CN117402506A - Yellow reactive dye and preparation method thereof - Google Patents
Yellow reactive dye and preparation method thereof Download PDFInfo
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- CN117402506A CN117402506A CN202311350439.2A CN202311350439A CN117402506A CN 117402506 A CN117402506 A CN 117402506A CN 202311350439 A CN202311350439 A CN 202311350439A CN 117402506 A CN117402506 A CN 117402506A
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- reactive dye
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- yellow
- yellow reactive
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- 239000000985 reactive dye Substances 0.000 title claims abstract description 84
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 239000000975 dye Substances 0.000 claims abstract description 70
- 229920003043 Cellulose fiber Polymers 0.000 claims abstract description 45
- 238000005859 coupling reaction Methods 0.000 claims abstract description 42
- 230000008878 coupling Effects 0.000 claims abstract description 32
- 238000010168 coupling process Methods 0.000 claims abstract description 32
- 239000012954 diazonium Substances 0.000 claims abstract description 23
- 150000001989 diazonium salts Chemical class 0.000 claims abstract description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000007639 printing Methods 0.000 claims abstract description 12
- 239000000243 solution Substances 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 239000004744 fabric Substances 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
- 229920000742 Cotton Polymers 0.000 claims description 15
- 239000000835 fiber Substances 0.000 claims description 15
- 229920000297 Rayon Polymers 0.000 claims description 14
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 14
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 14
- 239000002270 dispersing agent Substances 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- 238000004043 dyeing Methods 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- -1 2 Chemical class 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- 238000001035 drying Methods 0.000 claims description 7
- WQHQCQSAAOGHQP-UHFFFAOYSA-N formaldehyde;2-methylnaphthalene-1-sulfonic acid Chemical group O=C.C1=CC=CC2=C(S(O)(=O)=O)C(C)=CC=C21 WQHQCQSAAOGHQP-UHFFFAOYSA-N 0.000 claims description 7
- 235000010288 sodium nitrite Nutrition 0.000 claims description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 7
- 235000011152 sodium sulphate Nutrition 0.000 claims description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 150000001340 alkali metals Chemical class 0.000 claims description 6
- 239000011734 sodium Substances 0.000 claims description 6
- 238000006193 diazotization reaction Methods 0.000 claims description 5
- 238000000227 grinding Methods 0.000 claims description 5
- 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 5
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 4
- 101150065749 Churc1 gene Proteins 0.000 claims description 4
- 102100038239 Protein Churchill Human genes 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 230000008034 disappearance Effects 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 230000001105 regulatory effect Effects 0.000 claims description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 239000002994 raw material Substances 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 239000003513 alkali Substances 0.000 abstract description 20
- DFRAKQKBZGHDES-UHFFFAOYSA-N S(=O)(=O)(O)O.C(=C)S(=O)(=O)C=C Chemical compound S(=O)(=O)(O)O.C(=C)S(=O)(=O)C=C DFRAKQKBZGHDES-UHFFFAOYSA-N 0.000 abstract description 16
- 125000001309 chloro group Chemical group Cl* 0.000 abstract description 11
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 abstract description 8
- 125000000542 sulfonic acid group Chemical group 0.000 abstract description 8
- 125000000129 anionic group Chemical group 0.000 abstract description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 16
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 14
- 238000012360 testing method Methods 0.000 description 8
- MBDUIEKYVPVZJH-UHFFFAOYSA-N 1-ethylsulfonylethane Chemical compound CCS(=O)(=O)CC MBDUIEKYVPVZJH-UHFFFAOYSA-N 0.000 description 6
- 150000004982 aromatic amines Chemical class 0.000 description 6
- 239000001043 yellow dye Substances 0.000 description 6
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 238000006277 sulfonation reaction Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 3
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical group C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 3
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- FHXUYFKYRBLZJU-UHFFFAOYSA-N 3-(5-methyl-3-oxo-1h-pyrazol-2-yl)benzenesulfonic acid Chemical compound N1C(C)=CC(=O)N1C1=CC=CC(S(O)(=O)=O)=C1 FHXUYFKYRBLZJU-UHFFFAOYSA-N 0.000 description 2
- TYCNXOAPQGVAQU-UHFFFAOYSA-N 5-oxo-1-(4-sulfophenyl)-4h-pyrazole-3-carboxylic acid Chemical compound O=C1CC(C(=O)O)=NN1C1=CC=C(S(O)(=O)=O)C=C1 TYCNXOAPQGVAQU-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 125000006575 electron-withdrawing group Chemical group 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 125000003226 pyrazolyl group Chemical group 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- LUZXGSRCYGQGQF-UHFFFAOYSA-N 2,5-dichloro-4-(5-methyl-3-oxo-1h-pyrazol-2-yl)benzenesulfonic acid Chemical compound N1C(C)=CC(=O)N1C1=CC(Cl)=C(S(O)(=O)=O)C=C1Cl LUZXGSRCYGQGQF-UHFFFAOYSA-N 0.000 description 1
- 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 1
- QQNXPCCFPQRLMK-UHFFFAOYSA-N S(O)(O)(=O)=O.OCCS(=O)(=O)CCO Chemical compound S(O)(O)(=O)=O.OCCS(=O)(=O)CCO QQNXPCCFPQRLMK-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000010409 ironing Methods 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- WDFVICOGUPEJEQ-UHFFFAOYSA-N pyrazol-3-one;hydrochloride Chemical compound Cl.O=C1C=CN=N1 WDFVICOGUPEJEQ-UHFFFAOYSA-N 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011265 semifinished product Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000007704 transition Effects 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/503—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an esterified or non-esterified hydroxyalkyl sulfonyl or mercaptoalkyl sulfonyl group, a quaternised or non-quaternised aminoalkyl sulfonyl group, a heterylmercapto alkyl sulfonyl group, a vinyl sulfonyl or a substituted vinyl sulfonyl group, or a thiophene-dioxide group
- C09B62/507—Azo dyes
- C09B62/51—Monoazo 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
- 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
- D06P1/38—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 reactive 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
- D06P3/58—Material containing hydroxyl groups
- D06P3/60—Natural or regenerated cellulose
- D06P3/66—Natural or regenerated cellulose using reactive dyes
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
The invention discloses a yellow reactive dye and a preparation method thereof, wherein the reactive dye is shown in a structural general formula (I). The reactive dye is prepared by taking pyrazolone derivative containing 2 chlorine atoms and two anionic water-soluble groups (sulfonic acid groups and carboxyl groups) as a coupling component and reacting with diazonium salt containing vinyl sulfone sulfate active groups. The color light of the final dye is yellow and bright due to the electron-withdrawing effect of two chlorine atoms, and the water solubility of the dye is effectively improved, the alkali-resistant stability of the dye is improved, the problems of insufficient Huang Yan color and poor alkali-resistant stability in printing of the cellulose fibers of the existing commercial reactive dyes with the same color are solved, and the dye has wide application prospect.
Description
Technical Field
The invention relates to the technical field of reactive dyes, in particular to a yellow reactive dye and a preparation method thereof.
Background
Reactive dyes have a reactive group (active group) in their molecular structure, and are capable of reacting with hydroxyl groups on cellulose fibers or amino groups on protein fibers, and fabrics dyed or printed have excellent wet rubbing fastness, so that the reactive dyes are widely used for dyeing cellulose fibers and protein fibers.
The color light of the reactive dye has important influence on the application of the dye, and particularly the demand on the brightness of the reactive dye is higher. In the practical application process of the reactive yellow dye, the more Huang Yan the reactive dye is popular in the market. In addition, reactive dyes are often required to be fixed under alkaline conditions, and the alkali-resistant stability of the dye is also an important application property of the dye.
Yellow reactive dyes using pyrazolone compounds as coupling components are important varieties in reactive dyes at present. KN reactive dyes (dyes containing only vinyl sulfone sulfate active groups) prepared from pyrazolone coupling components and diazonium components with aromatic amines containing vinyl sulfone sulfate active groups can be divided into two classes.
The first group is to use pyrazolone compounds without chlorine atoms as coupling components: namely, a monoazo KN-type reactive dye is prepared by taking 1- (3 '-sulfophenyl) -3-methyl-5-pyrazolone, 1- (4' -sulfophenyl) -3-carboxyl-5-pyrazolone and the like as coupling components and taking arylamine containing vinyl sulfone sulfate as diazonium salt. The dye lacks strong electron-withdrawing groups in the coupling component, so that the dyed fabric has the problem of yellow and bright color.
In addition, the reactive dyes prepared by using 1- (3 '-sulfophenyl) -3-methyl-5-pyrazolone and 1- (4' -sulfophenyl) -3-methyl-5-pyrazolone as coupling components have poor alkali resistance stability because the coupling components only contain 1 sulfoacid group and the dye prepared by reacting with aromatic amine diazonium salt containing vinyl sulfone sulfate active group contains 2 anionic groups (sulfonic acid group and vinyl sulfone sulfate group). The main reason is that the vinyl sulfone sulfate is a temporary soluble group, hydrophilic sulfate groups can be removed under alkaline conditions to generate hydrophobic vinyl sulfone groups, the problem of poor alkali resistance stability exists, the water solubility of the dye can be greatly reduced, the dye is separated from the solution to influence the practical application effect, and the quality of the colored fabric is unqualified and the color light is insufficient Huang Yan.
The molecular structure of the 1- (4' -sulfophenyl) -3-carboxyl-5-pyrazolone coupling component contains two anionic groups of carboxyl and sulfonic acid groups, and the dye prepared by the reaction of the coupling component and the diazonium salt of the aromatic amine containing vinyl sulfone sulfate active groups contains 3 anionic groups (carboxyl, sulfonic acid groups and vinyl sulfone sulfate groups), so that the prepared dye has good alkali resistance stability, but the problem of insufficient yellow and brilliant color of dyed fabrics still exists. Therefore, the first problem that the reactive dye prepared by taking the pyrazolone compound without chlorine atoms as a coupling component is not yellow and bright enough in color is solved from the aspect of molecular structure design.
The second group is to use pyrazolone compounds containing chlorine atoms as coupling components: namely, monoazo KN-type reactive dyes are prepared by taking 1- (2 ',5' -dichloro-4 '-sulfophenyl) -3-methyl-5-pyrazolone, 1- (2' -chloro-4 '-sulfogroup-6' -methylphenyl) -3-methyl-5-pyrazolone and the like as coupling components and taking arylamine containing vinyl sulfone sulfate as diazonium salt. The coupling component contains chlorine atoms with strong electronegativity, and the final dye dyes the color cast Huang Yan of the fabric, but the dye has the problem of poor alkali resistance and stability. This is still because the coupling component contains only 1 sulfonic acid group and the dye prepared by reaction with an aromatic amine diazonium salt containing a vinyl sulfone sulfate active group contains only 2 anionic groups (sulfonic acid groups and temporary vinyl sulfone sulfate groups) and the hydrophilic sulfate groups are removed from the vinyl sulfone sulfate under alkaline conditions to form hydrophobic vinyl sulfone groups.
Therefore, how to design the molecular structure of the dye to have more gorgeous color and high alkali resistance stability is the target pursued by the current dye and printing and dyeing enterprises.
Disclosure of Invention
The invention aims to provide a yellow reactive dye with high performance and bright yellow light, which solves the problems of insufficient color light Huang Yan and poor alkali resistance stability of the yellow reactive dye in the background art.
In order to achieve the above purpose, the present invention provides the following technical solutions:
the first aspect of the invention provides a yellow reactive dye, which has the following structural general formula (I):
in the general formula (I),
R 1 is-H, -OCH 3 or-CH 3 ；
R 2 is-H, -OCH 3 or-SO 3 M；
R 3 is-SO 2 CH 2 CH 2 OSO 3 M、–SO 2 CHCH 2 、–CONHCH 2 CH 2 SO 2 CH 2 CH 2 OSO 3 M、–NHCOCH 2 CH 2 CH 2 SO 2 CH 2 CH 2 Cl or-NHCOCH 2 CH 2 CH 2 SO 2 CHCH 2 ；
M is-H or an alkali metal.
In a possible implementation of the first aspect, in the structural general formula (i) of the yellow reactive dye, R 1 is-H or-CH 3 ；R 2 is-H, -OCH 3 or-SO 3 M；R 3 is-SO 2 CH 2 CH 2 OSO 3 M、–CONHCH 2 CH 2 SO 2 CH 2 CH 2 OSO 3 M or-NHCOCH 2 CH 2 CH 2 SO 2 CH 2 CH 2 Cl; m is-H or an alkali metal.
In a possible implementation of the first aspect, in the structural general formula (i) of the yellow reactive dye, R 1 is-H or-CH 3 ；R 2 is-H, -OCH 3 or-SO 3 M；R 3 is-SO 2 CH 2 CH 2 OSO 3 M; m is-H or an alkali metal.
In a possible implementation of the first aspect, in the structural general formula (i) of the yellow reactive dye, R 1 is-H or-CH 3 ；R 2 is-H, -OCH 3 or-SO 3 M；R 3 is-SO 2 CH 2 CH 2 OSO 3 M; m is Na, K or Li.
In a possible implementation of the first aspect, in the structural general formula (i) of the yellow reactive dye, R 1 is-H; r is R 2 is-H or-SO 3 M；R 3 is-SO 2 CH 2 CH 2 OSO 3 M; m is Na or K.
In a possible implementation of the first aspect, in the structural general formula (i) of the yellow reactive dye, R 1 is-H; r is R 2 is-H; r is R 3 is-SO 2 CH 2 CH 2 OSO 3 M; m is Na.
The second aspect of the present invention provides a commercial dye prepared by using the yellow reactive dye, wherein the commercial dye comprises the following raw material components in percentage by mass: 75-85% of yellow reactive dye, 5-15% of dispersing agent, 0.1-0.5% of dustproof agent and 5-15% of anhydrous sodium sulphate.
In one possible implementation of the second aspect, the diffusing agent is a methylnaphthalene sulfonic acid formaldehyde condensate; the dustproof agent is a water-soluble high molecular compound.
A third aspect of the present invention provides the use of a commercial dye as described above for dyeing and printing cellulosic fibres;
the cellulose fibers are hydroxyl-containing, and/or nitrogen-containing cellulose fibers.
In a possible implementation of the third aspect, the cellulose fibers are cotton fibers, viscose fibers or a cotton and viscose mixed fabric.
A fourth aspect of the present invention provides a method for preparing the yellow reactive dye, comprising the steps of:
(1) Diazotisation reaction
Adding an arylamine compound a, crushed ice and a small amount of water into a reaction vessel for ice grinding treatment; adding concentrated hydrochloric acid, stirring, then dropwise adding sodium nitrite aqueous solution, and carrying out diazotization reaction; after the reaction is finished, sulfamic acid is added to prepare a solution of diazonium salt b of the arylamine compound;
(2) Coupling reaction
Adding the solution of the coupling component c into the solution of the diazonium salt b in the step (1), and reacting for 2-4 hours at the temperature of 0-5 ℃ and the condition of pH=6.0-6.5 to obtain a coupling product;
(3) Drying treatment
And (3) drying and grinding the coupling product prepared in the step (2) at the temperature of 70-80 ℃ to obtain the yellow reactive dye solid powder shown in the final compound (I).
In one possible implementation of the fourth aspect, in the diazotizing reaction in step (1), the molar ratio of the compound a to the sodium nitrite solution is 1:1 to 1:1.02;
the molar ratio of the compound a to the hydrochloric acid solution is 1:0.5-1:1.8.
And/or after the sodium nitrite solution is dripped in the diazotization reaction, continuing the reaction for 1 to 1.5 hours;
and/or, the endpoint of the diazotisation reaction is detected by an ehrling reagent, and excess nitrous acid is removed by sulfamic acid.
In one possible implementation of the fourth aspect, in the coupling reaction of step (2), the molar ratio of diazonium salt b to solution of coupling component c is from 1:0.98 to 1:1;
and/or regulating the pH value of the coupling reaction to be between 6.0 and 6.5 by using sodium bicarbonate;
and/or detecting the coupling reaction by a permeation ring method, and taking the disappearance of the diazonium salt b as a reaction end point.
Compared with the prior art, the invention has the beneficial technical effects that:
1. the reactive dye is monoazo KN reactive dye prepared by taking 1- (2 ',5' -dichloro-4 ' -sulfoacid phenyl) -3-carboxyl-5-pyrazolone as a coupling component and taking arylamine containing vinyl sulfone sulfate as diazonium salt. Compared with the existing dye of the first pyrazolone coupling component without chlorine atoms, the coupling component of the dye contains two chlorine atoms, and the two chlorine atoms have larger electronegativity and electron-withdrawing effect, so that the electron-withdrawing group can reduce the pi-pi transition energy level of dye molecules, and the absorption spectrum of the dye molecules is red shifted. Because the two chlorine atoms are on the benzene ring and have a certain space distance from the pyrazole ring, and the benzene ring and the pyrazole ring are connected through a single bond, the electron transfer effect is weakened, so that the total result is that the visible absorption spectrum of dye molecules generates a slight red shift phenomenon (about 8-10 nm), after the dye is finally used for dyeing the cloth sample, the color of the dyed cloth sample is the reflection spectrum of the dye, and the reflection spectrum is inevitably deviated from Huang Yan due to the slight red shift of the visible absorption spectrum of the dye, so that the color light of the finally dyed fabric is deviated from Huang Yan.
2. In contrast to the pyrazolone coupling component dyes of the second class containing chlorine atoms, the coupling component of the yellow reactive dyes according to the invention contains 1 carboxyl group in addition to 1 sulfonic acid group. The yellow reactive dye prepared after diazo salt with aromatic amine containing vinyl sulfone sulfate active group contains 3 anionic groups, and even if the temporary soluble vinyl sulfone sulfate removes sulfate groups to generate hydrophobic vinyl sulfone groups in dyeing application, the coupling component still contains 2 anionic groups of carboxyl and sulfonic acid groups, and at the moment, the two water-soluble groups can also keep high solubility of the dye in water, so that the dye has excellent alkali-resistant stability.
Therefore, the yellow reactive dye provided by the invention not only meets the requirement that the dye has high alkali resistance stability, but also ensures the chromatic light bias Huang Yan of dyed fabrics.
Detailed Description
The technical solutions of the embodiments of the present invention will be clearly and completely described below with reference to the embodiments, and it is apparent that the described embodiments are only some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
Example 1
Illustrative embodiments of the present application include, but are not limited to, a yellow reactive dye and a method of preparing the same, and commercial dyes prepared using the yellow reactive dye and applications thereof.
The embodiment discloses a yellow reactive dye which has the following molecular structural formula (I-1):
the embodiment also discloses a commercial dye prepared by using the yellow reactive dye, wherein the commercial reactive dye is prepared by mixing the yellow reactive dye with a general structure (I-1) with a dispersing agent (wherein the dispersing agent is a methyl naphthalene sulfonic acid formaldehyde condensate, the condensation degree is 4, the sulfonation degree is 2), a water-based polymer dustproof agent and anhydrous sodium sulphate according to the mass percentage of 85%, 5%, 0.1% and 9.9%.
The commercial dye is used for dyeing and printing cellulose fibers, wherein the cellulose fibers are hydroxyl-containing and/or nitrogen-containing cellulose fibers, namely, the cellulose fibers are hydroxyl-containing or nitrogen-containing cellulose fibers or any one of hydroxyl-containing or nitrogen-containing cellulose fibers. Further, the cellulose fiber in this embodiment is cotton fiber, viscose fiber or cotton and viscose fiber mixed fabric.
The embodiment discloses a preparation method of a yellow reactive dye, which has a structural general formula (I-1), and comprises the following steps:
(1) Diazotisation reaction
28.1g of 3- (. Beta. -sulfate ethylsulfone) aniline (meta-ester) folded 100%, 200g of ice and 20mL of water were added to a 1000mL beaker and ice-milled for 2 hours. 12.2g of technical hydrochloric acid (30%) were added and the reaction stirred for 1 hour. After dissolving 7.0g of 100% sodium nitrite solid in 30mL of water, the solution was slowly added dropwise into a beaker, and the reaction solution was kept slightly blue during the addition by using Congo red test paper, and the KI test paper was slightly blue. After the dripping is finished, keeping the temperature of the reaction system between 0 and 5 ℃, continuing to react for 1 hour, detecting the end point of the reaction by using an ehrling reagent, and removing excessive nitrous acid by using sulfamic acid after the reaction is finished to prepare the diazonium salt solution of para-ester.
(2) Coupling reaction
Adding 35.19g of folded 1- (2 ',5' -dichloro-4 ' -sulfophenyl) -3-carboxyl-pyrazolone solution into the para-ester diazonium salt solution prepared in the step (1), regulating the pH value of the reaction to be between 5.8 and 6.5 by using sodium bicarbonate, controlling the reaction temperature to be less than 15 ℃, carrying out coupling reaction for 3 hours, and detecting the reaction by a ring permeation method, wherein the disappearance of meta-ester diazonium salt is taken as the end point.
(3) Drying treatment
And (3) drying and grinding the coupling product prepared in the step (2) at the temperature of 75 ℃ to obtain yellow reactive dye solid powder shown in the final compound (I-1).
The reactive dyes of examples 1 and 2 were tested for their performance with the commercial dye c.i. reactive yellow 42, and in particular, in this example, the reactive dye printing process was used to test the fixation rate, the respective color fastness, and the color performance of the reactive dyes of examples 1 and 2 of the same type of structure as the commercial dye c.i. reactive yellow 42 (with no pyrazolone chloride as the coupling component, the structure is as follows), and to perform a performance comparison. The results of the product performance tests are shown in tables 1 and 2.
Wherein the molecular structure of the commercial dye c.i. reactive yellow 42 is as follows:
printing paste prescription: dye 5g, urea 5g, baking soda 2.5g, sodium alginate paste 60g, anti-staining salt 1g, and water 100g in total.
The process flow comprises the following steps: semi-finished product, reactive pulp printing, drying, steaming (102 ℃ C. For 7min, relative humidity of 75%), water washing, soaping, water washing and ironing.
The testing method comprises the following steps:
the fixation rate of the dye is measured according to GB/T2391-2014 'measurement of fixation rate of reactive dye'; determining the rub-fastness of the fabric according to GB/T3920-2008 "rubbing-fastness for textile color fastness test"; the solubility of the dye was determined according to GB/T21879-2015 "determination of Water-soluble dye-solubility-spot Filter paper method".
Apparent color depth and color properties of the dye:
the apparent colour depth (inters value) and colour data (CIELab value, brightness value L, red-green light a, yellow-blue light b, saturation C, hue angle h) of the dyed fabric were determined by means of a Datacolor SF600 colorimeter 0 ). The test light source was D65, the angle of view was 10℃and the measurement was carried out 4 times on the dyed cotton fabric, and the average value was taken.
TABLE 1
As can be seen from the data in Table 1, the reactive yellow dye provided by the invention has high solubility (> 200 g/L) and alkali resistance stability (> 120 min), and has consistent fastness properties compared with C.I. reactive yellow 42, and the improvement performance (Integ value) of the dye is slightly higher than that of the C.I. reactive yellow 42. Thus, the reactive yellow dyes provided herein are capable of meeting the market demand for application properties.
TABLE 2
As can be seen from the data in table 2, the reactive yellow dyes provided in examples 1 and 2 of the present invention have higher brightness and brilliance values (example 1:L =89.438; c= 92.343; example 2:L =89.368; c= 94.967) compared to c.i. reactive yellow 42, and the dyes are found to be more yellowish green (example 1:a =4.815; b= 92.218; example 2:a =4.333; b= 94.868) based on the red-green and yellow-blue color values of the dye. Thus, the reactive yellow dyes provided herein are more yellow in color than existing types of structures.
The alkali stability test was carried out on the reactive dyes of example 1 and example 2 and reactive yellow WN (using chlorinated pyrazolone as coupling component, structure as follows), and the results are shown in Table 3.
Wherein the molecular structure of active yellow WN is as follows:
the testing method comprises the following steps: the alkali-resistant stability of the dye was determined according to GB/T29597-2013 determination of alkali-resistant stability of reactive dyes.
TABLE 3 Table 3
As can be seen from Table 3, the solubility of active yellow WN is less than 120g/L, the dye is separated out from the solution within 20min after alkali is added, and the alkali-resistant stability is poor, while the active dye provided by the invention has excellent alkali-resistant stability, and the alkali-resistant stability time t is more than 120min.
In summary, the test data in tables 1, 2 and 3 show that the reactive yellow dye provided by the application not only has excellent alkali resistance and various color fastness properties, but also dyes a fabric color tube of more Huang Yan.
Example 2
The embodiment discloses a yellow reactive dye which has the following molecular structural formula (I-2):
the embodiment also discloses a commercial dye prepared by using the yellow reactive dye, wherein the commercial dye is prepared by mixing the yellow reactive dye with a general structure (I-2) with a dispersing agent (wherein the dispersing agent is a methyl naphthalene sulfonic acid formaldehyde condensate, the condensation degree is 4, the sulfonation degree is 2), a water-based polymer dustproof agent and anhydrous sodium sulphate according to the mass percentage of 85%, 5%, 0.1% and 9.9%.
The commercial dye is used for dyeing and printing cellulose fibers, wherein the cellulose fibers are hydroxyl-containing and/or nitrogen-containing cellulose fibers, namely, the cellulose fibers are hydroxyl-containing or nitrogen-containing cellulose fibers or any one of hydroxyl-containing or nitrogen-containing cellulose fibers. Further, the cellulose fiber in this embodiment is cotton fiber, viscose fiber or cotton and viscose fiber mixed fabric.
The preparation method of the yellow reactive dye with the general structure (I-2) in this example is the same as that of example 1, except that 4- (beta-sulfate ethyl sulfone) aniline (para-ester) is used in this example to replace 3- (beta-sulfate ethyl sulfone) aniline (meta-ester) in the preparation step (1) of example 1, so that the corresponding diazonium salt solution is prepared, and then the final reactive dye is prepared.
Example 3
The embodiment discloses a yellow reactive dye which has the following molecular structural formula (I-3):
the embodiment also discloses a commercial dye prepared by using the yellow reactive dye, wherein the commercial dye is prepared by mixing the yellow reactive dye with a general structure (I-3) with a dispersing agent (wherein the dispersing agent is a methyl naphthalene sulfonic acid formaldehyde condensate, the condensation degree is 4, the sulfonation degree is 2), a water-based polymer dustproof agent and anhydrous sodium sulphate according to the mass percentage of 85%, 5%, 0.1% and 9.9%.
The commercial dye is used for dyeing and printing cellulose fibers, wherein the cellulose fibers are hydroxyl-containing and/or nitrogen-containing cellulose fibers, namely, the cellulose fibers are hydroxyl-containing or nitrogen-containing cellulose fibers or any one of hydroxyl-containing or nitrogen-containing cellulose fibers. Further, the cellulose fiber in this embodiment is cotton fiber, viscose fiber or cotton and viscose fiber mixed fabric.
The preparation method of the yellow reactive dye with the general structure (I-3) in the embodiment is the same as that of the embodiment 1, except that 2-aminoanisole-4-beta-hydroxyethyl sulfonyl sulfate (o-methoxy para-ester) is used for replacing 3- (beta-sulfate ethyl sulfone) aniline (meta-ester) in the preparation step (1) in the embodiment 1, wherein the amount of industrial hydrochloric acid is 18.25g, and the final reactive dye is prepared after the corresponding diazonium salt solution is prepared.
Example 4
The embodiment discloses a yellow reactive dye which has the following molecular structural formula (I-4):
the embodiment also discloses a commercial dye prepared by using the yellow reactive dye, wherein the commercial dye is prepared by mixing the yellow reactive dye with a general structure (I-4) with a dispersing agent (wherein the dispersing agent is a methyl naphthalene sulfonic acid formaldehyde condensate, the condensation degree is 4, the sulfonation degree is 2), a water-based polymer dustproof agent and anhydrous sodium sulphate according to the mass percentage of 85%, 5%, 0.1% and 9.9%.
The commercial dye is used for dyeing and printing cellulose fibers, wherein the cellulose fibers are hydroxyl-containing and/or nitrogen-containing cellulose fibers, namely, the cellulose fibers are hydroxyl-containing or nitrogen-containing cellulose fibers or any one of hydroxyl-containing or nitrogen-containing cellulose fibers. Further, the cellulose fiber in this embodiment is cotton fiber, viscose fiber or cotton and viscose fiber mixed fabric.
The yellow reactive dye having the general structure (I-4) in this example was prepared in the same manner as in example 1, except that 2- [ (4-amino-5-methoxy-2-methylphenyl) sulfonyl ] hydrosulfide (clecidine para-ester) was used instead of 3- (. Beta. -sulfate ethylsulfone) aniline (meta-ester) in the preparation step (1) of example 1, wherein the amount of industrial hydrochloric acid was 18.25g, and the corresponding diazonium salt solution was prepared, and then the final reactive dye was prepared.
Example 5
The embodiment discloses a yellow reactive dye which has the following molecular structural formula (I-5):
the embodiment also discloses a commercial dye prepared by using the yellow reactive dye, wherein the commercial dye is prepared by mixing the yellow reactive dye with a general structure (I-4) with a dispersing agent (wherein the dispersing agent is a methyl naphthalene sulfonic acid formaldehyde condensate, the condensation degree is 4, the sulfonation degree is 2), a water-based polymer dustproof agent and anhydrous sodium sulphate according to the mass percentage of 85%, 5%, 0.1% and 9.9%.
The commercial dye is used for dyeing and printing cellulose fibers, wherein the cellulose fibers are hydroxyl-containing and/or nitrogen-containing cellulose fibers, namely, the cellulose fibers are hydroxyl-containing or nitrogen-containing cellulose fibers or any one of hydroxyl-containing or nitrogen-containing cellulose fibers. Further, the cellulose fiber in this embodiment is cotton fiber, viscose fiber or cotton and viscose fiber mixed fabric.
The preparation method of the yellow reactive dye with the general structure (I-5) in this example is the same as that of example 1, except that 2, 5-dimethoxy-4- (beta-hydroxyethyl sulfone sulfate) aniline (2, 5-dimethoxy para-ester) is used in this example to replace 3- (beta-sulfate ethyl sulfone) aniline (meta-ester) in the preparation step (1) in example 1, wherein the amount of industrial hydrochloric acid is 21.0g, and the final reactive dye is prepared after the corresponding diazonium salt solution is prepared.
The above description of the specific embodiments of the present invention has been given by way of example only, and the present invention is not limited to the above described specific embodiments. Any equivalent modifications and substitutions for the present invention will occur to those skilled in the art, and are also within the scope of the present invention. Accordingly, equivalent changes and modifications are intended to be included within the scope of the present invention without departing from the spirit and scope thereof.
Claims (13)
1. A yellow reactive dye is characterized by having the following structural general formula (I):
in the general formula (I),
R 1 is-H, -OCH 3 or-CH 3 ；
R 2 is-H, -OCH 3 or-SO 3 M；
R 3 is-SO 2 CH 2 CH 2 OSO 3 M、–SO 2 CHCH 2 、–CONHCH 2 CH 2 SO 2 CH 2 CH 2 OSO 3 M、–NHCOCH 2 CH 2 CH 2 SO 2 CH 2 CH 2 Cl or-NHCOCH 2 CH 2 CH 2 SO 2 CHCH 2 ；
M is-H or an alkali metal.
2. A yellow reactive dye according to claim 1, wherein,
in the structural general formula (I), R is 1 is-H or-CH 3 ；
The R is 2 is-H, -OCH 3 or-SO 3 M；
The R is 3 is-SO 2 CH 2 CH 2 OSO 3 M、–CONHCH 2 CH 2 SO 2 CH 2 CH 2 OSO 3 M or-NHCOCH 2 CH 2 CH 2 SO 2 CH 2 CH 2 Cl；
M is-H or an alkali metal.
3. A yellow reactive dye according to claim 1, wherein,
in the structural general formula (I), R is 1 is-H or-CH 3 The method comprises the steps of carrying out a first treatment on the surface of the The R is 2 is-H, -OCH 3 or-SO 3 M; the R is 3 is-SO 2 CH 2 CH 2 OSO 3 M；
M is-H or an alkali metal.
4. A yellow reactive dye according to claim 1, wherein,
in the structural general formula (I), R is 1 is-H or-CH 3 The method comprises the steps of carrying out a first treatment on the surface of the The R is 2 is-H, -OCH 3 or-SO 3 M; the R is 3 is-SO 2 CH 2 CH 2 OSO 3 M；
And M is Na, K or Li.
5. A yellow reactive dye according to claim 1, wherein,
in the structural general formula (I), R is 1 is-H; the R is 2 is-H or-SO 3 M; the R is 3 is-SO 2 CH 2 CH 2 OSO 3 M；
M is Na or K.
6. A yellow reactive dye according to claim 1, wherein,
in the structural general formula (I), R is 1 is-H; the R is 2 is-H; the R is 3 is-SO 2 CH 2 CH 2 OSO 3 M；
M is Na.
7. A commercial dye prepared from the yellow reactive dye according to any one of claims 1 to 6, characterized in that,
the commercial dye comprises the following raw material components in percentage by mass: 75-85% of yellow reactive dye, 5-15% of dispersing agent, 0.1-0.5% of dustproof agent and 5-15% of anhydrous sodium sulphate.
8. A commercial dye according to claim 7, characterized in that,
the dispersing agent is methyl naphthalene sulfonic acid formaldehyde condensate;
the dustproof agent is a water-soluble high molecular compound.
9. A method according to claim 8, wherein the dye is applied commercially,
the commercial dye is used for dyeing and printing cellulose fibers;
the cellulose fiber is cellulose fiber containing hydroxyl and/or nitrogen.
10. The use of commercial dyes according to claim 9, characterized in that,
the cellulose fiber is cotton fiber, viscose fiber or cotton and viscose fiber mixed fabric.
11. A process for the preparation of a yellow reactive dye according to any one of claims 1 to 6, comprising the steps of:
(1) Diazotisation reaction
Adding an arylamine compound a, crushed ice and a small amount of water into a reaction vessel for ice grinding treatment; adding concentrated hydrochloric acid, stirring, then dropwise adding sodium nitrite aqueous solution, and carrying out diazotization reaction; after the reaction is finished, sulfamic acid is added to prepare a solution of diazonium salt b of the arylamine compound;
(2) Coupling reaction
Adding the solution of the coupling component c into the solution of the diazonium salt b in the step (1), and reacting for 2-4 hours at the temperature of 0-5 ℃ and the condition of pH=6.0-6.5 to obtain a coupling product;
(3) Drying treatment
And (3) drying and grinding the coupling product prepared in the step (2) at the temperature of 70-80 ℃ to obtain the yellow reactive dye solid powder shown in the final compound (I).
12. A process for preparing a yellow reactive dye according to claim 11,
in the diazotization reaction of the step (1), the molar ratio of the compound a to the sodium nitrite solution is 1:1-1:1.02;
the molar ratio of the compound a to the hydrochloric acid solution is 1:0.5-1:1.8.
And/or after the sodium nitrite solution is dripped in the diazotization reaction, continuing the reaction for 1 to 1.5 hours;
and/or, the endpoint of the diazotisation reaction is detected by an ehrling reagent, and excess nitrous acid is removed by sulfamic acid.
13. A process for preparing a yellow reactive dye according to claim 11,
in the coupling reaction of the step (2), the molar ratio of the diazonium salt b to the coupling component c solution is 1:0.98-1:1;
and/or regulating the pH value of the coupling reaction to be between 6.0 and 6.5 by using sodium bicarbonate;
and/or detecting the coupling reaction by a permeation ring method, and taking the disappearance of the diazonium salt b as a reaction end point.
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