CN107337950A - Fluorescent paint and preparation method thereof made of bigcatkin willow aldehydes schiff bases - Google Patents
Fluorescent paint and preparation method thereof made of bigcatkin willow aldehydes schiff bases Download PDFInfo
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- CN107337950A CN107337950A CN201710598892.3A CN201710598892A CN107337950A CN 107337950 A CN107337950 A CN 107337950A CN 201710598892 A CN201710598892 A CN 201710598892A CN 107337950 A CN107337950 A CN 107337950A
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- fluorescent paint
- epoxy resin
- salicylidene
- semicarbazides
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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
- 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
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
-
- 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
- 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
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/06—Ethers; Acetals; Ketals; Ortho-esters
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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
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
-
- 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
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/29—Compounds containing one or more carbon-to-nitrogen double bonds
-
- 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
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/29—Compounds containing one or more carbon-to-nitrogen double bonds
- C08K5/30—Hydrazones; Semicarbazones
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Paints Or Removers (AREA)
- Luminescent Compositions (AREA)
Abstract
The invention discloses fluorescent paint and preparation method thereof made of bigcatkin willow aldehydes schiff bases, two kinds of bigcatkin willow aldehydes schiff bases are respectively salicylidene semicarbazides and Salicylaldehyde glycine.The invention provides a kind of fluorescent paint using salicylidene semicarbazides as fluorescent material, it is mixed by salicylidene semicarbazides and aqueous epoxy resin emulsion, the weight of aqueous epoxy resin emulsion is 1.5 2.5 times of salicylidene semicarbazides weight.Present invention also offers a kind of fluorescent paint using Salicylaldehyde glycine as fluorescent material, it is made up of Salicylaldehyde glycine and epoxy resin, the weight of epoxy resin is 1.5 2.5 times of Salicylaldehyde glycine weight.Bigcatkin willow aldehydes schiff bases provided by the invention can be used for preparing fluorescent paint, and not only fluorescence intensity is high for preparation-obtained fluorescent paint, and organic solvent-resistant corrodes, and firm and stability is high after solidification, excellent combination property.
Description
Technical field
The invention belongs to chemical field, is related to fluorescent paint and preparation method thereof made of bigcatkin willow aldehydes schiff bases.
Background technology
Fluorescent paint refers to the coating that visible ray can be sent when being irradiated with, and just stops when stopping and irradiating
It is luminous.Fluorescent paint is to assign fluorescent functional by the fluorescent pigment in its component, in traffic route mark, building surface
The fields such as hyperchromic and biomarker are widely used, and it can change into the ultraviolet in sunshine visible ray, therefore can be with
Strengthen the brightness of coating surface.By the species point of the fluorescent pigment used, fluorescent paint includes Inorganic fluorescent paint and organic glimmering
The class of optical coating two.Luminous organic material has many advantages compared with phosphor, there is higher rub in visible region
That extinction coefficient, larger Stokes displacements, modifiability is strong and species is various etc..Therefore luminous organic material is in many fields
There is important application, such as light emitting diode (OLEDs), organic light-emitting field effect transistor (OLEFETs), organic solid laser
Device and organic fluorescence sensor.The fluorescent paint studied at present includes：1st, silicone covering type hydrolysis fluorescent material；2nd, long afterglow
Fluorescent material；3rd, the light storage type self luminous material of high efficiency rare-earth；The 4th, fluorescent dye is scattered in the melamine of para toluene sulfonamide improvement
Fluorescent pigment latex is made in amine-formaldehyde resins, the acrylic resin emulsification directly with water white transparency at a temperature of 40-50 DEG C is mixed
Close and fluorescent paint is made.5th, the contrast material using Chinese whites such as titanium dioxides as fluorescent pigment, the fluorescence to strengthening coating
With good effect.
Research Inorganic fluorescent paint is more at present, organically reports less, but both compare, and organic fluorescence prepares cost
It is low, and be a kind of fluorescent material for being worth developing the advantages that pollution without heavy metal ion with degradable.
The content of the invention
It is an object of the invention to provide application of two kinds of bigcatkin willow aldehydes schiff bases in fluorescent paint is prepared, with this two kinds
Fluorescent paint that bigcatkin willow aldehydes schiff bases is prepared and preparation method thereof.
Technical solution of the present invention is as follows：
Application of two kinds of bigcatkin willow aldehydes schiff bases in fluorescent paint is prepared shown in following chemical constitution,
A kind of fluorescent paint, it is mixed by salicylidene semicarbazides and aqueous epoxy resin emulsion, water-base epoxy tree
The weight of fat liquor is 1.5-2.5 times of salicylidene semicarbazides weight.
Preferably, fluorescence-enhancing agent triethanolamine or polyethylene glycol 400,1 gram of water are also included when prepared by the fluorescent paint
Poplar semicarbazone correspondingly adds 0.8-1.2 milliliters triethanolamine or polyethylene glycol 400.
A kind of fluorescent paint, is made up of Salicylaldehyde glycine and epoxy resin, and the weight of epoxy resin is salicylide
1.5-2.5 times of contracting glycine weight.
The preparation method of salicylidene semicarbazides fluorescent paint, comprises the following steps：First with a small amount of water by salicylidene ammonia
Base urea dissolves, then is mixed with aqueous epoxy resin emulsion, strongly stirs and uniformly produces.
The preparation method of salicylidene semicarbazides fluorescent paint, comprises the following steps：First with a small amount of water by salicylidene ammonia
Base urea dissolves, then is mixed with aqueous epoxy resin emulsion, triethanolamine or polyethylene glycol 400, strongly stirs and uniformly produces.
The preparation method of Salicylaldehyde glycine fluorescent paint, comprises the following steps：First by epoxy resin acetone solution
Epoxy resin acetone soln is made, adds Salicylaldehyde glycine, strongly stirs and uniformly produces.
Beneficial effects of the present invention：
Bigcatkin willow aldehydes schiff bases provided by the invention can be used for preparing fluorescent paint, and preparation-obtained fluorescent paint is not
But fluorescence intensity is high, and organic solvent-resistant corrodes, and firm and stability is high after solidification, excellent combination property.
Embodiment
Technical scheme is specifically introduced with reference to embodiment.
Embodiment 1：The synthesis of fluorescent pigment salicylidene semicarbazides
2.12g (0.019mol) semicarbazide hydrochlorides pH is adjusted to 7 with 1.0mol/LNaOH solution, 10ml is pipetted with pipette
Absolute ethyl alcohol, 2ml (0.019mol) salicylides are simultaneously mixed in 100ml round-bottomed flasks, in 80 DEG C of constant temperature oil baths, are stirred at reflux
React about 3h.By reaction flask to be cooled down in the large beaker equipped with frozen water, product is separated out, is filtered, absolute ethyl alcohol washing, product is put
In culture dish, drying box is moved into, obtains white powdery solids product 3.20g, yield 94%.1H NMR(CDCl3,400MHz),
δ：10.18 (s, 1H, OH), 9.96 (s, 1H ,-NH-), 8.14 (s, 1H ,-CH=N-), 7.75 (m, 1H, Ar), 7.15 (m, 1H,
Ar),6.82(d,2H,Ar),6.40(s,2H,-NH2)。
Chemical structural formula is as follows：
Embodiment 2：The synthesis of fluorescent pigment Salicylaldehyde glycine
2ml (0.019mol) salicylides are pipetted with pipette to be mixed in 100ml round-bottomed flasks with 10ml absolute ethyl alcohols, are added
Enter 1.425g (0.019mol) glycine, stirred in 50 DEG C of constant temperature oil baths, flow back about 3h.Reaction flask is cooled down with frozen water,
Product is separated out, is filtered, absolute ethyl alcohol washing, product is placed in culture dish, is dried in vacuo, is obtained pale yellow powder shape solid product
2.782g yield 82%.1H NMR(CDCl3,400MHz),δ：14.30 (s, 1H ,-COOH), 8.33 (s, 1H ,-CH=N-),
7.31(m,1H,Ar-),7.25(m,1H,Ar-),6.71(m,2H,Ar-),4.03(m,2H,-CH2-)。
Chemical structural formula is as follows：
Embodiment 3：Salicylidene semicarbazides is the preparation of the fluorescent paint of luminescent material
Fluorescent paint A：First salicylidene semicarbazides is dissolved with a small amount of water, then mixed with aqueous epoxy resin emulsion, by force
Power, which is stirred, uniformly to be produced；The weight of aqueous epoxy resin emulsion is 2 times of salicylidene semicarbazides weight.
Fluorescent paint B：First salicylidene semicarbazides is dissolved with a small amount of water, then mixed with aqueous epoxy resin emulsion, by force
Power, which is stirred, uniformly to be produced；The weight of aqueous epoxy resin emulsion is 1.5 times of salicylidene semicarbazides weight.
Fluorescent paint C：First salicylidene semicarbazides is dissolved with a small amount of water, then mixed with aqueous epoxy resin emulsion, by force
Power, which is stirred, uniformly to be produced；The weight of aqueous epoxy resin emulsion is 2.5 times of salicylidene semicarbazides weight.
Fluorescent paint D：First salicylidene semicarbazides is dissolved with a small amount of water, then with aqueous epoxy resin emulsion, three ethanol
Amine mixes, and strongly stirs and uniformly produces；The weight of aqueous epoxy resin emulsion is 2 times of salicylidene semicarbazides weight, 1 gram of water
Poplar semicarbazone 1 milliliter of triethanolamine of corresponding addition.
Fluorescent paint E：First salicylidene semicarbazides is dissolved with a small amount of water, then with aqueous epoxy resin emulsion, poly- second two
Alcohol 400 mixes, and strongly stirs and uniformly produces；The weight of aqueous epoxy resin emulsion is 2 times of salicylidene semicarbazides weight, 1
Gram salicylidene semicarbazides 1 milliliter of polyethylene glycol 400 of corresponding addition.
Wherein, when prepared by fluorescent paint D, fluorescent paint E, 1 gram of salicylidene semicarbazides correspondingly adds 0.8-1.2 milliliters three
Monoethanolamine or polyethylene glycol 400 can be remarkably reinforced fluorescence intensity.
Aqueous epoxy resin emulsion is MU-601 aqueous epoxy resin emulsions, likes that Expo organosilicon material is limited purchased from Shanghai
Company.
Embodiment 4：Salicylaldehyde glycine is the preparation of the fluorescent paint of luminescent material
Fluorescent paint F：Epoxy resin acetone soln first is made with acetone solution in epoxy resin, it is sweet to add salicylidene
Propylhomoserin, strongly stir and uniformly produce；Wherein, the weight of epoxy resin is 2 times of Salicylaldehyde glycine weight, 2g epoxy resin
It is dissolved in 3ml acetone.
Fluorescent paint G：Epoxy resin acetone soln first is made with acetone solution in epoxy resin, it is sweet to add salicylidene
Propylhomoserin, strongly stir and uniformly produce；Wherein, the weight of epoxy resin is 1.5 times of Salicylaldehyde glycine weight, 2g asphalt mixtures modified by epoxy resin
Fat is dissolved in 3ml acetone.
Fluorescent paint H：Epoxy resin acetone soln first is made with acetone solution in epoxy resin, it is sweet to add salicylidene
Propylhomoserin, strongly stir and uniformly produce；Wherein, the weight of epoxy resin is 2.5 times of Salicylaldehyde glycine weight, 2g asphalt mixtures modified by epoxy resin
Fat is dissolved in 3ml acetone.
Above-mentioned epoxy resin uses E51 epoxy resin.
Embodiment 5：Effect example
The tinplate sheet that size is 40 × 90mm is got out, with the surface of two kinds of sand paper of thickness, the good iron plate of acetone treatment.Point
Fluorescent paint A-H prepared by above-described embodiment is not coated uniformly on iron plate, 24h dries at room temperature, is finally placed in iron plate
4h film forming is dried in baking oven at 80 DEG C.After the smearing model prepared is completely dried, appearance is transparent, glossy, no gas
Bubble, good film-forming property are smooth and difficult for drop-off.Being positioned over detection under 365nm uviol lamps, (fluorescence applies it can be found that there is hanced cyan fluorescent
Material A-E) or green fluorescence (fluorescent paint F-H) send.
Fluorescent paint A-H prepared by above-described embodiment is coated uniformly on slide respectively, 24h dries at room temperature, most
Slide is placed in baking oven drying 4h film forming at 80 DEG C afterwards.Water, acetone, ethyl acetate, dichloromethane are poured into cleaning respectively
Glass culture dish, the slide after curing of coating is placed in one, taken out after 24h, find fluorescent paint A-H on slide
The film of formation does not come off after soaking 24h to the excellent corrosion resistance of aforesaid liquid, without bubble, remained unchanged smooth.
Determine fluorescent paint A, D, E photoluminescence spectrum intensity, excitation wavelength respectively with Agilent Cary100 XRFs
For 360nm, launch wavelength is 720nm, and the optical density measured is as shown in table 1.
Table 1 fluorescent paint A, D, E fluorescent intensity degree compare (using optical density as index)
| Fluorescent paint A | Fluorescent paint D | Fluorescent paint E | |
| Optical density | 450 | 640 | 655 |
The above results prove that fluorescent paint D, E fluorescence intensity are significantly higher than fluorescent paint A, illustrate triethanolamine or poly-
Ethylene glycol 400 can be remarkably reinforced the fluorescence intensity of salicylidene amino urea groups fluorescent paint.
Bigcatkin willow aldehydes schiff bases provided by the invention can be used for preparing fluorescent paint, and preparation-obtained fluorescent paint is not
But fluorescence intensity is high, and organic solvent-resistant corrodes, and firm and stability is high after solidification, excellent combination property.
The effect of above-described embodiment is only that the essentiality content of the explanation present invention, but the guarantor of the present invention is not limited with this
Protect scope.Simply modification is carried out to technical solution of the present invention or simple replacement does not depart from essence and the guarantor of technical solution of the present invention
Protect scope.
Claims (8)
1. application of two kinds of bigcatkin willow aldehydes schiff bases in fluorescent paint is prepared shown in following chemical constitution,
A kind of 2. fluorescent paint, it is characterised in that：It is mixed by salicylidene semicarbazides and aqueous epoxy resin emulsion, water
Property epoxy resin latex weight be 1.5-2.5 times of salicylidene semicarbazides weight.
3. fluorescent paint according to claim 2, it is characterised in that：Also include fluorescence-enhancing agent triethanolamine or poly- second two
400,1 gram of salicylidene semicarbazides of alcohol correspondingly adds 0.8-1.2 milliliters triethanolamine or polyethylene glycol 400.
A kind of 4. fluorescent paint, it is characterised in that：It is made up of Salicylaldehyde glycine and epoxy resin, the weight of epoxy resin
For 1.5-2.5 times of Salicylaldehyde glycine weight.
5. the preparation method of fluorescent paint described in claim 2, it is characterised in that：It is first with a small amount of water that salicylidene semicarbazides is molten
Solution, then mixed with aqueous epoxy resin emulsion, strongly stir and uniformly produce.
6. the preparation method of fluorescent paint described in claim 3, it is characterised in that：It is first with a small amount of water that salicylidene semicarbazides is molten
Solution, then mixed with aqueous epoxy resin emulsion, triethanolamine or polyethylene glycol 400, strongly stir and uniformly produce.
7. the preparation method of fluorescent paint described in claim 4, it is characterised in that：Ring first is made with acetone solution in epoxy resin
Oxygen tree fat acetone soln, adds Salicylaldehyde glycine, strongly stirs and uniformly produces.
8. the application of triethanolamine or polyethylene glycol 400 in terms of salicylidene semicarbazides fluorescence intensity is strengthened.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710598892.3A CN107337950A (en) | 2017-07-21 | 2017-07-21 | Fluorescent paint and preparation method thereof made of bigcatkin willow aldehydes schiff bases |
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| CN201710598892.3A CN107337950A (en) | 2017-07-21 | 2017-07-21 | Fluorescent paint and preparation method thereof made of bigcatkin willow aldehydes schiff bases |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108689897A (en) * | 2018-06-26 | 2018-10-23 | 南京信息工程大学 | A kind of preparation method and application of the bigcatkin willow aldehydes schiff base compounds with fluorescent characteristic |
| CN109880488A (en) * | 2019-03-15 | 2019-06-14 | 武汉工程大学 | A kind of Diamines salicylide Schiff 's base is grapheme modified or graphene oxide metal anti-corrosive paint |
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| CN102627889A (en) * | 2012-03-20 | 2012-08-08 | 江苏同辉照明科技有限公司 | Preparation method of fluorescent paint for night lampshade |
| CN103819367A (en) * | 2014-02-20 | 2014-05-28 | 桂林理工大学 | Diethylin salicylaldehyde semicarbazone and application thereof |
| PL219718B1 (en) * | 2012-06-06 | 2015-06-30 | Univ West Pomeranian Szczecin Tech | Organic salt of N-(salicylaldehyde)-L-amino acid and a method for producing an organic salt of N-(salicylaldehyde)-L-amino acid |
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| CN1135420A (en) * | 1996-01-23 | 1996-11-13 | 南开大学戈德防伪技术公司 | Anti-fake fluorescent pressure-sensitive carbon paper and making method thereof |
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| PL219718B1 (en) * | 2012-06-06 | 2015-06-30 | Univ West Pomeranian Szczecin Tech | Organic salt of N-(salicylaldehyde)-L-amino acid and a method for producing an organic salt of N-(salicylaldehyde)-L-amino acid |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108689897A (en) * | 2018-06-26 | 2018-10-23 | 南京信息工程大学 | A kind of preparation method and application of the bigcatkin willow aldehydes schiff base compounds with fluorescent characteristic |
| CN109880488A (en) * | 2019-03-15 | 2019-06-14 | 武汉工程大学 | A kind of Diamines salicylide Schiff 's base is grapheme modified or graphene oxide metal anti-corrosive paint |
| CN109880488B (en) * | 2019-03-15 | 2021-03-26 | 武汉工程大学 | Diamine salicylaldehyde schiff base modified graphene or graphene oxide metal anticorrosive paint |
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Application publication date: 20171110 |