CN1995153A - Composite reactive dye - Google Patents
Composite reactive dye Download PDFInfo
- Publication number
- CN1995153A CN1995153A CN 200610053017 CN200610053017A CN1995153A CN 1995153 A CN1995153 A CN 1995153A CN 200610053017 CN200610053017 CN 200610053017 CN 200610053017 A CN200610053017 A CN 200610053017A CN 1995153 A CN1995153 A CN 1995153A
- Authority
- CN
- China
- Prior art keywords
- dyestuff
- dyes
- formula
- dye
- composite active
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000002131 composite material Substances 0.000 title claims abstract description 20
- 239000000985 reactive dye Substances 0.000 title abstract description 6
- 239000000975 dye Substances 0.000 claims abstract description 71
- 150000001875 compounds Chemical class 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000000835 fiber Substances 0.000 abstract description 10
- 238000000034 method Methods 0.000 abstract description 9
- 239000004744 fabric Substances 0.000 abstract description 8
- 238000006243 chemical reaction Methods 0.000 abstract description 6
- 238000005406 washing Methods 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 12
- 238000004043 dyeing Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 229920000742 Cotton Polymers 0.000 description 7
- 239000007788 liquid Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 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
- 238000001035 drying Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229940056729 sodium sulfate anhydrous Drugs 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229920004935 Trevira® Polymers 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000012752 auxiliary agent Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000010612 desalination reaction Methods 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000011010 flushing procedure Methods 0.000 description 2
- 230000002650 habitual effect Effects 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000003672 processing method Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- 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
- 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
- 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
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical group 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000010009 beating Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- -1 for example silk Substances 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 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
- PANBYUAFMMOFOV-UHFFFAOYSA-N sodium;sulfuric acid Chemical compound [Na].OS(O)(=O)=O PANBYUAFMMOFOV-UHFFFAOYSA-N 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
Landscapes
- Coloring (AREA)
Abstract
The composite reactive dye basically comprises 1-99 wt% of one or more dyes A shown as a formula and one or more dyes B shown as a formula (II), wherein the weight percentage of the dyes A and the dyes B is based on the total amount of the dyes A and the dyes B. The composite reactive dye has high reaction activity, good color fixing capability and good dye uptake. The above fiber fabrics can be dyed or printed by known application techniques of water-soluble dyes, particularly fiber reactive dyes, to obtain dyed fabrics excellent in vivid yellow to orange tones, light fastness, rubbing fastness and washing fastness.
Description
(1) technical field
The present invention relates to a kind of composite active dye, relate in particular to the composite active dye that a kind of configuration 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.As everyone knows, fabric is dyed yellow extremely orange reactive dyestuffs to be had a lot, dyestuff described in patent JP56-103249, US4841031, CN1103416 and US2004024189, but still can not satisfy the demands fully at aspects such as lifting force, depth and fastness abilities.
(3) summary of the invention
For further satisfying the dyeing demand, the invention provides a kind of middle deep colour dyeing, light fastness excellence, dye uptake and degree of fixation height, washing fastness and crock fastness are good, coloured light is bright-coloured composite active dye of being suitable for.
The technical solution adopted for the present invention to solve the technical problems is: a kind of composite active dye, basically by weight percentage be 1～99% one or more suc as formula the dyestuff A shown in (I), and one or more form suc as formula the dyestuff B shown in (II), and the weight percentage of dyestuff A, dyestuff B is all based on the total amount of dyestuff A, dyestuff B:
In formula (I), the formula (II): R be H or-SO
3M, R
1For-NH
2Or-CH
3Hal is Cl or F; R
2For H or-CH
2CH
2OH; Y
1For-CH=CH
2Or-CH
2CH
2OSO
3M; X is H or SO
3M; R
3, R
4, R
5, R
6Independent separately be H ,-CH
2CH
2OH, SO
3M, C
1～C
4Alkyl or alkoxyl group; Y
2For-CH
2CH
2OSO
3M; Wherein: M is H or alkali metal atom, is preferably H or Na.
Dyestuff A shown in the formula (I) is preferably one or more in the following compounds:
Dyestuff B shown in the formula (II) is preferably one or more in the following compounds:
Composite active dye of the present invention can prepare with ordinary method, for example generally uses single dyestuff A of mechanically mixing and B.This single dyestuff can powdery, the aqueous solution form of granular, resulting solution or each dyestuff exists, and wherein can add auxiliary agent commonly used, as Sodium sulfate anhydrous.min(99) etc.Single dyestuff A, B can describe it respectively as patent CN1103416, patent JP56-103249 with known method preparation.
The preparation that composite active 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 habitual.
When single dyestuff A, B are mixed with the form assembly of resulting solution, separating composite active dye of the present invention from resulting solution can carry out with general known method, 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 active 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, cellulosic fibre material especially.Cellulosic fibre material if any native cellulose fibre as cotton, flax, fabric, hemp fibre, Mierocrystalline cellulose and regenerated cellulose.Composite active dye 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 active dye of the present invention has high reaction activity, good fixation ability and dye uptake.Can dye or stamp to above fabric by the known utilisation technology of water-soluble dye, particularly fibre-reactive dyes, obtain bright Huang to hues of orange, sun-resistant fastness, fastness to rubbing, the fabulous dyeing and weaving thing of washing fastness.
(4) embodiment
Below in conjunction with specific embodiment the present invention is further described, but protection scope of the present invention is not limited to this.
Generally be with the form of its salt preparation and isolating according to the described compound of structural formula in an embodiment, preferred form is sodium salt or sylvite, and is used for dyeing with the form of its salt.Compound described in the embodiment can adopt known method, is synthesized with the form of free acid or the form of its salt similarly.Except as otherwise noted, following " part " is folding hundred weight parts.
Embodiment 1
Synthesizing of formula (I-1) dyestuff
At 61.1 parts of 7-(4-amino-2-urea groups-phenyl diazonium) naphthalene-1,3, the 6-trisulfonic acid receive and 400 parts of ice/water mixture in, adds 18.8 parts of cyanuric chlorides and pulled an oar 2 hours, 0～10 ℃ of controlled temperature, PH are less than 3, the hydrochloric acid of generation neutralizes by adding sodium bicarbonate.Drip in the above-mentioned reaction soln 18.8 parts of dissolvings good 2, the solution of 4-diamino benzene sulfonic acid and 150 parts of water is controlled PH5～7.5, the solution that generates is warming up to 32 ℃, and insulated and stirred 1.5 hours is surveyed terminal point with the TLC chromatography, terminal point to after be that coupling component cools to 15 ℃ with Generation Liquid, standby.
30.3 part para-ester, promptly to (beta-sulfuric ester ethyl sulfonyl) aniline approach diazotization routinely in 150 portions of frozen water, in about 1.5 hours, this diazonium salt solution is added drop-wise to and carries out coupled reaction in the above-mentioned coupling component, 1～10 ℃ of controlled temperature, PH4～7, stirring reaction 3 hours.The dye solution desalination that generates is also dry, and what promptly get following formula (I-1) can dye cotton fibre flavous dyestuff.
Embodiment 2
Synthesizing of formula (II-1) dyestuff
18.9 parts of cyanuric chlorides are placed 122 parts of frozen water making beating 1 hour, in 0.5 hour, drip the 30.3 parts of good para-esters of dissolving and the solution of 145 portions of frozen water, stirring reaction 3 hours, 1～10 ℃ of controlled temperature, pH value 1～4 makes primary condensation liquid.Contracting to above-mentioned one slowly adds 26.1 parts of J acid in the liquid, control pH value about 4.5, and 5～40 ℃ of temperature, stirring reaction 2.5 hours makes two liquid that contract.
With 34.7 parts of 2-naphthylamines-1,5-sodium disulfonate stirring to pulp 1 hour in 315 portions of frozen water carries out diazotization according to a conventional method.Add the liquid that contracts of above-mentioned two below 20 ℃ in this diazonium salt, control PH6～7.5 are stirred down and were carried out coupled reaction 4 hours, and be warming up to afterwards about 30 ℃ and be incubated 1.5 hours, the desalination drying, what promptly get following formula (II-1) can dye cotton fibre orange dyestuff.
Embodiment 3
With dyestuff B, the Sodium sulfate anhydrous.min(99) 8g of the dyestuff A of 86g formula (I-1), 14g formula (II-1) add water piece together mix after, grind with shredder and to disperse, spraying drying promptly gets composite active dye finished product of the present invention.
Embodiment 4
Dyeing procedure
2 parts of reactive dyestuffs that obtain according to embodiment 3 are dissolved in 400 parts of water; Add 1500 parts every liter solution that contains 53g sodium-chlor.In this dyestuff, add 100 parts of cotton fabrics under 40 ℃.After 45 minutes, add 100 parts every liter solution that contains 16g sodium hydroxide and the burnt yellow soda ash of 20g.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.Can obtain bright-coloured yellow cotton, colourability is good, the colour fastness excellence.
Embodiment 5～22
Press embodiment 1 described processing method, change feed composition, the compound of dyestuff A in the preparation following table 1; Press embodiment 2 described processing methodes, change feed composition, the compound of dyestuff B in the preparation following table 1; Press the assembly mixing method described in the embodiment 3, dyestuff A, B in the table 1 are mixed in proportion; By the dyeing process described in the embodiment 4 fabric is dyeed, the results are shown in Table 1.
Table 1
Claims (4)
1. composite active dye, basically by weight percentage be 1～99% one or more suc as formula the dyestuff A shown in (I), and one or more form suc as formula the dyestuff B shown in (II), and the weight percentage of dyestuff A, dyestuff B is all based on the total amount of dyestuff A, dyestuff B:
In formula (I), the formula (II): R be H or-SO
3M,
R
1For-NH
2Or-CH
3, Hal is Cl or F,
R
2For H or-CH
2CH
2OH,
Y
1For-CH=CH
2Or-CH
2CH
2OSO
3M,
X is H or SO
3M,
M is H or Na,
R
3, R
4, R
5, R
6Independent separately be H ,-CH
2CH
2OH, SO
3M, C
1～C
4Alkyl or alkoxyl group, Y
2For-CH
2CH
2OSO
3H or-CH
2CH
2OSO
3Na or-CH
2CH
2Cl.
2. composite active dye as claimed in claim 1 is characterized in that: the dyestuff A shown in the formula (I) is selected from one or more in the following compounds:
3. composite active dye as claimed in claim 1 or 2 is characterized in that: the dyestuff B shown in the formula (II) is selected from one or more in the following compounds:
4. as claim 2 or 3 described composite active dyes, it is characterized in that: described composite active dye mixture is that dyestuff A, one or more weight percentage of 1～99% are that 1～99% dyestuff B forms by one or more weight percentage.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2006100530179A CN100528972C (en) | 2006-08-18 | 2006-08-18 | Composite reactive dye |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2006100530179A CN100528972C (en) | 2006-08-18 | 2006-08-18 | Composite reactive dye |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1995153A true CN1995153A (en) | 2007-07-11 |
| CN100528972C CN100528972C (en) | 2009-08-19 |
Family
ID=38250361
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2006100530179A Expired - Fee Related CN100528972C (en) | 2006-08-18 | 2006-08-18 | Composite reactive dye |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN100528972C (en) |
Cited By (8)
| 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 |
| CN102433030A (en) * | 2011-10-28 | 2012-05-02 | 浙江瑞华化工有限公司 | Active yellow dye composition |
| 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 |
| CN101555361B (en) * | 2009-05-06 | 2013-01-30 | 上海科华染料工业有限公司 | Active red dye composition |
| CN101555360B (en) * | 2009-05-06 | 2013-04-24 | 上海科华染料工业有限公司 | Active tricolor dye composition |
| CN103965653A (en) * | 2014-05-12 | 2014-08-06 | 浙江亿得化工有限公司 | Post-mercerized composite activated dye as well as dyeing method and use thereof |
| CN104479404A (en) * | 2014-12-11 | 2015-04-01 | 吴江桃源染料有限公司 | Environment-friendly reactive yellow disazo dye and preparation method thereof |
| CN107974103A (en) * | 2017-12-04 | 2018-05-01 | 湖北华丽染料工业有限公司 | A kind of composite reactive yellow dye |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5980590A (en) * | 1995-12-28 | 1999-11-09 | Dystar Texilfarben Gmbh & Co. Deutschland Kg | Dyestuff mixtures of water-soluble fiber-reactive azo dyestuffs, processes for their preparation and their use |
| US6015439A (en) * | 1999-02-16 | 2000-01-18 | Dystar Textilefarben Gmbh & Co. | Deep black dye mixtures of fiber-reactive azo dyes and a process for dyeing hydroxy and/or carboxamido containing fibers |
| DE60002693T2 (en) * | 1999-03-30 | 2004-04-15 | Avecia Ltd., Blackley | DYE COMPOSITION WITH HIGH LIGHT FASTNESS |
| GB0006029D0 (en) * | 2000-03-14 | 2000-05-03 | Clariant Int Ltd | Organic compounds |
| JP2004536202A (en) * | 2001-07-20 | 2004-12-02 | チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド | Dyes incorporating anionic and cationic groups |
| CN100362055C (en) * | 2006-01-26 | 2008-01-16 | 浙江龙盛集团股份有限公司 | Composite reactive yellow dye |
-
2006
- 2006-08-18 CN CNB2006100530179A patent/CN100528972C/en not_active Expired - Fee Related
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN101555361B (en) * | 2009-05-06 | 2013-01-30 | 上海科华染料工业有限公司 | Active red dye composition |
| CN101555360B (en) * | 2009-05-06 | 2013-04-24 | 上海科华染料工业有限公司 | Active tricolor dye composition |
| 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 |
| CN102433030A (en) * | 2011-10-28 | 2012-05-02 | 浙江瑞华化工有限公司 | Active yellow dye composition |
| CN102433030B (en) * | 2011-10-28 | 2013-08-28 | 浙江瑞华化工有限公司 | Active yellow dye composition |
| CN103965653A (en) * | 2014-05-12 | 2014-08-06 | 浙江亿得化工有限公司 | Post-mercerized composite activated dye as well as dyeing method and use thereof |
| CN104479404A (en) * | 2014-12-11 | 2015-04-01 | 吴江桃源染料有限公司 | Environment-friendly reactive yellow disazo dye and preparation method thereof |
| CN104479404B (en) * | 2014-12-11 | 2016-09-28 | 吴江桃源染料有限公司 | A kind of preparation method of environment-friendly type active yellow bisazo dye |
| CN107974103A (en) * | 2017-12-04 | 2018-05-01 | 湖北华丽染料工业有限公司 | A kind of composite reactive yellow dye |
| CN107974103B (en) * | 2017-12-04 | 2020-01-21 | 湖北华丽染料工业有限公司 | Composite reactive yellow dye |
Also Published As
| Publication number | Publication date |
|---|---|
| CN100528972C (en) | 2009-08-19 |
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Granted publication date: 20090819 Termination date: 20190818 |