CN106633090B - Oligomeric sulfosuccinate surfactants and methods of making the same - Google Patents

Oligomeric sulfosuccinate surfactants and methods of making the same Download PDF

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CN106633090B
CN106633090B CN201610866585.4A CN201610866585A CN106633090B CN 106633090 B CN106633090 B CN 106633090B CN 201610866585 A CN201610866585 A CN 201610866585A CN 106633090 B CN106633090 B CN 106633090B
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张楠
王杨
张城
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Beijing Huayi Science & Trade Co ltd
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Abstract

An oligomeric sulfosuccinate surfactant of formula I or formula II, wherein
Figure DDA0002457455780000011
R1Is C2～C22A straight or branched chain saturated hydrocarbon group; r2、R3、R4Are respectively C2～C22Straight-chain or branched saturated hydrocarbon radicals, R3、R4The same or different; r7、R8Is H or C1～C18A straight or branched chain saturated hydrocarbon group; the intermediate linking group of the molecule in the formula I is a condensation polymerization product of dibasic acid (or anhydride) and dihydric alcohol; n is 5-50, a is 2-100, and b is 0-100, which are integers; the product obtained by mono-esterifying secondary amine ether and maleic anhydride is used as two ends of the formula I; m1Is selected from L i+、Na+、K+、NH4 +One or more of them. The invention adjusts the performance of the finally obtained surfactant according to the difference of the molecular weight of the intermediate connecting group and the block structure.

Description

Oligomeric sulfosuccinate surfactants and methods of making the same
Technical Field
The invention relates to an oligomeric sulfosuccinate surfactant and a preparation method thereof, belonging to the field of gemini surfactants.
Background
The Gemini surfactant molecule contains two or more than two hydrophilic groups and hydrophobic groups, and is connected into a novel surfactant by an intermediate connecting group (Spacer) in a chemical bond mode. Compared with conventional surfactants, Gemini surfactants generally have the following characteristics:
gemini surfactants aggregate more readily into micelles, i.e., have relatively low CMC values, and are more suitable for use as emulsifiers and dispersants. The two ion head groups connected through chemical bonds in molecules are connected tightly, so that the hydrophobic groups have stronger interaction, the separation effect caused by electrostatic repulsion between the hydrophilic ion head groups is inhibited, and the combination between the hydrophobic groups is enhanced.
Gemini surfactants are more readily adsorbed and tightly aligned at the gas/liquid interface, are effective at reducing surface tension, and are generally good wetting agents.
There is a greater likelihood of synergy between the Gemini surfactant and other surfactants. Ionic Gemini surfactants have ionic head groups that are twice as charged, allowing small solid particles to be stably dispersed and suspended in water, and potentially stronger interactions with other types of surfactants (since the synergy of one surfactant with the other depends largely on the strength of the interaction between the hydrophilic groups of the two surfactants).
In addition to the interaction between ionic groups that contributes to some of the properties of Gemini surfactants, their intermediate linking groups (spacers), as shown in the following figures, also play a significant role:
Figure GDA0002483913350000011
as shown in the figure, the molecular chains of the three connecting groups have low flexibility to high flexibility, and even the Gemini surfactant synthesized by connecting the same ionic groups has great difference in surface activity. This is mainly due to the fact that conventional surfactants have hydrophobic groups that are flushed out of the liquid surface and hydrophilic groups that are in the liquid surface. The Gemini surfactant at least contains two polar groups, and in order to ensure that the minimum surface energy is obtained, the two polar groups can be arranged on the liquid surface according to the traditional surfactant, and the middle connecting group may need to be bent to ensure the arrangement of the polar groups. Therefore, by selecting molecular chains with different flexibilities, the novel Gemini surfactant with different surface activities can be synthesized.
The invention selects low polymer molecules with different flexibility and binary active groups as intermediate connecting groups in molecular design, takes a single-chain surfactant sulfosuccinate as one end of the synthesized surfactant, and is connected by the connecting groups through chemical bonds to form the novel amphiphilic surfactant. The surface activity of the novel surfactant has the advantages of high permeability, low foam, salt resistance and the like of the single-chain sulfosuccinate, and the novel surfactant has higher surface activity by virtue of the intermediate connecting group of the oligomer of the novel surfactant. Due to special structural expression, the surfactant with unique performance is synthesized according to the difference of the molecular weight or the block structure of the intermediate connecting group.
Disclosure of Invention
The invention aims to provide a multifunctional surfactant for a pressure-sensitive adhesive and a preparation method thereof.
In one aspect, the present invention provides oligomeric sulfosuccinate surfactants having the general formula shown in formula I and formula II:
Figure GDA0002483913350000021
wherein the content of the first and second substances,
Figure GDA0002483913350000022
R1is C2～C22A medium linear or branched saturated or unsaturated hydrocarbon group, wherein when R is1When the alkyl is unsaturated alkyl, the product obtained by conjugate addition of the alkyl and pyrosulfite is shown as formula III, wherein R is7,R8Is H or C1～C18A medium straight or branched chain saturated hydrocarbon group; r2,R3,R4,R5,R6Are respectively C2～C22A medium linear or branched saturated hydrocarbon group, wherein R3,R4,R5,R6The same or different; the intermediate connecting group of the molecule in the formula I is a condensation polymerization product of dibasic acid or anhydride and dihydric alcohol; n is 5 to 50, a is 0 to 100, b is 0 to 100, c is 0 to 100, and d is 0 to 100, which are integers; the products obtained by mono-esterifying secondary amine ether and maleic anhydride are used as two ends of the formula I;M1,M2are respectively selected from L i+,Na+,K+,NH4 +Wherein M is1,M2The same or different, and the same or different,
Figure GDA0002483913350000023
formula III.
Further, preferably, R is1Is C2～C4A medium linear or branched saturated or unsaturated hydrocarbon group, said R2Is C2～C4A medium straight or branched chain saturated hydrocarbon group, said R3Is C4～C13A medium straight or branched chain saturated hydrocarbon group, said R4Is C4～C13A medium straight or branched chain saturated hydrocarbon group, said R5Is C4～C13A medium straight or branched chain saturated hydrocarbon group, said R6Is C4～C13A medium straight or branched chain saturated hydrocarbon group; a is any integer of 2-50, b is any integer of 0-20, c is any integer of 0-20, and d is any integer of 2-50, because the products obtained under these conditions all show excellent hard water resistance and emulsifying capacity and the cutting fluid prepared from the same has long service life. Preferably, said R is1Is C4Said R is2Is C4Said R is3Is C4Said R is4Is C4Said R is5Is C4Said R is6Is C4A is 2, b is 10, c is 10, d is 2; preferably, said R is1Is C4Said R is2Is C2Said R is3Is C8Said R is4Is C8Said R is5Is C8Said R is6Is C8A is 5, b is 10, c is 10, d is 5; preferably, said R is1Is C2Said R is2Is C2Said R is3Is C12Said R is4Is C12Said R is5Is C12Said R is6Is C12A is 5, b is 0, c is 0, d is 5; preferably, said R is1Is C4Said R is2Is C2Said R is3Is C13Said R is4Is C13Said R is5Is C13Said R is6Is C13A is 50, b is 20, c is 20, d is 50.
In another aspect, the present invention provides a method for preparing an oligomeric sulfosuccinate surfactant, comprising the steps of:
a. carrying out a mono-esterification reaction on maleic anhydride and secondary amine ether;
b. the diacid or anhydride and the dihydric alcohol are condensed and polymerized under the action of a catalyst to generate an intermediate connecting group (spacer);
c. b, carrying out double esterification reaction on the mono-esterification product obtained in the step a and the polymerization product obtained in the step b; and
d. c, the double esterification product obtained in the step c and M1S2O5Carrying out conjugate addition sulfonation reaction to obtain a final product,
the specific reaction equation is as follows:
Figure GDA0002483913350000031
Figure GDA0002483913350000041
wherein the content of the first and second substances,
Figure GDA0002483913350000042
R1is C2～C22A medium linear or branched saturated or unsaturated hydrocarbon group, wherein when R is1When the alkyl is unsaturated alkyl, the product obtained by conjugate addition of the alkyl and pyrosulfite is shown as formula III, wherein R is7,R8Is H or C1～C18A medium straight or branched chain saturated hydrocarbon group; r2,R3,R4,R5,R6Are respectively C2～C22A medium linear or branched saturated hydrocarbon group, wherein R3,R4,R5,R6May be the same or different; the intermediate connecting group of the molecule in the formula I is a condensation polymerization product of dibasic acid or anhydride and dihydric alcohol; n is 5 to 50, a is 0 to 100, b is 0 to 100, c is 0 to 100, and d is 0 to 100, which are integers; the products obtained by mono-esterifying secondary amine ether and maleic anhydride are used as two ends of the formula I; m1,M2Are respectively selected from L i+,Na+,K+,NH4 +Wherein M is1,M2The same or different, and the same or different,
Figure GDA0002483913350000043
formula III.
In the monoesterification reaction of the maleic anhydride and the secondary amine ether, the molar ratio of the maleic anhydride to the secondary amine ether may be 1: (0.82 to 1.30), preferably 1: (1.10 to 1.30); the secondary amine ether may be C4～C200Linear or branched saturated hydrocarbyl secondary amine ether, preferably C34～C186More preferably a dibutyl secondary amine ether, a dioctyl secondary amine ether, a didodecyl secondary amine ether, an isomeric bis 13 secondary amine ether and a bis 18 alkyl secondary amine ether.
In the condensation polymerization reaction, the molar ratio of the dibasic acid or anhydride to the dihydric alcohol may be 0.8-0.95: 1, preferably 0.85-0.9: 1; the catalyst can be one or more of sulfuric acid, phosphoric acid, p-toluenesulfonic acid, hydrochloride and sulfate, preferably p-toluenesulfonic acid, and the mass of the p-toluenesulfonic acid can be 0.2-5% of that of the maleic anhydride; the mono-esterification product used for controlling the molecular weight of the polycondensation product can be added, and the molar ratio of the mono-esterification product to the dihydric alcohol can be 0.05-0.1: 1.
In the double esterification reaction, the molar ratio of the added amount of the mono-esterification product to the dihydric alcohol is (0.15-0.45): 1, preferably (0.2-0.3): 1, wherein the added amount of the mono-esterification product comprises the amount of the mono-esterification product added in the condensation polymerization reaction.
In the sulfonation reaction, the horseMaleic anhydride and M2S2O5At a molar ratio of 1.00: 0.11 to 0.85; the M is1S2O5May be selected from L i2SO3,Na2SO3,K2SO3,(NH4)2SO3,LiHSO3,NaHSO3,KHSO3,NH4HSO3,Li2S2O5,Na2S2O5,K2S2O5,(NH4)2S2O5Preferably Na2S2O5。
The method is simple and convenient, easy to operate and good in environmental protection.
The sulfonation reaction of the process is carried out under normal pressure, and the requirement on equipment production conditions is low.
The single-esterification reaction and the double-esterification reaction effectively inhibit the hydrolysis of the esterification products and the yellowing of the color of the products through the inerting operation and the nitrogen protection.
Detailed Description
The present invention will be further described below by way of preparation examples and test examples, which are merely illustrative of the best mode for carrying out the invention, but the present invention is not limited to the following preparation examples and test examples.
Preparation of example 1
Preparation of an oligomeric sulfosuccinate surfactant of formula IV
Figure GDA0002483913350000051
A method for preparing an oligomeric sulfosuccinate surfactant of formula IV, comprising the steps of: a. performing a mono-esterification reaction, namely putting 1.1mol of dibutyl secondary amine ether (2EO-10PO) and 1mol of maleic anhydride as raw materials into an experimental device provided with a stirrer, a thermometer, a water separator and a condenser, inerting the whole experimental device for 3 times, introducing nitrogen for protection, starting a condenser, reacting the raw materials at 40-90 ℃ for 2-8 hours under normal pressure, cooling the condenser by using circulating water, measuring the acid value below 120, and entering the next step; b. c, condensation polymerization reaction, namely continuously adding 1mol of butanediol, 0.9mol of succinic acid and a catalyst of p-toluenesulfonic acid into the reaction container in the step a, keeping introducing nitrogen by taking dimethylbenzene as a water-carrying agent, heating to 100-115 ℃ for reaction, separating water by using a water separator in the reaction process, adding 0.05mol of monoester generated in the step a, continuously reacting until the acid value is less than 50, and finishing the polycondensation reaction; c. b, performing double esterification, namely continuously adding 0.15mol of monoester generated in the step a into the reaction container in the step b, simultaneously heating to 140-180 ℃, keeping the nitrogen protection until the acid value is less than 5, cooling the polycondensation product to 50 +/-30 ℃ after the double esterification is finished, neutralizing the polycondensation product by using 32% NaOH solution until the pH value is 7 +/-0.5, and entering the next step; and d, sulfonation reaction, namely adding the double esterification product and 50% solution of 0.12mol of sodium metabisulfite into an experimental device provided with a condenser and a thermometer, heating to 85-115 ℃ in an oil bath under stirring, preserving the heat, violently stirring, and reacting for 10-20 hours to obtain the product. And adding sodium hydroxide solution into the product, adjusting the pH value to 5-7, bleaching with hydrogen peroxide, and adjusting the solid content to the required solid content with ethanol.
Preparation of examples 1 to 1
Preparation of an oligomeric sulfosuccinate surfactant of formula IV
Figure GDA0002483913350000061
A method for preparing an oligomeric sulfosuccinate surfactant of formula IV, comprising the steps of: a. performing a mono-esterification reaction, namely putting 0.82mol of dibutyl secondary amine ether (2EO-10PO) and 1mol of maleic anhydride as raw materials into an experimental device provided with a stirrer, a thermometer, a water separator and a condenser, inerting the whole experimental device for 3 times, introducing nitrogen for protection, starting a condenser, reacting the raw materials at 40-90 ℃ for 2-8 hours under normal pressure, cooling the condenser by using circulating water, measuring the acid value below 120, and entering the next step; b. c, condensation polymerization reaction, namely continuously adding 1mol of butanediol, 0.9mol of succinic acid and a catalyst of p-toluenesulfonic acid into the reaction container in the step a, keeping introducing nitrogen by taking dimethylbenzene as a water-carrying agent, heating to 100-115 ℃ for reaction, separating water by using a water separator in the reaction process, adding 0.05mol of monoester generated in the step a, continuously reacting until the acid value is less than 50, and finishing the polycondensation reaction; c. b, performing double esterification, namely continuously adding 0.15mol of monoester generated in the step a into the reaction container in the step b, simultaneously heating to 140-180 ℃, keeping the nitrogen protection until the acid value is less than 5, cooling the polycondensation product to 50 +/-30 ℃ after the double esterification is finished, neutralizing the polycondensation product by using 32% NaOH solution until the pH value is 7 +/-0.5, and entering the next step; and d, sulfonation reaction, namely adding the double esterification product and 50% solution of 0.12mol of sodium metabisulfite into an experimental device provided with a condenser and a thermometer, heating to 85-115 ℃ in an oil bath under stirring, preserving the heat, violently stirring, and reacting for 10-20 hours to obtain the product. And adding sodium hydroxide solution into the product, adjusting the pH value to 5-7, bleaching with hydrogen peroxide, and adjusting the solid content to the required solid content with ethanol.
Preparation examples 1 to 2
Preparation of an oligomeric sulfosuccinate surfactant of formula IV
Figure GDA0002483913350000062
A method for preparing an oligomeric sulfosuccinate surfactant of formula IV, comprising the steps of: a. performing a mono-esterification reaction, namely putting 1.2mol of dibutyl secondary amine ether (2EO-10PO) and 1mol of maleic anhydride as raw materials into an experimental device provided with a stirrer, a thermometer, a water separator and a condenser, inerting the whole experimental device for 3 times, introducing nitrogen for protection, starting a condenser, reacting the raw materials at 40-90 ℃ for 2-8 hours under normal pressure, cooling the condenser by using circulating water, measuring the acid value below 120, and entering the next step; b. c, condensation polymerization reaction, namely continuously adding 1mol of butanediol, 0.9mol of succinic acid and a catalyst of p-toluenesulfonic acid into the reaction container in the step a, keeping introducing nitrogen by taking dimethylbenzene as a water-carrying agent, heating to 100-115 ℃ for reaction, separating water by using a water separator in the reaction process, adding 0.05mol of monoester generated in the step a, continuously reacting until the acid value is less than 50, and finishing the polycondensation reaction; c. b, performing double esterification, namely continuously adding 0.15mol of monoester generated in the step a into the reaction container in the step b, simultaneously heating to 140-180 ℃, keeping the nitrogen protection until the acid value is less than 5, cooling the polycondensation product to 50 +/-30 ℃ after the double esterification is finished, neutralizing the polycondensation product by using 32% NaOH solution until the pH value is 7 +/-0.5, and entering the next step; and d, sulfonation reaction, namely adding the double esterification product and 50% solution of 0.12mol of sodium metabisulfite into an experimental device provided with a condenser and a thermometer, heating to 85-115 ℃ in an oil bath under stirring, preserving the heat, violently stirring, and reacting for 10-20 hours to obtain the product. And adding sodium hydroxide solution into the product, adjusting the pH value to 5-7, bleaching with hydrogen peroxide, and adjusting the solid content to the required solid content with ethanol.
Preparation examples 1 to 3
Preparation of an oligomeric sulfosuccinate surfactant of formula IV
Figure GDA0002483913350000071
A method for preparing an oligomeric sulfosuccinate surfactant of formula IV, comprising the steps of: a. performing a mono-esterification reaction, namely putting 1.3mol of dibutyl secondary amine ether (2EO-10PO) and 1mol of maleic anhydride as raw materials into an experimental device provided with a stirrer, a thermometer, a water separator and a condenser, inerting the whole experimental device for 3 times, introducing nitrogen for protection, starting a condenser, reacting the raw materials at 40-90 ℃ for 2-8 hours under normal pressure, cooling the condenser by using circulating water, measuring the acid value below 120, and entering the next step; b. c, condensation polymerization reaction, namely continuously adding 1mol of butanediol, 0.9mol of succinic acid and a catalyst of p-toluenesulfonic acid into the reaction container in the step a, keeping introducing nitrogen by taking dimethylbenzene as a water-carrying agent, heating to 100-115 ℃ for reaction, separating water by using a water separator in the reaction process, adding 0.05mol of monoester generated in the step a, continuously reacting until the acid value is less than 50, and finishing the polycondensation reaction; c. b, performing double esterification, namely continuously adding 0.15mol of monoester generated in the step a into the reaction container in the step b, simultaneously heating to 140-180 ℃, keeping the nitrogen protection until the acid value is less than 5, cooling the polycondensation product to 50 +/-30 ℃ after the double esterification is finished, neutralizing the polycondensation product by using 32% NaOH solution until the pH value is 7 +/-0.5, and entering the next step; and d, sulfonation reaction, namely adding the double esterification product and 50% solution of 0.12mol of sodium metabisulfite into an experimental device provided with a condenser and a thermometer, heating to 85-115 ℃ in an oil bath under stirring, preserving the heat, violently stirring, and reacting for 10-20 hours to obtain the product. And adding sodium hydroxide solution into the product, adjusting the pH value to 5-7, bleaching with hydrogen peroxide, and adjusting the solid content to the required solid content with ethanol.
Preparation examples 1 to 4
Preparation of an oligomeric sulfosuccinate surfactant of formula IV
Figure GDA0002483913350000072
A method for preparing an oligomeric sulfosuccinate surfactant of formula IV, comprising the steps of: a. performing a mono-esterification reaction, namely putting 1.1mol of dibutyl secondary amine ether (2EO-10PO) and 1mol of maleic anhydride as raw materials into an experimental device provided with a stirrer, a thermometer, a water separator and a condenser, inerting the whole experimental device for 3 times, introducing nitrogen for protection, starting a condenser, reacting the raw materials at 40-90 ℃ for 2-8 hours under normal pressure, cooling the condenser by using circulating water, measuring the acid value below 120, and entering the next step; b. c, condensation polymerization reaction, namely continuously adding 1mol of butanediol, 0.8mol of succinic acid and a catalyst of p-toluenesulfonic acid into the reaction container in the step a, keeping introducing nitrogen by taking dimethylbenzene as a water-carrying agent, heating to 100-115 ℃ for reaction, separating water by using a water separator in the reaction process, adding 0.05mol of monoester generated in the step a, continuously reacting until the acid value is less than 50, and finishing the polycondensation reaction; c. b, performing double esterification, namely continuously adding 0.15mol of monoester generated in the step a into the reaction container in the step b, simultaneously heating to 140-180 ℃, keeping the nitrogen protection until the acid value is less than 5, cooling the polycondensation product to 50 +/-30 ℃ after the double esterification is finished, neutralizing the polycondensation product by using 32% NaOH solution until the pH value is 7 +/-0.5, and entering the next step; and d, sulfonation reaction, namely adding the double esterification product and 50% solution of 0.12mol of sodium metabisulfite into an experimental device provided with a condenser and a thermometer, heating to 85-115 ℃ in an oil bath under stirring, preserving the heat, violently stirring, and reacting for 10-20 hours to obtain the product. And adding sodium hydroxide solution into the product, adjusting the pH value to 5-7, bleaching with hydrogen peroxide, and adjusting the solid content to the required solid content with ethanol.
Preparation examples 1 to 5
Preparation of an oligomeric sulfosuccinate surfactant of formula IV
Figure GDA0002483913350000081
A method for preparing an oligomeric sulfosuccinate surfactant of formula IV, comprising the steps of: a. performing a mono-esterification reaction, namely putting 1.1mol of dibutyl secondary amine ether (2EO-10PO) and 1mol of maleic anhydride as raw materials into an experimental device provided with a stirrer, a thermometer, a water separator and a condenser, inerting the whole experimental device for 3 times, introducing nitrogen for protection, starting a condenser, reacting the raw materials at 40-90 ℃ for 2-8 hours under normal pressure, cooling the condenser by using circulating water, measuring the acid value below 120, and entering the next step; b. c, condensation polymerization reaction, namely continuously adding 1mol of butanediol, 0.85mol of succinic acid and a catalyst of p-toluenesulfonic acid into the reaction container in the step a, keeping introducing nitrogen by taking dimethylbenzene as a water-carrying agent, heating to 100-115 ℃ for reaction, separating water by using a water separator in the reaction process, adding 0.05mol of monoester generated in the step a, continuously reacting until the acid value is less than 50, and finishing the polycondensation reaction; c. b, performing double esterification, namely continuously adding 0.15mol of monoester generated in the step a into the reaction container in the step b, simultaneously heating to 140-180 ℃, keeping the nitrogen protection until the acid value is less than 5, cooling the polycondensation product to 50 +/-30 ℃ after the double esterification is finished, neutralizing the polycondensation product by using 32% NaOH solution until the pH value is 7 +/-0.5, and entering the next step; and d, sulfonation reaction, namely adding the double esterification product and 50% solution of 0.12mol of sodium metabisulfite into an experimental device provided with a condenser and a thermometer, heating to 85-115 ℃ in an oil bath under stirring, preserving the heat, violently stirring, and reacting for 10-20 hours to obtain the product. And adding sodium hydroxide solution into the product, adjusting the pH value to 5-7, bleaching with hydrogen peroxide, and adjusting the solid content to the required solid content with ethanol.
Preparation examples 1 to 6
Preparation of an oligomeric sulfosuccinate surfactant of formula IV
Figure GDA0002483913350000091
A method for preparing an oligomeric sulfosuccinate surfactant of formula IV, comprising the steps of: a. performing a mono-esterification reaction, namely putting 1.1mol of dibutyl secondary amine ether (2EO-10PO) and 1mol of maleic anhydride as raw materials into an experimental device provided with a stirrer, a thermometer, a water separator and a condenser, inerting the whole experimental device for 3 times, introducing nitrogen for protection, starting a condenser, reacting the raw materials at 40-90 ℃ for 2-8 hours under normal pressure, cooling the condenser by using circulating water, measuring the acid value below 120, and entering the next step; b. c, condensation polymerization reaction, namely continuously adding 1mol of butanediol, 0.95mol of succinic acid and a catalyst of p-toluenesulfonic acid into the reaction container in the step a, keeping introducing nitrogen by taking dimethylbenzene as a water-carrying agent, heating to 100-115 ℃ for reaction, separating water by using a water separator in the reaction process, adding 0.05mol of monoester generated in the step a, continuously reacting until the acid value is less than 50, and finishing the polycondensation reaction; c. b, performing double esterification, namely continuously adding 0.15mol of monoester generated in the step a into the reaction container in the step b, simultaneously heating to 140-180 ℃, keeping the nitrogen protection until the acid value is less than 5, cooling the polycondensation product to 50 +/-30 ℃ after the double esterification is finished, neutralizing the polycondensation product by using 32% NaOH solution until the pH value is 7 +/-0.5, and entering the next step; and d, sulfonation reaction, namely adding the double esterification product and 50% solution of 0.12mol of sodium metabisulfite into an experimental device provided with a condenser and a thermometer, heating to 85-115 ℃ in an oil bath under stirring, preserving the heat, violently stirring, and reacting for 10-20 hours to obtain the product. And adding sodium hydroxide solution into the product, adjusting the pH value to 5-7, bleaching with hydrogen peroxide, and adjusting the solid content to the required solid content with ethanol.
Preparation examples 1 to 7
Preparation of an oligomeric sulfosuccinate surfactant of formula IV
Figure GDA0002483913350000092
A method for preparing an oligomeric sulfosuccinate surfactant of formula IV, comprising the steps of: a. performing a mono-esterification reaction, namely putting 1.1mol of dibutyl secondary amine ether (2EO-10PO) and 1mol of maleic anhydride as raw materials into an experimental device provided with a stirrer, a thermometer, a water separator and a condenser, inerting the whole experimental device for 3 times, introducing nitrogen for protection, starting a condenser, reacting the raw materials at 40-90 ℃ for 2-8 hours under normal pressure, cooling the condenser by using circulating water, measuring the acid value below 120, and entering the next step; b. c, condensation polymerization reaction, namely continuously adding 1mol of butanediol, 0.9mol of succinic acid and a catalyst of p-toluenesulfonic acid into the reaction container in the step a, keeping introducing nitrogen by taking dimethylbenzene as a water-carrying agent, heating to 100-115 ℃ for reaction, separating water by using a water separator in the reaction process, adding 0.05mol of monoester generated in the step a, continuously reacting until the acid value is less than 50, and finishing the polycondensation reaction; c. b, performing double esterification, namely continuously adding 0.1mol of monoester generated in the step a into the reaction container in the step b, simultaneously heating to 140-180 ℃, keeping the nitrogen protection until the acid value is less than 5, cooling the polycondensation product to 50 +/-30 ℃ after the double esterification is finished, neutralizing the polycondensation product by using 32% NaOH solution until the pH value is 7 +/-0.5, and entering the next step; and d, sulfonation reaction, namely adding the double esterification product and 50% solution of 0.12mol of sodium metabisulfite into an experimental device provided with a condenser and a thermometer, heating to 85-115 ℃ in an oil bath under stirring, preserving the heat, violently stirring, and reacting for 10-20 hours to obtain the product. And adding sodium hydroxide solution into the product, adjusting the pH value to 5-7, bleaching with hydrogen peroxide, and adjusting the solid content to the required solid content with ethanol.
Preparation examples 1 to 8
Preparation of an oligomeric sulfosuccinate surfactant of formula IV
Figure GDA0002483913350000101
A method for preparing an oligomeric sulfosuccinate surfactant of formula IV, comprising the steps of: a. performing a mono-esterification reaction, namely putting 1.1mol of dibutyl secondary amine ether (2EO-10PO) and 1mol of maleic anhydride as raw materials into an experimental device provided with a stirrer, a thermometer, a water separator and a condenser, inerting the whole experimental device for 3 times, introducing nitrogen for protection, starting a condenser, reacting the raw materials at 40-90 ℃ for 2-8 hours under normal pressure, cooling the condenser by using circulating water, measuring the acid value below 120, and entering the next step; b. c, condensation polymerization reaction, namely continuously adding 1mol of butanediol, 0.9mol of succinic acid and a catalyst of p-toluenesulfonic acid into the reaction container in the step a, keeping introducing nitrogen by taking dimethylbenzene as a water-carrying agent, heating to 100-115 ℃ for reaction, separating water by using a water separator in the reaction process, adding 0.05mol of monoester generated in the step a, continuously reacting until the acid value is less than 50, and finishing the polycondensation reaction; c. b, performing double esterification, namely continuously adding 0.4mol of monoester generated in the step a into the reaction container in the step b, simultaneously heating to 140-180 ℃, keeping the nitrogen protection until the acid value is less than 5, cooling the polycondensation product to 50 +/-30 ℃ after the double esterification is finished, neutralizing the polycondensation product by using 32% NaOH solution until the pH value is 7 +/-0.5, and entering the next step; and d, sulfonation reaction, namely adding the double esterification product and 50% solution of 0.12mol of sodium metabisulfite into an experimental device provided with a condenser and a thermometer, heating to 85-115 ℃ in an oil bath under stirring, preserving the heat, violently stirring, and reacting for 10-20 hours to obtain the product. And adding sodium hydroxide solution into the product, adjusting the pH value to 5-7, bleaching with hydrogen peroxide, and adjusting the solid content to the required solid content with ethanol.
Preparation of example 2
Preparation of an oligomeric sulfosuccinate surfactant of formula V
Figure GDA0002483913350000102
A method for preparing an oligomeric sulfosuccinate surfactant of formula V, comprising the steps of: a. performing a mono-esterification reaction, namely putting 1.3mol of dioctyl secondary amine ether (5EO-10PO) and 1mol of maleic anhydride as raw materials into an experimental device provided with a stirrer, a thermometer, a water separator and a condenser, inerting the whole experimental device for 3 times, finally introducing nitrogen for protection, starting a condenser, reacting the raw materials at 50-100 ℃ for 3-10 hours under normal pressure, cooling the condenser by using circulating water, measuring the acid value below 100, and entering the next step; b. c, condensation polymerization reaction, namely, continuously adding 1mol of ethylene glycol, 0.9mol of succinic acid and a catalyst of p-toluenesulfonic acid into the reaction container in the step a, keeping introducing nitrogen by taking dimethylbenzene as a water-carrying agent, heating to 105-125 ℃ for reaction, separating water by using a water separator in the reaction process, reacting for 3 hours, adding 0.05mol of monoester generated in the step a, continuously reacting until the acid value is less than 50, and finishing the polycondensation reaction; c. b, performing double esterification, namely continuously adding 0.15mol of monoester generated in the step a into the reaction container in the step b, simultaneously heating to 130-185 ℃, keeping the nitrogen protection until the acid value is less than 5, cooling the polycondensation product to 50 +/-30 ℃ after the double esterification is finished, neutralizing the polycondensation product by using 32% NaOH solution until the pH value is 7 +/-0.5, and entering the next step; and d, sulfonation reaction, namely adding the double esterification product and 50% solution of 0.11mol of sodium metabisulfite into an experimental device provided with a condenser and a thermometer, heating to 85-115 ℃ in an oil bath under stirring, preserving heat, violently stirring, and reacting for 10-20 hours to obtain the product. And adding sodium hydroxide solution into the product, adjusting the pH value to 5-7, bleaching with hydrogen peroxide, and adjusting the solid content to the required solid content with ethanol.
Preparation example 2-1
Preparation of an oligomeric sulfosuccinate surfactant of formula V
Figure GDA0002483913350000111
A method for preparing an oligomeric sulfosuccinate surfactant of formula V, comprising the steps of: a. performing a mono-esterification reaction, namely putting 0.82mol of dioctyl secondary amine ether (5EO-10PO) and 1mol of maleic anhydride as raw materials into an experimental device provided with a stirrer, a thermometer, a water separator and a condenser, inerting the whole experimental device for 3 times, finally introducing nitrogen for protection, starting a condenser, reacting the raw materials at 50-100 ℃ for 3-10 hours under normal pressure, cooling the condenser by using circulating water, measuring the acid value below 100, and entering the next step; b. c, condensation polymerization reaction, namely, continuously adding 1mol of ethylene glycol, 0.9mol of succinic acid and a catalyst of p-toluenesulfonic acid into the reaction container in the step a, keeping introducing nitrogen by taking dimethylbenzene as a water-carrying agent, heating to 105-125 ℃ for reaction, separating water by using a water separator in the reaction process, reacting for 3 hours, adding 0.05mol of monoester generated in the step a, continuously reacting until the acid value is less than 50, and finishing the polycondensation reaction; c. b, performing double esterification, namely continuously adding 0.15mol of monoester generated in the step a into the reaction container in the step b, simultaneously heating to 130-185 ℃, keeping the nitrogen protection until the acid value is less than 5, cooling the polycondensation product to 50 +/-30 ℃ after the double esterification is finished, neutralizing the polycondensation product by using 32% NaOH solution until the pH value is 7 +/-0.5, and entering the next step; and d, sulfonation reaction, namely adding the double esterification product and 50% solution of 0.11mol of sodium metabisulfite into an experimental device provided with a condenser and a thermometer, heating to 85-115 ℃ in an oil bath under stirring, preserving heat, violently stirring, and reacting for 10-20 hours to obtain the product. And adding sodium hydroxide solution into the product, adjusting the pH value to 5-7, bleaching with hydrogen peroxide, and adjusting the solid content to the required solid content with ethanol.
Preparation examples 2 to 2
Preparation of an oligomeric sulfosuccinate surfactant of formula V
Figure GDA0002483913350000112
Figure GDA0002483913350000121
A method for preparing an oligomeric sulfosuccinate surfactant of formula V, comprising the steps of: a. performing a mono-esterification reaction, namely putting 1.1mol of dioctyl secondary amine ether (5EO-10PO) and 1mol of maleic anhydride as raw materials into an experimental device provided with a stirrer, a thermometer, a water separator and a condenser, inerting the whole experimental device for 3 times, finally introducing nitrogen for protection, starting a condenser, reacting the raw materials at 50-100 ℃ for 3-10 hours under normal pressure, cooling the condenser by using circulating water, measuring the acid value below 100, and entering the next step; b. c, condensation polymerization reaction, namely, continuously adding 1mol of ethylene glycol, 0.9mol of succinic acid and a catalyst of p-toluenesulfonic acid into the reaction container in the step a, keeping introducing nitrogen by taking dimethylbenzene as a water-carrying agent, heating to 105-125 ℃ for reaction, separating water by using a water separator in the reaction process, reacting for 3 hours, adding 0.05mol of monoester generated in the step a, continuously reacting until the acid value is less than 50, and finishing the polycondensation reaction; c. b, performing double esterification, namely continuously adding 0.15mol of monoester generated in the step a into the reaction container in the step b, simultaneously heating to 130-185 ℃, keeping the nitrogen protection until the acid value is less than 5, cooling the polycondensation product to 50 +/-30 ℃ after the double esterification is finished, neutralizing the polycondensation product by using 32% NaOH solution until the pH value is 7 +/-0.5, and entering the next step; and d, sulfonation reaction, namely adding the double esterification product and 50% solution of 0.11mol of sodium metabisulfite into an experimental device provided with a condenser and a thermometer, heating to 85-115 ℃ in an oil bath under stirring, preserving heat, violently stirring, and reacting for 10-20 hours to obtain the product. And adding sodium hydroxide solution into the product, adjusting the pH value to 5-7, bleaching with hydrogen peroxide, and adjusting the solid content to the required solid content with ethanol.
Preparation examples 2 to 3
Preparation of an oligomeric sulfosuccinate surfactant of formula V
Figure GDA0002483913350000122
A method for preparing an oligomeric sulfosuccinate surfactant of formula V, comprising the steps of: a. performing a mono-esterification reaction, namely putting 1.2mol of dioctyl secondary amine ether (5EO-10PO) and 1mol of maleic anhydride as raw materials into an experimental device provided with a stirrer, a thermometer, a water separator and a condenser, inerting the whole experimental device for 3 times, finally introducing nitrogen for protection, starting a condenser, reacting the raw materials at 50-100 ℃ for 3-10 hours under normal pressure, cooling the condenser by using circulating water, measuring the acid value below 100, and entering the next step; b. c, condensation polymerization reaction, namely, continuously adding 1mol of ethylene glycol, 0.9mol of succinic acid and a catalyst of p-toluenesulfonic acid into the reaction container in the step a, keeping introducing nitrogen by taking dimethylbenzene as a water-carrying agent, heating to 105-125 ℃ for reaction, separating water by using a water separator in the reaction process, reacting for 3 hours, adding 0.05mol of monoester generated in the step a, continuously reacting until the acid value is less than 50, and finishing the polycondensation reaction; c. b, performing double esterification, namely continuously adding 0.15mol of monoester generated in the step a into the reaction container in the step b, simultaneously heating to 130-185 ℃, keeping the nitrogen protection until the acid value is less than 5, cooling the polycondensation product to 50 +/-30 ℃ after the double esterification is finished, neutralizing the polycondensation product by using 32% NaOH solution until the pH value is 7 +/-0.5, and entering the next step; and d, sulfonation reaction, namely adding the double esterification product and 50% solution of 0.11mol of sodium metabisulfite into an experimental device provided with a condenser and a thermometer, heating to 85-115 ℃ in an oil bath under stirring, preserving heat, violently stirring, and reacting for 10-20 hours to obtain the product. And adding sodium hydroxide solution into the product, adjusting the pH value to 5-7, bleaching with hydrogen peroxide, and adjusting the solid content to the required solid content with ethanol.
Preparation examples 2 to 4
Preparation of an oligomeric sulfosuccinate surfactant of formula V
Figure GDA0002483913350000131
A method for preparing an oligomeric sulfosuccinate surfactant of formula V, comprising the steps of: a. performing a mono-esterification reaction, namely putting 1.3mol of dioctyl secondary amine ether (5EO-10PO) and 1mol of maleic anhydride as raw materials into an experimental device provided with a stirrer, a thermometer, a water separator and a condenser, inerting the whole experimental device for 3 times, finally introducing nitrogen for protection, starting a condenser, reacting the raw materials at 50-100 ℃ for 3-10 hours under normal pressure, cooling the condenser by using circulating water, measuring the acid value below 100, and entering the next step; b. c, condensation polymerization reaction, namely, continuously adding 1mol of ethylene glycol, 0.8mol of succinic acid and a catalyst of p-toluenesulfonic acid into the reaction container in the step a, keeping introducing nitrogen by taking dimethylbenzene as a water-carrying agent, heating to 105-125 ℃ for reaction, separating water by using a water separator in the reaction process, reacting for 3 hours, adding 0.05mol of monoester generated in the step a, continuously reacting until the acid value is less than 50, and finishing the polycondensation reaction; c. b, performing double esterification, namely continuously adding 0.15mol of monoester generated in the step a into the reaction container in the step b, simultaneously heating to 130-185 ℃, keeping the nitrogen protection until the acid value is less than 5, cooling the polycondensation product to 50 +/-30 ℃ after the double esterification is finished, neutralizing the polycondensation product by using 32% NaOH solution until the pH value is 7 +/-0.5, and entering the next step; and d, sulfonation reaction, namely adding the double esterification product and 50% solution of 0.11mol of sodium metabisulfite into an experimental device provided with a condenser and a thermometer, heating to 85-115 ℃ in an oil bath under stirring, preserving heat, violently stirring, and reacting for 10-20 hours to obtain the product. And adding sodium hydroxide solution into the product, adjusting the pH value to 5-7, bleaching with hydrogen peroxide, and adjusting the solid content to the required solid content with ethanol.
Preparation examples 2 to 5
Preparation of an oligomeric sulfosuccinate surfactant of formula V
Figure GDA0002483913350000132
A method for preparing an oligomeric sulfosuccinate surfactant of formula V, comprising the steps of: a. performing a mono-esterification reaction, namely putting 1.3mol of dioctyl secondary amine ether (5EO-10PO) and 1mol of maleic anhydride as raw materials into an experimental device provided with a stirrer, a thermometer, a water separator and a condenser, inerting the whole experimental device for 3 times, finally introducing nitrogen for protection, starting a condenser, reacting the raw materials at 50-100 ℃ for 3-10 hours under normal pressure, cooling the condenser by using circulating water, measuring the acid value below 100, and entering the next step; b. c, condensation polymerization reaction, namely, continuously adding 1mol of ethylene glycol, 0.85mol of succinic acid and a catalyst of p-toluenesulfonic acid into the reaction container in the step a, keeping introducing nitrogen by taking dimethylbenzene as a water-carrying agent, heating to 105-125 ℃ for reaction, separating water by using a water separator in the reaction process, reacting for 3 hours, adding 0.05mol of monoester generated in the step a, continuously reacting until the acid value is less than 50, and finishing the polycondensation reaction; c. b, performing double esterification, namely continuously adding 0.15mol of monoester generated in the step a into the reaction container in the step b, simultaneously heating to 130-185 ℃, keeping the nitrogen protection until the acid value is less than 5, cooling the polycondensation product to 50 +/-30 ℃ after the double esterification is finished, neutralizing the polycondensation product by using 32% NaOH solution until the pH value is 7 +/-0.5, and entering the next step; and d, sulfonation reaction, namely adding the double esterification product and 50% solution of 0.11mol of sodium metabisulfite into an experimental device provided with a condenser and a thermometer, heating to 85-115 ℃ in an oil bath under stirring, preserving heat, violently stirring, and reacting for 10-20 hours to obtain the product. And adding sodium hydroxide solution into the product, adjusting the pH value to 5-7, bleaching with hydrogen peroxide, and adjusting the solid content to the required solid content with ethanol.
Preparation examples 2 to 6
Preparation of an oligomeric sulfosuccinate surfactant of formula V
Figure GDA0002483913350000141
A method for preparing an oligomeric sulfosuccinate surfactant of formula V, comprising the steps of: a. performing a mono-esterification reaction, namely putting 1.3mol of dioctyl secondary amine ether (5EO-10PO) and 1mol of maleic anhydride as raw materials into an experimental device provided with a stirrer, a thermometer, a water separator and a condenser, inerting the whole experimental device for 3 times, finally introducing nitrogen for protection, starting a condenser, reacting the raw materials at 50-100 ℃ for 3-10 hours under normal pressure, cooling the condenser by using circulating water, measuring the acid value below 100, and entering the next step; b. c, condensation polymerization reaction, namely, continuously adding 1mol of ethylene glycol, 0.95mol of succinic acid and a catalyst of p-toluenesulfonic acid into the reaction container in the step a, keeping introducing nitrogen by taking dimethylbenzene as a water-carrying agent, heating to 105-125 ℃ for reaction, separating water by using a water separator in the reaction process, reacting for 3 hours, adding 0.05mol of monoester generated in the step a, continuously reacting until the acid value is less than 50, and finishing the polycondensation reaction; c. b, performing double esterification, namely continuously adding 0.15mol of monoester generated in the step a into the reaction container in the step b, simultaneously heating to 130-185 ℃, keeping the nitrogen protection until the acid value is less than 5, cooling the polycondensation product to 50 +/-30 ℃ after the double esterification is finished, neutralizing the polycondensation product by using 32% NaOH solution until the pH value is 7 +/-0.5, and entering the next step; and d, sulfonation reaction, namely adding the double esterification product and 50% solution of 0.11mol of sodium metabisulfite into an experimental device provided with a condenser and a thermometer, heating to 85-115 ℃ in an oil bath under stirring, preserving heat, violently stirring, and reacting for 10-20 hours to obtain the product. And adding sodium hydroxide solution into the product, adjusting the pH value to 5-7, bleaching with hydrogen peroxide, and adjusting the solid content to the required solid content with ethanol.
Preparation examples 2 to 7
Preparation of an oligomeric sulfosuccinate surfactant of formula V
Figure GDA0002483913350000142
A method for preparing an oligomeric sulfosuccinate surfactant of formula V, comprising the steps of: a. performing a mono-esterification reaction, namely putting 1.3mol of dioctyl secondary amine ether (5EO-10PO) and 1mol of maleic anhydride as raw materials into an experimental device provided with a stirrer, a thermometer, a water separator and a condenser, inerting the whole experimental device for 3 times, finally introducing nitrogen for protection, starting a condenser, reacting the raw materials at 50-100 ℃ for 3-10 hours under normal pressure, cooling the condenser by using circulating water, measuring the acid value below 100, and entering the next step; b. c, condensation polymerization reaction, namely, continuously adding 1mol of ethylene glycol, 0.9mol of succinic acid and a catalyst of p-toluenesulfonic acid into the reaction container in the step a, keeping introducing nitrogen by taking dimethylbenzene as a water-carrying agent, heating to 105-125 ℃ for reaction, separating water by using a water separator in the reaction process, reacting for 3 hours, adding 0.05mol of monoester generated in the step a, continuously reacting until the acid value is less than 50, and finishing the polycondensation reaction; c. b, performing double esterification, namely continuously adding 0.1mol of monoester generated in the step a into the reaction container in the step b, simultaneously heating to 130-185 ℃, keeping the nitrogen protection until the acid value is less than 5, cooling the polycondensation product to 50 +/-30 ℃ after the double esterification is finished, neutralizing the polycondensation product by using 32% NaOH solution until the pH value is 7 +/-0.5, and entering the next step; and d, sulfonation reaction, namely adding the double esterification product and 50% solution of 0.11mol of sodium metabisulfite into an experimental device provided with a condenser and a thermometer, heating to 85-115 ℃ in an oil bath under stirring, preserving heat, violently stirring, and reacting for 10-20 hours to obtain the product. And adding sodium hydroxide solution into the product, adjusting the pH value to 5-7, bleaching with hydrogen peroxide, and adjusting the solid content to the required solid content with ethanol.
Preparation examples 2 to 8
Preparation of an oligomeric sulfosuccinate surfactant of formula V
Figure GDA0002483913350000151
A method for preparing an oligomeric sulfosuccinate surfactant of formula V, comprising the steps of: a. performing a mono-esterification reaction, namely putting 1.3mol of dioctyl secondary amine ether (5EO-10PO) and 1mol of maleic anhydride as raw materials into an experimental device provided with a stirrer, a thermometer, a water separator and a condenser, inerting the whole experimental device for 3 times, finally introducing nitrogen for protection, starting a condenser, reacting the raw materials at 50-100 ℃ for 3-10 hours under normal pressure, cooling the condenser by using circulating water, measuring the acid value below 100, and entering the next step; b. c, condensation polymerization reaction, namely, continuously adding 1mol of ethylene glycol, 0.9mol of succinic acid and a catalyst of p-toluenesulfonic acid into the reaction container in the step a, keeping introducing nitrogen by taking dimethylbenzene as a water-carrying agent, heating to 105-125 ℃ for reaction, separating water by using a water separator in the reaction process, reacting for 3 hours, adding 0.05mol of monoester generated in the step a, continuously reacting until the acid value is less than 50, and finishing the polycondensation reaction; c. b, performing double esterification, namely continuously adding 0.4mol of monoester generated in the step a into the reaction container in the step b, simultaneously heating to 130-185 ℃, keeping the nitrogen protection until the acid value is less than 5, cooling the polycondensation product to 50 +/-30 ℃ after the double esterification is finished, neutralizing the polycondensation product by using 32% NaOH solution until the pH value is 7 +/-0.5, and entering the next step; and d, sulfonation reaction, namely adding the double esterification product and 50% solution of 0.11mol of sodium metabisulfite into an experimental device provided with a condenser and a thermometer, heating to 85-115 ℃ in an oil bath under stirring, preserving heat, violently stirring, and reacting for 10-20 hours to obtain the product. And adding sodium hydroxide solution into the product, adjusting the pH value to 5-7, bleaching with hydrogen peroxide, and adjusting the solid content to the required solid content with ethanol.
Preparation of example 3
Preparation of an oligomeric sulfosuccinate surfactant of formula VI
Figure GDA0002483913350000161
A method for preparing an oligomeric sulfosuccinate surfactant of formula VI, comprising the steps of: a. performing a mono-esterification reaction, namely putting 1.3mol of didodecyl secondary amine ether (5EO) and 1mol of maleic anhydride as raw materials into an experimental device provided with a stirrer, a thermometer, a water separator and a condenser, inerting the whole experimental device for 3 times, finally introducing nitrogen for protection, starting the condenser, reacting the raw materials for 2-11 hours at 55-85 ℃ under normal pressure, cooling the raw materials by using circulating water, measuring the acid value below 140, and entering the next step; b. c, condensation polymerization reaction, namely, continuously adding 1mol of ethylene glycol, 0.85mol of maleic acid and a catalyst p-toluenesulfonic acid into the reaction container in the step a, keeping introducing nitrogen by taking dimethylbenzene as a water-carrying agent, heating to 105-125 ℃ for reaction, separating water by using a water separator in the reaction process, reacting for 3 hours, adding 0.1mol of monoester generated in the step a, continuously reacting until the acid value is less than 50, and finishing the polycondensation reaction; c. b, performing double esterification, namely continuously adding 0.2mol of monoester generated in the step a into the reaction container in the step b, simultaneously heating to 145-185 ℃, keeping the nitrogen protection until the acid value is less than 5, cooling the polycondensation product to 50 +/-30 ℃ after the double esterification is finished, neutralizing the polycondensation product by using 32% NaOH solution until the pH value is 7 +/-0.5, and entering the next step; and d, sulfonation reaction, namely adding the double esterification product and 50% solution of 0.85mol of sodium metabisulfite into an experimental device provided with a condenser and a thermometer, heating to 85-115 ℃ in an oil bath under stirring, preserving heat, violently stirring, and reacting for 10-20 hours to obtain the product. And adding sodium hydroxide solution into the product, adjusting the pH value to 5-7, bleaching with hydrogen peroxide, and adjusting the solid content to the required solid content with ethanol.
Preparation of example 3-1
Preparation of an oligomeric sulfosuccinate surfactant of formula VI
Figure GDA0002483913350000162
A method for preparing an oligomeric sulfosuccinate surfactant of formula VI, comprising the steps of: a. performing a mono-esterification reaction, namely putting 0.82mol of didodecyl secondary amine ether (5EO) and 1mol of maleic anhydride as raw materials into an experimental device provided with a stirrer, a thermometer, a water separator and a condenser, inerting the whole experimental device for 3 times, finally introducing nitrogen for protection, starting the condenser, reacting the raw materials for 2-11 hours at 55-85 ℃ under normal pressure, cooling the raw materials by using circulating water, measuring the acid value below 140, and entering the next step; b. c, condensation polymerization reaction, namely, continuously adding 1mol of ethylene glycol, 0.85mol of maleic acid and a catalyst p-toluenesulfonic acid into the reaction container in the step a, keeping introducing nitrogen by taking dimethylbenzene as a water-carrying agent, heating to 105-125 ℃ for reaction, separating water by using a water separator in the reaction process, reacting for 3 hours, adding 0.1mol of monoester generated in the step a, continuously reacting until the acid value is less than 50, and finishing the polycondensation reaction; c. b, performing double esterification, namely continuously adding 0.2mol of monoester generated in the step a into the reaction container in the step b, simultaneously heating to 145-185 ℃, keeping the nitrogen protection until the acid value is less than 5, cooling the polycondensation product to 50 +/-30 ℃ after the double esterification is finished, neutralizing the polycondensation product by using 32% NaOH solution until the pH value is 7 +/-0.5, and entering the next step; and d, sulfonation reaction, namely adding the double esterification product and 50% solution of 0.85mol of sodium metabisulfite into an experimental device provided with a condenser and a thermometer, heating to 85-115 ℃ in an oil bath under stirring, preserving heat, violently stirring, and reacting for 10-20 hours to obtain the product. And adding sodium hydroxide solution into the product, adjusting the pH value to 5-7, bleaching with hydrogen peroxide, and adjusting the solid content to the required solid content with ethanol.
Preparation examples 3 to 2
Preparation of an oligomeric sulfosuccinate surfactant of formula VI
Figure GDA0002483913350000171
A method for preparing an oligomeric sulfosuccinate surfactant of formula VI, comprising the steps of: a. performing a mono-esterification reaction, namely putting 1.1mol of didodecyl secondary amine ether (5EO) and 1mol of maleic anhydride as raw materials into an experimental device provided with a stirrer, a thermometer, a water separator and a condenser, inerting the whole experimental device for 3 times, finally introducing nitrogen for protection, starting the condenser, reacting the raw materials for 2-11 hours at 55-85 ℃ under normal pressure, cooling the raw materials by using circulating water, measuring the acid value below 140, and entering the next step; b. c, condensation polymerization reaction, namely, continuously adding 1mol of ethylene glycol, 0.85mol of maleic acid and a catalyst p-toluenesulfonic acid into the reaction container in the step a, keeping introducing nitrogen by taking dimethylbenzene as a water-carrying agent, heating to 105-125 ℃ for reaction, separating water by using a water separator in the reaction process, reacting for 3 hours, adding 0.1mol of monoester generated in the step a, continuously reacting until the acid value is less than 50, and finishing the polycondensation reaction; c. b, performing double esterification, namely continuously adding 0.2mol of monoester generated in the step a into the reaction container in the step b, simultaneously heating to 145-185 ℃, keeping the nitrogen protection until the acid value is less than 5, cooling the polycondensation product to 50 +/-30 ℃ after the double esterification is finished, neutralizing the polycondensation product by using 32% NaOH solution until the pH value is 7 +/-0.5, and entering the next step; and d, sulfonation reaction, namely adding the double esterification product and 50% solution of 0.85mol of sodium metabisulfite into an experimental device provided with a condenser and a thermometer, heating to 85-115 ℃ in an oil bath under stirring, preserving heat, violently stirring, and reacting for 10-20 hours to obtain the product. And adding sodium hydroxide solution into the product, adjusting the pH value to 5-7, bleaching with hydrogen peroxide, and adjusting the solid content to the required solid content with ethanol.
Preparation examples 3 to 3
Preparation of an oligomeric sulfosuccinate surfactant of formula VI
Figure GDA0002483913350000172
A method for preparing an oligomeric sulfosuccinate surfactant of formula VI, comprising the steps of: a. performing a mono-esterification reaction, namely putting 1.2mol of didodecyl secondary amine ether (5EO) and 1mol of maleic anhydride as raw materials into an experimental device provided with a stirrer, a thermometer, a water separator and a condenser, inerting the whole experimental device for 3 times, finally introducing nitrogen for protection, starting the condenser, reacting the raw materials for 2-11 hours at 55-85 ℃ under normal pressure, cooling the raw materials by using circulating water, measuring the acid value below 140, and entering the next step; b. c, condensation polymerization reaction, namely, continuously adding 1mol of ethylene glycol, 0.85mol of maleic acid and a catalyst p-toluenesulfonic acid into the reaction container in the step a, keeping introducing nitrogen by taking dimethylbenzene as a water-carrying agent, heating to 105-125 ℃ for reaction, separating water by using a water separator in the reaction process, reacting for 3 hours, adding 0.1mol of monoester generated in the step a, continuously reacting until the acid value is less than 50, and finishing the polycondensation reaction; c. b, performing double esterification, namely continuously adding 0.2mol of monoester generated in the step a into the reaction container in the step b, simultaneously heating to 145-185 ℃, keeping the nitrogen protection until the acid value is less than 5, cooling the polycondensation product to 50 +/-30 ℃ after the double esterification is finished, neutralizing the polycondensation product by using 32% NaOH solution until the pH value is 7 +/-0.5, and entering the next step; and d, sulfonation reaction, namely adding the double esterification product and 50% solution of 0.85mol of sodium metabisulfite into an experimental device provided with a condenser and a thermometer, heating to 85-115 ℃ in an oil bath under stirring, preserving heat, violently stirring, and reacting for 10-20 hours to obtain the product. And adding sodium hydroxide solution into the product, adjusting the pH value to 5-7, bleaching with hydrogen peroxide, and adjusting the solid content to the required solid content with ethanol.
Preparation examples 3 to 4
Preparation of an oligomeric sulfosuccinate surfactant of formula VI
Figure GDA0002483913350000181
A method for preparing an oligomeric sulfosuccinate surfactant of formula VI, comprising the steps of: a. performing a mono-esterification reaction, namely putting 1.3mol of didodecyl secondary amine ether (5EO) and 1mol of maleic anhydride as raw materials into an experimental device provided with a stirrer, a thermometer, a water separator and a condenser, inerting the whole experimental device for 3 times, finally introducing nitrogen for protection, starting the condenser, reacting the raw materials for 2-11 hours at 55-85 ℃ under normal pressure, cooling the raw materials by using circulating water, measuring the acid value below 140, and entering the next step; b. c, condensation polymerization reaction, namely, continuously adding 1mol of ethylene glycol, 0.8mol of maleic acid and a catalyst p-toluenesulfonic acid into the reaction container in the step a, keeping introducing nitrogen by taking dimethylbenzene as a water-carrying agent, heating to 105-125 ℃ for reaction, separating water by using a water separator in the reaction process, reacting for 3 hours, adding 0.1mol of monoester generated in the step a, continuously reacting until the acid value is less than 50, and finishing the polycondensation reaction; c. b, performing double esterification, namely continuously adding 0.2mol of monoester generated in the step a into the reaction container in the step b, simultaneously heating to 145-185 ℃, keeping the nitrogen protection until the acid value is less than 5, cooling the polycondensation product to 50 +/-30 ℃ after the double esterification is finished, neutralizing the polycondensation product by using 32% NaOH solution until the pH value is 7 +/-0.5, and entering the next step; and d, sulfonation reaction, namely adding the double esterification product and 50% solution of 0.85mol of sodium metabisulfite into an experimental device provided with a condenser and a thermometer, heating to 85-115 ℃ in an oil bath under stirring, preserving heat, violently stirring, and reacting for 10-20 hours to obtain the product. And adding sodium hydroxide solution into the product, adjusting the pH value to 5-7, bleaching with hydrogen peroxide, and adjusting the solid content to the required solid content with ethanol.
Preparation examples 3 to 5
Preparation of an oligomeric sulfosuccinate surfactant of formula VI
Figure GDA0002483913350000182
A method for preparing an oligomeric sulfosuccinate surfactant of formula VI, comprising the steps of: a. performing a mono-esterification reaction, namely putting 1.3mol of didodecyl secondary amine ether (5EO) and 1mol of maleic anhydride as raw materials into an experimental device provided with a stirrer, a thermometer, a water separator and a condenser, inerting the whole experimental device for 3 times, finally introducing nitrogen for protection, starting the condenser, reacting the raw materials for 2-11 hours at 55-85 ℃ under normal pressure, cooling the raw materials by using circulating water, measuring the acid value below 140, and entering the next step; b. c, condensation polymerization reaction, namely, continuously adding 1mol of ethylene glycol, 0.9mol of maleic acid and a catalyst p-toluenesulfonic acid into the reaction container in the step a, keeping introducing nitrogen by taking dimethylbenzene as a water-carrying agent, heating to 105-125 ℃ for reaction, separating water by using a water separator in the reaction process, reacting for 3 hours, adding 0.1mol of monoester generated in the step a, continuously reacting until the acid value is less than 50, and finishing the polycondensation reaction; c. b, performing double esterification, namely continuously adding 0.2mol of monoester generated in the step a into the reaction container in the step b, simultaneously heating to 145-185 ℃, keeping the nitrogen protection until the acid value is less than 5, cooling the polycondensation product to 50 +/-30 ℃ after the double esterification is finished, neutralizing the polycondensation product by using 32% NaOH solution until the pH value is 7 +/-0.5, and entering the next step; and d, sulfonation reaction, namely adding the double esterification product and 50% solution of 0.85mol of sodium metabisulfite into an experimental device provided with a condenser and a thermometer, heating to 85-115 ℃ in an oil bath under stirring, preserving heat, violently stirring, and reacting for 10-20 hours to obtain the product. And adding sodium hydroxide solution into the product, adjusting the pH value to 5-7, bleaching with hydrogen peroxide, and adjusting the solid content to the required solid content with ethanol.
Preparation examples 3 to 6
Preparation of an oligomeric sulfosuccinate surfactant of formula VI
Figure GDA0002483913350000191
A method for preparing an oligomeric sulfosuccinate surfactant of formula VI, comprising the steps of: a. performing a mono-esterification reaction, namely putting 1.3mol of didodecyl secondary amine ether (5EO) and 1mol of maleic anhydride as raw materials into an experimental device provided with a stirrer, a thermometer, a water separator and a condenser, inerting the whole experimental device for 3 times, finally introducing nitrogen for protection, starting the condenser, reacting the raw materials for 2-11 hours at 55-85 ℃ under normal pressure, cooling the raw materials by using circulating water, measuring the acid value below 140, and entering the next step; b. c, condensation polymerization reaction, namely, continuously adding 1mol of ethylene glycol, 0.95mol of maleic acid and a catalyst p-toluenesulfonic acid into the reaction container in the step a, keeping introducing nitrogen by taking dimethylbenzene as a water-carrying agent, heating to 105-125 ℃ for reaction, separating water by using a water separator in the reaction process, reacting for 3 hours, adding 0.1mol of monoester generated in the step a, continuously reacting until the acid value is less than 50, and finishing the polycondensation reaction; c. b, performing double esterification, namely continuously adding 0.2mol of monoester generated in the step a into the reaction container in the step b, simultaneously heating to 145-185 ℃, keeping the nitrogen protection until the acid value is less than 5, cooling the polycondensation product to 50 +/-30 ℃ after the double esterification is finished, neutralizing the polycondensation product by using 32% NaOH solution until the pH value is 7 +/-0.5, and entering the next step; and d, sulfonation reaction, namely adding the double esterification product and 50% solution of 0.85mol of sodium metabisulfite into an experimental device provided with a condenser and a thermometer, heating to 85-115 ℃ in an oil bath under stirring, preserving heat, violently stirring, and reacting for 10-20 hours to obtain the product. And adding sodium hydroxide solution into the product, adjusting the pH value to 5-7, bleaching with hydrogen peroxide, and adjusting the solid content to the required solid content with ethanol.
Preparation examples 3 to 7
Preparation of an oligomeric sulfosuccinate surfactant of formula VI
Figure GDA0002483913350000201
A method for preparing an oligomeric sulfosuccinate surfactant of formula VI, comprising the steps of: a. performing a mono-esterification reaction, namely putting 1.3mol of didodecyl secondary amine ether (5EO) and 1mol of maleic anhydride as raw materials into an experimental device provided with a stirrer, a thermometer, a water separator and a condenser, inerting the whole experimental device for 3 times, finally introducing nitrogen for protection, starting the condenser, reacting the raw materials for 2-11 hours at 55-85 ℃ under normal pressure, cooling the raw materials by using circulating water, measuring the acid value below 140, and entering the next step; b. c, condensation polymerization reaction, namely, continuously adding 1mol of ethylene glycol, 0.85mol of maleic acid and a catalyst p-toluenesulfonic acid into the reaction container in the step a, keeping introducing nitrogen by taking dimethylbenzene as a water-carrying agent, heating to 105-125 ℃ for reaction, separating water by using a water separator in the reaction process, reacting for 3 hours, adding 0.1mol of monoester generated in the step a, continuously reacting until the acid value is less than 50, and finishing the polycondensation reaction; c. b, performing double esterification, namely continuously adding 0.05mol of monoester generated in the step a into the reaction container in the step b, simultaneously heating to 145-185 ℃, keeping the nitrogen protection until the acid value is less than 5, cooling the polycondensation product to 50 +/-30 ℃ after the double esterification is finished, neutralizing the polycondensation product by using 32% NaOH solution until the pH value is 7 +/-0.5, and entering the next step; and d, sulfonation reaction, namely adding the double esterification product and 50% solution of 0.85mol of sodium metabisulfite into an experimental device provided with a condenser and a thermometer, heating to 85-115 ℃ in an oil bath under stirring, preserving heat, violently stirring, and reacting for 10-20 hours to obtain the product. And adding sodium hydroxide solution into the product, adjusting the pH value to 5-7, bleaching with hydrogen peroxide, and adjusting the solid content to the required solid content with ethanol.
Preparation examples 3 to 8
Preparation of an oligomeric sulfosuccinate surfactant of formula VI
Figure GDA0002483913350000202
A method for preparing an oligomeric sulfosuccinate surfactant of formula VI, comprising the steps of: a. performing a mono-esterification reaction, namely putting 1.3mol of didodecyl secondary amine ether (5EO) and 1mol of maleic anhydride as raw materials into an experimental device provided with a stirrer, a thermometer, a water separator and a condenser, inerting the whole experimental device for 3 times, finally introducing nitrogen for protection, starting the condenser, reacting the raw materials for 2-11 hours at 55-85 ℃ under normal pressure, cooling the raw materials by using circulating water, measuring the acid value below 140, and entering the next step; b. c, condensation polymerization reaction, namely, continuously adding 1mol of ethylene glycol, 0.85mol of maleic acid and a catalyst p-toluenesulfonic acid into the reaction container in the step a, keeping introducing nitrogen by taking dimethylbenzene as a water-carrying agent, heating to 105-125 ℃ for reaction, separating water by using a water separator in the reaction process, reacting for 3 hours, adding 0.1mol of monoester generated in the step a, continuously reacting until the acid value is less than 50, and finishing the polycondensation reaction; c. b, performing double esterification, namely continuously adding 0.35mol of monoester generated in the step a into the reaction container in the step b, simultaneously heating to 145-185 ℃, keeping the nitrogen protection until the acid value is less than 5, cooling the polycondensation product to 50 +/-30 ℃ after the double esterification is finished, neutralizing the polycondensation product by using 32% NaOH solution until the pH value is 7 +/-0.5, and entering the next step; and d, sulfonation reaction, namely adding the double esterification product and 50% solution of 0.85mol of sodium metabisulfite into an experimental device provided with a condenser and a thermometer, heating to 85-115 ℃ in an oil bath under stirring, preserving heat, violently stirring, and reacting for 10-20 hours to obtain the product. And adding sodium hydroxide solution into the product, adjusting the pH value to 5-7, bleaching with hydrogen peroxide, and adjusting the solid content to the required solid content with ethanol.
Preparation of example 4
Preparation of an oligomeric sulfosuccinate surfactant of formula VII
Figure GDA0002483913350000211
A method for preparing an oligomeric sulfosuccinate surfactant of formula VII, comprising the steps of: a. performing a mono-esterification reaction, namely putting 1.2mol of isomeric bis-13 secondary amine ether (50EO-20PO) and 1mol of maleic anhydride as raw materials into an experimental device provided with a stirrer, a thermometer, a water separator and a condenser, inerting the whole experimental device for 3 times, introducing nitrogen for protection, starting a condenser, reacting the raw materials at 80-110 ℃ for 3-10 hours under normal pressure, cooling the raw materials by using circulating water, measuring the acid value below 100, and entering the next step; b. c, condensation polymerization reaction, namely, continuously adding 1mol of ethylene glycol, 0.9mol of succinic acid and a catalyst of p-toluenesulfonic acid into the reaction container in the step a, keeping introducing nitrogen by taking dimethylbenzene as a water-carrying agent, heating to 105-125 ℃ for reaction, separating water by using a water separator in the reaction process, reacting for 3 hours, adding 0.05mol of monoester generated in the step a, continuously reacting until the acid value is less than 50, and finishing the polycondensation reaction; c. b, performing double esterification, namely continuously adding 0.15mol of monoester generated in the step a into the reaction container in the step b, simultaneously heating to 130-185 ℃, keeping the nitrogen protection until the acid value is less than 5, cooling the polycondensation product to 50 +/-30 ℃ after the double esterification is finished, neutralizing the polycondensation product by using 32% NaOH solution until the pH value is 7 +/-0.5, and entering the next step; and d, sulfonation reaction, namely adding the double esterification product and 50% solution of 0.11mol of sodium metabisulfite into an experimental device provided with a condenser and a thermometer, heating to 85-115 ℃ in an oil bath under stirring, preserving heat, violently stirring, and reacting for 10-20 hours to obtain the product. And adding sodium hydroxide solution into the product, adjusting the pH value to 5-7, bleaching with hydrogen peroxide, and adjusting the solid content to the required solid content with ethanol.
Preparation of example 4-1
Preparation of an oligomeric sulfosuccinate surfactant of formula VII
Figure GDA0002483913350000212
A method for preparing an oligomeric sulfosuccinate surfactant of formula VII, comprising the steps of: a. performing a mono-esterification reaction, namely putting 0.82mol of isomeric bis-13 secondary amine ether (50EO-20PO) and 1mol of maleic anhydride as raw materials into an experimental device provided with a stirrer, a thermometer, a water separator and a condenser, inerting the whole experimental device for 3 times, introducing nitrogen for protection, starting a condenser, reacting the raw materials at 80-110 ℃ for 3-10 hours under normal pressure, cooling the raw materials by using circulating water, measuring the acid value below 100, and entering the next step; b. c, condensation polymerization reaction, namely, continuously adding 1mol of ethylene glycol, 0.9mol of succinic acid and a catalyst of p-toluenesulfonic acid into the reaction container in the step a, keeping introducing nitrogen by taking dimethylbenzene as a water-carrying agent, heating to 105-125 ℃ for reaction, separating water by using a water separator in the reaction process, reacting for 3 hours, adding 0.05mol of monoester generated in the step a, continuously reacting until the acid value is less than 50, and finishing the polycondensation reaction; c. b, performing double esterification, namely continuously adding 0.15mol of monoester generated in the step a into the reaction container in the step b, simultaneously heating to 130-185 ℃, keeping the nitrogen protection until the acid value is less than 5, cooling the polycondensation product to 50 +/-30 ℃ after the double esterification is finished, neutralizing the polycondensation product by using 32% NaOH solution until the pH value is 7 +/-0.5, and entering the next step; and d, sulfonation reaction, namely adding the double esterification product and 50% solution of 0.11mol of sodium metabisulfite into an experimental device provided with a condenser and a thermometer, heating to 85-115 ℃ in an oil bath under stirring, preserving heat, violently stirring, and reacting for 10-20 hours to obtain the product. And adding sodium hydroxide solution into the product, adjusting the pH value to 5-7, bleaching with hydrogen peroxide, and adjusting the solid content to the required solid content with ethanol.
Preparation of examples 4 to 2
Preparation of an oligomeric sulfosuccinate surfactant of formula VII
Figure GDA0002483913350000221
A method for preparing an oligomeric sulfosuccinate surfactant of formula VII, comprising the steps of: a. performing a mono-esterification reaction, namely putting 1.1mol of isomeric bis-13 secondary amine ether (50EO-20PO) and 1mol of maleic anhydride as raw materials into an experimental device provided with a stirrer, a thermometer, a water separator and a condenser, inerting the whole experimental device for 3 times, introducing nitrogen for protection, starting a condenser, reacting the raw materials at 80-110 ℃ for 3-10 hours under normal pressure, cooling the raw materials by using circulating water, measuring the acid value below 100, and entering the next step; b. c, condensation polymerization reaction, namely, continuously adding 1mol of ethylene glycol, 0.9mol of succinic acid and a catalyst of p-toluenesulfonic acid into the reaction container in the step a, keeping introducing nitrogen by taking dimethylbenzene as a water-carrying agent, heating to 105-125 ℃ for reaction, separating water by using a water separator in the reaction process, reacting for 3 hours, adding 0.05mol of monoester generated in the step a, continuously reacting until the acid value is less than 50, and finishing the polycondensation reaction; c. b, performing double esterification, namely continuously adding 0.15mol of monoester generated in the step a into the reaction container in the step b, simultaneously heating to 130-185 ℃, keeping the nitrogen protection until the acid value is less than 5, cooling the polycondensation product to 50 +/-30 ℃ after the double esterification is finished, neutralizing the polycondensation product by using 32% NaOH solution until the pH value is 7 +/-0.5, and entering the next step; and d, sulfonation reaction, namely adding the double esterification product and 50% solution of 0.11mol of sodium metabisulfite into an experimental device provided with a condenser and a thermometer, heating to 85-115 ℃ in an oil bath under stirring, preserving heat, violently stirring, and reacting for 10-20 hours to obtain the product. And adding sodium hydroxide solution into the product, adjusting the pH value to 5-7, bleaching with hydrogen peroxide, and adjusting the solid content to the required solid content with ethanol.
Preparation examples 4 to 3
Preparation of an oligomeric sulfosuccinate surfactant of formula VII
Figure GDA0002483913350000222
A method for preparing an oligomeric sulfosuccinate surfactant of formula VII, comprising the steps of: a. performing a mono-esterification reaction, namely putting 1.3mol of isomeric bis-13 secondary amine ether (50EO-20PO) and 1mol of maleic anhydride as raw materials into an experimental device provided with a stirrer, a thermometer, a water separator and a condenser, inerting the whole experimental device for 3 times, introducing nitrogen for protection, starting a condenser, reacting the raw materials at 80-110 ℃ for 3-10 hours under normal pressure, cooling the raw materials by using circulating water, measuring the acid value below 100, and entering the next step; b. c, condensation polymerization reaction, namely, continuously adding 1mol of ethylene glycol, 0.9mol of succinic acid and a catalyst of p-toluenesulfonic acid into the reaction container in the step a, keeping introducing nitrogen by taking dimethylbenzene as a water-carrying agent, heating to 105-125 ℃ for reaction, separating water by using a water separator in the reaction process, reacting for 3 hours, adding 0.05mol of monoester generated in the step a, continuously reacting until the acid value is less than 50, and finishing the polycondensation reaction; c. b, performing double esterification, namely continuously adding 0.15mol of monoester generated in the step a into the reaction container in the step b, simultaneously heating to 130-185 ℃, keeping the nitrogen protection until the acid value is less than 5, cooling the polycondensation product to 50 +/-30 ℃ after the double esterification is finished, neutralizing the polycondensation product by using 32% NaOH solution until the pH value is 7 +/-0.5, and entering the next step; and d, sulfonation reaction, namely adding the double esterification product and 50% solution of 0.11mol of sodium metabisulfite into an experimental device provided with a condenser and a thermometer, heating to 85-115 ℃ in an oil bath under stirring, preserving heat, violently stirring, and reacting for 10-20 hours to obtain the product. And adding sodium hydroxide solution into the product, adjusting the pH value to 5-7, bleaching with hydrogen peroxide, and adjusting the solid content to the required solid content with ethanol.
Preparation examples 4 to 4
Preparation of an oligomeric sulfosuccinate surfactant of formula VII
Figure GDA0002483913350000231
A method for preparing an oligomeric sulfosuccinate surfactant of formula VII, comprising the steps of: a. performing a mono-esterification reaction, namely putting 1.2mol of isomeric bis-13 secondary amine ether (50EO-20PO) and 1mol of maleic anhydride as raw materials into an experimental device provided with a stirrer, a thermometer, a water separator and a condenser, inerting the whole experimental device for 3 times, introducing nitrogen for protection, starting a condenser, reacting the raw materials at 80-110 ℃ for 3-10 hours under normal pressure, cooling the raw materials by using circulating water, measuring the acid value below 100, and entering the next step; b. c, condensation polymerization reaction, namely, continuously adding 1mol of ethylene glycol, 0.8mol of succinic acid and a catalyst of p-toluenesulfonic acid into the reaction container in the step a, keeping introducing nitrogen by taking dimethylbenzene as a water-carrying agent, heating to 105-125 ℃ for reaction, separating water by using a water separator in the reaction process, reacting for 3 hours, adding 0.05mol of monoester generated in the step a, continuously reacting until the acid value is less than 50, and finishing the polycondensation reaction; c. b, performing double esterification, namely continuously adding 0.15mol of monoester generated in the step a into the reaction container in the step b, simultaneously heating to 130-185 ℃, keeping the nitrogen protection until the acid value is less than 5, cooling the polycondensation product to 50 +/-30 ℃ after the double esterification is finished, neutralizing the polycondensation product by using 32% NaOH solution until the pH value is 7 +/-0.5, and entering the next step; and d, sulfonation reaction, namely adding the double esterification product and 50% solution of 0.11mol of sodium metabisulfite into an experimental device provided with a condenser and a thermometer, heating to 85-115 ℃ in an oil bath under stirring, preserving heat, violently stirring, and reacting for 10-20 hours to obtain the product. And adding sodium hydroxide solution into the product, adjusting the pH value to 5-7, bleaching with hydrogen peroxide, and adjusting the solid content to the required solid content with ethanol.
Preparation examples 4 to 5
Preparation of an oligomeric sulfosuccinate surfactant of formula VII
Figure GDA0002483913350000241
A method for preparing an oligomeric sulfosuccinate surfactant of formula VII, comprising the steps of: a. performing a mono-esterification reaction, namely putting 1.2mol of isomeric bis-13 secondary amine ether (50EO-20PO) and 1mol of maleic anhydride as raw materials into an experimental device provided with a stirrer, a thermometer, a water separator and a condenser, inerting the whole experimental device for 3 times, introducing nitrogen for protection, starting a condenser, reacting the raw materials at 80-110 ℃ for 3-10 hours under normal pressure, cooling the raw materials by using circulating water, measuring the acid value below 100, and entering the next step; b. c, condensation polymerization reaction, namely, continuously adding 1mol of ethylene glycol, 0.85mol of succinic acid and a catalyst of p-toluenesulfonic acid into the reaction container in the step a, keeping introducing nitrogen by taking dimethylbenzene as a water-carrying agent, heating to 105-125 ℃ for reaction, separating water by using a water separator in the reaction process, reacting for 3 hours, adding 0.05mol of monoester generated in the step a, continuously reacting until the acid value is less than 50, and finishing the polycondensation reaction; c. b, performing double esterification, namely continuously adding 0.15mol of monoester generated in the step a into the reaction container in the step b, simultaneously heating to 130-185 ℃, keeping the nitrogen protection until the acid value is less than 5, cooling the polycondensation product to 50 +/-30 ℃ after the double esterification is finished, neutralizing the polycondensation product by using 32% NaOH solution until the pH value is 7 +/-0.5, and entering the next step; and d, sulfonation reaction, namely adding the double esterification product and 50% solution of 0.11mol of sodium metabisulfite into an experimental device provided with a condenser and a thermometer, heating to 85-115 ℃ in an oil bath under stirring, preserving heat, violently stirring, and reacting for 10-20 hours to obtain the product. And adding sodium hydroxide solution into the product, adjusting the pH value to 5-7, bleaching with hydrogen peroxide, and adjusting the solid content to the required solid content with ethanol.
Preparation examples 4 to 6
Preparation of an oligomeric sulfosuccinate surfactant of formula VII
Figure GDA0002483913350000242
A method for preparing an oligomeric sulfosuccinate surfactant of formula VII, comprising the steps of: a. performing a mono-esterification reaction, namely putting 1.2mol of isomeric bis-13 secondary amine ether (50EO-20PO) and 1mol of maleic anhydride as raw materials into an experimental device provided with a stirrer, a thermometer, a water separator and a condenser, inerting the whole experimental device for 3 times, introducing nitrogen for protection, starting a condenser, reacting the raw materials at 80-110 ℃ for 3-10 hours under normal pressure, cooling the raw materials by using circulating water, measuring the acid value below 100, and entering the next step; b. c, condensation polymerization reaction, namely, continuously adding 1mol of ethylene glycol, 0.95mol of succinic acid and a catalyst of p-toluenesulfonic acid into the reaction container in the step a, keeping introducing nitrogen by taking dimethylbenzene as a water-carrying agent, heating to 105-125 ℃ for reaction, separating water by using a water separator in the reaction process, reacting for 3 hours, adding 0.05mol of monoester generated in the step a, continuously reacting until the acid value is less than 50, and finishing the polycondensation reaction; c. b, performing double esterification, namely continuously adding 0.15mol of monoester generated in the step a into the reaction container in the step b, simultaneously heating to 130-185 ℃, keeping the nitrogen protection until the acid value is less than 5, cooling the polycondensation product to 50 +/-30 ℃ after the double esterification is finished, neutralizing the polycondensation product by using 32% NaOH solution until the pH value is 7 +/-0.5, and entering the next step; and d, sulfonation reaction, namely adding the double esterification product and 50% solution of 0.11mol of sodium metabisulfite into an experimental device provided with a condenser and a thermometer, heating to 85-115 ℃ in an oil bath under stirring, preserving heat, violently stirring, and reacting for 10-20 hours to obtain the product. And adding sodium hydroxide solution into the product, adjusting the pH value to 5-7, bleaching with hydrogen peroxide, and adjusting the solid content to the required solid content with ethanol.
Preparation examples 4 to 7
Preparation of an oligomeric sulfosuccinate surfactant of formula VII
Figure GDA0002483913350000251
A method for preparing an oligomeric sulfosuccinate surfactant of formula VII, comprising the steps of: a. performing a mono-esterification reaction, namely putting 1.2mol of isomeric bis-13 secondary amine ether (50EO-20PO) and 1mol of maleic anhydride as raw materials into an experimental device provided with a stirrer, a thermometer, a water separator and a condenser, inerting the whole experimental device for 3 times, introducing nitrogen for protection, starting a condenser, reacting the raw materials at 80-110 ℃ for 3-10 hours under normal pressure, cooling the raw materials by using circulating water, measuring the acid value below 100, and entering the next step; b. c, condensation polymerization reaction, namely, continuously adding 1mol of ethylene glycol, 0.9mol of succinic acid and a catalyst of p-toluenesulfonic acid into the reaction container in the step a, keeping introducing nitrogen by taking dimethylbenzene as a water-carrying agent, heating to 105-125 ℃ for reaction, separating water by using a water separator in the reaction process, reacting for 3 hours, adding 0.05mol of monoester generated in the step a, continuously reacting until the acid value is less than 50, and finishing the polycondensation reaction; c. b, performing double esterification, namely continuously adding 0.1mol of monoester generated in the step a into the reaction container in the step b, simultaneously heating to 130-185 ℃, keeping the nitrogen protection until the acid value is less than 5, cooling the polycondensation product to 50 +/-30 ℃ after the double esterification is finished, neutralizing the polycondensation product by using 32% NaOH solution until the pH value is 7 +/-0.5, and entering the next step; and d, sulfonation reaction, namely adding the double esterification product and 50% solution of 0.11mol of sodium metabisulfite into an experimental device provided with a condenser and a thermometer, heating to 85-115 ℃ in an oil bath under stirring, preserving heat, violently stirring, and reacting for 10-20 hours to obtain the product. And adding sodium hydroxide solution into the product, adjusting the pH value to 5-7, bleaching with hydrogen peroxide, and adjusting the solid content to the required solid content with ethanol.
Preparation examples 4 to 8
Preparation of an oligomeric sulfosuccinate surfactant of formula VII
Figure GDA0002483913350000252
A method for preparing an oligomeric sulfosuccinate surfactant of formula VII, comprising the steps of: a. performing a mono-esterification reaction, namely putting 1.2mol of isomeric bis-13 secondary amine ether (50EO-20PO) and 1mol of maleic anhydride as raw materials into an experimental device provided with a stirrer, a thermometer, a water separator and a condenser, inerting the whole experimental device for 3 times, introducing nitrogen for protection, starting a condenser, reacting the raw materials at 80-110 ℃ for 3-10 hours under normal pressure, cooling the raw materials by using circulating water, measuring the acid value below 100, and entering the next step; b. c, condensation polymerization reaction, namely, continuously adding 1mol of ethylene glycol, 0.9mol of succinic acid and a catalyst of p-toluenesulfonic acid into the reaction container in the step a, keeping introducing nitrogen by taking dimethylbenzene as a water-carrying agent, heating to 105-125 ℃ for reaction, separating water by using a water separator in the reaction process, reacting for 3 hours, adding 0.05mol of monoester generated in the step a, continuously reacting until the acid value is less than 50, and finishing the polycondensation reaction; c. b, performing double esterification, namely continuously adding 0.4mol of monoester generated in the step a into the reaction container in the step b, simultaneously heating to 130-185 ℃, keeping the nitrogen protection until the acid value is less than 5, cooling the polycondensation product to 50 +/-30 ℃ after the double esterification is finished, neutralizing the polycondensation product by using 32% NaOH solution until the pH value is 7 +/-0.5, and entering the next step; and d, sulfonation reaction, namely adding the double esterification product and 50% solution of 0.11mol of sodium metabisulfite into an experimental device provided with a condenser and a thermometer, heating to 85-115 ℃ in an oil bath under stirring, preserving heat, violently stirring, and reacting for 10-20 hours to obtain the product. And adding sodium hydroxide solution into the product, adjusting the pH value to 5-7, bleaching with hydrogen peroxide, and adjusting the solid content to the required solid content with ethanol.
Test example 1
The performance ratios of wettability of the pressure-sensitive adhesive emulsions prepared from the samples prepared in preparation example 1, preparation examples 1-1 to 1-6, preparation example 2 and preparation examples 2-1 to 2-7 with respect to the pressure-sensitive adhesive emulsion as a control sample are shown in Table 2. The formulation of the original pressure sensitive adhesive emulsion is shown in table 1 below.
TABLE 1
Serial number Sample name Dosage (parts)
1 n-Butyl Acrylate (BA) 50
2 (hydroxyethyl acrylate) HEA 1
3 (acrylic acid) AA 1
4 Initiator 0.3
5 Emulsifier 0.4
6 Defoaming agent 0.05
7 Wetting agent 0.1
The performance ratios of the wettabilities of the pressure-sensitive adhesive emulsions prepared using the samples (0.3 to 0.4 parts) prepared in preparation example 1, preparation examples 1-1 to 1-6, preparation example 2, and preparation examples 2-1 to 2-7 and the reference sample pressure-sensitive adhesive emulsion are shown in table 2, wherein the wettability of the pressure-sensitive adhesive emulsion is represented by the surface tension of the sample, and the smaller the surface tension, the better the wettability of the pressure-sensitive adhesive emulsion is represented.
TABLE 2
Figure GDA0002483913350000261
Figure GDA0002483913350000271
As can be seen from Table 2, the pressure-sensitive adhesive emulsions prepared from the samples (0.3-0.4 parts) prepared in the preparation examples and the reference sample all show more excellent wettability; in particular, the pressure-sensitive adhesive emulsion prepared by the samples prepared in preparation examples 1 and 2 shows remarkably excellent wettability; more particularly, the pressure sensitive adhesive emulsion formulated with the sample prepared in preparation example 1 exhibited the most remarkably excellent wettability.
Test example 2
The ratio of the emulsifying properties of the alcohol ether carboxylic acids of the samples prepared in preparative example 3, preparative examples 3-1 to 1-8, preparative example 4 and preparative examples 4-1 to 4-8 to the comparative sample is shown in Table 3.
And (3) testing the emulsifying power: 150SN is base oil, purified water of 5 wt%, 10 wt%, 15 wt% or 20 wt% of the base oil is added, and the prepared example sample or comparative sample of 5 wt% of the base oil is added, stirred for 10min, left for 1min, and the state of the resultant is observed:
completely uniform: the product is milk white and homogeneous;
incomplete homogenization: the resultant is milky white and homogeneous as a whole, but has a few impurities;
completely inhomogeneous: the product has obvious layering or soap precipitation.
TABLE 3
Figure GDA0002483913350000281
As can be seen from Table 2, when the other conditions are the same, the addition amount of each of the preparation examples and the comparative examples is 5% or 10%, a completely uniform product can be formed with the base oil; when the addition amount of each preparation example and the comparative sample is 15%, each preparation example can still form a completely uniform product with the base oil, but the comparative sample can only form an incompletely uniform product with the base oil; further, when the respective preparation examples and comparative examples were added in an amount of 20%, only the samples obtained in preparation example 3, preparation example 3-2, preparation example 3-3, preparation example 3-5, preparation example 4-2, preparation example 4-3 and preparation example 4-5 were able to form a completely uniform product with the base oil, while the remaining preparation examples were able to form a completely non-uniform product with the base oil, while the comparative examples formed a completely non-uniform product with the base oil, and thus it was seen that the samples obtained in the respective preparation examples exhibited relatively superior effects to those of the comparative examples, particularly, preparation example 3-2, preparation example 3-3, preparation example 3-5, The samples prepared in preparation example 4, preparation example 4-2, preparation example 4-3, and preparation example 4-5 showed remarkably excellent effects.

Claims (13)

1. An oligomeric sulfosuccinate surfactant having a general formula as shown in formula I or formula II:
Figure FDA0002483913340000011
wherein, EO: CH (CH)2CH2O PO：
Figure FDA0002483913340000012
R1Is C2～C22A straight or branched chain saturated hydrocarbon group; r2、R3、R4Are respectively C2～C22A linear or branched saturated hydrocarbon group, wherein R3And R4The same or different; r7、R8Is H or C1～C18A straight or branched chain saturated hydrocarbon group; the intermediate connecting group of the molecule in the formula I is a condensation polymerization product of dibasic acid or anhydride and dihydric alcohol; n is 5-50, a is 2-100, and b is 0-100, which are integers; the products obtained by mono-esterifying secondary amine ether and maleic anhydride are used as two ends of the formula I; m1Is selected from L i+、Na+、K+、NH4 +One or more of them.
2. The oligomeric sulfosuccinate surfactant of claim 1, wherein R is1Is C2～C4A straight or branched saturated hydrocarbon group, said R2Is C2～C4A straight or branched saturated hydrocarbon group, said R3Is C4～C13A straight or branched saturated hydrocarbon group, said R4Is C4～C13A straight or branched chain saturated hydrocarbon group; a is any integer of 2 to 50, and b is any integer of 0 to 20.
3. The oligomeric sulfosuccinate surfactant of claim 1, wherein,
the R is1Is C4A straight or branched saturated hydrocarbon group, said R2Is C4A straight or branched saturated hydrocarbon group, said R3Is C4A straight or branched saturated hydrocarbon group, said R4Is C4A straight or branched chain saturated hydrocarbon group, a is 2, b is 10; or
The R is1Is C4A straight or branched saturated hydrocarbon group, said R2Is C2A straight or branched saturated hydrocarbon group, said R3Is C8A straight or branched saturated hydrocarbon group, said R4Is C8A straight or branched chain saturated hydrocarbon group, a is 5, b is 10; or
The R is1Is C2A straight or branched saturated hydrocarbon group, said R2Is C2A straight or branched saturated hydrocarbon group, said R3Is C12A straight or branched saturated hydrocarbon group, said R4Is C12A straight or branched chain saturated hydrocarbon group, a is 5, b is 0; or
The R is1Is C4A straight or branched saturated hydrocarbon group, said R2Is C2A straight or branched saturated hydrocarbon group, said R3Is C13A straight or branched saturated hydrocarbon group, said R4Is C13A straight or branched chain saturated hydrocarbon group, a is 50, and b is 20.
4. A method of making an oligomeric sulfosuccinate surfactant, comprising the steps of:
a. carrying out a mono-esterification reaction on maleic anhydride and secondary amine ether;
b. the diacid or anhydride and the dihydric alcohol are subjected to condensation polymerization reaction under the action of a catalyst to generate an intermediate connecting group;
c. b, carrying out double esterification reaction on the mono-esterification product obtained in the step a and the polymerization product obtained in the step b; and
d. c reacting the diester obtained in step c with (M)1)2S2O5Carrying out conjugate addition sulfonation reaction to obtain a final product,
the specific reaction equation is as follows:
Figure FDA0002483913340000031
wherein, EO: CH (CH)2CH2O
Figure FDA0002483913340000032
R1Is C2～C22A straight or branched chain saturated hydrocarbon group; r2、R3、R4Are respectively C2～C22A linear or branched saturated hydrocarbon group, wherein R3、R4May be the same or different; the intermediate connecting group of the molecule in the formula I is a condensation polymerization product of dibasic acid or anhydride and dihydric alcohol; n is 5-50, a is 2-100, and b is 0-100, which are integers; the products obtained by mono-esterifying secondary amine ether and maleic anhydride are used as two ends of the formula I; m1Is selected from L i+、Na+、K+、NH4 +One or more of them.
5. The process according to claim 4, wherein, in the monoesterification of maleic anhydride with a secondary amine ether,
the molar ratio of the maleic anhydride to the secondary amine ether is 1: 0.82 to 1.30; the secondary amine ether is C4～C200Straight chain orBranched saturated hydrocarbyl secondary amine ethers.
6. The process according to claim 5, wherein, in the monoesterification of maleic anhydride with a secondary amine ether,
the molar ratio of the maleic anhydride to the secondary amine ether is 1: 1.10 to 1.30;
the secondary amine ether is C34～C186A saturated linear or branched alkane secondary amine ether of (a).
7. A process as in claim 5, wherein said secondary amine ether is a dibutyl secondary amine ether, a dioctyl secondary amine ether, a didodecyl secondary amine ether, an isomeric ditridecyl secondary amine ether, and a dioctadecyl secondary amine ether.
8. The method according to claim 4, wherein, in the condensation polymerization reaction,
the molar ratio of the dibasic acid or the anhydride to the dihydric alcohol is 0.8-0.95: 1; the catalyst is one or more of sulfuric acid, phosphoric acid, p-toluenesulfonic acid, hydrochloride and sulfate, and the mass of the catalyst is 0.2-5% of that of the maleic anhydride; adding a mono-esterification product for controlling the molecular weight of the polycondensation product, wherein the molar ratio of the mono-esterification product to the dihydric alcohol is 0.05-0.1: 1.
9. The method of claim 8, wherein, in the condensation polymerization reaction,
the molar ratio of the dibasic acid or the anhydride to the dihydric alcohol is 0.85-0.9: 1;
the catalyst is p-toluenesulfonic acid.
10. The process of claim 4, wherein, in the double esterification reaction,
the molar ratio of the added amount of the mono-esterification product to the dihydric alcohol is (0.15-0.45): 1, wherein the added amount of the mono-esterification product comprises the amount of the mono-esterification product added in the condensation polymerization reaction.
11. The process of claim 10, wherein, in the double esterification reaction,
the molar ratio of the added amount of the mono-esterification product to the dihydric alcohol is (0.2-0.3): 1, wherein the added amount of the mono-esterification product comprises the amount of the mono-esterification product added in the condensation polymerization reaction.
12. The process according to claim 4, wherein, in the sulfonation reaction,
the maleic anhydride and (M)1)2S2O5At a molar ratio of 1.00: 0.11 to 0.85; said (M)1)2S2O5Is selected from L i2S2O5、Na2S2O5、K2S2O5、(NH4)2S2O5One or more of (a).
13. The method of claim 12, wherein (M)1)2S2O5Is Na2S2O5。
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