can effectively improve the hydrophobicity, mechanical properties, etc. 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 8-22.

[0012] Preferably, the saturated fatty alcohol comprises a saturated monohydric alcohol and / or a saturated dihydric alcohol, preferably a saturated monohydric alcohol.

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

[0014] Preferably, the monohydric alcohol A and the monohydric alcohol B each independently include at least one of pentanol, hexanol, heptanol, octanol, nonanol, decanol, decanol, lauryl alcohol, tetradecanol, hexadecanol, octadecanol, docosanol or derivatives and / or isomers of the aforementioned monohydric alcohols.

[0015] Preferably, the saturated monohydric alcohol includes monohydric alcohol A and monohydric alcohol B, and the molar ratio of monohydric alcohol A to monohydric alcohol B is 1:(0.5-3), wherein the specific value 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 comprises at least one of pentanediol, hexanediol, heptanediol, octanediol, nonanediol, decanediol, undecanediol, dodecanediol, tetradecanediol, hexadecanediol, octadecanediol or derivatives and / or isomers of the foregoing diols.

[0017] Preferably, the number average molecular weight of the hydroxy 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 a saturated fatty alcohol and a hydroxy silicone wax, and the molar ratio of the saturated fatty alcohol to the hydroxy silicone wax is 1:(0.05-0.5), wherein the specific value in (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.; further preferably, it is 1:(0.1-0.3).

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

[0020]

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

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

[0023] In the present invention, n is an integer of 0 to 6, for example, 0, 1, 2, 3, 4, 5, 6, etc.

[0024] Preferably, the isocyanate monoterminated silane includes at least one of isocyanate trimethoxysilane, isocyanate triethoxysilane, 3-isocyanate propyl trimethoxysilane, 3-isocyanate propyl triethoxysilane, 3-isocyanate methyl trimethoxysilane, 3-isocyanate ethyl trimethoxysilane, isocyanate propyl methyl dimethoxysilane or isocyanate propyl methyl diethoxysilane, and is more preferably isocyanate trimethoxysilane and / or isocyanate triethoxysilane.

[0025] Preferably, in the preparation raw material, the molar ratio of isocyanate group to hydroxyl group is (1-1.5):1, wherein the specific value 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 preparation method comprising the following steps:

[0027] The hydroxyl-containing compound is reacted with isocyanate mono-terminated silane to obtain the modified organic silicon compound.

[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 h, for example, 3 h, 3.3 h, 3.4 h, 3.5 h, 3.6 h, 3.8 h, 4 h, 4.2 h, 4.4 h, 4.5 h, 4.6 h, 4.8 h, 5 h, etc.

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

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

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

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

[0034] In the present invention, a one-step method is adopted to prepare the hydrophobic organosilicon. The preparation method does not require the addition of a catalyst, the reaction process is mild and controllable, the post-treatment is simple, no distillation and purification are required, no three wastes are generated, the generation and emission of harmful substances are reduced, and it is in line with the development trend of green environmental protection.

[0035] In a third aspect, the present invention provides a hydrophobic coupling agent, wherein the hydrophobic coupling agent comprises the modified organosilicon compound according to the first aspect.

[0036] The numerical range described in the present invention not only includes the point values ​​listed above, but also includes any point values ​​between the above numerical ranges that are not listed. Due to space limitations and for the sake of simplicity, the present invention no longer exhaustively lists the specific point values ​​included in the range.

[0037] Compared with the prior art, the present invention has the following beneficial effects:

[0038] The modified organosilicon compound provided by the present invention uses a hydroxyl-containing compound and an isocyanate mono-terminated silane as raw materials, introduces a carbamate group into the molecular chain of the organosilicon, and at the same time, the hydroxyl-containing compound adopts a specific type, and the obtained modified organosilicon material has good hydrophobicity and strong cross-linking ability, which can effectively improve the hydrophobicity, mechanical properties, etc. of the material. DETAILED DESCRIPTION

[0039] The technical solution of the present invention is further described below by specific implementation methods. It should be understood by those skilled in the art that the embodiments are only to help understand the present invention and should not be regarded as specific limitations of the present invention.

[0040] Example 1

[0041] The present embodiment provides a modified organic silicon compound, wherein the raw materials for preparing the modified organic silicon compound include a hydroxyl-containing compound and isocyanate trimethoxysilane; the molar ratio of isocyanate group to hydroxyl group in the preparation raw material is 1.1:1; the hydroxyl-containing compound includes n-dodecanol and n-octadecyl alcohol in a molar ratio of 1:0.69.

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

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

[0044] Example 2

[0045] The present embodiment provides a modified organic silicon compound, wherein the raw materials for preparing the modified organic silicon compound include a hydroxyl-containing compound and isocyanate triethoxysilane; the molar ratio of isocyanate group to hydroxyl group in the preparation raw material 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, which specifically comprises the following steps:

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

[0048] Example 3

[0049] The present embodiment provides a modified organic silicon compound, wherein the raw materials for preparing the modified organic silicon compound include a hydroxyl-containing compound and isocyanate triethoxysilane; the molar ratio of isocyanate group to hydroxyl group in the preparation raw material 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, which specifically comprises the following steps:

[0051] The hydroxyl-containing compound is placed in a reactor, heated to 111°C, and evacuated to 0.085MPa using a vacuum pump, and maintained for 45 minutes for dehydration; the dehydrated hydroxyl-containing compound is then reacted with isocyanate triethoxysilane under stirring conditions at 124°C for 3.7 hours until the mass percentage of isocyanate groups in the system is less than 0.1%, thereby obtaining the modified organosilicon compound.

[0052] Example 4

[0053] The present embodiment provides a modified organic silicon compound, wherein the raw materials for preparing the modified organic silicon compound include a hydroxyl-containing compound and isocyanate triethoxysilane; the molar ratio of isocyanate group to hydroxyl group in the preparation raw materials is 1.09:1; the hydroxyl-containing compound includes n-decanol and n-hexadecanol in a molar ratio of 1:0.65.

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

[0055] The hydroxyl-containing compound is placed in a reactor, heated to 113°C, and evacuated to 0.08MPa using a vacuum pump and maintained for 50 minutes for dehydration; the dehydrated hydroxyl-containing compound is then reacted with isocyanate triethoxysilane under stirring conditions at 126°C for 3.5 hours until the mass percentage of isocyanate groups in the system is less than 0.1%, thereby obtaining the modified organosilicon compound.

[0056] Example 5

[0057] The present embodiment provides a modified organic silicon compound, wherein the raw materials for preparing the modified organic silicon compound include a hydroxyl-containing compound and isocyanate triethoxysilane; the molar ratio of isocyanate group to hydroxyl group in the preparation raw materials is 1.05:1; the hydroxyl-containing compound includes n-tetradecanol and n-hexadecanol in a molar ratio of 1:2.83.

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

[0059] The hydroxyl-containing compound is placed in a reactor, heated to 120°C, and evacuated to 0.07MPa using a vacuum pump, and maintained for 45 minutes for dehydration; the dehydrated hydroxyl-containing compound is then reacted with isocyanate triethoxysilane under stirring conditions at 125°C for 3.5 hours until the mass percentage of isocyanate groups in the system is less than 0.02%, thereby obtaining the modified organic silicon compound.

[0060] Example 6

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

[0062] Example 7

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

[0064] Example 8

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

[0066] Example 9

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

[0068] Example 10

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

[0070] Embodiment 11

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

[0072] Example 12

[0073] This embodiment provides a modified organosilicon compound, which differs from Embodiment 1 only in that the total molar amount of the hydroxyl-containing compound remains unchanged, namely, n-decanol, and other raw materials, amounts used, and preparation methods are the same as those in Embodiment 1.

[0074] Embodiment 13

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

[0076] Embodiment 14

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

[0078] Embodiment 15

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

[0080] Example 16

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

[0082] Embodiment 17

[0083] This embodiment provides a modified organic silicon compound, which differs from Embodiment 1 only in that isocyanate trimethoxysilane is replaced by 3-isocyanate propyl trimethoxysilane in an equal molar amount of isocyanate, and other raw materials, amounts and preparation methods are the same as those in Embodiment 1.

[0084] Embodiment 18

[0085] This embodiment provides a modified organic silicon compound, which is different from Example 1 only in that the total molar amount of the hydroxyl-containing compound remains unchanged, the hydroxyl-containing compound comprises a saturated polyol and a hydroxyl silicone wax (Silok 6039P1 of 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 1:0.2, the saturated polyol comprises n-dodecanol and n-octadecyl alcohol in a molar ratio of 1:0.69, and other raw materials, amounts and preparation methods are the same as those in Example 1.

[0086] Embodiment 19

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

[0088] Embodiment 20

[0089] This embodiment provides a modified organic silicon compound, which is different from Example 1 only in that the total molar amount of the hydroxyl-containing compound remains unchanged, the hydroxyl-containing compound comprises a saturated polyol and a hydroxyl silicone wax (Silok 6039P1 of 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 1:0.5, the saturated polyol comprises n-dodecanol and n-octadecyl alcohol in a molar ratio of 1:0.69, and other raw materials, amounts and preparation methods are the same as those 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 propylene alcohol, and other raw materials, amounts used and preparation methods are the same as those in Example 1.

[0092] Comparative Example 2

[0093] This comparative example provides a modified organic silicon compound, which differs from Example 1 only in that the isocyanate trimethoxysilane is replaced by an isocyanate having an equal molar amount of (CAS No. 37601-26-6, purchased from Hong Kong Chem here), other raw materials, amounts and preparation methods are the same as those in Example 1.

[0094] Comparative Example 3

[0095] This comparative example provides an organic silicon compound, which is dodecyltrimethoxysilane.

[0096] Application Examples

[0097] This application example provides a modified plastic, which includes, by weight, 100 parts of polypropylene (PP, Shell HP500N-Z), 5 parts of coupling agents, 0.5 parts of antioxidants (IRGANOX 1010) and 0.3 parts of ultraviolet absorbers (TINUVIN328); the coupling agents are the modified silicone compounds provided in Examples 1 to 20, Comparative Examples 1 and 2, and the hydrophobic silicone provided in Comparative Example 3.

[0098] The preparation method of the modified plastic comprises: uniformly mixing polypropylene and a coupling agent, 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 obtained modified plastics were tested as follows:

[0101] (1) Hydrophobicity test: Place the sample to be tested on a water platform, use a microsyringe to drop a certain amount of deionized water (about 5 μL) on the sample surface, and 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: Test the tensile strength and elongation at break of the material. High tensile strength and moderate elongation at break indicate good cross-linking performance and excellent mechanical properties of the material. The specific test methods are as follows:

[0103] Using a universal material testing machine, the sample (width 10 mm, thickness 5 mm) was clamped in the upper and lower clamps (the distance between the clamps was 115 mm, and stretched at a constant speed (25 m / min) until it broke, and the maximum tensile force at break was recorded, and the tensile strength was calculated according to the sample size; tensile strength = maximum tensile force / (sample width × sample thickness); and the elongation of the sample from the original length to the break was 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 can be seen from Table 1, the modified organosilicon compound provided by the present invention uses a hydroxyl-containing compound and an isocyanate mono-terminated silane as raw materials, introduces a carbamate group into the molecular chain of the organosilicon, and at the same time, the hydroxyl-containing compound adopts a specific type, and the obtained modified organosilicon material has good hydrophobicity and strong cross-linking ability, which can effectively improve the hydrophobicity and mechanical properties of the material; the contact angle of the plastic including the modified organosilicon compound is ≥104°, the tensile strength is ≥28MPa, and the elongation at break is ≥195%.

[0109] By comparing the embodiment with comparative examples 1 and 2, it can be seen that the modified organosilicon compound obtained from non-specific raw materials has poor hydrophobicity and mechanical properties of the plastic; it can be seen from comparative example 3 that, compared with conventional long carbon chain organosilicon, the modified organosilicon compound obtained by introducing a carbamate structure and using specific raw materials in the present invention can effectively improve the hydrophobicity and mechanical properties of the plastic.

[0110] The specific embodiments described above further illustrate the objectives, technical solutions and beneficial effects of the present invention in detail. It should be understood that the above description is only a specific embodiment of the present invention and is 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 in the protection scope of the present invention.

Claims

1. A modified organosilicon compound, characterized in that: The raw materials for preparing the modified organic silicon compound include a hydroxyl-containing compound and an isocyanate mono-terminated silane; The hydroxyl-containing compound includes saturated fatty alcohol and / or hydroxy silicone wax.

2. The modified organosilicon compound according to claim 1, characterized in that The number of carbon atoms in the main chain of the saturated fatty alcohol is ≥5, and more preferably the number of carbon atoms in the main chain is 8 to 22; Preferably, the saturated fatty alcohol comprises a saturated monohydric alcohol and / or a saturated dihydric alcohol, preferably a saturated monohydric alcohol.

3. The modified organosilicon compound according to claim 2, characterized in that: The saturated monohydric alcohol includes monohydric alcohol A and / or monohydric alcohol B; the number of carbon atoms in the main chain of the monohydric alcohol B is greater than the number of carbon atoms in the main chain of the monohydric alcohol A; Preferably, the monohydric alcohol A and the monohydric alcohol B each independently include at least one of pentanol, hexanol, heptanol, octanol, nonanol, decanol, decanol, lauryl alcohol, tetradecanol, hexadecanol, octadecanol, docosanol or derivatives and / or isomers of the aforementioned monohydric alcohols; Preferably, the saturated monohydric alcohol comprises monohydric alcohol A and monohydric alcohol B, and the molar ratio of the monohydric alcohol A to the monohydric alcohol B is 1:(0.5-3).

4. The modified organosilicon compound according to claim 2 or 3, characterized in that: 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 foregoing diols.

5. The modified organic silicon compound according to any one of claims 1 to 4, characterized in that: The number average molecular weight of the hydroxy silicone wax is 5000-7000 g / mol, and the hydroxyl value is 5-15 mg KOH / g; Preferably, the hydroxyl-containing compound comprises a saturated fatty alcohol and a hydroxy silicone wax, and the molar ratio of the saturated fatty alcohol to the hydroxy silicone wax is 1:(0.05-0.5), and more preferably 1:(0.1-0.3).

6. The modified organic silicon compound according to any one of claims 1 to 5, characterized in that: The isocyanate mono-terminated silane has a structure shown in Formula I; wherein R1, R2, and R3 are each independently selected from a C1-C6 straight chain or branched chain alkyl group or a C1-C6 straight chain or branched chain alkoxy group, and at least one of R1, R2, and R3 is selected from a C1-C6 straight chain or branched chain alkoxy group; n is an integer of 0 to 6; Preferably, the isocyanate mono-terminated silane includes at least one of isocyanate trimethoxysilane, isocyanate triethoxysilane, 3-isocyanate propyl trimethoxysilane, 3-isocyanate propyl triethoxysilane, 3-isocyanate methyl trimethoxysilane, 3-isocyanate ethyl trimethoxysilane, isocyanate propyl methyl dimethoxysilane or isocyanate propyl methyl diethoxysilane, and is further preferably isocyanate trimethoxysilane and / or isocyanate triethoxysilane; Preferably, in the preparation raw materials, the molar ratio of isocyanate group to hydroxyl group is (1-1.5):

1.

7. A method for preparing a modified organosilicon compound according to any one of claims 1 to 6, characterized in that: The preparation method comprises the following steps: The hydroxyl-containing compound is reacted with isocyanate mono-terminated silane to obtain the modified organic silicon compound.

8. The preparation method according to claim 7, characterized in that: The reaction temperature is 100-130°C; Preferably, the reaction time is 3 to 5 hours.

9. The preparation method according to claim 7 or 8, characterized in that: The reaction also includes a step of dehydrating the hydroxyl-containing compound before the reaction; Preferably, the dehydration temperature is 110-120° C., the pressure is ≤0.1 MPa, and the time is 0.5-2 h.

10. A hydrophobic coupling agent, characterized in that The hydrophobic coupling agent comprises the modified organic silicon compound according to any one of claims 1 to 6.

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