CN115260893A - Self-repairing UV (ultraviolet) photocuring antifogging resin polymer and preparation method thereof - Google Patents
Self-repairing UV (ultraviolet) photocuring antifogging resin polymer and preparation method thereof Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- C09D175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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Abstract
The invention discloses a self-repairing UV (ultraviolet) photocuring antifogging resin polymer and a preparation method thereof, and relates to the technical field of antifogging coatings. The self-repairing coating is prepared by using a synthetic resin A with a self-repairing effect and a hydrophilic antifogging synthetic resin B as raw materials, wherein the resin A is a route of firstly synthesizing a polyurethane prepolymer and then grafting acrylic ester, and the resin A has a large molecular weight, good flexibility and a self-repairing effect; the resin B is a route of firstly synthesizing the alcohol sulfonic acid resin prepolymer and then grafting the acrylic ester, and has stronger hydrophilicity and antifogging function. The invention further enhances the hydrophilicity and the antifogging effect of the resin polymer system by adding the dioctyl sodium sulfosuccinate.
Description
Technical Field
The invention belongs to the technical field of antifogging coatings, and particularly relates to a self-repairing UV (ultraviolet) photocuring antifogging resin polymer and a preparation method thereof.
Background
In real life, the glass and plastic products are easy to have the phenomena of fogging and frosting, for example, window glass in winter, automobile windshield glass, bathroom glass, vinyl house and the like, a certain temperature difference often appears on two sides separated from each other, the saturated vapor pressure of surface moisture with low temperature is lower than the vapor pressure of the surrounding environment, so that the water vapor is gathered to the surface of an object, the mist is formed by analyzing in a micro water droplet form, and each small water droplet can refract and reflect light, the light transmittance of a transparent material is obviously reduced, and the sight line is influenced. If the temperature of one side is too low, even frost can be formed, which causes inconvenience to production and life and even causes great loss.
In order to solve such problems, the simplest treatment method is to spray "soapy water" (surfactant) on the surface of glass and plastic products, which can exert an antifogging effect in a short time (typically several hours). Another method is to coat the surface of glass and plastic products with water-based antifogging coating or UV-cured antifogging coating, which can achieve the antifogging effect of several days to several months. Wherein the core of the UV light-cured antifogging coating is UV light-cured antifogging resin.
The main problems of the current UV light curing antifogging resins, such as CN 108219063B, CN 105504144B, CN 103881434B, CN 111849333B, and the like, are still poor antifogging effect, and the antifogging coating is easy to scratch during wiping, i.e. poor wear resistance, and has no self-repairing function.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides a self-repairing UV light-cured antifogging resin polymer and a preparation method thereof.
The invention is realized by adopting the following technical scheme:
the self-repairing UV photocuring antifogging resin polymer comprises the following raw materials in parts by weight:
the solvent is ethyl acetate, butyl acetate, isopropanol or propylene glycol methyl ether acetate;
the preparation method of the resin A comprises the following steps:
s1, putting 100 parts by weight of polyol into a reaction kettle, heating to 120 ℃, carrying out vacuum dehydration for 1-2 h, cooling to 75-83 ℃, adding aliphatic isocyanate, wherein the molar ratio of hydroxyl of the polyol to isocyanate in the aliphatic isocyanate is 1.05, and stirring for reaction for 3-4 h to obtain an isocyanate-terminated polyurethane prepolymer;
s2, adding monohydroxy acrylate into the isocyanate-terminated polyurethane prepolymer, wherein the molar ratio of the monohydroxy acrylate to the aliphatic isocyanate is 0.1;
the preparation method of the resin B comprises the following steps:
(1) Under the protection of inert gas, mixing micromolecular polyol and benzenesulfonic acid in a molar ratio of 1:2 in a reaction kettle, and stirring at normal temperature;
(2) Dropwise adding a catalyst accounting for 1-3% of the total mass of reactants into a reaction kettle, wherein the catalyst needs to be prepared into a catalyst solution with the mass concentration of 1% before dropwise adding, and the catalyst is tetrabutyl titanate; the dripping time is 15-30 min, the temperature is raised to 130-180 ℃ after the dripping is finished, a condensation reflux device is started, and the mixture is stirred and reacts for 6-8 h to prepare the alcohol sulfonic acid resin prepolymer containing hydroxyl and alkyl phenyl;
(3) Adding isocyanate acrylate monomer, adding the isocyanate acrylate monomer and the alcoholic sulfonic acid resin prepolymer containing hydroxyl and alkyl phenyl according to the molar ratio of hydroxyl 1:1, controlling the reaction temperature to be 75-85 ℃, then dropwise adding organic tin catalyst solution with the mass concentration of 0.05% and polymerization inhibitor solution with the mass concentration of 1%, wherein the molar ratio of the organic tin catalyst to isocyanate in the isocyanate acrylate monomer is 0.06-0.12%, the molar ratio of the polymerization inhibitor to acrylic double bonds in the isocyanate acrylate monomer is 0.1-0.3%, the dropwise adding time of the catalyst solution and the polymerization inhibitor solution is 1-2 h, and reacting for 3-4 h after the dropwise adding is finished to obtain the resin B.
Preferably, the polyol in step S1 is one of polytrimethylene ether glycol (selected from SK chemical ecoroll H2000 in korea) and modified castor oil polyol (selected from petroleum polyols D2000), and the polyol has a molecular weight of 2000.
Preferably, the aliphatic isocyanate in step S1 includes at least one of Hexamethylene Diisocyanate (HDI), isophorone diisocyanate (IPDI), dicyclohexylmethane diisocyanate (HMDI), cyclohexanedimethylene diisocyanate (HXDI), and methylcyclohexyl diisocyanate (HTDI). The aliphatic isocyanate has good yellowing resistance and flexibility, and is beneficial to realizing a self-repairing function.
Preferably, the monohydroxy acrylate in step S2 is at least one of hydroxypropyl acrylate (HPA), hydroxypropyl methacrylate (HPMA), 4-hydroxybutyl acrylate (4 HBA), and hydroxybutyl methacrylate (HBMA). The hydroxyl of the monohydroxy acrylate has higher reactivity and is beneficial to reacting with residual isocyanic acid radical; and the glass transition temperature of the selected monohydroxy acrylate is lower, so that the whole resin is softer, and the self-repairing function is realized.
Preferably, the catalyst in step S2 is dibutyltin dilaurate, the catalyst solution is prepared by dissolving dibutyltin dilaurate in a solvent, and the solvent is one or more of ethyl acetate, toluene, butyl acetate, butanone, ethylene glycol ethyl ether acetate, propylene glycol methyl ether acetate, methyl isobutyl ketone, and cyclohexanone.
Preferably, the small molecule polyol in step (1) is one of ethylene glycol, glycerol, trimethylolpropane, trimethylolethane and pentaerythritol; the benzene sulfonic acid is one of dodecyl benzene sulfonic acid and p-methyl benzene sulfonic acid.
Preferably, the solvent used in the catalyst solution in step (2) is one or more of ethyl acetate, toluene, butyl acetate, butanone, methyl isobutyl ketone and N-methylpyrrolidone.
Preferably, the isocyanate acrylate monomer in step (3) is isocyanate ethyl acrylate or isocyanate ethyl methacrylate.
Preferably, the polymerization inhibitor in the step (3) is p-hydroxyanisole and hydroquinone, and the solvent of the polymerization inhibitor solution is one or more of ethyl acetate, toluene, butyl acetate, butanone, methyl isobutyl ketone and N-methylpyrrolidone.
The preparation method of the self-repairing UV photocuring antifogging resin polymer comprises the steps of uniformly stirring the resin A, the resin B, the dioctyl sodium sulfosuccinate and the solvent in the proportion in a reaction kettle at normal temperature for 30-60 min, filtering (with a 200-mesh sieve), discharging and packaging.
Compared with the prior art, the invention has the following beneficial effects:
the UV photocuring antifogging resin polymer is prepared by taking a self-repairing synthetic resin A and a hydrophilic antifogging resin B as raw materials, wherein the self-repairing synthetic resin A is a route of firstly synthesizing a polyurethane prepolymer and then grafting acrylic ester, and the resin A has the advantages of large molecular weight, good flexibility and self-repairing effect; the resin B is a route of firstly synthesizing the alcohol sulfonic acid resin prepolymer and then grafting the acrylic ester, and has stronger hydrophilicity and antifogging function. The invention further enhances the hydrophilicity and the antifogging effect of the resin system by adding the dioctyl sodium sulfosuccinate.
Detailed Description
The present invention will be further described with reference to the following specific examples.
Example 1
A preparation method of a self-repairing UV photocuring antifogging resin polymer comprises the following steps:
firstly, weighing the following raw materials in parts by weight:
secondly, mixing the weighed raw materials in a reaction kettle, stirring uniformly at normal temperature for 30min, filtering (200-mesh sieve), discharging and packaging.
The preparation method of the resin A comprises the following steps:
s1, putting 100 parts by weight of polyol into a reaction kettle, heating to 120 ℃, carrying out vacuum dehydration for 1.5h, cooling to 80 ℃, adding aliphatic isocyanate, wherein the molar ratio of hydroxyl of the polyol to isocyanate in the aliphatic isocyanate is 1.05, and stirring for reaction for 3-4 h to obtain an isocyanate-terminated polyurethane prepolymer;
s2, adding monohydroxy acrylate into the isocyanate-terminated polyurethane prepolymer, wherein the molar ratio of the monohydroxy acrylate to the aliphatic isocyanate is 0.1;
the polyol in step S1 is polytrimethylene ether glycol, which has a molecular weight of 2000.
Wherein the aliphatic isocyanate in the step S1 is Hexamethylene Diisocyanate (HDI).
Wherein the monohydroxy acrylate in step S2 is hydroxypropyl acrylate (HPA).
Wherein, in the step S2, the catalyst is dibutyltin dilaurate, and the catalyst solution is prepared by dissolving dibutyltin dilaurate in ethyl acetate.
The preparation method of the resin B comprises the following steps:
(1) Under the protection of inert gas, mixing micromolecular polyol and benzenesulfonic acid in a molar ratio of 1:2 in a reaction kettle, and stirring at normal temperature;
(2) Dropwise adding a catalyst accounting for 2% of the total mass of reactants into a reaction kettle, wherein a catalyst solution with the mass concentration of 1% needs to be prepared before dropwise adding, and the catalyst is tetrabutyl titanate; the dripping time is 20min, the temperature is raised to 150 ℃ after the dripping is finished, a condensation reflux device is started, and the mixture is stirred and reacts for 7h to prepare the alcoholic sulfonic acid resin prepolymer containing hydroxyl and alkyl phenyl;
(3) And adding an isocyanate acrylate monomer, wherein the adding amount of the isocyanate acrylate monomer and the alcoholic sulfonic acid resin prepolymer containing hydroxyl and alkyl phenyl are added according to a hydroxyl molar ratio of 1:1, controlling the reaction temperature to be 80 ℃, dropwise adding a dibutyltin dilaurate catalyst solution (solvent is butanone) with the mass concentration of 0.05% and a polymerization inhibitor solution with the mass concentration of 1%, wherein the molar ratio of the dibutyltin dilaurate catalyst to isocyanate in the isocyanate acrylate monomer is 0.1%, the molar ratio of the polymerization inhibitor to acrylic double bonds in the isocyanate acrylate monomer is 0.2%, the dropwise adding time of the catalyst solution and the polymerization inhibitor solution is 1.5h, and reacting for 3.5h after dropwise adding is finished to obtain the resin B.
Wherein, the micromolecular polyalcohol in the step (1) is glycol; the benzene sulfonic acid is dodecyl benzene sulfonic acid.
Wherein, the solvent adopted in the catalyst solution in the step (2) is butanone.
Wherein, the isocyanate acrylate monomer in the step (3) is isocyanate ethyl acrylate.
And (3) the polymerization inhibitor is p-hydroxyanisole, and the solvent of the polymerization inhibitor solution is butanone.
Example 2
A preparation method of a self-repairing UV light-cured antifogging resin polymer comprises the following steps:
firstly, weighing the following raw materials in parts by weight:
secondly, mixing the weighed raw materials in a reaction kettle, stirring uniformly at normal temperature for 60min, filtering (200-mesh sieve), discharging and packaging.
The preparation method of the resin A comprises the following steps:
s1, putting 100 parts by weight of polyol into a reaction kettle, heating to 120 ℃, carrying out vacuum dehydration for 2 hours, cooling to 83 ℃, adding aliphatic isocyanate, wherein the molar ratio of hydroxyl of the polyol to isocyanate in the aliphatic isocyanate is 1.05, and carrying out stirring reaction for 3 hours to obtain an isocyanate-terminated polyurethane prepolymer;
s2, adding monohydroxy acrylate into the isocyanate-terminated polyurethane prepolymer, wherein the molar ratio of the monohydroxy acrylate to the aliphatic isocyanate is 0.1;
in step S1, the polyol is modified castor oil polyol (Vanderella Polycins D2000) and has a molecular weight of 2000.
Wherein the aliphatic isocyanate in the step S1 is isophorone diisocyanate (IPDI).
Wherein the monohydroxy acrylate in step S2 is hydroxypropyl methacrylate (HPMA).
The catalyst in the step S2 is dibutyltin dilaurate, the catalyst solution is prepared by dissolving dibutyltin dilaurate in a solvent, and the solvent is butanone.
The preparation method of the resin B comprises the following steps:
(1) Under the protection of inert gas, mixing micromolecular polyol and benzenesulfonic acid in a molar ratio of 1:2 in a reaction kettle, and stirring at normal temperature;
(2) Dropwise adding a catalyst accounting for 1% of the total mass of reactants into a reaction kettle, wherein a catalyst solution with the mass concentration of 1% needs to be prepared before dropwise adding, and the catalyst is tetrabutyl titanate; the dripping time is 25min, the temperature is raised to 130 ℃ after the dripping is finished, a condensation reflux device is started, and the mixture is stirred and reacts for 8h to prepare the alcoho-sulfonic acid resin prepolymer containing hydroxyl and alkyl phenyl;
(3) And adding an isocyanate acrylate monomer, wherein the adding amount of the isocyanate acrylate monomer and the alcoholic sulfonic acid resin prepolymer containing hydroxyl and alkyl phenyl are added according to a hydroxyl molar ratio of 1:1, controlling the reaction temperature to be 75 ℃, dropwise adding a dibutyltin dilaurate catalyst solution (the solvent is toluene) with the mass concentration of 0.05% and a polymerization inhibitor solution with the mass concentration of 1%, wherein the molar ratio of the dibutyltin dilaurate catalyst to the isocyanate in the isocyanate acrylate monomer is 0.06%, the molar ratio of the polymerization inhibitor to the acrylic double bonds in the isocyanate acrylate monomer is 0.1%, and the dropwise adding time of the catalyst solution and the polymerization inhibitor solution is 1h, and reacting for 4h after the dropwise adding is finished to obtain the resin B.
Wherein, the small molecular polyol in the step (1) is glycerol; the benzenesulfonic acid is p-toluenesulfonic acid.
Wherein, the solvent adopted in the catalyst solution in the step (2) is toluene.
Wherein, the isocyanate acrylate monomer in the step (3) is isocyanate ethyl acrylate or isocyanate ethyl methacrylate.
And (3) the polymerization inhibitor is hydroquinone, and the solvent of the polymerization inhibitor solution is toluene.
Comparative example 1
The preparation method of the UV photocuring antifogging resin polymer comprises the following steps:
firstly, weighing the following raw materials in parts by weight:
resin A100 parts
10 portions of dioctyl sodium sulfosuccinate
40 parts of isopropanol;
secondly, mixing the weighed raw materials in a reaction kettle, stirring uniformly at normal temperature for 30min, filtering (200-mesh sieve), discharging and packaging.
The preparation of resin A is described in example 1.
Comparative example 2
The preparation method of the UV photocuring antifogging resin polymer comprises the following steps:
firstly, weighing the following raw materials in parts by weight:
resin B30 parts
10 portions of dioctyl sodium sulfosuccinate
40 parts of isopropanol;
secondly, mixing the weighed raw materials in a reaction kettle, stirring uniformly at normal temperature for 30min, filtering (200-mesh sieve), discharging and packaging.
The preparation of resin B is described in example 1.
Comparative example 3
The preparation method of the UV photocuring antifogging resin polymer comprises the following steps:
firstly, weighing the following raw materials in parts by weight:
resin A100 parts
Resin B30 parts
40 parts of isopropanol;
secondly, mixing the weighed raw materials in a reaction kettle, stirring uniformly at normal temperature for 30min, filtering (200-mesh sieve), discharging and packaging.
The preparation methods of resin a and resin B are as in example 1.
To the UV photocurable anti-fog resin polymers prepared in examples 1-2 and comparative examples 1-3, 10% by mass of trimethylolpropane triacrylate (TMPTA), 10% by mass of isobornyl acrylate (IBOA), 1% by mass of photoinitiator 184, 2% by mass of photoinitiator TPO were added, followed by dilution with isopropyl alcohol to prepare a coating.
Coating the above coating on 50 μm thick PET film with wire rod, controlling dry weight to 5 μm, oven drying at 120 deg.C for 2min to volatilize solvent, and irradiating with UV light source with wavelength of 280-395nm with illumination energy of 300-600mj/cm 2 So that the coating is completely cured to obtain the functional film. The functional films were tested, and the specific test results are shown in table 1.
TABLE 1
The antifogging effect test method is that the film is flatly placed 10cm above a boiling kettle, so that the coating surface is contacted with water vapor, and the water vapor can not be condensed into water mist on the film when the water vapor is seen within 10 s.
The antifogging durability test method comprises the following steps: the film was wiped dry with a paper towel and the above operation was repeated to see how many times the film had no anti-fogging effect.
The self-repairing speed refers to a test method in an optical functional film self-repairing hardening film' HG/T5675-2020.
As can be seen from the test results, when the antifogging resin polymer does not contain the resin B (comparative example 1), transparency and adhesion are reduced, water contact angle is increased, hydrophilicity is reduced, and antifogging durability is remarkably deteriorated; when the antifogging resin polymer does not contain the resin A (comparative example 2), the transparency and the adhesive force are reduced, the self-repairing performance is obviously deteriorated, and the antifogging durability is also reduced; when the anti-fog resin polymer does not contain dioctyl sodium sulfosuccinate (comparative example 3), the water contact angle is increased, the hydrophilicity is reduced, and the anti-fog durability is also reduced.
It should be noted that the above-mentioned embodiments are merely examples of the present invention, and it is obvious that the present invention is not limited to the above-mentioned embodiments, and other modifications are possible. All modifications directly or indirectly obvious to one skilled in the art from the present disclosure are to be considered within the scope of the present invention.
Claims (10)
1. The self-repairing UV photocuring antifogging resin polymer is characterized by comprising the following raw materials in parts by weight:
the solvent is ethyl acetate, butyl acetate, isopropanol or propylene glycol methyl ether acetate;
the preparation method of the resin A comprises the following steps:
s1, putting 100 parts by weight of polyol into a reaction kettle, heating to 120 ℃, carrying out vacuum dehydration for 1-2 h, cooling to 75-83 ℃, adding aliphatic isocyanate, wherein the molar ratio of hydroxyl of the polyol to isocyanate in the aliphatic isocyanate is 1.05, and stirring for reaction for 3-4 h to obtain an isocyanate-terminated polyurethane prepolymer;
s2, adding monohydroxy acrylate into the isocyanate-terminated polyurethane prepolymer, wherein the molar ratio of the monohydroxy acrylate to the aliphatic isocyanate is 0.1;
the preparation method of the resin B comprises the following steps:
(1) Under the protection of inert gas, mixing micromolecular polyol and benzenesulfonic acid in a molar ratio of 1:2 in a reaction kettle, and stirring at normal temperature;
(2) Dropwise adding a catalyst accounting for 1-3% of the total mass of reactants into a reaction kettle, wherein the catalyst needs to be prepared into a catalyst solution with the mass concentration of 1% before dropwise adding, and the catalyst is tetrabutyl titanate; the dripping time is 15-30 min, the temperature is raised to 130-180 ℃ after the dripping is finished, a condensation reflux device is started, and the mixture is stirred and reacts for 6-8 h to prepare the alcohol sulfonic acid resin prepolymer containing hydroxyl and alkyl phenyl;
(3) Adding isocyanate acrylate monomer, adding the isocyanate acrylate monomer and the alcoholic sulfonic acid resin prepolymer containing hydroxyl and alkyl phenyl according to the molar ratio of hydroxyl 1:1, controlling the reaction temperature to be 75-85 ℃, then dropwise adding organic tin catalyst solution with the mass concentration of 0.05% and polymerization inhibitor solution with the mass concentration of 1%, wherein the molar ratio of the organic tin catalyst to isocyanate in the isocyanate acrylate monomer is 0.06-0.12%, the molar ratio of the polymerization inhibitor to acrylic double bonds in the isocyanate acrylate monomer is 0.1-0.3%, the dropwise adding time of the catalyst solution and the polymerization inhibitor solution is 1-2 h, and reacting for 3-4 h after dropwise adding is finished to obtain the resin B.
2. The self-repairing UV light-cured antifog resin polymer of claim 1, wherein in step S1, the polyol is one of polytrimethylene ether glycol and modified castor oil polyol, and the molecular weight of the polyol is 2000.
3. The self-repairing UV light-cured antifog resin polymer of claim 1, wherein the aliphatic isocyanate of step S1 comprises at least one of hexamethylene diisocyanate, isophorone diisocyanate, dicyclohexylmethane diisocyanate, cyclohexane dimethylene diisocyanate, and methylcyclohexyl diisocyanate.
4. The self-repairing UV light-cured antifog resin polymer of claim 1, wherein the monohydroxy acrylate in step S2 is at least one of hydroxypropyl acrylate, hydroxypropyl methacrylate, 4-hydroxybutyl acrylate and hydroxybutyl methacrylate.
5. The self-repairing UV light-curing antifogging resin polymer as claimed in claim 1, wherein in step S2, the catalyst is dibutyltin dilaurate, the catalyst solution is prepared by dissolving dibutyltin dilaurate in a solvent, and the solvent is one or more of ethyl acetate, toluene, butyl acetate, butanone, ethylene glycol ethyl ether acetate, propylene glycol methyl ether acetate, methyl isobutyl ketone and cyclohexanone.
6. The self-repairing UV light-cured antifog resin polymer of claim 1, wherein the small molecule polyol of step (1) is one of ethylene glycol, glycerol, trimethylolpropane, trimethylolethane, pentaerythritol; the benzene sulfonic acid is one of dodecyl benzene sulfonic acid and p-methyl benzene sulfonic acid.
7. The self-repairing UV light-cured antifogging resin polymer of claim 1, wherein a solvent adopted in the catalyst solution of step (2) is one or more of ethyl acetate, toluene, butyl acetate, butanone, methyl isobutyl ketone and N-methylpyrrolidone.
8. The self-repairing UV light-curing antifog resin polymer of claim 1, wherein the isocyanate acrylate monomer of step (3) is isocyanate ethyl acrylate or isocyanate ethyl methacrylate.
9. The self-repairing UV light-curing antifogging resin polymer as claimed in claim 1, wherein the polymerization inhibitor in step (3) is p-hydroxyanisole or hydroquinone.
10. The preparation method of the self-repairing UV light-cured antifogging resin polymer according to any one of claims 1 to 9, characterized in that: and uniformly stirring the resin A, the resin B, the dioctyl sodium sulfosuccinate and the solvent in the ratio in a reaction kettle at normal temperature for 30-60 min, filtering, discharging and packaging.
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