Preparation method of bio-based amination modified fatty alcohol polyoxyethylene ether sulfate

Abstract

The invention belongs to the technical field of polyether polyol preparation, and particularly relates to a preparation method of bio-based amination modified fatty alcohol polyoxyethylene ether sulfate. In order to solve the problem that fatty alcohol-polyoxyethylene ether sulfate prepared in the prior art is poor in foam increasing and thickening performance, the invention provides a preparation method of bio-based amination modified fatty alcohol-polyoxyethylene ether sulfate. The method comprises the following steps: reacting bio-based grease with alkylene oxide under the action of an amine catalyst to prepare modified vegetable oil polyether, and then carrying out polymerization reaction on the modified vegetable oil polyether and fatty alcohol with alkylene oxide under the action of a double metal cyanide complex catalyst to obtain bio-based aminated modified fatty alcohol-polyoxyethylene ether. Finally, the bio-based amination modified fatty alcohol-polyoxyethylene ether reacts with sulfates to prepare bio-based amination modified fatty alcohol-polyoxyethylene ether sulfate, and the obtained bio-based amination modified fatty alcohol-polyoxyethylene ether sulfate has good foam increasing and thickening performance.

Description

Technical Field

[0001] This application belongs to the field of polyether polyol preparation technology, and specifically relates to a method for preparing bio-based amination-modified fatty alcohol polyoxyethylene ether sulfate. Background Technology

[0002] Surfactants, as an important component of the chemical industry, are widely used in various fields such as daily chemical products, textiles, agriculture, and medicine. Due to their ability to significantly reduce the surface tension or interfacial tension of liquids, surfactants play a crucial role in cleaning, emulsification, and dispersion.

[0003] Hybrid surfactants are a special class of surfactants whose molecular structures contain both polyoxyethylene chains and ionic groups. This structure endows them with the properties of both nonionic and anionic surfactants. Nonionic surfactants are known for their excellent solubility and resistance to hard water, while anionic surfactants excel in detergency and foam stability. Fatty alcohol polyoxyethylene ether sulfate (AES) is the most important and widely produced type of hybrid surfactant, combining the advantages of both types and exhibiting excellent solubility, resistance to hard water, and wetting properties.

[0004] However, despite its excellent performance in many aspects, AES still has some limitations in certain specific applications. AES has relatively poor foaming and solution thickening abilities, which limits its application in areas requiring high foam stability and high viscosity, such as personal care products like shampoos and shower gels, and certain industrial cleaning agents. Furthermore, the biodegradability of AES needs improvement, especially its slow degradation rate in natural water bodies, which may have long-term environmental impacts. Summary of the Invention

[0005] This application aims to address the problem of poor foaming and thickening properties of fatty alcohol polyoxyethylene ether sulfates prepared by existing technologies. This application provides a method for preparing bio-based amination-modified fatty alcohol polyoxyethylene ether sulfates. The method involves reacting bio-based oils with epoxides under the action of an amine catalyst to obtain modified vegetable oil polyethers. Then, the modified vegetable oil polyethers and fatty alcohols are polymerized with epoxides under the action of a bimetallic cyanide complexing catalyst to obtain bio-based amination-modified fatty alcohol polyoxyethylene ethers. Finally, the bio-based amination-modified fatty alcohol polyoxyethylene ethers are reacted with sulfates to prepare bio-based amination-modified fatty alcohol polyoxyethylene ether sulfates. The resulting bio-based amination-modified fatty alcohol polyoxyethylene ether sulfates exhibit good foaming and thickening properties.

[0006] This application provides a method for preparing bio-based amination-modified fatty alcohol polyoxyethylene ether sulfate, comprising the following steps: S1. Add vegetable oil and amine catalyst to the reactor, replace with nitrogen, and then introduce epoxide alkane into the reactor for polymerization. Control the reaction temperature at 90-150℃ and the pressure at -0.08-0.30MPa. After the reaction is complete, mature until there is no pressure drop in the reactor, remove unreacted monomers, and refine and process to obtain amine-modified vegetable oil polyether polyol. Adjust its pH to 5-7 and set aside for use. S2. Add a bimetallic cyanide complexing catalyst, acid, the amine-modified vegetable oil polyether polyol obtained in step S1, and fatty alcohol to the reactor. After nitrogen purging, heat and vacuum dehydrate until the water content is ≤0.02%. After dehydration, propylene oxide is introduced into the reactor for pre-drop reaction. After the pre-drop reaction is completed, the remaining epoxy alkane is introduced. The temperature is controlled at 90-150℃ and the pressure is -0.08-0.30MPa. Continue the internal pressure reaction. After the reaction is completed, mature until there is no pressure drop in the reactor. Remove unreacted monomers to obtain bio-based amine-modified fatty alcohol polyoxyethylene ether. S3. Mix the bio-based amination-modified fatty alcohol polyoxyethylene ether obtained in step S2, heat to 30-80℃ and stir, slowly add chlorosulfonic acid, react for 0.5-5h to obtain bio-based amination-modified fatty alcohol polyoxyethylene ether sulfate, add alkali solution at 30-50℃, react for 0.5-2h, dehydrate under reduced pressure, wash with ethanol, filter and dry to obtain bio-based amination-modified fatty alcohol polyoxyethylene ether sulfate.

[0007] Furthermore, the vegetable oil mentioned in step S1 is one or more of corn oil, palm oil, peanut oil, olive oil, cottonseed oil, castor oil, soybean oil, and rapeseed oil, and the mass ratio of the vegetable oil to the epoxide is 1:1 to 1:5.

[0008] Furthermore, the amine catalyst mentioned in step S1 is one or more of dimethylamine, ethylenediamine, trimethylamine, and dimethylethanolamine, and the amount of the amine catalyst used is 0.2%-0.5% of the sum of the mass of vegetable oil and epoxide hydrocarbons in step S1.

[0009] Furthermore, the epoxy alkane mentioned in step S1 is a random polymer of one or more of propylene oxide, ethylene oxide, epichlorohydrin, and butane.

[0010] Furthermore, the acid added in step S2 is phosphoric acid or sulfuric acid with a mass concentration of 50%, and the amount added is 5-8 ppm of the sum of the mass of the fatty alcohol and the amino-modified vegetable oil polyether polyol obtained in step S1. The amount of the bimetallic cyanide complex catalyst added is 20-60 ppm of the total mass of the reaction raw materials.

[0011] Furthermore, the fatty alcohol in step S2 is one or more of the C8-C22 fatty alcohols.

[0012] Furthermore, in step S2, the mass ratio of fatty alcohol to the amine-modified vegetable oil polyether polyol obtained in step S1 is 5:1-25.

[0013] Furthermore, the epoxide in step S2 is a mixture of ethylene oxide and other epoxy compounds, wherein the other epoxy compounds are one of propylene oxide, epichlorohydrin, or butane, and the mass ratio of ethylene oxide to other epoxy compounds is 95:5 to 5:95.

[0014] Furthermore, the hydroxyl value of the amine-modified vegetable oil polyether polyol obtained in step S1 is 50-200 mg KOH / g; the hydroxyl value of the bio-based amine-modified fatty alcohol polyoxyethylene ether obtained in step S2 is 20-300 mg KOH / g.

[0015] Furthermore, in step S3, the molar ratio of bio-based amination-modified fatty alcohol polyoxyethylene ether to chlorosulfonic acid is 1:0.5-1:3.

[0016] In step S1 of this application, long-chain fatty acid esters of vegetable oil undergo ring-opening polymerization with epoxides under the action of an amine catalyst to generate amine-modified vegetable oil polyether polyols. During the reaction, the epoxy groups of the epoxides open and react with the fatty acid ester groups in the vegetable oil to form polyoxyethylene chains. Using vegetable oil as a raw material increases the bio-based component of the surfactant, making it more environmentally friendly and sustainable. The amine-modified vegetable oil polyether polyol has good hydrophilicity and reactivity, and can further react with other compounds to increase the functionality of the surfactant. In step S2, fatty alcohols and amine-modified vegetable oil polyether polyols undergo copolymerization with epoxides under the action of a bimetallic cyanide complex catalyst to generate bio-based amine-modified fatty alcohol polyoxyethylene ethers. The bimetallic cyanide complex catalyst has high catalytic activity and can significantly improve the reaction rate and conversion rate. Bio-based amine-modified fatty alcohol polyoxyethylene ethers combine the characteristics of nonionic and anionic surfactants and are suitable for various applications.

[0017] Step S3 involves adding chlorosulfonic acid to the bio-based amination-modified fatty alcohol polyoxyethylene ether to produce a sulfonation reaction, thereby generating a bio-based amination-modified fatty alcohol polyoxyethylene ether sulfate. The sulfonation reaction introduces sulfate ions, giving the product stronger anionic properties, which significantly improves its foaming and thickening properties. The introduction of sulfate ions also increases the product's water solubility and dispersibility, making it more stable in aqueous solutions. Detailed Implementation

[0018] Example 1 S1. Add 500g castor oil and 3.91g ethylenediamine to a reaction vessel at room temperature and stir until homogeneous. After nitrogen purging, heat to 100℃ and add 1455g propylene oxide. Control the reaction temperature at 100℃ and the reaction pressure at 0.1MPa. After the reaction is complete, mature for 3 hours until there is no pressure drop. Remove monomers for 1 hour, cool and discharge to obtain amine-modified vegetable oil polyether polyol. Add phosphoric acid to adjust the pH to 5.74. The hydroxyl value is tested to be 55.1mgKOH / g.

[0019] S2. Add 500g of the amino-modified vegetable oil polyether polyol obtained in step S1, 200g of C8 fatty alcohol, 0.05g of bimetallic cyanide complexing catalyst, and 0.002g of 50% phosphoric acid to a reactor. Heat to 120℃ to dehydrate until the moisture content is less than 0.02%. Add 50g of propylene oxide for pre-drop reaction. After the pressure drops to negative pressure, add 200g of propylene oxide and 750g of ethylene oxide. The reaction temperature is 140℃, and the mixture is matured for 2 hours. Cool down and discharge to obtain bio-based amino-modified fatty alcohol polyoxyethylene ether. The hydroxyl value is tested to be 65.2mgKOH / g.

[0020] S3. Add 200g of the bio-based amination-modified fatty alcohol polyoxyethylene ether obtained in step S2 into a three-necked flask, heat to 40℃, add 12.9g of chlorosulfonic acid dropwise, react for 1h, add 5g of 4wt% NaOH solution according to the neutralization value, react at 40℃ for 1h, heat to 100℃ and dehydrate under reduced pressure, then dissolve in ethanol to remove inorganic salts, filter and dry to obtain bio-based amination-modified fatty alcohol polyoxyethylene ether sulfate.

[0021] Example 2 S1. Add 500g of palm oil and 6g of dimethylamine to a reaction vessel at room temperature and stir until homogeneous. After nitrogen purging, heat to 110℃ and add 800g of propylene oxide and 200g of ethylene oxide. Control the reaction temperature at 110℃ and the reaction pressure at 0.1MPa. After the reaction is complete, mature for 4 hours until there is no pressure drop. Remove monomers for 1 hour, cool and discharge to obtain amine-modified vegetable oil polyether polyol. Add phosphoric acid to adjust the pH to 6.12. The hydroxyl value is tested to be 86.0mgKOH / g.

[0022] S2. Add 500g of the amine-modified vegetable oil polyether polyol obtained in step S1, 500g of C16 fatty alcohol, 0.05g of bimetallic cyanide complexing catalyst, and 0.002g of 50% phosphoric acid to a reactor. Heat to 130℃ to dehydrate until the moisture content is less than 0.02%. Add 50g of propylene oxide for pre-drop reaction. After the pressure drops, add 300g of propylene oxide and 650g of ethylene oxide. The reaction temperature is 130℃, and the mixture is matured for 2 hours. Cool down and discharge to obtain bio-based amine-modified fatty alcohol polyoxyethylene ether. The hydroxyl value is tested to be 74.9mgKOH / g.

[0023] S3. Add 200g of the bio-based amination-modified fatty alcohol polyoxyethylene ether obtained in step S2 into a three-necked flask, heat to 30℃, add 16.4g of chlorosulfonic acid dropwise, react for 1.5h, add 6.45g of 4wt% NaOH solution according to the neutralization value, react at 30℃ for 1.5h, heat to 100℃ and dehydrate under reduced pressure, then dissolve in ethanol to remove inorganic salts, filter and dry to obtain bio-based amination-modified fatty alcohol polyoxyethylene ether sulfate.

[0024] Example 3 S1. Add 200g palm oil, 200g castor oil, and 6g ethylenediamine to a reaction vessel at room temperature and stir until homogeneous. After nitrogen purging, heat to 120℃ and add 800g ethylene oxide. Control the reaction temperature at 120℃ and the reaction pressure at 0.2MPa. After the reaction is complete, mature for 5 hours until there is no pressure drop. Remove monomers for 1 hour, cool down and discharge to obtain amine-modified vegetable oil polyether polyol. Add phosphoric acid to adjust the pH to 5.92. The hydroxyl value is tested to be 135.9mgKOH / g.

[0025] S2. Add 500g of the amine-modified vegetable oil polyether polyol obtained in step S1, 100g of C22 fatty alcohol, 0.05g of bimetallic cyanide complexing catalyst, and 0.002g of 50% phosphoric acid to a reactor. Heat to 130℃ to dehydrate until the moisture content is less than 0.02%. Add 50g of propylene oxide for pre-drop reaction. After the pressure drops, add 100g of propylene oxide and 450g of ethylene oxide. The reaction temperature is 150℃, and the mixture is matured for 3 hours. Cool down and discharge to obtain bio-based amine-modified fatty alcohol polyoxyethylene ether. The hydroxyl value is tested to be 70.9mgKOH / g.

[0026] S3. Add 200g of the bio-based amination-modified fatty alcohol polyoxyethylene ether obtained in step S2 into a three-necked flask, heat to 50℃, add 12.2g of chlorosulfonic acid dropwise, react for 2h, add 4.58g of 4wt% NaOH solution according to the neutralization value, react at 50℃ for 2h, heat to 100℃ and dehydrate under reduced pressure, then dissolve in ethanol to remove inorganic salts, filter and dry to obtain bio-based amination-modified fatty alcohol polyoxyethylene ether sulfate.

[0027] Example 4 S1. Add 400g castor oil and 1.6g ethylenediamine to a reaction vessel at room temperature and stir until homogeneous. After nitrogen purging, heat to 120℃ and add 400g ethylene oxide. Control the reaction temperature at 120℃ and the reaction pressure at 0.2MPa. After the reaction is complete, mature for 5 hours until there is no pressure drop. Remove monomers for 1 hour, cool and discharge to obtain amine-modified vegetable oil polyether polyol. Add phosphoric acid to adjust the pH to 5.78, and test the hydroxyl value to be 100mgKOH / g.

[0028] S2. Add 500g of the amine-modified vegetable oil polyether polyol obtained in step S1, 100g of C22 fatty alcohol, 0.032g of bimetallic cyanide complexing catalyst, and 0.003g of 50% phosphoric acid to a reactor. Heat to 130℃ to dehydrate until the moisture content is less than 0.02%. Add 25g of propylene oxide for pre-drop reaction. After the pressure drops, add 25g of propylene oxide and 950g of ethylene oxide. The reaction temperature is 150℃, and the mixture is matured for 3 hours. Cool down and discharge to obtain bio-based amine-modified fatty alcohol polyoxyethylene ether. The hydroxyl value is tested to be 42mgKOH / g.

[0029] S3. Add 200g of the bio-based amination-modified fatty alcohol polyoxyethylene ether obtained in step S2 into a three-necked flask, heat to 50℃, add 12.2g of chlorosulfonic acid dropwise, react for 2h, add 4.58g of 4wt% NaOH solution according to the neutralization value, react at 50℃ for 2h, heat to 100℃ and dehydrate under reduced pressure, then dissolve in ethanol to remove inorganic salts, filter and dry to obtain bio-based amination-modified fatty alcohol polyoxyethylene ether sulfate.

[0030] Example 5 S1. Add 400g castor oil and 12g ethylenediamine to a reaction vessel at room temperature and stir until homogeneous. After nitrogen purging, heat to 120℃ and add 2000g ethylene oxide. Control the reaction temperature at 120℃ and the reaction pressure at 0.2MPa. After the reaction is complete, mature for 5 hours until there is no pressure drop. Remove monomers for 1 hour, cool and discharge to obtain amine-modified vegetable oil polyether polyol. Add phosphoric acid to adjust the pH to 5.92. The hydroxyl value is tested to be 40mgKOH / g.

[0031] S2. 100g of the amine-modified vegetable oil polyether polyol obtained in step S1, 500g of C22 fatty alcohol, 0.096g of bimetallic cyanide complexing catalyst, and 0.0048g of 50% phosphoric acid were added to a reactor. The mixture was heated to 130℃ to dehydrate until the moisture content was less than 0.02%. 50g of propylene oxide was added for pre-dropping reaction. After the pressure decreased, 900g of propylene oxide and 50g of ethylene oxide were added. The reaction temperature was 150℃, and the mixture was matured for 3 hours. The mixture was then cooled and discharged to obtain bio-based amine-modified fatty alcohol polyoxyethylene ether. The hydroxyl value was tested to be 56mgKOH / g.

[0032] S3. Add 200g of the bio-based amination-modified fatty alcohol polyoxyethylene ether obtained in step S2 into a three-necked flask, heat to 50℃, add 12.2g of chlorosulfonic acid dropwise, react for 2h, add 4.58g of 4wt% NaOH solution according to the neutralization value, react at 50℃ for 2h, heat to 100℃ and dehydrate under reduced pressure, then dissolve in ethanol to remove inorganic salts, filter and dry to obtain bio-based amination-modified fatty alcohol polyoxyethylene ether sulfate.

[0033] Example 6 S1. Add 500g of palm oil and 6g of dimethylamine to a reaction vessel at room temperature and stir until homogeneous. After nitrogen purging, heat to 110℃ and add 800g of propylene oxide and 200g of ethylene oxide. Control the reaction temperature at 110℃ and the reaction pressure at 0.1MPa. After the reaction is complete, mature for 4 hours until there is no pressure drop. Remove monomers for 1 hour, cool and discharge to obtain amine-modified vegetable oil polyether polyol. Add phosphoric acid to adjust the pH to 6.12. The hydroxyl value is tested to be 86.0mgKOH / g.

[0034] S2. 100g of the amine-modified vegetable oil polyether polyol obtained in step S1, 500g of C16 fatty alcohol, 0.05g of bimetallic cyanide complexing catalyst, and 0.002g of 50% phosphoric acid were added to a reactor. The mixture was heated to 130℃ to dehydrate until the moisture content was less than 0.02%. 50g of propylene oxide was added for pre-dropping reaction. After the pressure decreased, 300g of propylene oxide and 650g of ethylene oxide were added. The reaction temperature was 130℃, and the mixture was matured for 2 hours. The mixture was then cooled and discharged to obtain bio-based amine-modified fatty alcohol polyoxyethylene ether. The hydroxyl value was tested to be 25mgKOH / g.

[0035] S3. Add 200g of the bio-based amination-modified fatty alcohol polyoxyethylene ether obtained in step S2 into a three-necked flask, heat to 30℃, add 16.4g of chlorosulfonic acid dropwise, react for 1.5h, add 6.45g of 4wt% NaOH solution according to the neutralization value, react at 30℃ for 1.5h, heat to 100℃ and dehydrate under reduced pressure, then dissolve in ethanol to remove inorganic salts, filter and dry to obtain bio-based amination-modified fatty alcohol polyoxyethylene ether sulfate.

[0036] Comparative Example 1 used commercially available AEO-9 fatty alcohol polyoxyethylene ether for the experiment, and the other conditions were the same as in Example 1.

[0037] The product performance tests for each embodiment and comparative example are shown in the table below: Foam strength testing shall be performed according to the Roche foam tester method (GB / T7462—1994). The wetting experiment used the canvas settling method; The detergency was measured according to the washing test standard GB / T13174-2008; The emulsifying power was determined using the graduated cylinder method; To determine the viscosity effect, the obtained bio-based amination modified fatty alcohol polyoxyethylene ether and dodecylphenol benzenesulfonic acid were mixed evenly at a mass ratio of 4:3 at room temperature. 20% of the mass of the mixture was then added to hydrochloric acid with a concentration of 230 g / L, and the mixture was mixed evenly at room temperature. The viscosity was then measured.

Claims

1. A method for preparing bio-based aminated modified fatty alcohol polyoxyethylene ether sulfate, characterized in that: The following steps are involved: S1. Add vegetable oil and amine catalyst into a reactor, replace with nitrogen, then introduce alkylene oxide into the reactor for polymerization reaction, control the reaction temperature to 90-150° C., and the pressure to -0.08-0.30 MPa. After the reaction is completed, ripen until there is no pressure drop in the reactor, remove unreacted monomers, and refine and post-treat to obtain amino-modified vegetable oil polyether polyol, adjust the pH to 5-7, and set aside; S2, adding a double metal cyanide complex catalyst, an acid, the amino-modified vegetable oil polyether polyol obtained in step S1, and a fatty alcohol into a reactor, replacing with nitrogen, heating and vacuum dehydrating, introducing propylene oxide into the reactor for a pre-drop reaction, introducing the remaining alkylene oxide after the pre-drop reaction is completed, controlling the temperature to 90-150° C. and the pressure to -0.08-0.30 MPa, continuing the internal pressure reaction, and aging until there is no pressure drop in the reactor after the reaction is completed, removing unreacted monomers, and obtaining bio-based aminated modified fatty alcohol polyoxyethylene ether; S3. Mix the bio-based aminated modified fatty alcohol polyoxyethylene ethers obtained in step S2, heat to 30-80° C. and stir, slowly add chlorosulfonic acid, react for 0.5-5 h to obtain bio-based aminated modified fatty alcohol polyoxyethylene ether sulfate, add alkali solution at 30-50° C., react for 0.5-2 h, dehydrate under reduced pressure, then wash with ethanol, filter and dry to obtain bio-based aminated modified fatty alcohol polyoxyethylene ether sulfate.

2. The method for preparing the bio-based aminated modified fatty alcohol polyoxyethylene ether sulfate according to claim 1, characterized in that: The vegetable oil in step S1 is one or more of corn oil, palm oil, peanut oil, olive oil, cottonseed oil, castor oil, soybean oil and rapeseed oil, and the mass ratio of the vegetable oil to the alkylene oxide is 1:1-1:

5.

3. The method for preparing the bio-based aminated modified fatty alcohol polyoxyethylene ether sulfate according to claim 1, characterized in that: The amine catalyst in step S1 is one or more of dimethylamine, ethylenediamine, trimethylamine and dimethylethanolamine, and the amount of the amine catalyst used is 0.2%-0.5% of the sum of the mass of the vegetable oil and the alkylene oxide in step S1.

4. The method for preparing the bio-based aminated modified fatty alcohol polyoxyethylene ether sulfate according to claim 1, characterized in that: The alkylene oxide in step S1 is a random polymer of one or more of propylene oxide, ethylene oxide, epichlorohydrin and butylene oxide.

5. The method for preparing the bio-based aminated modified fatty alcohol polyoxyethylene ether sulfate according to claim 1, characterized in that: The acid added in step S2 is phosphoric acid or sulfuric acid with a mass concentration of 50%, and the added amount is 5-8ppm of the total mass of the fatty alcohol and the amino-modified vegetable oil polyether polyol obtained in step S1. The added amount of the double metal cyanide complex catalyst is 20-60ppm of the total mass of the reaction raw materials.

6. The method for preparing the bio-based aminated modified fatty alcohol polyoxyethylene ether sulfate according to claim 1, characterized in that: The fatty alcohol in step S2 is one or more of C8-C22 fatty alcohols.

7. The method for preparing the bio-based aminated modified fatty alcohol polyoxyethylene ether sulfate according to claim 1, characterized in that: The mass ratio of the fatty alcohol in step S2 to the amino-modified vegetable oil polyether polyol obtained in step S1 is 1:5-5:

1.

8. The method for preparing the bio-based aminated modified fatty alcohol polyoxyethylene ether sulfate according to claim 1, characterized in that: In step S2, the alkylene oxide is a mixture of ethylene oxide and other epoxy compounds, wherein the other epoxy compounds are one of propylene oxide, epichlorohydrin or butylene oxide, and the mass ratio of ethylene oxide to other epoxy compounds is 95:5-5:

95.

9. The method for preparing the bio-based aminated modified fatty alcohol polyoxyethylene ether sulfate according to claim 1, characterized in that: The hydroxyl value of the amino-modified vegetable oil polyether polyol obtained in step S1 is 50-200 mgKOH / g; the hydroxyl value of the bio-based aminated modified fatty alcohol polyoxyethylene ether obtained in step S2 is 20-300 mgKOH / g.

10. The method for preparing the bio-based aminated modified fatty alcohol polyoxyethylene ether sulfate according to claim 1, characterized in that: In step S3, the molar ratio of the bio-based aminated modified fatty alcohol polyoxyethylene ether to chlorosulfonic acid is 1:0.5-1:3.

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