CN107602485A - A kind of pyrimidine morpholinyl fluorescent whitening agent and its preparation method and application - Google Patents
A kind of pyrimidine morpholinyl fluorescent whitening agent and its preparation method and application Download PDFInfo
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- CN107602485A CN107602485A CN201710825950.1A CN201710825950A CN107602485A CN 107602485 A CN107602485 A CN 107602485A CN 201710825950 A CN201710825950 A CN 201710825950A CN 107602485 A CN107602485 A CN 107602485A
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- pyrimidine
- morpholinyl
- whitening agent
- fluorescent whitening
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Abstract
The present invention provides a kind of pyrimidine morpholinyl fluorescent whitening agent, and its structural formula is as shown in Equation 1.The present invention also provides the preparation method and application of the pyrimidine morpholinyl fluorescent whitening agent.The pyrimidine morpholinyl fluorescent whitening agent has the function that significantly to brighten, hyperchromic cotton fiber, is a kind of novel high-performance fluorescent whitening agent, and it is prepared, and prices of raw materials are cheap, and cost is low.
Description
Technical field
The present invention relates to fluorescent whitening agent and its preparation method and application, and in particular to a kind of pyrimidine-morpholinyl fluorescence increases
White agent and its preparation method and application.
Background technology
China in the planning of " 12 " new material development using develop with resource, environmental harmony new material as mainly examining
Core index, solves the problems, such as shortage of resources by developing new material.China has formd fairly perfect material S&T condition,
There is obvious resources advantage and technical advantage in some field of new materials, but the overall capability of independent innovation is also weaker, tool
There are new material product and the technology of independent intellectual property right also fewer, especially in terms of cotton fiber is with high-performance fluorescent whitening agent
Innovative deficiency.
Fluorescent whitening agent is a kind of fluorescent dye, also known as white dye.Fluorescent whitening agent species is various, different types of
Fluorescent whitening agent has different physical chemistry features, therefore before using fluorescent whitening agent, it is necessary to they clear and definite use
Condition and application field.Fluorescent whitening agent has very high quantum yield, can effectively be brightened by the host material of its processing,
Increase gorgeous and blast.Optical brightener molecules can absorbing wavelength scope in 300~400nm or so ultraviolet light, and launch ripple
Long scope 420~480nm or so blue-fluorescence, so as to compensate for host material due to blue light missing and caused by yellowing.
Make 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, has potential risk of toxicity for material;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, practicality is not strong.As a kind of important
Fine chemical product, fluorescent whitening agent industrially have a wide range of applications field and good market prospects.
The content of the invention
An object of the present invention is to provide a kind of pyrimidine-morpholinyl fluorescent whitening agent, and its synthetic method is simple, raw material
It is cheap.By the optical property for testing pyrimidine-morpholinyl fluorescent whitening agent, it can be clearly seen that pyrimidine-morpholinyl fluorescence
Brightening agent has stronger uv absorption property.By brightening processing to cotton fiber dyeing, pyrimidine-morpholinyl fluorescent brightening is found
Agent to cotton fiber have significantly brighten, hyperchromic characteristic, be a kind of novel high-performance fluorescent whitening agent, have greatly promote with
Application space.
The two of the object of the invention are to provide the preparation method of above-mentioned pyrimidine-morpholinyl fluorescent whitening agent.
The three of the object of the invention are to provide the purposes of above-mentioned pyrimidine-morpholinyl fluorescent whitening agent.
To realize first goal of the invention of the invention, the present invention uses following technical scheme:A kind of pyrimidine-morpholinyl fluorescence
Brightening agent, its structural formula such as formula 1:
To realize first goal of the invention of the invention, the present invention uses following technical scheme:A kind of above-mentioned pyrimidine-morpholinyl
The preparation method of fluorescent whitening agent, comprises the following steps:
(1) 4,4'- diaminobenzil -2,2'- disulfonic acid aqueous solution is added in 2,4- dichloro pyrimidine solution, used
10%Na2CO3The pH value of aqueous solution maintenance system is 7~8, and reactant mixture I is obtained in 20~25 DEG C of stirring reactions;
(2) morpholine is added in the reactant mixture I, uses 10%Na2CO3The pH value of aqueous solution maintenance system be 8~
9, back flow reaction obtains reactant mixture II;
(3) the reactant mixture II is cooled down to room temperature, is added inorganic salts, is separated out pyrimidine-morpholinyl fluorescent whitening agent
And collect;
Wherein, the amount of the material of 4,4'- diaminobenzils -2,2'- disulfonic acid, 2,4- dichloro pyrimidines and morpholine
Ratio be 1:2-2.5:1.5-2.
In described step (1), in 2,4- dichloro pyrimidine solution, per 10mmol 2, the corresponding 10~15mL of 4- dichloro pyrimidines
Dimethylformamide;In 4,4'- diaminobenzil -2,2'- disulfonic acid aqueous solution, per 5mmol 4,4'- diaminourea hexichol
Corresponding 50~55mL the water of ethene -2,2'- disulfonic acid;The described 4,4'- diaminobenzil -2,2'- disulfonic acid aqueous solution
PH value is 5~6.
The reaction time of the step (1) is 10~11 hours;The reaction time of described step (2) is 7~8 hours.
Inorganic salts in the step (3) are sodium chloride.
In the step (1), 4,4'- diaminobenzil -2,2'- disulfonic acid aqueous solution are added in the form of being added dropwise
In 2,4- dichloro pyrimidine solution.
The purposes of pyrimidine of the present invention-morpholinyl fluorescent whitening agent, and in particular to the pyrimidine-morpholinyl fluorescent brightening
Application of the agent in the brightening and be hyperchromic of cotton fiber.
The present invention has advantages below:
1. the synthetic method of pyrimidine of the present invention-morpholinyl fluorescent whitening agent is simple, the prices of raw materials are cheap.
2. pyrimidine of the present invention-morpholinyl fluorescent whitening agent and cotton fiber surface ion combined with firmness are higher, optimum dyeing
Concentration is relatively low, and usage amount is less, and practicality is stronger.
It is that a kind of novel high-performance is glimmering 3. pyrimidine of the present invention-morpholinyl fluorescent whitening agent can be brightened significantly, hyperchromic cotton fiber
Optical brightener.
Brief description of the drawings
Fig. 1 is the proton nmr spectra of pyrimidine-morpholinyl fluorescent whitening agent of embodiment 3;
Fig. 2 is ultraviolet absorption spectrum in the optical performance test of pyrimidine-morpholinyl aqueous solutions of optical brighteners of embodiment 3.
Specific embodiment
With reference to specific embodiment, the present invention is described in further detail, but does not form any limit to the present invention
System, any limited modification made within the scope of the invention as claimed, still in the claims of the present invention.
Embodiment 1
21mmol 2,4- dichloro pyrimidine are added in 22mL dimethylformamides, 25 DEG C of stirrings.10mmol 4 is then added dropwise,
The mixed liquor of 4'- diaminobenzils -2,2'- disulfonic acid and 100mL distilled water, uses 10%Na2CO3Aqueous solution maintenance reaction
The pH=7 of system, 25 DEG C of reaction 11h obtain reactant mixture I.Then obtain adding 19.5mmol morpholines in reactant mixture I, use
10%Na2CO3The pH=9 of aqueous solution maintenance system, back flow reaction 7h obtain reactant mixture II.Monitored with TLC technique
Two-step reaction terminal.Reactant mixture II is cooled down to room temperature, adds 10g sodium chloride, is stirred, is filtered, be dried in vacuo pyrimidine-
Quinoline base fluorescent whitening agent, yield 91%.
Embodiment 2
21mmol 2,4- dichloro pyrimidine are added in 31.5mL dimethylformamides, 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%Na2CO3The aqueous solution remains anti-
The pH=8 of system, 25 DEG C of reaction 10h are answered to obtain reactant mixture I.Then obtain adding 19.5mmol morpholines in reactant mixture I,
Use 10%Na2CO3The pH=8 of aqueous solution maintenance system, back flow reaction 8h obtain reactant mixture II.Supervised with TLC technique
Survey two-step reaction terminal.Reactant mixture II is cooled down to room temperature, adds 10g sodium chloride, is stirred, is filtered, be dried in vacuo pyrimidine-
Morpholinyl fluorescent whitening agent, yield 87%.
Embodiment 3
21mmol 2,4- dichloro pyrimidine are added in 26mL dimethylformamides, 25 DEG C of stirrings.10mmol 4 is then added dropwise,
The mixed liquor of 4'- diaminobenzils -2,2'- disulfonic acid and 100mL distilled water, uses 10%Na2CO3Aqueous solution maintenance reaction
The pH=7.5 of system, 25 DEG C of reaction 11h obtain reactant mixture I.Then obtain reactant mixture I and add 19.5mmol morpholines, use
10%Na2CO3The pH=9 of aqueous solution maintenance system, back flow reaction 7h obtain reactant mixture II.Monitored with TLC technique
Two-step reaction terminal.Reactant mixture II is cooled down to room temperature, adds 10g sodium chloride, is stirred, is filtered, be dried in vacuo pyrimidine-
Quinoline base fluorescent whitening agent, yield 89%.
The hydrogen nuclear magnetic resonance modal data of the pyrimidine of embodiment 3-morpholinyl fluorescent whitening agent:(400MHz;DMSO-d6,δ):
3.04~3.80 (16H, morpholine rings), 6.45 (2H, pyrimidine rings), 7.68 (4H, phenyl ring), 7.86 (2H, phenyl ring), 8.07 (2H, CH
=CH), 8.45 (2H, pyrimidine rings), 9.64 (2H, NH).
Proton nmr spectra, see Fig. 1.
Optical performance test
Optical performance test is carried out to product of the present invention using ultraviolet-visible spectrum, ultraviolet absorption spectrum is as shown in Figure 2.
Ultraviolet-visible spectrum can be effectively tested the conjugated system of optical brightener molecules.Pyrimidine-morpholinyl fluorescence increases
White agent is configured to the aqueous solution that concentration is 0.02g/L and carries out optical performance test.Test result shows, pyrimidine-morpholinyl fluorescence
Brightening agent has stronger uv absorption property, and maximal ultraviolet absorption peak is located at 354nm.
Dye and brighten experiment
The dyeing concentration of pyrimidine-morpholinyl fluorescent whitening agent is respectively 0.05%, 0.10%, 0.15%, 0.20% He
0.30% (o.w.f) aqueous solution, special pure cotton cloth of the processing without fluorescent whitening agent.Body lotion and the mass ratio of pure cotton fiber are
50:1.In 15 minutes, temperature is warming up to 50 DEG C with 2 DEG C/min of speed from 20 DEG C;Then body lotion insulation is at 50 DEG C, 15 points
Clock;Take out dyed cotton fabric, cold rinse;Dry at room temperature, whiteness to be measured.
1 pyrimidine of table-morpholinyl fluorescent whitening agent is under different dyeing concentrations to the whitening effect of cotton
Note:o.w.f:The percentage by weight of dyestuff and cotton fiber;Whiteness:Whiteness value;L*:Brightness value;a*:Red green
Value;b*:Yellow blue value.
By whiteness test as can be seen that pyrimidine-morpholinyl fluorescent whitening agent is equal to cotton under different dyeing concentrations
With significantly brighten, hyperchromic effect, its optimum dyeing concentration is 0.1% (shown in table 1).In optimum dyeing concentration, by it
The maximum whiteness of treated pure cotton cloth is 135.04.Experiment proves that pyrimidine-morpholinyl fluorescent whitening agent is a kind of new high property
Energy fluorescent whitening agent, has important use value and application prospect.
Above-described is only embodiments of the invention, it is all made in the range of the spirit and principles in the present invention any repair
Change, equivalent substitution and improvement etc., should be included within the scope of the present invention.
Claims (8)
- A kind of 1. pyrimidine-morpholinyl fluorescent whitening agent, it is characterised in that its structural formula such as formula 1:
- 2. the preparation method of pyrimidine-morpholinyl fluorescent whitening agent described in claim 1, it is characterised in that comprise the following steps:(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, and reactant mixture I is obtained in 20~25 DEG C of stirring reactions;(2) morpholine is added in the reactant mixture I, uses 10%Na2CO3The pH value of aqueous solution maintenance system is 8~9, is returned Stream reaction obtains reactant mixture II;(3) the reactant mixture II is cooled down to room temperature, is added inorganic salts, pyrimidine-morpholinyl fluorescent whitening agent is separated out and is received Collection;Wherein, the ratio of the amount of the material of 4,4'- diaminobenzils -2,2'- disulfonic acid, 2,4- dichloro pyrimidines and morpholine Example is 1:2-2.5:1.5-2.
- 3. the preparation method of pyrimidine according to claim 2-morpholinyl fluorescent whitening agent, it is characterised in that described step Suddenly in (1), in 2,4- dichloro pyrimidine solution, per 10mmol 2, the corresponding 10~15mL dimethylformamides of 4- dichloro pyrimidines;4, In 4'- diaminobenzil -2,2'- disulfonic acid aqueous solution, per 5mmol 4,4'- diaminobenzil -2,2'- disulfonic acid Corresponding 50~55mL water.
- 4. the preparation method of pyrimidine according to claim 2-morpholinyl fluorescent whitening agent, it is characterised in that described step Suddenly in (1), the pH value of 4,4'- diaminobenzil -2,2'- disulfonic acid aqueous solution is 5~6.
- 5. the preparation method of pyrimidine according to claim 2-morpholinyl fluorescent whitening agent, it is characterised in that the step (1) reaction time is 10~11 hours;The reaction time of the step (2) is 7~8 hours.
- 6. the preparation method of pyrimidine according to claim 2-morpholinyl fluorescent whitening agent, it is characterised in that described step Suddenly the inorganic salts in (3) are sodium chloride.
- 7. the preparation method of pyrimidine according to claim 2-morpholinyl fluorescent whitening agent, it is characterised in that described step Suddenly in (1), it is molten that 4,4'- diaminobenzil -2,2'- disulfonic acid aqueous solution are added to 2,4- dichloro pyrimidines in the form of being added dropwise In liquid.
- 8. the application of pyrimidine-morpholinyl fluorescent whitening agent described in claim 1 in the brightening and be hyperchromic of cotton fiber.
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Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4221015Y1 (en) * | 1965-05-13 | 1967-12-05 | ||
CN104312197B (en) * | 2014-09-05 | 2016-09-21 | 旭泰(太仓)精细化工有限公司 | A kind of hexa-sulphonic acid liquid fluorescent whitening agents and preparation method and application |
-
2017
- 2017-09-14 CN CN201710825950.1A patent/CN107602485A/en active Pending
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4221015Y1 (en) * | 1965-05-13 | 1967-12-05 | ||
CN104312197B (en) * | 2014-09-05 | 2016-09-21 | 旭泰(太仓)精细化工有限公司 | A kind of hexa-sulphonic acid liquid fluorescent whitening agents and preparation method and application |
Non-Patent Citations (1)
Title |
---|
陈荣圻: "《染料化学》", 31 December 1989, 纺织工业出版 * |
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Application publication date: 20180119 |