CN101440227A - Yellow reactive dye composition and use thereof - Google Patents
Yellow reactive dye composition and use thereof Download PDFInfo
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- CN101440227A CN101440227A CNA2007101706604A CN200710170660A CN101440227A CN 101440227 A CN101440227 A CN 101440227A CN A2007101706604 A CNA2007101706604 A CN A2007101706604A CN 200710170660 A CN200710170660 A CN 200710170660A CN 101440227 A CN101440227 A CN 101440227A
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Abstract
The invention provides a yellow active dye composition. The composition comprises one or a plurality of known yellow active dyes I and active dyes II mixed according to a certain proportion. The yellow active dye composition has the advantages of fresh golden color and excellent fastness; compared with the component dyes of the combination, the composition is remarkably improved in relative dyeing depth, dye-fixing percentage, dye uptake and increase rate; and amazingly, the photochromic resistance of the composition is also obviously improved.
Description
Technical field
The present invention relates to a kind of reactive dye compositions and the tint applications on filamentary material thereof, particularly relate to Yellow active dye composition and the tint applications on filamentary material thereof.
Background technology
Reactive dyestuffs with bright in colour, chromatogram is complete, applications is easy, with low cost, fastness is good celebrated.Reactive dyestuffs have become the painted most important dye class of cellulose fiber textile.
The development research of Yellow active dye is one of focus of dye industry concern always.
Use in the current Yellow active dye and represent kind to be C.I.Reactive Yellow 145 widely.
Its structural formula is:
This dyestuff has better dyefastness, but also has certain defective, and for example relative dye level, enhancing and level-dyeing property are difficult to satisfy the requirement of current printing and dyeing.The U.S. Pat 5,484 that Ciba-Ceigy company delivers, 899 (1996) have announced the Yellow active dye that a kind of following general formula is represented, and it is with 2, and the 4-diamino benzene sulfonic acid is that coupling component makes.
It is golden yellow that this reactive dyeing is, and all fastness are all good.
Dyestuff W
In the formula, X is Cl or F, and Z is-CH=CH
2Or-CH
2CH
2OSO
3H.
In addition, CN 1569969A (2005) (Shen, Jiangsu is new) has disclosed a kind of reactive yellow SHE dyestuff.The structural formula of this reactive yellow SHE dyestuff is:
Dyestuff X
The inventor thinks that behind the dyestuff of the above-mentioned two kinds of structures of concentrated research introduce 2 in dye structure, 4-diamino benzene sulfonic acid molecule truly has the effect of improving performance.But this class dyestuff remains in the requirement of satisfying current tint applications in some deficiency, for example dye fixing rate, dye uptake, level-dyeing property and all remain further to be improved with the consistency of other dyestuff when dying.
During the last century the nineties, the Japanese Patent that Hoechst company delivers (JP 8048902 (1996)) relates to a kind of black and active dye composition, wherein proposes to use following golden yellow reactive dyestuffs as one of component of consisting of blended black look reactive dyestuffs.
Its general structure is:
Dyestuff Y
The Chinese patent (CN 1118796 (1996)) of Hoechst company application discloses similar foregoing.After this, the patent application CN 1443219 (2003) of Dystar company and WO 02/08341 (2002) disclose the series structure and the synthetic method thereof of above-mentioned dyestuff.
Wherein relate to dye structure of the present invention, for example have:
The inventor finds on the basis of a large amount of research trials, the composition that the general formula (1) of two kinds of reactive dyestuffs that expression is above-mentioned and general formula (2) dyestuff are formed all is significantly improved than the performance of wherein any single-activity dyestuff in degree of fixation, dye uptake and enhancing rate.Being worth pleasantly surprised is that the fast light discoloration that causes of Yellow active dye composition of the present invention also has clear improvement.
Summary of the invention
The inventor is on the basis of a large amount of research trials, pleasantly surprised discovery, the dye composite of the composition of one or more Yellow active dyes of one or more Yellow active dyes of general formula (1) expression and general formula (2) expression has very excellent dyeing behavior and every fastness.
It should be noted that this Yellow active dye composition compares with its composition dyestuff, dye level, degree of fixation, dye uptake, enhancing rate all improve a lot relatively.The fast light discoloration that causes of Yellow active dye composition of the present invention also has clear improvement.
Yellow active dye composition provided by the invention, the dyestuff of general formula (2) expression shown in below the dyestuff of general formula (1) expression shown in below one or more are selected from by the certain proportion blended and one or more are selected from is formed.
General formula (1)
In the formula: M is selected from H or basic metal;
R is selected from H or C
1-3Alkyl;
R
1Be selected from-CONH
2Or-COC
1-3Alkyl;
R
2Be selected from-H ,-C
1-3Alkyl ,-CONH
2,-CH
2CH
2OH or-CH
2CH
2COOH;
X is selected from halogen atom;
Z is selected from-CH
2CH
2OSO
3M or-CH=CH
2
N is selected from 2 or 3.
General formula (2)
In the formula: M is selected from H or basic metal;
R
3And R
4Be selected from H, C
1-3Alkyl or C
1-3Alkoxyl group, preferably be selected from H ,-CH
3With-OCH
3
Y is selected from-CH
2CH
2OSO
3M or-CH=CH
2
M is selected from 1 or 2.
Yellow active dye composition provided by the invention is at carbonyl and/or formamido-material, particularly the application in the filamentary material dyeing.
Specific implementation method
Comprise the dyestuff of one or more general formulas (1) expression and the dyestuff of one or more general formulas (2) expression in the dye composite of the present invention.
In reactive dye compositions of the present invention, the dyestuff of general formula (1) expression (being called for short dyestuff I) is generally 90～10:10～90 with the weight ratio of the dyestuff (being called for short dyestuff II) of general formula (2) expression, be preferably 80～20:20～80, more preferably 70～30:30～70.
One preferred embodiment in, general formula (1)-SO
2The Z group is positioned on the benzene nucleus-the N=N-group between position or contraposition.
Another preferred embodiment in, general formula (2)-SO
2Y group is positioned on the benzene nucleus-the N=N-group between position or contraposition.
One preferred embodiment in, the R in the general formula (1)
3And R
4Group lays respectively on the benzene nucleus-ortho position and a position of N=N-group.
Another preferred embodiment in, in the general formula (2)-SO
3The M group when m=1, is positioned on the benzene nucleus-ortho position, a position or the contraposition of NH-group; When m=2, two-SO
3The M group lays respectively on the benzene nucleus-ortho position and a position of NH-group.
In a particularly preferred embodiment, in general formula (1) and the general formula (2), R is selected from H, C
1-3Alkyl, R
1Be selected from-CONH
2With-COCH
3R
1Be selected from-CONH
2Or-COC
1-3Alkyl; R
2Be selected from-H ,-C
1-3Alkyl or-CONH
2,-CH
2CH
2O ,-CH
2CH
2COOH; R
3And R
4Be selected from respectively-CH
3With-OCH
3
The dyestuff of formula of of the present invention (1) expression for example comprises following example:
Dyestuff I
(dyestuff I-1)
(dyestuff I-2)
(dyestuff I-3)
(dyestuff I-4)
(dyestuff I-5)
(dyestuff I-6)
The dyestuff of formula of of the present invention (2) expression for example comprises following example:
Dyestuff II
(dyestuff II-1)
(dyestuff II-2)
(dyestuff II-3)
(dyestuff II-4)
(dyestuff II-5)
The reactive dyestuffs of general formula (1) and general formula (2) expression are known dye.
US 5,484,899 (1996) (Ciba-Ceigy), CN 1569969A (2005) (Chinese Shen is new) discloses the dye structure and the synthetic method thereof of general formula (1) expression.
CN 1118796 (1996) (Hoechst), JP 7048902 (1996) (Hoechst), CN 1443219 (2003) (Dystar), WO 02/08341 (2002) (Dystar) discloses the dye structure and the synthetic method thereof of general formula (2) expression.
The full content of above-mentioned document is referred among the present invention.
Yellow active dye composition of the present invention also can contain the dye additive of various conventional uses in dyeing and dye formulations, and its consumption can be selected by actual needs, and there is no particular limitation, generally is no more than 20 weight %.Inorganic salts for example is as NaCl, Na
2SO
4, content 0-10 weight %, dispersant 0-10 weight %, the pH regulator agent, as SODIUM PHOSPHATE, MONOBASIC or Sodium phosphate dibasic, content 0-5 weight %, dust-proofing agent 0-10 weight %, solubility promoter 1-15 weight %.The present composition also can be made up of general formula (1) dyestuff and general formula (2) dyestuff of above-mentioned weight ratio basically.
The preparation method of Yellow active dye composition of the present invention comprises above-mentioned general formula (1) dyestuff and general formula (2) dyestuff weight ratio is in accordance with regulations mixed.Mix available various ordinary method, as the mechanically mixing method.During mixing, general formula (1) dyestuff and general formula (2) dyestuff can powder types, or with particle form, or exist with aqueous solution form.For example, mixing step can carry out in suitable shredder such as ball mill or needle mill and in kneader or mixing machine.
Yellow active dye composition of the present invention is suitable for dyeing and various widely material thereof, the material that particularly contains carboxyl and/or formamido-, filamentary material more especially, for example cotton, flax and hemp fibre, and Mierocrystalline cellulose and regenerated cellulose, polyester or polyamide fiber material etc.
Yellow active dye composition of the present invention can be applied to filamentary material and is fixed on the fiber with several different methods as known in the art, for example can dye with dip-dye method or pad dyeing method.
Every testing method of embodiment
Every performance of following embodiment is tested by following every testing method:
1. soaping fastness: measure by international standard ISO 105 C03.
2. colour fastness to perspiration (alkali sweat): measure by international standard ISO 105 E04.
3. colour fastness to perspiration (sour sweat): measure by international standard ISO 105 E04.
4. sun-resistant fastness: measure by international standard ISO 105 B02.
5. dye uptake: prepare two parts of identical dye baths, be respectively A, B.Do not put cloth specimen in the A dye bath.A, B two dye baths are dyeed by the standard dyeing.After dyeing finishes, draw A, B dyeing residual liquid 10mL, constant volume is 500mL respectively.A behind the constant volume, B dyeing residual liquid are diluted to certain multiple M
A, M
B, test the absorptance values X of its diluent when maximum absorption wavelength
A, X
B(X
A, X
BShould be between 0.2～0.7.)
6. enhancing rate: press dye dosage 0.5%, 1%, 2%, 4%, 6%, 8%, 10% configuration dye liquor respectively, dye by the standard dyeing.Cloth specimen after soaping, drying after the dyeing is surveyed the trend map of its K/S value-dye dosage on the color measurement and color match instrument, be the enhancing rate curve of reactive dyestuffs.
7. degree of fixation: prepare two parts of identical dye baths, be respectively A, B.Do not put cloth specimen in the A dye bath.A, B two dye baths are dyeed by the standard dyeing.Prepare identical two parts of the liquid soaped, be respectively C, D.C soaps and does not put DYED FABRICS in the liquid, soaps by the standard technology of soaping, and clean with a small amount of distilled water wash.A and C, B and D are mixed the back with distilled water diluting to 500 milliliter, again it is diluted to certain multiple M
AC, M
BD, test the absorptance values X of its diluent when maximum absorption wavelength
AC, X
BD(X
AC, X
BDShould be between 0.2～0.7.)
8. photochromic: as on same DYED FABRICS, to cut size and be 6 X 10cm
2Two fabrics of I, II, in thermostatic constant wet chamber, fabric I is lain in the standard VERIVIDE COLOR ASSESMENT CABINET, with D65 standard light source irradiation 8 hours, fabric II then was placed on unglazed according to the place.When reaching the specified time, simultaneously fabric I, II being tested aberration on color measurement and color match instrument Datacolor 400, is standard specimen with fabric II, and the variable color situation of test fabric I is with the fast light discoloration that causes of the fabric of judging this type of dyeing.
The employed dye composite of embodiment
Employed dye composite and single composition dyestuff are listed in table 1 in the embodiment of the invention.Comprise following content:
1. the different ratios composition of Yellow active dye of the present invention;
2. the single composition dyestuff of Yellow active dye composition of the present invention.
Table 1
Embodiment 1
Dyestuff A of the present invention and dyestuff B are used for pad dyeing dyeing, and the DYED FABRICS color and luster is bright-coloured golden yellow.Measure by relevant international standard, 4 grades of the washing fastness staining of DYED FABRICS, look become 4-5 level, 4 grades of dry fastnesses, fastness to wet rubbing 3-4 level, 4 grades of colour fastness to perspirations (alkali sweat), 4 grades of colour fastness to perspirations (sour sweat).
Dyestuff A of the present invention and dyestuff B are used for exhaust dyeing, and the DYED FABRICS color and luster is bright-coloured golden yellow.Measure by relevant international standard, 4 grades of the washing fastness staining of DYED FABRICS, look become 4-5 level, 4 grades of dry fastnesses, fastness to wet rubbing 3-4 level, 4 grades of colour fastness to perspirations (alkali sweat), 4 grades of colour fastness to perspirations (sour sweat).
Its working method is as follows:
Contaminate
To be the determined dyestuff of 1% weight with respect to fiber respectively, the solubility promoter of the dust-proofing agent of 0.2 weight % and 0.3 weight % be fully in the being dissolved in charging basket.Under the bath raio condition of 1:10, make fabric in overflow, keep circulation.Added the dye liquor of above-mentioned preparation in 10 minutes, temperature keeps 35 ℃, adds the sodium sulfate of 30 grams per liters after 10 minutes, is warmed up to 60 ℃ then, adds 30 grams per liter soda ash, is incubated 45 minutes, washes then, soaps, washes, dries.
Pad dyeing
Respectively by the consumption of 10 grams per liters with determined dyestuff, fully in the being dissolved in charging basket water, and add the dust-proofing agent of 0.2 weight % and the solubility promoter of 0.3 weight % separately.Put into the groove of continuous dyeing machine with dissolving sufficient dye liquor, fabric is dried after padding dye liquor, and the fabric after the oven dry is after cooling, pad 30 grams per liter soda ash, the padding liquid of 250 grams per liter sodium sulfate, decatize 1 minute in 100 ℃ saturation steam is washed then, is dried then.
The embodiment 2 fast light discolorations that cause
For Yellow active dye, it is fast light, and to cause discoloration particularly important.The colour examining data are listed in table 2, table 3, table 4, table 5 (dye level: the 4%o.w.f. degree of depth).
Table 2
| DE | |
| The not illumination of dyestuff C DYED FABRICS | 0 |
| Dyestuff C DYED FABRICS illumination 8 hours | 0.73 |
| The illumination of dyestuff C DYED FABRICS was placed 8 hours after 8 hours | 1.09 |
Table 3
| DE | |
| The not illumination of dyestuff D DYED FABRICS | 0 |
| Dyestuff D DYED FABRICS illumination 8 hours | 0.92 |
| The illumination of dyestuff D DYED FABRICS was placed 8 hours after 8 hours | 0.75 |
Table 4
| DE | |
| The not illumination of dyestuff E DYED FABRICS | 0 |
| Dyestuff E DYED FABRICS illumination 8 hours | 1.02 |
| The illumination of dyestuff E DYED FABRICS was placed 8 hours after 8 hours | 0.54 |
Table 5
| DE | |
| The not illumination of dyestuff W DYED FABRICS | 0 |
| Dyestuff W DYED FABRICS illumination 8 hours | 1.21 |
| The illumination of dyestuff W DYED FABRICS was placed 8 hours after 8 hours | 1.56 |
* DE explanation: with the dyeing fabric not illumination be standard specimen, it is big more that 8 hours look of illumination becomes DE, illustrates that it is photochromic serious more, the photochromic answer of the big more explanation of DE of placing 8 hours after the illumination is more little, variable color is big more.
As seen from the above table, reactive dye compositions of the present invention (dyestuff C) has the excellent fast light discoloration that causes.Compare with its composition homogencous dyes, it is fast light to cause discoloration and improves significantly and improve.
Below the explanation of each example, the measured value of the relative dye level of Yellow active dye composition of the present invention, dye uptake, degree of fixation is higher than all that its homogencous dyes is painted to be added and mean value, demonstrates fully its synergy.
Example 3 degree of fixation
Degree of fixation is for finally being accounted for the weight percent of dyestuff total amount by the adsorbed dyestuff of fabric.
The mensuration of degree of fixation is listed in table 6, table 7.
Table 6
Table 7
Degree of fixation by table 6, the visible Yellow active dye composition of the present invention of table 7 is higher than the degree of fixation that it forms homogencous dyes.
Example 4 dye uptakes
When dye uptake is different time points fabric on the amount of dying dye yield (testing apparatus: computer color measurement and color match instrument; Model: QuestXE; Producer: HunterLab) account for the weight percent of used dyestuff.Therefore, measure and calculate dye uptake respectively when dyeing, its result is shown in table 8, table 9 respectively.
Table 8
Table 9
As seen from the above table, adding and mean value when the dye composite dye uptake of actual measurement all is higher than single dyeing embodies its collaborative effectiveness.
Because dyeing is the industry of a high pollution, therefore, the characteristics of the relative dye level of Yellow active dye composition of the present invention, degree of fixation height, dye uptake can reduce sewage discharge, reduce the pollution to environment.
Example 5
The relative dye level of dye composite of the present invention (K/S value)
Table 10
Table 11
This shows that Yellow active dye composition of the present invention has excellent every fastness.Yellow active dye composition of the present invention is compared with its component dyestuff, marked improvement is all arranged relative dye level, degree of fixation, dye uptake, enhancing rate, fast light causing aspect the variable color.
Claims (10)
1. Yellow active dye composition, this dye mixture comprise one or more be selected from below shown in the dyestuff of general formula (1) expression and one or more be selected from below shown in the dyestuff of general formula (2) expression:
[general formula (2)]
In the formula: M is selected from H or basic metal;
R is selected from H or C
1-3Alkyl;
R
1Be selected from-CONH
2Or-COC
1-3Alkyl;
R
2Be selected from-H ,-C
1-3Alkyl ,-CONH
2,-CH
2CH
2OH or-CH
2CH
2COOH;
X is a halogen atom;
Z is selected from-CH
2CH
2OSO
3M or-CH=CH
2
Y is selected from-CH
2CH
2OSO
3M or-CH=CH
2
N is selected from 2 or 3;
M is selected from 1 or 2; And
R
3And R
4Be selected from respectively H ,-C
1-3Alkyl or-C
1-3Alkoxyl group.
2. the described Yellow active dye composition of claim 1, its characteristic are that the dyestuff of general formula (1) expression is 90～10:10～90 with the weight ratio of the dyestuff that general formula (2) is represented, preferably 70～30:30～70.
3. Yellow active dye composition as claimed in claim 1 is characterized in that, in the general formula (1)-SO
2The Z group is positioned on the benzene nucleus-the N=N-group between position or contraposition.
4. Yellow active dye composition as claimed in claim 1 is characterized in that, in the general formula (2)-SO
2Y group is positioned on the benzene nucleus-the N=N-group between position or contraposition.
5. Yellow active dye composition as claimed in claim 1 is characterized in that, in the general formula (2)-SO
3The M group when m=1, is positioned on the benzene nucleus-ortho position, a position or the contraposition of NH-group; When m=2, two-SO
3The M group lays respectively on the benzene nucleus-ortho position and a position of NH-group.
6. Yellow active dye composition as claimed in claim 1 is characterized in that, the R in the general formula (2)
3And R
4Group lays respectively on the benzene nucleus-ortho position and a position of N=N-group.
7. Yellow active dye composition as claimed in claim 1, its characteristic be, in general formula (1) and the general formula (2), and R
1Be selected from-CONH
2With-COCH
3R
2Be selected from-H ,-CH
3With-CO NH
2R
3And R
4Be selected from respectively-CH
3With-OCH
3
8. Yellow active dye composition as claimed in claim 1, its characteristic are that general formula (1) is selected from as next group compound:
(dyestuff I-1)
(dyestuff I-2)
(dyestuff I-3)
(dyestuff I-4)
(dyestuff I-5)
(dyestuff I-6).
9. Yellow active dye composition as claimed in claim 1, its characteristic are that general formula (2) is selected from as next group compound:
(dyestuff II-1)
(dyestuff II-2)
(dyestuff II-3)
(dyestuff II-4) and
(dyestuff II-5).
Among the claim 1-9 each described Yellow active dye composition in the application of the dyeing aspect that contains carboxyl and/or formamido-material, particularly filamentary material.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200710170660A CN101440227B (en) | 2007-11-22 | 2007-11-22 | Yellow reactive dye composition and use thereof |
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|---|---|---|---|
| CN200710170660A CN101440227B (en) | 2007-11-22 | 2007-11-22 | Yellow reactive dye composition and use thereof |
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| Publication Number | Publication Date |
|---|---|
| CN101440227A true CN101440227A (en) | 2009-05-27 |
| CN101440227B CN101440227B (en) | 2012-10-03 |
Family
ID=40724844
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN106433216A (en) * | 2016-10-12 | 2017-02-22 | 上海雅运纺织化工股份有限公司 | Yellow reactive dye composition and dyeing application and method thereof on fibers |
| 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 |
| CN108951210A (en) * | 2018-05-25 | 2018-12-07 | 吴江桃源染料有限公司 | A kind of composite reactive golden dye and its application |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1249173C (en) * | 2001-07-04 | 2006-04-05 | 美国永光公司 | Fibre reactive dye |
| DE10212769A1 (en) * | 2002-03-22 | 2003-10-02 | Dystar Textilfarben Gmbh & Co | Reactive dye mixtures, used for dyeing and printing fibrous material with hydroxyl or carbonamido groups, contain mono- and di-sulfonated amino-naphthol disazo and optionally monoazo dyes |
| DE10337636A1 (en) * | 2003-08-16 | 2005-03-17 | Dystar Textilfarben Gmbh & Co. Deutschland Kg | Dye mixtures of fiber-reactive azo dyes, their preparation and their use |
| DE102005047391A1 (en) * | 2005-10-05 | 2007-04-12 | Dystar Textilfarben Gmbh & Co. Deutschland Kg | Dyes and dye mixtures of fiber-reactive azo dyes, their preparation and their use |
| CN100362055C (en) * | 2006-01-26 | 2008-01-16 | 浙江龙盛集团股份有限公司 | Composite reactive yellow dye |
| CN100528972C (en) * | 2006-08-18 | 2009-08-19 | 浙江龙盛集团股份有限公司 | Composite reactive dye |
-
2007
- 2007-11-22 CN CN200710170660A patent/CN101440227B/en active Active
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN106433216A (en) * | 2016-10-12 | 2017-02-22 | 上海雅运纺织化工股份有限公司 | Yellow reactive dye composition and dyeing application and method thereof on fibers |
| CN106433216B (en) * | 2016-10-12 | 2018-04-20 | 上海雅运纺织化工股份有限公司 | Yellow active 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 |
| CN108951210A (en) * | 2018-05-25 | 2018-12-07 | 吴江桃源染料有限公司 | A kind of composite reactive golden dye and its application |
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| Publication number | Publication date |
|---|---|
| CN101440227B (en) | 2012-10-03 |
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