Modified dodecylbenzene sulfonate compound, preparation method, application and dust inhibitor

Abstract

The embodiment of the invention relates to a modified dodecylbenzene sulfonate compound, and a preparation method of the modified dodecylbenzene sulfonate compound comprises the following steps: carrying out amino substitution reaction on 3-aminobenzene-1, 2-diol and ammonium polyphosphate to obtain ammonium polyphosphate containing hydroxyl benzene; the ammonium polyphosphate containing hydroxyl benzene and dodecylbenzene sulfonic acid are subjected to hydroxyl dehydration reaction to obtain a modified dodecylbenzene sulfonic compound, so that the dust inhibition and dust suppression effects can be achieved at the same time, and the infiltration capture effect of water drops on dust and the dust pollution suppression effect are further improved.

Description

Technical Field

[0001] The present application relates to the technical field of dust treatment, and more specifically, to a modified dodecylbenzene sulfonate compound, a preparation method, an application and a dust suppressant. Background Art

[0002] A large amount of dust is generated during the blasting and excavation of hard rock tunnels, which not only causes environmental pollution and harms human health, but also reduces visibility in the tunnel. Existing tunnel dust prevention technologies can be divided into six categories, including dust reduction technology, dust suppression technology, dust isolation technology, dust exhaust technology, dust removal technology and personal protection (dust prevention) technology. Spray dust suppression technology, as a simple, efficient and green dust suppression technology, has great potential for application in tunnels. The core of spray dust suppression technology is to spray water mist into the air through water atomization, so that water droplets collide with dust particles and capture them, thereby accelerating dust settling.

[0003] In order to improve the infiltration and capture of dust by water droplets and suppress dust pollution, it is necessary to add chemical inhibitors to the water to improve the dust capture capacity of the atomization dust reduction equipment. The chemical inhibitors and dust suppressants currently used in the market have achieved certain results, but there are few products that can combine inhibition and dust suppression. In practical applications, most inhibitors and dust suppressants are used in combination, which is not only cumbersome to use, but also difficult to achieve simultaneous inhibition and dust suppression. Summary of the invention

[0004] The present application is provided to solve the above defects existing in the prior art. A modified dodecylbenzene sulfonate compound, preparation method, application and dust suppressant are needed to solve the problem that adding a chemical inhibitor and a dust suppressant compound in the process of capturing dust cannot achieve simultaneous inhibition and dust suppression.

[0005] In a first aspect of the present application, a modified dodecylbenzene sulfonate compound is provided. The modified dodecylbenzene sulfonate compound has a structure shown in Formula I. (I).

[0006] In a second aspect of the present application, a method for preparing a modified dodecylbenzene sulfone compound shown in formula I is provided, the method comprising: subjecting 3-aminobenzene-1,2-diol and ammonium polyphosphate to an amino substitution reaction to obtain hydroxyl-containing ammonium benzene polyphosphate; and subjecting hydroxyl-containing ammonium benzene polyphosphate to a hydroxyl dehydration reaction with dodecylbenzene sulfonic acid to obtain a modified dodecylbenzene sulfone compound.

[0007] In some embodiments, the mass ratio of 3-aminobenzene-1,2-diol to ammonium polyphosphate is 1-2:3-5.

[0008] In some embodiments, the conditions for the amino substitution reaction include conducting the reaction in a protective atmosphere and heating during the reaction.

[0009] In some embodiments, the mass ratio of hydroxyl-containing benzene ammonium polyphosphate to dodecylbenzene sulfonic acid is 1:6-15.

[0010] The third aspect of the present application provides an application of a modified dodecylbenzene sulfonate compound shown in Formula I or the preparation method described in any embodiment of the present application in a dust suppressant.

[0011] In a fourth aspect of the present application, a dust suppressant is provided, wherein the dust suppressant comprises the modified dodecylbenzene sulfonate compound according to claim 1.

[0012] In some embodiments, the dust suppressant further includes a nonionic surfactant, an inhibitor and water.

[0013] In some embodiments, the weight proportions of the components in the dust suppressant are: 0.5-5 parts of modified dodecylbenzene sulfonate compound, 0.2-3 parts of nonionic surfactant, 1-5 parts of inhibitor, and 70-90 parts of deionized water.

[0014] In some embodiments, the nonionic surfactant includes any one or both of fatty acid diethanolamide and fatty alcohol polyoxyethylene ether.

[0015] In some embodiments, the inhibitor comprises any one or both of chlorohydric anhydride and polybrominated diphenyl ether.

[0016] The modified dodecylbenzene sulfonate compounds, preparation methods, applications and dust suppressants provided in the various embodiments of the present application propose a structure that contains ammonium polyphosphate and two dodecylbenzene sulfonic acid molecules, which can simultaneously play the role of dust inhibition and dust suppression, further improving the dust infiltration and capture effect of water droplets and the effect of suppressing dust pollution. DETAILED DESCRIPTION

[0017] In order to enable those skilled in the art to better understand the technical solution of the present application, the embodiments of the present application are further described in detail below in conjunction with specific embodiments, but this is not intended to limit the present application.

[0018] The words "first", "second" and similar words used in this application do not indicate any order, quantity or importance, but are only used to distinguish. The words "include" or "comprise" and similar words mean that the elements before the word include the elements listed after the word, and do not exclude the possibility of including other elements.

[0019] According to an embodiment of the present application, a modified dodecylbenzene sulfonate compound is provided. The modified dodecylbenzene sulfonate compound has a structure shown in Formula I. (I).

[0020] The modified dodecylbenzene sulfone compound proposed in the present application has the effects of dust inhibition and dust suppression at the same time. The functional groups and structural characteristics of the modified dodecylbenzene sulfone compound enable it to not only inhibit the generation and flying of dust after combining with dust, but also suppress the diffusion of dust, which can solve the problem that the inhibitor and dust suppressant cannot achieve the effects of dust inhibition and dust suppression at the same time when they are used in combination for dust reduction. As shown in the experimental results, the wetting effect on dust is good, and the wetting time is short, that is, the dust can be quickly reduced; it also has a good inhibitory effect, that is, the amount of CO released after treatment is small. In the application of dust suppressants, it can be combined with water to quickly infiltrate and capture dust and suppress dust formation. In addition, the modified dodecylbenzene sulfone compound also has good thermal stability, that is, it can better exert the effect of dust inhibition at higher temperatures, and the amount of CO released at higher temperatures is small.

[0021] According to an embodiment of the present application, a method for preparing a modified dodecylbenzene sulfonate compound shown in formula I is also provided, the preparation method comprising: 3-aminobenzene-1,2-diol and ammonium polyphosphate undergo an amino substitution reaction to obtain hydroxyl-containing benzene ammonium polyphosphate; hydroxyl-containing benzene ammonium polyphosphate and dodecylbenzene sulfonic acid undergo a hydroxyl dehydration reaction to obtain a modified dodecylbenzene sulfonate compound.

[0022] The synthetic route is as follows: ; .

[0023] The synthesized modified dodecylbenzene sulfonate compound is connected by a benzene ring, so that the modified dodecylbenzene sulfonate compound not only has the structure of ammonium polyphosphate, but also has two dodecylbenzene sulfonic acid molecules, so that it has not only the inhibitory property but also the dust suppression property.

[0024] In some embodiments, the mass ratio of 3-aminobenzene-1,2-diol to ammonium polyphosphate is 1-2:3-5.

[0025] In some embodiments, the conditions of the amino substitution reaction include reacting in 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 0.5-3h. Preferably, the time of the amino substitution reaction is 1-2h. In some embodiments, the product of the amino substitution reaction is filtered, washed and dried to obtain hydroxyl-containing benzene ammonium polyphosphate. The drying temperature is 50-90°C and the drying time is 5-15h. Preferably, the drying temperature is 70-85°C and the drying time is 8-13h.

[0026] In some embodiments, in the amino substitution reaction, 3-aminobenzene-1,2-diol and ammonium polyphosphate are mixed in water and subjected to an amino substitution reaction.

[0027] In some embodiments, the mass ratio of hydroxyl-containing benzene ammonium polyphosphate to dodecylbenzene sulfonic acid is 1:6-15.

[0028] In some embodiments, in the hydroxyl dehydration reaction, hydroxyl-containing ammonium polyphosphate and dodecylbenzene sulfonic acid are mixed in water and subjected to a hydroxyl dehydration reaction.

[0029] In some embodiments, the temperature of the hydroxyl dehydration reaction is room temperature. In some embodiments, the time of the hydroxyl dehydration reaction is 10-40 minutes. Preferably, the reaction time is 20-30 minutes.

[0030] In some embodiments, the product obtained by the hydroxyl dehydration reaction is filtered, washed and dried to obtain a modified dodecylbenzene sulfonate compound. The drying temperature is 40-70° C. and the drying time is 15-30 hours.

[0031] According to the embodiments of the present application, there is also provided a use of a modified dodecylbenzene sulfonate compound shown in Formula I or a preparation method described in any embodiment of the present application in a dust suppressant. The modified dodecylbenzene sulfonate compound has the function of dust inhibition and dust suppression and can be used in a dust suppressant.

[0032] According to an embodiment of the present application, a dust suppressant is further provided, and the dust suppressant includes the modified dodecylbenzene sulfonate compound described in any embodiment of the present application.

[0033] In some embodiments, the dust suppressant further includes a nonionic surfactant, an inhibitor and water.

[0034] The modified dodecylbenzene sulfonate compound has both dust inhibition and dust suppression effects, the nonionic surfactant has the effect of reducing surface tension, and the inhibitor auxiliary agent has a synergistic effect with the modified dodecylbenzene sulfonate compound to inhibit dust. The nonionic surfactant and the inhibitor auxiliary agent act synergistically with the modified dodecylbenzene sulfonate compound, and have better dust wetting ability and surface tension reduction effects than a single surfactant, can reduce the wetting time of water droplets on dust and reduce surface tension to a greater extent, and can also have a better inhibition rate.

[0035] In some embodiments, the weight proportions of the components in the dust suppressant are: 0.5-5 parts of modified dodecylbenzene sulfonate compound, 0.2-3 parts of nonionic surfactant, 1-5 parts of inhibitor, and 70-90 parts of deionized water.

[0036] Dust suppressants have a shorter wetting time for dust, significantly reduce surface tension and have a better inhibition rate, which enables the dust suppressants to better play the role of wetting, capturing and suppressing dust.

[0037] In some embodiments, the nonionic surfactant includes any one or both of fatty acid diethanolamide and fatty alcohol polyoxyethylene ether. In some embodiments, when the nonionic surfactant includes 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 fatty acid diethanolamide and fatty alcohol polyoxyethylene ether can improve the surface activity effect and can also better cooperate with the modified dodecylbenzene sulfone compound.

[0038] In some embodiments, the inhibitor comprises any one or both of chloroanhydride and polybrominated diphenyl ether. In some embodiments, when the inhibitor comprises chloroanhydride and polybrominated diphenyl ether, the mass ratio of chloroanhydride and polybrominated diphenyl ether is 1-3:3; for example, 2:3. The inhibitor comprising chloroanhydride and polybrominated diphenyl ether can better cooperate with the modified dodecylbenzene sulfone compound to exert the inhibitory effect.

[0039] According to an embodiment of the present application, there is also provided a method for preparing the dust suppressant described in any embodiment of the present application, the preparation method comprising: mixing a modified dodecylbenzene sulfonate compound, a nonionic surfactant, an inhibitor and water to obtain a dust suppressant.

[0040] Any one of the materials can be mixed with water first, and then the remaining two materials can be added, for example, the modified dodecylbenzene sulfonate compound can be mixed with water first (stirred for 5-30 minutes), and then the nonionic surfactant and the inhibitor can be added randomly; or, each material can be mixed, and then water can be added. After the materials are added, ultrasonic treatment can be performed, and the ultrasonic treatment time is 5-20 minutes.

[0041] Example 1 A dust suppressant comprises the following components in parts by weight: 0.5 parts of a modified dodecylbenzene sulfonate compound, 0.2 parts of a nonionic surfactant, 1 part of an inhibitor, and 70 parts of deionized water.

[0042] The preparation process of the modified dodecylbenzene sulfonate compound comprises the following steps: a. Place 15 g of 3-aminobenzene-1,2-diol and 50 g of ammonium polyphosphate in a three-necked flask filled with 500 ml of distilled water, and heat at 90 °C with magnetic stirring for 2 h in a nitrogen atmosphere; b. The sample was vacuum filtered and washed, and then dried at 80° C. for 12 h to obtain hydroxybenzene-containing ammonium polyphosphate; c. Put 3 g of hydroxybenzene ammonium polyphosphate and 30 g of dodecylbenzene sulfonic acid into a three-necked flask filled with 300 ml of distilled water, stir at 800 rpm for 30 min at room temperature, then vacuum filter and wash the sample 5 times and dry it at 60°C for 24 h to obtain a modified dodecylbenzene sulfonate compound.

[0043] The nonionic surfactant is a mixture of fatty acid diethanolamide and fatty alcohol polyoxyethylene ether, and the mass ratio of fatty acid diethanolamide to fatty alcohol polyoxyethylene ether is 1:2.5.

[0044] The inhibitor is a mixture of chloroanhydride and polybrominated diphenyl ether, and the mass ratio of chloroanhydride to polybrominated diphenyl ether is 2:3.

[0045] The preparation process of dust suppressant includes the following steps: a. Add the modified dodecylbenzene sulfonate compound into deionized water and then stir vigorously in a high-speed homogenizer for 10 minutes; b. Adding an inhibitor to the mixture, subjecting the mixture to ultrasonic treatment at 150W for 10min; c. Add a nonionic surfactant to the mixture, and stir the mixture for 30 minutes to obtain a dust suppressant containing a modified dodecylbenzene sulfonate compound.

[0046] Example 2 A dust suppressant comprises the following components in parts by weight: 2 parts of a modified dodecylbenzene sulfonate compound, 2 parts of a nonionic surfactant, 3 parts of an inhibitor aid, and 80 parts of deionized water.

[0047] The preparation process of the modified dodecylbenzene sulfonate compound comprises the following steps: a. Place 18 g of 3-aminobenzene-1,2-diol and 60 g of ammonium polyphosphate in a three-necked flask filled with 500 ml of distilled water, and heat at 90°C with magnetic stirring for 2 h in a nitrogen atmosphere; b. The sample was vacuum filtered and washed, and then dried at 80° C. for 12 h to obtain hydroxybenzene-containing ammonium polyphosphate; c. Put 4 g of hydroxybenzene ammonium polyphosphate and 35 g of dodecylbenzene sulfonic acid into a three-necked flask filled with 300 ml of distilled water, stir at 800 rpm for 30 min at room temperature, then vacuum filter and wash the sample 5 times, and dry it at 60°C for 24 h to obtain a modified dodecylbenzene sulfone compound.

[0048] The nonionic surfactant is a mixture of fatty acid diethanolamide and fatty alcohol polyoxyethylene ether, and the mass ratio of fatty acid diethanolamide to fatty alcohol polyoxyethylene ether is 1:2.5.

[0049] The inhibitor is a mixture of chloroanhydride and polybrominated diphenyl ether, and the mass ratio of chloroanhydride to polybrominated diphenyl ether is 2:3.

[0050] The preparation process of dust suppressant includes the following steps: a. Add the modified dodecylbenzene sulfonate compound into deionized water and then stir vigorously in a high-speed homogenizer for 15 minutes; b. Add an inhibitor to the mixture and subject the mixture to ultrasonic treatment at 160W for 12min; c. Add a nonionic surfactant to the mixture, and stir the mixture for 30 minutes to obtain a novel dust suppressant containing a modified dodecylbenzene sulfonate compound.

[0051] Example 3 A dust suppressant comprises the following components in parts by weight: 5 parts of a modified dodecylbenzene sulfonate compound, 3 parts of a nonionic surfactant, 5 parts of an inhibitor aid, and 90 parts of deionized water.

[0052] The preparation process of the modified dodecylbenzene sulfonate compound comprises the following steps: a. Place 23 g of 3-aminobenzene-1,2-diol and 65 g of ammonium polyphosphate in a three-necked flask filled with 500 ml of distilled water, and heat at 90°C with magnetic stirring for 2 h in a nitrogen atmosphere; b. The sample was vacuum filtered and washed, and then dried at 80° C. for 12 h to obtain hydroxybenzene-containing ammonium polyphosphate; c. Place 5 g of hydroxybenzene-containing ammonium polyphosphate and 40 g of dodecylbenzene sulfonic acid in a three-necked flask filled with 300 ml of distilled water, stir at 800 rpm for 30 min at room temperature, then vacuum filter and wash the sample 5 times, and dry it at 60°C for 24 h to obtain a modified dodecylbenzene sulfone compound.

[0053] The nonionic surfactant is a mixture of fatty acid diethanolamide and fatty alcohol polyoxyethylene ether, and the mass ratio of fatty acid diethanolamide to fatty alcohol polyoxyethylene ether is 1:2.5.

[0054] The inhibitor is a mixture of chloroanhydride and polybrominated diphenyl ether, and the mass ratio of chloroanhydride to polybrominated diphenyl ether is 2:3.

[0055] The preparation process of dust suppressant includes the following steps: a. Add the modified dodecylbenzene sulfonate compound into deionized water and then stir vigorously in a high-speed homogenizer for 20 minutes; b. Adding an inhibitor to the mixture, subjecting the mixture to ultrasonic treatment at 170W for 15min; c. Add a nonionic surfactant to the mixture, and stir the mixture for 30 minutes to obtain a novel dust suppressant containing a modified dodecylbenzene sulfonate compound.

[0056] Comparative Example 1 The dust suppressant comprises the following components in parts by weight: 5 parts of polyether-modified trisiloxane and 90 parts of deionized water.

[0057] The preparation process of the dust suppressant comprises the following steps: The polyether-modified trisiloxane was added into deionized water and then vigorously stirred in a high-speed homogenizer for 20 minutes to obtain a dust suppressant.

[0058] Comparative Example 2 The dust suppressant comprises the following components in parts by weight: 3 parts of nonionic surfactant, 5 parts of inhibitor aid and 80 parts of deionized water.

[0059] The preparation process of dust suppressant includes the following steps: a. Add the modified dodecylbenzene sulfonate compound into deionized water and then stir vigorously in a high-speed homogenizer for 20 minutes; b. Adding an inhibitor to the mixture, subjecting the mixture to ultrasonic treatment at 170W for 15min; c. Add a nonionic surfactant to the mixture, and stir the mixture for 30 minutes to obtain a novel dust suppressant containing a modified dodecylbenzene sulfonate compound.

[0060] The 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.

[0061] Table 1. Surface tension of dust suppressants of Examples 1-3 and Comparative Examples and wetting time of samples It can be seen from Table 1 that compared with the comparative example, the wetting time and surface tension of Examples 1-3 are all less than that of the comparative example. It can be seen that the dust suppressant prepared by the present application has a better dust suppression effect, and the wetting time and surface tension of the dust suppressants of Examples 1-3 of the present application are relatively similar, indicating that even if the ratio of the nonionic surfactant and the inhibitor to the modified dodecylbenzene sulfonate compound is different, it can still exert a good dust suppression effect. Compared with the addition of a surfactant alone in the comparative example, the addition of the modified dodecylbenzene sulfonate compound can significantly shorten the wetting time and reduce the surface tension.

[0062] The dust suppressants of Examples 1-3 and the comparative examples were subjected to thermal stability tests. In the thermal stability tests, the retardation rate is an important parameter for measuring the thermal stability of each additive. The lower the CO concentration, the better the thermal stability effect. The specific method is: weigh 3 20g samples (100 mesh coal powder and rock powder = 1:5) and mix them with Examples 1-3 and the comparative example (both 20g) respectively, dry them in a 60°C blast drying oven to constant weight, crush the lumps and put them into 3 three-necked flasks and connect them to an air pump, put a thermometer in them, set the gas flow rate at 250mL / min, and then place the three-necked flask in an oil bath pot, the temperature rise range is 110~130°C, and the CO concentration is detected with a CO gas detector every 10°C rise.

[0063] Table 2. CO concentrations of samples treated in Examples 1-3 and Comparative Examples at different temperatures (ppm) It can be seen from Table 2 that, compared with the comparative example, the CO concentrations of the samples treated in Examples 1-3 at different temperatures are significantly reduced. It can be seen that the dust suppressant prepared in the present application has better thermal stability and can still maintain a good dust suppression effect at a higher temperature of 110-130°C. In addition, the CO concentrations of the samples treated at higher temperatures in Examples 1-3 of the present application are relatively close at different temperatures, indicating that even if the ratios of the nonionic surfactant and the inhibitor to the modified dodecylbenzene sulfone compound are different, they can still exert a good dust suppression effect at higher temperatures.

[0064] In addition, although exemplary embodiments have been described herein, the scope includes any and all embodiments based on the present application with equivalent elements, modifications, omissions, combinations (e.g., various embodiments intersecting schemes), adaptations or changes. The elements in the claims are to be interpreted broadly based on the language adopted in the claims, and are not limited to the examples described in this specification or during the practice of this application, and the examples are to be interpreted as non-exclusive. Therefore, this specification and examples are intended to be considered as examples only, and the true scope and spirit are indicated by the following claims and the full scope of their equivalents.

[0065] The above description is intended to be illustrative rather than restrictive. For example, the above examples (or one or more schemes thereof) may be used in combination with each other. For example, a person of ordinary skill in the art may use other embodiments when reading the above description. In addition, in the above-mentioned specific embodiments, various features may be grouped together to simplify the present application. This should not be interpreted as an intention that a feature of an application that does not require protection is necessary for any claim. On the contrary, the subject matter of the present application may be less than all the features of an embodiment of a particular application. Thus, the following claims are incorporated herein in the specific embodiments as examples or embodiments, wherein each claim is independently a separate embodiment, and it is considered that these embodiments may be combined with each other in various combinations or arrangements. The scope of the present invention should be determined with reference to the appended claims and the full scope of equivalent forms granted by these claims.

[0066] The above embodiments are only exemplary embodiments of the present application and are not intended to limit the present invention. The protection scope of the present invention is defined by the claims. Those skilled in the art may make various modifications or equivalent substitutions to the present invention within the essence and protection scope of the present application, and such modifications or equivalent substitutions shall also be deemed to fall within the protection scope of the present invention.

Claims

1. A modified dodecylbenzene sulfonate compound, characterized in that: The modified dodecylbenzene sulfonate compound has a structure shown in Formula I, （I）。 2. A method for preparing the modified dodecylbenzene sulfonate compound according to claim 1, characterized in that: The preparation method comprises: 3-aminobenzene-1,2-diol and ammonium polyphosphate undergo an amino substitution reaction to obtain hydroxyl-containing benzene ammonium polyphosphate; and hydroxyl-containing benzene ammonium polyphosphate and dodecylbenzene sulfonic acid undergo a hydroxyl dehydration reaction to obtain a modified dodecylbenzene sulfone compound.

3. The preparation method according to claim 2, characterized in that: The mass ratio of 3-aminobenzene-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 hydroxybenzene ammonium polyphosphate to dodecylbenzene sulfonic acid is 1:6-15.

6. Use of the modified dodecylbenzene sulfonate compound according to claim 1 or the preparation method according to any one of claims 2 to 5 in dust suppressants.

7. A dust suppressant, characterized in that: The dust suppressant comprises the modified dodecylbenzene sulfonate compound according to claim 1.

8. The dust suppressant according to claim 7, characterized in that: The dust suppressant further comprises a nonionic surfactant, an inhibitor and water.

9. The dust suppressant according to claim 7, characterized in that: The weight proportions of the components in the dust suppressant are: 0.5-5 parts of modified dodecylbenzene sulfonate 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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