CN112480461A - Preparation method and application of modified foaming polyurethane - Google Patents
Preparation method and application of modified foaming polyurethane Download PDFInfo
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- CN112480461A CN112480461A CN202011347613.4A CN202011347613A CN112480461A CN 112480461 A CN112480461 A CN 112480461A CN 202011347613 A CN202011347613 A CN 202011347613A CN 112480461 A CN112480461 A CN 112480461A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/009—Use of pretreated compounding ingredients
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F3/00—Biological treatment of water, waste water, or sewage
- C02F3/28—Anaerobic digestion processes
- C02F3/2806—Anaerobic processes using solid supports for microorganisms
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3225—Polyamines
- C08G18/3237—Polyamines aromatic
- C08G18/3243—Polyamines aromatic containing two or more aromatic rings
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2101/00—Nature of the contaminant
- C02F2101/10—Inorganic compounds
- C02F2101/16—Nitrogen compounds, e.g. ammonia
- C02F2101/163—Nitrates
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2101/00—Nature of the contaminant
- C02F2101/30—Organic compounds
- C02F2101/38—Organic compounds containing nitrogen
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
- C08J2375/04—Polyurethanes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/02—Elements
- C08K3/04—Carbon
- C08K3/041—Carbon nanotubes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K9/00—Use of pretreated ingredients
- C08K9/04—Ingredients treated with organic substances
Abstract
The invention belongs to the technical field of sewage treatment, and particularly relates to a preparation method and application of modified foaming polyurethane.
Description
Technical Field
The invention belongs to the technical field of sewage treatment, and relates to a preparation method and application of modified foamed polyurethane.
Background
Azo dyes and nitrates have become one of the important pollution sources of water pollution. Three major degradation methods, chemical, physical and microbiological, have been developed, with the microbiological having the best application prospects. The oxidation-reduction mediator mainly containing anthraquinone compounds has a good promoting effect on the degradation of azo dyes and nitrates by anaerobic microorganisms, and can increase the degradation rate by 1 to several orders of magnitude. There is still a need for more research to improve the practical application effect.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provides a preparation method of modified foaming polyurethane.
The invention also aims to provide application of the modified foaming polyurethane, which has better effect on sewage treatment containing azo dyes and nitrates.
The technical scheme of the invention is as follows:
a preparation method of modified foaming polyurethane comprises the following steps,
s1, dispersing the carboxylated carbon nanotubes in an organic solvent, adding a carboxyl activating agent and an amino anthraquinone-containing compound, heating to 50-100 ℃, reacting for 8-48 hours, adding polyamine, and continuing to react for 1-24 hours to obtain modified carbon nanotubes;
s2, adding the modified carbon nano tube obtained in the step S1 in the preparation process of the foamed polyurethane according to 0.05-5% of the total weight of all the raw materials of the foamed polyurethane, and preparing to obtain the modified foamed polyurethane.
In the technical scheme of the invention, the organic solvent is selected from the species which do not participate in the reaction, and includes but is not limited to tetrahydrofuran, acetone, butyl acetate, ethyl acetate, 1, 4-dioxane, methyl ethyl ketone, cyclohexanone, ethylene glycol dimethyl ether and propylene glycol dimethyl ether.
In the technical scheme of the invention, the preparation process of the foaming polyurethane is a method disclosed in the prior art, and the used raw materials comprise isocyanate, polyalcohol and/or polyamine, a foaming agent and the like.
In the technical scheme of the invention, the modified carbon nanotube obtained in the step S1 is added to participate in the reaction with isocyanate, and can be added into the reaction system before the foaming agent is added, or can be added into the reaction system together with the foaming agent.
Preferably, the carboxyl activating agent in step S1 is at least one selected from the group consisting of N, N '-Dicyclohexylcarbodiimide (DCC), N-hydroxysuccinimide (NHS), 4-Dimethylaminopyridine (DMAP), N' -Diisopropylcarbodiimide (DIC), N-hydroxythiosuccinimide (sulfo-NHS), and 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDC), and the weight of the carboxyl activating agent is 10 to 50% of the weight of the carboxylated carbon nanotube.
Preferably, the amino anthraquinone-containing compound in step S1 is at least one selected from the group consisting of 1-amino-2-bromo-4-hydroxyanthraquinone, 2-aminoanthraquinone, 1, 2-diaminoanthraquinone, 1, 4-diaminoanthraquinone, 2, 6-diaminoanthraquinone, 1, 8-diaminoanthraquinone, 1, 5-diaminoanthraquinone, 1-amino-2-methylanthraquinone, 1, 5-dihydroxy-4, 8-diaminoanthraquinone and 1-aminoanthraquinone.
Preferably, the polyamine in step S1 has at least 2 primary amino groups in the molecule.
More preferably, the polyamine is at least one selected from the group consisting of ethylenediamine, 1, 2-propylenediamine, 1, 3-propylenediamine, divinyltriamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, hexaethyleneheptamine, 1, 4-butanediamine, 1, 5-pentanediamine, and 1, 6-hexanediamine.
Preferably, the ratio of the mole number of carboxyl groups in the carboxylated carbon nanotube to the sum of the mole number of primary amine in the amino-containing anthraquinone compound and the mole number of primary amine in the polyamine in the step S1 is 1 (0.8-1).
Preferably, the ratio of the mole number of the primary amine in the amino anthraquinone-containing compound to the mole number of the primary amine in the polyamine in the step S1 is (1-9): (9-1).
Preferably, in the step S2, the modified carbon nanotubes obtained in the step S1 are added in an amount of 0.2 to 2% by weight of the total weight of the raw materials of the polyurethane foam.
A modified foamed polyurethane prepared by the preparation method of any one of the above embodiments.
The modified foaming polyurethane of the embodiment is used for treating sewage, in particular to treat sewage containing azo dyes and nitrate.
The invention has the beneficial effects that:
(1) the invention adopts amidation reaction of carboxyl and amino to graft amino-containing anthraquinone compound and polyamine on the surface of the carbon nano tube respectively, so as to obtain the modified carbon nano tube with anthraquinone and primary amino.
(2) According to the invention, the modified carbon nano tube is added in the preparation process of the foaming polyurethane, the primary amino group on the carbon nano tube reacts with isocyanate to participate in the condensation reaction of the polyurethane, so that the carbon nano tube is grafted to the side chain of a polyurethane polymer, anthraquinone and the carbon nano tube can be stably dispersed in a polyurethane film, and the better effect of promoting the degradation of azo dyes and nitrates by anaerobic microorganisms is synergistically exerted.
(3) The foaming polyurethane has larger specific surface area due to the existence of the foam holes, so that the contact area of anthraquinone and sewage is increased, and the foaming polyurethane has better effect on promoting the degradation of azo dyes and nitrates by anaerobic microorganisms.
Detailed Description
The technical solution of the present invention is further illustrated and described by the following detailed description.
Unless otherwise specified, the parts described in the following examples are parts by weight.
Examples 1 to 4 preparation of modified carbon nanotubes
Example 1
Selecting raw materials, namely carboxyl activating agents DCC and NHS, wherein the weight of DCC is 10% of that of the carboxylated carbon nanotube, and the weight of NHS is 10% of that of the carboxylated carbon nanotube; the amino anthraquinone-containing compound is 1-amino anthraquinone, and the carboxyl molar ratio of the amino anthraquinone compound to the carboxylated carbon nanotube is 0.5: 1; the polyamine is triethylene tetramine, and the carboxyl molar ratio of the triethylene tetramine to the carboxylated carbon nanotube is 0.6: 1;
dispersing 1 part of carboxylated carbon nanotube into 500 parts of tetrahydrofuran, adding NHS, DCC and 1-aminoanthraquinone, heating until the reaction system undergoes micro reflux reaction for 20 hours, adding triethylene tetramine, continuing the reaction for 8 hours, filtering out solids, cleaning and drying to obtain the modified carbon nanotube 1.
Example 2
Selecting raw materials, namely carboxyl activating agents EDC and DMAP, wherein the weight of EDC is 20% of that of the carboxylated carbon nanotube, and the weight of DMAP is 15% of that of the carboxylated carbon nanotube; the amino anthraquinone-containing compound is 2-amino anthraquinone, and the carboxyl molar ratio of the amino anthraquinone compound to the carboxylated carbon nanotube is 0.6: 1; the polyamine is tetraethylenepentamine, and the carboxyl molar ratio of the tetraethylenepentamine to the carboxylated carbon nano tube is 0.5: 1;
dispersing 1 part of carboxylated carbon nanotube into 500 parts of butyl acetate, adding EDC, DMAP and 2-aminoanthraquinone, heating to 70 ℃ for reacting for 15 hours, adding tetraethylenepentamine, continuing to react for 12 hours, filtering out solid, washing and drying to obtain the modified carbon nanotube 2.
Example 3
Selecting raw materials, namely carboxyl activating agents DCC and NHS, wherein the weight of DCC is 15% of that of the carboxylated carbon nanotube, and the weight of NHS is 15% of that of the carboxylated carbon nanotube; the amino anthraquinone-containing compound is 1, 4-diaminoanthraquinone, and the carboxyl molar ratio of the amino anthraquinone-containing compound to the carboxylated carbon nanotube is 0.2: 1; the polyamine is 1, 6-hexamethylene diamine, and the carboxyl molar ratio of the polyamine to the carboxylated carbon nanotube is 0.7: 1;
dispersing 1 part of carboxylated carbon nanotube in 500 parts of tetrahydrofuran, adding NHS (N-hydroxysuccinimide), DCC (DCC) and 1, 4-diaminoanthraquinone, heating until the reaction system undergoes micro-reflux reaction for 14 hours, adding 1, 6-hexamethylenediamine, continuing the reaction for 6 hours, filtering out solid, washing and drying to obtain the modified carbon nanotube 3.
Example 4
Selecting raw materials, carboxyl activating agents EDC and NHS, wherein the weight of EDC is 20% of that of the carboxylated carbon nanotube, and the weight of NHS is 10% of that of the carboxylated carbon nanotube; the amino anthraquinone-containing compound is 1-amino-2-methylanthraquinone, and the carboxyl molar ratio of the amino anthraquinone-containing compound to the carboxylated carbon nanotube is 0.8: 1; the polyamine is 1, 4-butanediamine, and the carboxyl molar ratio of the polyamine to the carboxylated carbon nanotube is 0.4: 1;
dispersing 1 part of carboxylated carbon nanotube into 500 parts of tetrahydrofuran, adding EDC, NHS and 1-amino-2-methylanthraquinone, heating to a reaction system for micro-reflux reaction for 10 hours, adding 1, 4-butanediamine, continuing the reaction for 14 hours, filtering out solids, cleaning and drying to obtain the modified carbon nanotube 4.
Examples 5 to 10 preparation of modified foamed polyurethane
Example 5
65 parts of a prepolymer containing a terminal isocyanate group, which is obtained by reacting 65 parts of polyethylene glycol having an average relative molecular mass of 3500 with 35 parts of 3,3 '-dimethylbiphenyl-4, 4' -diisocyanate, adding a foaming agent comprising a mixture of 3 parts of water, 3 parts of 1, 6-hexanediol, 1.2 parts of polyether silicone oil, 0.1 part of an amine catalyst A1, 12 parts of ethylene glycol adipate polyester glycol having an average relative molecular mass of 1100 and 0.08 part of a modified carbon nanotube 1 under stirring, carrying out a foaming reaction at 50 to 60 ℃, and carrying out a crosslinking reaction at 120 ℃ for 4 hours to obtain a modified foamed polyurethane, which is denoted as P-1.
Example 6
Adding 50 parts of polyether 305, 50 parts of polyether 600, 4 parts of foaming catalyst AM-1, 1 part of foaming catalyst A33, 0.3 part of foaming agent T12, 6 parts of water, 0.7 part of modified carbon nano tube 2 and 3 parts of 25mPa.s silicone oil with viscosity (25 ℃) into a container, uniformly stirring, adding 120 parts of polymethylene polyphenyl polyisocyanate PAPI, uniformly stirring, pouring the feed liquid into a mold, curing for 120 minutes at 20-25 ℃ and curing for 3 hours at 30 ℃ to obtain the modified foaming polyurethane, wherein the mark is P-2.
Example 7
70 parts of ethylene glycol adipate glycol with the average relative molecular mass of 3500, 10 parts of AEO-10, 1 part of polyether silicone oil, 1.9 parts of pore-opening agent KF-28, 5 parts of foaming catalyst AM-1, 2.2 parts of modified carbon nano tube 3 and 2 parts of foaming catalyst A33 are mixed to form the component B.
The component A is polymethylene polyphenyl isocyanate.
The component A and the component B are uniformly mixed according to the weight ratio of 1:1, and foaming is carried out at 62 ℃ to obtain modified foaming polyurethane, which is marked as P-3.
Example 8
40 parts of polyethylene glycol with the average relative molecular mass of 4200, 4 parts of water, 0.2 part of dibutyltin dilaurate, 0.6 part of polyether silicone oil surfactant and 4.5 parts of modified carbon nanotube 4 are uniformly mixed, 25 parts of toluene diisocyanate are added, the mixture is rapidly stirred for 3 seconds and poured into a prepared mold, and the mixture is cured at 20-25 ℃ for 120 minutes and cured at 30 ℃ for 3 hours to obtain modified foamed polyurethane, which is marked as P-4.
Example 9
55 parts of polyethylene glycol with average relative molecular mass of 2200, 65 parts of polycaprolactone diol with average relative molecular mass of 1500, 180 parts of toluene diisocyanate, 3 parts of epoxidized soybean oil, 5 parts of propylene glycol, 0.2 part of polysiloxane-oxyalkylene block copolymer, 1 part of water, 1.2 parts of triethyldiamine and 1.5 parts of modified carbon nanotube 1,
mixing polyethylene glycol and polycaprolactone diol, carrying out vacuum dehydration, heating to melt, adding epoxidized soybean oil, propylene glycol, polysiloxane-oxyalkylene block copolymer, triethyldiamine and modified carbon nano tube 1, stirring for 15min at the rotating speed of 1000r/min, treating for 5min at 0.2Mpa, adding a foaming agent storage tank, adding water and toluene diisocyanate into a foaming machine respectively, foaming by using a high-pressure foaming machine, keeping the temperature of a mould at 65 ℃, and forming to obtain foamed polyurethane, which is marked as P-5.
Example 10
According to the raw materials, 100 parts of polyethylene glycol with the average relative molecular mass of 2200, 50 parts of isocyanate TDI, 2.5 parts of 1, 4-butanediol, 12 parts of thermal expansion foaming microsphere EHM303, 0.3 part of stannous octoate, 3 parts of dibenzoyl peroxide, 2 parts of accelerant M, 0.3 part of modified carbon nano tube 2,
and (2) uniformly mixing the dried polyethylene glycol, TDI and 1, 4-butanediol, reacting for 3-6 hours under the catalysis of stannous octoate, adding the modified carbon nanotube 2, stirring for reacting for 2 hours, adding the thermal expansion foaming microsphere EHM303, dibenzoyl peroxide and an accelerator M, uniformly mixing, and vulcanizing and foaming to obtain the foaming polyurethane, which is marked as P-6.
Comparative example 1
In example 9, 1.5 parts of the modified carbon nanotube 1 was changed to 1.2 parts of the carbon nanotube, and the remainder was unchanged to obtain a foamed polyurethane, which was designated as P-7.
Comparative example 2
In example 9, 1.5 parts of modified carbon nanotube 1 was changed to 0.3 part of 1-aminoanthraquinone, and the remainder was not changed to obtain a foamed polyurethane, which was designated as P-8.
Comparative example 3
In example 9, 1.5 parts of modified carbon nanotube 1 was changed to 1.2 parts of carbon nanotube and 0.3 part of 1-aminoanthraquinone, and the remainder was unchanged to obtain a polyurethane foam, which was designated as P-9.
Performance testing
And (3) testing the degradation acceleration effect of the azo dye: after 2g of samples to be tested are respectively washed by physiological saline for 3 times, the samples are added into 200ml of 120mg/L direct scarlet 4B containing azo dye degradation strains GYZ (staphylococcus sp.) in logarithmic growth phase for decolorization test, and the change of the concentration of the direct scarlet 4B along with time is measured. The results are shown in Table 1.
TABLE 1 direct scarlet 4B concentration as a function of time in mg/L
Nitrate degradation acceleration effect test: after 2g of samples to be tested are respectively washed by physiological saline for 3 times, the samples are added into 200ml of 150mg/L sodium nitrate wastewater containing denitrifying microorganisms in logarithmic phase for testing, and the change of the concentration of the sodium nitrate along with the time is measured. The results are shown in Table 2.
TABLE 2 nitrate concentration as a function of time in mg/L
And (3) stability testing: after 2g of samples to be tested are respectively washed for 3 times by physiological saline, the samples are added into 200ml of 120mg/L direct scarlet 4B containing azo dye degradation strains GYZ (staphylococcus sp.) in logarithmic growth phase for decolorization test, and the concentration of the direct scarlet 4B after 6 hours is determined. And cleaning and drying a sample to be tested by using clear water and absolute ethyl alcohol, and then performing a decolorization test for 6 hours by using direct scarlet 4B according to the method, and repeating the test for 12 times. The results are shown in Table 3.
TABLE 3 direct scarlet 4B concentration mg/L
In conclusion, the modified foaming polyurethane can effectively promote anaerobic microorganisms to degrade azo dyes and nitrates, and has a good application prospect in treatment of sewage containing the azo dyes and the nitrates.
The foregoing has shown and described the fundamental principles, principal features and advantages of the invention. It should be understood by those skilled in the art that the present invention is not limited by the foregoing embodiments, which are merely preferred embodiments of the present invention, and the scope of the present invention should not be limited thereby, and that equivalent changes and modifications made within the scope of the present invention and the specification should be covered thereby. The scope of the invention is defined by the appended claims and equivalents thereof.
Claims (10)
1. A preparation method of modified foaming polyurethane is characterized by comprising the following steps,
s1, dispersing the carboxylated carbon nanotubes in an organic solvent, adding a carboxyl activating agent and an amino anthraquinone-containing compound, heating to 50-100 ℃, reacting for 8-48 hours, adding polyamine, and continuing to react for 1-24 hours to obtain modified carbon nanotubes;
s2, adding the modified carbon nano tube obtained in the step S1 in the preparation process of the foamed polyurethane according to 0.05-5% of the total weight of all the raw materials of the foamed polyurethane, and preparing to obtain the modified foamed polyurethane.
2. The method according to claim 1, wherein the carboxyl activating agent in step S1 is at least one selected from the group consisting of N, N '-dicyclohexylcarbodiimide, N-hydroxysuccinimide, 4-dimethylaminopyridine, N' -diisopropylcarbodiimide, N-hydroxythiosuccinimide and 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride, and the weight of the carboxyl activating agent is 10 to 50% of the weight of the carboxylated carbon nanotube.
3. The production method according to claim 1, wherein the aminoanthraquinone-containing compound in step S1 is at least one selected from the group consisting of 1-amino-2-bromo-4-hydroxyanthraquinone, 2-aminoanthraquinone, 1, 2-diaminoanthraquinone, 1, 4-diaminoanthraquinone, 2, 6-diaminoanthraquinone, 1, 8-diaminoanthraquinone, 1, 5-diaminoanthraquinone, 1-amino-2-methylanthraquinone, 1, 5-dihydroxy-4, 8-diaminoanthraquinone and 1-aminoanthraquinone.
4. The method according to claim 1, wherein the polyamine has at least 2 primary amino groups in its molecule in step S1.
5. The production method according to claim 4, wherein the polyamine is at least one selected from the group consisting of ethylenediamine, 1, 2-propylenediamine, 1, 3-propylenediamine, divinyltriamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, hexaethyleneheptamine, 1, 4-butylenediamine, 1, 5-pentylenediamine, and 1, 6-hexylenediamine.
6. The method according to claim 1, wherein the ratio of the number of moles of carboxyl groups in the carboxylated carbon nanotubes to the sum of the number of moles of primary amine in the aminoanthraquinone-containing compound and the number of moles of primary amine in the polyamine in step S1 is 1 (0.8-1).
7. The method according to claim 1, wherein the ratio of the number of moles of the primary amine in the aminoanthraquinone-containing compound to the number of moles of the primary amine in the polyamine in step S1 is (1-9): (9-1).
8. The method of claim 1, wherein the modified carbon nanotubes obtained in step S1 are added in step S2 in an amount of 0.2-2% by weight based on the total weight of the raw materials of the polyurethane foam.
9. A modified foamed polyurethane obtained by the production method according to any one of claims 1 to 8.
10. Use of the modified foamed polyurethane according to claim 9 for the treatment of sewage.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115340169A (en) * | 2022-08-19 | 2022-11-15 | 广东工业大学 | Method for treating soil leaching waste liquid by catalyzing monopersulfate through modified activated carbon |
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