CN102504593A - Blue dye composition and use thereof for fiber dyeing - Google Patents
Blue dye composition and use thereof for fiber dyeing Download PDFInfo
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- CN102504593A CN102504593A CN2011103096483A CN201110309648A CN102504593A CN 102504593 A CN102504593 A CN 102504593A CN 2011103096483 A CN2011103096483 A CN 2011103096483A CN 201110309648 A CN201110309648 A CN 201110309648A CN 102504593 A CN102504593 A CN 102504593A
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- 0 Cc(c(**)c1C)cc(C)c1Nc(c(C(c1ccccc11)=O)c2C1=O)cc(S(O)(=O)=O)c2N Chemical compound Cc(c(**)c1C)cc(C)c1Nc(c(C(c1ccccc11)=O)c2C1=O)cc(S(O)(=O)=O)c2N 0.000 description 3
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Abstract
The invention provides a blue dye composition which comprises one or more dye compounds of the following general formula (1) and one or more dye compounds of the following general formula (2). The blue dye composition has bright and vivid color and is excellent in fastness. Compared with the dye of the following general formula (1), the washing fastness and perspiration fastness of the blue dye composition are greatly improved. The blue dye composition can be successfully applied to dyeing of cellulose fibers, wool, polyamide fibers and mixed fabrics thereof.
Description
Technical field
The present invention relates to a kind of blue dyes compsn and the tint applications on filamentary material thereof.Particularly, the present invention relates to a kind of blue dyes compsn and the tint applications on cellulosic fibre, wool fiber and tynex thereof.
Background technology
The present invention is intended to develop the blue dyes compsn of a kind of coloured light is gorgeous, dyeing behavior is excellent, dyefastness is good cellulosic fibre, wool and tynex dyeing usefulness.It is actually rare that the dyeing property that has above-mentioned excellence concurrently is used for blue dyes or its compsn of cellulosic fibre, wool and tynex.
The practice of printing and dyeing shows that matching stain and some reactive dyestuffs can be successfully used to the dyeing of wool and tynex.
The inventor notices following tart dye species in this Development Practice.The structure of this kind is represented by general formula (1).It represents kind is C.I. acid blue 225.Its structure is following:
The embodiment statement of Chinese patent CN 1869130 (2006) (oasis, Wujiang); Above-mentioned kind and other typical acid blue kinds are all successfully classified as the blue color component in the three primary colors acid dye composition; Therefore can think that C.I. acid blue 225 should be regarded as the good kind of typical matching stain.
The inventor confirms pleasantly surprisedly that in Development Practice the dye species coloured light that topic is shown is gorgeous, and ruddiness is blue, and exhaustion rate and degree of fixation are excellent during dyeing.Has light fastness preferably.But regrettably, its washing fastness and perspiration fastness are unsatisfactory.Both fastness indexs of back are most important for the dyeing of wool and tynex.
For remedying above-mentioned defective; On the basis of a large amount of test practices; The blue dyes compsn that the dyestuff that the inventor finds to adopt general formula (2) expression pleasantly surprisedly and the dyestuff that general formula (1) is represented are formed; Be used for the dyeing of wool, tynex, have that coloured light is gorgeous, tint applications is functional, dyeing each item fastness excellent characteristics.
The dyestuff of general formula (2) expression is that symmetric form triphen dioxazines is reactive dyestuffs, and coloured light is gorgeous, and greenish blue has excellent dyefastness.This structure is Bayer company and the exploitation of Hoechst company.The structure of dyestuff and compound method are seen following patent:
US?4577015(1986)(Bayer)
US?4778603(1988)(Bayer)
US?4783195(1988)(Bayer)
DE?4037606(1992)(Bayer)
US?4774333(1988)(Hoechst)
US?4885385(1989)(Hoechst)
US?5085668(1992)(Hoechst)
US?5352246(1994)(Hoechst)
US?5484459(1996)(Hoechst?Celanese)
The structure of the representative kind of the symmetric form triphen dioxazines based dye of Bayer company exploitation is,
The representative kind of the symmetric form triphen dioxazines based dye of Hoechst company exploitation is:
The blue dyes compsn of the dye composition of general formula (1) expression and the dye composition composition of general formula (2) expression, coloured light is gorgeous, can be between gorgeous indigo plant of ruddiness and the gorgeous basket of green glow free adjustment.The performance of compsn is taken in the length of two components concurrently, presents the dyeing behavior excellence, the effect that dyefastness is good.It was gratifying that wherein when blue dyes of the present invention was used for tynex dyeing, wet fastness was improved and improves.
Research practice shows that blue dyes compsn of the present invention is successfully used to the tint applications of wool, tynex and BLENDED FABRIC thereof.
The inventor does not see the patent and relevant report of the dye composite that above-mentioned two kinds of dyestuffs assembly mixes.
Summary of the invention
The present invention is intended to develop the blue dyes compsn of a kind of coloured light is gorgeous, dyeing behavior is excellent, dyefastness is good cellulosic fibre, wool and tynex dyeing usefulness.
The present invention provides a kind of one or more blue dyes compounds of general formula (1) expression and dye composite of one or more blue dyes compounds that general formula (2) is represented of containing.This dye composite has the characteristic that coloured light is gorgeous, dyeing behavior is excellent, dyefastness is good concurrently, successfully is applied to the dyeing of wool, tynex.
Blue dyes compsn provided by the invention comprise the certain proportion blended one or more be selected from below shown in the dye composition of general formula (1) expression be selected from one or more below shown in the dye composition of general formula (2) expression.
General formula (1)
In the formula:
N is 0,1,2 or 3;
M is 0 or 1;
M is H or alkali metal cation;
R
1For-NHCOCHBrCH
2Br ,-NHCOCBr=CH
2Or
R
2For-NHCOCHBrCH
2Br ,-NHCOCBr=CH
2Or-SO
2Y
3
X is F or Cl;
Y
3For-CH
2CH
2OSO
3M or-CH=CH
2
General formula (2)
In the formula:
R
3And R
4Be H, Cl independently respectively;
Y
1And Y
2Be independently-CH respectively
2CH
2OSO
3M or-CH=CH
2
Q is-OSO
3M,
With-NHCO-V-COOM;
V is-(CH
2) the q-group;
W is-(CH
2)
p-group;
Q and p are respectively 1～4 independently;
M is H or alkali metal cation.
The present invention also provides the tint applications of above-mentioned blue dyes compsn on cellulosic fibre, wool, tynex and BLENDED FABRIC thereof.
Embodiment
Comprise the dye composition of one or more general formulas (1) expression and the dye composition of one or more general formulas (2) expression in the dye composite of the present invention.
In the dye composite of the present invention, the dye composition of general formula (1) expression (being called for short dyestuff I) is 90-10: 10-90, preferably 70-30: 30-70 with the weight ratio of the dye composition (being called for short dyestuff II) of general formula (2) expression.
One preferred embodiment in, (the CH in the general formula (1)
3)
nGroup is worked as n=3 ,-CH
3Group lays respectively on the benzene nucleus-ortho position and the contraposition of NH-group; Work as n=2, CH
3Group lays respectively on the benzene nucleus-contraposition, a position or the ortho position of NH-group; Work as n=1, CH
3Group lays respectively on the benzene nucleus-ortho position or the contraposition of NH-group.
Another preferred embodiment in, the SO in the general formula (1)
3The M group when m=1, is positioned on the benzene nucleus-ortho position or a position of NH-group.
One preferred embodiment in, the R in the general formula (1)
1Group is positioned on the benzene nucleus-ortho position, a position or the contraposition of NH-group.
Another preferred embodiment in, the R in the general formula (1)
2Group is positioned on the benzene nucleus-ortho position, a position or the contraposition of NH-group, be preferably placed at benzene nucleus-NH-group between position or contraposition.
One preferred embodiment in, the Q group in the general formula (2) is selected from-OSO
3M,
With-NHCO-V-COOM, when Q is selected from
During group ,-SO
3The M group is positioned at ortho position, a position or the contraposition of W group on the benzene nucleus; When Q is selected from
During group ,-SO
3The M group is positioned on the benzene nucleus-ortho position, a position or the contraposition of NHCO-group.
Another preferred embodiment in, the V group in the general formula (2) is selected from-(CH
2)
mGroup; W group in the general formula (2) is selected from-(CH
2)
pGroup.Q and p are 1～4 respectively independently, are preferably 1-3.
One preferred embodiment in, the M in general formula (1) and (2) is H, sodium or potassium ion.
In the present invention, the dye composition of general formula (1) expression for example comprises following instance:
Dyestuff I-1
Dyestuff I-2
Dyestuff I-3
Dyestuff I-4
Dyestuff I-5
Dyestuff I-6
Dyestuff I-7 or
Dyestuff I-8;
The dye composition of general formula (2) expression for example comprises following instance:
Dyestuff II-1
Dyestuff II-2
Dyestuff II-3
Dyestuff II-4
Dyestuff II-5
Dyestuff II-6
Dyestuff II-7 or
Dyestuff II-8.
General formula (1) and the represented dye composition of general formula (2) are known dye.
The following patent of preparing method's reference of the dye composition of general formula (1) expression:
CN 101585974 (2009) (the Tianjin moral is triumphant)
US?4442288(1984)(Hoechst)
US?5973147(1999)(Ciba?S.C.)
The chemical structure and the compound method thereof of the dye composition of general formula (2) expression, can consult following patent:
US?4577015(1986)(Bayer)
US?4778603(1988)(Bayer)
US?4783195(1988)(Bayer)
DE?4037606(1992)(Bayer)
US?4774333(1988)(Hoechst)
US?4885385(1989)(Hoechst)
US?5085668(1992)(Hoechst)
US?5352246(1994)(Hoechst)
US?5484459(1996)(Hoechst?Celanese)。
Blue dyes 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 %.For example, electrolyte salt, like sodium sulfate or Repone K, content 0～10 weight %, preferred 2～6 weight %; The pH regulator agent, like SODIUM PHOSPHATE, MONOBASIC or Sodium phosphate, dibasic, content 0～5 weight %, preferred 0.5～2.5 weight %, dust-proofing agent 0～10 weight %, preferred 0.1～2 weight %; Solubility promoter 1～15 weight %, preferred 0.1～3 weight %.The present composition also can be basically by general formula (1) dyestuff of above-mentioned weight ratio with general formula (2) dyestuff is formed or be made up of general formula (1) dyestuff and general formula (2) dyestuff of above-mentioned weight ratio.
Blue dyes preparation of compositions method of the present invention comprises mixes above-mentioned general formula (1) dyestuff and general formula (2) dyestuff by the weight ratio of regulation.Mix available various ordinary method, like 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.
Blue dyes compsn of the present invention is suitable for dyeing and various widely material thereof.
Blue dyes compsn 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.
Embodiment
Each item testing method of embodiment
Each item performance of present embodiment is tested by following each item testing method
1, solubleness: take by weighing a certain amount of dyestuff in the beaker of 250ml, add the hot water of 80 ℃ of 100ml, carry out suction filtration (during suction filtration, pressure 0.075Mpa, 5A qualitative filter paper) after 5 minutes, observe the filter paper residual condition with the mechanical stirrer stirring.Reduce dye strength (G/L), no dyestuff is residual on filter paper, and the dye strength (G/L) of this moment is the solubleness of dyestuff.
2, woolen dyed lifting rate test: by woolen dyed technology dyeing, dyeing concentration is 0.5%, 1%, 2%, 4% with wool fabric, 6%o.w.f (dyestuff is heavy to fabric).Dyeing back fabric is after fixed temperature and humidity is handled, with Datacolor color measurement instrument test its Apparent Depth K/S value and record.
3, dyeing nylon exhaustion rate test: the dye liquor preparation, press the acid dyeing dyeing of nylon.After dyeing finishes, test the absorbancy of dyeing residual liquid and the absorbance of the preceding dye liquor of dyeing respectively.
Exhaustion rate=(absorbance of dye liquor before the absorbance/dyeing of 1-dyeing back dye liquor) * 100%
6, the water colour of anti-chlorination fastness test:, measure by international standard ISO 105E03 with the dyeing nylon fabric.
7, colour fastness to perspiration test:, measure by international standard ISO 105-E04 with the dyeing nylon fabric.
8, fastness to soaping test:, measure by international standard ISO 105-C10 with the dyeing nylon fabric.
9, color fastness to water test:, measure by international standard ISO 105-E01 with the dyeing nylon fabric.
Dye type shown in the according to the form below 1 and consumption thereof by ordinary method uniform mixing in this area, are prepared the various blue dyes compsns of the embodiment of the invention with various dye components.
" % " in the table 1 all representes weight %, is benchmark with the gross weight of dye composite.
Table 1
| Numbering | The dyestuff title | Form |
| 1 | A | 70% dyestuff I-1+30% dyestuff II-1 |
| 2 | B | 50% dyestuff I-1+50% dyestuff II-1 |
| 3 | C | 30% dyestuff I-1+70% dyestuff II-1 |
| 4 | D | 70% dyestuff I-2+30% dyestuff II-3 |
| 5 | E | 50% dyestuff I-2+50% dyestuff II-3 |
| 6 | F | 30% dyestuff I-2+70% dyestuff II-3 |
| 7 | G | 50% dyestuff I-3+50% dyestuff II-4 |
| 8 | Reference X | 100% dyestuff I-1 |
| 9 | Reference Y | 100% dyestuff II-1 |
| 10 | Reference W | 100% dyestuff I-2 |
| 11 | Reference U | 100% dyestuff II-3 |
Embodiment 1
The coloured light of blue dyes compsn of the present invention
The dyestuff color and luster of general formula (I) expression is the ruddiness blueness, and the dyestuff color and luster of general formula (II) expression is the green glow blueness.
The coloured light of blue dyes compsn of the present invention can be adjusted the ratio of general formula (I) dyestuff and general formula (II) dyestuff as required, thereby makes mixture reach bright-coloured sky blue color and luster, and the bright-coloured beautiful sky blue of this type coloured light is that requisite color is formed in the dyestuff.
Embodiment 2
The solubleness test
Measure the solubleness of following dyestuff as stated above, test result is recorded in the table 2
Table 2
Visible by table 2:
Blue dyes compsn of the present invention has solubleness preferably, and level-dyeing property is better.
Embodiment 3
Woolen dyed lifting rate test (the K/S value at absorbing wavelength 620nm place)
Measure the lifting rate of following dyestuff as stated above, test result is recorded in the table 3
Table 3
Visible by table 3:
1) blue dyes compsn of the present invention is compared with the dyestuff of general formula (I) expression, and its woolen dyed lifting rate significantly improves;
2) the lifting rate measured value of blue dyes compsn of the present invention is much higher than the weighted mean that it forms dyestuff, has embodied the effect of compound synergic.
Embodiment 4
Dyeing nylon exhaustion rate is measured
Measure the exhaustion rate of following dyestuff as stated above, test result is recorded in the table 4
Table 4
Visible by table 4:
Blue dyes compsn of the present invention have a splendid dyeing exhaustion rate.
Embodiment 5
The water dungeon of anti-chlorination degree
Measure the water colour of anti-chlorination fastness of following dyestuff as stated above, test result is recorded in the table 5
Table 5
Visible by table 5:
Blue dyes compsn of the present invention still has the good water dungeon of anti-chlorination degree.
Embodiment 6
Colour fastness to perspiration
Measure the colour fastness to perspiration of following dyestuff as stated above, test result is recorded in the table 6
Table 6
Visible by table 6:
Blue dyes compsn of the present invention has excellent fastness to perspiration.
Embodiment 7
Fastness to soaping
Measure the fastness to soaping of following dyestuff as stated above, test result is recorded in the table 7
Table 7
Visible by table 7:
Blue dyes compsn of the present invention has improved the defective of the dyestuff soaping fastness difference of general formula (I) expression effectively.
Embodiment 8
Color fastness to water
Measure the color fastness to water of following dyestuff as stated above, test result is recorded in the table 8
Table 8
Visible by table 8:
Blue dyes compsn of the present invention has excellent color fastness to water.
Claims (10)
1. blue dyes compsn, this dye composite comprise one or more be selected from below shown in the dye composition of general formula (1) expression be selected from one or more below shown in the dye composition of general formula (2) expression:
General formula (1)
In the formula:
N is 0,1,2 or 3;
M is 0 or 1;
M is H or alkali metal cation;
R
1For-NHCOCHBrCH
2Br ,-NHCOCBr=CH
2Or
R
2For-NHCOCHBrCH
2Br ,-NHCOCBr=CH
2Or-SO
2Y
3
X is F or Cl;
Y
3For-CH
2CH
2OSO
3M or-CH=CH
2
General formula (2)
In the formula:
R
3And R
4Be H, Cl independently respectively;
Y
1And Y
2Be independently-CH respectively
2CH
2OSO
3M or-CH=CH
2Q is-OSO
3M,
With-NHCO-V-COOM;
V is-(CH
2)
q-group;
W is-(CH
2)
p-group;
Q and p are respectively 1～4 independently;
M is H or alkali metal cation.
2. the described blue dyes compsn of claim 1, its characteristic are that the dye composition of general formula (1) expression is 90～10: 10～90 with the weight ratio of the dye composition that general formula (2) is represented, is preferably 70～30: 30～70.
3. the described blue dyes compsn of claim 1, its characteristic is, (the CH in the general formula (1)
3)
nGroup is worked as n=3 ,-CH
3Group lays respectively on the benzene nucleus-ortho position and the contraposition of NH-group; Work as n=2 ,-CH
3Group lays respectively on the benzene nucleus-contraposition, a position or the ortho position of NH-group; Work as n=1, CH
3Group lays respectively on the benzene nucleus-ortho position or the contraposition of NH-group.
4. the described blue dyes compsn of claim 1, its characteristic is, the SO in the general formula (1)
3The M group when m=1, is positioned on the benzene nucleus-ortho position or a position of NH-group.
5. the described blue dyes compsn of claim 1 is characterized in that, the R in the general formula (1)
1Group is positioned on the benzene nucleus-ortho position, a position or the contraposition of NH-group; R in the general formula (1)
2Group is positioned on the benzene nucleus-ortho position, a position or the contraposition of NH-group.
6. the described blue dyes compsn of claim 1, its characteristic is, the Q group in the general formula (2) is when Q is selected from
During group ,-SO
3The M group is positioned at ortho position, a position or the contraposition of W group on the benzene nucleus; When Q is selected from
During group ,-SO
3The M group is positioned on the benzene nucleus-ortho position, a position or the contraposition of NHCO-group.
7. each described blue dyes compsn in the claim 1～6, its characteristic are that the dye composition of general formula (1) expression is:
Dyestuff I-1
Dyestuff I-2
Dyestuff I-3
Dyestuff I-4
Dyestuff I-5
Dyestuff I-6
Dyestuff I-7 or
Dyestuff I-8.
8. each described blue dyes compsn in the claim 1～6, its characteristic are that the dye composition of general formula (2) expression is:
Dyestuff II-1
Dyestuff II-2
Dyestuff II-3
Dyestuff II-4
Dyestuff II-5
Dyestuff II-6
Dyestuff II-7 or
Dyestuff II-8.
9. the described blue dyes compsn of claim 1 is characterized in that M is selected from H, sodium or potassium ion, and the n in the general formula (1) is 1,2 or 3, and m is 1; P in the general formula (2) and q are respectively 1～3 independently.
In the claim 1～9 each described blue dyes compsn in the tint applications of cellulosic fibre, wool, tynex and its blending fabric.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201110309648 CN102504593B (en) | 2011-10-13 | 2011-10-13 | Blue dye composition and use thereof for fiber dyeing |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201110309648 CN102504593B (en) | 2011-10-13 | 2011-10-13 | Blue dye composition and use thereof for fiber dyeing |
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|---|---|
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| CN102504593B CN102504593B (en) | 2013-11-06 |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102618073A (en) * | 2012-02-21 | 2012-08-01 | 浙江亿得化工有限公司 | Blue double-reactive-group dye compound, as well as preparation method and composition thereof |
| CN102766355A (en) * | 2012-08-07 | 2012-11-07 | 上海雅运纺织化工股份有限公司 | Anthraquinone blue dye composition and dyeing applications of same to fibers |
| CN105385189A (en) * | 2015-11-30 | 2016-03-09 | 无锡新德印染制品有限公司 | Blue reactive dye composition |
| CN110128847A (en) * | 2019-05-18 | 2019-08-16 | 上海雅运纺织化工股份有限公司 | A kind of Vickery blue composition and its tint applications on fiber |
| CN114350177A (en) * | 2021-12-25 | 2022-04-15 | 苏州科法曼化学有限公司 | Blue dye composition and application thereof |
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| US5456726A (en) * | 1992-12-22 | 1995-10-10 | Sumitomo Chemical Company, Limited | Reactive dye composition and method for dyeing or printing cellulose fiber material using the same |
| CN102115613A (en) * | 2009-12-30 | 2011-07-06 | 上海雅运纺织化工有限公司 | Blue reactive dye composition and dyeing application to fiber material thereof |
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2011
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| US4834769A (en) * | 1986-12-10 | 1989-05-30 | Sandoz Ltd. | Compositions for the dyeing of leather |
| EP0539836A2 (en) * | 1991-10-31 | 1993-05-05 | Bayer Ag | Blue mixtures of reactive dyestuffs with an improved combinability |
| US5456726A (en) * | 1992-12-22 | 1995-10-10 | Sumitomo Chemical Company, Limited | Reactive dye composition and method for dyeing or printing cellulose fiber material using the same |
| DE4306717A1 (en) * | 1993-03-04 | 1994-09-08 | Bayer Ag | Reactive dye brilliant blue mixture |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102618073A (en) * | 2012-02-21 | 2012-08-01 | 浙江亿得化工有限公司 | Blue double-reactive-group dye compound, as well as preparation method and composition thereof |
| CN102766355A (en) * | 2012-08-07 | 2012-11-07 | 上海雅运纺织化工股份有限公司 | Anthraquinone blue dye composition and dyeing applications of same to fibers |
| CN105385189A (en) * | 2015-11-30 | 2016-03-09 | 无锡新德印染制品有限公司 | Blue reactive dye composition |
| CN110128847A (en) * | 2019-05-18 | 2019-08-16 | 上海雅运纺织化工股份有限公司 | A kind of Vickery blue composition and its tint applications on fiber |
| CN110128847B (en) * | 2019-05-18 | 2020-09-29 | 上海雅运新材料有限公司 | Blue acid dye composition and dyeing application thereof on fibers |
| CN114350177A (en) * | 2021-12-25 | 2022-04-15 | 苏州科法曼化学有限公司 | Blue dye composition and application thereof |
| CN114350177B (en) * | 2021-12-25 | 2023-10-17 | 苏州科法曼化学有限公司 | Blue dye composition and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN102504593B (en) | 2013-11-06 |
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