CN107501195A - A kind of pyrimidine radicals fluorescent whitening agent of diphenyl two and preparation method and application - Google Patents
A kind of pyrimidine radicals fluorescent whitening agent of diphenyl two and preparation method and application Download PDFInfo
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- CN107501195A CN107501195A CN201710826038.8A CN201710826038A CN107501195A CN 107501195 A CN107501195 A CN 107501195A CN 201710826038 A CN201710826038 A CN 201710826038A CN 107501195 A CN107501195 A CN 107501195A
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- whitening agent
- fluorescent whitening
- diphenyl
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
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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
- C09B57/00—Other synthetic dyes of known constitution
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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
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
- D06L4/00—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
- D06L4/60—Optical bleaching or brightening
- D06L4/614—Optical bleaching or brightening in aqueous solvents
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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
- D06P1/44—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 insoluble pigments or auxiliary substances, e.g. binders
- D06P1/62—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 insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds with sulfate, sulfonate, sulfenic or sulfinic groups
- D06P1/628—Compounds containing nitrogen
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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
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/58—Material containing hydroxyl groups
- D06P3/60—Natural or regenerated cellulose
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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
- C09K2211/1007—Non-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
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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Abstract
The invention discloses a kind of pyrimidine radicals fluorescent whitening agent of diphenyl two, a kind of structural formula of the described pyrimidine radicals fluorescent whitening agent of diphenyl two is as shown in Equation 1：The present invention relates to fluorescent whitening agent technical field.Aim to provide that a kind of preparation method is simple, cheap pyrimidine radicals fluorescent whitening agent of diphenyl two of the prices of raw materials and preparation method thereof with and application.Have the function that significantly to brighten using the pyrimidine radicals fluorescent whitening agent of diphenyl two of the present invention, hyperchromic cotton fiber, be a kind of novel high-performance fluorescent whitening agent.
Description
Technical field
The present invention relates to fluorescent whitening agent technical field, the especially a kind of pyrimidine radicals of diphenyl-two fluorescent whitening agent and its
Preparation method and application.
Background technology
China has formd fairly perfect material S＆T condition, has obvious resource in some field of new materials
Advantage and technical advantage, but the overall capability of independent innovation is also weaker, the new material product and skill with independent intellectual property right
Art is also fewer, the innovative deficiency especially in terms of cotton fiber is with high-performance fluorescent whitening agent.
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
For above-mentioned deficiency, the present invention is intended to provide a kind of higher with cotton fiber surface ion combined with firmness, optimal dye
Colour saturation is relatively low, and usage amount is less, and stronger pyrimidine radicals fluorescent whitening agent of diphenyl-two of practicality and preparation method thereof is with answering
With.
To achieve these goals, technical scheme provided by the invention is：A kind of pyrimidine radicals of diphenyl-two fluorescent brightening
Agent, its structural formula are as shown in Equation 1：
A kind of preparation method of the pyrimidine radicals fluorescent whitening agent of diphenyl-two as described above, comprises the following steps：
Step 1：4,4'- diaminobenzil -2,2'- disulfonic acid aqueous solution and 2,4- dichloro pyrimidine solution are mixed,
Reaction 10~11 hours；
Step 2：Aniline is added into the reactant mixture of step 1, is reacted 7~8 hours；
Step 3：Room temperature is cooled to, sodium chloride is added, the pyrimidine radicals fluorescent whitening agent of diphenyl-two is separated out and is collected；
Wherein, the material of 4,4'- diaminobenzils -2,2'- disulfonic acid, 2,4- dichloro pyrimidines, aniline, sodium chloride
The ratio of amount is：1:2.1:1.95：17.1.
Wherein, the pH value for stating step 1 is 7~8.
Wherein, the pH value of the step 2 is 8~9.
Wherein, the reaction temperature of the step 1 is 20~25 DEG C.
Wherein, in the step 1, in 2,4- dichloro pyrimidine solution, per 10mmol 2, the corresponding 10~15mL of 4- dichloro pyrimidines
Dimethylformamide.
Wherein, in the step 1, in 4,4'- diaminobenzil -2,2'- disulfonic acid aqueous solution, per 5mmol 4,
Corresponding 50~55mL the water of 4'- diaminobenzil -2,2'- disulfonic acid.
Wherein, the pH value of 4,4'- diaminobenzil -2,2'- disulfonic acid aqueous solution described in step 1 is 5~6.
Wherein, described pH adjusting agent is 10%Na2CO3The aqueous solution.
In the preparation method of the above-mentioned pyrimidine radicals of diphenyl-two fluorescent whitening agent, in described step 1,4,4'- diaminourea
Talan -2,2'- disulfonic acid the aqueous solution is added in the form of being added dropwise in 2,4- dichloro pyrimidine solution.
A kind of pyrimidine radicals of diphenyl-two fluorescent whitening agent as described above is applied to brightening, being hyperchromic for cotton fiber.
The present invention has the advantage that compared with conventional method：
1st, the synthetic method of the pyrimidine radicals of diphenyl-two fluorescent whitening agent of the present invention is simple, and the prices of raw materials are cheap；
2nd, the pyrimidine radicals of diphenyl-two fluorescent whitening agent of the present invention 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；
3rd, the pyrimidine radicals of diphenyl-two fluorescent whitening agent of the present invention can significantly brighten, hyperchromic cotton fiber, be a kind of new
High-performance fluorescent whitening agent, there is great promotion and application space；
4th, the optical property of the pyrimidine radicals of diphenyl-two fluorescent whitening agent of the present invention is tested, it can be clearly seen that hexichol
The pyrimidine radicals of base-two fluorescent whitening agent has stronger uv absorption property.By brightening processing to cotton fiber dyeing, hexichol is found
The pyrimidine radicals of base-two fluorescent whitening agent to cotton fiber have significantly brighten, hyperchromic characteristic.
Brief description of the drawings
Fig. 1 is UV absorption in the optical performance test of the pyrimidine radicals aqueous solutions of optical brighteners of diphenyl-two of embodiment 3
Spectrogram.
Specific embodiment
The claim of the present invention is described in further detail with reference to embodiment, but not formed to this
Any restrictions of invention, still any limited modification made within the scope of the invention as claimed, the claim in the present invention
In protection domain.
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.Then plus 19.5mmol aniline, 10%Na is used2CO3The pH=9 of aqueous solution maintenance system,
Back flow reaction 8h.Two-step reaction terminal is monitored with TLC technique.Room temperature is cooled to, 10g sodium chloride is added, stirring, filters,
It is dried in vacuo to obtain the pyrimidine radicals fluorescent whitening agent of diphenyl-two, 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-
Answer the pH=8 of system, 25 DEG C of reaction 10h.Then plus 19.5mmol aniline, 10%Na is used2CO3The pH=of aqueous solution maintenance system
8, back flow reaction 7h.Two-step reaction terminal is monitored with TLC technique.Room temperature is cooled to, 10g sodium chloride is added, stirs, takes out
Filter, is dried in vacuo to obtain the pyrimidine radicals fluorescent whitening agent of diphenyl-two, 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.Then plus 19.5mmol aniline, 10%Na is used2CO3The pH=of aqueous solution maintenance system
9, back flow reaction 7h.Two-step reaction terminal is monitored with TLC technique.Room temperature is cooled to, 10g sodium chloride is added, stirs, takes out
Filter, is dried in vacuo to obtain the pyrimidine radicals fluorescent whitening agent of diphenyl-two, yield 89%.
Optical performance test
The present invention carries out optical performance test, UV absorption spectrogram such as Fig. 1 using ultraviolet-visible spectrum to product of the present invention
It is shown.
Ultraviolet-visible spectrum can be effectively tested the conjugated system of optical brightener molecules.The pyrimidine radicals of diphenyl-two 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 that diphenyl-two is phonetic
Piperidinyl fluorescent whitening agent has stronger uv absorption property, and maximal ultraviolet absorption peak is located at 352nm.
Dye and brighten experiment
The dyeing concentration of the pyrimidine radicals fluorescent whitening agent of diphenyl-two is respectively 0.05%, 0.10%, 0.15%, 0.20%
With 0.30% (o.w.f) aqueous solution, special pure cotton cloth of the processing without fluorescent whitening agent.The mass ratio of body lotion and pure cotton fiber
For 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
Minute；Take out dyed cotton fabric, cold rinse；Dry at room temperature, whiteness to be measured.
The pyrimidine radicals fluorescent whitening agent of 1 diphenyl of table-two 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 the pyrimidine radicals of diphenyl-two fluorescent whitening agent under different dyeing concentrations to cotton
Cloth be respectively provided with significantly brighten, hyperchromic effect, its optimum dyeing concentration is 0.1% (shown in table 1).In optimum dyeing concentration,
It is 131.97 by the maximum whiteness of the pure cotton cloth of treated with same.Experiment proves that the pyrimidine radicals fluorescent whitening agent of diphenyl-two is a kind of
Novel high-performance fluorescent whitening agent, there is important use value and application prospect.
Above-described is only presently preferred embodiments of the present invention, all timess made in the range of the spirit and principles in the present invention
What modifications, equivalent substitutions and improvements etc., should be included within the scope of the present invention.
Claims (10)
1. a kind of pyrimidine radicals of diphenyl-two fluorescent whitening agent, it is characterised in that its structural formula is as shown in Equation 1：
A kind of 2. preparation method of the pyrimidine radicals fluorescent whitening agent of diphenyl-two as claimed in claim 1, it is characterised in that including
Following steps：
Step 1：4,4'- diaminobenzil -2,2'- disulfonic acid aqueous solution and 2,4- dichloro pyrimidine solution are mixed, reaction
10~11 hours；
Step 2：Aniline is added into the reactant mixture of step 1, is reacted 7~8 hours；
Step 3：Room temperature is cooled to, sodium chloride is added, the pyrimidine radicals fluorescent whitening agent of diphenyl-two is separated out and is collected；
Wherein, 4,4'- diaminobenzils -2,2'- disulfonic acid, 2,4- dichloro pyrimidines, aniline, sodium chloride material amount
Ratio is：1:2.1:1.95:17.1.
A kind of 3. preparation method of the pyrimidine radicals of diphenyl-two fluorescent whitening agent according to claim 2, it is characterised in that
The pH value of the step 1 is 7~8.
A kind of 4. preparation method of the pyrimidine radicals of diphenyl-two fluorescent whitening agent according to claim 2, it is characterised in that
The pH value of the step 2 is 8~9.
A kind of 5. preparation method of the pyrimidine radicals of diphenyl-two fluorescent whitening agent according to claim 2, it is characterised in that
The reaction temperature of the step 1 is 20~25 DEG C.
A kind of 6. preparation method of the pyrimidine radicals of diphenyl-two fluorescent whitening agent according to claim 2, it is characterised in that
In the step 1, in 2,4- dichloro pyrimidine solution, per 10mmol 2, the corresponding 10~15mL dimethylformamides of 4- dichloro pyrimidines.
A kind of 7. preparation method of the pyrimidine radicals of diphenyl-two fluorescent whitening agent according to claim 2, it is characterised in that
In the step 1, in 4,4'- diaminobenzil -2,2'- disulfonic acid aqueous solution, per 5mmol 4,4'- diaminourea hexichol second
Corresponding 50~55mL the water of alkene -2,2'- disulfonic acid.
A kind of 8. preparation method of the pyrimidine radicals of diphenyl-two fluorescent whitening agent according to claim 2, it is characterised in that
The pH value of the 4,4'- diaminobenzil -2,2'- disulfonic acid aqueous solution described in step 1 is 5~6.
9. a kind of preparation method of the pyrimidine radicals of diphenyl-two fluorescent whitening agent according to claim 3 or 4, its feature exist
In described pH adjusting agent is 10%Na2CO3The aqueous solution.
10. a kind of pyrimidine radicals of diphenyl-two fluorescent whitening agent as described in claim 1-8 is any is applied to the increasing of cotton fiber
In vain, it is hyperchromic.
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| CN201710826038.8A CN107501195A (en) | 2017-09-14 | 2017-09-14 | A kind of pyrimidine radicals fluorescent whitening agent of diphenyl two and preparation method and application |
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| CN201710826038.8A CN107501195A (en) | 2017-09-14 | 2017-09-14 | A kind of pyrimidine radicals fluorescent whitening agent of diphenyl two and preparation method and application |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112252059A (en) * | 2020-10-18 | 2021-01-22 | 浙江理工大学 | Natural color cotton deepening and color fixing after-finishing agent |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4221015Y1 (en) * | 1965-05-13 | 1967-12-05 |
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2017
- 2017-09-14 CN CN201710826038.8A patent/CN107501195A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4221015Y1 (en) * | 1965-05-13 | 1967-12-05 |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112252059A (en) * | 2020-10-18 | 2021-01-22 | 浙江理工大学 | Natural color cotton deepening and color fixing after-finishing agent |
| CN112252059B (en) * | 2020-10-18 | 2021-08-13 | 浙江理工大学 | Natural color cotton deepening and color fixing after-finishing agent |
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Application publication date: 20171222 |