CN103554993A - Red active dye composition and dyeing application thereof to fibers - Google Patents
Red active dye composition and dyeing application thereof to fibers Download PDFInfo
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- CN103554993A CN103554993A CN201310582491.0A CN201310582491A CN103554993A CN 103554993 A CN103554993 A CN 103554993A CN 201310582491 A CN201310582491 A CN 201310582491A CN 103554993 A CN103554993 A CN 103554993A
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- dye composition
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- red reactive
- reactive dye
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- 0 CC([C@]1N=Nc2ccccc2)=Cc2cc(*)cc(Nc3nc(*)nc(N(*)c4ccccc4)n3)c2C1O Chemical compound CC([C@]1N=Nc2ccccc2)=Cc2cc(*)cc(Nc3nc(*)nc(N(*)c4ccccc4)n3)c2C1O 0.000 description 1
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Abstract
The invention provides a red active dye composition and a dyeing application thereof. The dye composition contains one or more dye compounds as shown in a general formula (1) and one or more dye compounds as shown in a general formula (2). The red active dye composition provided by the invention is extraordinarily bright in color and has excellent dyeing properties such as leveling property and compatibility. Therefore, the red active dye composition can be confirmed to have industrial practice value and prospect.
Description
Technical field
The present invention relates to a kind of reactive dye compositions and in the tint applications of filamentary material, particularly, the present invention relates to a kind of red reactive dye composition and the tint applications on filamentary material thereof.
Background technology
The dyestuff that the dyestuff that the general formula the present invention relates to (1) represents and general formula (2) represent, although structural formula is very similar, because its coloured light and dyeing behavior exist great difference, so belongs to two kinds of dissimilar dyestuffs.The dyestuff that general formula (2) represents, its Representative Cultivars is Reactive Brilliant Red M-8B.Structural formula is as follows:
This dye shade is that blue light is red, synthetic convenient, with low cost.Past attempts is used as one of reactive dyestuffs three primary colors.But put into practice, show, this dyestuff, due to some defect of dyeing behavior, loses its using value gradually.
The dyestuff that general formula (1) represents, its Representative Cultivars is active gorgeous purple.In dyeing, belong to complementary colors kind, be seldom applied.
The inventor is on the basis of lot of experiments research, find uncannily the dyestuff of general formula (1) expression and the dye composite of the dye composition that general formula (2) represents that form by a certain percentage, compare with its component red reactive dyes, not only coloured light is more gorgeous, and more gives excellent level-dyeing property and good coordination.
Inventor's confirmation, red reactive dye composition of the present invention makes the application of Reactive Brilliant Red M-8B obtain new lifting.The inventor be sure of, the present invention has the extensive prospect of industrial application.
Summary of the invention
The inventor is by experimental study, be surprised to find the red dye composition that contains the red reactive dyes compound that red reactive dyes compound that one or more general formulas (1) represent and one or more general formulas (2) represent, there is very gorgeous coloured light and excellent dyeing behavior, such as level-dyeing property and compatibleness etc.Thereby red reactive dye composition of the present invention has industrial practice and is worth and prospect.
Red reactive dye composition provided by the invention comprises the dye composition that dye composition that a certain proportion of one or more general formulas (1) shown in being selected from below represent and one or more general formula (2) shown in being selected from below represents.
In formula:
M is H or alkali metal cation;
R
1for H or C
1-C
2alkyl;
R
2and R
3be H, C independently respectively
1-C
2alkyl or C
1-C
2alkoxyl group;
X
1for Cl or F;
R
7for C
1-C
2alkoxyl group;
Y
1for-CH
2cH
2oSO
3m or-CH=CH
2;
In formula:
M is H or alkali metal cation;
R
4for H or C
1-C
2alkyl;
R
5and R
6be H, C independently respectively
1-C
2alkyl or C
1-C
2alkoxyl group;
X
2for Cl or F;
Y
2for-CH
2cH
2oSO
3m or-CH=CH
2.
The present invention also provides the application of above-mentioned red reactive dye composition at the dyeing aspect of hydroxyl and/or formamido-material, particularly filamentary material.
Specific implementation method
One preferred embodiment in, in the dye composition that the dye composition that dye composite of the present invention is represented by one or more general formulas (1) and one or more general formulas (2) represent and dyeing and dye formulations, the conventional dye additive using forms.
One preferred embodiment in, the dye composition that in red reactive dye composition of the present invention, one or more general formulas (1) represent: the weight ratio of the dye composition that one or more general formulas (2) represent is 1～15:85～99, is preferably 2～12:88～98.
One preferred embodiment in, general formula (1) right side-SO
2y
1group, is positioned at NR on benzene nucleus
1the contraposition of group or a position.The R on general formula (1) right side
2and R
3group, is separately located in respectively NR on benzene nucleus
1the contraposition of group, ortho position or a position.
Another preferred embodiment in, general formula (2) right side-SO
2y
2group, is positioned at NR on benzene nucleus
4the contraposition of group or a position; The R on general formula (2) right side
5and R
6group, is separately located in respectively NR on benzene nucleus
4the contraposition of group, ortho position or a position.
One preferred embodiment in, the R in general formula (1) left side
7group, is positioned at contraposition or a position of azo group on benzene nucleus.
Another preferred embodiment in, general formula (2) left side-COOM group, be positioned at contraposition or a position of azo group on benzene nucleus.
One preferred embodiment in, the Y in general formula (1) and general formula (2)
1and Y
2group, is-CH respectively independently
2cH
2oSO
3m or-CH=CH
2.
One preferred embodiment in, M is hydrogen, sodium or potassium cationic.
Another preferred embodiment in, the X in general formula (1) and general formula (2)
1and X
2group is Cl or F respectively independently.
The dye composition that general formula (1) represents, for example, comprise following example:
The dye composition that general formula (2) represents, for example, comprise following example:
The dyestuff that the dyestuff that general formula (1) represents and general formula (2) represent is known dye, and its synthetic method can be with reference to following patent:
US6165231（2000）（Dystar）
US6136045（2000）（Dystar）
US5665124（1997）（Bayer）
US5428141（1995）（Bayer）
US5359040(1994) (Sumitomo)
US5131917(1992) (Sumitomo)
The synthetic method of the dyestuff that general formula (1) represents is:
C.I. reactive violet 8# and para-ester or a position ester, or derivatives thereof are carried out to condensation reaction and make:
Above-mentioned synthetic information content is referred in the present invention.
Red reactive 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 according to actual needs, and there is no particular limitation, is generally no more than 20 % by weight.For example, electrolyte salt, as sodium sulfate or Repone K, content 0～10 % by weight, preferably 2～6 % by weight; PH adjusting agent, as SODIUM PHOSPHATE, MONOBASIC or Sodium phosphate dibasic, content 0～5 % by weight, preferred 0.5～2.5 % by weight, dust-proofing agent 0～10 % by weight, preferred 0.1～2 % by weight; Solubility promoter 1～15 % by weight, preferred 0.1～3 % by weight.The present composition also can be substantially comprised of general formula (1) dyestuff and general formula (2) dyestuff of above-mentioned weight ratio.
The preparation method of red reactive 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 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 suitable shredder as ball mill or needle mill in and in kneader or mixing machine, carry out.
Red reactive dye composition of the present invention is suitable for dyeing and various materials widely thereof, particularly contain the material of carboxylic acid 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.
Red reactive dye composition of the present invention can be applied to filamentary material and be affixed on fiber by several different methods as known in the art, for example, can dye by dip-dye method or pad dyeing method.
Embodiment
Every testing method of embodiment
The properties of the present embodiment is tested by following every testing method
1, enhancing rate test: pure cotton fabric is pressed to 60 ℃ of constant temperature dyeings of reactive dyestuffs, and dyeing concentration is that 0.5%, 1%, 2%, 4%, 6%o.w.f(dyestuff is to fabric weight).After dyeing, fabric, after fixed temperature and humidity is processed, is tested its Apparent Depth K/S value record with Datacolor color measurement instrument.
2, just dye rate and degree of exhaustion test: dye liquor preparation, press 60 ℃ of constant temperature dyeings of reactive dyestuffs.Respectively before adding alkali and on dye and finish to sample before soap boiling, measure the absorbance of dyeing residual liquid, with dye liquor absorbance comparison before dyeing.
Just dye rate=(1-adds the absorbance of the front dye liquor of absorbance/dyeing of the front dye liquor of alkali) * 100%
Degree of exhaustion=(1-soap before before the absorbance/dyeing of dye liquor the absorbance of dye liquor) * 100%
3, degree of fixation test: dye liquor preparation, press 60 ℃ of constant temperature dyeings of reactive dyestuffs.After dyeing finishes, the cloth specimen in B dye bath is carried out to washing according to the following steps, and by dyeing residual liquid, the washing raffinate of each step concentrates on constant volume in the volumetric flask of a 500mL.When B dye bath cloth specimen carries out soap boiling, in A dye bath, also add the detergent of same amount to carry out soap boiling.A dye bath is cooled to room temperature after soaping and finishing, and constant volume is 500mL.A after constant volume, B dyeing residual liquid are diluted to certain multiple MA, MB, and testing absorptance values XA, the XB(XA of its diluent when maximum absorption wavelength, XB should be between 0.2～0.7).
Degree of fixation=(1-XBMB/XAMA) * 100%
4, colour fastness to perspiration test: measure by international standard ISO105-E04.
5, water-fastness colour fastness test: measure by international standard ISO105-C10.
6, colour fasteness to sunlight test: measure by international standard ISO105-B02.
7, colour fastness to chlorinated water test: measure by international standard ISO105-E03
Dye type shown according to the form below 1 and consumption thereof evenly mix various dye components by ordinary method in this area, the various red reactive dye compositions of the preparation embodiment of the present invention.
" % " in table 1 all represents % by weight, and the gross weight of dye composite of take is benchmark.
Table 1
| Numbering | Reactive dyestuffs title | Form |
| 1 | A | 5% dyestuff 1-1+95% dyestuff 2-1 |
| 2 | B | 10% dyestuff 1-1+90% dyestuff 2-1 |
| 7 | Reference X | Dyestuff 1-1 |
| 8 | Reference Y | Dyestuff 2-1 |
| 9 | Reference Z | Reactive red C.I.195# |
Note: reference Z is the most frequently used in current industry, for the blue light orchil of trichromatic system.
Embodiment 1
The coloured light of red reactive dye composition of the present invention
The bright-coloured rose of coloured light of reactive dye compositions of the present invention, the active red dye of this colour system routine is difficult to reach, and in middle Resist Reactive Dyes chromatogram, belongs to the blank colour system that urgent need is filled up.By Dyeing Practice, red reactive dye composition of the present invention can be realized the gorgeous rhodo colour system of the listed various color and lusters of following table:
Table 2
From table 2:
Red reactive dye composition of the present invention is compared with reference dyestuff, better tint applications in gorgeous rhodo colour system.
Embodiment 2
Enhancing rate test (the K/S value at absorbing wavelength 560nm place)
The enhancing rate that is determined as follows as stated above dyestuff, test result is recorded in table 3
Table 3
From table 3:
1) red reactive dye composition of the present invention, compares with the dyestuff that general formula (1) represents, its enhancing rate significantly improves, and has improved general formula (1) and has represented the poor shortcoming of dyestuff depth;
2) the enhancing rate measured value of red reactive dye composition of the present invention, is much higher than the weighted mean that it forms dyestuff, has embodied the effect of compound synergic.
Embodiment 3
Just dying rate and degree of exhaustion measures
First rate and the degree of exhaustion of dying that is determined as follows as stated above dyestuff, test result is recorded in table 4
Table 4
* the first rate of dying of conventional yellow and blue active dye is all in 55% left and right.
From table 4:
The first rate of dying of red reactive dye composition of the present invention is moderate, can match with conventional yellow, red reactive dyes, and degree of exhaustion is good, has good uniform dyeing property and compatibleness.
Embodiment 4
Degree of fixation is measured
The degree of fixation that is determined as follows as stated above dyestuff, test result is recorded in table 5
Table 5
From table 5:
The degree of fixation of red reactive dye composition of the present invention is compared and is improved with reference dyestuff, has embodied the effect of multiple spelling synergy.
Embodiment 5
Colour fastness to perspiration
The colour fastness to perspiration that is determined as follows as stated above dyestuff, test result is recorded in table 6
Table 6
From table 6:
Red reactive dye composition of the present invention has excellent fastness to perspiration.
Embodiment 6
Washing fastness
The washing fastness that is determined as follows as stated above dyestuff, test result is recorded in table 7
Table 7
From table 7:
Red reactive dye composition of the present invention has excellent washing fastness.
Embodiment 7
Sunlight fastness
The sunlight fastness that is determined as follows as stated above dyestuff, test result is recorded in table 8
Table 8
From table 8:
Red reactive dye composition of the present invention still has good sunlight fastness.
Embodiment 8
Colour fastness to chlorinated water
The sunlight fastness that is determined as follows as stated above dyestuff, test result is recorded in table 9
Table 9
From table 9:
Red reactive dye composition of the present invention still has good colour fastness to chlorinated water.
Claims (10)
1. a red reactive dye composition, this dye composite contains the dye composition that dye composition that one or more general formulas (1) represent and one or more general formulas (2) represent:
In formula:
M is H or alkali metal cation;
R
1for H or C
1-C
2alkyl;
R
2and R
3be H, C independently respectively
1-C
2alkyl or C
1-C
2alkoxyl group;
X
1for Cl or F;
R
7for C
1-C
2alkoxyl group;
Y
1for-CH
2cH
2oSO
3m or-CH=CH
2;
In formula:
M is H or alkali metal cation;
R
4for H or C
1-C
2alkyl;
R
5and R
6be H, C independently respectively
1-C
2alkyl or C
1-C
2alkoxyl group;
X
2for Cl or F;
Y
2for-CH
2cH
2oSO
3m or-CH=CH
2.
2. red reactive dye composition claimed in claim 1, its characteristic is, the dye composition that described one or more general formulas (1) represent: the weight ratio of the dye composition that described one or more general formulas (2) represent is 1～15:85～99, is preferably 2～12:88～98.
3. red reactive dye composition claimed in claim 1, its characteristic is, the R in general formula (1) left side
7group, is positioned at contraposition or a position of azo group on benzene nucleus.
4. red reactive dye composition claimed in claim 1, its characteristic is, general formula (1) right side-SO
2y
1group, is positioned at NR on benzene nucleus
1the contraposition of group or a position, the R on general formula (1) right side
2and R
3group, is separately located in respectively NR on benzene nucleus
1the ortho position of group or a position.
5. red reactive dye composition claimed in claim 1, its characteristic is, general formula (2) left side-COOM group, be positioned at contraposition or a position of azo group on benzene nucleus.
6. red reactive dye composition claimed in claim 1, its characteristic is, general formula (2) right side-SO
2y
2group, is positioned at NR on benzene nucleus
4the contraposition of group or a position; The R on general formula (2) right side
5and R
6group, is separately located in respectively NR on benzene nucleus
4the ortho position of group or a position.
7. red reactive dye composition claimed in claim 1, its characteristic is, the Y in general formula (1) and general formula (2)
1and Y
2group is-CH respectively independently
2cH
2oSO
3m; X in general formula (1) and general formula (2)
1and X
2group is Cl respectively independently; M in general formula (1) and general formula (2) is H, sodium or potassium cationic.
8. the red reactive dye composition described in any one in claim 1～7, its characteristic is, the dye composition that general formula (1) represents is:
9. the red reactive dye composition described in claim 1～7 any one, its characteristic is, the dye composition that general formula (2) represents is:
10. the tint applications of the red reactive dye composition described in any one on hydroxyl and/or formamido-material, particularly filamentary material in claim 1～9.
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|---|---|---|---|
| CN201310582491.0A CN103554993B (en) | 2013-11-19 | 2013-11-19 | Red reactive dye composition and the tint applications on fiber thereof |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310582491.0A CN103554993B (en) | 2013-11-19 | 2013-11-19 | Red reactive dye composition and the tint applications on fiber thereof |
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| Publication Number | Publication Date |
|---|---|
| CN103554993A true CN103554993A (en) | 2014-02-05 |
| CN103554993B CN103554993B (en) | 2016-05-11 |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104194395A (en) * | 2014-08-06 | 2014-12-10 | 浙江瑞华化工有限公司 | Reactive red dye composition, reactive red dye as well as preparation method and application of active red dye |
| CN104774484A (en) * | 2014-12-29 | 2015-07-15 | 浙江科永化工有限公司 | Reactive red dye composition |
| CN108102421A (en) * | 2017-11-30 | 2018-06-01 | 浙江科永化工有限公司 | A kind of active red dye composition |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102277011A (en) * | 2011-06-17 | 2011-12-14 | 上海雅运纺织化工有限公司 | Red reactive dye composition and application thereof to fiber dyeing |
-
2013
- 2013-11-19 CN CN201310582491.0A patent/CN103554993B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102277011A (en) * | 2011-06-17 | 2011-12-14 | 上海雅运纺织化工有限公司 | Red reactive dye composition and application thereof to fiber dyeing |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104194395A (en) * | 2014-08-06 | 2014-12-10 | 浙江瑞华化工有限公司 | Reactive red dye composition, reactive red dye as well as preparation method and application of active red dye |
| CN104774484A (en) * | 2014-12-29 | 2015-07-15 | 浙江科永化工有限公司 | Reactive red dye composition |
| CN104774484B (en) * | 2014-12-29 | 2017-02-22 | 浙江科永化工有限公司 | Reactive red dye composition |
| CN108102421A (en) * | 2017-11-30 | 2018-06-01 | 浙江科永化工有限公司 | A kind of active red dye composition |
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| Publication number | Publication date |
|---|---|
| CN103554993B (en) | 2016-05-11 |
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