CN107641336B - A kind of alanine pyrimidine radicals fluorescent whitening agent and its preparation method and application - Google Patents
A kind of alanine pyrimidine radicals fluorescent whitening agent and its preparation method and application Download PDFInfo
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- CN107641336B CN107641336B CN201710943011.7A CN201710943011A CN107641336B CN 107641336 B CN107641336 B CN 107641336B CN 201710943011 A CN201710943011 A CN 201710943011A CN 107641336 B CN107641336 B CN 107641336B
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- fluorescent whitening
- alanine
- whitening agent
- pyrimidine radicals
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Abstract
The present invention provides a kind of alanine pyrimidine radicals fluorescent whitening agent, which is characterized in that a kind of alanine pyrimidine radicals fluorescent whitening agent is following structural formula 1:The purpose of the present invention is to provide a kind of alanine pyrimidine radicals fluorescent whitening agents and its preparation method and application, and this method is simple, and the prices of raw materials are cheap, and technique is environmentally protective.Cotton fiber is handled using fluorescent whitening agent of the invention, have significantly brighten, hyperchromic effect, be a kind of novel high-performance fluorescent whitening agent.
Description
Technical field
The present invention relates to fluorescent whitening agents and its preparation method and application, and in particular to a kind of alanine pyrimidine radicals fluorescence
Brightening agent and its preparation method and application.
Background technique
Cellulose fibre is mankind's dosage at most and using a kind of earliest textile material.Growth and people with population
Living standard continuous improvement, the consumption figure of the fiber also cumulative year after year, this is just cellulose fiber Wesy fluorescent whitening agent
Development provide wide space, especially in terms of the cotton fiber innovative research of high-performance fluorescent whitening agent.
Fluorescent whitening agent is a kind of fluorescent dye, also known as white dye.Fluorescent whitening agent is many kinds of, different types of
Fluorescent whitening agent has the characteristics that different physical chemistry, therefore before using fluorescent whitening agent, it is necessary to they clear use
Condition and application field.Fluorescent whitening agent has very high quantum yield, can effectively be brightened by its host material handled,
Increase gorgeous and blast.Optical brightener molecules can absorbing wavelength range in the ultraviolet light of 300~400nm or so, and launch wave
Long range 420~480nm or so blue-fluorescence, thus compensate for host material as blue light missing and caused by yellowing.
It makes one to feel that processed host material is pure whiter, more bright-coloured by making up blue light.Fluorescent whitening agent be widely used in papermaking,
Weaving, detergent, plastics, coating, ink, leather, New Building Materials.In addition, fluorescent whitening agent is used also as light-emitting diodes
Pipe, chemical sensitisation, chemical sensing material and ultraviolet absorber etc..
Traditional fluorescent whitening agent has the disadvantage that: synthesis process is cumbersome, and environmental pollution is than more serious;Former material
Costly, target compound structure is excessively complicated for material, has potential risk of toxicity;It is fine with hydrophobic fabric polyamides fiber, acetic acid
The affinity such as peacekeeping cotton fiber are poor, and dye-uptake is not high, brighten, hyperchromic performance it is bad, it is not very practical.As a kind of important
Fine chemical product, fluorescent whitening agent industrially have a wide range of applications field and good market prospects.
Summary of the invention
One of the objects of the present invention is to provide a kind of alanine pyrimidine radicals fluorescent whitening agents, and synthetic method is simple,
Low in raw material price.By the optical property for testing a kind of alanine pyrimidine radicals fluorescent whitening agent, it can be clearly seen that amino
Propionic acid pyrimidine radicals fluorescent whitening agent has stronger uv absorption property.By brightening processing to cotton fiber dyeing, amino is found
Propionic acid pyrimidine radicals fluorescent whitening agent to cotton fiber have significantly brighten, hyperchromic characteristic, be a kind of novel high-performance fluorescent brightening
Agent has great promotion and application space.
The second object of the present invention is to providing a kind of above-mentioned preparation method of alanine pyrimidine radicals fluorescent whitening agent.
The three of the object of the invention are to provide the purposes of above-mentioned alanine pyrimidine radicals fluorescent whitening agent.
First goal of the invention to realize the present invention, the invention adopts the following technical scheme: a kind of alanine pyrimidine radicals
Fluorescent whitening agent, structural formula such as formula 1:
First goal of the invention to realize the present invention, the invention adopts the following technical scheme: a kind of above-mentioned alanine is phonetic
The preparation method of piperidinyl fluorescent whitening agent, comprising the following steps:
(1) 4,4'- diaminobenzil -2,2'- disulfonic acid aqueous solution is added in 2,4- dichloro pyrimidine solution, is used
10%Na2CO3The pH value of aqueous solution maintenance system is 7~8, is stirred to react to obtain reaction mixture I at 20~25 DEG C;
(2) 3- alanine is added in the reaction mixture I, uses 10%Na2CO3The pH of aqueous solution maintenance system
Value is 8~9, and back flow reaction obtains reaction mixture II;
(3) the cooling reaction mixture II is added inorganic salts, analyses alanine pyrimidine radicals fluorescent whitening agent to room temperature
Out and collect;
Wherein, the object of 4,4'- diaminobenzil -2,2'- disulfonic acid, 2,4- dichloro pyrimidine and 3- alanine
The ratio of the amount of matter is 1:2-2.5:2-2.5.
In the step (1), in 2,4- dichloro pyrimidine solution, every 10mmol 2, the corresponding 10~15mL of 4- dichloro pyrimidine
Dimethylformamide;In 4,4'- diaminobenzil -2,2'- disulfonic acid aqueous solutions, every 5mmol 4,4'- diamino hexichol
Ethylene -2,2'- disulfonic acid corresponds to 50~55mL water;4,4'- diaminobenzil -2,2'- disulfonic acid the aqueous solution
PH value is 5~6.
The reaction time of the step (1) is 10~11 hours;The reaction time of the step (2) is 5~6 hours.
Inorganic salts in the step (3) are sodium chloride.
In the step (1), 4,4'- diaminobenzil -2,2'- disulfonic acid aqueous solutions are added in the form being added dropwise
In 2,4- dichloro pyrimidine solution.
A kind of purposes of alanine pyrimidine radicals fluorescent whitening agent of the present invention, and in particular to the alanine pyrimidine
Application of the base fluorescent whitening agent in the brightening and is hyperchromic of cotton fiber.
The invention has the following advantages that
1. the synthetic method of alanine pyrimidine radicals fluorescent whitening agent of the present invention is simple, the prices of raw materials are cheap.
2. alanine pyrimidine radicals fluorescent whitening agent of the present invention and cotton fiber surface ion combination fastness are higher, best to contaminate
Colour saturation is low, and practicability is stronger, environmentally protective.
It is a kind of novel high property 3. alanine pyrimidine radicals fluorescent whitening agent of the present invention can be brightened significantly, hyperchromic cotton fiber
It can fluorescent whitening agent.
Detailed description of the invention
Fig. 1 is UV absorption in the optical performance test of the alanine pyrimidine radicals aqueous solutions of optical brighteners of embodiment 1
Spectrum.
Specific embodiment
The present invention is described in further detail combined with specific embodiments below, but does not constitute to any limit of the invention
System, any limited modification made within the scope of the invention as claimed, still within the scope of the present invention.
Embodiment 1
21mmol 2,4- dichloro pyrimidine are added in 22mL dimethylformamide, 25 DEG C of stirrings.10mmol 4 is then added dropwise,
The mixed liquor of 4'- diaminobenzil -2,2'- disulfonic acid and 100mL distilled water, uses 10%Na2CO3Aqueous solution maintains reaction
The pH=7 of system, 25 DEG C of reaction 11h obtain reaction mixture I.It then obtains adding 22mmol 3- aminopropan in reaction mixture I
Acid uses 10%Na2CO3The pH=9 of aqueous solution maintenance system, back flow reaction 6h obtain reaction mixture II.Use TLC technique
Monitor two-step reaction terminal.Cooling reaction mixture II is added 10g sodium chloride, stirs, filter, be dried in vacuo to obtain ammonia to room temperature
Base propionic acid pyrimidine radicals fluorescent whitening agent, yield 87%.
Embodiment 2
21mmol 2,4- dichloro pyrimidine are added in 31.5mL dimethylformamide, 20 DEG C of stirrings.10mmol is then added dropwise
The mixed liquor of 4,4'- diaminobenzil -2,2'- disulfonic acid and 110mL distilled water, uses 10%Na2CO3Aqueous solution remains anti-
The pH=8 of system, 25 DEG C of reaction 10h are answered to obtain reaction mixture I.It then obtains adding 20mmol 3- amino in reaction mixture I
Propionic acid uses 10%Na2CO3The pH=8 of aqueous solution maintenance system, back flow reaction 5h obtain reaction mixture II.With thin-layer chromatography skill
Art monitors two-step reaction terminal.Cooling reaction mixture II is added 10g sodium chloride, stirs, filter, be dried in vacuo to room temperature
Alanine pyrimidine radicals fluorescent whitening agent, yield 84%.
Embodiment 3
21mmol 2,4- dichloro pyrimidine are added in 26mL dimethylformamide, 25 DEG C of stirrings.10mmol 4 is then added dropwise,
The mixed liquor of 4'- diaminobenzil -2,2'- disulfonic acid and 100mL distilled water, uses 10%Na2CO3Aqueous solution maintains reaction
The pH=7.5 of system, 25 DEG C of reaction 11h obtain reaction mixture I.It then obtains reaction mixture I and adds 21mmol 3- aminopropan
Acid uses 10%Na2CO3The pH=9 of aqueous solution maintenance system, back flow reaction 5h obtain reaction mixture II.Use TLC technique
Monitor two-step reaction terminal.Cooling reaction mixture II is added 10g sodium chloride, stirs, filter, be dried in vacuo to obtain ammonia to room temperature
Base propionic acid pyrimidine radicals fluorescent whitening agent, yield 86%.
Optical performance test
Optical performance test is carried out to product of the present invention using ultraviolet-visible spectrum, ultra-violet absorption spectrum is as shown in Figure 1.
Ultraviolet-visible spectrum can be effectively tested the conjugated system of optical brightener molecules.Alanine pyrimidine radicals is glimmering
Optical brightener is configured to the aqueous solution that concentration is 0.02g/L and carries out optical performance test.Test result shows alanine pyrimidine
Base fluorescent whitening agent has stronger uv absorption property.
Dye and brighten experiment
The dyeing concentration of alanine pyrimidine radicals fluorescent whitening agent is respectively 0.05%, 0.10%, 0.15%, 0.20% He
The aqueous solution of 0.30% (o.w.f), processing are free of the dedicated pure cotton cloth of fluorescent whitening agent.The mass ratio of bath foam and pure cotton fiber
For 50:1.In 15 minutes, temperature is warming up to 50 DEG C from 20 DEG C with 2 DEG C/min of speed;Then bath foam heat preservation is at 50 DEG C, 15
Minute;Take out dyed cotton fabric, cold rinse;It dries at room temperature, whiteness to be measured.
By whiteness test as can be seen that alanine pyrimidine radicals fluorescent whitening agent under different dyeing concentrations to cotton
All have significantly brighten, hyperchromic effect, optimum dyeing concentration be 0.1%.In optimum dyeing concentration, by treated with same
The maximum whiteness of pure cotton cloth is 128.03.Experiments have shown that alanine pyrimidine radicals fluorescent whitening agent is a kind of novel high-performance fluorescence
Brightening agent has important use value and application prospect.
Above-described is only the embodiment of the present invention, all made within the scope of the spirit and principles in the present invention any to repair
Change, equivalent replacement and improvement etc., should be included within the scope of the present invention.
Claims (3)
1. a kind of alanine pyrimidine radicals fluorescent whitening agent, which is characterized in that its structural formula such as formula 1:
2. a kind of preparation method of alanine pyrimidine radicals fluorescent whitening agent described in claim 1, which is characterized in that including with
Lower step:
(1) 4,4'- diaminobenzil -2,2'- disulfonic acid aqueous solution is added in 2,4- dichloro pyrimidine solution, with 10%
Na2CO3The pH value of aqueous solution maintenance system is 7~8, is stirred to react to obtain reaction mixture I at 20~25 DEG C;
(2) 3- alanine is added in the reaction mixture I, uses 10%Na2CO3The pH value of aqueous solution maintenance system is 8
~9, back flow reaction obtains reaction mixture II;
(3) the cooling reaction mixture II is added inorganic salts, alanine pyrimidine radicals fluorescent whitening agent is precipitated simultaneously to room temperature
It collects;
Wherein, the substance of 4,4'- diaminobenzil -2,2'- disulfonic acid, 2,4- dichloro pyrimidine and 3- alanine
The ratio of amount is 1:2-2.5:2-2.2.
3. a kind of purposes of alanine pyrimidine radicals fluorescent whitening agent described in claim 1, which is characterized in that it is used for cotton fibre
Dimension brighten and be hyperchromic in application.
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