CN100362055C - Composite reactive yellow dye - Google Patents
Composite reactive yellow dye Download PDFInfo
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- CN100362055C CN100362055C CNB2006100493714A CN200610049371A CN100362055C CN 100362055 C CN100362055 C CN 100362055C CN B2006100493714 A CNB2006100493714 A CN B2006100493714A CN 200610049371 A CN200610049371 A CN 200610049371A CN 100362055 C CN100362055 C CN 100362055C
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- composite reactive
- reactive yellow
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- 239000002131 composite material Substances 0.000 title claims abstract description 33
- 239000001043 yellow dye Substances 0.000 title claims abstract description 31
- 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 title claims abstract description 29
- 239000000975 dye Substances 0.000 claims abstract description 71
- 229910052783 alkali metal Inorganic materials 0.000 claims description 8
- 150000001340 alkali metals Chemical group 0.000 claims description 8
- 239000011734 sodium Substances 0.000 claims description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 238000004043 dyeing Methods 0.000 abstract description 12
- 239000004744 fabric Substances 0.000 abstract description 7
- 238000000034 method Methods 0.000 description 9
- 239000000835 fiber Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 6
- 229940056729 sodium sulfate anhydrous Drugs 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000005507 spraying Methods 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- DPDMMXDBJGCCQC-UHFFFAOYSA-N [Na].[Cl] Chemical compound [Na].[Cl] DPDMMXDBJGCCQC-UHFFFAOYSA-N 0.000 description 3
- -1 alkyl naphthalene sulfonic acid formaldehyde Chemical compound 0.000 description 3
- 239000012752 auxiliary agent Substances 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000985 reactive dye Substances 0.000 description 3
- PANBYUAFMMOFOV-UHFFFAOYSA-N sodium;sulfuric acid Chemical compound [Na].OS(O)(=O)=O PANBYUAFMMOFOV-UHFFFAOYSA-N 0.000 description 3
- 229920001732 Lignosulfonate Polymers 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229920004935 Trevira® Polymers 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000011010 flushing procedure Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 235000019357 lignosulphonate Nutrition 0.000 description 2
- 239000002932 luster Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- VGKYEIFFSOPYEW-UHFFFAOYSA-N 2-methyl-4-[(4-phenyldiazenylphenyl)diazenyl]phenol Chemical compound Cc1cc(ccc1O)N=Nc1ccc(cc1)N=Nc1ccccc1 VGKYEIFFSOPYEW-UHFFFAOYSA-N 0.000 description 1
- WODGMMJHSAKKNF-UHFFFAOYSA-N 2-methylnaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(C)=CC=C21 WODGMMJHSAKKNF-UHFFFAOYSA-N 0.000 description 1
- SRDOTWUOTQTGAK-UHFFFAOYSA-N C=O.C1(=CC=CC2=CC=CC=C12)S(=O)(=O)OCC1=CC=CC=C1 Chemical compound C=O.C1(=CC=CC2=CC=CC=C12)S(=O)(=O)OCC1=CC=CC=C1 SRDOTWUOTQTGAK-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- MFGOTAHWOBKNNU-XMHGGMMESA-N Isodigeranyl Chemical group CC(C)=CCC\C(C)=C\CC(C)(C=C)CCC=C(C)C MFGOTAHWOBKNNU-XMHGGMMESA-N 0.000 description 1
- MFGOTAHWOBKNNU-FQEVSTJZSA-N Isodigeranyl Natural products CC(=CCCC(=CC[C@](C)(CCC=C(C)C)C=C)C)C MFGOTAHWOBKNNU-FQEVSTJZSA-N 0.000 description 1
- 241000208202 Linaceae Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 1
- 230000002650 habitual effect Effects 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 229960003010 sodium sulfate Drugs 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- STZCRXQWRGQSJD-UHFFFAOYSA-N sodium;4-[[4-(dimethylamino)phenyl]diazenyl]benzenesulfonic acid Chemical compound [Na+].C1=CC(N(C)C)=CC=C1N=NC1=CC=C(S(O)(=O)=O)C=C1 STZCRXQWRGQSJD-UHFFFAOYSA-N 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- UIEBGVDTKLYGTN-UHFFFAOYSA-J tetrasodium;7-[[2-(carbamoylamino)-4-[[4-chloro-6-[3-(2-sulfonatooxyethylsulfonyl)anilino]-1,3,5-triazin-2-yl]amino]phenyl]diazenyl]naphthalene-1,3,6-trisulfonate Chemical group [Na+].[Na+].[Na+].[Na+].C=1C=C(N=NC=2C(=CC3=CC(=CC(=C3C=2)S([O-])(=O)=O)S([O-])(=O)=O)S([O-])(=O)=O)C(NC(=O)N)=CC=1NC(N=1)=NC(Cl)=NC=1NC1=CC=CC(S(=O)(=O)CCOS([O-])(=O)=O)=C1 UIEBGVDTKLYGTN-UHFFFAOYSA-J 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
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- Coloring (AREA)
Abstract
The invention relates to a composite reactive yellow dye, which consists of 30-99 parts by weight of one or more dyes A shown in a structural formula and 1-70 parts by weight of one or more dyes B shown in a structural formula (II); when the composite reactive yellow dye is used for printing and dyeing, dyed fabrics with high dyeing depth, bright color, light fastness, rubbing fastness and wet fastness can be obtained.
Description
(1) technical field
The present invention relates to a kind of composite reactive yellow dye, relate in particular to a kind of composite reactive yellow dye that is applied to cellulose dyeing.
(2) background technology
Along with the development of fiber species and staining technique, and the raising that the reactive dyestuffs application performance is required, the assembly of multi-active base dyestuff mixes to use and earns widespread respect.A series of reactive black composite dyes are all disclosed as JP7247440A, JP9169923A.As everyone knows, the dyestuff of similar C.I. REACTIVE Yellow 145 structure is a kind of isodigeranyl active base dye, its product dyed thereby possesses fabulous fastness of dyeing, but level-dyeing property, circulation ratio are relatively poor, although piecing together, itself and C.I. reactive yellow 27 mix, can reduce photochromism, but aspect depth, still be weak, thereby color and luster also has much room for improvement.
(3) summary of the invention
The object of the invention is to provide a kind of dye level height, high colour-fast rate and the fabulous composite reactive yellow dye of coloured light vividness.
Composite reactive yellow dye of the present invention, meter by weight, by one or more of 30～99 parts shown in structural formula (I) dyestuff A and one or more dyestuff B shown in structural formula (II) of 1～70 part form;
Its Chinese style (I) and (II) in,
R
1, R
2Independent separately is H, C
1～C
4Alkyl, C
1～C
4Alkoxyl group ,-NHCOR ' or-NHCONH
2, R ' is C
1～C
4Alkyl;
R
3, R
4, R
6, R
7Independent separately is H, C
1～C
4Alkyl, C
1～C
4Alkoxyl group or sulfonic group;
R
5Be H or C
1～C
4Alkyl;
N is 0～3 integer, is preferably 3;
M respectively do for oneself H or alkali metal atom are preferably sodium;
X is-CH=CH
2Or-C
2H
4OSO
3M ', M ' are H or alkali metal atom.
Described R
1Be preferably H, R
2Be preferably-NHCONH
2
Described R
3, R
4, R
5, R
6, R
7Be preferably H separately.
Described X is preferably-C
2H
4OSO
3Na.
The weight fraction of described dyestuff A is preferably 50～90 parts, is preferably 65～85 parts again; The weight fraction of dyestuff B is preferably 5～50 parts, is preferably 10～30 parts again.
Further, the present invention also provides a kind of composite reactive yellow dye, meter by weight, by dyestuff A shown in structural formula (I) of one or more of 30～99 parts, one or more of 1～70 part shown in structural formula (II) dyestuff B and one or more dyestuff C shown in structural formula (III) of 0.1～5 part form:
During its Chinese style (I), (II) reach (III),
R
1, R
2Independent separately is H, C
1～C
4Alkyl, C
1～C
4Alkoxyl group ,-NHCOR ' or-NHCONH
2, R ' is C
1～C
4Alkyl;
R
3, R
4, R
6, R
7Independent separately is H, C
1～C
4Alkyl, C
1～C
4Alkoxyl group or sulfonic group;
R
5Be H or C
1～C
4Alkyl;
R
8Be H, C
1～C
4Alkyl or alkoxyl group;
N is 0～3 integer, and n ' is 1～3 integer;
M is H or alkali metal atom;
X, Z independently are-CH=CH separately
2Or-C
2H
4OSO
3M ', M ' are H or alkali metal atom.
Described R
2Be preferably-NHCONH
2R
1, R
3, R
4, R
5, R
6, R
7, R
8Be preferably H separately; N is preferably 3; N ' is preferably 2; M is preferably sodium; X, Z are preferably-C separately
2H
4OSO
3Na.
The weight fraction of described dyestuff A is preferably 50～90 parts, is preferably 65～85 parts again; The weight fraction of dyestuff B is preferably 5～50 parts, is preferably 10～30 parts again; The weight fraction of dyestuff C is preferably 0.1～3 part.
Composite reactive yellow dye of the present invention can prepare with ordinary method, for example generally with each single dyestuff A of mechanically mixing, B, C.This single dyestuff can powdery, the aqueous solution form of granular, resulting solution or each dyestuff exists.Single dyestuff A, B, C can describe it respectively as U.S. Pat 4378313, Japanese Patent JP03-064370 and JP07-247440 with known method preparation.
When being applied to dye, described composite reactive yellow dye generally need add the reactive dyestuffs used additives and piece together mixedly, and described auxiliary agent can be the mixture of one of following or its arbitrary proportion: dispersion agent, diffusant, weighting agent.Dispersion agent, diffusant such as naphthalene sulfonic acidformaldehyde condensation product (NNO), alkyl naphthalene sulfonic acid formaldehyde condensation products, sulfonated lignin.Alkyl naphthalene sulfonic acid formaldehyde condensation products such as Dispersant MF (condensation compound of methyl naphthalene sulfonic acid and formaldehyde), dispersing agent CNF (benzyl naphthalenesulfonate formaldehyde condensation compound) etc., sulfonated lignin such as sodium lignosulfonate (as commercial dispersants Reax 83A, Reax 85A); Weighting agent such as Sodium sulfate anhydrous.min(99) (industrial sulphuric acid sodium) etc., described auxiliary agent is preferably industrial sulphuric acid sodium.
The preparation that composite reactive yellow dye of the present invention can be used as powdery or granular solid-state form, liquid form exists, they generally comprise water-soluble and the habitual electrolytic salt of fibre-reactive dyes particularly under solid-state form, such as sodium-chlor, Repone K and sodium sulfate etc., and can further comprise the auxiliary agent that commercial dye is commonly used.
Yellow reactive dyes preparation of the present invention can be directly made by the resulting solution of each dye monomer, for example using ionogen (as sodium-chlor or Repone K) from reaction medium dyestuff to be saltoutd leaches, or with mixing solutions evaporation, spraying drying, at this moment, can add the commercialization usual auxiliaries, as Sodium sulfate anhydrous.min(99) (industrial sulphuric acid sodium) etc.
Composite reactive yellow dye of the present invention is suitable for the dyeing and the stamp of filamentary materials such as most of hydroxyl or nitrogenous material, for example silk, leather, timber, tynex and trevira, particularly cellulosic fibre material.Cellulosic fibre material has native cellulose fibre as cotton, flax, fabric, hemp fibre, Mierocrystalline cellulose and regenerated cellulose.Dyestuff of the present invention also is suitable for the dyeing or the stamp of the BLENDED FABRIC of hydroxyl fiber, as mixture cotton and trevira or tynex.Dyestuff of the present invention is particularly suitable for dyeing or the stamp of cellulosic fibre material cotton.
Composite reactive yellow dye of the present invention can use the known utilisation technology of water-soluble dye, particularly fibre-reactive dyes that above fabric is dyeed or stamp.Dyestuff of the present invention has high reaction activity, good fixation ability and well assembles ability.Therefore they can be used for the dip-dye method under low dyeing temperature, and in pad steaming process the required steam time short.Degree of fixation height and non-fixed portions are easy to flush away.
When composite reactive yellow dye of the present invention is used to print and dye, can obtain dye level height, bright in luster, light fastness, fastness to rubbing, dyeing and weaving thing that the moisture-proof fastness is fabulous.
(4) embodiment
The invention will be further described below in conjunction with embodiment, but protection scope of the present invention is not limited to this.Be that form with sodium salt is produced with isolating according to the described compound of structural formula in an embodiment, and be used for dyeing with the form of sodium salt.Each compound can adopt known method synthetic.
Embodiment 1
Dyestuff B, Sodium sulfate anhydrous.min(99) 8 grams of the dyestuff A of 75 gram following formulas (I-1), 25 gram following formulas (II-1) are pieced together mixed, spraying drying makes composite reactive yellow dye.
Formula (I-1)
Formula (II-1)
Embodiment 2
To contain the dyestuff A of 75 gram formulas (I-1) the aqueous solution, contain the aqueous solution of the dyestuff B of 25 gram formulas (II-1), add Sodium sulfate anhydrous.min(99) 8 grams, spraying drying makes composite reactive yellow dye.
Embodiment 3
Dyestuff C, Sodium sulfate anhydrous.min(99) 8 grams of the dyestuff B of the dyestuff A of 85 gram following formulas (I-2), 14 gram following formulas (II-2), 1 gram following formula (III-1) are pieced together mixed, spraying drying makes composite reactive yellow dye.
Embodiment 4
To contain the dyestuff A of 85 gram formulas (I-2) the aqueous solution, contain the dyestuff B of 14 gram formulas (II-2) the aqueous solution, contain the aqueous solution intermingling of dyestuff C of 1 gram following formula (III-1), add Sodium sulfate anhydrous.min(99) 8 grams, spraying drying makes composite reactive yellow dye.
Embodiment 5～22
According to embodiment 1 described colorant match method, the dyestuff A in the following table 1, dyestuff B are mixed in proportion, can obtain to make cellulosic fibre material composite dye with deep yellow.
Table 1
Embodiment 23～27
According to embodiment 3 described colorant match methods, the dyestuff A in the following table 2, dyestuff B, dyestuff C are mixed in proportion, can obtain to make cellulosic fibre material composite dye with deep yellow.
Table 2
Embodiment 28 dye levels are measured
Respectively the compound disperse yellow dye that embodiment 1～27 is made by the coloured differently degree of depth (cloth heavy 0.5%, 1%, 2%, 4%, 6%, 8%) dyeing is after the oven dry, to building up 4 layers, get that identical faces is a plurality of to enter K/S value test interface with Datacolor SF600 Plus-CT color measurement instrument and test, get its mean value (the computer setup parameter: colour examining aperture 30mm, flashing light is once, to color light source D65) as the absolute degree of fixation of this cloth specimen, promptly apparent K/S value.
The dyestuff A of formula (I-1), the dyestuff B of formula (II-1) are done contrast experiment 1,2 respectively.Test result is as shown in table 3.
Table 3
| Dye level | 0.5％ | 1％ | 2％ | 4％ | 6％ | 8％ |
| Embodiment 1 | 3.81 | 7.91 | 14.60 | 26.69 | 30.61 | 32.28 |
| Embodiment 2 | 4.21 | 8.19 | 15.06 | 25.44 | 30.99 | 31.89 |
| Embodiment 3 | 3.78 | 7.90 | 14.78 | 26.64 | 30.89 | 32.14 |
| Embodiment 4 | 4.20 | 8.20 | 15.06 | 25.44 | 30.56 | 31.84 |
| Embodiment 5 | 3.86 | 7.90 | 14.68 | 26.69 | 30.85 | 32.25 |
| Embodiment 6 | 4.12 | 8.10 | 15.06 | 25.74 | 30.75 | 31.75 |
| Embodiment 7 | 3.96 | 7.99 | 14.88 | 2699 | 30.84 | 32.54 |
| Embodiment 8 | 4.03 | 8.14 | 15.06 | 25.44 | 30.75 | 31.41 |
| Embodiment 9 | 3.96 | 7.91 | 14.81 | 26.69 | 30.85 | 32.85 |
| Embodiment 10 | 4.21 | 8.15 | 15.06 | 25.84 | 30.45 | 31.45 |
| Embodiment 11 | 3.85 | 7.93 | 14.62 | 26.79 | 30.85 | 32.14 |
| Embodiment 12 | 4.04 | 8.14 | 15.06 | 25.44 | 30.99 | 31.89 |
| Embodiment 13 | 3.08 | 7.94 | 14.56 | 26.69 | 30.44 | 32.28 |
| Embodiment 14 | 4.32 | 8.15 | 15.06 | 25.64 | 30.99 | 31.44 |
| Embodiment 15 | 3.07 | 7.94 | 14.65 | 26.69 | 30.61 | 32.28 |
| Embodiment 16 | 4.14 | 8.11 | 15.11 | 25.84 | 30.56 | 31.89 |
| Embodiment 17 | 3.94 | 7.95 | 14.60 | 26.69 | 30.85 | 32.28 |
| Embodiment 18 | 4.21 | 8.11 | 15.06 | 25.44 | 30.75 | 31.89 |
| Embodiment 19 | 3.94 | 7.99 | 14.60 | 26.49 | 30.84 | 32.28 |
| Embodiment 20 | 4.01 | 8.11 | 15.06 | 25.42 | 30.75 | 31.89 |
| Embodiment 19 | 3.75 | 7.94 | 14.60 | 26.69 | 30.85 | 32.14 |
| Embodiment 20 | 4.44 | 8.11 | 15.06 | 25.44 | 30.45 | 31.529 |
| Embodiment 21 | 3.89 | 7.91 | 14.60 | 26.64 | 30.61 | 32.28 |
| Embodiment 22 | 4.21 | 8.19 | 15.06 | 25.44 | 30.99 | 31.89 |
| Embodiment 23 | 3.86 | 7.92 | 14.14 | 26.65 | 30.58 | 32.21 |
| Embodiment 24 | 4.12 | 8.10 | 15.04 | 25.24 | 30.94 | 31.44 |
| Embodiment 25 | 3.96 | 7.93 | 14.87 | 26.63 | 30.61 | 32.03 |
| Embodiment 26 | 4.03 | 8.19 | 15.26 | 25.22 | 30.90 | 31.60 |
| Embodiment 27 | 3.96 | 7.94 | 14.45 | 26.11 | 30.74 | 32.21 |
| Comparative Examples 1 | 2.53 | 4.88 | 8.87 | 15.94 | 20.19 | 22.3 |
| Comparative Examples 2 | 2.91 | 6.23 | 12.57 | 21.09 | 25.6 | 28.46 |
Embodiment 29 dyefastness are measured
The reactive dyestuffs that 2 grams are obtained according to embodiment 1～27 are dissolved in the 400 gram water respectively; Add every liter of solution that contains 53g sodium-chlor of 1500 grams.In this dyestuff, add 100 gram cotton fabrics under 40 ℃.After 45 minutes, add every liter of solution that contains 16g sodium hydroxide and the burnt yellow soda ash of 20g of 100 grams.Kept 40 ℃ of meters of this dye liquor again 45 minutes.Then, the flushing product dyed thereby is soaped a quarter in boiling water with nonionic detergent, again flushing and dry.Observe its color, adopt the method for determining among GB/T 3920-1997, GB/T3922-1997 and the GB/T 5713-1997 to test its colour fastness to rubbing, colour fastness to perspiration, color fastness to water.Test result sees Table 4.
The dyestuff A of formula (I-1), the dyestuff B of formula (II-1) are done contrast experiment 1,2 respectively.Test result is as shown in table 4.
Table 4
| Test event | Color | Rub resistance | Perspiration resistance | Color fastness to water | ||
| Unlubricated friction | Wet rubbing | Acid | Alkali | |||
| Embodiment 1 | Deep yellow | 3～4 grades | 2～3 grades | 4～5 grades | 4～5 grades | 4～5 grades |
| Embodiment 2 | Deep yellow | 3～4 grades | 2～3 grades | 4～5 grades | 4～5 grades | 4～5 grades |
| Embodiment 3 | Deep yellow | 3～4 grades | 2～3 grades | 4～5 grades | 4～5 grades | 4～5 grades |
| Embodiment 4 | Deep yellow | 4 grades | 3 grades | 4～5 grades | 4～5 grades | 4～5 grades |
| Embodiment 5 | Deep yellow | 4 grades | 3 grades | 4～5 grades | 4～5 grades | 4～5 grades |
| Embodiment 6 | Deep yellow | 3～4 grades | 2～3 grades | 4～5 grades | 4～5 grades | 4～5 grades |
| Embodiment 7 | Deep yellow | 3～4 grades | 2～3 grades | 4～5 grades | 4～5 grades | 4～5 grades |
| Embodiment 8 | Deep yellow | 3～4 grades | 2～3 grades | 4～5 grades | 4～5 grades | 4～5 grades |
| Embodiment 9 | Deep yellow | 3～4 grades | 2～3 grades | 4～5 grades | 4～5 grades | 4～5 grades |
| Embodiment 10 | Deep yellow | 4 grades | 3 grades | 4～5 grades | 4～5 grades | 4～5 grades |
| Embodiment 11 | Deep yellow | 3～4 grades | 2～3 grades | 4～5 grades | 4～5 grades | 4～5 grades |
| Embodiment 12 | Deep yellow | 4 grades | 3 grades | 4～5 grades | 4～5 grades | 4～5 grades |
| Embodiment 13 | Deep yellow | 4 grades | 3 grades | 4～5 grades | 4～5 grades | 4～5 grades |
| Embodiment 14 | Deep yellow | 3～4 grades | 2～3 grades | 4～5 grades | 4～5 grades | 4～5 grades |
| Embodiment 15 | Deep yellow | 3～4 grades | 2～3 grades | 4～5 grades | 4～5 grades | 4～5 grades |
| Embodiment 16 | Deep yellow | 3～4 grades | 2～3 grades | 4～5 grades | 4～5 grades | 4～5 grades |
| Embodiment 17 | Deep yellow | 4 grades | 3 grades | 4～5 grades | 4～5 grades | 4～5 grades |
| Embodiment 18 | Deep yellow | 4 grades | 3 grades | 4～5 grades | 4～5 grades | 4～5 grades |
| Embodiment 19 | Deep yellow | 4 grades | 3 grades | 4～5 grades | 4～5 grades | 4～5 grades |
| Embodiment 20 | Deep yellow | 4 grades | 3 grades | 4～5 grades | 4～5 grades | 4～5 grades |
| Embodiment 21 | Deep yellow | 3～4 grades | 2～3 grades | 4～5 grades | 4～5 grades | 4～5 grades |
| Embodiment 22 | Deep yellow | 3～4 grades | 2～3 grades | 4～5 grades | 4～5 grades | 4～5 grades |
| Embodiment 23 | Deep yellow | 4 grades | 3 grades | 4～5 grades | 4～5 grades | 4～5 grades |
| Embodiment 24 | Deep yellow | 4 grades | 3 grades | 4～5 grades | 4～5 grades | 4～5 grades |
| Embodiment 25 | Deep yellow | 4 grades | 3 grades | 4～5 grades | 4～5 grades | 4～5 grades |
| Embodiment 26 | Deep yellow | 4 grades | 3 grades | 4～5 grades | 4～5 grades | 4～5 grades |
| Embodiment 27 | Deep yellow | 4 grades | 3 grades | 4～5 grades | 4～5 grades | 4～5 grades |
| Comparative Examples 1 | Yellow | 3～4 grades | 2～3 grades | 4 grades | 4 grades | 4 grades |
| Comparative Examples 2 | Orange | 3 grades | 2～3 grades | 4 grades | 4 grades | 4 grades |
By data shown in the table 4 as can be seen, the composite reactive yellow dye coloured light vividness height, the colour fastness that obtain of the present invention is good.
Claims (10)
1. composite reactive yellow dye, meter by weight, by one or more of 30～99 parts shown in structural formula (I) dyestuff A and one or more dyestuff B shown in structural formula (II) of 1～70 part form;
Its Chinese style (I) and (II) in,
R
1, R
2Independent separately is H, C
1～C
4Alkyl, C
1～C
4Alkoxyl group ,-NHCOR ＇ or-NHCONH
2, R ＇ is C
1～C
4Alkyl;
R
3, R
4, R
6, R
7Independent separately is H, C
1～C
4Alkyl, C
1～C
4Alkoxyl group or sulfonic group;
R
5Be H or C
1～C
4Alkyl;
N is 0～3 integer;
M respectively do for oneself H or alkali metal atom;
X is-CH=CH
2Or-C
2H
4OSO
3M ＇, M ＇ are H or alkali metal atom.
2. composite reactive yellow dye as claimed in claim 1 is characterized in that described R
1Be H, R
2For-NHCONH
2
3. composite reactive yellow dye as claimed in claim 2 is characterized in that described R
3, R
4, R
5, R
6, R
7Independent separately is H.
4. composite reactive yellow dye as claimed in claim 3 is characterized in that described n is 3, and M is Na, and X is-C
2H
4OSO
3Na.
5. as the described composite reactive yellow dye of one of claim 1～4, the parts by weight that it is characterized in that described dyestuff A are 50～90 parts, and the parts by weight of dyestuff B are 5～50 parts.
6. composite reactive yellow dye as claimed in claim 5, the parts by weight that it is characterized in that described dyestuff A are 65～85 parts, the parts by weight of dyestuff B are 10～30 parts.
7. composite reactive yellow dye, meter by weight, by dyestuff A shown in structural formula (I) of one or more of 30～99 parts, one or more of 1～70 part shown in structural formula (II) dyestuff B and one or more dyestuff C shown in structural formula (III) of 0.1～5 part form:
During its Chinese style (I), (II) reach (III),
R
1, R
2Independent separately is H, C
1～C
4Alkyl, C
1～C
4Alkoxyl group ,-NHCOR ＇ or-NHCONH
2, R ＇ is C
1～C
4Alkyl;
R
3, R
4, R
6, R
7Independent separately is H, C
1～C
4Alkyl, C
1～C
4Alkoxyl group or sulfonic group;
R
5Be H or C
1～C
4Alkyl;
R
8Be H, C
1～C
4Alkyl or alkoxyl group;
N is 0～3 integer, and n ＇ is 1～3 integer;
M is H or alkali metal atom;
X, Z independently are-CH=CH separately
2Or-C
2H
4OSO
3M ＇, M ＇ are H or alkali metal atom.
8. composite reactive yellow dye as claimed in claim 7 is characterized in that described R
2For-NHCONH
2, R
1, R
3, R
4, R
5, R
6, R
7, R
8Independent separately is H, and n is 3, and n ＇ is 2, and M is a sodium, and X, Z independently are-C separately
2H
4OSO
3Na.
9. as claim 7 or 8 described composite reactive yellow dyes, the parts by weight that it is characterized in that described dyestuff A are 50～90 parts, and the parts by weight of dyestuff B are 5～50 parts, and the parts by weight of dyestuff C are 0.1～3 part.
10. composite reactive yellow dye as claimed in claim 9, the parts by weight that it is characterized in that described dyestuff A are 65～85 parts, the parts by weight of dyestuff B are 10～30 parts.
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|---|---|---|---|
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|---|---|---|---|
| CNB2006100493714A CN100362055C (en) | 2006-01-26 | 2006-01-26 | Composite reactive yellow dye |
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| CN100362055C true CN100362055C (en) | 2008-01-16 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100528972C (en) * | 2006-08-18 | 2009-08-19 | 浙江龙盛集团股份有限公司 | Composite reactive dye |
| CN101302355B (en) * | 2007-05-08 | 2011-04-06 | 上海雅运纺织化工有限公司 | Yellow reactive dye composition and use thereof |
| CN101440227B (en) * | 2007-11-22 | 2012-10-03 | 上海雅运精细化工有限公司 | Yellow reactive dye composition and use thereof |
| CN102108214B (en) * | 2009-12-25 | 2013-12-18 | 上海安诺其纺织化工股份有限公司 | Active yellow dye compound, preparation method thereof and active yellow dye containing active yellow dye component |
| CN103030990A (en) * | 2011-06-30 | 2013-04-10 | 上海安诺其纺织化工股份有限公司 | Preparation method of azoic compound |
| CN102433030B (en) * | 2011-10-28 | 2013-08-28 | 浙江瑞华化工有限公司 | Active yellow dye composition |
| CN104559320A (en) * | 2014-04-28 | 2015-04-29 | 无锡润新染料有限公司 | Composite active brilliant orange dye composition |
| CN107141264A (en) * | 2017-07-03 | 2017-09-08 | 上海安诺其集团股份有限公司 | A kind of azo compound, its preparation method, intermediate and application |
| CN107141265A (en) * | 2017-07-03 | 2017-09-08 | 上海安诺其集团股份有限公司 | A kind of azo compound, its preparation method, intermediate and application |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW513470B (en) * | 1999-06-04 | 2002-12-11 | Everlight Chem Ind Corp | Reactive dye composition |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW513470B (en) * | 1999-06-04 | 2002-12-11 | Everlight Chem Ind Corp | Reactive dye composition |
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