CN102485802A - Navy blue reactive dye composition and its application in fiber dyeing - Google Patents

Navy blue reactive dye composition and its application in fiber dyeing Download PDF

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CN102485802A
CN102485802A CN201010571175XA CN201010571175A CN102485802A CN 102485802 A CN102485802 A CN 102485802A CN 201010571175X A CN201010571175X A CN 201010571175XA CN 201010571175 A CN201010571175 A CN 201010571175A CN 102485802 A CN102485802 A CN 102485802A
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group
general formula
dye composition
navy blue
alkyl
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CN102485802B (en
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郑怡华
顾喆栋
曾建平
谢兵
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Shanghai Argus Textile Chemical Co., Ltd.
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SHANGHAI ARGUS FINE CHEMICAL CO Ltd
SHANGHAI ARGUS TEXTILE CHEMICAL CO Ltd
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Abstract

The invention provides a navy blue reactive dye composition and its application in fiber dyeing. The dye composition comprises one or several of dye compounds represented in general formula (1), one or several of dye compounds represented in general formula (2-A) or (2-B) and one or several of dye compounds represented in general formula (3). The navy blue reactive dye composition of the invention has excellent dyeing performance and color fastness, as well as excellent compatibility when dyed with other common red and yellow reactive dyes.

Description

Navy blue 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 navy blue 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 a kind of navy blue reactive dye composition,, thereby significantly improve its tint applications performance and dyefastness through compound synergic.
One of component of the navy blue reactive dye composition that the present invention relates to is a kind of copper-containing metal De Jia Za class (Formazan) dyestuff.
Hoechst company in 1986 delivers patent US4607098 and discloses following structure De Jia Za type reactive dyestuffs and compound method thereof.
Figure BDA0000035867100000011
This dye structure is different from Hoechst company delivers the disclosed Jia Za of patent US4336190 type reactive dyestuffs in nineteen eighty-two structure.
Figure BDA0000035867100000021
The structure difference of dyestuff m and dyestuff n is the difference that it becomes number of rings.The former is the dicyclo type, and the latter then is a tricyclic.This patent points out that dicyclo Xing Jia Za type reactive dyestuffs have good tint applications performance.Commendable is that the synthetic cost of dyestuff m is far below dyestuff n.
Tricyclic first Za type reactive dyestuffs have received the attention of dyestuff circle always since finding.Numerous research shows , Jia Za type reactive dyestuffs, and is beautiful in colour, is far superior to conventional azo-type reactive dyestuffs.Compare the consistency that , Jia Za type reactive dyestuffs have better and other color and luster dyestuffs dye together with triphendioxazine type reactive dyestuffs with anthraquinone type.
The further development research of dicyclo Xing Jia Za type reactive dyestuffs is not received due attention.
Last century Mo, Korea S Kyung-In Synthetic Corporation delivered the new structure that patent US5858026 discloses dicyclo Xing Jia Za type reactive dyestuffs in 1999.Its general formula is:
Figure BDA0000035867100000022
Korean Patent KR20030094982 and KR20040031792 disclose dicyclo Xing Jia Za type reactive dye compositions.This binomial patent report, dicyclo Xing Jia Za type reactive dyestuffs and tricyclic Jia Za type reactive dyestuffs are pieced together mixed, or the inner diverse structure assembly of dicyclo Xing Jia Za type reactive dyestuffs is mixed, can further improve application performance and some dyefastness of dyestuff.
Up to now, the further further investigation to dicyclo Xing Jia Za type reactive dyestuffs is not seen in patent report as yet.
The inventor through a large amount of verification experimental verifications think behind the related content announced of Korean Patent KR 20030094982 and KR 20040031792; Dicyclo Xing Jia Za type reactive dyestuffs mixed dicyclo Xing Jia Za type reactive dyestuffs of inner isomery assembly and tricyclic Jia Za type reactive dyestuffs are pieced together mixed, really can improve certain tint applications performance in varying degrees.
But practice shows, reactive dye compositions that Korean Patent KR20030094982 and KR20040031792 provide or miscellany, and as the commercial dye kind, the real difficulty of its overall application performance satisfies the requirement of current printing and dyeing industry.
The inventor is through research trial in earnest; Find pleasantly surprisedly; In the miscellany that general formula (1) dyestuff and general formula (2-A) dyestuff and/or general formula (2-B) dyestuff are formed; The disazo dyes kind of adding a kind of copper metal complex of the same type is pieced together mixed as the 3rd component, can obtain unexpected pleasurable effect.
The structure of the disazo dyes kind of the copper-containing metal that the inventor adopts is shown in general formula (3).It is blue to grey black that the color and luster of this type dyestuff is.
The time that this type dyestuff is disclosed in patent early.The patent of at first delivering is:
GB?1162144(1969)(Hoechst)、DE?1544538(1970)(Hoechst)。Dyestuff is good at the light fastness excellence.Hewlett-Packard Commpany delivers patent GB 2318798 (1997) and at first this type dyestuff is used the dye component as jetting ink.Other patent is also announced that this reactive dyestuffs kind can piece together to mix with matching stain, substantive dyestuff and is made jetting ink.
There is defective in general formula (3) though dyestuff has excellent dyefastness in dyeing keratin-fiber, for example level-dyeing property and lifting rate remain to be improved.Bright and lustrous degree has much room for improvement.
The inventor's test practice shows; Of the present inventionly piece together the mixed navy blue reactive dye composition of forming by a certain percentage by dye composition shown in dye composition shown in dye composition shown in one or more general formulas (1), one or more general formulas (2-A) or the general formula (2-B) and one or more general formulas (3); Take in the length of its component dyestuff concurrently, its application performance significantly increases and improves.
Navy blue reactive dye composition of the present invention is with low cost, have excellent dyefastness, adjustable coloured light and good lifting rate, degree of fixation and other color and luster reactive dyestuffs are with the consistency of dying; Therefore, has wide development space as commercial dye.
The assembly of the copper-containing metal bi-azo active dye shown in the general formula (3) mixes data, can consult following patent:
EP?0668328(1995)(Hoechst)
CN?1444635(2003)(Dystar)
CN?1626582(2005)(Dystar)
CN 101374913 (2009) (Everlight USA, Inc.)
The data of relevant prompting ternary mixture provided by the present invention or compsn is not seen in the patent report.
Summary of the invention
The inventor is surprised to find the blue active dye compound of the blue active dye compound, one or more general formulas (2-A) or general formula (2-B) expression that contain one or more general formulas (1) expression and the navy dye composite of the black-and-blue reactive dye compound that one or more general formulas (3) are represented and has very excellent dyeing behavior and each item fastness through experimental study.
What be worth proposition is; The tint applications performance of navy blue reactive dye composition of the present invention and each item dyefastness; Take in the length that it forms the characteristic of dyestuff concurrently, remedy some defective that it forms dyestuff, navy blue reactive dye composition of the present invention; Not only keep its good dye fastness and dye of forming dyestuff, and tangible improvement all takes place in its level-dyeing property, lifting rate, consistency.Navy blue reactive dye composition of the present invention, low preparation cost can be formed three primary colors with conventional red, yellow dye and use.Can predict, navy blue reactive dye composition of the present invention has wide prospect in industrial application.
Navy blue reactive dye composition provided by the invention comprises the dye composition of dye composition, one or more general formulas (2-A) or general formula (2-B) expression of one or more general formulas of certain proportion blended (1) expression, and the dye composition of one or more general formulas (3) expression:
Figure BDA0000035867100000041
In the formula:
M is H, alkali metal cation or ammonium ion;
Y 1Be CH 2CH 2OSO 3M or-CH=CH 2
X is Cl or F;
p 1, q 1, r 1Be respectively 0 or 1 independently;
R 1Be H or C 1-C 4Alkyl;
R 11And R 12Be H, C independently respectively 1-C 4Alkyl, C 1-C 4Alkoxyl group, Cl or-SO 3M;
Figure BDA0000035867100000051
In the formula:
M is H, alkali metal cation or ammonium ion;
Y 2For-CH 2CH 2OSO 3M or-CH=CH 2
X is Cl or F;
p 2, q 2And r 2Be respectively 0 or 1 independently;
R 2Be H or C 1-C 4Alkyl;
R 4Be H, C 1-C 4Alkyl, C 1-C 4Alkoxyl group, halogen or hydroxyl;
R 13And R 14Be H, C independently respectively 1-C 4Alkyl, C 1-C 4Alkoxyl group, sulfonic group or Cl.
In the formula:
M is H, alkali metal cation or ammonium ion;
Y 3For-CH 2CH 2OSO 3M or-CH=CH 2
X is Cl or F;
p 3And q 3Be respectively 0 or 1 independently;
R 3Be H or C 1-C 4Alkyl;
R 5Be H, C 1-C 4Alkyl, C 1-C 4Alkoxyl group, halogen or hydroxyl;
R 15And R 16Be H, C independently respectively 1-C 4Alkyl, C 1-C 4Alkoxyl group, sulfonic group or Cl.
Figure BDA0000035867100000062
In the formula:
M is H, alkali metal cation or ammonium ion;
Y 4For-CH 2CH 2OSO 3M or-CH=CH 2
R 6Be H, C 1-C 4Alkyl, C 1-C 4Alkoxyl group, sulfonic group or Cl;
R 7Be H, C 1-C 4Alkyl or carboxyl;
R 8For H, sulfonic group or-SO 2Y 4Group;
R 9And R 10Be H, C independently respectively 1-C 4Alkyl, C 1-C 4Alkoxyl group, sulfonic group or Cl.
The present invention also provides the application of above-mentioned navy blue reactive dye composition at the dyeing aspect of hydroxyl and/or formamido-material, particularly filamentary material.
The dyeing behavior of navy blue reactive dye composition of the present invention all has clear improvement and improves.Dye composite is synthetic with low cost.Dye composite is taken in the length of its component concurrently, and not only lifting rate and consistency have clear improvement, and can also guard excellent fastness ability.
The practical implementation method
The dye composition that comprises dye composition, one or more general formulas (2-A) or general formula (2-B) expression of one or more general formulas (1) expression in the dye composite of the present invention, and the dye composition of one or more general formulas (3) expression.
In dye composite of the present invention; The weight ratio of the dye composition (being called for short dyestuff 2-A) of the dye composition of one or more general formulas (1) expression (being called for short dyestuff 1) and one or more general formulas (2-A) expression or the dye composition (being called for short dyestuff 2-B) of general formula (2-B) expression and the dye composition (being called for short dyestuff 3) that one or more general formulas (3) are represented is 5~30: 20~50: 30~70; Be preferably 10~30: 20~40: 40~60, more preferably 10~25: 25~40: 45~55.
One preferred embodiment in, general formula (1), general formula (2-A) and general formula (2-B) left side-SO 3The M group is worked as p 1, p 2, p 3Equal at 1 o'clock, be positioned on the benzene nucleus
Figure BDA0000035867100000071
Position or contraposition between group.General formula (1), general formula (2-A) and general formula (2-B) middle part-SO 3The M group is worked as r 1, r 2Equal at 1 o'clock, be positioned on the benzene nucleus-the N=N-group between position or contraposition.
Another preferred embodiment in, general formula (1), general formula (2-A) and general formula (2-B) downside-SO 3The M group is worked as q 1, q 2, q 3Equal at 1 o'clock, be positioned on the benzene nucleus
Figure BDA0000035867100000072
The contraposition of group, a position or ortho position; The R of general formula (2-A) and general formula (2-B) downside 4And R 5, be separately located on the benzene nucleus respectively
Figure BDA0000035867100000073
The contraposition of group, a position or ortho position.
One preferred embodiment in, general formula (1), general formula (2-A), general formula (2-B) right side-SO 2Y 1Group ,-SO 2Y 2Group and-SO 2Y 3Group is separately located on the benzene nucleus respectively Group or Group or
Figure BDA0000035867100000076
The contraposition of group, a position or ortho position.The R on general formula (1), general formula (2-A), general formula (2-B) right side 11, R 12, R 13, R 14, R 15And R 16Group is separately located on the benzene nucleus respectively
Figure BDA0000035867100000077
Group or Group or
Figure BDA0000035867100000079
The contraposition of group, a position or ortho position.
Another preferred embodiment in, general formula (3) left side-SO 2Y 4Group is positioned on the benzene nucleus-the N=N-group between position or contraposition; The R in general formula (3) left side 6Group, be positioned on the benzene nucleus-the N=N-group between the ortho position of position or be positioned on the benzene nucleus-O-group.
Among the present invention, the dye composition of general formula (1) expression for example comprises following instance:
Figure BDA0000035867100000081
Figure BDA0000035867100000101
Among the present invention, the dye composition of general formula (2-A) expression for example comprises following instance:
Figure BDA0000035867100000102
Figure BDA0000035867100000111
Figure BDA0000035867100000121
Figure BDA0000035867100000131
Among the present invention, the dye composition of general formula (2-B) expression for example comprises following instance:
Figure BDA0000035867100000151
Among the present invention, the dye composition of general formula (3) expression for example comprises following instance:
Figure BDA0000035867100000152
Figure BDA0000035867100000161
Figure BDA0000035867100000171
General formula (1), general formula (2-A) and the reactive dye compound of (2-B) representing are known dye.
The structure and the compound method of the reactive dye compound of general formula (1) expression, see following patent:
US?4607098(1986)(Hoechst)
US?5858026(1999)(Kyung-In?Synthetic?Corp)
KR?20030094982
KR20040031792
The general formula (2-A) and (2-B) structure and the compound method of reactive dye compound of expression, see following patent:
CN?1422907(2003)(Dystar)
CN?1247707(2006)(Dysrtar)
The full content of above-mentioned document is referred among the present invention.
The structure and the compound method of the reactive dye compound of general formula (3) expression, see following patent:
GB?1162144(1969)(Hoechst)
DE?1544538(1970)(Hoechst)
Navy blue 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, 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 be made up of general formula (1) dyestuff of above-mentioned weight ratio and general formula (2) dyestuff and general formula (3) dyestuff.
The preparation method of navy blue reactive dye composition of the present invention comprises above-mentioned general formula (1) dyestuff and general formula (2) dyestuff and general formula (3) dyestuff is mixed 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 and general formula (3) 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.
Navy blue 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-; Be more especially filamentary material, for example cotton, flax and hemp fibre, and Mierocrystalline cellulose and regenerated cellulose, polyester or polyamide fiber material etc.
Navy blue 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
Each item testing method of embodiment
Each item performance of present embodiment is tested by following each item testing method
1, lifting rate test: pure cotton fabric is pressed 60 ℃ of constant temperature technology dyeing of reactive dyestuffs, and dyeing concentration is 0.5%, 1%, 2%, 4%, 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.
2, just dye the test of rate and degree of exhaustion: the dye liquor preparation, press 60 ℃ of constant temperature technology dyeing of reactive dyestuffs.Respectively before adding alkali with on dye and finish to take a sample before the soap boiling, measure the absorbance of dyeing residual liquid, with dye liquor absorbance before the dyeing relatively.
Just dye rate=(1-adds the absorbance of the preceding dye liquor of absorbance/dyeing of the preceding dye liquor of alkali) * 100%
Degree of exhaustion=(1-soap before the absorbance of the preceding dye liquor of absorbance/dyeing of dye liquor) * 100%
3, move the test of staining index MI value: two onesize A, B cloth specimen input are added with in the dye bath of dyestuff, sodium sulfate; Behind 60 ℃ of dyeing 30min; Take out the B cloth specimen; The B cloth specimen is put in the blank dye bath that only contains sodium sulfate, put into onesize calico C simultaneously, continue to add yellow soda ash fixation 60min behind dyeing (move and dye) 20min.The apparent dye yield (K/S) that compares B cloth specimen and C cloth specimen.
Move apparent dye yield (K/S) * 100% of apparent dye yield (the K/S)/B cloth specimen of staining index MI=C cloth specimen
4, colour fastness to perspiration test: measure by international standard ISO 105-E04.
5, fastness to soaping test: measure by international standard ISO 105-C10.
6, color fastness to water test: measure by international standard ISO 105-E01.
7, 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 navy blue reactive dye compositions 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
Figure BDA0000035867100000191
* reference X is Korean Patent KR20030094982 and the cited embodiment of KR20040031792
* reference Y is (Dystar) cited embodiment of CN 1444635 (2003)
Embodiment 1
The coloured light of navy blue reactive dye composition of the present invention
The dyestuff color and luster of general formula (1) and general formula (2-A) or general formula (2-B) expression is sky blue and color and luster is more shallow, can not be used as the three primary colors blue color component, and the dyestuff color and luster of general formula (3) expression is black-and-blue.
The coloured light of reactive dye compositions of the present invention can be adjusted the ratio of general formula (1) dyestuff and general formula (2-A) dyestuff and/or general formula (2-B) dyestuff and general formula (3) dyestuff as required; Thereby make mixture constitute the three primary colors combination with other redness, yellow dyes effectively, improve its actual application value.
Embodiment 2
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 2
Table 2
Figure BDA0000035867100000211
Visible by table 2:
Navy blue reactive dye composition of the present invention is compared with the reference dyestuff, and its lifting rate increases significantly.
Embodiment 3
Just dying rate and degree of exhaustion measures
Measure the first rate and the degree of exhaustion of dying of following dyestuff as stated above, test result is recorded in the table 3
Table 3
Figure BDA0000035867100000212
Visible by table 3:
1) the first rate of dying of navy blue reactive dye composition of the present invention is compared with the reference dyestuff; All make moderate progress, reduced the first rate of dying of reference dyestuff, avoided dying on the dyestuff the too fast look flower phenomenon that causes; Improved level-dyeing property, shown, red yellow good consistency when dying with conventional three primary colors;
2) navy blue reactive dye composition of the present invention has still kept higher degree of exhaustion.
Embodiment 4
Moving staining index measures
Measure the staining index that moves of following dyestuff as stated above, test result is recorded in the table 4
Table 4
Figure BDA0000035867100000221
Visible by table 4:
Navy blue reactive dye composition of the present invention has good moving and dyes and the level dyeing performance.
Embodiment 5
Colour fastness to perspiration
Measure the colour fastness to perspiration of following dyestuff as stated above, test result is recorded in the table 5
Table 5
Figure BDA0000035867100000231
Visible by table 5:
Navy blue reactive dye composition of the present invention has excellent fastness to perspiration.
Embodiment 6
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 6
Table 6
Figure BDA0000035867100000232
Visible by table 6:
Navy blue reactive dye composition of the present invention has excellent fastness to soaping and color fastness to water.
Embodiment 7
Sun-resistant fastness
Measure the sun-resistant fastness of following dyestuff as stated above, test result is recorded in the table 7
Table 7
Figure BDA0000035867100000241
Visible by table 7:
Navy blue reactive dye composition of the present invention still has good sun-resistant fastness.

Claims (9)

1. navy blue reactive dye composition, this dye composite contain the dye composition, one or more general formulas (2-A) of one or more general formulas (1) expression or (2-B) dye composition of expression and the dye composition of one or more general formulas (3) expression:
Figure FDA0000035867090000011
In the formula:
M is H, alkali metal cation or ammonium ion;
Y 1Be CH 2CH 2OSO 3M or-CH=CH 2
X is Cl or F;
p 1, q 1, r 1Be respectively 0 or 1 independently;
R 1Be H or C 1-C 4Alkyl;
R 11And R 12Be H, C independently respectively 1-C 4Alkyl, C 1-C 4Alkoxyl group, Cl or-SO 3M;
Figure FDA0000035867090000021
In the formula:
M is H, alkali metal cation or ammonium ion;
Y 2For-CH 2CH 2OSO 3M or-CH=CH 2
X is Cl or F;
p 2, q 2And r 2Be respectively 0 or 1 independently;
R 2Be H or C 1-C 4Alkyl;
R 4Be H, C 1-C 4Alkyl, C 1-C 4Alkoxyl group, halogen or hydroxyl;
R 13And R 14Be H, C independently respectively 1-C 4Alkyl, C 1-C 4Alkoxyl group, sulfonic group or Cl;
Figure FDA0000035867090000022
In the formula:
M is H, alkali metal cation or ammonium ion;
Y 3For-CH 2CH 2OSO 3M or-CH=CH 2
X is Cl or F;
p 3And q 3Be respectively 0 or 1 independently;
R 3Be H or C 1-C 4Alkyl;
R 5Be H, C 1-C 4Alkyl, C 1-C 4Alkoxyl group, halogen or hydroxyl;
R 15And R 16Be H, C independently respectively 1-C 4Alkyl, C 1-C 4Alkoxyl group, sulfonic group or Cl;
Figure FDA0000035867090000031
In the formula:
M is H, alkali metal cation or ammonium ion;
Y 4For-CH 2CH 2OSO 3M or-CH=CH 2
R 6Be H, C 1-C 4Alkyl, C 1-C 4Alkoxyl group, sulfonic group or Cl;
R 7Be H, C 1-C 4Alkyl or carboxyl;
R 8For H, sulfonic group or-SO 2Y 4Group;
R 9And R 10Be H, C independently respectively 1-C 4Alkyl, C 1-C 4Alkoxyl group, sulfonic group or Cl.
2. the described navy blue reactive dye composition of claim 1; Its characteristic is; Consisting of of navy blue reactive dye composition of the present invention: the dye composition of one or more general formulas (1) expressions: the dye composition of one or more general formulas (2-A) or general formula (2-B) expression: the dye composition of one or more general formulas (3) expression weight ratio be 5~30: 20~50: 30~70, be preferably 10~30: 20~40: 40~60.
3. the described navy blue reactive dye composition of claim 1, its characteristic be, general formula (1), general formula (2-A) and general formula (2-B) left side-SO 3The M group is worked as p 1, p 2, p 3Equal at 1 o'clock, be positioned on the benzene nucleus
Figure FDA0000035867090000032
Position or contraposition between group.General formula (1), general formula (2-A) and general formula (2-B) middle part-SO 3The M group is worked as r 1, r 2Equal at 1 o'clock, be positioned on the benzene nucleus-the N=N-group between position or contraposition.
4. the described navy blue reactive dye composition of claim 1, its characteristic be, general formula (1), general formula (2-A) and general formula (2-B) downside-SO 3The M group is worked as q 1, q 2, q 3Equal at 1 o'clock, be positioned on the benzene nucleus
Figure FDA0000035867090000041
The contraposition of group, a position or ortho position; The R of general formula (2-A) and general formula (2-B) downside 4And R 5, be separately located on the benzene nucleus respectively
Figure FDA0000035867090000042
The contraposition of group, a position or ortho position.
5. the described navy blue reactive dye composition of claim 1, its characteristic be, general formula (1), general formula (2-A), general formula (2-B) right side-SO 2Y 1Group ,-SO 2Y 2Group and-SO 2Y 3Group is separately located on the benzene nucleus respectively
Figure FDA0000035867090000043
Group or
Figure FDA0000035867090000044
Group or
Figure FDA0000035867090000045
The contraposition of group, a position or ortho position; The R on general formula (1), general formula (2-A), general formula (2-B) right side 11, R 12, R 13, R 14, R 15And R 16Group is separately located on the benzene nucleus respectively
Figure FDA0000035867090000046
Group or
Figure FDA0000035867090000047
Group or
Figure FDA0000035867090000048
The contraposition of group, a position or ortho position.
6. the described navy blue reactive dye composition of claim 1, its characteristic be, general formula (3) left side-SO 2Y 4Group is positioned on the benzene nucleus-the N=N-group between position or contraposition; The R in general formula (3) left side 6Group, be positioned on the benzene nucleus-the N=N-group between the ortho position of position or be positioned on the benzene nucleus-O-group.
7. the described navy blue reactive dye composition of claim 1, its characteristic is, the R on general formula (3) right side 8Group is positioned on the benzene nucleus
Figure FDA0000035867090000049
The contraposition of group or a position; The R on general formula (3) right side 9And R 10Group is separately located in respectively on the benzene nucleus-ortho position, a position or the contraposition of N=N-group.
8. the described navy blue reactive dye composition of claim 1~7, its characteristic are that the dye composition of general formula (1) expression is:
Figure FDA0000035867090000051
Dyestuff 1-6
The dye composition of general formula (2-A) expression is:
Figure FDA0000035867090000071
Figure FDA0000035867090000081
Figure FDA0000035867090000091
The dye composition of general formula (2-B) expression is:
Figure FDA0000035867090000101
Figure FDA0000035867090000111
Dyestuff 2-B-6
The dye composition of general formula (3) expression is:
Figure FDA0000035867090000121
Figure FDA0000035867090000131
In the claim 1~9 each described navy blue reactive dye composition in the application of the dyeing aspect of hydroxyl and/or formamido-material, particularly filamentary material.
CN201010571175.XA 2010-12-03 2010-12-03 Navy blue reactive dye composition and its application in fiber dyeing Active CN102485802B (en)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103275516A (en) * 2013-06-06 2013-09-04 恒升化工(启东)有限公司 Production method of acidic yellow dye containing active groups
CN103952013A (en) * 2014-05-12 2014-07-30 浙江亿得化工有限公司 Compound reactive brilliant blue dye composition as well as application and use method of compound reactive brilliant blue dye composition
CN103952014A (en) * 2014-05-12 2014-07-30 浙江亿得化工有限公司 Composite reactive blue dye and application thereof
CN105295443A (en) * 2015-11-30 2016-02-03 无锡新德印染制品有限公司 High-color fastness navy blue reactive dye composition

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1512019A (en) * 1975-10-23 1978-05-24 Ici Ltd Reactive metal complex formazan dyes
US4999027A (en) * 1988-08-26 1991-03-12 Ciba-Geigy Corporation Process for trichromatic dyeing or printing
JPH04175378A (en) * 1990-11-08 1992-06-23 Sumitomo Chem Co Ltd Reactive dye composition and method for dyeing or printing fibrous material using the same
US5488100A (en) * 1992-10-16 1996-01-30 Basf Aktiengesellschaft Formazan-based reactive dyes with at least two reactive groups, and aminophenols
EP0730010A1 (en) * 1995-03-03 1996-09-04 Basf Aktiengesellschaft Mixtures of reactive dyes for navy blue hue
US6171348B1 (en) * 1996-09-30 2001-01-09 Dystar Textilfarben Gmbh Blue dyeing mixtures of fiber-reactive dyestuffs and their use for dyeing fiber material containing hydroxy and/or carboxamide groups
US6407220B1 (en) * 2001-12-14 2002-06-18 Everlight Usa, Inc. Reactive formazan dyestuffs
US20030204919A1 (en) * 2000-07-29 2003-11-06 Joachim Steckelberg Dye mixture of water soluble, fiber-reactive dyes, method for their production and the use thereof
KR100531409B1 (en) * 2002-10-01 2005-11-28 (주)경인양행 Mixture dyes of metal complex formazan derivatives and methods for reactive dyeing with them
WO2007085572A2 (en) * 2006-01-26 2007-08-02 Dystar Textilfarben Gmbh & Co Deutschland Kg Mixtures of fibre reactive dyes production and use thereof

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4175378B2 (en) * 2006-04-19 2008-11-05 コニカミノルタビジネステクノロジーズ株式会社 Developing device and image forming apparatus having developing device

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1512019A (en) * 1975-10-23 1978-05-24 Ici Ltd Reactive metal complex formazan dyes
US4999027A (en) * 1988-08-26 1991-03-12 Ciba-Geigy Corporation Process for trichromatic dyeing or printing
JPH04175378A (en) * 1990-11-08 1992-06-23 Sumitomo Chem Co Ltd Reactive dye composition and method for dyeing or printing fibrous material using the same
US5488100A (en) * 1992-10-16 1996-01-30 Basf Aktiengesellschaft Formazan-based reactive dyes with at least two reactive groups, and aminophenols
EP0730010A1 (en) * 1995-03-03 1996-09-04 Basf Aktiengesellschaft Mixtures of reactive dyes for navy blue hue
US6171348B1 (en) * 1996-09-30 2001-01-09 Dystar Textilfarben Gmbh Blue dyeing mixtures of fiber-reactive dyestuffs and their use for dyeing fiber material containing hydroxy and/or carboxamide groups
US20030204919A1 (en) * 2000-07-29 2003-11-06 Joachim Steckelberg Dye mixture of water soluble, fiber-reactive dyes, method for their production and the use thereof
US6407220B1 (en) * 2001-12-14 2002-06-18 Everlight Usa, Inc. Reactive formazan dyestuffs
KR100531409B1 (en) * 2002-10-01 2005-11-28 (주)경인양행 Mixture dyes of metal complex formazan derivatives and methods for reactive dyeing with them
WO2007085572A2 (en) * 2006-01-26 2007-08-02 Dystar Textilfarben Gmbh & Co Deutschland Kg Mixtures of fibre reactive dyes production and use thereof

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103275516A (en) * 2013-06-06 2013-09-04 恒升化工(启东)有限公司 Production method of acidic yellow dye containing active groups
CN103952013A (en) * 2014-05-12 2014-07-30 浙江亿得化工有限公司 Compound reactive brilliant blue dye composition as well as application and use method of compound reactive brilliant blue dye composition
CN103952014A (en) * 2014-05-12 2014-07-30 浙江亿得化工有限公司 Composite reactive blue dye and application thereof
CN103952013B (en) * 2014-05-12 2016-03-16 浙江亿得化工有限公司 A kind of compound reactive brilliant blue K-GR composition and use thereof and using method
CN103952014B (en) * 2014-05-12 2016-08-24 浙江亿得化工有限公司 A kind of composite reactive blue dye and application thereof
CN105295443A (en) * 2015-11-30 2016-02-03 无锡新德印染制品有限公司 High-color fastness navy blue reactive dye composition

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