CN114686031B - Corrosion-resistant fluorescent paint and preparation method thereof - Google Patents
Corrosion-resistant fluorescent paint and preparation method thereof Download PDFInfo
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- CN114686031B CN114686031B CN202210462825.XA CN202210462825A CN114686031B CN 114686031 B CN114686031 B CN 114686031B CN 202210462825 A CN202210462825 A CN 202210462825A CN 114686031 B CN114686031 B CN 114686031B
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- 238000005260 corrosion Methods 0.000 title claims abstract description 30
- 230000007797 corrosion Effects 0.000 title claims abstract description 30
- 239000003973 paint Substances 0.000 title claims abstract description 28
- 238000002360 preparation method Methods 0.000 title claims abstract description 23
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 claims abstract description 62
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical class [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 44
- 244000028419 Styrax benzoin Species 0.000 claims abstract description 31
- 235000000126 Styrax benzoin Nutrition 0.000 claims abstract description 31
- 235000008411 Sumatra benzointree Nutrition 0.000 claims abstract description 31
- 229960002130 benzoin Drugs 0.000 claims abstract description 31
- 235000019382 gum benzoic Nutrition 0.000 claims abstract description 31
- 239000000843 powder Substances 0.000 claims abstract description 31
- 229910021389 graphene Inorganic materials 0.000 claims abstract description 25
- 238000000576 coating method Methods 0.000 claims abstract description 20
- 239000011248 coating agent Substances 0.000 claims abstract description 19
- -1 europium ions Chemical class 0.000 claims abstract description 14
- OMUADEPNIQXNRG-UHFFFAOYSA-N 5-nitropyridine-3,4-diamine Chemical compound NC1=CN=CC([N+]([O-])=O)=C1N OMUADEPNIQXNRG-UHFFFAOYSA-N 0.000 claims abstract description 12
- SLIBCJURSADKPV-UHFFFAOYSA-N 1,10-dihydro-1,10-phenanthroline-4,7-dione Chemical compound N1C=CC(=O)C2=CC=C3C(=O)C=CNC3=C21 SLIBCJURSADKPV-UHFFFAOYSA-N 0.000 claims abstract description 11
- UXOQQUHZHRSERD-UHFFFAOYSA-N methyl 6-cyano-1h-indole-3-carboxylate Chemical compound N#CC1=CC=C2C(C(=O)OC)=CNC2=C1 UXOQQUHZHRSERD-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000003094 microcapsule Substances 0.000 claims abstract description 10
- VUZNLSBZRVZGIK-UHFFFAOYSA-N 2,2,6,6-Tetramethyl-1-piperidinol Chemical compound CC1(C)CCCC(C)(C)N1O VUZNLSBZRVZGIK-UHFFFAOYSA-N 0.000 claims abstract description 8
- HFAUMPWMNPYULN-UHFFFAOYSA-N 2-bromo-3-methylbutanoyl bromide Chemical compound CC(C)C(Br)C(Br)=O HFAUMPWMNPYULN-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000004925 Acrylic resin Substances 0.000 claims abstract description 7
- 229920000178 Acrylic resin Polymers 0.000 claims abstract description 7
- 239000011162 core material Substances 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 47
- 238000002156 mixing Methods 0.000 claims description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 38
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 30
- 238000003756 stirring Methods 0.000 claims description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 22
- 239000008367 deionised water Substances 0.000 claims description 22
- 229910021641 deionized water Inorganic materials 0.000 claims description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 18
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 17
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
- 229910001940 europium oxide Inorganic materials 0.000 claims description 15
- AEBZCFFCDTZXHP-UHFFFAOYSA-N europium(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Eu+3].[Eu+3] AEBZCFFCDTZXHP-UHFFFAOYSA-N 0.000 claims description 15
- 238000005406 washing Methods 0.000 claims description 13
- NNMXSTWQJRPBJZ-UHFFFAOYSA-K europium(iii) chloride Chemical compound Cl[Eu](Cl)Cl NNMXSTWQJRPBJZ-UHFFFAOYSA-K 0.000 claims description 12
- 238000001035 drying Methods 0.000 claims description 11
- 238000010438 heat treatment Methods 0.000 claims description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 claims description 10
- 229920003180 amino resin Polymers 0.000 claims description 8
- 239000002243 precursor Substances 0.000 claims description 8
- 239000002202 Polyethylene glycol Substances 0.000 claims description 7
- 239000012153 distilled water Substances 0.000 claims description 7
- 229920001223 polyethylene glycol Polymers 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- 238000000227 grinding Methods 0.000 claims description 5
- 239000005457 ice water Substances 0.000 claims description 5
- 239000003208 petroleum Substances 0.000 claims description 5
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 230000004048 modification Effects 0.000 claims description 3
- 238000012986 modification Methods 0.000 claims description 3
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 claims description 3
- 238000001132 ultrasonic dispersion Methods 0.000 claims description 3
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- 239000000839 emulsion Substances 0.000 claims description 2
- GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 229960001124 trientine Drugs 0.000 claims description 2
- 238000002604 ultrasonography Methods 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- OWZCRTDJCYPKAO-UHFFFAOYSA-N 2-bromopentanoyl bromide Chemical compound CCCC(Br)C(Br)=O OWZCRTDJCYPKAO-UHFFFAOYSA-N 0.000 claims 1
- 230000000176 photostabilization Effects 0.000 claims 1
- 238000009210 therapy by ultrasound Methods 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 18
- 230000000087 stabilizing effect Effects 0.000 abstract description 12
- 229910052693 Europium Inorganic materials 0.000 abstract description 7
- 230000002209 hydrophobic effect Effects 0.000 abstract description 3
- 238000010382 chemical cross-linking Methods 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- 239000012528 membrane Substances 0.000 abstract 1
- 238000007193 benzoin condensation reaction Methods 0.000 description 24
- 230000000052 comparative effect Effects 0.000 description 15
- 230000004888 barrier function Effects 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- 206010070834 Sensitisation Diseases 0.000 description 2
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 2
- 239000004568 cement Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- LKPFBGKZCCBZDK-UHFFFAOYSA-N n-hydroxypiperidine Chemical compound ON1CCCCC1 LKPFBGKZCCBZDK-UHFFFAOYSA-N 0.000 description 2
- 238000005424 photoluminescence Methods 0.000 description 2
- 230000008313 sensitization Effects 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
Classifications
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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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/003—Compounds containing elements of Groups 3 or 13 of the Periodic Table without C-Metal linkages
-
- 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
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
-
- 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
- C09D5/08—Anti-corrosive paints
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/182—Metal complexes of the rare earth metals, i.e. Sc, Y or lanthanide
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Paints Or Removers (AREA)
Abstract
The invention discloses a corrosion-resistant fluorescent paint and a preparation method thereof, and relates to the technical field of paints. According to the invention, 5-nitropyridine-3,4-diamine, 6-cyanoindole-3-carboxylic acid methyl ester, 2,2,6,6-tetramethylpiperidinol and benzoin are firstly utilized to prepare a benzoin condensate, so that the coating has a light stabilizing effect, and is matched with 4,7-dihydroxy-1,10-phenanthroline to be positioned in europium ions, so that photoluminescent self-made fluorescent powder is obtained, and the coating has long-acting fluorescence; then, taking acrylic resin as a wall material and self-made fluorescent powder as a core material to obtain microcapsules, and sequentially coating the modified graphene and the hydrophobic membrane through chemical crosslinking to effectively isolate the permeation of corrosive media; the modified graphene is prepared from graphene, 2-bromoisopentanoyl bromide and 5-mercapto-4-p-chlorophenyl-4H-3-hydroxy-1,2,4-triazole, and the dispersibility of the graphene oxide is improved. The corrosion-resistant fluorescent paint prepared by the invention has the effects of corrosion resistance and long-acting fluorescence.
Description
Technical Field
The invention relates to the technical field of coatings, in particular to a corrosion-resistant fluorescent coating and a preparation method thereof.
Background
The current methods for preparing fluorescent paint include: (1) Synthesizing resin with a fluorescent effect, and utilizing the fluorescent property of the resin to emit light; and (2) adding fluorescent powder as a filler to prepare the fluorescent paint. The first method has complex preparation process and strict requirements on process conditions, and uses a large amount of organic solvent, and the residual organic solvent can cause environmental pollution. The second method is relatively simple in process, but the dispersion of the fluorescent powder has problems, so that the light emission is not uniform, the local fluorescence is quenched, the light resistance of the two methods is poor, and the aging phenomenon is easy to occur under multiple times of illumination.
The fluorescent paint is usually coated on tunnels, building outer walls, billboards and the like and is exposed for a long time, and polyester resin is adopted as a matrix in the fluorescent paint, so that the fluorescent paint is easy to hydrolyze in a humid environment and is easy to react with an acidic medium, and therefore, the fluorescent paint is often corroded, aged, shed and the like. Based on this, how to prepare a corrosion-resistant fluorescent paint is very important.
Disclosure of Invention
The invention aims to provide a corrosion-resistant fluorescent paint and a preparation method thereof, and aims to solve the problems in the prior art.
In order to solve the technical problems, the invention provides the following technical scheme: the preparation method of the corrosion-resistant fluorescent paint comprises the following steps of mixing self-made fluorescent powder and polyethylene glycol in distilled water, stirring at a high speed and under ultrasound to form a core material emulsion, then adding acrylic resin, stirring to obtain microcapsules, and then carrying out modification treatment.
Further, the self-made fluorescent powder is prepared from 5-nitropyridine-3,4-diamine, 6-cyanoindole-3-carboxylic acid methyl ester, 2,2,6,6-tetramethylpiperidinol, benzoin, 4,7-dihydroxy-1,10-phenanthroline and europium oxide.
Further, the modification treatment comprises the following steps of mixing the modified graphene, the azobisisobutyronitrile and the methanol, adding the microcapsule, placing the microcapsule in a water bath, reacting for a preset time, adding the 1-hydroxytetradecane, stirring the mixture for reaction, washing and distilling the reaction product.
Furthermore, the modified graphene is prepared from graphene oxide, 2-bromoisopentanoyl bromide and 5-mercapto-4-p-chlorophenyl-4H-3-hydroxy-1,2,4-triazole.
Further, the preparation method of the corrosion-resistant fluorescent paint comprises the following preparation steps:
(1) Mixing deionized water, 6-cyanoindole-3-carboxylic acid methyl ester and sodium hydroxide according to a mass ratio of 4;
(2) Mixing an azo compound, 2,2,6,6-tetramethyl piperidinol and tetraisopropyl titanate according to the mass ratio of 1;
(3) Dissolving benzoin in absolute ethyl alcohol with the mass 4-8 times that of the benzoin, adding a light-stabilized compound solution with the mass 1.5-3.7 times that of the benzoin, reacting at 50-100 rpm for 4-8 h, distilling at 50-64 ℃ and the vacuum degree of 20-40 kPa for 46-62 min, adding petroleum ether with the mass 3-5 times that of the benzoin, cooling to 0-5 ℃, filtering, and washing with distilled water for 3-5 times to obtain a benzoin condensation compound;
(4) Dissolving a benzoin condensation compound in absolute ethyl alcohol with the mass 4-7 times of that of the benzoin condensation compound in a water bath at 50-60 ℃, stirring and dissolving, adding a europium chloride solution with the mass 1-3 times of that of the benzoin condensation compound, adding a sodium hydroxide solution with the mass fraction of 10% until the pH of the solution is 7-8, reacting at 100-200 rpm for 1-4 h, adding 4,7-dihydroxy-1,10-phenanthroline with the mass 0.1-0.4 time of the benzoin condensation compound, and absolute ethyl alcohol with the mass 1-3 times of that of the benzoin condensation compound, continuing to react for 1-3 h, heating to 80-90 ℃, distilling for 1.5-4 h, drying at 70-80 ℃ and under the vacuum degree of 10-30 kPa for 2-5 h to obtain fluorescent powder;
(5) Mixing the self-made fluorescent powder, polyethylene glycol and deionized water according to a mass ratio of 1.1;
(6) Mixing modified graphene, azodiisobutyronitrile and methanol according to the mass ratio of 1.005; and (2) uniformly mixing the coating precursor, the organic solvent and the curing agent according to the mass ratio of 1.2.
Further, the preparation method of the 5-nitropyridine-3,4-diamine solution in the step (1) comprises the following steps: after stirring and dissolving 98 mass percent of concentrated sulfuric acid, deionized water and 5-nitropyridine-3,4-diamine according to the mass ratio of 1.0.
Further, the light stabilizing compound solution in the step (3) is prepared by mixing a light stabilizing compound and anhydrous ethanol according to a mass ratio of 1.
Further, the preparation method of the europium chloride solution in the step (4) comprises the following steps: europium oxide is dissolved in concentrated hydrochloric acid with the mass fraction of 38 percent, the mass fraction of which is 15 to 18 times that of the europium oxide, the solution is heated to 35 to 42 ℃, and the temperature is kept for 58 to 70min.
Further, the preparation method of the modified graphene in the step (6) comprises the following steps: mixing graphene oxide, triethylamine and N, N-dimethylformamide according to a mass ratio of 1:3: 44-1: 48, ultrasonically dispersing for 30-42 min at 25-35 kHz, adding 2-bromoisovaleryl bromide which is 1-3 times of the mass of the graphene oxide into ice water bath, stirring for 16-20 h at 200-300 rpm, adding 5-mercapto-4-p-chlorophenyl-4-hydro-3-hydroxy-1,2,4-triazole which is 1-3 times of the mass of the graphene oxide, stirring for 4-7 h at the same speed, washing for 3-5 times by using N, N-dimethylformamide and deionized water, centrifuging for 7-18min at 5000-7000 rpm, drying for 2-4 h at 60-70 ℃, and grinding through a 400-600-mesh sieve.
Further, the organic solvent in the step (6) is one or more of propylene glycol methyl ether, xylene, ethyl acetate and tetrahydrofuran; the curing agent is one or a mixture of amino resin, triethylene tetramine and dipropylene triamine.
Compared with the prior art, the invention has the following beneficial effects:
the invention adopts the self-made fluorescent powder and the modified resin as raw materials to prepare the fluorescent paint, so as to realize the effects of long-acting fluorescence and corrosion resistance.
Firstly, 5-nitropyridine-3,4-diamine and 6-cyanoindole-3-carboxylic acid methyl ester are connected by azo group, and the azo group and the ortho-nitro group form a ring; then, reacting an ester group of the 6-cyanoindole-3-carboxylic acid methyl ester with a hydroxyl group of piperidinol to form a light-stabilizing compound, so that the self-made fluorescent powder has light resistance and still has a fluorescent effect under multiple times of illumination, the service life of the self-made fluorescent powder is prolonged, and the coating has a long-acting fluorescent effect; condensing the light-stabilizing compound with benzoin, and coordinating with 4,7-dihydroxy-1,10-phenanthroline to locate in europium ions to obtain self-made photoluminescent phosphor; the complex has sensitization effect on europium ions to excite the europium ions to emit light, has a conjugated long chain, effectively improves the luminous efficiency, expands a conjugated system by amino, hydroxyl and cyano at the tail end, enhances the luminous effect, and improves the long-acting fluorescent effect of the self-made fluorescent powder.
Secondly, under the action of an emulsifier, the acrylic resin coats the self-made fluorescent powder to form a microcapsule; after graphene is oxidized, the hydroxyl on the surface of the graphene is used as an active site to be covalently connected with 2-bromoisopentanoyl bromide, the remaining bromide ions are used for reacting with 5-mercapto-4-p-chlorophenyl-4-hydrogen-3-hydroxy-1,2,4-triazole, and then mercapto groups and acrylic resin undergo free radical polymerization, so that graphene is deposited on the surface of a microcapsule to form a barrier layer, the permeation of corrosive media is effectively isolated, the coating has a corrosion resistance effect, then 1-hydroxytetradecane is introduced by using chloride ions in a graphene molecular chain to form a hydrophobic film on the surface of the graphene, the barrier effect of the barrier layer is further enhanced, and the corrosion resistance of the coating is improved.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be obtained by a person skilled in the art without making any creative effort based on the embodiments in the present invention, belong to the protection scope of the present invention.
In order to more clearly illustrate the method provided by the present invention, the following examples are used to illustrate the method for testing each index of the corrosion-resistant fluorescent paint prepared in the following examples as follows:
long-lasting fluorescence: coating the embodiment and the comparative example with the same mass on a cement board, and carrying out photoluminescence and light stability effect tests;
photoluminescence: irradiating with 200-400 nm ultraviolet lamp to observe the surface with or without luminescence;
light stabilization: continuously irradiating for 18d by an ultraviolet lamp with the wavelength of 200-400 nm, and observing the fluorescence intensity.
Corrosion resistance: coating the cement boards with the embodiment and the comparative example to the same thickness, and performing salt spray effect and water contact angle tests;
testing the salt spray effect: and (5) placing the sample in a salt fog box at 35 ℃, corroding for 300h, and observing whether the surface has corrosion stains.
Example 1
A preparation method of a corrosion-resistant fluorescent paint comprises the following preparation steps:
(1) Dissolving 98% concentrated sulfuric acid, deionized water and 5-nitropyridine-3,4-diamine in a mass ratio of 1.5; mixing deionized water, 6-cyanoindole-3-carboxylic acid methyl ester and sodium hydroxide according to a mass ratio of 4;
(2) Mixing an azo compound, 2,2,6,6-tetramethylpiperidinol and tetraisopropyl titanate according to a mass ratio of 1;
(3) Dissolving benzoin in absolute ethyl alcohol with the mass 4 times that of the benzoin, adding a light stabilizing compound solution with the mass 1.5 times that of the benzoin, reacting at 50rpm for 8h, distilling at 50 ℃ and the vacuum degree of 20kPa for 46min, adding petroleum ether with the mass 3 times that of the benzoin, cooling to 0 ℃, filtering, and washing with distilled water for 3 times to obtain a benzoin condensation compound, wherein the mass ratio of the light stabilizing compound to the absolute ethyl alcohol in the light stabilizing compound solution is 1;
(4) Dissolving europium oxide in concentrated hydrochloric acid with the mass fraction of 38% and the mass of the europium oxide being 15 times that of the europium oxide, heating to 35 ℃, and preserving heat for 70min to obtain a europium chloride solution; dissolving a benzoin condensation compound in absolute ethyl alcohol with the mass 4 times that of the benzoin condensation compound in water bath at 50 ℃, stirring and dissolving, adding a europium chloride solution with the mass 1 time that of the benzoin condensation compound, adding a sodium hydroxide solution with the mass fraction of 10% until the pH of the solution is 7, reacting for 4 hours at 100rpm, adding 4,7-dihydroxy-1,10-phenanthroline with the mass 0.1 time that of the benzoin condensation compound and absolute ethyl alcohol with the mass 1 time that of the benzoin condensation compound, continuously reacting for 1 hour, heating to 80 ℃, distilling for 4 hours, drying for 2 hours at 70 ℃ and vacuum degree of 10kPa to obtain fluorescent powder;
(5) Mixing the self-made fluorescent powder, polyethylene glycol and deionized water according to a mass ratio of 1.1;
(6) Mixing graphene oxide, triethylamine and N, N-dimethylformamide according to a mass ratio of 1:3, ultrasonically dispersing for 42min at 25kHz, adding 2-bromopivaloyl bromide which is 1 time of the mass of the graphene oxide into ice-water bath, stirring for 20h at 200rpm, adding 5-mercapto-4-p-chlorophenyl-4H-3-hydroxy-1,2,4-triazole which is 1 time of the mass of the graphene oxide, stirring for 7h at the same speed, washing for 3 times by using N, N-dimethylformamide and deionized water, centrifuging for 18min at 5000rpm, drying for 4h at 60 ℃, and grinding through a 400-mesh sieve to obtain modified graphene;
(7) Mixing modified graphene, azobisisobutyronitrile and methanol according to a mass ratio of 1.005; and (2) uniformly mixing the coating precursor, ethyl acetate and amino resin according to a mass ratio of 1.2.
Example 2
A preparation method of a corrosion-resistant fluorescent paint comprises the following preparation steps:
(1) Dissolving 98% concentrated sulfuric acid, deionized water and 5-nitropyridine-3,4-diamine in a mass ratio of 1.5; mixing deionized water, 6-cyanoindole-3-carboxylic acid methyl ester and sodium hydroxide according to the mass ratio of 5.5;
(2) Mixing an azo compound, 2,2,6,6-tetramethylpiperidinol and tetraisopropyl titanate according to a mass ratio of 1;
(3) Dissolving benzoin in absolute ethyl alcohol with the mass 6 times of that of the benzoin, adding a light stabilizing compound solution with the mass 2.6 times of that of the benzoin, reacting at 80rpm for 6h, distilling at 57 ℃ and the vacuum degree of 30kPa for 54min, adding petroleum ether with the mass 4 times of that of the benzoin, cooling to 3 ℃, filtering, and washing with distilled water for 4 times to obtain a benzoin condensation compound, wherein the mass ratio of the light stabilizing compound to the absolute ethyl alcohol in the light stabilizing compound solution is 1;
(4) Dissolving europium oxide in concentrated hydrochloric acid with the mass fraction of 38% and the mass of 16.5 times of that of the europium oxide, heating to 39 ℃, and preserving heat for 64min to obtain a europium chloride solution; dissolving a benzoin condensation compound in absolute ethyl alcohol with the mass 5.5 times that of the benzoin condensation compound in water bath at 55 ℃, stirring and dissolving, adding a europium chloride solution with the mass 2 times that of the benzoin condensation compound, adding a sodium hydroxide solution with the mass fraction of 10% until the pH of the solution is 7.5, reacting for 2.5h at 150rpm, adding 4,7-dihydroxy-1,10-phenanthroline with the mass 0.25 time that of the benzoin condensation compound, and absolute ethyl alcohol with the mass 2 times that of the benzoin condensation compound, continuing reacting for 2h, heating to 85 ℃, distilling for 2.7h, and drying for 3.5h at the temperature of 75 ℃ and the vacuum degree of 20kPa to obtain the self-made fluorescent powder;
(5) Mixing the self-made fluorescent powder, polyethylene glycol and deionized water according to a mass ratio of 1.1;
(6) Mixing graphene oxide, triethylamine and N, N-dimethylformamide according to a mass ratio of 1:4, performing ultrasonic dispersion for 36min at 30kHz, adding 2-bromoisopentanoyl bromide 2 times as much as the mass of the graphene oxide into ice-water bath, stirring for 18h at 250rpm, adding 5-mercapto-4-p-chlorophenyl-4-hydro-3-hydroxy-1,2,4-triazole 2 times as much as the mass of the graphene oxide, stirring for 5.5h at the same speed, washing for 4 times with N, N-dimethylformamide and deionized water, centrifuging for 12min at 6000rpm, drying for 3h at 65 ℃, and grinding through a 500-mesh sieve to obtain modified graphene;
(7) Mixing modified graphene, azodiisobutyronitrile and methanol according to a mass ratio of 1.006; and (2) uniformly mixing the coating precursor, ethyl acetate and amino resin according to a mass ratio of 1.9.
Example 3
The preparation method of the corrosion-resistant fluorescent paint comprises the following preparation steps:
(1) Dissolving 98% concentrated sulfuric acid, deionized water and 5-nitropyridine-3,4-diamine in a mass ratio of 1.5; mixing deionized water, 6-cyanoindole-3-carboxylic acid methyl ester and sodium hydroxide according to a mass ratio of 7;
(2) Mixing an azo compound, 2,2,6,6-tetramethylpiperidinol and tetraisopropyl titanate according to the mass ratio of 1;
(3) Dissolving benzoin in absolute ethyl alcohol with the mass 8 times that of the benzoin, adding a light stabilizing compound solution with the mass 3.7 times that of the benzoin, reacting at 100rpm for 4h, distilling at 64 ℃ and the vacuum degree of 40kPa for 62min, then adding petroleum ether with the mass 5 times that of the benzoin, cooling to 5 ℃, filtering, and washing with distilled water for 5 times to obtain a benzoin condensation compound, wherein the mass ratio of the light stabilizing compound to the absolute ethyl alcohol in the light stabilizing compound solution is 1;
(4) Dissolving europium oxide in concentrated hydrochloric acid with the mass fraction of 38 percent, which is 18 times of the mass of the europium oxide, heating to 42 ℃, and preserving heat for 58min to obtain a europium chloride solution; dissolving a benzoin condensation compound in absolute ethyl alcohol 7 times of the mass of the benzoin condensation compound in a water bath at 60 ℃, stirring and dissolving, adding a europium chloride solution 3 times of the mass of the benzoin condensation compound, adding a sodium hydroxide solution with the mass fraction of 10% until the pH of the solution is 8, reacting for 1h at 200rpm, adding 4,7-dihydroxy-1,10-phenanthroline 3 times of the mass of the benzoin condensation compound and absolute ethyl alcohol 3 times of the mass of the benzoin condensation compound, continuing to react for 3h, heating to 90 ℃, distilling for 1.5h, drying for 5h at the vacuum degree of 30kPa to obtain fluorescent powder;
(5) Mixing the self-made fluorescent powder, polyethylene glycol and deionized water according to a mass ratio of 1.1;
(6) Mixing graphene oxide, triethylamine and N, N-dimethylformamide according to a mass ratio of 1:5, performing ultrasonic dispersion for 30min at 35kHz, adding 2-bromoisopentanoyl bromide 3 times as much as the mass of the graphene oxide into an ice-water bath, stirring for 16h at 300rpm, adding 5-mercapto-4-p-chlorophenyl-4-hydro-3-hydroxy-1,2,4-triazole 3 times as much as the mass of the graphene oxide, stirring for 4h at the same speed, washing for 5 times with N, N-dimethylformamide and deionized water, centrifuging for 7min at 7000rpm, drying for 2h at 70 ℃, and grinding through a 600-mesh sieve to obtain modified graphene;
(7) Mixing modified graphene, azobisisobutyronitrile and methanol according to a mass ratio of 1.008; and (2) uniformly mixing the coating precursor, ethyl acetate and amino resin according to a mass ratio of 1.
Comparative example 1
Comparative example 1 differs from example 2 in that step (1) is different, step (1) being changed to: after stirring and dissolving 98 mass percent of concentrated sulfuric acid, deionized water and 5-nitropyridine-3,4-diamine according to the mass ratio of 1.5. The rest of the procedure was the same as in example 2.
Comparative example 2
Comparative example 2 differs from example 2 in that step (3) is not present and step (4) is changed to: dissolving europium oxide in concentrated hydrochloric acid with the mass fraction of 38% and the mass of 16.5 times of that of the europium oxide, heating to 39 ℃, and preserving heat for 64min to obtain a europium chloride solution; dissolving a light-stabilizing compound in absolute ethyl alcohol with the mass 5.5 times that of the light-stabilizing compound in water bath at 55 ℃, stirring and dissolving, adding a europium chloride solution with the mass 2 times that of the light-stabilizing compound, adding a sodium hydroxide solution with the mass fraction of 10% until the pH of the solution is 7.5, reacting at 150rpm for 2.5h, adding 4,7-dihydroxy-1,10-phenanthroline with the mass 0.25 time that of the light-stabilizing compound and absolute ethyl alcohol with the mass 2 times that of the light-stabilizing compound, continuing reacting for 2h, heating to 85 ℃, distilling for 2.7h, drying at 75 ℃ and the vacuum degree of 20kPa for 3.5h, and obtaining fluorescent powder. The rest of the procedure was the same as in example 2.
Comparative example 3
Comparative example 3 differs from example 2 in that step (5) is not present and step (7) is changed to: mixing modified graphene, azobisisobutyronitrile and methanol according to a mass ratio of 1.006; uniformly mixing the coating precursor, the self-made fluorescent powder, ethyl acetate and amino resin according to a mass ratio of 1.3. The rest of the procedure was the same as in example 2.
Comparative example 4
Comparative example 4 differs from example 2 in that step (6) is not present and step (7) is changed to: mixing graphene oxide, azobisisobutyronitrile and methanol according to a mass ratio of 1.006; and (2) uniformly mixing the coating precursor, ethyl acetate and amino resin according to a mass ratio of 1.9. The rest of the procedure was the same as in example 2.
Comparative example 5
Comparative example 5 differs from example 2 in that step (7) is different, step (7) being changed to: mixing modified graphene, azobisisobutyronitrile and methanol according to a mass ratio of 1.006; and (2) uniformly mixing the coating precursor, ethyl acetate and amino resin according to the mass ratio of 1.9. The rest of the procedure was the same as in example 2.
Effects of the invention
The following table 1 shows the results of performance analysis of the corrosion-resistant fluorescent paint using examples 1 to 3 of the present invention and comparative examples 1 to 5.
TABLE 1
From the comparison of experimental data of luminescence phenomenon and fluorescence intensity of examples and comparative examples, it can be found that 2,6-diamino-3-nitrosopyrimidine, 6-cyanoindole-3-methyl carboxylate, piperidinol and benzoin, 4,7-dihydroxy-1,10-phenanthroline are used in the product to form a coordination compound, europium ions are adsorbed, and the photoluminescent self-made fluorescent powder is obtained; the complex has a sensitization effect on europium ions, excites the europium ions to emit light, conjugates with long chains and a plurality of electron-assisted groups, improves the long-acting fluorescence effect of the self-made fluorescent powder, and improves the light stability effect of the complex, so that the coating has light resistance and the fluorescence of the self-made fluorescent powder is improved; the experimental data comparison of the water contact angle and the corrosion condition of the embodiment and the comparative example shows that the microcapsules are prepared by taking the acrylic resin as the wall material and the self-made fluorescent powder as the core material, the self-made fluorescent powder is protected, and the modified graphene and the hydrophobic film are sequentially coated through the chemical crosslinking reaction to form the barrier layer, so that the penetration of a corrosion medium is effectively isolated, and the coating has the corrosion resistance effect.
It will be evident to those skilled in the art that the invention is not limited to the details of the foregoing illustrative embodiments, and that the present invention may be embodied in other specific forms without departing from the spirit or essential attributes thereof. The present embodiments are therefore to be considered in all respects as illustrative and not restrictive, the scope of the invention being indicated by the appended claims rather than by the foregoing description, and all changes which come within the meaning and range of equivalency of the claims are therefore intended to be embraced therein. Any reference sign in a claim should not be construed as limiting the claim concerned.
Claims (7)
1. The preparation method of the corrosion-resistant fluorescent paint is characterized by comprising the following steps of mixing self-made fluorescent powder and polyethylene glycol in distilled water, stirring at a high speed and under ultrasound to form a core material emulsion, then adding acrylic resin, stirring to obtain microcapsules, and then carrying out modification treatment;
the self-made fluorescent powder is prepared from 5-nitropyridine-3,4-diamine, 6-cyanoindole-3-carboxylic acid methyl ester, 2,2,6,6-tetramethylpiperidinol, benzoin, 4,7-dihydroxy-1,10-phenanthroline and europium oxide;
mixing modified graphene, azodiisobutyronitrile and methanol, adding microcapsules, placing in a water bath, reacting for a preset time, adding 1-hydroxytetradecane, stirring for reaction, washing, and distilling;
the modified graphene is prepared from graphene oxide, 2-bromoisopentanoyl bromide and 5-mercapto-4-p-chlorophenyl-4H-3-hydroxy-1,2,4-triazole.
2. The preparation method of the corrosion-resistant fluorescent paint is characterized by comprising the following preparation steps of:
(1) Mixing deionized water, 6-cyanoindole-3-carboxylic acid methyl ester and sodium hydroxide according to the mass ratio of 4;
(2) Mixing an azo compound, 2,2,6,6-tetramethylpiperidinol and tetraisopropyl titanate according to a mass ratio of 1;
(3) Dissolving benzoin in absolute ethanol with the mass of 4~8 times that of the benzoin, adding a photostabilization compound solution with the mass of 1.5-3.7 times that of the benzoin, reacting at 50-100rpm for 4-8h, distilling at 50-64 ℃ and under the vacuum degree of 20-40kPa for 46-62min, then adding petroleum ether with the mass of 3~5 times that of the benzoin, cooling to 0~5 ℃, filtering, washing with distilled water for 3~5 times to obtain a benzoin condensate;
(4) Dissolving a benzoin condensate in absolute ethyl alcohol with the mass of the benzoin condensate being 4~7 times, stirring and dissolving, adding a europium chloride solution with the mass of the benzoin condensate being 1~3 times, adding a sodium hydroxide solution with the mass fraction of 10% until the pH of the solution is 7~8, reacting for 1 to 4 hours at 100 to 200rpm, adding 4,7-dihydroxy-1,10-phenanthroline and absolute ethyl alcohol with the mass of the benzoin condensate being 0.1 to 0.4 times, continuing to react for 1 to 3 hours, heating to 80 to 90 ℃, distilling for 1.5 to 4 hours, drying for 3536 to obtain the self-made fluorescent powder at the temperature of 70 to 80 ℃ and the vacuum degree of 10 to 30kPa for 2 to 5 hours after the 1.5 to 4 hours;
(5) Mixing the self-made fluorescent powder, polyethylene glycol and deionized water according to a mass ratio of 1:0.1 to 0.1, stirring at 1000 to 1500rpm for 20 to 30min, then performing ultrasonic treatment at 25 to 35kHz for 10 to 22min, then adding acrylic resin with the mass of 0.5 to 1 time of the self-made fluorescent powder, stirring uniformly, adding a 10% hydrochloric acid solution to a solution pH of 2~4, heating to 60 to 70 ℃, stirring at the same rotation speed for 1.5 to 3.5h, then adding a 20% sodium hydroxide solution until the solution pH is 6~7, and washing with deionized water 3~5 times to obtain the microcapsule;
(6) Mixing modified graphene, azobisisobutyronitrile and methanol according to a mass ratio of 1.005 to 0.008 of (1); and (2) uniformly mixing the coating precursor, the organic solvent and the curing agent according to a mass ratio of 1.2 to 1.
3. The method for preparing the corrosion-resistant fluorescent paint according to claim 2, wherein the preparation method of the 5-nitropyridine-3,4-diamine solution in the step (1) comprises the following steps: concentrated sulfuric acid with the mass fraction of 98%, deionized water and 5-nitropyridine-3,4-diamine are stirred and dissolved according to the mass ratio of (1.5).
4. The method for preparing the corrosion-resistant fluorescent paint according to claim 2, wherein the light-stabilizing compound solution in the step (3) is prepared by mixing a light-stabilizing compound and absolute ethyl alcohol in a mass ratio of 1.
5. The method for preparing a corrosion-resistant fluorescent paint according to claim 2, wherein the preparation method of the europium chloride solution in step (4) comprises the following steps: europium oxide is dissolved in concentrated hydrochloric acid with the mass fraction of 38 percent, wherein the mass of the concentrated hydrochloric acid is 15 to 18 times that of the europium oxide, the concentrated hydrochloric acid is heated to 35 to 42 ℃, and the temperature is kept for 58 to 70min.
6. The method for preparing the corrosion-resistant fluorescent paint according to claim 2, wherein the modified graphene prepared in the step (6) is prepared by: mixing graphene oxide, triethylamine and N, N-dimethylformamide according to a mass ratio of 1:3: 44: 1: 48, performing ultrasonic dispersion at 25: 35kHz for 30: 42min, adding 2-bromovaleryl bromide accounting for 5754 times of the mass of the graphene oxide as 1~3 into an ice water bath, stirring at 200: 300rpm for 16: 20h, adding 5-mercapto-4-p-chlorophenyl-4 hydrogen-3-hydroxy-1,2,4-triazole accounting for 3252 times of the mass of the graphene oxide as 3252 zxft, stirring at the same speed for 4: 7h, washing with N, N-dimethylformamide and deionized water for 3425 times as well as 3425 times, centrifuging at 5000: 7000rpm for 7: 18min, drying at 60: 70 ℃ for 2: 4h, and grinding the mixture through a sieve at 400: 600 ℃.
7. The method for preparing a corrosion-resistant fluorescent paint according to claim 2, wherein the organic solvent in step (6) is one or more of propylene glycol methyl ether, xylene, ethyl acetate and tetrahydrofuran; the curing agent is one or a mixture of amino resin, triethylene tetramine and dipropylene triamine.
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