A modified dodecylbenzenesulfonate compound, its preparation method, its application, and a dust suppressant.

Abstract

This application relates to a modified dodecylbenzenesulfonate compound. The preparation method of the modified dodecylbenzenesulfonate compound includes: an amino substitution reaction between 3-aminobenzene-1,2-diol and ammonium polyphosphate to obtain hydroxybenzene-containing ammonium polyphosphate; and a hydroxyl dehydration reaction between the hydroxybenzene-containing ammonium polyphosphate and dodecylbenzenesulfonic acid to obtain the modified dodecylbenzenesulfonate compound, which can simultaneously play the roles of dust inhibition and dust suppression, further improving the wetting and capturing effect of water droplets on dust and the effect of inhibiting dust pollution.

Description

Technical Field

[0001] This application relates to the field of dust control technology, and more specifically, to a modified dodecylbenzenesulfonate compound, its preparation method, its application, and a dust suppressant. Background Technology

[0002] Hard rock tunnel construction generates a large amount of dust during blasting, which not only causes environmental pollution and harms human health but also reduces visibility within the tunnel. Existing tunnel dust control technologies can be categorized into six types: dust reduction technology, dust suppression technology, dust isolation technology, dust removal technology, dust removal technology, and personal protective equipment (dust barrier) technology. Spray dust suppression technology, as a simple, efficient, and environmentally friendly dust suppression method, has great potential for application in tunnels. The core of spray dust suppression technology is to atomize water and spray it into the air, allowing water droplets to collide with and capture dust particles, thereby accelerating dust settling.

[0003] To improve the wetting and capture of dust by water droplets and suppress dust pollution, chemical inhibitors need to be added to the water to enhance the dust collection capacity of atomizing dust suppression equipment. Currently, chemical inhibitors and dust suppressants on the market have achieved some results, but products that combine inhibition and dust suppression are rare. In practical applications, inhibitors and dust suppressants are often used in combination, which is not only cumbersome to use but also makes it difficult to achieve simultaneous inhibition and dust suppression. Summary of the Invention

[0004] This application addresses the aforementioned deficiencies in the prior art. There is a need for a modified dodecylbenzenesulfonate compound, its preparation method, its application, and a dust suppressant, capable of resolving the problem that the simultaneous inhibition and suppression of dust cannot be achieved when chemical inhibitors and dust suppressants are combined during dust capture.

[0005] A first aspect of this application provides a modified dodecylbenzenesulfonate compound having the structure shown in Formula I.

[0006] (I).

[0007] A second aspect of this application provides a method for preparing a modified dodecylbenzenesulfonate compound of Formula I, the method comprising: reacting 3-aminophenyl-1,2-diol and ammonium polyphosphate with an amino substitution reaction to obtain hydroxyphenyl-containing ammonium polyphosphate; and reacting the hydroxyphenyl-containing ammonium polyphosphate with dodecylbenzenesulfonic acid with a hydroxyl dehydration reaction to obtain the modified dodecylbenzenesulfonate compound.

[0008] In some embodiments, the mass ratio of 3-aminophenyl-1,2-diol to ammonium polyphosphate is 1-2:3-5.

[0009] In some embodiments, the conditions for the amino substitution reaction include conducting the reaction in a protective atmosphere and heating during the reaction.

[0010] In some embodiments, the mass ratio of ammonium hydroxyphenyl polyphosphate to dodecylbenzenesulfonic acid is 1:6 to 15.

[0011] A third aspect of this application provides the use of a modified dodecylbenzenesulfonate compound of Formula I or the preparation method described in any embodiment of this application in a dust suppressant.

[0012] A fourth aspect of this application provides a dust suppressant comprising the modified dodecylbenzenesulfonate compound of claim 1.

[0013] In some embodiments, the dust suppressant further includes a nonionic surfactant, an inhibitor, and water.

[0014] In some embodiments, the dust suppressant comprises the following components by weight: 0.5-5 parts of modified dodecylbenzenesulfonate compound, 0.2-3 parts of nonionic surfactant, 1-5 parts of inhibitor, and 70-90 parts of deionized water.

[0015] In some embodiments, the nonionic surfactant includes one or both of fatty acid diethanolamide and fatty alcohol polyoxyethylene ether.

[0016] In some embodiments, the inhibition aid includes one or both of chlorobrines and polybrominated diphenyl ethers.

[0017] The modified dodecylbenzenesulfonate compound, preparation method, application, and dust inhibitor provided in the various embodiments of this application propose a structure containing ammonium polyphosphate and having two dodecylbenzenesulfonic acid molecules, which can simultaneously exert the functions of dust inhibition and dust suppression, further improving the wetting and capture effect of water droplets on dust and the effect of inhibiting dust pollution. Detailed Implementation

[0018] To enable those skilled in the art to better understand the technical solutions of this application, the embodiments of this application will be described in further detail below with reference to specific embodiments, but this is not intended to limit this application.

[0019] The terms “first,” “second,” and similar terms used in this application do not indicate any order, quantity, or importance, but are merely used for distinction. Terms such as “including” or “comprising” mean that the element preceding the term covers the element listed after the term, and do not exclude the possibility of covering other elements as well.

[0020] According to embodiments of this application, a modified dodecylbenzenesulfonate compound is provided, the modified dodecylbenzenesulfonate compound having the structure shown in Formula I.

[0021] (I).

[0022] The modified dodecylbenzenesulfonate compound proposed in this application possesses both dust inhibition and dust suppression functions. The functional groups and structural characteristics of the modified dodecylbenzenesulfonate compound, when combined with dust, not only inhibit the generation and dispersal of dust but also suppress its diffusion. This solves the problem of simultaneously inhibiting and suppressing dust when using a combination of dust inhibitors and dust suppressants. As experimental results show, it has good dust wetting effect and a short wetting time, enabling rapid dust suppression; it also has good inhibition effect, meaning that the amount of CO released after treatment is low. In the application of dust suppressants, it can be used in conjunction with water to quickly wet, capture, and inhibit dust formation. Furthermore, the modified dodecylbenzenesulfonate compound also has good thermal stability, meaning that it can maintain a good dust inhibition effect at higher temperatures, while releasing less CO at higher temperatures.

[0023] According to embodiments of this application, a method for preparing a modified dodecylbenzenesulfonate compound of Formula I is also provided. The preparation method includes: reacting 3-aminophenyl-1,2-diol and ammonium polyphosphate with an amino substitution reaction to obtain hydroxyphenyl-containing ammonium polyphosphate; and reacting the hydroxyphenyl-containing ammonium polyphosphate with dodecylbenzenesulfonic acid with a hydroxyl dehydration reaction to obtain the modified dodecylbenzenesulfonate compound.

[0024] The synthesis route is as follows:

[0025] ;

[0026] .

[0027] The synthesized modified dodecylbenzene sulfonate compound is linked by a benzene ring, giving it not only the structure of ammonium polyphosphate but also two dodecylbenzene sulfonic acid molecules, thus providing it with both inhibition and dust suppression properties.

[0028] In some embodiments, the mass ratio of 3-aminophenyl-1,2-diol to ammonium polyphosphate is 1-2:3-5.

[0029] In some embodiments, the conditions for the amino substitution reaction include reacting under a protective atmosphere and heating during the reaction. In some embodiments, the temperature of the amino substitution reaction is 60-100°C; preferably, the temperature of the amino substitution reaction is 80-95°C. In some embodiments, the time of the amino substitution reaction is 0.5-3 hours. Preferably, the time of the amino substitution reaction is 1-2 hours. In some embodiments, the product of the amino substitution reaction is filtered, washed, and dried to obtain ammonium polyphosphate containing hydroxyphenylene. The drying temperature is 50-90°C, and the drying time is 5-15 hours. Preferably, the drying temperature is 70-85°C, and the drying time is 8-13 hours.

[0030] In some embodiments, 3-aminophenyl-1,2-diol and ammonium polyphosphate are mixed in water and subjected to an amino substitution reaction.

[0031] In some embodiments, the mass ratio of ammonium hydroxyphenyl polyphosphate to dodecylbenzenesulfonic acid is 1:6 to 15.

[0032] In some embodiments, the hydroxyl dehydration reaction involves mixing ammonium hydroxyphenyl polyphosphate and dodecylbenzenesulfonic acid in water and carrying out the hydroxyl dehydration reaction.

[0033] In some embodiments, the temperature of the hydroxyl dehydration reaction is room temperature. In some embodiments, the reaction time is 10-40 min. Preferably, the reaction time is 20-30 min.

[0034] In some embodiments, the product obtained from the hydroxyl dehydration reaction is filtered, washed, and dried to obtain a modified dodecylbenzenesulfonate compound. The drying temperature is 40-70°C, and the drying time is 15-30 hours.

[0035] According to embodiments of this application, the application of a modified dodecylbenzenesulfonate compound of Formula I or the preparation method described in any embodiment of this application in dust suppressants is also provided. The modified dodecylbenzenesulfonate compound has dust inhibition and dust suppression effects and can be used in dust suppressants.

[0036] According to embodiments of this application, a dust suppressant is also provided, the dust suppressant comprising the modified dodecylbenzenesulfonate compound described in any embodiment of this application.

[0037] In some embodiments, the dust suppressant further includes a nonionic surfactant, an inhibitor, and water.

[0038] Modified dodecylbenzenesulfonate compound has both dust inhibition and dust suppression effects. Nonionic surfactant has the effect of reducing surface tension, and inhibition aid has the effect of synergistically inhibiting dust by modified dodecylbenzenesulfonate compound. The synergistic effect of nonionic surfactant and inhibition aid with modified dodecylbenzenesulfonate compound is better than that of surfactant alone in terms of dust wetting ability and surface tension reduction effect. It can reduce the wetting time of water droplets on dust, reduce surface tension to a greater extent, and also has a better inhibition rate.

[0039] In some embodiments, the dust suppressant comprises the following components by weight: 0.5-5 parts of modified dodecylbenzenesulfonate compound, 0.2-3 parts of nonionic surfactant, 1-5 parts of inhibitor, and 70-90 parts of deionized water.

[0040] Dust inhibitors have a shorter wetting time for dust, a greater reduction in surface tension, and a better inhibition rate, which allows them to better perform their function of wetting, capturing, and inhibiting dust.

[0041] In some embodiments, the nonionic surfactant comprises any one or both of fatty acid diethanolamide and fatty alcohol polyoxyethylene ether. In some embodiments, when the nonionic surfactant comprises fatty acid diethanolamide and fatty alcohol polyoxyethylene ether, the mass ratio of fatty acid diethanolamide to fatty alcohol polyoxyethylene ether is 1:2-3; for example, 1:2.5. The combination of these two surfactants, fatty acid diethanolamide and fatty alcohol polyoxyethylene ether, can improve surface activity and also better interact with modified dodecylbenzenesulfonate compounds.

[0042] In some embodiments, the inhibitor includes one or both of chlorobrines and polybrominated diphenyl ethers. In some embodiments, when the inhibitor includes chlorobrines and polybrominated diphenyl ethers, the mass ratio of chlorobrines to polybrominated diphenyl ethers is 1-3:3; for example, 2:3. The combination of chlorobrines and polybrominated diphenyl ethers as inhibitors can better cooperate with the modified dodecylbenzenesulfonate compound to exert its inhibitory effect.

[0043] According to embodiments of this application, a method for preparing a dust suppressant as described in any embodiment of this application is also provided. The preparation method includes mixing a modified dodecylbenzene sulfonate compound, a nonionic surfactant, an inhibitor, and water to obtain a dust suppressant.

[0044] You can first mix any one material with water, then add the remaining two materials. For example, first add the modified dodecylbenzenesulfonate compound and water (stir for 5-30 minutes), then add the nonionic surfactant and inhibitor in random order; or, mix all the materials together, then add water. After adding the materials, you can perform ultrasonic treatment for 5-20 minutes.

[0045] Example 1

[0046] A dust suppressant comprises the following components in parts by weight: 0.5 parts of modified dodecylbenzenesulfonate compound, 0.2 parts of nonionic surfactant, 1 part of inhibitor, and 70 parts of deionized water.

[0047] The preparation process of the modified dodecylbenzenesulfonate compound includes the following steps:

[0048] a. Place 15g of 3-aminophenyl-1,2-diol and 50g of ammonium polyphosphate into a three-necked flask containing 500ml of distilled water, and heat at 90℃ under a nitrogen atmosphere with magnetic stirring for 2h.

[0049] b. Vacuum filter and wash the sample, then dry it at 80℃ for 12 hours to obtain ammonium polyphosphate containing hydroxyphenylene.

[0050] c. Place 3 g of ammonium polyphosphate containing hydroxyphenyl and 30 g of dodecylbenzenesulfonic acid into a three-necked flask containing 300 ml of distilled water, stir at 800 rpm for 30 min at room temperature, then vacuum filter the sample and wash it 5 times before drying it at 60 °C for 24 h to obtain the modified dodecylbenzenesulfonate compound.

[0051] The nonionic surfactant is a mixture of fatty acid diethanolamide and fatty alcohol polyoxyethylene ether, with a mass ratio of fatty acid diethanolamide to fatty alcohol polyoxyethylene ether of 1:2.5.

[0052] The inhibition aid is a mixture of chlorinated anhydride and polybrominated diphenyl ether, with a mass ratio of chlorinated anhydride to polybrominated diphenyl ether of 2:3.

[0053] The preparation process of dust suppressant includes the following steps:

[0054] a. Add the modified dodecylbenzenesulfonate compound to deionized water, and then stir vigorously in a high-speed homogenizer for 10 minutes;

[0055] b. Add an inhibitor to the mixture and sonicate the mixture at 150W for 10 minutes.

[0056] c. Add the nonionic surfactant to the mixture and stir the mixture for 30 minutes to obtain a dust inhibitor containing a modified dodecylbenzenesulfonate compound.

[0057] Example 2

[0058] A dust suppressant comprises the following components in parts by weight: 2 parts modified dodecylbenzenesulfonate compound, 2 parts nonionic surfactant, 3 parts inhibitor, and 80 parts deionized water.

[0059] The preparation process of the modified dodecylbenzenesulfonate compound includes the following steps:

[0060] a. Place 18g of 3-aminophenyl-1,2-diol and 60g of ammonium polyphosphate into a three-necked flask containing 500ml of distilled water, and heat at 90℃ under a nitrogen atmosphere with magnetic stirring for 2h.

[0061] b. Vacuum filter and wash the sample, then dry it at 80℃ for 12 hours to obtain ammonium polyphosphate containing hydroxyphenylene.

[0062] c. Place 4g of ammonium polyphosphate containing hydroxyphenyl and 35g of dodecylbenzenesulfonic acid into a three-necked flask containing 300ml of distilled water, stir at 800rpm for 30min at room temperature, then vacuum filter the sample and wash it 5 times before drying it at 60℃ for 24h to obtain the modified dodecylbenzenesulfonate compound.

[0063] The nonionic surfactant is a mixture of fatty acid diethanolamide and fatty alcohol polyoxyethylene ether, with a mass ratio of fatty acid diethanolamide to fatty alcohol polyoxyethylene ether of 1:2.5.

[0064] The inhibition aid is a mixture of chlorinated anhydride and polybrominated diphenyl ether, with a mass ratio of chlorinated anhydride to polybrominated diphenyl ether of 2:3.

[0065] The preparation process of dust suppressant includes the following steps:

[0066] a. Add the modified dodecylbenzenesulfonate compound to deionized water, and then stir vigorously in a high-speed homogenizer for 15 minutes;

[0067] b. Add an inhibitor to the mixture and sonicate the mixture at 160W for 12 minutes.

[0068] c. Add the nonionic surfactant to the mixture and stir the mixture for 30 minutes to obtain a novel dust inhibitor containing a modified dodecylbenzenesulfonate compound.

[0069] Example 3

[0070] A dust suppressant comprises the following components in parts by weight: 5 parts of modified dodecylbenzenesulfonate compound, 3 parts of nonionic surfactant, 5 parts of inhibitor, and 90 parts of deionized water.

[0071] The preparation process of the modified dodecylbenzenesulfonate compound includes the following steps:

[0072] a. Place 23g of 3-aminophenyl-1,2-diol and 65g of ammonium polyphosphate into a three-necked flask containing 500ml of distilled water, and heat at 90℃ under a nitrogen atmosphere with magnetic stirring for 2h.

[0073] b. Vacuum filter and wash the sample, then dry it at 80℃ for 12 hours to obtain ammonium polyphosphate containing hydroxyphenylene.

[0074] c. Place 5g of ammonium polyphosphate containing hydroxyphenylene and 40g of dodecylbenzenesulfonic acid into a three-necked flask containing 300ml of distilled water, stir at 800rpm for 30min at room temperature, then vacuum filter the sample and wash it 5 times before drying it at 60℃ for 24h to obtain the modified dodecylbenzenesulfonate compound.

[0075] The nonionic surfactant is a mixture of fatty acid diethanolamide and fatty alcohol polyoxyethylene ether, with a mass ratio of fatty acid diethanolamide to fatty alcohol polyoxyethylene ether of 1:2.5.

[0076] The inhibition aid is a mixture of chlorinated anhydride and polybrominated diphenyl ether, with a mass ratio of chlorinated anhydride to polybrominated diphenyl ether of 2:3.

[0077] The preparation process of dust suppressant includes the following steps:

[0078] a. Add the modified dodecylbenzenesulfonate compound to deionized water, and then stir vigorously in a high-speed homogenizer for 20 minutes;

[0079] b. Add an inhibitor to the mixture and sonicate the mixture at 170W for 15 minutes.

[0080] c. Add the nonionic surfactant to the mixture and stir the mixture for 30 minutes to obtain a novel dust inhibitor containing a modified dodecylbenzenesulfonate compound.

[0081] Comparative Example 1

[0082] The dust suppressant comprises the following components in parts by weight: 5 parts polyether-modified trisiloxane and 90 parts deionized water.

[0083] The preparation process of the dust suppressant includes the following steps:

[0084] Polyether-modified trisiloxane was added to deionized water and then vigorously stirred in a high-speed homogenizer for 20 minutes to obtain a dust inhibitor.

[0085] Comparative Example 2

[0086] Dust suppressant, comprising the following components in parts by weight: 3 parts nonionic surfactant, 5 parts inhibitor, and 80 parts deionized water.

[0087] The preparation process of dust suppressant includes the following steps:

[0088] a. Add the modified dodecylbenzenesulfonate compound to deionized water, and then stir vigorously in a high-speed homogenizer for 20 minutes;

[0089] b. Add an inhibitor to the mixture and sonicate the mixture at 170W for 15 minutes.

[0090] c. Add the nonionic surfactant to the mixture and stir the mixture for 30 minutes to obtain a novel dust inhibitor containing a modified dodecylbenzenesulfonate compound.

[0091] Dust suppression experiments were conducted on the dust suppressants of Examples 1-3 and the comparative examples. The dust suppression effects of the dust suppressants of Examples 1-3 and the comparative examples are shown in Table 1.

[0092] Table 1. Surface tension and wetting time of dust inhibitors in Examples 1-3 and comparative examples

[0093]

[0094] As shown in Table 1, compared to the comparative example, the wetting time and surface tension of Examples 1-3 are both shorter. This indicates that the dust suppressant prepared in this application has a superior dust suppression effect. The wetting time and surface tension of the dust suppressants in Examples 1-3 of this application are relatively comparable, demonstrating that even with different ratios of nonionic surfactant and inhibitor to the modified dodecylbenzenesulfonate compound, a good dust suppression effect can still be achieved. Compared to the comparative example where surfactant is added alone, the addition of the modified dodecylbenzenesulfonate compound significantly shortens the wetting time and reduces the surface tension.

[0095] Thermal stability tests were conducted on the dust inhibitors in Examples 1-3 and the comparative example. In the thermal stability test, inhibition rate is an important parameter for evaluating the thermal stability of each additive; the lower the CO concentration, the better the thermal stability effect. The specific method was as follows: three 20g samples (100-mesh coal powder and rock powder = 1:5) were weighed and thoroughly mixed with Examples 1-3 and the comparative example (each 20g). The mixtures were dried to constant weight in a 60℃ forced-air drying oven. The clumps were crushed and placed into three three-necked flasks, and an air pump was connected. A thermometer was placed inside, and the gas flow rate was set to 250mL / min. The three-necked flasks were then placed in an oil bath, with the temperature range being 110~130℃. The CO concentration was measured using a CO gas detector every 10℃ increase.

[0096] Table 2. CO concentration / ppm of samples after treatment in Examples 1-3 and comparative examples at different temperatures.

[0097]

[0098] Table 2 shows that, compared to the comparative example, the CO concentration of the samples treated in Examples 1-3 and after treatment was significantly reduced at different temperatures. This indicates that the dust suppressant prepared in this application has superior thermal stability, maintaining a good dust suppression effect even at higher temperatures of 110-130°C. Furthermore, the CO concentrations of the samples treated at higher temperatures in Examples 1-3 of this application are relatively similar at different temperatures, demonstrating that even with different ratios of nonionic surfactants and inhibitors to the modified dodecylbenzenesulfonate compound, a good dust suppression effect can still be achieved at higher temperatures.

[0099] Furthermore, although exemplary embodiments have been described herein, their scope includes any and all embodiments based on this application that have equivalent elements, modifications, omissions, combinations (e.g., schemes involving intersections of various embodiments), adaptations, or alterations. Elements in the claims will be interpreted broadly based on the language used in the claims and are not limited to the examples described in this specification or during the implementation of this application, which will be interpreted as non-exclusive. Therefore, this specification and examples are intended to be considered illustrative only, and the true scope and spirit are indicated by the following claims and the full scope of their equivalents.

[0100] The above description is intended to be illustrative and not restrictive. For example, the above examples (or one or more of them) can be used in combination with each other. Other embodiments may be used by those skilled in the art upon reading the above description. Furthermore, in the above detailed description, various features may be grouped together to simplify the application. This should not be construed as an intention that a feature of an unclaimed application is necessary for any claim. Rather, the subject matter of this application may be less than all the features of an embodiment of a particular application. Thus, the following claims are incorporated herein by reference as examples or embodiments, wherein each claim is independently considered as a separate embodiment, and these embodiments are contemplated as being possible in various combinations or arrangements. The scope of the invention should be determined by reference to the appended claims and the full scope of their equivalents.

[0101] The above embodiments are merely exemplary embodiments of this application and are not intended to limit the present invention. The scope of protection of the present invention is defined by the claims. Those skilled in the art can make various modifications or equivalent substitutions to the present invention within the spirit and scope of this application, and such modifications or equivalent substitutions should also be considered to fall within the scope of protection of the present invention.

Claims

1. A modified dodecylbenzenesulfonate compound, characterized in that, The modified dodecylbenzenesulfonate compound has the structure shown in Formula I. （I）。 2. A method for preparing the modified dodecylbenzenesulfonate compound according to claim 1, characterized in that, The preparation method includes: 3-aminophenyl-1,2-diol and ammonium polyphosphate undergoing an amino substitution reaction to obtain hydroxyphenyl-containing ammonium polyphosphate; and hydroxyphenyl-containing ammonium polyphosphate and dodecylbenzenesulfonic acid undergoing a hydroxyl dehydration reaction to obtain a modified dodecylbenzenesulfonate compound.

3. The preparation method according to claim 2, characterized in that, The mass ratio of 3-aminophenyl-1,2-diol to ammonium polyphosphate is 1-2:3-5.

4. The preparation method according to claim 2, characterized in that, The conditions for the amino substitution reaction include conducting the reaction in a protective atmosphere and heating during the reaction.

5. The preparation method according to claim 2, characterized in that, The mass ratio of hydroxyphenyl polyphosphate ammonium to dodecylbenzenesulfonic acid is 1:6~15.

6. The use of the modified dodecylbenzenesulfonate compound of claim 1 or the preparation method of any one of claims 2-5 in a dust suppressant.

7. A dust suppressant, characterized in that, The dust suppressant comprises the modified dodecylbenzenesulfonate compound of claim 1.

8. The dust suppressant according to claim 7, characterized in that, The dust suppressant also includes nonionic surfactants, inhibitors, and water.

9. The dust suppressant according to claim 7, characterized in that, The dust suppressant comprises the following components by weight: 0.5-5 parts of modified dodecylbenzenesulfonate compound, 0.2-3 parts of nonionic surfactant, 1-5 parts of inhibitor, and 70-90 parts of deionized water.

10. The dust suppressant according to claim 8, characterized in that, The nonionic surfactant includes any one or both of fatty acid diethanolamide and fatty alcohol polyoxyethylene ether.

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