CN115386242B - Preparation and application of flexible chain-connected disazo orange high-water-washing disperse dye compound - Google Patents
Preparation and application of flexible chain-connected disazo orange high-water-washing disperse dye compound Download PDFInfo
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- CN115386242B CN115386242B CN202210909029.6A CN202210909029A CN115386242B CN 115386242 B CN115386242 B CN 115386242B CN 202210909029 A CN202210909029 A CN 202210909029A CN 115386242 B CN115386242 B CN 115386242B
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- 239000000986 disperse dye Substances 0.000 title claims abstract description 40
- 150000001875 compounds Chemical class 0.000 title claims abstract description 22
- 238000005406 washing Methods 0.000 title claims abstract description 21
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims abstract description 19
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 238000004043 dyeing Methods 0.000 claims abstract description 17
- 239000004744 fabric Substances 0.000 claims abstract description 9
- -1 succinic acid diester Chemical class 0.000 claims abstract description 9
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229920000728 polyester Polymers 0.000 claims abstract description 8
- 239000001384 succinic acid Substances 0.000 claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims description 26
- 238000005859 coupling reaction Methods 0.000 claims description 17
- 239000000243 solution Substances 0.000 claims description 15
- 230000008878 coupling Effects 0.000 claims description 14
- 238000010168 coupling process Methods 0.000 claims description 14
- 239000012954 diazonium Substances 0.000 claims description 14
- 150000001989 diazonium salts Chemical class 0.000 claims description 13
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 12
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 claims description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- 239000000706 filtrate Substances 0.000 claims description 9
- 238000001914 filtration Methods 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 238000001816 cooling Methods 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 8
- 239000002270 dispersing agent Substances 0.000 claims description 7
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 6
- HYVGFUIWHXLVNV-UHFFFAOYSA-N 2-(n-ethylanilino)ethanol Chemical compound OCCN(CC)C1=CC=CC=C1 HYVGFUIWHXLVNV-UHFFFAOYSA-N 0.000 claims description 6
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 6
- 239000000843 powder Substances 0.000 claims description 6
- 235000010288 sodium nitrite Nutrition 0.000 claims description 6
- 229940014800 succinic anhydride Drugs 0.000 claims description 6
- 238000004809 thin layer chromatography Methods 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 238000012544 monitoring process Methods 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 208000005156 Dehydration Diseases 0.000 claims description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 3
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical compound ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 239000012024 dehydrating agents Substances 0.000 claims description 3
- 230000018044 dehydration Effects 0.000 claims description 3
- 238000006297 dehydration reaction Methods 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- 239000012065 filter cake Substances 0.000 claims description 3
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 claims description 3
- 239000012074 organic phase Substances 0.000 claims description 3
- 239000002245 particle Substances 0.000 claims description 3
- 230000001376 precipitating effect Effects 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 238000009987 spinning Methods 0.000 claims description 3
- 238000000967 suction filtration Methods 0.000 claims description 3
- 238000011010 flushing procedure Methods 0.000 claims description 2
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical group [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 claims description 2
- 239000012752 auxiliary agent Substances 0.000 claims 2
- 230000002194 synthesizing effect Effects 0.000 claims 1
- 239000000975 dye Substances 0.000 abstract description 25
- 239000000835 fiber Substances 0.000 abstract description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- 238000012360 testing method Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- MMVDLMPGBRLTSO-UHFFFAOYSA-N 1-(diazonioamino)-4-nitrobenzene Chemical class [O-][N+](=O)C1=CC=C(N[N+]#N)C=C1 MMVDLMPGBRLTSO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000009981 jet dyeing Methods 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- APRRQJCCBSJQOQ-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 APRRQJCCBSJQOQ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000000418 atomic force spectrum Methods 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000004900 laundering Methods 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000005303 weighing Methods 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
- C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
- C09B33/02—Disazo dyes
- C09B33/06—Disazo dyes in which the coupling component is a diamine or polyamine
-
- 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/008—Preparations of disperse dyes or solvent dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Coloring (AREA)
Abstract
The invention relates to preparation and application of a disazo orange disperse dye compound containing succinic acid diester flexible chain connection, which has the following structure. The dye disclosed by the invention is used for dyeing polyester fibers, and the dyed fabric is full in hue; the dye has excellent various fastnesses, especially washing fastnesses, can reach 5 grades, has soft hand feeling after dyeing, and is a novel-structure high-washing fastnesses disperse dye. The dye structure of the invention is as follows:
Description
technical field:
the invention belongs to the technical fields of fine chemical engineering and textile printing and dyeing, and particularly relates to preparation and application of a disazo orange high-water-washing disperse dye compound connected by a flexible chain with a novel structure, which are suitable for dyeing polyester fibers.
The background technology is as follows:
disperse dyes are the most dominant dye species for dyeing polyester fibers. Azo disperse dye has the characteristics of high color development intensity, simple preparation process and the like, and plays an important role in dye production and printing and dyeing application. However, the traditional disperse dye has a series of problems of difficult dyeing, poor leveling property, poor dyeing fastness, especially poor washing fastness, hard hand feeling of dyed fabrics and the like due to small molecular structure and high dye crystallinity. The color fastness to washing is an important index for measuring the quality of the dye. With the improvement of the color fastness requirements of textiles and the continuous expansion of the application of dyed products, the market demands for high-washing fastness disperse dye varieties. Therefore, research on azo disperse dyes with high washing fastness and application thereof has important practical significance.
The invention comprises the following steps:
the invention aims to find a disazo orange high-water-washing disperse dye compound connected by flexible chains, and discloses a synthetic method and application thereof. The structural dye has excellent color fastness, especially excellent washing fastness, up to grade 5.
The preparation and application of the flexible chain-connected disazo orange high-water-washing disperse dye compound are characterized by comprising the following structures:
the invention also provides a preparation method of the flexible chain-connected disazo orange high-water-washing disperse dye compound, which is characterized by comprising the following steps of:
(1) Preparation of the coupling component: adding N-ethyl-N-hydroxyethyl aniline and succinic anhydride into a flask containing acetonitrile, heating to 85 ℃ for reflux reaction, monitoring the reaction process by adopting a Thin Layer Chromatography (TLC), stopping heating after the reaction is completed, cooling to room temperature, precipitating white powder, removing excessive succinic anhydride by suction filtration, spinning the filtrate to obtain a dark green oily matter, adding the dark green oily matter into the flask containing dicyclohexylcarbodiimide, adding dichloromethane, stirring uniformly, then adding N-ethyl-N-hydroxyethyl aniline and 4-dimethylaminopyridine, reacting at room temperature, monitoring the reaction process by TLC, filtering after the reaction is finished, removing insoluble matters, extracting the filtrate for multiple times by using carbon dichloride/water, collecting an organic phase, adding anhydrous sodium sulfate as a dehydrating agent for dehydration treatment, filtering to remove anhydrous sodium sulfate, and removing a solvent from the obtained solution by using a rotary evaporator to obtain a coupling component. The structure of the coupling component is as follows:
(2) Preparation of diazonium salt: adding a proper amount of water and hydrochloric acid into a beaker, stirring uniformly, heating to 70 ℃, adding paranitroaniline into the beaker, stirring until the paranitroaniline is completely dissolved, quickly adding a large amount of crushed ice, cooling the system to 0-5 ℃, quickly adding an aqueous solution of 30% sodium nitrite after a large amount of solid particles are separated out, and maintaining the temperature of the reaction system at 0-5 ℃, wherein the reaction solution gradually becomes a light green clear and transparent diazonium salt solution. And (3) eliminating excessive sodium nitrite by sulfamic acid after the reaction is finished to obtain diazonium salt solution of paranitroaniline, and preserving the diazonium salt solution at 0-5 ℃ for later use. The diazo component is as follows:
(3) Coupling reaction: dissolving coupling component in absolute ethyl alcohol, cooling to 0-5 ℃, slowly adding p-nitroaniline diazonium salt prepared in reaction (2) into the coupling component, maintaining the system to be weak acid, precipitating a large amount of powder after the reaction is finished, filtering, repeatedly flushing filter cakes with clear water until filtrate is colorless and transparent. And drying to obtain the disazo disperse dye compound connected with the succinic acid diester flexible chain.
The flexible chain-connected disazo orange high-water-washing disperse dye compound can be prepared into commercial disperse dye by adopting the existing dye commercial processing technology, adding a conventional dispersing auxiliary (sodium naphthalene sulfonate derivative, preferably one or a mixture of two of dispersing agents NNO, dispersing agents MF and modified dispersing agents MF) and preparing the synthesized compound into the commercial disperse dye.
The disperse dye is used for dyeing polyester fabrics and is orange red with full hue; has excellent various fastnesses, especially washing fastnesses, which can reach 5 grades.
Drawings
FIG. 1 is a visible absorption spectrum of the disperse dye compound of example 1.
FIG. 2 is an infrared spectrum of the disperse dye compound of example 1.
FIG. 3 is a disperse dye compound of example 1 1 H-NMR spectrum.
FIG. 4 is a dyeing process used in example 2.
FIG. 5 is a dye-uptake curve of the disperse dye of example 1.
FIG. 6 is a plot of the dye uptake of the disperse dye of example 1.
FIG. 7 is a graph of the lifting force of the disperse dye of example 1.
The specific embodiment is as follows:
the following are specific embodiments of the present invention, which are described in order to further illustrate the invention, not to limit the invention.
Example 1
5mmol the flexible chain-linked disazo disperse dye of the structure according to claim 1 is prepared in particular as follows:
(1) Preparation of the coupling component: 3.3g N-ethyl-N-hydroxyethyl aniline and 2.6g succinic anhydride are added into a three-neck flask containing 10mL acetonitrile, the temperature is raised to 85 ℃ for reflux reaction for 3 hours, the heating is stopped, the room temperature is reached, white powder is separated out, excessive succinic anhydride is removed by suction filtration, the filtrate is dried by spinning to obtain dark green oily matter, the oily matter is crystallized into solid after freezing, the yield is 95.7%, and the melting point is tested to be 86-88 ℃. 7.15g of the dark green product is weighed and added into a flask containing 8.35g of dicyclohexylcarbodiimide, 60mL of dichloromethane is added, after stirring uniformly, 4.45g N-ethyl-N-hydroxyethyl aniline and 0.325g of 4-dimethylaminopyridine are added, after reacting for 1h at room temperature, insoluble substances are removed by filtration, the filtrate is extracted for multiple times by carbon dichloride/water, an organic phase is collected, anhydrous sodium sulfate is added as a dehydrating agent for dehydration treatment, the anhydrous sodium sulfate is removed by filtration, and the solvent is removed by a rotary evaporator to obtain a coupling component with the yield of 85.7%.
(2) Preparation of diazonium salt: adding 4mL of water and 5mL of hydrochloric acid into a beaker, stirring uniformly, heating to 70 ℃, adding 1.38g of paranitroaniline into the beaker, stirring until the paranitroaniline is completely dissolved, quickly adding a large amount of crushed ice, cooling the system to 0-5 ℃, quickly adding 3.0g of 30% sodium nitrite aqueous solution after a large amount of solid particles are separated out, and maintaining the temperature of the reaction system at 0-5 ℃, wherein the reaction solution gradually becomes a light green clear and transparent diazonium salt solution. And (3) eliminating excessive sodium nitrite by sulfamic acid after the reaction is finished to obtain diazonium salt solution of paranitroaniline, and preserving the diazonium salt solution at 0-5 ℃ for later use.
(3) Coupling reaction: weighing 2.07g of the coupling component obtained in the step (1), dissolving in 20mL of absolute ethyl alcohol, cooling to 0-5 ℃, slowly adding the p-nitroaniline diazonium salt prepared in the reaction (2) into the coupling component, maintaining the system to be weak acid, and detecting the reaction end point by using a dilute H acid solution after reacting for 1H. A large amount of powder is separated out from the system, the filter cake is repeatedly washed by clear water until the filtrate is colorless and transparent. Drying to obtain the disazo disperse dye compound with succinic acid diester flexible chain connection, wherein the yield is 96.4%.
Dissolving the synthesized disperse dye compound in absolute ethyl alcohol to recrystallize the dye, filtering and stoving to obtain pure dye product. The dye purity was tested as follows to determine its structure:
the dye was added at 6.5X10 -5 M was dissolved in acetone, and its visible light absorption spectrum was measured by using a Japanese Hitachi U-3310 type ultraviolet-visible light spectrophotometer as shown in FIG. 1. The dye has a maximum absorption wavelength of 477nm and a molar extinction coefficient of 3.02X10 4 L·mol -1 ·cm -1 。
The infrared spectrum was measured using a FTS-25PC Fourier infrared spectrometer from Digital corporation, U.S. and the results are shown in FIG. 2. 3322cm -1 a=c-H stretching vibration peak for aromatic ring; 2928cm -1 、2850cm -1 is-CH 2 -an asymmetric stretching vibration peak; 1437cm -1 is-CH 3 Is a symmetrical bending vibration peak of (2); 1723cm -1 C=o stretching vibration peak for the ester group in dye D-6; 1508cm -1 、1325cm -1 The N=O asymmetric stretching vibration and the symmetric stretching vibration peak of the nitro group in the dye D-6 are respectively shown.
Dimethyl sulfoxide as solventThe hydrogen nuclear magnetic resonance spectrum was measured by using a Bruker company AV400 nuclear magnetic resonance spectrometer, and the results are shown in FIG. 3. 1 H NMR(400MHz，DMSO):δ8.38-8.33(2H,m,Ar-H), δ7.95-7.86(2H,m,Ar-H),δ7.83-7.81(2H,m,Ar-H),δ6.93-6.88(2H,m,Ar-H),δ4.25-4.21(2H,t,-CH 2 ),δ3.72-3.68(2H,t,-CH 2 ),δ3.57-3.52(2H,t,-CH 2 ), δ3.50-3.46(2H,t,-CH 2 ),δ1.15-1.12(3H,t,-CH 3 )。
The above tests all show the correctness of the structure of the synthesized dye.
Example 2
The flexible chain-linked disazo disperse dye compound obtained in example 1 was mixed with a diffusing agent NNO, and sand-dried to obtain an orange disperse dye.
On intermittent dyeing equipment, such as a high-temperature high-pressure jet dyeing machine, placing the desized polyester fabric into an acid dyeing bath (bath ratio of 1:15), directly adding 2% (o.w.f) of disperse dye, adding a proper amount of acetic acid to adjust the pH value of the dye liquor to be 4-5, and dyeing according to the process shown in figure 4 to obtain the bright orange-red polyester dyed fabric. The dye uptake and dye uptake curves of the test dyes are shown in figures 5 and 6 respectively.
Example 3
The flexible chain-linked disazo disperse dye compound obtained in example 1 was mixed with a modified dispersant MF, and sand-ground and dried to obtain an orange-red disperse dye.
On intermittent dyeing equipment, such as a high-temperature high-pressure jet dyeing machine, the desized polyester fabric is placed in an acid dyeing bath (bath ratio is 1:15), 0.5%, 1%, 2%, 3%, 5%, 8%, 10% and 12% (o.w.f) of disperse dye are respectively added, a proper amount of acetic acid is added to adjust the pH value of the dye liquor to be 4-5, the process of the embodiment 2 is used for dyeing, and the lifting force curve of the dye is tested, and the result is shown in figure 7.
Example 4
Rubbing fastness to washing and commercial laundering fastness according to GB/T3920-2008 textile colour fastness test, AATCC61/2003 test procedure 1A and 2A and 3A respectively: the accelerated reference specifies the crocking fastness and the washing fastness of test example 1. The results are shown in Table 1. From Table 1, it can be seen that the dyes according to the claims have a fastness to washing of all kinds of fabrics of grade 5.
TABLE 1 rubbing and washing fastness of dyed fabrics
Claims (3)
1. The disazo orange high-water-washing disperse dye compound containing the flexible chain connection of the succinic acid diester is characterized by having the following structure:
2. the method for synthesizing the disazo orange high water-washing disperse dye compound connected by the flexible chain containing the succinic acid diester according to claim 1, which is characterized by comprising the following steps:
(1) Preparation of the coupling component: adding N-ethyl-N-hydroxyethyl aniline and succinic anhydride into a flask containing acetonitrile, heating to 85 ℃ for reflux reaction, monitoring the reaction process by adopting a Thin Layer Chromatography (TLC), stopping heating after the reaction is completed, cooling to room temperature, precipitating white powder, removing excessive succinic anhydride by suction filtration, spinning the filtrate to obtain a dark green oily matter, adding the dark green oily matter into the flask containing dicyclohexylcarbodiimide, adding dichloromethane, stirring uniformly, then adding N-ethyl-N-hydroxyethyl aniline and 4-dimethylaminopyridine, reacting at room temperature, monitoring the reaction process by TLC, filtering after the reaction is finished, removing insoluble matters, extracting the filtrate for multiple times by using carbon dichloride/water, collecting an organic phase, adding anhydrous sodium sulfate as a dehydrating agent for dehydration treatment, filtering to remove anhydrous sodium sulfate, and removing a solvent from the obtained solution by using a rotary evaporator to obtain a coupling component; the structure of the coupling component is as follows:
(2) Preparation of diazonium salt: adding a proper amount of water and hydrochloric acid into a beaker, stirring uniformly, heating to 70 ℃, adding paranitroaniline into the beaker, stirring until the paranitroaniline is completely dissolved, rapidly adding a large amount of crushed ice, cooling the system to 0-5 ℃, rapidly adding an aqueous solution of 30% sodium nitrite after a large amount of solid particles are separated out, maintaining the temperature of the reaction system at 0-5 ℃, and gradually changing the reaction solution into a light green clear and transparent diazonium salt solution; after the reaction is finished, excessive sodium nitrite is eliminated by sulfamic acid, so that diazonium salt solution of paranitroaniline is obtained, and the diazonium salt solution is preserved for standby at the temperature of 0-5 ℃; the diazonium salt is as follows:
(3) Coupling reaction: dissolving coupling components in absolute ethyl alcohol, cooling to 0-5 ℃, slowly adding the paranitroaniline diazonium salt prepared in the reaction (2) into the coupling components, maintaining the system to be weak acid, separating out a large amount of powder after the reaction is finished, filtering, repeatedly flushing a filter cake with clear water until filtrate is colorless and transparent; and drying to obtain the disazo disperse dye compound connected with the succinic acid diester flexible chain.
3. Use of a disazo orange high water-washable disperse dye compound containing a succinic acid diester flexible chain linkage according to claim 1 or 2, characterized in that: comprises a disperse dye composition, a disazo high-washing-fastness disperse dye compound connected by a succinic acid diester flexible chain and an auxiliary agent; the auxiliary agent is sodium naphthalene sulfonate derivative, and is one or two of dispersing agent NNO, dispersing agent MF and modified dispersing agent MF; the disperse dye composition is used for dyeing polyester fabrics.
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|---|---|---|---|
| CN202210909029.6A CN115386242B (en) | 2022-07-29 | 2022-07-29 | Preparation and application of flexible chain-connected disazo orange high-water-washing disperse dye compound |
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| CN202210909029.6A CN115386242B (en) | 2022-07-29 | 2022-07-29 | Preparation and application of flexible chain-connected disazo orange high-water-washing disperse dye compound |
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| CN115386242A CN115386242A (en) | 2022-11-25 |
| CN115386242B true CN115386242B (en) | 2024-03-19 |
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Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1220462A (en) * | 1967-01-04 | 1971-01-27 | Ciba Ltd | Disazo dyestuffs and processes for their manufacture and use |
| CH540963A (en) * | 1967-08-25 | 1973-08-31 | Ciba Geigy Ag | Process for the production of disazo and polyazo dyes |
| GB1429177A (en) * | 1972-08-10 | 1976-03-24 | Ici Ltd | Azo dyes |
| US4607071A (en) * | 1978-05-26 | 1986-08-19 | Hoechst Aktiengesellschaft | Process for spin-dyeing of acid-modified polymers of copolymers of acrylonitrile using rapid-fixing di-quaternary cationic dyes |
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| CN111635643A (en) * | 2020-06-30 | 2020-09-08 | 绍兴文理学院 | Disperse dye compound and preparation and application methods thereof |
| CN111704807A (en) * | 2020-06-30 | 2020-09-25 | 绍兴文理学院 | Azo dye and preparation method and application thereof |
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| US6743567B2 (en) * | 2001-04-12 | 2004-06-01 | Lg Electronics Inc. | Polymer for data storage, data storage media coated by the same, data storage device and method using data storage media |
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