CN102277011A - Red reactive dye composition and application thereof to fiber dyeing - Google Patents
Red reactive dye composition and application thereof to fiber dyeing Download PDFInfo
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- CN102277011A CN102277011A CN2011101652009A CN201110165200A CN102277011A CN 102277011 A CN102277011 A CN 102277011A CN 2011101652009 A CN2011101652009 A CN 2011101652009A CN 201110165200 A CN201110165200 A CN 201110165200A CN 102277011 A CN102277011 A CN 102277011A
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- 0 Cc1nc(N(*)c2ccccc2)nc(Nc2cc(*)cc(cc3*)c2c(O)c3N=Nc2ccccc2)n1 Chemical compound Cc1nc(N(*)c2ccccc2)nc(Nc2cc(*)cc(cc3*)c2c(O)c3N=Nc2ccccc2)n1 0.000 description 2
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Abstract
The invention provides a red reactive dye composition and application thereof to dyeing. The dye composition contains one or more dye compounds shown in a general formula (1) and one or more dye compounds shown in a general formula (2). The red reactive dye composition has excellent application performance in wool dyeing. The red reactive dye composition has good color fastness. The general formula (1) and the general formula (2) are shown in the specification.
Description
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.
WO 00/63298 (2000) patent that Dystar company delivers has also been used this dyestuff.
Said structure is the representative structure of the dyestuff of general formula (2) expression.
Another red reactive dyes that the present invention relates to is the dyestuff shown in the general formula (1).The structure of this kind at first is published in the patent JP 58204051 (1983) that Hoechst company delivers.Associated companies is delivered the patent that relates to this kind in succession later on.These patents are:
US?5250670(1993)(Hoechst)
US?5665124(1997)(Bayer)
US?5779739(1998)(Hoechst)
In view of this kind still has unsatisfactory application performance defective, Krairi Anter Finanace (BVI) Co., Ltd. delivers in succession and relates to each isomer of this kind self mixture to improve patent---the CN 1503828 (2004) and the US7091328 (2007) of application performance.
Each major company of the world improves this kind application performance with composition mixture or composition mode again, delivers numerous following patents:
JP?8259831(1996)(Hoechst)
US?5980590(1999)(Dystar)
US?6090164(2000)(Dystar)
US?6136045(2000)(Dystar)
EP?0957137(1999)(Dystar)
US?6916350(2005)(Dystar)
In the research of the application performance of the dyestuff that improves general formula of the present invention (1) expression, 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 also obviously be better than JP 8259831 (1996) (Hoechst) and the reactive dye compositions that (Dystar) provided of US 5980590 (1999).
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.
The tint applications data presentation, 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 5980590 (1999) (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.
General formula (1)
In the formula:
Z
1And Z
2Be independently-CH respectively
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
4And R
5Be H, C independently respectively
1-C
4Alkyl, C
1-C
4Alkoxyl group or-SO
3M;
R
3Be H or C
1-C
4Alkyl;
X is C1, F or NHCN;
M is H or alkali metal cation;
General formula (2)
In the formula:
Z
3For-CH
2CH
2OSO
3M or-CH=CH
2
R
6And R
7Be H, C independently respectively
1-C
4Alkyl, C
1-C
4Alkoxyl group or sulfonic group;
R
8Be H or C
1-C
4Alkyl;
R
9And R
10Be 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, more preferably 60～40: 40～60.
One preferred embodiment in, in the general formula (1)-SO
2Z
1Group is positioned on the benzene nucleus
The contraposition of group or a position; In the general formula (1)-SO
2Z
2Group is positioned on the benzene nucleus-contraposition or a position of N=N-group.
Another preferred embodiment in, the R in the general formula (1)
1And R
2Group is separately located on the benzene nucleus respectively
The contraposition of group, a position or ortho position; R in the general formula (1)
4And R
5Group is separately located in respectively on the benzene nucleus-contraposition, a position or the ortho position of N=N-group.
One preferred embodiment in, general formula (2) right side-SO
3The M group is positioned on the benzene nucleus
The contraposition of group, a position or ortho position; On the left of in the general formula (2)-SO
2Z
3Group, be positioned on the benzene nucleus-the N=N-group between position or contraposition
Another preferred embodiment in, the R in left side in the general formula (2)
6And R
7Group is separately located in respectively on the benzene nucleus-ortho position, a position or the contraposition of N=N-group; The R on right side in the general formula (2)
9And R
10Group is separately located on the benzene nucleus respectively
The contraposition of group, a position or ortho position.
The dye composition of general formula (1) expression for example comprises following example:
Dyestuff 1-1
Dyestuff 1-2
Dyestuff 1-3
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 example:
Dyestuff 2-1
Dyestuff 2-2
Dyestuff 2-3
Dyestuff 2-4
Dyestuff 2-5
Dyestuff 2-6
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 dye structure and the synthetic method thereof of general formula (1) expression, and they are:
US?5250670(1993)(Hoechst)
US?5292870(1994)(ICI)
US?5665124(1997)(Bayer)
CN 1503828 (2004) (Krairi Anter Finanace (BVI) Co., Ltd.)
US?7091328(2006)(Clariant?Finance(BVI)Limited)
EP?0094055(1983)(Hoechst)
US?5980590(1999)(Dystar)
The dye structure and the synthetic method thereof of general formula (2) expression are 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, salt tolerant alkali solubility: take by weighing a certain amount of dyestuff, in the 250mL Erlenmeyer flask, add distilled water 65mL and be configured to dye liquor.Erlenmeyer flask is put in the vibration dyeing machinery, behind 60 ℃ of insulation 5min, adds 200g/L Na
2SO
425mL continues to add 200g/LNa behind the insulation 5min
2CO
310mL carries out suction filtration (during suction filtration, pressure 0.075Mpa, 5A qualitative filter paper) after being incubated 30min again, observes the filter paper residual condition.Reduce dye strength (G/L), no dyestuff is residual on filter paper, and the dye strength (G/L) of this moment is the salt tolerant alkali dissolution of dyestuff.
3, colour fastness to perspiration test: measure by international standard ISO 105-E04.
4, fastness to soaping test: measure by international standard ISO 105-C10.
5, color fastness to water test: measure by international standard ISO 105-E01.
6, 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 1-3+30% dyestuff 2-3 |
| 5 | E | 50% dyestuff 1-3+50% dyestuff 2-3 |
| 6 | F | 30% dyestuff 1-3+70% dyestuff 2-3 |
| 7 | Reference X | 100% dyestuff 1-1 |
| 8 | Reference Y | 100% dyestuff 2-1 |
| 9 | Reference Z | 50% dyestuff 1-1+50% reactive red C.I.198 |
* reference Z is (Dystar) cited embodiment of US 5980590 (1999).
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
By table 2 as seen:
1) red reactive dye composition of the present invention is used for woolen dyedly, demonstrates excellent enhancing rate.
2) red reactive dye composition of the present invention at woolen dyed enhancing rate measured value, all apparently higher than its weighted mean of forming dyestuff, embodies the effect of compound synergic.
3) red reactive dye composition of the present invention is in woolen dyed enhancing rate, apparently higher than (Dystar) conventional dye combinations of US 5980590 (1999).Consult the dyeing enhancing rate data of dye composite B and dye composite reference Z in the table 2.
Embodiment 2
The test of salt tolerant alkali solubility
Measure the salt tolerant alkali solubility of following dyestuff as stated above, test result is recorded in the table 3
Table 3
By table 4 as seen:
The salt tolerant alkali solubility of red reactive dye composition of the present invention is better than reference dye composite Z, thereby has good level dyeing performance.
Embodiment 3
Colour fastness to perspiration
Measure the colour fastness to perspiration of following dyestuff as stated above, test result is recorded in the table 4
Table 4
By table 4 as seen:
Red reactive dye composition of the present invention has good fastness to perspiration.
Embodiment 4
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 5
Table 5
By table 5 as seen:
Red reactive dye composition of the present invention has good fastness to soaping and color fastness to water.
Embodiment 5
Sun-resistant fastness
Measure the sun-resistant fastness of following dyestuff as stated above, test result is recorded in the table 6
Table 6
By table 6 as seen:
Red reactive dye composition of the present invention still has good sun-resistant fastness.
Claims (9)
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
1And Z
2Be independently-CH respectively
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
4And R
5Be H, C independently respectively
1-C
4Alkyl, C
1-C
4Alkoxyl group or-SO
3M;
R
3Be H or C
1-C
4Alkyl;
X is C1, F or NHCN;
M is H or alkali metal cation;
General formula (2)
In the formula:
Z
3For-CH
2CH
2OSO
3M or-CH=CH
2
R
6And R
7Be H, C independently respectively
1-C
4Alkyl, C
1-C
4Alkoxyl group or sulfonic group;
R
8Be H or C
1-C
4Alkyl;
R
9And R
10Be 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, its characteristic be, in the general formula (1)-and SO
2Z
1Group is positioned on the benzene nucleus
The contraposition of group or a position; In the general formula (1)-SO
2Z
2Group is positioned on the benzene nucleus-contraposition or a position of N=N-group.
4. the described red reactive dye composition of claim 1 is characterized in that the R in the general formula (1)
1And R
2Group is separately located on the benzene nucleus respectively
The contraposition of group, a position or ortho position; R in the general formula (1)
4And R
5Group is separately located in respectively on the benzene nucleus-contraposition, a position or the ortho position of N=N-group.
5. 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
The contraposition of group, a position or ortho position; On the left of in the general formula (2)-SO
2Z
3Group, be positioned on the benzene nucleus-the N=N-group between position or contraposition.
6. the described red reactive dye composition of claim 1 is characterized in that, the R in left side in the general formula (2)
6And R
7Group is separately located in respectively on the benzene nucleus-ortho position, a position or the contraposition of N=N-group; The R on right side in the general formula (2)
9And R
10Group is separately located on the benzene nucleus respectively
The contraposition of group, a position or ortho position.
7. the described red reactive dye composition of claim 1～6 is characterized in that, the dye composition of general formula (1) expression is:
Dyestuff 1-1
Dyestuff 1-2
Dyestuff 1-3
Dyestuff I-4
Dyestuff I-5
Dyestuff I-6
Dyestuff I-7 or
Dyestuff I-8.
8. the described red reactive dye composition of claim 1～6 is characterized in that, the dye composition of general formula (2) expression is:
Dyestuff 2-1
Dyestuff 2-2
Dyestuff 2-3
Dyestuff 2-4
Dyestuff 2-5
Dyestuff 2-6
Dyestuff 2-7 or
Dyestuff 2-8.
In the claim 1～8 each described red reactive dye composition in the application of the dyeing aspect of hydroxyl and/or formamido-material, particularly filamentary material.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011101652009A CN102277011A (en) | 2011-06-17 | 2011-06-17 | Red reactive dye composition and application thereof to fiber dyeing |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011101652009A CN102277011A (en) | 2011-06-17 | 2011-06-17 | Red reactive dye composition and application thereof to fiber dyeing |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN102277011A true CN102277011A (en) | 2011-12-14 |
Family
ID=45102766
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2011101652009A Pending CN102277011A (en) | 2011-06-17 | 2011-06-17 | Red reactive dye composition and application thereof to fiber dyeing |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN102277011A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103554993A (en) * | 2013-11-19 | 2014-02-05 | 上海雅运纺织化工股份有限公司 | Red active dye composition and dyeing application thereof to fibers |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58204051A (en) * | 1982-05-12 | 1983-11-28 | ヘキスト・アクチエンゲゼルシヤフト | Monoazo compound, manufacture and use as dye |
| EP0211328A2 (en) * | 1985-08-05 | 1987-02-25 | Hoechst Aktiengesellschaft | Process for the level dyeing of mixtures of cotton with modal fibres |
| JPH08259827A (en) * | 1995-03-21 | 1996-10-08 | Bayer Ag | Monoazo reactive dye |
| US5665124A (en) * | 1994-10-28 | 1997-09-09 | Bayer Aktiengesellschaft | Process for dyeing and printing materials containing hydroxyl and/or carboxamide groups |
| US5779739A (en) * | 1995-03-30 | 1998-07-14 | Hoechst Aktiengesellschaft | Dye mixtures of fiber-reactive azo dyes and their use for dyeing hydroxy-and/or carboxamido-containing fiber material |
| CN1425045A (en) * | 2000-04-08 | 2003-06-18 | 德意志戴斯达纺织品及染料两合公司 | Dye mixture of water-soluble fiber-reactive azo dyes, method for production and use thereof |
| CN1503828A (en) * | 2001-04-20 | 2004-06-09 | 克莱里安特财务(Bvi)有限公司 | Fiber-reactive mono-Azo dyes |
-
2011
- 2011-06-17 CN CN2011101652009A patent/CN102277011A/en active Pending
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58204051A (en) * | 1982-05-12 | 1983-11-28 | ヘキスト・アクチエンゲゼルシヤフト | Monoazo compound, manufacture and use as dye |
| EP0211328A2 (en) * | 1985-08-05 | 1987-02-25 | Hoechst Aktiengesellschaft | Process for the level dyeing of mixtures of cotton with modal fibres |
| US5665124A (en) * | 1994-10-28 | 1997-09-09 | Bayer Aktiengesellschaft | Process for dyeing and printing materials containing hydroxyl and/or carboxamide groups |
| JPH08259827A (en) * | 1995-03-21 | 1996-10-08 | Bayer Ag | Monoazo reactive dye |
| US5779739A (en) * | 1995-03-30 | 1998-07-14 | Hoechst Aktiengesellschaft | Dye mixtures of fiber-reactive azo dyes and their use for dyeing hydroxy-and/or carboxamido-containing fiber material |
| CN1425045A (en) * | 2000-04-08 | 2003-06-18 | 德意志戴斯达纺织品及染料两合公司 | Dye mixture of water-soluble fiber-reactive azo dyes, method for production and use thereof |
| CN1503828A (en) * | 2001-04-20 | 2004-06-09 | 克莱里安特财务(Bvi)有限公司 | Fiber-reactive mono-Azo dyes |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103554993A (en) * | 2013-11-19 | 2014-02-05 | 上海雅运纺织化工股份有限公司 | Red active dye composition and dyeing application thereof to fibers |
| CN103554993B (en) * | 2013-11-19 | 2016-05-11 | 上海雅运纺织化工股份有限公司 | Red reactive dye composition and the tint applications on fiber thereof |
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Free format text: CORRECT: APPLICANT; FROM: YANYUN TEXTILE CHEMICAL CO., LTD., SHANGHAI TO: SHANGHAI ARGUS TEXTILE CHEMICAL CO., LTD. |
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| C53 | Correction of patent of invention or patent application | ||
| CB02 | Change of applicant information |
Address after: 200231 Shanghai city Xuhui District Yindu Road No. 388 building 16 room 275-278 Applicant after: Shanghai Argus Textile Chemical Co., Ltd. Address before: Five road 201812 Shanghai city Jiading District Jiangqiao Fengbang Po Garden No. 301 Applicant before: Shanghai Argus Textile Chemical Co., Ltd. |
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| C12 | Rejection of a patent application after its publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20111214 |