CN117306277A - Arylamine modification and dyeing method applicable to cellulose fibers - Google Patents
Arylamine modification and dyeing method applicable to cellulose fibers Download PDFInfo
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- CN117306277A CN117306277A CN202311117513.6A CN202311117513A CN117306277A CN 117306277 A CN117306277 A CN 117306277A CN 202311117513 A CN202311117513 A CN 202311117513A CN 117306277 A CN117306277 A CN 117306277A
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- cellulose
- coupling component
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- dyeing
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- 238000004043 dyeing Methods 0.000 title claims abstract description 82
- 229920003043 Cellulose fiber Polymers 0.000 title claims abstract description 71
- 238000000034 method Methods 0.000 title claims abstract description 47
- 230000004048 modification Effects 0.000 title claims abstract description 34
- 238000012986 modification Methods 0.000 title claims abstract description 34
- 150000004982 aromatic amines Chemical class 0.000 title claims description 22
- 238000005859 coupling reaction Methods 0.000 claims abstract description 84
- 238000010168 coupling process Methods 0.000 claims abstract description 82
- 230000008878 coupling Effects 0.000 claims abstract description 79
- VYFOAVADNIHPTR-UHFFFAOYSA-N isatoic anhydride Chemical compound NC1=CC=CC=C1CO VYFOAVADNIHPTR-UHFFFAOYSA-N 0.000 claims abstract description 49
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 45
- 229910001868 water Inorganic materials 0.000 claims abstract description 45
- 239000000835 fiber Substances 0.000 claims abstract description 43
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 42
- 229920002678 cellulose Polymers 0.000 claims abstract description 38
- 239000001913 cellulose Substances 0.000 claims abstract description 38
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims abstract description 28
- 229920000742 Cotton Polymers 0.000 claims abstract description 23
- 235000017166 Bambusa arundinacea Nutrition 0.000 claims abstract description 16
- 235000017491 Bambusa tulda Nutrition 0.000 claims abstract description 16
- 235000015334 Phyllostachys viridis Nutrition 0.000 claims abstract description 16
- 239000011425 bamboo Substances 0.000 claims abstract description 16
- 229910000029 sodium carbonate Inorganic materials 0.000 claims abstract description 14
- 244000025254 Cannabis sativa Species 0.000 claims abstract description 9
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 claims abstract description 9
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 claims abstract description 9
- 235000009120 camo Nutrition 0.000 claims abstract description 9
- 235000005607 chanvre indien Nutrition 0.000 claims abstract description 9
- 239000011487 hemp Substances 0.000 claims abstract description 9
- 229920000297 Rayon Polymers 0.000 claims abstract description 6
- 239000002904 solvent Substances 0.000 claims abstract description 6
- 241000219146 Gossypium Species 0.000 claims abstract description 5
- 238000002156 mixing Methods 0.000 claims abstract description 5
- 239000000306 component Substances 0.000 claims abstract description 4
- 238000006011 modification reaction Methods 0.000 claims abstract description 3
- 238000010186 staining Methods 0.000 claims abstract description 3
- 244000082204 Phyllostachys viridis Species 0.000 claims abstract 2
- 238000005406 washing Methods 0.000 claims description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 27
- 239000000243 solution Substances 0.000 claims description 26
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 13
- KCEIVWKDBLAQKL-UHFFFAOYSA-N 2,5-dichloro-4-(3-methyl-5-oxo-4h-pyrazol-1-yl)benzenesulfonic acid Chemical group O=C1CC(C)=NN1C1=CC(Cl)=C(S(O)(=O)=O)C=C1Cl KCEIVWKDBLAQKL-UHFFFAOYSA-N 0.000 claims description 9
- 239000007864 aqueous solution Substances 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 6
- 238000004140 cleaning Methods 0.000 claims description 5
- 230000010355 oscillation Effects 0.000 claims description 5
- 230000035484 reaction time Effects 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 4
- PHIMTKWJUXQMMA-UHFFFAOYSA-L disodium;4-amino-5-hydroxynaphthalene-2,7-disulfonate Chemical group [Na+].[Na+].[O-]S(=O)(=O)C1=CC(O)=C2C(N)=CC(S([O-])(=O)=O)=CC2=C1 PHIMTKWJUXQMMA-UHFFFAOYSA-L 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- 229920002994 synthetic fiber Polymers 0.000 claims description 2
- APRRQJCCBSJQOQ-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid Chemical group OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 APRRQJCCBSJQOQ-UHFFFAOYSA-N 0.000 claims 1
- 239000004744 fabric Substances 0.000 abstract description 62
- 238000005265 energy consumption Methods 0.000 abstract description 6
- 238000005808 aromatic amination reaction Methods 0.000 abstract description 3
- 238000012545 processing Methods 0.000 abstract description 2
- 230000000052 comparative effect Effects 0.000 description 17
- 241001330002 Bambuseae Species 0.000 description 14
- 238000010586 diagram Methods 0.000 description 12
- 238000002474 experimental method Methods 0.000 description 12
- QPILZZVXGUNELN-UHFFFAOYSA-M sodium;4-amino-5-hydroxynaphthalene-2,7-disulfonate;hydron Chemical group [Na+].OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S([O-])(=O)=O)=CC2=C1 QPILZZVXGUNELN-UHFFFAOYSA-M 0.000 description 9
- 239000000985 reactive dye Substances 0.000 description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- 230000006872 improvement Effects 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- 238000001514 detection method Methods 0.000 description 4
- 239000012954 diazonium Substances 0.000 description 4
- 150000001989 diazonium salts Chemical class 0.000 description 4
- 235000010288 sodium nitrite Nutrition 0.000 description 4
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 3
- LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 3
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 3
- 238000006193 diazotization reaction Methods 0.000 description 3
- -1 fibrilia Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 238000002791 soaking Methods 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- CWJQQASJVVAXKL-UHFFFAOYSA-N 4-(3-Methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl)benzenesulfonic acid Chemical compound O=C1CC(C)=NN1C1=CC=C(S(O)(=O)=O)C=C1 CWJQQASJVVAXKL-UHFFFAOYSA-N 0.000 description 2
- HBZVNWNSRNTWPS-UHFFFAOYSA-N 6-amino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(O)C2=CC(N)=CC=C21 HBZVNWNSRNTWPS-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000004045 reactive dyeing Methods 0.000 description 2
- 239000010865 sewage Substances 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- 238000004065 wastewater treatment Methods 0.000 description 2
- TXJUTRJFNRYTHH-UHFFFAOYSA-N 1h-3,1-benzoxazine-2,4-dione Chemical compound C1=CC=C2C(=O)OC(=O)NC2=C1 TXJUTRJFNRYTHH-UHFFFAOYSA-N 0.000 description 1
- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000000188 beta-D-glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- JCHWMQZZTLGTJZ-UHFFFAOYSA-H hexasodium 5-[[4-chloro-6-[4-[[4-chloro-6-[[8-hydroxy-3,6-disulfonato-7-[(2-sulfonatophenyl)diazenyl]naphthalen-1-yl]amino]-1,3,5-triazin-2-yl]amino]anilino]-1,3,5-triazin-2-yl]amino]-4-hydroxy-3-[(2-sulfonatophenyl)diazenyl]naphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].Oc1c(N=Nc2ccccc2S([O-])(=O)=O)c(cc2cc(cc(Nc3nc(Cl)nc(Nc4ccc(Nc5nc(Cl)nc(Nc6cc(cc7cc(c(N=Nc8ccccc8S([O-])(=O)=O)c(O)c67)S([O-])(=O)=O)S([O-])(=O)=O)n5)cc4)n3)c12)S([O-])(=O)=O)S([O-])(=O)=O JCHWMQZZTLGTJZ-UHFFFAOYSA-H 0.000 description 1
- 239000000413 hydrolysate Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
Classifications
-
- 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
- D06P1/02—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 azo dyes
- D06P1/12—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 azo dyes prepared in situ
-
- 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
- D06P1/64—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 without sulfate or sulfonate groups
- D06P1/642—Compounds containing nitrogen
- D06P1/6426—Heterocyclic compounds
-
- 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
- D06P1/673—Inorganic compounds
- D06P1/67333—Salts or hydroxides
- D06P1/6735—Salts or hydroxides of alkaline or alkaline-earth metals with anions different from those provided for in D06P1/67341
-
- 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
- D06P3/68—Preparing azo dyes on the material
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
- Y02P70/50—Manufacturing or production processes characterised by the final manufactured product
- Y02P70/62—Manufacturing or production processes characterised by the final manufactured product related technologies for production or treatment of textile or flexible materials or products thereof, including footwear
Abstract
The invention belongs to the dyeing and finishing field, and in particular relates to an aromatic amination modification and a dyeing method suitable for cellulose fibers, which comprises the following steps: 1) Isatoic anhydride modified cellulose fibers: in a solvent, carrying out modification reaction on cellulose fibers and isatoic anhydride, and then carrying out aftertreatment to obtain isatoic anhydride modified cellulose; 2) Diazotisation of isatoic anhydride modified cellulose: diazotizing isatoic anhydride modified cellulose obtained in the step 1) to obtain diazotized cellulose; 3) Coupling staining of diazotized cellulose: mixing a coupling component, sodium hydroxide, sodium carbonate and water to form a coupling component solution, and reacting the diazotized cellulose fiber obtained in the step 2) with the coupling component solution to form the coupling dyed fiber. The dyeing method of the invention is used for dyeing cellulose fiber fabrics such as cotton, hemp, bamboo, viscose and the like, and has low dyeing energy consumption, short time, bright color of the dyed fabrics, higher wet processing fastness and strong practicability.
Description
Technical Field
The invention belongs to the dyeing and finishing field, and particularly relates to an aromatic amination modification suitable for cellulose fibers and a dyeing method thereof.
Background
In the textile industry, cellulose fiber is one of important raw materials, and cotton fiber, fibrilia, bamboo fiber and viscose fiber can be subjected to substitution reaction with reactive dye to realize reactive dyeing of fabrics due to the fact that the molecular structure of the cellulose fiber contains a large number of hydroxyl groups. Meanwhile, in recent years, digital ink-jet printing technology is rapidly developed, and the advantages of simple process, high printing precision, low energy consumption, small occupied area and the like are utilized to meet the market demands.
The reactive dye is widely used for dyeing cellulose fiber due to the advantages of complete chromatography, high wet fastness, convenient use and the like. However, the dyeing is carried out at high temperature and with high energy consumption, and in order to obtain high dye exhaustion rate, a large amount of electrolyte (such as sodium chloride) is required for dyeing promotion, so that a large amount of salt-containing colored sewage is generated. In addition, when dyeing cellulosic fiber fabrics, it is often necessary to add alkaline materials (e.g., sodium carbonate) to fix the color to promote covalent bonding of the dye to the fiber and to improve color fastness. However, the reactive groups of the reactive dye also have the problems of easy hydrolysis, poor storage stability and the like, the fixation rate is only 50% -80%, and a large amount of hydrolytic dye enters the dyeing wastewater, so that the difficulty of wastewater treatment is increased, and the environmental protection is not facilitated.
Disclosure of Invention
The technical problem to be solved by the invention is to provide an aromatic amination modification and a dyeing method thereof which are suitable for cellulose fibers, namely, a diazotization-coupling dyeing method of isatoic anhydride modified cellulose fibers.
In order to solve the technical problems, the invention provides an arylamine modification and a dyeing method applicable to cellulose fibers, which comprises the following steps:
1) Isatoic anhydride modified cellulose fibers:
in a solvent, carrying out modification reaction on cellulose fibers and isatoic anhydride, wherein the dosage of the isatoic anhydride is 1-10% of the mass of the cellulose fibers; the reaction temperature is 100+/-10 ℃, and the reaction time is 6+/-0.5 h;
then post-treatment is carried out to obtain isatoic anhydride modified cellulose;
2) Diazotisation of isatoic anhydride modified cellulose:
diazotizing isatoic anhydride modified cellulose obtained in the step 1) to obtain diazotized cellulose;
3) Coupling staining of diazotized cellulose:
mixing a coupling component, sodium hydroxide, sodium carbonate and water to form a coupling component solution, wherein the concentration of the coupling component in the coupling component solution is 2+/-0.2 g/L, the concentration of sodium hydroxide is 0.1-2 g/L, and the concentration of sodium carbonate is 0.5-5 g/L;
reacting the diazotized cellulose fiber obtained in the step 2) with a coupling component solution to generate a coupling dyed fiber; the coupling dyeing bath ratio is 1:20 to 100, i.e. cellulose fibers of step 1): coupling component solution = 1g: 20-100 mL.
Illustratively, in the present invention:
modifying and modifying cellulose fiber by using isatoic anhydride, and reacting hydroxyl groups on the cellulose fiber with the isatoic anhydride, so that an aromatic primary amine structure is introduced into the cellulose fiber to obtain isatoic anhydride modified cellulose; subsequently, the isatoic anhydride modified cellulose is diazotized and then directly reacts with a coupling component to generate a colored substance containing an azo structure, so that reactive dyeing of the cellulose fiber is realized.
As an improvement of the arylamine modification and the dyeing method thereof applicable to the cellulose fiber of the invention:
the coupling component is a yellow coupling component, a red coupling component and a blue coupling component;
the yellow coupling component is 1- (2, 5-dichloro-4-sulfophenyl) -3-methyl-5-pyrazolone, and the structural formula is as follows:
the red coupling component is H acid, and the structural formula is as follows:
the blue coupling component is an H acid disodium salt derivative, and the structural formula is as follows:
description:
among the coupling components described above:
the yellow coupling component 1- (2, 5-dichloro-4-sulfophenyl) -3-methyl-5-pyrazolone, the red coupling component (H acid) can be obtained in conventional commercially available form;
the preparation method of the blue coupling component (disodium salt derivative of H acid) comprises the following steps:
(1) Diazotisation reaction
M-nitroaniline (1.38 g,0.01 mol) was dissolved in hydrochloric acid (10 mL,0.015 mol); the mixture was cooled in an ice water bath, then NaNO was added 2 Rapidly adding an aqueous solution (0.012mol, 2 mL) into the mixture, stirring the mixture for 30 minutes, and obtaining a diazonium salt solution after the reaction is finished when the reaction solution does not react with the Erich reagent;
(2) Coupling reaction
Adding 0.015mol of H acid monosodium salt and 1g of NaOH into 100mL of water, filtering to remove insoluble solid substances, and then adding alkali to adjust the pH of the solution to 9-10 to obtain a coupling component;
slowly adding the diazonium salt solution obtained in the step (1) into the coupling component; adding 1% NaOH aqueous solution to make the mixture react for 2 hours under the condition of pH 9-10; after completion of the waiting reaction, HCl was added to adjust the pH to 1-2 to acidify the coupling product to form a precipitate, the precipitate was filtered, and the product was washed 3 times, and then dried under vacuum to constant weight to obtain a blue coupling component.
As a further improvement of the arylamine modification and dyeing method for cellulose fibers according to the present invention: the solvent in the step 1) is N, N-Dimethylformamide (DMF).
As a further improvement of the arylamine modification and dyeing method for cellulose fibers according to the present invention: the post-treatment in the step 1) is as follows:
washing in hot water at 60+/-10 ℃ for about 0.5h, so as to remove isatoic anhydride and hydrolysate attached to the surface of the cellulose fiber, and washing with cold water at 5-10 ℃; obtaining isatoic anhydride modified cellulose.
As a further improvement of the arylamine modification and the dyeing method thereof applicable to cellulose fibers of the present invention, the step 2):
adding isatoic anhydride modified cellulose obtained in the step 1) into hydrochloric acid aqueous solution, and then adding (dropwise adding for about 5+/-1 min) NaNO 2 Stirring the aqueous solution at room temperature for reaction for 10-30 min; the HCl and NaNO 2 The molar ratio of (2) is 1: (1.01.+ -. 0.01) mol of HCl is added per 1g of cellulose fiber (0.001.+ -. 0.0001);
taking out the reacted cellulose, washing with water (until no solid particles exist on the surface of the fiber), and drying to obtain the diazotized cellulose for later use.
As a further improvement of the arylamine modification and the dyeing method thereof applicable to cellulose fibers of the present invention, the step 3):
under continuous oscillation, the diazotized cellulose obtained in the step 2) is put into a coupling component solution to be soaked for 10-20 min at room temperature, so that dyeing is realized, and coupling dyed fibers are generated;
and then, washing the coupled dyed fiber with water (removing various substances adsorbed on the cellulose fiber freely), and airing to obtain the dyed cellulose fiber.
As a further improvement of the arylamine modification and the dyeing method thereof applicable to the cellulose fiber of the present invention, the cellulose fiber is any one of the following:
natural fibers, man-made fibers, blends of natural and man-made fibers.
The natural fiber is any one of the following: cotton, hemp and bamboo fiber;
the artificial fiber is viscose fiber.
As a further improvement of the arylamine modification and the dyeing method thereof which are applicable to the cellulose fiber, the water washing in the step 3) is alternately performed with hot water washing at 60+/-10 ℃ and cold water washing at 5-10 ℃.
In the present invention:
step 1): 500+ -100 ml of solvent is added to each 10g of cellulose fiber,
mixing concentrated hydrochloric acid containing 0.01mol of HCl with 15+/-2 g water to obtain hydrochloric acid solution;
NaNO 2 the amount of water in the aqueous solution is such that the NaNO 2 Dissolving.
The cellulose macromolecules are formed by bonding beta-D-glucose residues with each other through 1, 4-glycoside bonds, a large number of hydroxyl groups are contained on two tail end glucose residues of the cellulose macromolecules, isatoic anhydride is utilized to modify cellulose fibers, a sufficient amount of aromatic primary amino groups can be introduced into the cellulose fibers, the isatoic anhydride modified cellulose can be prepared into diazotized cellulose through diazotization reaction, and then the diazotized cellulose and a coupling component are subjected to dyeing reaction, so that diazotization-coupling dyeing of the isatoic anhydride modified cellulose fibers is realized.
The diazotization-coupling dyeing mechanism of isatoic anhydride modified cellulose fibers is as follows:
in the present invention, the fabrics woven from the natural fiber cotton, hemp, bamboo fiber and man-made fiber viscose fiber, the blended fabrics made from these fibers, and the blended fabrics made from these fibers and chemical fiber or other kinds of natural fibers are all commonly known fabrics, and are all commercially available.
In the present invention, isatoic anhydride (CAS: 118-48-9) is used, and is commercially available.
In the invention, all the materials such as hydrochloric acid, sodium nitrite, urea, sodium hydroxide, sodium carbonate and the like are commonly known chemical products and are commercially available.
The cellulose fiber obtained by the dyeing method provided by the invention is tested for dry and wet rubbing fastness, washing fastness and sublimation fastness by adopting the national standard common in the field.
In the present invention:
the isatoic anhydride is used for modifying cellulose fibers, and dyeing can be rapidly finished under the room temperature condition through further diazotization coupling reaction; the reactive dye in the prior art needs longer reaction time for dyeing;
diazotization is carried out on isatoic anhydride modified cellulose modified by isatoic anhydride modification, and diazonium salt formed by the obtained diazotized cellulose is stable and can be stored at room temperature; in the prior art, diazonium salt needs to be stored at 0-5 ℃ and cannot be stored for a long time, and must be prepared for use at present;
the coupling dyeing can be covalently combined with cellulose fiber under the alkaline condition at room temperature; the covalent bonding in the prior art needs to be carried out at 0-5 ℃ and under alkaline conditions.
The invention has the beneficial effects that:
the invention successfully diazotizes cellulose fiber, then carries out coupling dyeing with a coupling component, combines the synthesis process of azo dye with the dyeing process of cellulose fiber in practice, realizes the dyeing in the process of near room temperature, greatly reduces the dyeing energy consumption, simultaneously avoids the discharge of colored wastewater in the dyeing process, realizes an environment-friendly green dyeing method, simultaneously improves the rubbing fastness, washing fastness, sublimation fastness and the like of the dyed cellulose fiber, improves the application performance of the product, and provides a brand-new dyeing method for the cellulose fiber.
The dyeing method provided by the invention is used for dyeing cotton, hemp, bamboo, viscose and other cellulose fiber fabrics, and has the advantages of low dyeing energy consumption, short time, bright color of the dyed fabrics, high wet processing fastness and strong practicability.
Drawings
The following describes the embodiments of the present invention in further detail with reference to the accompanying drawings.
FIG. 1 is a graph showing the K/S profile of the yellow cellulosic fabric (1- (2, 5-dichloro-4-sulfophenyl) -3-methyl-5-pyrazolone) obtained in example 1;
FIG. 2 is a graph of the red cellulose fabric (H acid) and K/S curve obtained in example 2;
FIG. 3 is a graph of the K/S curve of the blue cellulose fabric (disodium H acid derivative) obtained in example 3;
FIG. 4 is a K/S plot of a reactive dye dyed cellulosic fabric of comparative example 1;
FIG. 5 is a graph of the K/S curve of a yellow cellulosic fabric of comparative example 2 (1- (2, 5-dichloro-4-sulfophenyl) -3-methyl-5-pyrazolone);
FIG. 6 is a graph of the K/S curve of the yellow cellulosic fabric of comparative example 3-1 (1- (4-sulfophenyl) -3-methyl-5-pyrazolone);
FIG. 7 is a graph of the K/S curve of the red cellulose fabric (gamma acid) of comparative example 3-2;
FIG. 8 is a graph of the K/S curve of the blue cellulose fabric (H acid derivative 1) of comparative examples 3-3.
Detailed Description
The invention will be further described with reference to the following specific examples, but the scope of the invention is not limited thereto:
room temperature according to the invention means 20-30 ℃ (preferably 25 ℃). The concentration of the concentrated hydrochloric acid is 36-38%.
Example 1, an arylamine modification and dyeing method for cellulose fibers:
the cellulose fiber is cotton fabric 10g, dyeing bath ratio 1:20, sequentially performing the following steps:
1) Cellulose fiber modification (modification of cotton fabric with isatoic anhydride):
10g of cotton fabric was immersed in 500mL of an N, N-Dimethylformamide (DMF) solution containing 0.3g (0.0018 mol) of isatoic anhydride and reacted at 100℃for 6 hours, thereby completing the modification. Then cleaning for 0.5h in hot water with the temperature of 60+/-10 ℃ and then washing with cold water with the temperature of 5-10 ℃; obtaining the isatoic anhydride modified cotton fabric.
Description: the purpose of the hot and cold water washing is to remove unreacted isatoic anhydride and its hydrolysis products from the cellulosic fibers.
2) Diazotizing isatoic anhydride modified cotton fabric:
mixing concentrated hydrochloric acid containing 0.01mol of HCl with 15g of water to obtain a hydrochloric acid solution;
preparing an aqueous solution of sodium nitrite by 0.0101mol of sodium nitrite and 1g of water;
dissolving the isatoic anhydride modified cotton fabric obtained in the step 1) in the hydrochloric acid solution, slowly dropwise adding (about 5 min) an aqueous solution of sodium nitrite, stirring at room temperature for reaction for 10min, and removing excessive nitrous acid by using urea; and then taking out, washing with water (when the surface of the cotton fabric is free of solid particles, cleaning is finished), and then drying (until the cotton fabric is basically free of water, namely the water content is less than or equal to 2%) to obtain the diazotized cotton fabric.
Excess nitrous acid is removed with urea, a conventional technique, namely: slowly adding urea, dipping a small amount of spots, and judging that the excessive nitrous acid is removed after the spots are not discolored in 1-2s on potassium iodide test paper.
3) Coupling dyeing:
1- (2, 5-dichloro-4-sulfophenyl) -3-methyl-5-pyrazolone is selected as a yellow coupling component, and has a structural formula as follows:
1- (2, 5-dichloro-4-sulfophenyl) -3-methyl-5-pyrazolone, sodium hydroxide, sodium carbonate and water are mixed to form a coupling component solution, wherein the concentration of 1- (2, 5-dichloro-4-sulfophenyl) -3-methyl-5-pyrazolone is 2g/L, the concentration of sodium hydroxide is 0.2g/L, and the concentration of sodium carbonate is 5g/L.
And (3) under continuous oscillation, putting the diazotized cotton fabric obtained in the step (2) into 200mL of coupling component solution, soaking at room temperature for reaction for 10min to realize dyeing, then alternately performing hot water washing at 60+/-10 ℃ and cold water washing at 5-10 ℃, and finally airing (to constant weight) to obtain the dyed cotton fabric A1.
Description: the above-mentioned alternate hot water washing and cold water washing is to remove various impurities which are advantageously adsorbed on the fabric until the eluent is colorless, and the water washing is ended.
Experiment 1 the cotton fabric A1 used in example 1 was tested according to the wash fastness GB/T3921-2008, the rub fastness experiment GB/T3920-2008 and the dry heat fastness experiment GB/T5718-1997:
the K/S curve and the pattern diagram are shown in figure 1, the wavelength corresponding to the maximum K/S value point of the pattern in the curve diagram is 390nm, and the maximum K/S value of dyeing is 6.72. The dry friction fastness of the dyed fabric is 4-5 grades, the wet friction fastness is 4-5 grades, the soaping fastness is 4-5 grades, the dry heat fastness is 4-5 grades, the relative fixation rate reaches 95.6%, and the dyed fabric has excellent color fastness by adopting the method. The color of the obtained dyed cotton fabric was tender yellow.
Example 2, an arylamine modification and dyeing method for cellulose fibers:
the cellulose fiber was 10g of hemp, and the dyeing bath ratio was 1:40, sequentially performing the following steps:
1) Cellulose fiber modification:
10g of the hemp fabric was immersed in 500mL of an N, N-Dimethylformamide (DMF) solution containing 0.6g of isatoic anhydride and reacted at 100℃for 6 hours, thereby completing the modification. Then cleaning for 0.5h in hot water with the temperature of 60+/-10 ℃ and then washing with cold water with the temperature of 5-10 ℃; obtaining the isatoic anhydride modified linen fabric.
2) Diazotizing isatoic anhydride modified hemp fabric:
diazotizing the isatoic anhydride modified linen fabric obtained in the step 1) with reference to the step 2) of the example 1 to obtain a diazotized linen fabric.
3) Coupling dyeing:
h acid is selected as a red coupling component, and the structural formula is as follows:
h acid, sodium hydroxide, sodium carbonate and water were mixed to form a coupling component solution in which the concentration of H acid was 2g/L, the concentration of sodium hydroxide was 0.2g/L and the concentration of sodium carbonate was 5g/L.
And (3) under continuous oscillation, putting the diazotized linen fabric obtained in the step (2) into 400mL of coupling component solution, soaking at room temperature for reaction for 10min to realize dyeing, then alternately washing with hot water at 60+/-10 ℃ and cold water at 5-10 ℃, and finally airing to obtain the dyed linen fabric B1.
Experiment 2 the original scrim B1 used in example 2 was tested as described in experiment 1:
the K/S curve and the cloth sample graph are shown in FIG. 2, the wavelength corresponding to the maximum K/S value point of the cloth sample in the curve graph is 540nm, and the maximum K/S value of dyeing is 6.78. The dry rubbing fastness of the dyed fabric is 4-5 grades, the wet rubbing fastness is 4-5 grades, the soaping fastness is 4-5 grades, the dry heat fastness is 4-5 grades, the relative fixation rate reaches 92.2%, and the dyed fabric has excellent color fastness by adopting the method. The resulting dyed hemp fabric had a rose-red color.
Example 3, an arylamine modification and dyeing method for cellulose fibers:
the cellulose fiber is 10g of bamboo fiber, and the dyeing bath ratio is 1:50, the following steps are sequentially carried out:
1) Cellulose fiber modification:
10g of bamboo fiber is immersed in 500mL of N, N-Dimethylformamide (DMF) solution containing 0.9g of isatoic anhydride and reacted at 100 ℃ for 6h, thereby completing the modification. Then cleaning for 0.5h in hot water with the temperature of 60+/-10 ℃ and then washing with cold water with the temperature of 5-10 ℃; obtaining the isatoic anhydride modified bamboo fiber.
2) Diazotizing isatoic anhydride modified bamboo fibers:
diazotizing the isatoic anhydride modified bamboo fiber obtained in the step 1) with reference to the step 2) of the embodiment 1 to obtain the diazotized bamboo fiber.
3) Coupling dyeing:
the disodium salt derivative of H acid is selected as a blue coupling component, and the structural formula is as follows:
the blue coupling component, sodium hydroxide, sodium carbonate and water were mixed to form a coupling component solution in which the concentration of the blue coupling component was 2g/L, the concentration of sodium hydroxide was 0.2g/L and the concentration of sodium carbonate was 5g/L.
And (3) under continuous oscillation, putting the diazotized bamboo fiber obtained in the step (2) into 500mL of coupling component solution, soaking for 10min at room temperature to realize dyeing, then alternately performing hot water washing at 60+/-10 ℃ and cold water washing at 5-10 ℃, and finally airing to obtain the dyed bamboo fiber C1.
Experiment 3 the raw bamboo fibre C1 used in example 3 was tested as described in experiment 1:
the K/S curve and the pattern diagram are shown in figure 3, the wavelength corresponding to the maximum K/S value point of the pattern in the curve diagram is 600nm, and the maximum K/S value of dyeing is 6.21. The dry friction fastness of the dyed fabric is 4-5 grades, the wet friction fastness is 4-5 grades, the soaping fastness is 4-5 grades, the dry heat fastness is 4-5 grades, the relative fixation rate reaches 96.1%, and the dyed fabric has excellent color fastness by adopting the method. The color of the obtained dyed bamboo fiber is dark blue.
Comparative example 1:
cotton fabric (same as the original cotton fabric used in example 1) was dyed by a conventional dyeing method using a reactive dye, which was selected as reactive red KE-3B having the following structural formula:
dyeing is carried out according to the following process, wherein the mass concentration of dye is 0.2g/L, the mass concentration of sodium chloride is 70g/L, the mass concentration of sodium carbonate is 10g/L, and the bath ratio is 1:100, dyeing at room temperature, heating to 70 ℃ at a heating rate of 1 ℃/min, preserving heat for 60min, taking out the cotton fabric, washing with water for multiple times, soaping, and airing.
The K/S curve of the cotton fabric treated by the method described in comparative example 1 is shown in FIG. 4, the wavelength corresponding to the maximum K/S value point of the cloth sample in the curve graph is 540nm, and the maximum K/S value of dyeing is 8.04. The method is used for detecting according to the method described in the experiment 1, the dry friction fastness of the dyed fabric is 4-5 grades, the wet friction fastness is 4 grades, the soaping fastness is 4-5 grades, the dry heat fastness is 4 grades, and the relative fixation rate reaches 61.8%.
Description: if the dyeing temperature is changed to 70 ℃ to room temperature, the dyeing depth K/S is only 1.42, and the dyeing rate is only 28.92%.
The dye solution in comparative example 1 contains not only dye but also a large amount of electrolyte (NaCl and Na 2 CO 3 ) The colored salty sewage is discharged, and the difficulty of wastewater treatment is increased.
Therefore, the temperature required by dyeing with the conventional reactive dye is far higher than that of the dyeing method, the energy consumption is high, and various indexes of the dyed fabric are better than those of the dyed fabric with the conventional reactive dye.
Comparative example 2, the reaction temperature in step 1) of example 1 was changed from "100 ℃ to" 70 ℃ and the reaction time was changed from "6h" to "9h", the remainder being identical to example 1.
The detection was performed as described in experiment 1 above, and the results obtained were: the K/S curve and the pattern diagram are shown in FIG. 5, the wavelength corresponding to the maximum K/S value point of the pattern in the curve diagram is 390nm, and the maximum K/S value of dyeing is 5.51. The dry rubbing fastness of the dyed fabric is 4-5 grades, the wet rubbing fastness is 4 grades, the soaping fastness is 4-5 grades, the dry heat fastness is 4 grades, and the relative fixation rate reaches 85.4 percent.
From this, it can be seen that the cloth sample treated by the method of comparative example 2, although having a reduced temperature, has a prolonged reaction time, and the various indexes of the dyed fabric of the present invention are superior to those of the method of comparative example 2.
Comparative example 3-1 the yellow coupling component of example 1 was changed from 1- (2, 5-dichloro-4-sulfophenyl) -3-methyl-5-pyrazolone: 1- (4-sulfophenyl) -3-methyl-5-pyrazolone having a structural formula as follows; the remainder was identical to example 1.
The detection was performed as described in experiment 1 above, and the results obtained were: the K/S curve and the pattern diagram are shown in FIG. 6, the wavelength corresponding to the maximum K/S value point of the pattern in the curve diagram is 400nm, and the maximum K/S value of dyeing is 5.77. The dry friction fastness of the dyed fabric is 4-5 grades, the wet friction fastness is 4 grades, the soaping fastness is 4 grades, the dry heat fastness is 4 grades, the relative fixation rate reaches 87.6 percent,
as can be seen, the yellow coupling component used in example 1 was superior in K/S, soaping fastness, fixation ratio, etc. to the yellow coupling component used in comparative example 3-1, although the coupling components used were different.
Comparative example 3-2, the red coupling component of example 2 was changed from H acid to gamma acid, having the following structural formula; the remainder was identical to example 2.
The detection was performed as described in experiment 2 above, and the results obtained were: the K/S curve and the pattern diagram are shown in FIG. 7, the wavelength corresponding to the maximum K/S value point of the pattern in the curve diagram is 530nm, and the maximum K/S value of dyeing is 3.94. The dry rubbing fastness of the dyed fabric is 4-5 grades, the wet rubbing fastness is 4 grades, the soaping fastness is 4 grades, the dry heat fastness is 4 grades, and the relative fixation rate reaches 84.6%.
As can be seen, the red coupling component used in example 2 was superior in K/S, soaping fastness, fixation ratio, etc. to the red coupling component used in comparative example 3-2, although the coupling components used were different.
Comparative examples 3-3, the blue coupling component of example 3 was changed from an H acid disodium salt derivative to an H acid derivative 1, having the following structural formula; the remainder was identical to example 3.
The detection was performed as described in experiment 3 above, and the results obtained were: the K/S curve and the pattern diagram are shown in FIG. 8, the wavelength corresponding to the maximum K/S value point of the pattern in the curve diagram is 600nm, and the maximum K/S value of dyeing is 4.78. The dry rubbing fastness of the dyed fabric is 4-5 grades, the wet rubbing fastness is 4 grades, the soaping fastness is 4 grades, the dry heat fastness is 4 grades, and the relative fixation rate reaches 85.1 percent.
As can be seen, the blue coupling component used in example 3 was superior in K/S, fastness to washing, fixation, etc. to the blue coupling component used in comparative examples 3-3, although the coupling components used were different.
The comparison of the above cases is shown in table 1 below.
TABLE 1
Finally, it should also be noted that the above list is merely a few specific embodiments of the present invention. Obviously, the invention is not limited to the above embodiments, but many variations are possible. All modifications directly derived or suggested to one skilled in the art from the present disclosure should be considered as being within the scope of the present invention.
Claims (9)
1. An arylamine modification and a dyeing method for cellulose fiber, which are characterized by comprising the following steps:
1) Isatoic anhydride modified cellulose fibers:
in a solvent, carrying out modification reaction on cellulose fibers and isatoic anhydride, wherein the dosage of the isatoic anhydride is 1-10% of the mass of the cellulose fibers; the reaction temperature is 100+/-10 ℃, and the reaction time is 6+/-0.5 h;
then post-treatment is carried out to obtain isatoic anhydride modified cellulose;
2) Diazotisation of isatoic anhydride modified cellulose:
diazotizing isatoic anhydride modified cellulose obtained in the step 1) to obtain diazotized cellulose;
3) Coupling staining of diazotized cellulose:
mixing a coupling component, sodium hydroxide, sodium carbonate and water to form a coupling component solution, wherein the concentration of the coupling component in the coupling component solution is 2+/-0.2 g/L, the concentration of sodium hydroxide is 0.1-2 g/L, and the concentration of sodium carbonate is 0.5-5 g/L;
reacting the diazotized cellulose fiber obtained in the step 2) with a coupling component solution to generate a coupling dyed fiber; the coupling dyeing bath ratio is 1:20 to 100.
2. The arylamine modification and dyeing method for cellulose fibers according to claim 1, wherein:
the coupling component is a yellow coupling component, a red coupling component and a blue coupling component;
the yellow coupling component is 1- (2, 5-dichloro-4-sulfophenyl) -3-methyl-5-pyrazolone, and the structural formula is as follows:
the red coupling component is H acid, and the structural formula is as follows:
the blue coupling component is an H acid disodium salt derivative, and the structural formula is as follows:
3. the arylamine modification and dyeing method for cellulose fibers according to claim 2, characterized in that: the solvent in the step 1) is N, N-dimethylformamide.
4. The arylamine modification and dyeing method according to claim 3, characterized in that the post-treatment in said step 1) is:
firstly, cleaning in hot water at 60+/-10 ℃ and then washing with cold water at 5-10 ℃; obtaining isatoic anhydride modified cellulose.
5. The arylamine modification and dyeing method for cellulose fibers according to any one of claims 1-4, characterized in that said step 2):
adding isatoic anhydride modified cellulose obtained in the step 1) into a hydrochloric acid aqueous solution, and then adding NaNO 2 Stirring the aqueous solution at room temperature for reaction for 10-30 min; the HCl and NaNO 2 The molar ratio of (2) is 1: (1.01.+ -. 0.01) mol of HCl is added per 1g of cellulose fiber (0.001.+ -. 0.0001);
taking out the reacted cellulose, washing with water, and drying to obtain the diazotized cellulose.
6. The arylamine modification and dyeing method for cellulose fibers according to claim 5, characterized in that said step 3):
under continuous oscillation, the diazotized cellulose obtained in the step 2) is put into a coupling component solution to be soaked for 10-20 min at room temperature, so that dyeing is realized, and coupling dyed fibers are generated;
and then, washing the coupled dyed fiber with water, and airing to obtain the dyed cellulose fiber.
7. The arylamine modification and dyeing method for cellulose fiber according to claims 1-6, characterized in that the cellulose fiber is any one of the following:
natural fibers, man-made fibers, blends of natural and man-made fibers.
8. The arylamine modification and dyeing method for cellulose fibers according to claim 7, wherein:
the natural fiber is any one of the following: cotton, hemp and bamboo fiber;
the artificial fiber is viscose fiber.
9. The arylamine modification and dyeing method according to any one of claims 6-8, characterized in that the water washing in step 3) is alternately performed with hot water washing at 60±10 ℃ and cold water washing at 5-10 ℃.
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