CN107337651A - A kind of multi-functional quaternary cationics and its preparation method and application - Google Patents

A kind of multi-functional quaternary cationics and its preparation method and application Download PDF

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Publication number
CN107337651A
CN107337651A CN201710461484.3A CN201710461484A CN107337651A CN 107337651 A CN107337651 A CN 107337651A CN 201710461484 A CN201710461484 A CN 201710461484A CN 107337651 A CN107337651 A CN 107337651A
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China
Prior art keywords
functional quaternary
quaternary cationics
preparation
feature exist
functional
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CN201710461484.3A
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万茂生
画莉
曾文
曾一文
李梅
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Hezhou University
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Hezhou University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/40—Nitrogen atoms
    • C07D251/54—Three nitrogen atoms
    • C07D251/70—Other substituted melamines
    • 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
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
    • D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
    • D21H21/30—Luminescent or fluorescent substances, e.g. for optical bleaching

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Paper (AREA)

Abstract

The invention discloses a kind of synthesis and its application of multi-functional quaternary cationics, and the multi-functional quaternary cationics has stronger whitening effect to paper, while also has the function that to significantly reduce water surface tension.The simple synthetic method of multi-functional quaternary cationics, the prices of raw materials are cheap, safety simple to operate.The structural formula of described multi-functional quaternary cationics is as follows：The application of the multi-functional quaternary cationics in terms of paper is brightened with surfactant.

Description

A kind of multi-functional quaternary cationics and its preparation method and application
Technical field
The invention belongs to fluorescent whitening agent technical field, especially a kind of multi-functional quaternary cationics and Its preparation method and application.
Background technology
China is in the planning of " 12 " new material development by research and development and resource, the material of environmental harmony and mitigation Environmental pollution and be advantageous to the material of regeneration as main performance assessment criteria.Solved by developing new material science and technology Shortage of resources and problem of environmental pollution, China has formd fairly perfect material S＆T condition, in the research and development side of Material Field Face achieves rapid progress, and some field of new materials have obvious a resources advantage and technical advantage, but the capability of independent innovation compared with It is weak, have the new material product of independent intellectual property right and technology less, the novelty especially in terms of polyfunctional surfactant Deficiency.
Fluorescent whitening agent is a kind of dyestuff that can launch fluorescence, also known as white dye, is a kind of baroque big point Sub- organic compound.Fluorescent whitening agent has very high quantum yield, processed matrix can be brightened effectively, increase it is gorgeous. Optical brightener molecules have larger conjugated system, can absorbing wavelength scope 300~400nm or so ultraviolet light, and Launch blue-fluorescence of the wave-length coverage in 420~450nm or so, so as to compensate in matrix due to blue light missing and caused by Visual yellowing.Make one to feel that processed matrix is pure whiter, more bright-coloured by making up blue light.Fluorescent whitening agent is by widely For the numerous areas such as papermaking, weaving, detergent, plastics, paint, coating, ink, leather, ultraviolet absorber, developer, city Field demand is very huge.
The molecule that surfactant molecule is made up of hydrophilic group and hydrophobic group, including ionic and non-ionic surface are lived Property agent.Ionic surfactant is divided into cationic, anionic and amphoteric surfactant again.Surfactant can be obvious The surface tension of solvent is reduced, changes the interface the Nomenclature Composition and Structure of Complexes of system, produces wetting, emulsification, washing, scattered, solubilising, hydrotropy Etc. performance, therefore in numerous areas such as bioengineering, material science, daily-use chemical industry, food industry, oil exploitation, environmental protection Have a wide range of applications.With the development of society and the continuous progress of science and technology, the mankind have more urgent to multipurpose surfactant Demand.
Therefore, research and develop novel and multifunctional quaternary cationics turns into relevant industries important research One of hold.By scientific and technical innovation, the application field and the market competitiveness of quaternary cationics are expanded, for energy-conservation Emission reduction, structure harmony can have very important significance.
The content of the invention
For above-mentioned deficiency, the present invention is intended to provide a kind of multi-functional quaternary cationics and its preparation side Method and application, the multi-functional quaternary cationics have stronger whitening effect to paper, while also have notable Reduce the effect of water surface tension.The simple synthetic method of multi-functional quaternary cationics, the prices of raw materials are low It is honest and clean, safety simple to operate.
In order to realize above-mentioned technique effect, technical scheme provided by the invention is such：A kind of multi-functional quaternary ammonium salt sun Ionic surface active agent, the structural formula of described multi-functional quaternary cationics are as follows：
A kind of a kind of preparation method of multi-functional quaternary cationics as described above, successively including following Step：
Step 1：The Cyanuric Chloride of 2 parts of moles is added to the 4,4'- diaminobenzils -2,2'- two of 1 part of mole In the sulfonic acid aqueous solution, stirring, 2h is reacted；
Step 2：The ertiary amine solution of dimethyl 14 of 2 parts of moles is added in the solution obtained by step 1, reacts 4h；
Step 3：The 2- amion acetic acids of 2 parts of moles are added in the solution obtained by step 2, react 6h；
Step 4：100mL sodium-chloride water solutions are added in the solution obtained by step 3, multi-functional quaternary ammonium salt cationic surface Activating agent is separated out and collected.
Preferably, the reaction temperature of described step 1 is 0~5 DEG C, and pH is 3~4.
Preferably, the reaction temperature of described step 2 is 30~40 DEG C, and pH is 7~8.
Preferably, the reaction temperature of described step 3 is 90~100 DEG C, and pH is 9~10.
Preferably, the reaction temperature of described step 4 is 25~30 DEG C.
Preferably, the dosage of sodium-chloride water solution is 100mL in described step 4.
Preferably, the solvent of the described ertiary amine solution of dimethyl 14 is acetone.
Preferably, described pH value passes through Na2CO3Regulation.
A kind of multi-functional quaternary cationics as described above, the multi-functional quaternary ammonium salt cationic surface are lived Application of the property agent in terms of paper is brightened with surfactant.
The present invention has advantages below compared with conventional method：
1. effectively chemistry can occur with paper surface molecule for a kind of multi-functional quaternary cationics of the present invention Bonding, combined with firmness are high.
2. a kind of multi-functional quaternary cationics of the present invention can notable whitening paper.
3. a kind of multi-functional quaternary cationics of the present invention has stronger surface-active, can significantly reduce The surface tension of water.
Brief description of the drawings
Fig. 1 is a kind of hydrogen nuclear magnetic resonance spectrogram of multi-functional quaternary cationics of embodiment 1；
Fig. 2 is a kind of concentration of multi-functional quaternary cationics of embodiment 1 and shows length tension relation figure.
Embodiment
With reference to embodiment, the claim of the present invention is described in further detail, but not formed pair Any restrictions of the present invention, any limited number of time modification made in the claims in the present invention protection domain, still the present invention's In claims.
Embodiment 1
5mmol4,4'- diaminobenzil -2,2'- disulfonic acid mix with 100mL distilled water, stirring, 5 DEG C of ice bath, and 10mmol Cyanuric Chlorides, stirring, with saturation Na are added afterwards2CO3The pH of solution maintenance reaction system is 3, temperature control reaction 2h；It is added dropwise The tertiary amine of 10mmol dimethyl 14 and 5mL acetone mixtures, temperature reaction system is to 30 DEG C, stirring, with saturation Na2CO3Solution is tieed up The pH for holding reaction system is 7, temperature control reaction 4h；10mmol2- amion acetic acids are then added, are heated up 90 DEG C, saturation Na is added dropwise2CO3 The pH of solution maintenance reaction system is 9, temperature control reaction 6h.Room temperature is cooled to, adds 100mL saturated sodium-chloride water solutions, stir, Filter, be dried in vacuo to obtain a kind of multi-functional quaternary cationics, yield 92%.
Embodiment 2
5mmol4,4'- diaminobenzil -2,2'- disulfonic acid mix with 150mL distilled water, stirring, 0 DEG C of ice bath, and 10mmol Cyanuric Chlorides, stirring, with saturation Na are added afterwards2CO3The pH of solution maintenance reaction system is 4, temperature control reaction 2h；It is added dropwise The tertiary amine of 10mmol dimethyl 14 and 4mL acetone mixtures, temperature reaction system is to 40 DEG C, stirring, with saturation Na2CO3Solution is tieed up The pH for holding reaction system is 6, temperature control reaction 4h；10mmol2- amion acetic acids are then added, are heated up 100 DEG C, saturation Na is added dropwise2CO3 The pH of solution maintenance reaction system is 8, temperature control reaction 6h.Room temperature is cooled to, adds 100mL saturated sodium-chloride water solutions, stir, Filter, be dried in vacuo to obtain a kind of multi-functional quaternary cationics, yield 89%.
Embodiment 3
5mmol4,4'- diaminobenzil -2,2'- disulfonic acid mix with 125mL distilled water, stirring, 3 DEG C of ice bath, and 10mmol Cyanuric Chlorides, stirring, with saturation Na are added afterwards2CO3The pH of solution maintenance reaction system is 3.5, temperature control reaction 2h；Drop Add the tertiary amine of 10mmol dimethyl 14 and 6mL acetone mixtures, temperature reaction system is to 35 DEG C, stirring, with saturation Na2CO3Solution The pH of maintenance reaction system is 6.5, temperature control reaction 4h；10mmol2- amion acetic acids are then added, are heated up 95 DEG C, saturation is added dropwise Na2CO3The pH of solution maintenance reaction system is 8.5, temperature control reaction 6h.Room temperature is cooled to, it is water-soluble to add 100mL saturated sodium-chlorides Liquid, stirring, filter, be dried in vacuo to obtain a kind of multi-functional quaternary cationics, yield 90%.
Structured testing
Hydrogen modal data (400MHz；DMSO-d6,δ):10.72 (2H, NH), 9.24 (2H, NH), 8.03~7.57 (8H, ArH), 4.93 (4H, CH2), 3.31 (4H, CH2), 2.70 (12H, CH3), 1.54~0.83 (54H, (CH2)12CH3)。
Proton nmr spectra is shown in Fig. 1.
Filter paper whitening performance is tested
Respectively with the mass fraction of multi-functional quaternary cationics and filter paper be 0.1%, 0.2%, 0.25% and 0.3% processing filter paper, bath raio 1:50, room temperature dyeing 30min, filter paper is taken out, cold water washs 3 times, naturally dry, Test whiteness value.The results show, under different dyeing concentrations, multi-functional quaternary cationics is to filter paper All there is significant whitening effect.When dyeing concentration is 0.2%, the filter paper brightness after processing is maximum, and concentration is more than Or less than 0.2%, the filter paper whiteness value after processing decreases, and experimental result is shown in Table 1.
Under the coloured differently concentration of table 1, the whiteness value of filter paper after processing
Concentration 0 0.1% 0.2% 0.25% 0.3%
Whiteness value 81.89 93.46 99.02 97.54 95.32
Surface-active is tested
Surface-active test has been carried out to the aqueous solution of multi-functional quaternary cationics using suspension ring method, it is real Result to be tested to show, multi-functional quaternary cationics can significantly reduce the surface tension of water in low concentration, It is 4.0 × 10 in critical micelle concentration with excellent surface-active-4During mol/L, the aqueous solution shows that tension force is 33.32mN/ m.Concentration is with showing that length tension relation figure is shown in Fig. 2.The multi-functional quaternary cationics, which has concurrently, brightens filter paper and reduction The effect of the surface tension of water, it is a kind of multi-functional quaternary cationics, there is wide application value and push away Wide space.
The foregoing is only presently preferred embodiments of the present invention, it is all done in the range of the spirit and principles in the present invention it is any Modifications, equivalent substitutions and improvements etc., should be included within the scope of the present invention.

Claims (10)

  1. A kind of 1. multi-functional quaternary cationics, it is characterised in that described multi-functional quaternary ammonium salt cationic table The structural formula of face activating agent is as follows：
  2. 2. a kind of preparation method of multi-functional quaternary cationics according to claim 1, its feature exist In comprising the steps successively：
    Step 1：The Cyanuric Chloride of 2 parts of moles is added to the 4,4'- diaminobenzil -2,2'- disulfonic acid of 1 part of mole In the aqueous solution, stirring, 2h is reacted；
    Step 2：The ertiary amine solution of dimethyl 14 of 2 parts of moles is added in the solution obtained by step 1, reacts 4h；
    Step 3：The 2- amion acetic acids of 2 parts of moles are added in the solution obtained by step 2, react 6h；
    Step 4：100mL sodium-chloride water solutions are added in the solution obtained by step 3, multi-functional quaternary ammonium salt cationic surface-active Agent is separated out and collected.
  3. 3. a kind of preparation method of multi-functional quaternary cationics according to claim 2, its feature exist In the reaction temperature of described step 1 is 0~5 DEG C, and pH is 3~4.
  4. 4. a kind of preparation method of multi-functional quaternary cationics according to claim 2, its feature exist In the reaction temperature of described step 2 is 30~40 DEG C, and pH is 7~8.
  5. 5. a kind of preparation method of multi-functional quaternary cationics according to claim 2, its feature exist In the reaction temperature of described step 3 is 90~100 DEG C, and pH is 9~10.
  6. 6. a kind of preparation method of multi-functional quaternary cationics according to claim 2, its feature exist In the reaction temperature of described step 4 is 25~30 DEG C.
  7. 7. a kind of preparation method of multi-functional quaternary cationics according to claim 2, its feature exist In the dosage of sodium-chloride water solution is 100mL in described step 4.
  8. 8. a kind of preparation method of multi-functional quaternary cationics according to claim 2, its feature exist In the solvent of the described ertiary amine solution of dimethyl 14 is acetone.
  9. 9. a kind of preparation method of multi-functional quaternary cationics according to claim 2, its feature exist In described pH value passes through Na2CO3Regulation.
  10. 10. according to any described multi-functional quaternary cationics of claim 1~9, it is characterised in that a kind of Application of the multi-functional quaternary cationics in terms of paper is brightened with surfactant.
CN201710461484.3A 2017-06-16 2017-06-16 A kind of multi-functional quaternary cationics and its preparation method and application Pending CN107337651A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107935954A (en) * 2017-11-28 2018-04-20 贺州学院 A kind of synthesis and application of new double long-chain alkyl quaternary surfactant

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102898855A (en) * 2012-09-29 2013-01-30 山东大学 Synthesis and application of cetyl or octadecyl dimethyl tertiary amine quaternary ammonium salt high performance fluorescent whitening agent having amino acid structure

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102898855A (en) * 2012-09-29 2013-01-30 山东大学 Synthesis and application of cetyl or octadecyl dimethyl tertiary amine quaternary ammonium salt high performance fluorescent whitening agent having amino acid structure

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107935954A (en) * 2017-11-28 2018-04-20 贺州学院 A kind of synthesis and application of new double long-chain alkyl quaternary surfactant

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Application publication date: 20171110