CN112940526A - Yellow-orange bisazo disperse dye and preparation method thereof - Google Patents
Yellow-orange bisazo disperse dye and preparation method thereof Download PDFInfo
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- CN112940526A CN112940526A CN202110166175.XA CN202110166175A CN112940526A CN 112940526 A CN112940526 A CN 112940526A CN 202110166175 A CN202110166175 A CN 202110166175A CN 112940526 A CN112940526 A CN 112940526A
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- 239000000986 disperse dye Substances 0.000 title claims abstract description 62
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims abstract description 56
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 239000000126 substance Substances 0.000 claims abstract description 39
- 238000005859 coupling reaction Methods 0.000 claims description 78
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 claims description 60
- 230000008878 coupling Effects 0.000 claims description 58
- 238000010168 coupling process Methods 0.000 claims description 58
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 claims description 20
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 claims description 17
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 claims description 17
- 229930003836 cresol Natural products 0.000 claims description 16
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 13
- -1 nitrophenyl monoazo compound Chemical class 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 150000003739 xylenols Chemical class 0.000 claims description 6
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 claims description 5
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 5
- 239000008103 glucose Substances 0.000 claims description 5
- XRUGBBIQLIVCSI-UHFFFAOYSA-N 2,3,4-trimethylphenol Chemical compound CC1=CC=C(O)C(C)=C1C XRUGBBIQLIVCSI-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000975 dye Substances 0.000 abstract description 38
- 238000004043 dyeing Methods 0.000 abstract description 27
- 239000000835 fiber Substances 0.000 abstract description 8
- 239000004744 fabric Substances 0.000 abstract description 7
- 238000007639 printing Methods 0.000 abstract description 5
- 230000007613 environmental effect Effects 0.000 abstract description 3
- 229920000728 polyester Polymers 0.000 abstract description 2
- 239000007788 liquid Substances 0.000 description 51
- 239000000243 solution Substances 0.000 description 48
- 238000006193 diazotization reaction Methods 0.000 description 40
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000000034 method Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- RTZYVAQWQXPIAC-UHFFFAOYSA-N 4-[(4-phenyldiazenylphenyl)diazenyl]phenol Chemical compound C1=CC(O)=CC=C1N=NC1=CC=C(N=NC=2C=CC=CC=2)C=C1 RTZYVAQWQXPIAC-UHFFFAOYSA-N 0.000 description 4
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 230000009286 beneficial effect Effects 0.000 description 4
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 229910052979 sodium sulfide Inorganic materials 0.000 description 4
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 4
- 230000002195 synergetic effect Effects 0.000 description 4
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 238000004134 energy conservation Methods 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 238000001308 synthesis method Methods 0.000 description 3
- 231100000331 toxic Toxicity 0.000 description 3
- 230000002588 toxic effect Effects 0.000 description 3
- 239000002351 wastewater Substances 0.000 description 3
- 238000004065 wastewater treatment Methods 0.000 description 3
- ZLCUIOWQYBYEBG-UHFFFAOYSA-N 1-Amino-2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=C(N)C(C)=CC=C3C(=O)C2=C1 ZLCUIOWQYBYEBG-UHFFFAOYSA-N 0.000 description 2
- VGKYEIFFSOPYEW-UHFFFAOYSA-N 2-methyl-4-[(4-phenyldiazenylphenyl)diazenyl]phenol Chemical compound Cc1cc(ccc1O)N=Nc1ccc(cc1)N=Nc1ccccc1 VGKYEIFFSOPYEW-UHFFFAOYSA-N 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- LMWMTSCFTPQVCJ-UHFFFAOYSA-N 2-methylphenol;phenol Chemical compound OC1=CC=CC=C1.CC1=CC=CC=C1O LMWMTSCFTPQVCJ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229940100630 metacresol Drugs 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000004537 pulping Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- QZQIWEZRSIPYCU-UHFFFAOYSA-N trithiole Chemical compound S1SC=CS1 QZQIWEZRSIPYCU-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001043 yellow dye Substances 0.000 description 1
Classifications
-
- 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
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/06—Disazo dyes from a coupling component "C" containing a directive hydroxyl group
- C09B31/062—Phenols
-
- 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
- D06P1/16—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 dispersed, e.g. acetate, dyestuffs
- D06P1/18—Azo dyes
-
- 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
- D06P3/34—Material containing ester groups
- D06P3/52—Polyesters
- D06P3/54—Polyesters using dispersed dyestuffs
Landscapes
- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
The invention relates to a disperse dye, in particular to a yellow to orange disazo disperse dye for dyeing and printing polyester fibers and blended fabrics thereof and a preparation method thereof. The invention provides the disazo disperse dye with stronger color development power and high dyeing degree, namely high build-up power and exhaustion degree, and the preparation method which meets the requirements of environmental protection. The chemical structural general formula of the disazo dye is as follows:
Description
Technical Field
The invention relates to a disperse dye, in particular to a yellow to orange disazo disperse dye for dyeing and printing polyester fibers and blended fabrics thereof and a preparation method thereof.
The yellow to orange disperse dyes mainly have azo and heterocyclic chemical structures, wherein the disazo accounts for a certain proportion. Such as C.I. disperse yellow 104, disperse orange 54, disperse orange 55, disperse yellow 23, etc., and domestic trade name disperse gold SE-3R (corresponding to the technology of CN1052496C, the name: azodiphenylamine yellow disperse dye, which is an ideal variety to replace C.I. disperse yellow 23), and the disazo disperse dye of Chinese patent publication No. CN103173032B, etc.
The preparation method of the disazo disperse dyes is generally to start from 4-nitroaniline and prepare the disazo disperse dyes by a three-step synthesis method. The first step is to obtain a 4-nitro monoazo compound by diazotizing 4-nitroaniline and then coupling with phenol or cresol; secondly, sodium sulfide is used as a reducing agent to reduce the sodium sulfide into a 4-amino monoazo compound; thirdly, coupling the 4-amino monoazo compound with corresponding coupling components after diazotization for the second time.
In order to completely reduce the 4-nitromonoazo compounds, a large excess of sodium sulfide must be used as reducing agent. After reduction, the amino monoazo compound can be separated out through acid neutralization, and in the neutralization process, hydrogen sulfide gas with stink toxicity and waste water with stink toxicity and containing hydrogen sulfide are generated, and the waste water is difficult to treat, seriously pollutes the environment and worsens the labor places.
Along with the progress of society, the production requirements of the disperse dyes, besides the requirements of green and environmental protection, also put forward higher requirements on the bright color and color fastness of the disperse dyes, and also require higher dyeing lifting power and exhaustion (dye uptake) at lower temperature for a shorter time, and dyeing residual liquid needs light color after dyeing, thereby being beneficial to the comprehensive requirements of energy conservation, emission reduction and wastewater treatment in the printing and dyeing industry.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide a disazo disperse dye with stronger color development power and high dyeing degree, namely high build-up power and exhaustion degree, and a preparation method for meeting the requirements of environmental protection.
The chemical structural general formula of the disazo dye is as follows:
wherein A is phenol
Or o-cresol
Or m-cresol
Or p-cresol
Or mixed tricresyl
Wherein X is methyl CH3Or hydrogen H
The disazo disperse dye does not contain and can not decompose 24 toxic arylamines, and the hue of the disazo disperse dye is between yellow and orange. All phenols in the disazo dye have the value of synthesizing the produced dye, so that the treatment method and yield are greatly different due to different varieties, and the cost is quite high and is not suitable for being used as a raw material of a common dye intermediate; particularly, the disperse golden yellow SE-3R which has the best performance on the current market is achieved and exceeded in the aspects of lifting power and exhaustion rate; has strong color development ability, and can produce high-concentration commercial dye; in addition, compared with the existing disperse dyes, the disperse dyes generally take 40 minutes for dyeing at 130 ℃, and the disperse dye product can achieve higher dye-uptake rate at lower temperature and shorter dyeing time (basically less than 30 minutes), is beneficial to energy conservation and wastewater treatment of printing and dyeing factories, and particularly can meet the development requirement of continuously and effectively reducing carbon emission.
In the invention, A in the chemical structural general formula is further preferably mixed xylenol (m-p-cresol) or mixed trimethylphenol.
Experiments combined with the examples prove that the combination of different phenols can generate synergistic effect, so that the dye performance, especially the lifting power and the exhaustion degree are more excellent; besides, for example, the CAS number of the three-mixed cresol is 1319-77, and the CAS number of the two-mixed cresol (m-p-phenol) is 4989-04-8, so that the three-mixed cresol is not only beneficial to reducing the cost due to lower price, but also very convenient to obtain. For this purpose, several groups of mixed phenols in different proportions are selected as corresponding examples for implementation.
Generally speaking, the components of the two-mixed cresol are 90-10% of para-cresol and 10-90% of meta-cresol; the components of the mixed cresol are para 15-5%, meta 20-5%, 4-ortho 65-90%.
The preparation method of the disazo disperse dye still adopts a three-step synthesis method, and firstly provides a new preparation method for reducing 4-nitrobenzene monoazo compounds into 4-aminobenzene monoazo compounds by using glucose instead of sodium sulfide as a new reducing agent.
The new preparation method does not generate hydrogen sulfide gas with foul smell and toxic hazard, and the wastewater does not contain hydrogen sulfide and sodium thiosulfate. Namely, the method has the greatest special point that the nitro-compound intermediate is reduced by glucose for the first time to prepare the dye intermediate for synthesizing the disperse dye, thereby greatly reducing the environmental pollution and improving the conditions of the working places.
In order to implement the novel preparation method, the disazo disperse dye provided by the invention is prepared from 4-nitroaniline, diazotized for the first time, and coupled with the first coupling component phenol or cresol in the chemical structural general formula for the first time to prepare the 4-nitro monoazo compound. The chemical structural formula is
Wherein X is methyl CH3Or hydrogen H
Reducing the prepared nitrophenyl monoazo compound by glucose to prepare a 4-aminophenyl monoazo compound, wherein the chemical structure general formula is as follows:
wherein X is methyl CH3Or hydrogen H
The corresponding coupling components in the third step of the synthesis method of the disazo disperse dye are phenol, cresol, mixed xylenol (m-p-cresol) or mixed tricresol respectively.
The 4-aminophenyl monoazo compound is prepared and then is diazotized for the second time and then is coupled with the second coupling component in the chemical structural general formula for the second time, so that the disazo disperse dye is prepared. The chemical structural general formula is shown as (1).
The present invention is illustrated by the following examples and experimental data and descriptions thereof, and it is apparent that these examples and experimental data and descriptions thereof are not intended to limit the scope of the present invention. With each different example allowing for differences in specific operating conditions. In the examples, where liquid is measured in milliliters (ml) and solids are measured in grams (g); the temperature was set at ℃.
Example 1
13.8g of 4-nitroaniline, 300ml of water and 36ml of 30% hydrochloric acid are mixed and stirred, the temperature is raised to 70-80 ℃, the mixture is dissolved, the mixture is cooled to below 50 ℃, crushed ice is added and cooled to 0-5 ℃, 24ml of 30% sodium nitrite is rapidly added under the liquid, the mixture reacts for 1 hour at the temperature of 0-10 ℃, and diazotization is finished. And preparing a first diazotization completion solution.
11g of 2-methylphenol, 300ml of water, 16ml of 30% sodium hydroxide and 100ml of 8% aqueous sodium carbonate solution were mixed, dissolved by stirring, and then crushed ice was added thereto to cool to 0 to 10 ℃ to obtain a first coupling component-completed solution.
Dropwise adding the diazotization completion solution for the first time into the coupling component completion solution under stirring, reacting for 2 hours at 5-10 ℃, completing the first coupling reaction, and filtering to obtain a 4-nitro monoazo compound filter cake. Adding water, stirring, pulping, adding 30% sodium hydroxide to adjust pH to 10, heating to 90 deg.C, adding 3% glucose aqueous solution 1500ml, and maintaining alkalinity with liquid alkali. And (3) maintaining the temperature for 2 hours after the addition, adding 30% hydrochloric acid to neutralize until the pH is 6-7, separating out precipitates, and filtering to obtain a 4-amino monoazo compound filter cake.
Adding 1000ml of 1% sodium hydroxide into the filter cake, stirring and dissolving, then adding 7g of sodium nitrite, stirring and dissolving, dropwise adding into a solution consisting of 55ml of 30% hydrochloric acid at 0-5 ℃ and 500ml of water, reacting for 2 hours at 0-5 ℃, completing diazotization, and preparing a second diazotization completion solution. Stirring and dissolving 10g of 3-methylphenol, 300ml of water, 24ml of 30% sodium hydroxide and 7-10g of sodium carbonate, adding ice, and cooling to 0-10 ℃ to obtain a second coupling component finished solution.
And dropwise adding the diazotization completion liquid for the second time into the coupling component completion liquid, reacting for 4 hours at 0-10 ℃, keeping the pH value about 7 for 2 hours, completing the coupling reaction for the second time, filtering and washing to obtain 28g of crude dye of the disazo disperse dye. The chemical structural formula is as follows:
example 2
A second diazotization complete solution was prepared as in example 1.
A second coupling component completion solution was prepared as in example 1 using 10.8g of 2-methylphenol in place of 3-methylphenol.
The diazotization completion liquid for the second time and the coupling component completion liquid for the second time are subjected to coupling reaction to prepare 29g of crude dye of the disazo disperse dye. The chemical structural formula is as follows:
example 3
A second diazotization complete solution was prepared as in example 1.
A second coupling component complete solution was prepared as in example 1, using 10.5g of 4-methylphenol instead of 10.5g of 3-methylphenol.
The diazotization completion liquid for the second time and the coupling component completion liquid for the second time are subjected to coupling reaction to prepare 28.6g of crude dye of the disazo disperse dye. The chemical structural formula is as follows:
example 4
A second diazotization complete solution was prepared as in example 1.
A second coupling component completed solution was prepared as in example 1 by using 10.5g of cresol-1 (m-p-cresol) as a substitute for 3-methylphenol. The mixed cresol No. 1 comprises 66 percent of m-cresol and 34 percent of p-cresol.
The diazotization completion liquid for the second time and the coupling component completion liquid for the second time are subjected to coupling reaction to prepare 29.3g of crude dye of the disazo disperse dye. The chemical structural formula is as follows:
example 5
A second diazotization complete solution was prepared as in example 1.
A second coupling component completed solution was prepared as in example 1 using trioxresol No. 1, 10.5g, in place of 3-methylphenol. The component of the mixed cresol No. 1 comprises 6 percent of para-position, 10 percent of meta-position and 84 percent of 4 ortho-position
And performing coupling reaction on the diazotization completion liquid for the second time and the coupling component completion liquid for the second time to obtain 27.8g of crude dye of the disazo disperse dye. The chemical structural formula is as follows:
example 6
A second diazotization complete solution was prepared as in example 1, using 11g of 3-methylphenol instead of 2-methylphenol.
A second coupling component-completed solution was prepared as in example 1 using 10.5g of 3-methylphenol.
The diazotization completion liquid for the second time and the coupling component completion liquid for the second time are subjected to coupling reaction to prepare 29.5g of crude dye of the disazo disperse dye. The chemical structural formula is as follows:
example 7
The second diazotization complete solution was prepared as in example 6.
A second coupling component completion solution was prepared as in example 1 using 10.5g of 4-methylphenol in place of 3-methylphenol.
The diazotization completion liquid for the second time and the coupling component completion liquid for the second time are subjected to coupling reaction to prepare 29g of crude dye of the disazo disperse dye. The chemical structural formula is as follows:
example 8
The second diazotization complete solution was prepared as in example 6.
A second coupling component completed solution was obtained as in example 1 except for using 10.5g of cresol-1 (m-p-cresol) as a substitute for 10.5g of 3-methylphenol.
The diazotization completion liquid for the second time and the coupling component completion liquid for the second time are subjected to coupling reaction to prepare 29g of crude dye of the disazo disperse dye. The chemical structural formula is as follows:
example 9
A second diazo component-completed solution was obtained by the method of example 6.
A second coupling component completed solution was obtained in the same manner as in example 1 except for using 10.5g of trioxresol No. 1 in place of 10.5g of 3-methylphenol.
The diazotization completion liquid for the second time and the coupling component completion liquid for the second time are subjected to coupling reaction to prepare about 28g of the disazo disperse dye raw dye. The chemical structural formula is as follows:
example 10
A second diazo component-completed solution was obtained by the method of example 1.
A second coupling component-completed solution was obtained in the same manner as in example 1 except for using 9.2g of phenol in place of 10.5g of 3-methylphenol.
The diazotization completion liquid for the second time and the coupling component completion liquid for the second time are subjected to coupling reaction to prepare 27.3g of crude dye of the disazo disperse dye. The chemical structural formula is as follows:
example 11
A first diazo component completion solution was prepared by the method of example 1 using 11g of 3-methylphenol in place of 2-methylphenol.
A second coupling component completed solution was obtained by using 9.2g of phenol in place of 10.5g of 3-methylphenol as in example 1.
And performing coupling reaction on the diazotization completion liquid for the second time and the coupling component completion liquid for the second time to obtain 27.5g of crude dye of the disazo disperse dye. The chemical structural formula is as follows:
example 12
A second diazotization complete solution was prepared as in example 1, using 9.4g of phenol instead of 2-methylphenol.
A second coupling component-completed solution was obtained in the same manner as in example 1 except for using 9.4g of phenol in place of 10.5g of 3-methylphenol.
And performing coupling reaction on the diazotization completion liquid for the second time and the coupling component completion liquid for the second time to obtain the disazo disperse dye raw dye. The chemical structural formula is as follows:
example 13
A second diazotization complete solution was prepared as in example 1, using 9.4g of phenol instead of 2-methylphenol.
A second coupling component-completed solution was obtained in the same manner as in example 1 except for using 10.5g of 4-methylphenol in place of 3-methylphenol.
And performing coupling reaction on the diazotization completion liquid for the second time and the coupling component completion liquid for the second time to obtain the disazo disperse dye raw dye. The chemical structural formula is as follows:
example 14
A second diazotization complete solution was prepared as in example 1, using 9.4g of phenol instead of 2-methylphenol.
A second coupling component completed solution was obtained as in example 1 except for using 10.5g of cresol-1 (m-p-cresol) as a substitute for 10.5g of 3-methylphenol. The cresol-mixed No. 1 component is para 34 percent and meta 66 percent.
And performing coupling reaction on the diazotization completion liquid for the second time and the coupling component completion liquid for the second time to obtain the disazo disperse dye raw dye. The chemical structural formula is as follows:
example 15
A second diazotization complete solution was prepared as in example 13, using 9.4g of phenol instead of 2-methylphenol.
A second coupling component completed solution was obtained in the same manner as in example 1 except for using 10.5g of trioxresol No. 1 in place of 10.5g of 3-methylphenol. And performing coupling reaction on the diazotization completion liquid for the second time and the coupling component completion liquid for the second time to obtain the disazo disperse dye raw dye. The chemical structural formula is as follows:
example 16
A second diazotization complete solution was prepared as in example 1.
A second coupling component completed solution was prepared as in example 1 by using 10.5g of cresol-2 (m-p-cresol) as a substitute for 3-methylphenol. The mixed cresol No. 2 comprises 80-90% of m-cresol and 20-10% of p-cresol.
And performing coupling reaction on the diazotization completion liquid for the second time and the coupling component completion liquid for the second time to obtain the disazo disperse dye raw dye. The chemical structural formula is similar to that of No. 7, but the mixture ratio of the components is different as follows:
example 17
Example 1 the procedure produces a second diazotization complete solution.
A second coupling component complete solution was prepared as in example 1, using trioxresol No. 2, 10.5g, in place of 3-methylphenol. The tertiary mixed cresol-2 component is para 10 percent, meta 15 percent and ortho 75 percent, and the secondary diazotization completion liquid and the secondary coupling component completion liquid are subjected to coupling reaction to prepare the bisazo disperse dye raw dye. The chemical structural formula is similar to that of (8), but the component proportions are different as follows:
example 18
A second diazotisation completion was prepared as in example 6.
A second coupling component completed solution was prepared as in example 1 using 10.5g of cresol-2 in place of 3-methylphenol. The second mixed cresol No. 2 consists of m-cresol 80-90 wt% and p-cresol 20-10 wt%, and the second diazotized liquid and the second coupling liquid are made to react to produce the diazo disperse dye. The chemical structural formula is similar to the structural formula (11) of the embodiment example 8, but the component proportions are different as follows.
Example 19
A second diazotisation completion was prepared as in example 6.
A second coupling component complete solution was prepared as in example 1, using trioxresol No. 2, 10.5g, in place of 3-methylphenol. The composition of the three-mixed cresol-2 is that para 10% meta 15% ortho 75%, the second diazo-combination completed liquid and the second coupling component completed liquid are coupled to obtain the disazo disperse dye raw dye. The chemical structural formula is similar to the structural formula (12) of the embodiment example 9, but the component proportions are different as follows.
Example 20
Example 1 the procedure produces a second diazotization complete solution.
A second coupling component completed solution was prepared as in example 1 using, in place of 3-methylphenol, cresol-3 No. 10.5 g. The second mixed cresol No. 3 consists of para 40% and meta 60%, and the second diazo combination liquid and the second coupling component liquid are coupled to produce the diazo disperse dye. The chemical structural formula is as follows:
example 21
Example 1 the procedure produces a second diazotization complete solution.
A second coupling component completed solution was prepared as in example 1 using trioxresol No. 3, 10.5g, in place of 3-methylphenol. The composition of the trismischmetal-No. 3 is that the secondary diazotization completion liquid with the para 15 percent meta 20 percent ortho 65 percent and the secondary coupling component completion liquid are subjected to coupling reaction to prepare the bisazo disperse dye raw dye. The chemical structural formula is similar to that of the No. (8) of the example 5, but the mixture ratio of the components is different:
example 22
A second diazotisation completion was prepared as in example 6.
A second coupling component completed solution was prepared as in example 1 using, in place of 3-methylphenol, cresol-3 No. 10.5 g. The second mixed cresol No. 3 consists of para 40% and meta 60%, and the second diazo combination liquid and the second coupling component liquid are coupled to produce the diazo disperse dye. The chemical structural formula is shown in the specification.
Example 23
A second diazotisation completion was prepared as in example 6.
A second coupling component completed solution was prepared as in example 1 using trioxresol No. 3, 10.5g, in place of 3-methylphenol. The composition of the trismischmetal-No. 3 is that the secondary diazotization completion liquid with the para 15 percent meta 20 percent ortho 65 percent and the secondary coupling component completion liquid are subjected to coupling reaction to prepare the bisazo disperse dye raw dye. The chemical structural formula is similar to that of (12) in example 9, but the mixture ratio of the components is different:
the disazo disperse dye raw dye prepared in the embodiment is added with corresponding water and a dispersing agent, ground until the diffusion performance reaches 4-5 grades, spray-dried and blended to obtain the commercial yellow to orange disperse dye.
The disazo disperse dyes prepared in the examples do not contain and decompose 24 toxic aromatic amines, and have hues between yellow and orange. The dyeing property is close to that of disperse golden yellow E-3RL (C.I. disperse yellow 23), the low-temperature disperse golden yellow dye belongs to low-temperature disperse dyes, the commercial dye can achieve high concentration, the strength can reach 3 times of that of the disperse golden yellow E-3RL, and energy and packaging materials are saved. Wherein c.i. disperse yellow 23 means: the trade name is: disperse golden yellow E-3R, disperse yellow E-RGFL, etc., the structural formula is:
the prepared disazo disperse dye is characterized by strong color development and lifting power, particularly, because of synergistic effect in dyeing, the disazo disperse dye is most suitable for dyeing dark fibers and fabrics, the utilization rate of the dye is improved, and the dyeing residual liquid is .
The lifting force is high or low, and the o.w.f 1% strength force is 100 as a reference; the increase of o.w.f. and the corresponding increase of the strength force, i.w.f. 2%, and the theoretical strength force of 200, are 100% dye uptake, which is practically impossible due to various factors. The larger the value, the higher the lift, which corresponds to a higher dye uptake and a darker dyed fabric color.
o.w.f is abbreviated as On weight of the fabric, and the percentage of the fabric dye based On the weight of the fabric (fiber) is used, for example, 100Kg of fiber, o.w.f. 8%, which requires 100X 0.08 to 8Kg of dye with standard strength (usually referred to as 100 min).
The data such as the lifting power of the disperse dye of the invention are measured according to GB/T2394-2013. The relative dyeing rate (namely the relative dyeing rate) is the percentage of the strength and the theoretically acquired strength of the fiber measured according to the lifting force, and is actually the ratio of the dyeing depth and the acquired depth of different dyes in unit weight of the fiber, and the data is considered to reflect the performance index of the fiber more intuitively and accurately. The dyes of the examples of this patent are now compared with the high lifting disperse golden yellow SE-3R, having the characteristics shown in the attached tables 1 and 2.
From the table 1 and the table 2, it can be shown that the chemical structural formula A of the product of the invention, namely the secondary coupling component, introduces mixed xylenol and mixed trithiol in a certain proportion, and also generates a significant synergistic effect, and enhances the lifting power and the relative color yield, which is shown in the attached table 3.
The disperse dye is generally used for dyeing at 130 ℃ for 40 minutes, and the disperse dye product can reach higher dye-uptake rate at lower temperature and shorter dyeing time, thereby being beneficial to energy conservation and wastewater treatment of printing and dyeing factories. The experimental data, in comparison with its disperse golden yellow SE-3R, are shown in the attached Table 4, which shows the dyeing temperatures and times required to achieve a dyeing yield of 95% or more.
TABLE 3 accompanying synergistic Effect
TABLE 4 dyeing temperature and time required to achieve a dyeing yield of 95% or more
| Products or examples | Dyeing temperature C | Dyeing time, minutes | Color rendering ratio% |
| Disperse golden SE-3R | 130 | 40 | ≥95％ |
| Example 1 | 125 | 25 | ≥95％ |
| Example 2 | 125 | 30 | ≥95％ |
| Example 20 | 125 | 30 | ≥95％ |
| Example 21 | 125 | 30 | ≥95％ |
Claims (3)
1. A yellow to orange disazo disperse dye is characterized in that the chemical structural general formula is as follows:
wherein A is: phenol and its preparation
Or o-cresol
Or m-cresol
Or p-cresol
Or mixed xylenol (m-p-cresol)
Or mixed tricresyl
Wherein X is: methyl CH3Or hydrogen H.
2. A yellow to orange disazo disperse dye according to claim 1, wherein a in the general chemical structure is: mixed xylenols (m-p-cresol) or mixed tricresyl.
3. A process for preparing the disazo disperse dye includes such steps as diazotizing 4-nitroaniline, coupling with phenol or cresol to obtain 4-nitro monoazo compound, and preparing the disazo disperse dye. The chemical structural formula is
Wherein X is methyl CH3Or hydrogen H
Reducing the prepared nitrophenyl monoazo compound by glucose to prepare a 4-aminophenyl monoazo compound, wherein the chemical structure general formula is as follows:
wherein X is methyl CH3Or hydrogen H
The corresponding coupling component in the third step is phenol, cresol, mixed xylenol (m-p-cresol) or mixed trimethylphenol.
The 4-aminophenyl monoazo compound is prepared and then is diazotized for the second time and then is coupled with the second coupling component in the chemical structural general formula for the second time, so that the disazo disperse dye is prepared. The chemical structural general formula is shown in claim 1.
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