CN101735649A - Yellow to red composite reactive dye - Google Patents
Yellow to red composite reactive dye Download PDFInfo
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- CN101735649A CN101735649A CN 200910157173 CN200910157173A CN101735649A CN 101735649 A CN101735649 A CN 101735649A CN 200910157173 CN200910157173 CN 200910157173 CN 200910157173 A CN200910157173 A CN 200910157173A CN 101735649 A CN101735649 A CN 101735649A
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- component
- dye
- composite active
- mass content
- dyestuff
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- 239000002131 composite material Substances 0.000 title claims abstract description 43
- 239000000985 reactive dye Substances 0.000 title abstract description 4
- 239000000975 dye Substances 0.000 claims abstract description 113
- 229910052708 sodium Inorganic materials 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 238000004043 dyeing Methods 0.000 abstract description 18
- 150000003839 salts Chemical class 0.000 abstract description 6
- 239000003513 alkali Substances 0.000 abstract description 4
- 230000008901 benefit Effects 0.000 abstract description 2
- 238000000034 method Methods 0.000 description 18
- 239000000243 solution Substances 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 13
- 239000004744 fabric Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- 229920000742 Cotton Polymers 0.000 description 7
- 241000219146 Gossypium Species 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000009833 condensation Methods 0.000 description 6
- 230000005494 condensation Effects 0.000 description 6
- 238000005859 coupling reaction Methods 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000010612 desalination reaction Methods 0.000 description 5
- 239000000835 fiber Substances 0.000 description 5
- 229940056729 sodium sulfate anhydrous Drugs 0.000 description 5
- 239000012752 auxiliary agent Substances 0.000 description 4
- 238000010009 beating Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000012954 diazonium Substances 0.000 description 4
- 238000006193 diazotization reaction Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 230000001105 regulatory effect Effects 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- -1 alkyl naphthalene sulfonic acid formaldehyde Chemical compound 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 230000002708 enhancing effect Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- 229920001732 Lignosulfonate Polymers 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 235000019357 lignosulphonate Nutrition 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- PANBYUAFMMOFOV-UHFFFAOYSA-N sodium;sulfuric acid Chemical compound [Na].OS(O)(=O)=O PANBYUAFMMOFOV-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- KTHUKEZOIFYPEH-UHFFFAOYSA-N 1-benzylnaphthalene Chemical compound C=1C=CC2=CC=CC=C2C=1CC1=CC=CC=C1 KTHUKEZOIFYPEH-UHFFFAOYSA-N 0.000 description 1
- MBDUIEKYVPVZJH-UHFFFAOYSA-N 1-ethylsulfonylethane Chemical compound CCS(=O)(=O)CC MBDUIEKYVPVZJH-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
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 description 1
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 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
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- DPDMMXDBJGCCQC-UHFFFAOYSA-N [Na].[Cl] Chemical compound [Na].[Cl] DPDMMXDBJGCCQC-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- BMJXMAAIWXBKBD-UHFFFAOYSA-N aniline;dihydrochloride Chemical compound Cl.Cl.NC1=CC=CC=C1 BMJXMAAIWXBKBD-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000007796 conventional method Methods 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
- 239000012153 distilled water Substances 0.000 description 1
- WBZKQQHYRPRKNJ-UHFFFAOYSA-L disulfite Chemical compound [O-]S(=O)S([O-])(=O)=O WBZKQQHYRPRKNJ-UHFFFAOYSA-L 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect 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
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 229960004249 sodium acetate Drugs 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 159000000000 sodium salts Chemical group 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
- QPILZZVXGUNELN-UHFFFAOYSA-M sodium;4-amino-5-hydroxynaphthalene-2,7-disulfonate;hydron Chemical compound [Na+].OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S([O-])(=O)=O)=CC2=C1 QPILZZVXGUNELN-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
Landscapes
- Coloring (AREA)
Abstract
The invention provides a yellow to red composite reactive dye, which mainly contains one or more components A shown in a structural formula (I), one or more components B shown in a structural formula (II), also can contain one or more components C shown in a structural formula (III) and/or one or more components D shown in a structural formula (IV). The yellow to red composite reactive dye of the invention has the advantages of excellent lifting power, good compatibility, bright color, high fixation rate, high solubility, good salt and alkali tolerance, good color fastness and the like, and is an ideal selection for dye factories to reduce the cost and increase the one-off dyeing success rate.
Description
(1) technical field
The present invention relates to a kind of composite active dye.Particularly be applicable to yellow to red composite active dyes nitrogenous and hydroxyl filamentary material such as cellulosic fibre material printing and dyeing.
(2) background technology
Reactive dyestuffs have lovely luster, with low cost, distinguishing feature such as application is easy, adaptability is strong.But 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.As everyone knows, the reactive dyestuffs of fabric being dyed yellow or redness have a lot, dyestuff described in patent CN101440227, CN1511887, US5308362 and US6168636, but most composite dyestuff still can not satisfy the demands fully at aspects such as lifting force, compatibleness, solubleness, degree of fixation and fastness abilities at present, as the reactive dye color fixing rate have only about 70%, the dyestuff of set does not enter waste water and forms a large amount of coloured sewage, and colorant dissolubility is no more than 250g/l during room temperature.
(3) summary of the invention
For further satisfying the dyeing demand, obtain dark heavy colour pool, the invention provides a kind of yellow to red composite active dye, it is bright-coloured to have coloured light, and compatibleness and enhancing are good, degree of fixation and solubleness height, the salt tolerant alkali resistance is strong, characteristics such as dyefastness excellent performance.
A kind of composite active dye of yellow to red contains the B component shown in the component A shown in one or more formulas (I) and one or more formulas (II), and based on described component A and B component, component A mass content is 1～99%; The B component mass content is 1～99%;
Among formula (I), (II):
R
1Be amino or C
1～C
4Alkyl; R
2, R
3Independent separately is H, SO
3M
3, C
1～C
4Alkyl or C
1～C
4Alkoxyl group; Y
1, Y
2, Y
3Independently be-CH=CH separately
2Or-C
2H
4OSO
3M
4Hal is a halogen; M
1～M
4Separate is H, Na or K.
Among formula (I), (II): R
1Be preferably amino or methyl; R
2, R
3Independently be preferably H, SO separately
3M
3, CH
3Or OCH
3Hal is preferably Cl or F.
Also can contain the component C shown in one or more formulas (III) in the described composite active dye; Based on described component A, B component and component C, component A mass content is 1～96%; The B component mass content is 1～96%, and component C mass content is 1～96%;
In the formula (III):
X
1Be halogen, be preferably Cl or F; Y
4For-CH=CH
2Or-C
2H
4OSO
3M
7M
5Be H, Na or K.
Also can contain the component D shown in one or more formulas (IV) in the described composite active dye; Based on described component A, B component and component D, component A mass content is 1～96%; The B component mass content is 1～96%, and component D mass content is 1～96%; Based on described component A, B component, component C and component D, component A mass content is 1～96%; The B component mass content is 1～96%, and component C mass content is 1～96%, and component D mass content is 1～96%;
In the formula (IV):
Y
5, Y
6Independently be-CH=CH separately
2Or-C
2H
4OSO
3M
7R
4～R
6Independently be-H, C separately
1～C
4Alkyl, C
1～C
4Alkoxyl group or-SO
3M
8, preferred-H or SO
3M
8M
6～M
8Independent separately is H, Na or K.
Described component A is preferably one of following or wherein two or more mixing:
Described B component is preferably one of following or wherein two or more mixing:
Described component C is preferably one of following or wherein two or more mixing:
Described component C is preferably one of following or wherein two or more mixing:
Above-claimed cpd represents with the sour form of freedom that all in actual production, described compound generally is with the form preparation of its salt and isolating, and is used for dyeing with the form of its salt, and preferred form is sodium salt or sylvite.
Composite active dye of the present invention can prepare with ordinary method, for example generally uses each single dye component of mechanically mixing.This single dye component can powdery, the aqueous solution form of granular, resulting solution or each dyestuff exists.Single dye component A, B, C, D can synthesize by mode well known to those skilled in the art easily, according to publication CN1569965B, CN1861695B, the described method of CN1569967B, CN101250333A or similarly method preparation, also can adopt the commercial goods as respectively.
Above-mentioned diazotization, the couling process preparation of respectively organizing dye monomer can be conventional.Can concentrate by the membrane sepn desalination in case of necessity, to make the dye monomer of high density.
When being applied to dye, described composite active dye generally need add reactive dyestuffs auxiliary agent commonly used 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 naphthalene sulfonic 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.
Composite active dye component of the present invention, mainly contain one or more structures suc as formula the component A shown in (I) and one or more structures suc as formula the B component shown in (II), also can comprise one or more structures suc as formula the component C shown in (III) and/or one or more structures suc as formula the component D shown in (IV).In addition, can also contain auxiliary agent and partial impurities, because dyestuff in routine is synthetic, have add earlier acid, after the process that adds alkali or saltout, therefore the dyestuff that is synthesized generally speaking unavoidably can be with ionogen, electrolytic salt as described can be sodium sulfate, sodium-chlor and sodium-acetate, and the existence of these materials does not influence technique effect of the present invention.
Composite active dye of the present invention can be made the liquid dye product as required, also can be with the spray-dried solid phase prod that makes of liquid dye product, perhaps directly mix getting according to the solid dye powder of each component.
Composite active dye of the present invention because of containing cyanuro, ethyl sulfuryl isoreactivity base in its component, makes this composite dye have following superiority: the one, and the solubleness height; The 2nd, the degree of fixation height is because the synergistic effect between a plurality of active groups of this composite dye increases dyestuff and fiber key bonded probability, the utilization ratio of dyestuff improves, the reactive enhancing, and dye stability is good, and this dye strength height, solubleness height have effectively guaranteed painted enhancing; The 3rd, dyefastness is good, and the acid resistance of ethyl sulfone and the alkali resistance of s-triazine and painted high colour-fast rate make this dyestuff acid and alkali-resistance good stability, and hydrolised dye is few; The 4th, environmental protection does not contain carcinogenic arylamine component, alternative most of import dyestuff.
Composite active dye of the present invention be applicable to conventional contaminate, knot dyeing technology is to the printing and dyeing of textile material such as cellulosic fibre, cotton fibre, synthon etc.Composite active dye of the present invention is mixed when piecing together by dye component A and dye component B can dye fabric the Yellow-to-orange tone.In addition, dye component A and dye component B can also be composite with dye component C and/or dye component D, fabric can be dyed yellow to red tone.Composite active dye of the present invention, lifting force excellence, advantage such as compatibleness is good, coloured light is bright-coloured, degree of fixation is high, solubleness is high, the salt tolerant alkaline resistance properties is good, colour fastness is good are that dye-works reduces cost, improves the ideal that once is coloured to power and selects.
(4) embodiment
The present invention is described further below in conjunction with specific embodiment, but protection scope of the present invention is not limited in this:
Embodiment 1:
Formula (I-1) structure dyestuff A's is synthetic:
0.1mol 3,6, after 8-trisulfonic acid-2-naphthylamines making beating evenly, with icing holding temperature at 5～8 ℃, add hydrochloric acid, sodium nitrite solution carries out diazotization reaction, finish the back in the diazonium thing adding 0.1mol between urea amido anilinechloride hydrochloride at 5～10 ℃, carry out coupled reaction under the condition of pH4～6, the coupling terminal point is to carrying out primary condensation with the cyanuric chloride of 0.1mol at 0～5 ℃ again, keep 0～15 ℃ of temperature, pH4～6, what add 0.1mol after reaction is finished carries out the secondary condensation to (beta-sulfuric ester ethyl sulfonyl) aniline, 40～60 ℃ of controlled temperature, PH5～7, dye solution desalination after reaction finishes is also dry, promptly gets the dyestuff A of following formula (I-1) structure.
The dyestuff of its residue (I) can be with reference to above-mentioned similar method preparation among the present invention.
Formula (II-2) structure dyestuff B's is synthetic:
0.2mol is evenly added hydrochloric acid and cools to 5 ℃ with ice in the back the making beating of (beta-sulfuric ester ethyl sulfonyl) aniline, add sodium nitrite solution diazotization reaction under agitation, finish the back and in the diazonium thing, add 2 of 0.1mol, the 4-diamino benzene sulfonic acid, holding temperature 6-8 ℃, the PH3-4 coupled reaction, the dye solution desalination after reaction finishes is also dry, promptly gets the dyestuff B of following formula (II-2) structure.
The dyestuff of its residue (II) can be with reference to above-mentioned similar method preparation among the present invention.
The preparation of composite active dye:
Dyestuff A, the dyestuff B of 5g formula (II-2), the 50g Sodium sulfate anhydrous.min(99) of the formula (I-1) that 95g is made, the water that adds 400g mixes, regulating the dye liquor pH value is 5.5～6.5, dry this dye solution, make described composite active dye, according to reactive dyestuffs normal dyeing method, can on cotton fabric, obtain the dyeing and the stamp of yellow tone.
Embodiment 2:
With the dyestuff A of 90 parts of formulas (I-1), the dyestuff B of 10 parts of formulas (II-1), 45 parts of Sodium sulfate anhydrous.min(99), the water that adds 350 parts mixes, regulating the dye liquor pH value is 5.5-6.5, dry this dye solution, make described composite active dye, according to reactive dyestuffs normal dyeing method, can on cotton fabric, obtain the dyeing and the stamp of yellow tone.
Embodiment 3:
Formula (III-1) structure dyestuff C's is synthetic:
Cyanuric chloride and the dispersion agent making beating in the presence of ice of 0.1mol is even, add 0.1mol to (beta-sulfuric ester ethyl sulfonyl) aniline primary condensation, control pH2～3,6～12 ℃ of temperature, add 1 part of H acid again after reaction is finished and carry out the secondary condensation, control pH3～5,25～35 ℃ of temperature, reaction finishes to cool to 20～30 ℃, last with 1,5-disulfonic acid-2-naphthylamines diazonium salt carries out coupling, and the dye solution desalination after coupling finishes is also dry, promptly gets the dyestuff C of following formula (III-1) structure.
The dyestuff of its residue (III) can be with reference to above-mentioned similar method preparation among the present invention.
Formula (IV-4) structure dyestuff D's is synthetic:
0.2mol is evenly added hydrochloric acid and cools to 5 ℃ with ice in the back the making beating of (beta-sulfuric ester ethyl sulfonyl) aniline, add sodium nitrite solution diazotization reaction under agitation, finish the J acid of back adding 0.1mol in the diazonium thing, 10～25 ℃ of holding temperatures, PH2～5 coupled reactions, dye solution desalination after reaction finishes is also dry, promptly gets the dyestuff D of following formula (IV-4) structure.
The dyestuff of its residue (IV) can be with reference to above-mentioned similar method preparation among the present invention.
The preparation of composite active dye:
Dyestuff A, the dyestuff B of 5 parts of formulas (II-2), the dyestuff C of 85 parts of formulas (III-1), the dyestuff D of 5 parts of formulas (IV-4), 35 parts of Sodium sulfate anhydrous.min(99) with 5 parts of formulas (I-1), the water that adds 500 parts mixes, regulating dye liquor pH value is 5.5～6.5, dry this dye solution, make described composite active dye, according to reactive dyestuffs normal dyeing method, can on cotton fabric, obtain the dyeing and the stamp of red tone.
Embodiment 4:
Dyestuff A, the dyestuff B of 10 parts of formulas (II-1), the dyestuff C of 70 parts of formulas (III-1), the dyestuff D of 10 parts of formulas (IV-1), 50 parts of Sodium sulfate anhydrous.min(99) with 10 parts of formulas (I-1), the water that adds 500 parts mixes, regulating dye liquor pH value is 5.5～6.5, dry this dye solution, make described composite active dye, according to reactive dyestuffs normal dyeing method, can on cotton fabric, obtain the dyeing and the stamp of red tone.
Embodiment 5～11:
The composite dye preparation is with reference to the preparation method of embodiment 4, each dye monomer preparation method is with reference to the method for embodiment 1 or 3, different is, the compound structure and the proportioning that change dyestuff A, B, C, D see Table 1, prepare composite active dye of the present invention, with reactive dyestuffs normal dyeing method, cotton fabric can be dyed yellow to red tone.
Table 1
Embodiment 12: performance test
1, the mensuration of dyefastness:
Respectively get the composite active dye of 0.5 gram embodiment, 1～11 preparation, place the 250ml volumetric flask to be made into uniform solution.Draw 20 milliliters then and in dye vat, mix, and add the metabisulfite solution of 50ml 20%, make dye liquor with 120ml distilled water.2 gram cottons are immersed in this dye liquor, under normal temperature and pressure, be heated to 60 ℃, suction was dyed 30 minutes, the sodium carbonate solution that adds 10ml 20% afterwards is in dye vat, fabric is carried out fixation, 60 ℃ dyed in the model machine fixation 45 minutes, dye to finish and take out, fully washing and strand are done, in the soap lye that contains soap flakes 3 grams per liters, boil and boil 15 minutes, clean strand and do, 60 ℃～70 ℃ down dry samplings, adopt ISO105 * 12-1993 respectively, ISO105-CO3-1989, ISO105-E03-1987, the method of determining among the ISO105-E04-1989 is tested its crock fastness, washing fastness, fastness to chlorinated water and fastness to perspiration, test result sees Table 2:
Table 2
2, the mensuration of other dyeing behavioies:
Record the degree of fixation under the different fixation time conditions according to a conventional method, see the following form 3:
Table 3
Reactive dyestuffs of the present invention repeat repeatedly to dye and can both obtain solubleness height, degree of fixation height, colour fastness is good, dyeing behavior is stable yellow to red dyeing and weaving thing.
Claims (9)
1. the composite active dye of a yellow to red contains the B component shown in the component A shown in one or more formulas (I) and one or more formulas (II), and based on described component A and B component, component A mass content is 1～99%; The B component mass content is 1～99%;
Among formula (I), (II):
R
1Be amino or C
1～C
4Alkyl; R
2, R
3Independent separately is H, SO
3M
3, C
1～C
4Alkyl or C
1～C
4Alkoxyl group; Y
1, Y
2, Y
3Independently be-CH=CH separately
2Or-C
2H
4OSO
3M
4Hal is a halogen; M
1～M
4Separate is H, Na or K.
2. composite active dye as claimed in claim 1 is characterized in that: among formula (I), (II): R
1Be amino or methyl; R
2, R
3Independent separately is H, SO
3M
3, CH
3Or OCH
3Hal is Cl or F.
3. composite active dye as claimed in claim 1 is characterized in that: also contain the component C shown in one or more formulas (III) in the described composite active dye; Based on described component A, B component and component C, component A mass content is 1～96%; The B component mass content is 1～96%, and component C mass content is 1～96%;
In the formula (III):
X
1Be halogen; Y
4For-CH=CH
2Or-C
2H
4OSO
3M
7M
5Be H, Na or K.
4. composite active dye as claimed in claim 1 is characterized in that: also contain the component D shown in one or more formulas (IV) in the described composite active dye; Based on described component A, B component and component D, component A mass content is 1～96%; The B component mass content is 1～96%, and component D mass content is 1～96%;
In the formula (IV):
Y
5, Y
6Independently be-CH=CH separately
2Or-C
2H
4OSO
3M
7R
4～R
6Independently be-H, C separately
1～C
4Alkyl, C
1～C
4Alkoxyl group or-SO
3M
8M
6～M
8Independent separately is H, Na or K.
5. composite active dye as claimed in claim 3 is characterized in that: contain the component D shown in one or more multiple formulas (IV) in the described composite active dye; Based on described component A, B component, component C and component D, component A mass content is 1～96%; The B component mass content is 1～96%, and component C mass content is 1～96%, and component D mass content is 1～96%;
In the formula (IV):
Y
5, Y
6Independently be-CH=CH separately
2Or-C
2H
4OSO
3M
7R
4～R
6Independently be-H, C separately
1～C
4Alkyl, C
1～C
4Alkoxyl group or-SO
3M
8M
6～M
8Independent separately is H, Na or K.
6. as the described composite active dye of one of claim 1～5, it is characterized in that described component A is one of following or wherein two or more mixing:
7. as the described composite active dye of one of claim 1～5, it is characterized in that described B component is one of following or wherein two or more mixing:
8. as claim 3 or 5 described composite active dyes, it is characterized in that described component C is one of following or wherein two or more mixing:
9. as claim 4 or 5 described composite active dyes, it is characterized in that described component C is one of following or wherein two or more mixing:
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2009101571733A CN101735649B (en) | 2009-12-23 | 2009-12-23 | Yellow to red composite reactive dye |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2009101571733A CN101735649B (en) | 2009-12-23 | 2009-12-23 | Yellow to red composite reactive dye |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101735649A true CN101735649A (en) | 2010-06-16 |
| CN101735649B CN101735649B (en) | 2013-04-24 |
Family
ID=42459693
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2009101571733A Expired - Fee Related CN101735649B (en) | 2009-12-23 | 2009-12-23 | Yellow to red composite reactive dye |
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| Country | Link |
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| CN (1) | CN101735649B (en) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102031018A (en) * | 2010-11-19 | 2011-04-27 | 无锡润新染料有限公司 | Composite reactive grey for printing and dyeing and clean production process thereof |
| CN102268193A (en) * | 2011-06-29 | 2011-12-07 | 天津德凯化工股份有限公司 | Yellow active dye for furs and preparation method thereof |
| CN104119691A (en) * | 2013-04-28 | 2014-10-29 | 浙江龙盛集团股份有限公司 | Orange red reactive dye compound and application thereof |
| CN104479402A (en) * | 2014-12-11 | 2015-04-01 | 吴江桃源染料有限公司 | Semi-finished product of deep red dye, preparation method and application thereof |
| CN105062140A (en) * | 2015-09-02 | 2015-11-18 | 湖北华丽染料工业有限公司 | Composite reactive deep yellow dye as well as preparation method and application thereof |
| CN105778560A (en) * | 2016-03-17 | 2016-07-20 | 浙江瑞华化工有限公司 | Red active dye composition and preparation method and use thereof |
| CN106433215A (en) * | 2016-10-12 | 2017-02-22 | 上海雅运纺织化工股份有限公司 | Red dye composition, and dyeing application and method thereof to fiber |
| CN106700651A (en) * | 2016-12-30 | 2017-05-24 | 江苏安诺其化工有限公司 | Preparation method of yellow dye |
| CN106854384A (en) * | 2016-12-30 | 2017-06-16 | 江苏安诺其化工有限公司 | A kind of weld, dye material composition and application |
| CN107337936A (en) * | 2017-07-03 | 2017-11-10 | 上海安诺其集团股份有限公司 | A kind of dyestuff, dye material composition and dye material composition and application |
| CN109705616A (en) * | 2018-12-24 | 2019-05-03 | 浙江龙盛化工研究有限公司 | A kind of active red dye composition |
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2009
- 2009-12-23 CN CN2009101571733A patent/CN101735649B/en not_active Expired - Fee Related
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102031018A (en) * | 2010-11-19 | 2011-04-27 | 无锡润新染料有限公司 | Composite reactive grey for printing and dyeing and clean production process thereof |
| CN102268193A (en) * | 2011-06-29 | 2011-12-07 | 天津德凯化工股份有限公司 | Yellow active dye for furs and preparation method thereof |
| CN104119691A (en) * | 2013-04-28 | 2014-10-29 | 浙江龙盛集团股份有限公司 | Orange red reactive dye compound and application thereof |
| CN104479402A (en) * | 2014-12-11 | 2015-04-01 | 吴江桃源染料有限公司 | Semi-finished product of deep red dye, preparation method and application thereof |
| CN105062140A (en) * | 2015-09-02 | 2015-11-18 | 湖北华丽染料工业有限公司 | Composite reactive deep yellow dye as well as preparation method and application thereof |
| CN105778560B (en) * | 2016-03-17 | 2017-08-08 | 浙江瑞华化工有限公司 | A kind of red reactive dye composition and its production and use |
| CN105778560A (en) * | 2016-03-17 | 2016-07-20 | 浙江瑞华化工有限公司 | Red active dye composition and preparation method and use thereof |
| CN106433215A (en) * | 2016-10-12 | 2017-02-22 | 上海雅运纺织化工股份有限公司 | Red dye composition, and dyeing application and method thereof to fiber |
| CN106433215B (en) * | 2016-10-12 | 2018-03-02 | 上海雅运纺织化工股份有限公司 | Red dye composition and its tint applications and method on fiber |
| CN106700651A (en) * | 2016-12-30 | 2017-05-24 | 江苏安诺其化工有限公司 | Preparation method of yellow dye |
| CN106854384A (en) * | 2016-12-30 | 2017-06-16 | 江苏安诺其化工有限公司 | A kind of weld, dye material composition and application |
| CN107337936A (en) * | 2017-07-03 | 2017-11-10 | 上海安诺其集团股份有限公司 | A kind of dyestuff, dye material composition and dye material composition and application |
| CN109705616A (en) * | 2018-12-24 | 2019-05-03 | 浙江龙盛化工研究有限公司 | A kind of active red dye composition |
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| CN101735649B (en) | 2013-04-24 |
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