Alkyl ether polyoxyethylene ether benzene sulfonic acid and preparation method and application thereof

By developing alkyl ether polyoxyethylene ether benzenesulfonic acid without benzenecycloalkyl substituents, the problem of degradation of linear alkyl benzenesulfonate in hard water is solved, and its personal Highly efficient application and low irritation in cleaning care supplies.

CN114907239BActive Publication Date: 2025-01-07GUANGZHOU LONKEY DAILY CHEM CO LTD
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Patent Information

Application Number
CN202210549643.6
Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
Filing Date
2022-05-20
Publication Date
2025-01-07
Estimated Expiration
2042-05-20

AI Technical Summary

Technical Problem

The existing linear alkylbenzene sulfonate has reduced washing ability in hard water, poor biodegradability and strong irritation, limiting its application in personal cleaning and care products.

Method used

Developed an alkyl ether polyoxyethylene ether benzenesulfonic acid, which has no benzene cycloalkyl substituents, and is formed with sulfur trioxide after reaction of fatty alcohol polyoxyethylene ether and phenol, which has good biodegradability and Hard water resistance and obtain corresponding salt form through neutralization reaction to improve emulsification effect.

Benefits of technology

The alkyl ether polyoxyethylene ether benzenesulfonic acid has achieved biodegradability and strong hard water resistance, reducing irritability, and is suitable for industrial detergents and personal cleaning and care products, improving the performance of the product.

✦ Generated by Eureka AI based on patent content.

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Abstract

The present invention provides an alkyl ether polyoxyethylene ether benzene sulfonic acid and a preparation method and application thereof, and relates to the technical field of surfactants. The alkyl ether polyoxyethylene ether benzene sulfonic acid of the present invention has a structure as shown in Formula I, and has the advantages of being biodegradable, having strong hard water resistance, and having low irritation. The present invention can be prepared by the following method: using fatty alcohol polyoxyethylene ether and phenol as reactants, adding a catalyst, and reacting to obtain phenyl alkyl ether polyoxyethylene ether; using phenyl alkyl ether polyoxyethylene ether and sulfur trioxide as reactants, and reacting to obtain alkyl ether polyoxyethylene ether benzene sulfonic acid. The alkyl benzene sulfonic acid of the present invention can be used as a surfactant to prepare personal cleaning and care products, which can reduce the irritation of the product and improve the biological biodegradability and hard water resistance.
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Description

Technical Field

[0001] The invention relates to the technical field of surfactants, and in particular to an alkyl ether polyoxyethylene ether benzene sulfonic acid and a preparation method and application thereof, in particular to application in personal cleaning and care products. Background Art

[0002] Alkylbenzene sulfonic acid Where R = C 11 ~C 13 ) is an important anionic surfactant, commonly used as a raw material for detergents, to produce sodium salt, ammonium salt and ethanolamine salt of alkylbenzene sulfonic acid. Alkylbenzene sulfonate is the neutralization product of alkylbenzene sulfonic acid, and is also an important anionic surfactant. Alkylbenzene sulfonate mainly includes linear alkylbenzene sulfonate (LAS) and branched alkylbenzene sulfonate (ABS).

[0003] Due to poor biodegradability, branched alkylbenzene sulfonates have been gradually replaced by linear alkylbenzene sulfonates. Linear alkylbenzene sulfonates have strong detergency, good foaming ability and foam stability, and have good stability in acidic, alkaline and even oxidant solutions. In addition, they are abundant in source, mature in manufacturing process and low in cost. They are excellent detergents and foaming agents. As active substances in detergents, linear alkylbenzene sulfonates are easy to spray dry and form, and are very suitable for making washing powders. They can also be added to shampoos, foam baths and other bath liquids in appropriate amounts. They can also be used as cleaning agents, dyeing aids, and raw materials for metal cleaning and deinking agents in the papermaking industry.

[0004] However, linear alkylbenzene sulfonates also have some defects, such as being sensitive to water hardness, rapidly reducing washing ability in hard water, and easily reacting with calcium and magnesium ions in water to form organic deposits that remain on clothing. Organic deposits can reduce the performance of fabrics, such as increasing the hydrophobicity of fabrics, reducing capillary effects, reducing the climate regulation of clothing, and aggravating the retention of stains on fabrics. In addition, linear alkylbenzene sulfonates, as personal care raw materials, are more irritating than fatty alcohol sulfates and fatty alcohol polyoxyethylene ether sulfates, resulting in limited usage and scope of application.

[0005] Alkylphenol polyoxyethylene ether It is often used to replace linear alkylbenzene sulfonate. Alkylphenol polyoxyethylene ethers undergo initial biodegradation to obtain alkylphenols, which are also difficult to biodegrade. Although it has good emulsification, leveling, penetration and wetting effects, it also has the problem of being difficult to biodegrade. Summary of the invention

[0006] Based on this, it is necessary to provide an alkyl ether polyoxyethylene ether benzene sulfonic acid to address the above problems, which has the advantages of being biodegradable, having strong resistance to hard water and low irritation.

[0007] An alkyl ether polyoxyethylene ether benzene sulfonic acid having a structure as shown in Formula I:

[0008]

[0009] Wherein, R is a C8-C16 straight chain alkyl or branched chain alkyl, and n is selected from 1 to 3.

[0010] The above-mentioned alkyl ether polyoxyethylene ether benzene sulfonic acid has good biodegradability and resistance to hard water, and has low irritation as a surfactant; the alkyl ether polyoxyethylene ether benzene sulfonic acid is different from the existing alkylbenzene sulfonic acid and alkylphenol polyoxyethylene ether, and has no alkyl substituent on its benzene ring, so that it has good surface activity and permeability, and is expected to replace the application of alkylphenol polyoxyethylene ether in industrial detergents.

[0011] The present invention also provides a method for preparing the above-mentioned alkyl ether polyoxyethylene ether benzene sulfonic acid, which is synthesized via the route shown in Formula II:

[0012]

[0013] S1, using fatty alcohol polyoxyethylene ether and phenol as reactants, adding a catalyst, and reacting to obtain phenyl alkyl ether polyoxyethylene ether;

[0014] S2. Using phenyl alkyl ether polyoxyethylene ether and sulfur trioxide as reactants, a reaction is performed to obtain an alkyl ether polyoxyethylene ether benzene sulfonic acid as shown in formula I.

[0015] In one embodiment, the catalyst in S1 is a MgO-supported metal-based catalyst, the supported metal is selected from: one or more of zinc, nickel, and titanium, and the supported amount of the metal is 3-8% of the weight of MgO.

[0016] In one embodiment, the loaded metals are two of zinc, nickel and titanium, and the mass ratio of the two metals is 1:(0.33-3).

[0017] In one embodiment, the reaction temperature in S1 is 200-300°C, and the pressure is 1.0-2.0 MPa. Preferably, the reaction temperature in S1 is 220-280°C, and the pressure is 1.2-1.5 MPa.

[0018] In one embodiment, the molar ratio of fatty alcohol polyoxyethylene ether to phenol is 1:(0.5-5). Preferably, the molar ratio of fatty alcohol polyoxyethylene ether to phenol is 1:(0.6-1.5)

[0019] In one embodiment, S2 is specifically as follows: reacting in a sulfonation reactor, mixing phenyl alkyl ether polyoxyethylene ether and sulfur trioxide-air mixed gas, the concentration of sulfur trioxide in the sulfur trioxide-air mixed gas is 4-6vt%, the amount of substance ratio of phenyl alkyl ether polyoxyethylene ether to sulfur trioxide is (1.02-1.04):1, the inlet temperature of the sulfur trioxide-air mixed gas is 48-58°C, and the sulfonation reactor is cooled by circulating cooling water so that the gas temperature at the outlet of the sulfonation reactor is 43-48°C.

[0020] In one embodiment, the temperature of the circulating cooling water is 26-30°C.

[0021] The present invention also provides an alkyl ether polyoxyethylene ether benzene sulfonate having a structure as shown in Formula III:

[0022]

[0023] Wherein, R is a C8-C16 straight chain alkyl or branched chain alkyl, n is selected from 1 to 3, and M is selected from: Na + , K + NH4 + 、C2H7NOH + 、C4H 11 NO2H + 、C6H 15 NO3H + 、C3H9ONH + .

[0024] Although the structure of the above-mentioned alkyl ether polyoxyethylene ether benzene sulfonate is similar to that of alkylphenol polyoxyethylene ether sulfate, it not only has a good emulsifying effect, but also does not produce alkylphenol after degradation, and its biodegradability is equivalent to that of conventional linear alkylbenzene sodium sulfonate.

[0025] The present invention also provides a method for preparing the alkylbenzene sulfonate, which uses an alkaline solution and the alkyl ether polyoxyethylene ether benzene sulfonic acid of the present invention as raw materials, and undergoes a neutralization reaction to obtain the alkylbenzene sulfonate.

[0026] In one embodiment, the alkaline solution is selected from: sodium hydroxide solution, potassium hydroxide solution, ammonia water, alcohol ammonia. In one embodiment, the alcohol amine is selected from: monoethanolamine, diethanolamine, triethanolamine, isopropanolamine.

[0027] The present invention also provides an application of the alkyl ether polyoxyethylene ether benzene sulfonic acid or the alkyl ether polyoxyethylene ether benzene sulfonate in the preparation of detergents.

[0028] Compared with the prior art, the present invention has the following beneficial effects:

[0029] The alkyl ether polyoxyethylene ether benzene sulfonic acid of the present invention has the advantages of being biodegradable, having strong resistance to hard water and low irritation. The alkyl ether polyoxyethylene ether benzene sulfonate of the present invention not only has a good emulsifying effect, but also does not produce alkylphenol after degradation, and its biodegradability is comparable to that of conventional linear alkylbenzene sulfonate sodium. The alkyl ether polyoxyethylene ether benzene sulfonic acid and the alkyl ether polyoxyethylene ether benzene sulfonate of the present invention are used as surfactants to prepare personal cleaning and care products, which can improve the hard water resistance and biodegradability of the personal cleaning and care products, while reducing irritation. DETAILED DESCRIPTION

[0030] For ease of understanding of the present invention, the present invention will be described more fully below in conjunction with preferred embodiments. However, the present invention can be implemented in many different forms and is not limited to the embodiments described herein. On the contrary, the purpose of providing these embodiments is to make the understanding of the disclosure of the present invention more thorough and comprehensive.

[0031] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as those commonly understood by those skilled in the art of the present invention. The terms used in the specification of the present invention herein are only for the purpose of describing specific embodiments and are not intended to limit the present invention.

[0032] Example 1

[0033] An alkyl ether polyoxyethylene ether benzene sulfonic acid, the structural formula of which is shown in Formula I, R is C 16 H 33 (2-methyl-pentadecanyl), n is 1. Its preparation method is as follows:

[0034] (1) Phenol and fatty alcohol polyoxyethylene ether are mixed in a molar ratio of 2:1, and a MgO-loaded metal-based catalyst (the loading amount is 3% of the weight of MgO, and the loaded metals are Zn and Ti, and the mass ratio of the two is 1:3) is added. After mixing evenly, the temperature is controlled to be 295-300°C and the pressure is 1.0-1.1 MPa. The reaction is carried out for 40-60 minutes to obtain phenyl alkyl ether polyoxyethylene ether. The conversion rate of fatty alcohol polyoxyethylene ether is 72% after testing.

[0035] (2) placing phenyl alkyl ether polyoxyethylene ether in a membrane sulfonation reactor, introducing a sulfur trioxide-air mixed gas, wherein the concentration of sulfur trioxide in the sulfur trioxide-air mixed gas is 5vt%, the molar ratio of phenyl alkyl ether polyoxyethylene ether to sulfur trioxide in the sulfonation reactor is 1:1, and the temperature of the sulfur trioxide-air mixed gas is 50°C. During the reaction, the sulfonation reactor is cooled by circulating cooling water so that the gas temperature at the outlet of the sulfonation reactor is 45°C. After the reaction is completed, alkyl ether polyoxyethylene ether benzene sulfonic acid is obtained after aging.

[0036] An alkyl ether polyoxyethylene ether benzene sulfonic acid isopropanolamine is prepared by using the alkyl ether polyoxyethylene ether benzene sulfonic acid of Example 1, specifically comprising the following steps: taking isopropanolamine and alkyl ether polyoxyethylene ether benzene sulfonic acid, the molar ratio of isopropanolamine to alkyl ether polyoxyethylene ether benzene sulfonic acid is 1:1, adding alkyl ether polyoxyethylene ether benzene sulfonic acid to isopropanolamine while stirring, and after the neutralization reaction is completed, alkyl ether polyoxyethylene ether benzene sulfonic acid isopropanolamine is obtained. The reaction formula is as follows.

[0037]

[0038] Example 2

[0039] An alkyl ether polyoxyethylene ether benzene sulfonic acid, the structural formula of which is shown in Formula I, R is C 10 H 21 Straight-chain alkyl, n is 2. The preparation method is basically the same as that of Example 1, except that step (1): phenol and fatty alcohol polyoxyethylene ether are mixed at a molar ratio of 1:2, MgO-loaded metal-based catalyst (loaded amount is 8% of the weight of MgO, and the loaded metals are Zn and Ni, and the mass ratio of the two is 3:1) with a mass ratio of 6% of the mass of phenol is added, and after mixing evenly, the temperature is controlled to be 200-205°C, the pressure is 1.9-2.0Mpa, and the reaction is carried out for 50-70min to obtain phenyl alkyl ether polyoxyethylene ether, and the conversion rate of fatty alcohol polyoxyethylene ether is 71% after testing.

[0040] A potassium alkyl ether polyoxyethylene ether benzene sulfonate is prepared by using the alkyl ether polyoxyethylene ether benzene sulfonic acid of Example 2, specifically comprising the following steps: taking a potassium hydroxide solution (mass concentration 15%) and the alkyl ether polyoxyethylene ether benzene sulfonic acid of Example 2, the molar ratio of potassium hydroxide to the alkyl ether polyoxyethylene ether benzene sulfonic acid being 1:1, adding the alkyl ether polyoxyethylene ether benzene sulfonic acid to the potassium hydroxide solution while stirring, and after the neutralization reaction is completed, the potassium alkyl ether polyoxyethylene ether benzene sulfonate is obtained. The reaction formula is as follows.

[0041]

[0042] Example 3

[0043] An alkyl ether polyoxyethylene ether benzene sulfonic acid, the structural formula of which is shown in Formula I, R is C8H 17Straight-chain alkyl, n is 3. The preparation method is basically the same as that of Example 1, except that step (1): phenol and fatty alcohol polyoxyethylene ether are mixed at a molar ratio of 1.5:1, MgO-loaded metal-based catalyst (loaded amount is 8% of the weight of MgO, and the loaded metals are Zn and Ti, and the mass ratio of the two is 1:2) with a mass ratio of 4% of the mass of phenol is added, and after mixing evenly, the temperature is controlled to be 275-280°C, the pressure is 1.2-1.3Mpa, and the reaction is carried out for 45-65min to obtain phenyl alkyl ether polyoxyethylene ether, and the conversion rate of fatty alcohol polyoxyethylene ether is 84% ​​after detection.

[0044] A sodium alkyl ether polyoxyethylene ether benzene sulfonate is prepared by using the alkyl ether polyoxyethylene ether benzene sulfonic acid of Example 3, specifically comprising the following steps: taking a sodium hydroxide solution (mass concentration 15%) and an alkyl ether polyoxyethylene ether benzene sulfonic acid, wherein the molar ratio of the sodium hydroxide to the alkyl ether polyoxyethylene ether benzene sulfonic acid is 1:1, adding the alkyl ether polyoxyethylene ether benzene sulfonic acid to the sodium hydroxide solution while stirring, and after the neutralization reaction is completed, obtaining the sodium alkyl ether polyoxyethylene ether benzene sulfonate. The reaction formula is as follows.

[0045]

[0046] Example 4

[0047] An alkyl ether polyoxyethylene ether benzene sulfonic acid, the structural formula of which is shown in Formula I, R is C 14 H 29 Straight-chain alkyl, n is 2. The preparation method is basically the same as that of Example 1, except that step (1): phenol and fatty alcohol polyoxyethylene ether are mixed at a molar ratio of 1:1.5, MgO-loaded metal-based catalyst (loaded amount is 6% of the weight of MgO, and the loaded metals are Zn and Ti, and the mass ratio of the two is 2:1) with a mass ratio of 5% of the mass of phenol is added, and after mixing evenly, the temperature is controlled to be 220-225°C, the pressure is 1.4-1.5Mpa, and the reaction is carried out for 40-60min to obtain phenyl alkyl ether polyoxyethylene ether, and the conversion rate of fatty alcohol polyoxyethylene ether is 87% after detection.

[0048] An alkyl ether polyoxyethylene ether benzene sulfonic acid monoethanolamine is prepared by using the alkyl ether polyoxyethylene ether benzene sulfonic acid of Example 4, and specifically comprises the following steps: taking monoethanolamine and alkyl ether polyoxyethylene ether benzene sulfonic acid, wherein the molar ratio of monoethanolamine to alkyl ether polyoxyethylene ether benzene sulfonic acid is 1:1, adding alkyl ether polyoxyethylene ether benzene sulfonic acid to monoethanolamine while stirring, and after the neutralization reaction is completed, obtaining alkyl ether polyoxyethylene ether benzene sulfonic acid monoethanolamine. The reaction formula is as follows.

[0049]

[0050] Example 5

[0051] An alkyl ether polyoxyethylene ether benzene sulfonic acid, the structural formula of which is different from that of Example 1 in that n is 2. The preparation method thereof is substantially the same as that of Example 1, except that step (1) comprises mixing phenol and fatty alcohol polyoxyethylene ether in a molar ratio of 1:1, adding MgO-supported metal-based catalyst (the supported amount is 5% of the weight of MgO, and the supported metals are Ti and Ni, and the mass ratio of the supported metals is 1:1) with a content of 4.2% of the mass of phenol, and after uniform mixing, controlling the temperature to 260-265°C, the pressure to 1.3-1.4 MPa, and reacting for 50-70 minutes to obtain benzene alkyl ether polyoxyethylene ether, and detecting that the conversion rate of fatty alcohol polyoxyethylene ether is 86%.

[0052] Example 6

[0053] An alkyl ether polyoxyethylene ether benzene sulfonic acid, the structural formula of which is shown in Formula I, R is C 12 H 25 Straight-chain alkyl, n is 3. The preparation method is basically the same as that of Example 1, except that step (1): phenol and fatty alcohol polyoxyethylene ether are mixed at a molar ratio of 1.2:1, MgO-loaded metal-based catalyst (loaded amount is 4.5% of the weight of MgO, and the loaded metals are Zn and Ti, and the mass ratio of the two is 3:4) with a mass ratio of 4.5% of the mass of phenol is added, and after mixing evenly, the temperature is controlled to be 250-255°C, the pressure is 1.25-1.35Mpa, and the reaction is carried out for 45-65min to obtain phenyl alkyl ether polyoxyethylene ether, and the conversion rate of fatty alcohol polyoxyethylene ether is 83% after detection.

[0054] An alkyl ether polyoxyethylene ether benzene sulfonic acid diethanolamine is prepared by using the alkyl ether polyoxyethylene ether benzene sulfonic acid of Example 6, and specifically comprises the following steps: taking diethanolamine and alkyl ether polyoxyethylene ether benzene sulfonic acid, the molar ratio of monoethanolamine to alkyl ether polyoxyethylene ether benzene sulfonic acid is 1:1, adding alkyl ether polyoxyethylene ether benzene sulfonic acid to monoethanolamine while stirring, and after the neutralization reaction is completed, alkyl ether polyoxyethylene ether benzene sulfonic acid diethanolamine is obtained. The reaction formula is as follows.

[0055]

[0056] Example 7

[0057] An alkyl ether polyoxyethylene ether benzene sulfonic acid, whose structural formula is the same as that of Example 1. The preparation method thereof is substantially the same as that of Example 1, except that step (1) is to mix phenol and fatty alcohol polyoxyethylene ether in a molar ratio of 4:5, add MgO-loaded metal-based catalyst (loaded amount is 5.5% of the weight of MgO, and the loaded metals are Zn and Ni, and the mass ratio of the two is 3:2) with a mass ratio of 4.8% of the mass of phenol, and after uniform mixing, control the temperature to 230-235°C, the pressure to 1.3-1.5Mpa, react for 55-75min, and obtain phenyl alkyl ether polyoxyethylene ether, and the conversion rate of fatty alcohol polyoxyethylene ether is 82% after detection.

[0058] Example 8

[0059] An alkyl ether polyoxyethylene ether benzene sulfonic acid, the structural formula of which is different from that of Example 1 in that n is 3. The preparation method thereof is substantially the same as that of Example 1, except that step (1) comprises mixing phenol and fatty alcohol polyoxyethylene ether at a molar ratio of 1.8:1, adding MgO-supported metal-based catalyst (the supported amount is 7% of the weight of MgO, and the supported metals are Ti and Zn, and the mass ratio of the supported metals is 2:5) with a content of 3.5% of the mass of phenol, and after uniform mixing, controlling the temperature to 210-215°C, the pressure to 1.6-1.7 MPa, and reacting for 45-65 minutes to obtain phenyl alkyl ether polyoxyethylene ether, and detecting that the conversion rate of fatty alcohol polyoxyethylene ether is 70%.

[0060] Example 9

[0061] An alkyl ether polyoxyethylene ether benzene sulfonic acid, whose structural formula is the same as that of Example 1. The preparation method thereof is substantially the same as that of Example 1, except that step (1) is to mix phenol and fatty alcohol polyoxyethylene ether in a molar ratio of 3:5, add MgO-loaded metal-based catalyst (loaded amount is 3.5% of the weight of MgO, and loaded metals are Ni and Zn, and the mass ratio of the two is 2.5:1) with a mass ratio of 5.5% of the mass of phenol, and after uniform mixing, control the temperature to 285-287°C, the pressure to 1.7-1.8Mpa, react for 40-60min, and obtain phenyl alkyl ether polyoxyethylene ether, and the conversion rate of fatty alcohol polyoxyethylene ether is 75% after detection.

[0062] Embodiments 10 to 17

[0063] Examples 10 to 17 are all personal cleansers, and the raw material composition of each example and the mass fraction of each component are shown in Table 1.

[0064] The preparation method of the personal cleanser comprises the following steps:

[0065] (1) Mix a surfactant with an appropriate amount of water and stir until the surfactant is completely dissolved;

[0066] (2) Add moisturizer and stir until completely dissolved; skip this step if the formula does not contain moisturizer;

[0067] (3) Add citric acid to adjust the pH to 5.5-6.5;

[0068] (4) Add sodium chloride and stir until completely dissolved; skip this step if the formula does not contain sodium chloride;

[0069] (5) Ensure the temperature is below 45°C, add appropriate amount of flavor, stir evenly, and cool to room temperature.

[0070] Table 1 Raw materials and proportions of personal cleansers (wt%)

[0071]

[0072]

[0073] Note: the alkyl ether polyoxyethylene ether benzene sulfonate sodium, alkyl ether polyoxyethylene ether benzene sulfonate ammonium, alkyl ether polyoxyethylene ether benzene sulfonate isopropanolamine, alkyl ether polyoxyethylene ether benzene sulfonate monoethanolamine and alkyl ether polyoxyethylene ether benzene sulfonate triethanolamine in the table are all alkyl ether polyoxyethylene ether benzene sulfonates of the present invention.

[0074] Experimental Example 1

[0075] The alkyl ether polyoxyethylene ether benzene sulfonate of Example 1 and Example 3 was used as a surfactant to test its biodegradability, hard water resistance and irritation. At the same time, conventional linear sodium dodecylbenzene sulfonate, sodium alkylphenol polyoxyethylene ether sulfonate and sodium fatty alcohol polyoxyethylene ether sulfate were used as control groups.

[0076] Biodegradability is characterized by the total BOD value elimination rate (%). When the BOD value is above 50%, it can be considered that the tested substance has basically achieved complete biodegradation.

[0077] Resistance to hard water is characterized by the foaming ability of surfactants in hard water. The test is carried out in accordance with Chapter 11 of GB / T 13173-2021. The surfactant concentration is 0.375g / L, the water hardness is 400ppm, and the water temperature is (40±0.5)℃.

[0078] The irritation test of surfactants uses the corn alcohol-soluble protein (Zein) method. Zein is a yellow corn protein that is almost insoluble in water. Its structure is similar to keratin found in skin and hair. Zein reacts with irritating substances, such as surfactant solutions, to denature and dissolve. Stronger irritating surfactants are more likely to cause Zein to denature than weaker irritating surfactants, which increases the dissolution of Zein. The amount of Zein dissolved represents the skin irritation of the surfactant or formulation. Take the sample to be tested and prepare a solution with a mass fraction of 1% of the active substance. Take 100g of the solution, add 0.5g of Zein gradually until it cannot be dissolved, stir for 2 hours, and then filter. Dry the filter paper and precipitate in a 45°C oven overnight, weigh, and calculate the amount of dissolved Zein. The greater the amount of dissolved Zein, the greater the irritation.

[0079] The test results are shown in the following table:

[0080] Table 2 Performance test results

[0081]

[0082] It can be seen from the above results that the alkyl ether polyoxyethylene ether benzene sulfonate of the present invention has good biodegradability, strong hard water resistance and low irritation.

[0083] The technical features of the above-described embodiments may be arbitrarily combined. To make the description concise, not all possible combinations of the technical features in the above-described embodiments are described. However, as long as there is no contradiction in the combination of these technical features, they should be considered to be within the scope of this specification.

[0084] The above-mentioned embodiments only express several implementation methods of the present invention, and the descriptions thereof are relatively specific and detailed, but they cannot be understood as limiting the scope of the invention patent. It should be pointed out that, for ordinary technicians in this field, several variations and improvements can be made without departing from the concept of the present invention, and these all belong to the protection scope of the present invention. Therefore, the protection scope of the patent of the present invention shall be subject to the attached claims.

Claims

1. An alkyl ether polyoxyethylene ether benzene sulfonic acid, characterized in that: Having the structure shown in Formula I: Wherein, R is a C8-C16 straight chain alkyl or branched chain alkyl, and n is selected from 1 to 3; The alkyl ether polyoxyethylene ether benzene sulfonic acid is synthesized via the route shown in Formula II: S1, using fatty alcohol polyoxyethylene ether and phenol as reactants, adding a catalyst, and reacting to obtain phenyl alkyl ether polyoxyethylene ether; S2, using phenyl alkyl ether polyoxyethylene ether and sulfur trioxide as reactants to obtain an alkylbenzene sulfonic acid as shown in Formula I; the catalyst in S1 is a MgO-supported metal-based catalyst, the supported metal is selected from: one or more of zinc, nickel, and titanium, and the supported amount of the metal is 3-8% of the weight of MgO; In S1, the reaction temperature is 200-300° C., the pressure is 1.0-2.0 MPa, and the molar ratio of fatty alcohol polyoxyethylene ether to phenol is 1:(0.5-5).

2. The alkyl ether polyoxyethylene ether benzene sulfonic acid according to claim 1, characterized in that In S1, the reaction temperature is 220-280° C., the pressure is 1.2-1.5 MPa, and the molar ratio of fatty alcohol polyoxyethylene ether to phenol is 1:(0.6-1.5).

3. The alkyl ether polyoxyethylene ether benzene sulfonic acid according to claim 1, characterized in that The S2 is specifically as follows: reacting in a sulfonation reactor, mixing phenyl alkyl ether polyoxyethylene ether and sulfur trioxide-air mixed gas, wherein the concentration of sulfur trioxide in the sulfur trioxide-air mixed gas is 4-6vt%, the amount of substance ratio of phenyl alkyl ether polyoxyethylene ether to sulfur trioxide is (1.02-1.04):1, the inlet temperature of the sulfur trioxide-air mixed gas is 48-58°C, and the sulfonation reactor is cooled by circulating cooling water so that the gas temperature at the outlet of the sulfonation reactor is 43-48°C.

4. An alkyl ether polyoxyethylene ether benzene sulfonate, characterized in that: Having the structure shown in Formula III: Wherein, R is a C8-C16 straight chain alkyl or branched chain alkyl, n is selected from 1 to 3, and M is selected from: Na + , K + NH4 + , The preparation method of the alkyl ether polyoxyethylene ether benzene sulfonate is as follows: using an alkaline solution and the alkyl ether polyoxyethylene ether benzene sulfonic acid according to claim 1 as raw materials, and obtaining the alkyl benzene sulfonate through a neutralization reaction.

5. The alkyl ether polyoxyethylene ether benzene sulfonate according to claim 4, characterized in that: The alkaline solution is selected from: sodium hydroxide solution, potassium hydroxide solution, ammonia water, and alcohol amine solution.

6. Use of the alkyl ether polyoxyethylene ether benzene sulfonic acid according to claim 1 or the alkyl ether polyoxyethylene ether benzene sulfonate according to claim 4 in the preparation of personal cleaning and care products.

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