CN113388321B - Perovskite anchoring fluorine-containing zwitterion polyurethane luminescent antifouling coating and preparation method thereof - Google Patents
Perovskite anchoring fluorine-containing zwitterion polyurethane luminescent antifouling coating and preparation method thereof Download PDFInfo
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- CN113388321B CN113388321B CN202110710421.3A CN202110710421A CN113388321B CN 113388321 B CN113388321 B CN 113388321B CN 202110710421 A CN202110710421 A CN 202110710421A CN 113388321 B CN113388321 B CN 113388321B
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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
- C09D175/08—Polyurethanes from polyethers
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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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/22—Luminous paints
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Abstract
The invention discloses a perovskite anchoring fluorine-containing zwitter-ion polyurethane luminescent antifouling coating and a preparation method thereof, belonging to the field of marine antifouling coatings; the preparation method comprises the following steps: preparing a precursor cesium oleate; step two: preparing perovskite; step three: dispersing the perovskite in methanol, dropwise adding 1-thioglycerol under stirring, and reacting for 12-13 hours to obtain a hydroxyl modified perovskite product; step four: 3-dimethylamino-1, 2-propanediol, fluorine-containing diol and polytetrahydrofuran ether glycol are added into a three-neck flask, and are dehydrated for 1-2 hours under the stirring of 105-110 ℃, and diisocyanate is added dropwise under the stirring of 50-60 ℃ to prepare fluorine-containing zwitterionic polyurethane prepolymer; step five: adding hydroxyl modified perovskite into fluorine-containing zwitterionic polyurethane prepolymer, adding chain extender, and ultrasonically mixing uniformly. The light-emitting antifouling coating has the advantages of low photocatalyst loss, high photocatalytic efficiency, warning effect and antifouling effect.
Description
Technical Field
The invention relates to the field of marine antifouling coatings, in particular to a perovskite anchoring fluorine-containing zwitter-ion polyurethane luminescent antifouling coating and a preparation method thereof.
Background
At present, the marine buoy is usually coated with self-polishing antifouling paint or ablation antifouling paint to prevent the attachment of fouling organisms. Meanwhile, the buoy often needs an additional light source to play a role in warning, and the collision of the marine vessel is prevented. At present, an antifouling coating with antifouling performance and luminous warning function does not exist. Compared with the traditional catalyst with quantum efficiency of only a few percent to a dozen percent, the perovskite has 100 percent of photoelectric conversion rate, can generate singlet oxygen, has excellent sterilization capability and can be used in the antifouling field.
However, the application of perovskite in the field of marine antifouling may present the following technical difficulties:
1. perovskite stability is poor, can take place to dissolve when meeting water, reduces bactericidal ability.
2. Under the conditions of insufficient illumination, over-strong illumination or darkness, the photocatalytic antifouling effect of the perovskite is reduced, so that the antifouling performance of the composite coating is reduced.
3. When the perovskite is applied to the antifouling field, the load bearing without the carrier is easy to lose, and the common resin carrier cannot play a role in enhancing the photocatalytic effect, so that the photocatalytic efficiency is lower.
Through search, the perovskite is mostly applied in the field of solar cells at present. For example, chinese patent documents CN104091888A, CN104795501A, CN103915567A, CN106252512A, etc. are rarely applied in the field of antifouling, and have the technical problems mentioned above.
Therefore, the preparation of the luminous antifouling coating which has low photocatalyst loss, high photocatalytic efficiency and both warning effect and antifouling effect has important significance.
Disclosure of Invention
In view of the above, in order to solve the above technical problems, the present invention aims to provide a luminescent antifouling coating of perovskite-anchored fluorine-containing zwitterion polyurethane and a preparation method thereof, wherein the luminescent antifouling coating has low photocatalyst loss, high photocatalytic efficiency, and both warning and antifouling effects.
The adopted technical scheme is as follows:
the invention discloses a preparation method of a perovskite anchoring fluorine-containing zwitter-ion polyurethane luminescent antifouling coating, which comprises the following steps:
the method comprises the following steps: mixing cesium carbonate, octadecene and oleic acid with reaction amount, adding the mixture into a three-mouth bottle, heating to 120-130 ℃, vacuum drying for 1-2 hours, and then heating to 150-160 ℃ under the protection of nitrogen until all cesium carbonate and oleic acid completely react to obtain a product precursor cesium oleate;
step two: putting octadecene, oleic acid, oleylamine and lead halide with reaction amount into a three-neck flask, heating to 125 ℃ for vacuum drying for 1-2 hours, heating to 130 ℃ and 160 ℃ after the lead halide is completely dissolved, quickly injecting the precursor cesium oleate synthesized in the step I, injecting 5-6 seconds, and quickly cooling the reaction to room temperature by using an ice bath to form a product perovskite;
step three: dispersing the perovskite in methanol, dropwise adding 1-thioglycerol under stirring, and reacting for 12-13 hours to obtain a hydroxyl modified perovskite product;
step four: adding 3-dimethylamino-1, 2-propanediol, fluorine-containing diol and polytetrahydrofuran ether glycol into a three-neck flask with a mechanical stirring device, a thermometer and an air extraction joint, dehydrating for 1-2h under stirring at the temperature of 105-110 ℃, dropwise adding diisocyanate under stirring at the temperature of 50-60 ℃, uniformly mixing, heating to 80-85 ℃ for reacting for 2-3h, dropwise adding 1, 3-propane sultone under stirring at the temperature of 40-45 ℃, and preserving heat for 12-13h to obtain a fluorine-containing zwitterion polyurethane prepolymer;
step five: and adding the hydroxyl modified perovskite obtained in the third step into the fluorine-containing zwitterionic polyurethane prepolymer obtained in the fourth step, adding a chain extender, and ultrasonically mixing uniformly to obtain the product perovskite-anchored fluorine-containing zwitterionic polyurethane luminescent antifouling coating.
Further, still include:
step six: the perovskite anchoring fluorine-containing zwitter-ion polyurethane luminescent antifouling coating is spin-coated on a substrate to prepare a sample wafer in a spin-coating mode at the rotating speed within the range of 200-600rpm, and then the prepared sample wafer is dried to constant weight at room temperature.
Further, in the first step, the reaction amount of cesium carbonate, octadecene and oleic acid is 0.5-1g of cesium carbonate, 35-50mL of octadecene and 2.5-3mL of oleic acid.
Further, in the second step, the reacting amount of octadecene, oleic acid, oleylamine and lead halide is 5-10mL of octadecene, 0.5-1mL of oleic acid, 0.5-1mL of oleylamine and 0.15-0.20mmol of lead halide.
Further, the third step and the fourth step are performed simultaneously, or the fourth step is performed first, and then the third step is performed. Of course, step three may be performed first, and then step four may be performed. The order of step three and step four is not limited in particular embodiments.
Further, in the second step, the lead halide includes one or more of lead chloride, lead bromide and lead iodide.
Further, in the second step, after the lead halide is completely dissolved, the temperature is heated to 150-160 ℃.
Further, in the fourth step, the diisocyanate includes one or more of toluene diisocyanate, isophorone diisocyanate, diphenylmethane diisocyanate, and hexamethylene diisocyanate.
Further, in the sixth step, the thickness of the dry film spin-coated on the substrate is 100-.
The perovskite anchoring fluorine-containing zwitter-ion polyurethane luminescent antifouling coating is prepared by the preparation method of any scheme.
The invention has the beneficial effects that:
1. according to the invention, the perovskite and polyurethane form a covalent bond through an oleic acid and oleylamine (namely oleylamine) bond, the binding force is enhanced, the polyurethane plays a role in protecting the perovskite, and the problem that the perovskite is decomposed in water is solved;
2. the perovskite antifouling coating has the functions of luminescence warning and marine antifouling, does not need an external light source, and is energy-saving and environment-friendly;
3. the polyurethane grafted fluorine-containing amphoteric ion resin matrix provides a carrier for the perovskite, and fluorine elements in the resin can generate a piezoelectric effect with the perovskite, so that the photocatalytic efficiency is improved, and the photocatalytic antifouling effect is enhanced.
Detailed Description
The present invention is described in detail below with reference to specific examples, but the use and purpose of these exemplary embodiments are merely to exemplify the present invention, and do not set forth any limitation on the actual scope of the present invention in any form, and the scope of the present invention is not limited thereto.
Example 1
a. Mixing 0.8g of cesium carbonate, 40mL of octadecene and 2.8mL of oleic acid, adding the mixture into a 100mL three-necked bottle, heating to 120 ℃, vacuum-drying for 1 hour, and heating to 150 ℃ under the protection of nitrogen until all cesium carbonate and oleic acid completely react to obtain a product precursor cesium oleate;
b. putting 5mL of octadecene, 0.5mL of oleic acid, 0.5mL of oleylamine and 0.188 mmol of lead chloride into a three-neck flask, heating to 120 ℃, vacuum drying for 1 hour, heating to 160 ℃ after the lead chloride is completely dissolved, quickly injecting a synthesized product precursor cesium oleate, injecting 5s of lead chloride, and quickly cooling the reaction to room temperature by using an ice bath to obtain a product perovskite;
c. adding 3-dimethylamino-1, 2-propanediol, 2,3, 3-tetrafluoro-1, 4-butanediol and polytetrahydrofuran ether (molecular weight 1000) into a three-neck flask with a mechanical stirring device, a thermometer and an air extraction joint, dehydrating for 1h under stirring at 105 ℃, dropwise adding toluene diisocyanate under stirring at 50 ℃, uniformly mixing, heating to 80-85 ℃ for reacting for 2h, dropwise adding 1, 3-propane sultone under stirring at 40 ℃, and preserving heat for 12h to obtain a fluorine-containing zwitterion polyurethane prepolymer;
d. dispersing the product perovskite in methanol, dropwise adding 1-thioglycerol under stirring, and reacting for 12 hours to obtain a product hydroxyl modified perovskite;
e. adding the product hydroxyl modified perovskite into the product polyurethane grafted zwitterionic polymer, adding a chain extender, and ultrasonically mixing uniformly to obtain the perovskite anchored fluorine-containing zwitterionic polyurethane luminescent antifouling coating;
f. the perovskite anchoring fluorine-containing zwitterionic polyurethane luminescent antifouling coating is spin-coated on a substrate at the rotating speed within the range of 400rpm by adopting a spin-coating mode to prepare a sample wafer, and the thickness of a dry film spin-coated on the substrate is about 120 mu m. The prepared sample piece is dried to constant weight at room temperature.
The samples of this example were tested for the following relevant properties and traits:
attachment rate of nitzschia closterium: 7.7 percent of the total weight of the steel,
the antibacterial rate of staphylococcus aureus is as follows: the content of the active carbon is 96.41%,
the antibacterial rate of escherichia coli is as follows: 94.36 percent.
Example 2
Referring to example 1, the difference from example 1 is that the lead halide of this example is changed to lead bromide, and the rest of the method is the same as example 1, as shown in example 1.
The samples of this example were tested for the following relevant properties and traits:
attachment rate of nitzschia closterium: 4.9 percent of the total weight of the steel,
the antibacterial rate of staphylococcus aureus is as follows: the content of the active carbon is 98.73%,
the antibacterial rate of escherichia coli is as follows: 96.32 percent.
Example 3
Referring to example 1, the difference from example 1 is that the lead halide of this example is changed to lead iodide, and the rest of the method is the same as example 1, as shown in example 1.
The samples of this example were tested for the following relevant properties and traits:
attachment rate of nitzschia closterium: 2.6 percent of the total weight of the mixture,
the antibacterial rate of staphylococcus aureus is as follows: 99.15 percent of the total weight of the mixture,
the antibacterial rate of escherichia coli is as follows: 98.03 percent.
Example 4
Referring to example 1, the toluene diisocyanate of example 1 was changed to isophorone diisocyanate, and the procedure of example 1 was the same as that of example 1, as shown in example 1.
The samples of this example were tested for the following relevant properties and traits:
attachment rate of nitzschia closterium: 8.3 percent of the total weight of the mixture,
the antibacterial rate of staphylococcus aureus is as follows: the content of the active carbon is 94.72%,
the antibacterial rate of escherichia coli is as follows: 93.11 percent.
Example 5
Referring to example 1, the toluene diisocyanate of example 1 is changed to diphenylmethane diisocyanate, which is different from example 1, and the rest of the method is the same as example 1, and is kept unchanged as shown in example 1.
The samples of this example were tested for the following relevant properties and traits:
attachment rate of nitzschia closterium: 5.53 percent of the total weight of the steel,
the antibacterial rate of staphylococcus aureus is as follows: the content of the active carbon is 93.91%,
the antibacterial rate of escherichia coli is as follows: 93.08 percent.
Example 6
Referring to example 1, the toluene diisocyanate of example 1 is changed to hexamethylene diisocyanate, which is different from example 1, and the rest of the method is the same as example 1, and is as shown in example 1.
The samples of this example were tested for the following relevant properties and traits:
attachment rate of nitzschia closterium: 5.66 percent of the total weight of the steel,
the antibacterial rate of staphylococcus aureus is as follows: 97.39 percent of the total weight of the mixture,
the antibacterial rate of escherichia coli is as follows: 95.25 percent.
Example 7
Referring to example 1, the difference from example 1 is that the spin speed of this example is changed to 450rpm, and the rest of the method is the same as example 1, as shown in example 1.
The samples of this example were tested for the following relevant properties and traits:
attachment rate of nitzschia closterium: 7.1 percent of the total weight of the mixture,
the antibacterial rate of staphylococcus aureus is as follows: 95.79 percent of the total weight of the mixture,
the antibacterial rate of escherichia coli is as follows: 94.07 percent.
Example 8
Referring to example 1, the difference from example 1 is that the spin speed of this example is changed to 500rpm, and the rest of the method is the same as example 1, as shown in example 1.
The samples of this example were tested for the following relevant properties and traits:
attachment rate of nitzschia closterium: 6.3 percent of the total weight of the mixture,
the antibacterial rate of staphylococcus aureus is as follows: 94.36 percent of the total weight of the mixture,
the antibacterial rate of escherichia coli is as follows: 92.91 percent.
The invention takes fluorine-containing zwitterionic polyurethane resin as a resin carrier, and introduces inorganic perovskite into a resin matrix through the reaction of oleic acid oil amine bond and polyurethane isocyanate group, thus preparing the perovskite-anchored fluorine-containing zwitterionic polyurethane luminescent antifouling coating. Compared with the antifouling coating of the buoy, the photoluminescence effect of the perovskite composite coating can play a warning role, an additional external light source is not needed, and the energy is saved; meanwhile, the introduction of polyurethane not only reduces the elastic modulus of the coating and is not beneficial to the attachment of fouling organisms, but also provides a reaction site with perovskite, so that the inorganic perovskite is more stably anchored on the surface of the coating and cannot be lost; compared with the conventional photocatalytic coating, the fluorine element in the resin matrix can generate a piezoelectric effect with perovskite, so that the photocatalytic efficiency is improved, and the photocatalytic antifouling effect is enhanced.
The above-listed detailed description is only a specific description of a possible embodiment of the present invention, and they are not intended to limit the scope of the present invention, and equivalent embodiments or modifications made without departing from the technical spirit of the present invention should be included in the scope of the present invention.
Claims (10)
1. The preparation method of the perovskite anchoring fluorine-containing zwitterion polyurethane luminescent antifouling paint is characterized by comprising the following steps:
the method comprises the following steps: mixing cesium carbonate, octadecene and oleic acid with reaction amount, adding the mixture into a three-mouth bottle, heating to 120-130 ℃, vacuum drying for 1-2 hours, and then heating to 150-160 ℃ under the protection of nitrogen until all cesium carbonate and oleic acid completely react to obtain a product precursor cesium oleate;
step two: putting octadecene, oleic acid, oleylamine and lead halide with reaction amount into a three-neck flask, heating to 125 ℃ for vacuum drying for 1-2 hours, heating to 130 ℃ and 160 ℃ after the lead halide is completely dissolved, quickly injecting the precursor cesium oleate synthesized in the step I, injecting 5-6 seconds, and quickly cooling the reaction to room temperature by using an ice bath to form a product perovskite;
step three: dispersing the perovskite in methanol, dropwise adding 1-thioglycerol under stirring, and reacting for 12-13 hours to obtain a hydroxyl modified perovskite product;
step four: adding 3-dimethylamino-1, 2-propanediol, fluorine-containing diol and polytetrahydrofuran ether glycol into a three-neck flask with a mechanical stirring device, a thermometer and an air extraction joint, dehydrating for 1-2h under stirring at the temperature of 105-110 ℃, dropwise adding diisocyanate under stirring at the temperature of 50-60 ℃, uniformly mixing, heating to 80-85 ℃ for reacting for 2-3h, dropwise adding 1, 3-propane sultone under stirring at the temperature of 40-45 ℃, and preserving heat for 12-13h to obtain a fluorine-containing zwitterion polyurethane prepolymer;
step five: and adding the hydroxyl modified perovskite obtained in the third step into the fluorine-containing zwitterionic polyurethane prepolymer obtained in the fourth step, adding a chain extender, and ultrasonically mixing uniformly to obtain the product perovskite anchoring fluorine-containing zwitterionic polyurethane luminescent antifouling paint.
2. A preparation method of a perovskite anchoring fluorine-containing zwitterionic polyurethane luminescent antifouling coating is characterized in that a perovskite anchoring fluorine-containing zwitterionic polyurethane luminescent antifouling coating prepared by the preparation method in the claim 1 is coated on a substrate in a spin coating mode at the rotating speed within the range of 200-600rpm to prepare a sample wafer, and then the prepared sample wafer is dried at room temperature to constant weight.
3. The method for preparing the perovskite anchoring fluorine-containing zwitterionic polyurethane luminescent antifouling paint as claimed in claim 1, wherein in the step one, the reaction amount of cesium carbonate, octadecene and oleic acid is 0.5-1g of cesium carbonate, 35-50mL of octadecene and 2.5-3mL of oleic acid.
4. The method for preparing the perovskite anchoring fluorine-containing zwitterionic polyurethane luminescent antifouling paint as claimed in claim 1, wherein in the second step, the reacting amount of octadecene, oleic acid, oleyl amine and lead halide is 5-10mL of octadecene, 0.5-1mL of oleic acid, 0.5-1mL of oleyl amine and 0.15-0.20mmol of lead halide.
5. The method for preparing the perovskite anchoring fluorine-containing zwitterionic polyurethane luminescent antifouling paint as claimed in claim 1, wherein the third step and the fourth step are performed simultaneously, or the fourth step is performed first and then the third step is performed.
6. The method for preparing the perovskite anchoring fluorine-containing zwitterionic polyurethane luminescent antifouling paint as claimed in claim 1, wherein in the second step, the lead halide comprises one or more of lead chloride, lead bromide and lead iodide.
7. The method for preparing the perovskite anchoring fluorine-containing zwitterionic polyurethane luminescent antifouling paint as claimed in claim 6, wherein in the second step, after the lead halide is completely dissolved, the coating is heated to 150-160 ℃.
8. The method for preparing the perovskite anchoring fluorine-containing zwitterionic polyurethane luminescent antifouling paint as claimed in claim 1, wherein in the fourth step, the diisocyanate comprises one or more of toluene diisocyanate, isophorone diisocyanate, diphenylmethane diisocyanate and hexamethylene diisocyanate.
9. The method for preparing the perovskite anchored fluorine-containing zwitterionic polyurethane luminescent antifouling coating as claimed in claim 2, wherein in the sixth step, the dry film thickness of the coating spin-coated on the substrate is 100-140 μm.
10. A perovskite anchoring fluorine-containing zwitterion polyurethane luminescent antifouling paint, which is characterized by being prepared by the preparation method of any one of claims 1 and 3-8.
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