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CN102286219A - Red active dye composition and dyeing application thereof in fibers - Google Patents

Red active dye composition and dyeing application thereof in fibers Download PDF

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Publication number
CN102286219A
CN102286219A CN2011101650056A CN201110165005A CN102286219A CN 102286219 A CN102286219 A CN 102286219A CN 2011101650056 A CN2011101650056 A CN 2011101650056A CN 201110165005 A CN201110165005 A CN 201110165005A CN 102286219 A CN102286219 A CN 102286219A
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Prior art keywords
dyestuff
dye composition
group
general formula
reactive dye
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CN2011101650056A
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Inventor
郑怡华
曾建平
顾喆栋
谢兵
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SHANGHAI ARGUS TEXTILE CHEMICALS CO Ltd
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SHANGHAI ARGUS TEXTILE CHEMICALS CO Ltd
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Abstract

The invention provides a red active dye composition and dyeing application thereof in fibers. The dye composition contains one or more dye compounds expressed as a general formula (1) and one or more dye compounds expressed as a general formula (2). The red active dye composition shows excellent application performance in dyeing of wool. The red active dye composition has good dyeing fastness.

Description

Red reactive dye composition and the tint applications on fiber thereof
Technical field
The present invention relates to a kind of reactive dye compositions and, particularly, the present invention relates to a kind of red reactive dye composition and the tint applications on filamentary material thereof in the tint applications of filamentary material.
Background technology
The present invention relates to red reactive dye composition and application thereof that a kind of reactive dyestuffs that contain cyanogen ammonia triazinyl participate in composition.
As far back as 1973, Ciba-Geigy company delivered United States Patent (USP) (US 3758470), disclosed the structure and the application characteristic thereof of the reactive dyestuffs that adopt cyanogen ammonia triazinyl.
At the beginning of the nineties in last century, Hoechst company is to structure, the synthetic method of all kinds of reactive dyestuffs that contain cyanogen ammonia triazinyl and should be used as the deep research of system.The patent that Hoechst company delivers continuously has:
US?5015731(1991)(Hoechst)
US?5200512(1993)(Hoechst)
US?5225544(1993)(Hoechst)
US?5290922(1994)(Hoechst)
US?5290923(1994)(Hoechst)
US?5349057(1994)(Hoechst)
WO?90/13603(1990)(Hoechst)
WO?90/13604(1990)(Hoechst)
Above-mentioned patent relates to each class formation that contains cyanogen ammonia triazinyl, the reactive dyestuffs of various color and lusters.Patent shows that all kinds of reactive dyestuffs that contain cyanogen ammonia triazinyl have good enhancing rate and degree of fixation.What be worth proposition is that these class reactive dyestuffs have very excellent every dyefastness, for example light fastness, sweat proof light fastness, fastness to chlorinated water, fastness to chlorine-bleaching, resisting hydrogen peroxide fastness and fastness to hot pressing etc.These class reactive dyestuffs are easy to discharge, have the good antiacid performance of fading.
Hoechst company in US 5225544 (1993) (Hoechst), discloses the red reactive dyes of time array structure in the above-mentioned exploitation that contains cyanogen ammonia triazinyl reactive dyestuffs.
Figure BDA0000069071400000021
Said structure is the representative structure of the dyestuff of general formula (2) expression.
The another kind of red reactive dyes that the present invention relates to is the dyestuff of general formula (1) expression, and its representative structure is the C.I. REACTIVE Red 195.The structure of this kind at first is published in the patent US 4341699 (1982) that SUMITOMO CHEMICAL company applies for.It is red that this kind coloured light is blue light, has certain dyefastness, and with low cost, thereby the concern on the boundary that extremely prints and dyes.
But secular application practice shows, the defective that this kind dyeing kinetics is slow, reactivity is poor, enhancing rate is low etc., the industrial widespread use that has a strong impact on and incur loss through delay this kind.
In the research that improves the C.I. REACTIVE Red 195, the inventor is by a large amount of tint applications experimental studies, find dyestuff by general formula (1) expression pleasantly surprisedly, red reactive dye composition with the dyestuff of general formula (2) expression is formed with certain proportion has very excellent dyefastness and application performance.
The inventor finds pleasantly surprisedly, the every dyefastness and the application performance of red reactive dye composition of the present invention, not only significantly be better than it and form dyestuff---the dyestuff of general formula (1) expression, and obviously be better than the reactive dye compositions that US 6165231 (2000) (Dystar) is provided.
The inventor confirms, the application performance of red reactive dye composition of the present invention can adapt to harsh day by day printing and dyeing demand effectively, thereby have wide industrial practice prospect.
Summary of the invention
The inventor is by experimental study, and the orchil composition that is surprised to find the red reactive dyes compound of the red reactive dyes compound that contains one or more general formulas (1) expression and one or more general formulas (2) expression has very excellent dyeing behavior and every fastness.
Application data shows that the dyeing behavior of red reactive dye composition of the present invention is compared with its component dyestuff, and tangible lifting and improvement are all arranged.
It should be noted that the dyeing behavior of red reactive dye composition of the present invention, compare, also improve to some extent and improve with the reactive dye compositions that US 6165231 (2000) (Dystar) is provided.
Red reactive dye composition provided by the invention is 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 combination or blended by a certain percentage and one or more are selected from.
Figure BDA0000069071400000031
General formula (1)
In the formula:
Z 1For-CH 2CH 2OSO 3M or-CH=CH 2
R 1And R 2Be H, C independently respectively 1-C 4Alkyl, C 1-C 4Alkoxyl group or-SO 3M;
R 3Be H or C 1-C 4Alkyl;
R 4Be H or C 1-C 4Alkyl;
X is Cl, F or NHCN;
M is H or alkali metal cation;
P is 0 or 1;
Figure BDA0000069071400000032
General formula (2)
In the formula:
Z 2For-CH 2CH 2OSO 3M or-CH=CH 2
R 5And R 6Be H, C independently respectively 1-C 4Alkyl, C 1-C 4Alkoxyl group or sulfonic group;
R 7Be H or C 1-C 4Alkyl;
R 8And R 9Be H, C independently respectively 1-C 4Alkyl, C 1-C 4Alkoxyl group or sulfonic group;
M is H or alkali metal cation.
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
In a preferred implementation, form by 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 red reactive dye composition of the present invention.
In reactive dye compositions of the present invention, the dye composition of general formula (1) expression: the weight ratio of the dye composition of general formula (2) expression is 90~10: 10~90, is preferably 70~30: 30~70, be preferably 60~40: 40~60.
One preferred embodiment in, in the general formula (1)-SO 2Z 1Group is positioned on the benzene nucleus
Figure BDA0000069071400000041
The contraposition of group or a position; R in the general formula (1) 1And R 2Group is separately located on the benzene nucleus respectively
Figure BDA0000069071400000042
The ortho position of group, contraposition or a position.
Another preferred embodiment in, what link to each other with diazo left side in the general formula (1) is benzene nucleus or naphthalene nuclear derivatives.
One preferred embodiment in, link to each other with diazo left side in the general formula (1) be benzene nucleus the time, p equals 0, R 4Group is positioned on the benzene nucleus-contraposition or a position of N=N-group.
Another preferred embodiment in, link to each other with diazo left side in the general formula (1) examine for naphthalene the time, under the situation of p=1, sulfonic acid group is positioned at 5 that naphthalene is examined; Under the situation of p=0, R 4Group is positioned at 4,5,6 or 7 on the naphthalene nuclear.
One preferred embodiment in, general formula (2) right side-SO 3The M group is positioned on the benzene nucleus
Figure BDA0000069071400000043
The contraposition of group, a position or ortho position; The R on right side in the general formula (2) 8And R 9Group is separately located on the benzene nucleus respectively
Figure BDA0000069071400000044
The contraposition of group, a position or ortho position.
Another preferred embodiment in, general formula (2) left side-SO 2Z 2Group is positioned on the benzene nucleus-ortho position, a position or the contraposition of N=N-group; The R in left side in the general formula (2) 5And R 6Group is separately located in respectively on the benzene nucleus-ortho position, a position or the contraposition of N=N-group.
The dye composition of general formula (1) expression for example comprises following example:
Figure BDA0000069071400000051
Dyestuff 1-1
Figure BDA0000069071400000052
Dyestuff 1-2
Figure BDA0000069071400000053
Dyestuff 1-3
Dyestuff I-4
Figure BDA0000069071400000062
Dyestuff I-5
Figure BDA0000069071400000063
Dyestuff I-6
Figure BDA0000069071400000071
Dyestuff I-7 or
Figure BDA0000069071400000072
Dyestuff I-8.
The dye composition of general formula (2) expression for example comprises following example:
Figure BDA0000069071400000073
Dyestuff 2-1
Figure BDA0000069071400000081
Dyestuff 2-2
Figure BDA0000069071400000082
Dyestuff 2-3
Dyestuff 2-4
Figure BDA0000069071400000091
Dyestuff 2-5
Dyestuff 2-6
Figure BDA0000069071400000093
Dyestuff 2-7 or
Dyestuff 2-8.
The reactive dye compound of general formula (1) and general formula (2) expression is known dye.
Following patent has been announced the structure and the synthetic method thereof of the dyestuff of general formula (1) expression, and they are:
US 4341699 (1982) (Sumitomo)
US 5131917 (1992) (Sumitomo)
JP 5117538 (1993) (Sumitomo)
US 5324329 (1994) (Sumitomo)
US 5359040 (1994) (Sumitomo)
The structure and the synthetic method thereof of the dyestuff of general formula (2) expression can be consulted US 5225544 (1993) (Hoechst)
The full content of above-mentioned document is referred among 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 by actual needs, and there is no particular limitation, generally is no more than 20 weight %.For example, electrolyte salt, as sodium sulfate or Repone K, content 0~10 weight %, preferred 2~6 weight %; The pH regulator agent, as 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 made up of general formula (1) dyestuff and general formula (2) dyestuff of above-mentioned weight ratio basically.
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 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.
Red reactive dye composition of the present invention is suitable for dyeing and various widely material thereof, the material that particularly contains 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 is affixed 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
Every testing method of embodiment
Every performance of present embodiment is tested by following every testing method
1, woolen dyed enhancing rate test:
Wool yarn is pressed 98 ℃ of heating process dyeing of matching stain, 0.5%, 1%, 2%, 4%o.w.f (dyestuff is heavy to fabric).Dyeing back fabric is tested its Apparent Depth K/S value and record with the Datacolor color measurement instrument after fixed temperature and humidity is handled.
2, colour fastness to perspiration test: measure by international standard ISO 105-E04.
3, fastness to soaping test: measure by international standard ISO 105-C10.
4, color fastness to water test: measure by international standard ISO 105-E01.
5, colour fasteness to sunlight test: measure by international standard ISO 105-B02.
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 red reactive dye compositions of the embodiment of the invention with various dye components.
" % " in the table 1 all represents weight %, is benchmark with the gross weight of dye composite.
Table 1
Numbering The reactive dyestuffs title Form
1 A 70% dyestuff 1-1+30% dyestuff 2-1
2 B 50% dyestuff 1-1+50% dyestuff 2-1
3 C 30% dyestuff 1-1+70% dyestuff 2-1
4 D 70% dyestuff 1-4+30% dyestuff 2-4
5 E 50% dyestuff 1-4+50% dyestuff 2-4
6 F 30% dyestuff 1-4+70% dyestuff 2-4
7 Reference X 100% dyestuff 1-1
8 Reference Y 100% dyestuff 2-1
9 Reference Z 50% reactive red C.I.195+50% reactive red C.I.198
* reference Z is (Dystar) cited embodiment of US 6165231 (2000).
Embodiment 1
Woolen dyed enhancing rate test (the K/S value at absorbing wavelength 520nm place)
Measure the enhancing rate of following dyestuff as stated above, test result is recorded in the table 2
Table 2
Figure BDA0000069071400000121
By table 2 as seen:
1) red reactive dye composition of the present invention is used for woolen dyed going up and shows its excellent application performance.
2) red reactive dye composition of the present invention all apparently higher than its weighted mean of forming dyestuff, embodies the effect of compound synergic at woolen dyed enhancing rate measured value.
3) red reactive dye composition of the present invention, its enhancing rate on wool is apparently higher than (Dystar) conventional dye combinations of US 6165231 (2000).Consult the dyeing enhancing rate data of dye composite B and dye composite reference Z in the table 2.
Embodiment 2
Colour fastness to perspiration
Measure the colour fastness to perspiration of following dyestuff as stated above, test result is recorded in the table 3
Table 3
Figure BDA0000069071400000131
By table 3 as seen:
Red reactive dye composition of the present invention has good fastness to perspiration.
Embodiment 3
Fastness to soaping and color fastness to water
Measure fastness to soaping, color fastness to water and the color fastness to sea water of following dyestuff as stated above, test result is recorded in the table 4
Table 4
Figure BDA0000069071400000141
By table 4 as seen:
Red reactive dye composition of the present invention has good fastness to soaping and color fastness to water, is better than the corresponding fastness of dye composite reference Z.
Embodiment 4
Sun-resistant fastness
Measure the sun-resistant fastness of following dyestuff as stated above, test result is recorded in the table 5
Table 5
Figure BDA0000069071400000142
Figure BDA0000069071400000151
By table 5 as seen:
Red reactive dye composition of the present invention has good sun-resistant fastness.

Claims (10)

1. red reactive dye composition, this dye composite contain the dye composition of one or more general formulas (1) expression and the dye composition of one or more general formulas (2) expression:
General formula (1)
In the formula:
Z 1For-CH 2CH 2OSO 3M or-CH=CH 2
R 1And R 2Be H, C independently respectively 1-C 4Alkyl, C 1-C 4Alkoxyl group or-SO 3M;
R 3Be H or C 1-C 4Alkyl;
R 4Be H or C 1-C 4Alkyl;
X is Cl, F or NHCN;
M is H or alkali metal cation;
P is 0 or 1;
Figure FDA0000069071390000012
General formula (2)
In the formula:
Z 2For-CH 2CH 2OSO 3M or-CH=CH 2
R 5And R 6Be H, C independently respectively 1-C 4Alkyl, C 1-C 4Alkoxyl group or sulfonic group;
R 7Be H or C 1-C 4Alkyl;
R 8And R 9Be H, C independently respectively 1-C 4Alkyl, C 1-C 4Alkoxyl group or sulfonic group;
M is H or alkali metal cation.
2. the described red reactive dye composition of claim 1, it is characterized in that, the dye composition of one or more general formulas (1) expression: the weight ratio of the dye composition of one or more general formulas (2) expression is 90~10: 10~90, be preferably 70~30: 30~70, more preferably 60~40: 40~60.
3. the described red reactive dye composition of claim 1 is characterized in that, in the general formula (1)-and SO 2Z 1Group is positioned on the benzene nucleus
Figure FDA0000069071390000021
The contraposition of group or a position; R 1And R 2Be separately located on the benzene nucleus respectively
Figure FDA0000069071390000022
The ortho position of group, contraposition or a position.
4. the described red reactive dye composition of claim 1, it is characterized in that, what link to each other with diazo left side in the general formula (1) is benzene nucleus or naphthalene nuclear derivatives, link to each other with diazo left side in the general formula (1) be benzene nucleus the time, p equals 0, when link to each other with diazo left side in the general formula (1) examine for naphthalene the time, when p=1, sulfonic acid group is positioned at 5 that naphthalene is examined.
5. the described red reactive dye composition of claim 1 is characterized in that, link to each other with general formula (1) diazo left side be benzene nucleus the time, R 4Group is positioned on the benzene nucleus-contraposition or a position of N=N-group; Link to each other with general formula (1) diazo left side examine for naphthalene the time, R 4Group is positioned at 4,5,6 or 7 on the naphthalene nuclear.
6. the described red reactive dye composition of claim 1 is characterized in that, the middle left side of general formula (2)-SO 2Z 2Group is positioned on the benzene nucleus-ortho position, a position or the contraposition of N=N-group; The R in left side in the general formula (2) 5And R 6Group is separately located in respectively on the benzene nucleus-ortho position, a position or the contraposition of N=N-group.
7. the described red reactive dye composition of claim 1 is characterized in that, general formula (2) right side-SO 3The M group is positioned on the benzene nucleus
Figure FDA0000069071390000031
The contraposition of group, a position or ortho position; The R on right side in the general formula (2) 8And R 9Group is separately located on the benzene nucleus respectively The contraposition of group, a position or ortho position.
8. the described red reactive dye composition of claim 1~7 is characterized in that, the dye composition of general formula (1) expression is:
Figure FDA0000069071390000033
Dyestuff 1-1
Figure FDA0000069071390000034
Dyestuff 1-2
Figure FDA0000069071390000041
Dyestuff 1-3
Figure FDA0000069071390000042
Dyestuff I-4
Figure FDA0000069071390000043
Dyestuff I-5
Figure FDA0000069071390000051
Dyestuff I-6
Figure FDA0000069071390000052
Dyestuff I-7 or
Dyestuff I-8.
9. the described red reactive dye composition of claim 1~7 is characterized in that, the dye composition of general formula (2) expression is:
Figure FDA0000069071390000061
Dyestuff 2-1
Figure FDA0000069071390000062
Dyestuff 2-2
Figure FDA0000069071390000063
Dyestuff 2-3
Dyestuff 2-4
Figure FDA0000069071390000072
Dyestuff 2-5
Figure FDA0000069071390000073
Dyestuff 2-6
Figure FDA0000069071390000081
Dyestuff 2-7 or
Figure FDA0000069071390000082
Dyestuff 2-8.
In the claim 1~9 each described red reactive dye composition in the application of the dyeing aspect of hydroxyl and/or formamido-material, particularly filamentary material.
CN2011101650056A 2011-06-17 2011-06-17 Red active dye composition and dyeing application thereof in fibers Pending CN102286219A (en)

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103554976A (en) * 2013-09-29 2014-02-05 天津德凯化工股份有限公司 Red reactive dye and preparation method thereof
CN104164097A (en) * 2014-07-29 2014-11-26 浙江瑞华化工有限公司 Active deep blue dye composition and high-solubility active deep blue dye, and preparation method and applications of high-solubility active deep blue dye
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
CN105385192A (en) * 2015-11-30 2016-03-09 无锡新德印染制品有限公司 Green and environment-friendly red reactive dye composite
TWI583743B (en) * 2012-06-26 2017-05-21 臺灣永光化學工業股份有限公司 Novel reactive dye
CN108727867A (en) * 2018-05-18 2018-11-02 无锡润新染料有限公司 A kind of active red SPE dyestuffs and its clean synthetic method
CN111925666A (en) * 2020-08-20 2020-11-13 浙江亿得新材料股份有限公司 High-solarization red reactive dye and preparation method thereof
CN116004032A (en) * 2022-12-30 2023-04-25 上海雅运新材料有限公司 A kind of red dye compound and its synthesis method and application

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CN1861696A (en) * 2006-06-19 2006-11-15 湖北华丽染料工业有限公司 Ozo dye mixture
CN101935466A (en) * 2010-08-26 2011-01-05 浙江科永化工有限公司 A kind of reactive red dye composition

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Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI583743B (en) * 2012-06-26 2017-05-21 臺灣永光化學工業股份有限公司 Novel reactive dye
CN103554976A (en) * 2013-09-29 2014-02-05 天津德凯化工股份有限公司 Red reactive dye and preparation method thereof
CN104164097A (en) * 2014-07-29 2014-11-26 浙江瑞华化工有限公司 Active deep blue dye composition and high-solubility active deep blue dye, and preparation method and applications of high-solubility active deep blue dye
CN104164097B (en) * 2014-07-29 2016-02-03 浙江瑞华化工有限公司 Reactive dark blue dye composite, high-dissolvability reactive dark blue dyestuff and its preparation method and application
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
CN105385192A (en) * 2015-11-30 2016-03-09 无锡新德印染制品有限公司 Green and environment-friendly red reactive dye composite
CN108727867A (en) * 2018-05-18 2018-11-02 无锡润新染料有限公司 A kind of active red SPE dyestuffs and its clean synthetic method
CN111925666A (en) * 2020-08-20 2020-11-13 浙江亿得新材料股份有限公司 High-solarization red reactive dye and preparation method thereof
CN116004032A (en) * 2022-12-30 2023-04-25 上海雅运新材料有限公司 A kind of red dye compound and its synthesis method and application

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