CN110484016B - Yellow fluorescent dye and preparation method and application thereof - Google Patents
Yellow fluorescent dye and preparation method and application thereof Download PDFInfo
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- CN110484016B CN110484016B CN201910703414.3A CN201910703414A CN110484016B CN 110484016 B CN110484016 B CN 110484016B CN 201910703414 A CN201910703414 A CN 201910703414A CN 110484016 B CN110484016 B CN 110484016B
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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
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B27/00—Preparations in which the azo group is formed in any way other than by diazotising and coupling, e.g. oxidation
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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
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0079—Azoic dyestuff preparations
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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
- C09D11/00—Inks
- C09D11/50—Sympathetic, colour changing or similar inks
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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
- 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
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/004—Dyeing with phototropic dyes; Obtaining camouflage effects
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/02—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes
- D06P1/04—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes not containing metal
- D06P1/06—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes not containing metal containing acid groups
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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
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
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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
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Textile Engineering (AREA)
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- Life Sciences & Earth Sciences (AREA)
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Abstract
本发明涉及荧光染料，尤其涉及一种黄色荧光染料及其制备方法以及应用。以重量计，包括以下原料：2～10份乙二胺四乙酸、10～30份乙二胺、1～5g份1，2‑吡啶偶氮2‑萘酚。制备方法具体包括如下步骤：(1)将上述原料加水，超声混合均匀；(2)将原料液放入不锈钢反应釜，加热至180～220℃，反应4h；(3)将反应后的液混合体放入透析袋进行透析，透析2～4h；(4)使用旋转蒸发仪对混合液体进行浓缩，旋蒸温度为55～65℃；5)将上述混合液体放入超低温冰箱，冷冻24～48h。所合成的碳量子点溶液呈鲜艳的黄色，并且在紫外灯下呈现强烈的黄光，所合成的荧光几乎不衰减，形成了长效的荧光。制备方法简单方便。
The present invention relates to fluorescent dyes, in particular to a yellow fluorescent dye and its preparation method and application. By weight, it includes the following raw materials: 2-10 parts of ethylenediaminetetraacetic acid, 10-30 parts of ethylenediamine, and 1-5 g parts of 1,2-pyridineazo-2-naphthol. The preparation method specifically includes the following steps: (1) adding water to the above-mentioned raw materials, and ultrasonically mixing them uniformly; (2) putting the raw material liquid into a stainless steel reaction kettle, heating to 180-220° C., and reacting for 4 hours; (3) mixing the reacted liquid Put the body into a dialysis bag for dialysis, and dialyze for 2 to 4 hours; (4) use a rotary evaporator to concentrate the mixed liquid, and the rotary evaporation temperature is 55 to 65 °C; 5) Put the above mixed liquid into an ultra-low temperature refrigerator and freeze for 24 to 48 hours . The synthesized carbon quantum dot solution was bright yellow, and showed strong yellow light under ultraviolet light, and the synthesized fluorescence hardly decayed, forming a long-lasting fluorescence. The preparation method is simple and convenient.
Description
Technical Field
The invention relates to a fluorescent dye, in particular to a yellow fluorescent dye and a preparation method and application thereof.
Background
The fluorescent dye is a dye and can be applied to the industries of textile, printing and dyeing and the like. Because of the fluorescent characteristic, the fluorescent material can be applied to the fields of anti-counterfeiting, decoration, model construction and the like. The nano-level fluorescent dye has small dye particles, is easy to enter the tissue of a dyed object, and has the advantages of good dispersibility, uniform color and the like, thereby having wide application prospect.
The existing fluorescent dye is unstable, easy to decompose and has no long-acting property; the synthesis method, the purification method and the preservation method are very complicated and inconvenient.
201810276697.3 discloses a fluorescent dye, which uses 4-amino-3, 6-disulfo-1, 8-naphthaldehyde dipotassium salt and 0.6mol p-phenylenediamine, and has bad smell because of sulfur element contained in the synthetic raw materials. 201810694947.5 discloses a "fluorescent dye" whose raw material uses a fluorescent agent to generate fluorescence, the particles being larger. Firstly, the fluorescent dye does not belong to the nanometer level and does not have the properties of a plurality of nanometer materials; secondly, the raw materials contain sulfur element, and waste gas is generated; again, the fluorescent dyes synthesized are weak in fluorescence intensity and do not persist.
Disclosure of Invention
In order to overcome the defects of the prior art, the invention provides a yellow fluorescent dye and a preparation method and application thereof. The synthesized carbon quantum dot solution is bright yellow and presents strong yellow light under an ultraviolet lamp, and the synthesized fluorescence is hardly attenuated to form long-acting fluorescence.
In order to achieve the purpose, the invention adopts the following technical scheme:
a preparation method of a yellow fluorescent dye comprises the following raw materials in parts by weight: 2-10 parts of ethylene diamine tetraacetic acid, 10-30 parts of ethylenediamine and 1-5 parts of 1, 2-pyridylazo 2-naphthol;
the method specifically comprises the following steps:
(1) adding water into the raw materials, and uniformly mixing by ultrasonic;
(2) putting the raw material liquid into a stainless steel reaction kettle, heating to 180-220 ℃, and reacting for 4 hours;
(3) putting the reacted liquid mixture into a dialysis bag for dialysis, and dialyzing for 2-4 h;
(4) concentrating the mixed liquid by using a rotary evaporator, wherein the rotary evaporation temperature is 55-65 ℃;
(5) putting the mixed liquid into an ultra-low temperature refrigerator, and freezing for 24-48 h;
(6) and (4) putting the frozen mixed material into a freeze dryer, and freeze-drying to obtain the yellow fluorescent nano material solid.
The preparation method of the fluorescent anti-counterfeiting ink comprises the step of preparing the prepared yellow fluorescent dye into dye liquid with the concentration of 0.1-5%, namely the fluorescent anti-counterfeiting ink.
A preparation method of a fluorescent textile fabric comprises the steps of preparing a dye solution with the dye concentration of 0.1-5% from the prepared yellow fluorescent dye, and soaking the textile fabric in the dye solution for 12-24 hours to obtain the dyed fluorescent textile fabric.
A preparation method of nano fluorescent powder comprises the steps of mixing powdery yellow fluorescent dye and activated clay according to the mixing ratio of 1: 1-1: 5, and preparing a clay model with fluorescence.
Compared with the prior art, the invention has the beneficial effects that:
(1) the invention has heterocyclic ring (pyridine) and raw materials with complex structures such as benzene ring (naphthol), and uses strong alkaline reagent to destroy pyridine ring and naphthol ring, so that a very stable structure is formed at high temperature, which is beneficial to forming long-acting fluorescence. The above-mentioned fluorescence is a fluorescence observed only when irradiated under an ultraviolet lamp.
(2) The method is very simple and convenient no matter a synthesis method, a purification method or a preservation method.
(3) According to the characteristics of the fluorescent dye, the method breaks the routine, performs a series of applications, and provides a template for breakthrough practical application of the yellow fluorescent dye.
The carbon quantum dot solution synthesized by the method is bright yellow, and strong yellow light is presented under an ultraviolet lamp, and the synthesized fluorescence is hardly attenuated, so that long-acting fluorescence is formed.
Drawings
FIG. 1 is a diagram of the state of the fluorescent lamp of the yellow fluorescent dye of the present invention;
FIG. 2 is a diagram of the yellow fluorescent dye of the present invention under a UV lamp;
FIG. 3 is a graph of the ultraviolet, excitation, and emission spectra of the yellow fluorescent dye of the present invention;
FIG. 4 is a diagram of a bird of the present invention in a daylight lamp position, depicted on paper;
FIG. 5 is a view of a bird of the present invention drawn on paper under an ultraviolet lamp;
FIG. 6 is a state diagram of a school badge drawn on the paper of the present invention under a fluorescent lamp;
FIG. 7 is a view of a school badge drawn on the paper of the present invention under an ultraviolet lamp;
FIG. 8 is a state diagram of the present invention under daylight lamp with numbers written on the coin;
FIG. 9 is a view of the present invention showing the writing of numbers on a coin under a UV lamp;
FIG. 10 is a comparison of dyed fabric using the present invention and undyed fabric without the present invention under fluorescent light;
FIG. 11 is a graph comparing the use of the present invention to dye a fabric with the absence of the present invention under a UV lamp;
FIG. 12 is a state diagram of a fluorescent lamp with an artwork made using the present invention;
fig. 13 is a view of an artwork made using the present invention under a uv lamp.
Detailed Description
The following further illustrates embodiments of the invention, but is not intended to limit the scope thereof:
a yellow fluorescent dye comprises the following raw materials in parts by weight: 0.2 to 1g of ethylenediaminetetraacetic acid, 1 to 3ml of ethylenediamine, and 0.01 to 0.05g of 1, 2-pyridylazo 2-naphthol.
A preparation method of yellow fluorescent dye specifically comprises the following steps:
(1) adding water into the raw materials, fixing the volume to 20ml, and uniformly mixing by ultrasonic;
(2) putting the raw material liquid into a stainless steel reaction kettle, heating to 180-220 ℃, and reacting for 4 hours;
(3) putting the reacted liquid mixture into a dialysis bag for dialysis, and dialyzing for 2-4 h;
(4) concentrating the mixed liquid by using a rotary evaporator, wherein the rotary evaporation temperature is 55-65 ℃;
(5) putting the mixed liquid into an ultra-low temperature refrigerator, and freezing for 24-48 h;
(6) and (4) putting the frozen mixed material into a freeze dryer, and freeze-drying to obtain the yellow fluorescent nano material solid.
Fig. 1 is a state diagram of a yellow fluorescent dye under a fluorescent lamp, fig. 2 is a state diagram of the yellow fluorescent dye under an ultraviolet lamp, and fig. 3 is a spectrum diagram of the yellow fluorescent dye. Therefore, the carbon quantum dot solution synthesized by the method has bright yellow color and strong yellow light under an ultraviolet lamp.
Example 1:
a yellow fluorescent dye has the following applications:
fluorescent anti-fake ink
The prepared yellow fluorescent nano fluorescent dye is prepared into a solution with the dye concentration of 0.1-5%, and a pen refill is used for absorbing dye liquid, so that writing can be performed on white paper or coins.
As shown in fig. 4-9, fig. 4 is a state diagram of a bird drawn on paper under a fluorescent lamp according to the present invention; FIG. 5 is a view of a bird of the present invention drawn on paper under an ultraviolet lamp; FIG. 6 is a state diagram of a school badge drawn on the paper of the present invention under a fluorescent lamp; FIG. 7 is a view of a school badge drawn on the paper of the present invention under an ultraviolet lamp; FIG. 8 is a state diagram of the present invention under daylight lamp with numbers written on the coin; fig. 9 is a view of the state of the numbers written on the money of the present invention under the ultraviolet lamp.
The prepared yellow fluorescent nano fluorescent dye is prepared into solution, and a pen refill is used for absorbing dye liquid, so that writing and drawing can be performed on white paper or coins. The mark is not clear under sunlight, the identification is difficult, the mark is clear and visible under an ultraviolet lamp and presents strong yellow light, and the synthesized fluorescence is hardly attenuated to form long-acting fluorescence.
Example 2:
a yellow fluorescent dye has the following applications:
application of yellow fluorescent dye in textile
And (3) preparing the prepared yellow nano fluorescent dye into dye liquid with the dye concentration of 0.1-5%, and soaking the textile fabric in the dye liquid for 12-24 hours to obtain the dyed fluorescent textile fabric.
As shown in fig. 10 and 11, fig. 10 is a graph comparing the dyeing on the cloth using the present invention and the non-dyeing under the daylight lamp without using the present invention; FIG. 11 is a graph comparing the dyeing on a cloth using the present invention with the undyed cloth without the present invention under an ultraviolet lamp. The dyed fluorescent textile fabric emits fluorescence under an ultraviolet lamp.
Example 3:
a yellow fluorescent dye has the following applications:
application of nano fluorescent powder
Mixing the powdery nano fluorescent powder with activated clay to prepare the clay model with fluorescence.
As shown in fig. 12 and 13, fig. 12 is a state diagram of a handicraft article manufactured by using the invention under a fluorescent lamp; fig. 13 is a view of an artwork made using the present invention under a uv lamp. The handicraft made by the invention emits fluorescence under an ultraviolet lamp.
The invention has heterocyclic ring (pyridine) and raw materials with complex structures such as benzene ring (naphthol), and uses strong alkaline reagent to destroy pyridine ring and naphthol ring, so that a very stable structure is formed at high temperature, which is beneficial to forming long-acting fluorescence. The above-mentioned fluorescence is a fluorescence observed only when irradiated under an ultraviolet lamp.
The method is very simple and convenient no matter a synthesis method, a purification method or a preservation method.
According to the characteristics of the fluorescent dye, the method breaks the routine, performs a series of applications, and provides a template for breakthrough practical application of the yellow fluorescent dye.
The carbon quantum dot solution synthesized by the method is bright yellow, and strong yellow light is presented under an ultraviolet lamp, and the synthesized fluorescence is hardly attenuated, so that long-acting fluorescence is formed. And the method is very simple and convenient no matter a synthesis method, a purification method or a preservation method.
The above description is only for the preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art should be considered to be within the technical scope of the present invention, and the technical solutions and the inventive concepts thereof according to the present invention should be equivalent or changed within the scope of the present invention.
Claims (4)
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001027331A2 (en) * | 1999-10-12 | 2001-04-19 | Transgenomic, Inc. | Detection of nucleic acid heteroduplex molecules by anion-exchange chromatography |
| CN101575461A (en) * | 2008-05-09 | 2009-11-11 | 上海安诺其纺织化工股份有限公司 | Sea island ultra-fine fiber dark-brown polyester dispersion dye with high color deepening capability and color fastness |
| CN104343022A (en) * | 2014-11-05 | 2015-02-11 | 北京泛博化学股份有限公司 | Fluorescent dye and preparation method and application thereof |
| CN104671347A (en) * | 2013-12-02 | 2015-06-03 | 青岛浩泰水务有限公司 | Ion exchange resin for treating and recovering copper-containing wastewater |
-
2019
- 2019-07-31 CN CN201910703414.3A patent/CN110484016B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001027331A2 (en) * | 1999-10-12 | 2001-04-19 | Transgenomic, Inc. | Detection of nucleic acid heteroduplex molecules by anion-exchange chromatography |
| CN101575461A (en) * | 2008-05-09 | 2009-11-11 | 上海安诺其纺织化工股份有限公司 | Sea island ultra-fine fiber dark-brown polyester dispersion dye with high color deepening capability and color fastness |
| CN104671347A (en) * | 2013-12-02 | 2015-06-03 | 青岛浩泰水务有限公司 | Ion exchange resin for treating and recovering copper-containing wastewater |
| CN104343022A (en) * | 2014-11-05 | 2015-02-11 | 北京泛博化学股份有限公司 | Fluorescent dye and preparation method and application thereof |
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