CN111620995A - Preparation method of polyurethane for photocatalytic degradation of formaldehyde - Google Patents
Preparation method of polyurethane for photocatalytic degradation of formaldehyde Download PDFInfo
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- CN111620995A CN111620995A CN202010429969.6A CN202010429969A CN111620995A CN 111620995 A CN111620995 A CN 111620995A CN 202010429969 A CN202010429969 A CN 202010429969A CN 111620995 A CN111620995 A CN 111620995A
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- 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
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
- C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6674—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/34—Chemical or biological purification of waste gases
- B01D53/74—General processes for purification of waste gases; Apparatus or devices specially adapted therefor
- B01D53/86—Catalytic processes
- B01D53/8668—Removing organic compounds not provided for in B01D53/8603 - B01D53/8665
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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
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
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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
- C08G18/3203—Polyhydroxy compounds
- C08G18/3206—Polyhydroxy compounds aliphatic
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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
- C08G18/34—Carboxylic acids; Esters thereof with monohydroxyl compounds
- C08G18/348—Hydroxycarboxylic acids
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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
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4825—Polyethers containing two hydroxy groups
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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
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
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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
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
- C08G18/6692—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/34
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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
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K9/00—Use of pretreated ingredients
- C08K9/10—Encapsulated ingredients
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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
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
- C08K2003/2296—Oxides; Hydroxides of metals of zinc
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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
- C08K2201/00—Specific properties of additives
- C08K2201/011—Nanostructured additives
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- Environmental & Geological Engineering (AREA)
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- Polyurethanes Or Polyureas (AREA)
Abstract
The invention discloses a preparation method of polyurethane for photocatalytic degradation of formaldehyde, which comprises the steps of coating and modifying nano zinc oxide to increase the compatibility of the nano zinc oxide and the polyurethane, introducing an active group capable of reacting with the polyurethane, connecting the active group into a polyurethane structural unit through a chemical bond, and solving the problems of uneven dispersion and easy agglomeration of a nano inorganic material, so that the original excellent mechanical property, thermal stability and the like of the polyurethane are not damaged, and the problems of poor compatibility and poor migration resistance of the nano inorganic material and the polyurethane are solved, so that the polyurethane can be endowed with a stable and excellent photocatalytic degradation effect of formaldehyde, the synthesis process is easy to control, the performance is easy to adjust, and the preparation method can be widely applied to adhesives and building road coatings.
Description
Technical Field
The invention relates to the technical field of preparation of high polymer materials, in particular to a preparation method of polyurethane for photocatalytic degradation of formaldehyde.
Background
Formaldehyde, which is often used in building materials such as adhesives and coatings, is one of the recognized potential carcinogens in the world. The main harm of the indoor formaldehyde is the stimulation effect on the skin mucosa of a human body, the olfactory threshold of the human formaldehyde is 0.06-0.07 mg/m3, and the formaldehyde concentration of 0.15mg/m3 can cause uncomfortable symptoms such as cough, asthma, itching eyes, dry and itching throat, hoarseness, dry and itching skin, dermatitis and the like. The harm of formaldehyde to human bodies is so serious that how to effectively degrade the formaldehyde is more and more important to society.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides a preparation method of polyurethane for photocatalytic degradation of formaldehyde, which coats and modifies nano zinc oxide to increase the compatibility of the nano zinc oxide and the polyurethane, introduces active groups capable of reacting with the polyurethane, and connects the active groups with a polyurethane chain segment through chemical bonds, thereby endowing the polyurethane with good formaldehyde degradation performance and having little influence on the original good performance of the polyurethane.
In order to achieve the purpose, the invention provides a preparation method of polyurethane for photocatalytic degradation of formaldehyde, which comprises the following steps of (1) modifying nano zinc oxide, adding 15-25 parts of nano zinc oxide and 3-5 parts of triethoxysilane into a three-necked flask, heating, mechanically stirring, adding glacial acetic acid to adjust the pH value of a system to 4-6, reacting for a period of time at 60-70 ℃, stopping, washing with ammonia water and absolute ethyl alcohol for multiple times, drying a product until the quality of the product is not changed, and preparing modified nano zinc oxide;
preparing polyurethane for degrading formaldehyde through photocatalysis, namely adding polymer diol, diisocyanate, a micromolecule diol chain extender, modified nano zinc oxide and a catalyst which are dried in a vacuum oven at 120 ℃ and 0.1atm overnight into a reaction container, and heating to 65-85 ℃ for reaction for a period of time under the conditions of continuous stirring and nitrogen atmosphere protection to prepare a prepolymer; adding a hydrophilic chain extender dissolved by a solvent, and continuously reacting for a period of time at the temperature of 65-85 ℃; adding triethylamine to neutralize the prepolymer, adding deionized water under the action of high shear force, emulsifying at a high speed for 1h, and removing the solvent under reduced pressure for recycling to obtain polyurethane for photocatalytic degradation of formaldehyde; wherein the dosage ratio of the components is as follows: 5-10 parts of modified nano zinc oxide, 60-100 parts of polymer dihydric alcohol, 30-50 parts of diisocyanate, 2-5 parts of micromolecular dihydric alcohol chain extender, 0.01-0.2 part of catalyst, 5-20 parts of solvent, 5-7 parts of hydrophilic chain extender and 4-5 parts of triethylamine.
As a further configuration of the present invention, in the step (2), the polymer diol is any one or a combination of polypropylene glycol, polyethylene glycol or polytetrahydrofuran glycol with a number average molecular weight of 1000-2000.
As a further configuration of the present invention, in the step (2), the diisocyanate is any one of isophorone diisocyanate, 2, 4-toluene diisocyanate, 1, 6-hexyl diisocyanate, diphenylmethane diisocyanate, or 4,4' -dicyclohexylmethane diisocyanate.
As a further configuration of the present invention, in the step (2), the small molecule diol chain extender is any one of ethylene glycol, 1, 3-propanediol, 1, 4-butanediol, neopentyl glycol, 1, 6-hexanediol, or diethylene glycol.
As a further configuration of the present invention, in the step (2), the catalyst is any one of bismuth neodecanoate, bismuth laurate, bismuth isooctanoate, bismuth naphthenate, bis-dimethylamino ethyl ether, or dimethylcyclohexylamine.
As a further configuration of the present invention, in the step (2), the solvent is any one of acetone, butanone N, N-dimethylformamide, N-dimethylacetamide, or N-methylpyrrolidone.
As a further configuration of the present invention, in the step (2), the hydrophilic chain extender is any one of dimethylolpropionic acid or dimethylolbutyric acid.
The method has the advantages that the polyurethane has the advantages of excellent friction resistance, mechanical property, low-temperature flexibility and the like, is widely applied to adhesives and building road coatings, and can be widely applied, and the nano zinc oxide (ZnO) has the characteristics of wide forbidden band at room temperature (Eg 3.36eV), high electron mobility and the like, can be used as a photocatalyst, is combined with a light source with a specific wavelength, and degrades formaldehyde under the action of photocatalytic oxidation. The modified polyurethane can be added into polyurethane to endow the polyurethane with the function of degrading formaldehyde through photocatalysis, so that the modified polyurethane can be used in construction environment and can eliminate the formaldehyde. Wherein, the polymer dihydric alcohol which is over night is selected in the step (2), because the dihydric alcohol is easy to be mixed with water, the water has great influence on the next synthesis preparation, the polymer dihydric alcohol is put in a vacuum oven to pump water, the water is generally pumped for at least two hours, the polymer dihydric alcohol which is over night is used, the experiment is convenient, and the experiment efficiency is improved. Meanwhile, in the preparation process, the silane coupling agent is used for coating the nano zinc oxide, so that the compatibility of the nano zinc oxide with polyurethane is improved, and an active group capable of reacting with the polyurethane is introduced into the coating layer; the polyurethane for photocatalytic degradation of formaldehyde connects nano zinc oxide into a polyurethane structural unit through a chemical bond, solves the problems of poor compatibility, poor migration resistance, easy aggregation and the like of the existing blending compound nano inorganic material and polyurethane, and has stable and excellent photocatalytic degradation effect on formaldehyde. Solves the problems of uneven dispersion and easy agglomeration of the nano inorganic material, and the uniform dispersion and the chemical bond action do not damage the original excellent mechanical property, thermal stability and the like of the polyurethane.
Detailed Description
The first embodiment of the preparation method of polyurethane for photocatalytic degradation of formaldehyde comprises the following steps of (1) modifying nano zinc oxide, adding 15 parts of nano zinc oxide and 3 parts of triethoxysilane into a three-necked bottle, heating, mechanically stirring, adding glacial acetic acid to adjust the pH value of a system to 5, and stopping reaction at 60 ℃ for 7 hours; washing with ammonia water and absolute ethyl alcohol for multiple times, and drying the product until the mass of the product is not changed, thereby preparing the modified nano zinc oxide; adding 100 parts of polypropylene glycol with the average molecular weight of 2000, 50 parts of 4,4' -dicyclohexylmethane diisocyanate, 4 parts of 1, 4-butanediol, 10 parts of modified nano zinc oxide and 0.2 part of bismuth laurate catalyst which are dried overnight in a vacuum oven at 120 ℃ and 0.1atm into a reaction container, and heating to 85 ℃ for reaction for 2 hours under the conditions of continuous stirring and nitrogen atmosphere protection to prepare a prepolymer; adding 7 parts of dimethylolpropionic acid dissolved in N, N-dimethylformamide, and continuously reacting for 2 hours while maintaining the temperature at 85 ℃; and (3) adding 5 parts of triethylamine to neutralize the prepolymer, adding deionized water under the action of high shear force, and emulsifying at high speed for 1h to obtain the polyurethane for degrading formaldehyde by photocatalysis.
The second embodiment of the preparation method of polyurethane for photocatalytic degradation of formaldehyde comprises the following steps of (1) modifying nano zinc oxide, adding 25 parts of nano zinc oxide and 5 parts of triethoxysilane into a three-necked flask, heating, mechanically stirring, adding glacial acetic acid to adjust the pH value of the system to 6, and stopping reaction at 70 ℃ for 6 hours. And washing the zinc oxide powder with ammonia water and absolute ethyl alcohol for multiple times, and drying the product until the mass of the product is not changed, thereby preparing the modified nano zinc oxide. Adding 20 parts of polyethylene glycol with the average molecular weight of 2000, 40 parts of polytetrahydrofuran glycol with the average molecular weight of 1000, 30 parts of 2, 4-toluene diisocyanate, 2 parts of ethylene glycol, 5 parts of modified nano zinc oxide and 0.01 part of bismuth neodecanoate catalyst which are dried overnight in a vacuum oven at 120 ℃ and 0.1atm into a reaction container, and heating to 65 ℃ for reaction for 2 hours under the conditions of continuous stirring and nitrogen atmosphere protection to prepare a prepolymer; adding 5 parts of dimethylolbutyric acid dissolved in acetone, and continuously reacting for 3 hours at 65 ℃; and 4 parts of triethylamine is added to neutralize the prepolymer, deionized water is added under the action of high shear force, and high-speed emulsification is carried out for 1 hour, so that the polyurethane for degrading formaldehyde by photocatalysis is obtained.
The third embodiment of the preparation method of polyurethane for photocatalytic degradation of formaldehyde comprises the following steps of (1) modifying nano zinc oxide, adding 20 parts of nano zinc oxide and 4 parts of triethoxysilane into a three-necked flask, heating, mechanically stirring, adding glacial acetic acid to adjust the pH value of the system to 4, and stopping reaction at 65 ℃ for 6.5 hours. And washing the zinc oxide powder with ammonia water and absolute ethyl alcohol for multiple times, and drying the product until the mass of the product is not changed, thereby preparing the modified nano zinc oxide. Adding 80 parts of polytetrahydrofuran glycol with the average molecular weight of 2000, 40 parts of isophorone diisocyanate, 5 parts of diethylene glycol, 8 parts of modified nano zinc oxide and 0.1 part of dimethyl cyclohexylamine catalyst which are dried overnight in a vacuum oven at 120 ℃ and 0.1atm into a reaction container, and heating to 80 ℃ for reaction for 3 hours under the conditions of continuous stirring and nitrogen atmosphere protection to obtain a prepolymer; adding 6 parts of dimethylolbutyric acid dissolved in N, N-dimethylacetamide, and keeping at 80 ℃ to continue reacting for 2.5 h; and (3) adding 5 parts of triethylamine to neutralize the prepolymer, adding deionized water under the action of high shear force, and emulsifying at high speed for 1h to obtain the polyurethane for degrading formaldehyde by photocatalysis.
The above example is only one of the preferred embodiments of the present invention, and general changes and substitutions by those skilled in the art within the technical scope of the present invention are included in the protection scope of the present invention.
Claims (7)
1. A preparation method of polyurethane for photocatalytic degradation of formaldehyde is characterized by comprising the following steps: comprises the following steps of (a) carrying out,
modifying the nano zinc oxide in the step (1), namely adding 15-25 parts of nano zinc oxide and 3-5 parts of triethoxysilane into a three-necked bottle, heating, mechanically stirring, adding glacial acetic acid to adjust the pH value of a system to 4-6, reacting for a period of time at 60-70 ℃, stopping, washing with ammonia water and absolute ethyl alcohol for multiple times, and drying the product until the quality does not change, thus obtaining the modified nano zinc oxide;
preparing polyurethane for degrading formaldehyde through photocatalysis, namely adding polymer diol, diisocyanate, a micromolecule diol chain extender, modified nano zinc oxide and a catalyst which are dried in a vacuum oven at 120 ℃ and 0.1atm overnight into a reaction container, and heating to 65-85 ℃ for reaction for a period of time under the conditions of continuous stirring and nitrogen atmosphere protection to prepare a prepolymer; adding a hydrophilic chain extender dissolved by a solvent, and continuously reacting for a period of time at the temperature of 65-85 ℃; adding triethylamine to neutralize the prepolymer, adding deionized water under the action of high shear force, emulsifying at a high speed for 1h, and removing the solvent under reduced pressure for recycling to obtain polyurethane for photocatalytic degradation of formaldehyde; wherein the dosage ratio of the components is as follows: 5-10 parts of modified nano zinc oxide, 60-100 parts of polymer dihydric alcohol, 30-50 parts of diisocyanate, 2-5 parts of micromolecular dihydric alcohol chain extender, 0.01-0.2 part of catalyst, 5-20 parts of solvent, 5-7 parts of hydrophilic chain extender and 4-5 parts of triethylamine.
2. The method for preparing polyurethane for photocatalytic degradation of formaldehyde according to claim 1, characterized in that: in the step (2), the polymer diol is any one or combination of polypropylene glycol, polyethylene glycol or polytetrahydrofuran glycol with the number average molecular weight of 1000-.
3. The method for preparing polyurethane for photocatalytic degradation of formaldehyde according to claim 1, characterized in that: in the step (2), the diisocyanate is any one of isophorone diisocyanate, 2, 4-toluene diisocyanate, 1, 6-hexyl diisocyanate, diphenylmethane diisocyanate or 4,4' -dicyclohexylmethane diisocyanate.
4. The method for preparing polyurethane for photocatalytic degradation of formaldehyde according to claim 1, characterized in that: in the step (2), the micromolecular diol chain extender is any one of ethylene glycol, 1, 3-propylene glycol, 1, 4-butanediol, neopentyl glycol, 1, 6-hexanediol or diethylene glycol.
5. The method for preparing polyurethane for photocatalytic degradation of formaldehyde according to claim 1, characterized in that: in the step (2), the catalyst is any one of bismuth neodecanoate, bismuth laurate, bismuth isooctanoate, bismuth naphthenate, bis-dimethylamino ethyl ether or dimethyl cyclohexylamine.
6. The method for preparing polyurethane for photocatalytic degradation of formaldehyde according to claim 1, characterized in that: in the step (2), the solvent is any one of acetone, butanone N, N-dimethylformamide, N-dimethylacetamide and N-methylpyrrolidone.
7. The method for preparing polyurethane for photocatalytic degradation of formaldehyde according to claim 1, characterized in that: in the step (2), the hydrophilic chain extender is any one of dimethylolpropionic acid or dimethylolbutyric acid.
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| CN202010429969.6A CN111620995A (en) | 2020-05-20 | 2020-05-20 | Preparation method of polyurethane for photocatalytic degradation of formaldehyde |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112048962A (en) * | 2020-09-27 | 2020-12-08 | 深圳市嘉达高科产业发展有限公司 | Permeable concrete road capable of purifying automobile exhaust and construction method thereof |
| CN112574381A (en) * | 2020-12-08 | 2021-03-30 | 兴业皮革科技股份有限公司 | Formaldehyde scavenging agent for tanning and preparation method thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111040426A (en) * | 2019-12-27 | 2020-04-21 | 安徽匠星联创新材料科技有限公司 | Nano zinc oxide modified waterborne polyurethane emulsion and preparation method thereof |
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- 2020-05-20 CN CN202010429969.6A patent/CN111620995A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111040426A (en) * | 2019-12-27 | 2020-04-21 | 安徽匠星联创新材料科技有限公司 | Nano zinc oxide modified waterborne polyurethane emulsion and preparation method thereof |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112048962A (en) * | 2020-09-27 | 2020-12-08 | 深圳市嘉达高科产业发展有限公司 | Permeable concrete road capable of purifying automobile exhaust and construction method thereof |
| CN112574381A (en) * | 2020-12-08 | 2021-03-30 | 兴业皮革科技股份有限公司 | Formaldehyde scavenging agent for tanning and preparation method thereof |
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