CN101974254B - Black and blue series disperse dye composition - Google Patents

Black and blue series disperse dye composition Download PDF

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CN101974254B
CN101974254B CN 201010519396 CN201010519396A CN101974254B CN 101974254 B CN101974254 B CN 101974254B CN 201010519396 CN201010519396 CN 201010519396 CN 201010519396 A CN201010519396 A CN 201010519396A CN 101974254 B CN101974254 B CN 101974254B
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formula
alkyl
dye composition
blue series
disperse dye
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CN101974254A (en
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赵国生
阮海兴
叶华明
顾伟娣
沈兰兰
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Zhejiang Runtu Co Ltd
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Zhejiang Runtu Co Ltd
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Abstract

The invention discloses a black and blue series disperse dye composition which contains at least one dye monomer A shown as formula (I) and at least one dye monomer B shown as formula (II). The disperse dye composition of the invention has the advantages of extremely good compatibility, wide application range of the pH value while dyeing, strong deep dyeing property, high color yield, good fastness, low production cost, low price and high environmental protection performance, thus being the disperse dye composition with excellent comprehensive properties, wherein, formula (I) and formula (II) are shown in description.

Description

A kind of black blue series disperse dye composition
Technical field
The present invention relates to a kind of black blue series disperse dye composition, especially a kind of environment-friendly type is deceived blue series disperse dye composition, is specially adapted to dyeing and the stamp of terylene and BLENDED FABRIC thereof.
Background technology
In the printing and dyeing of polyester material, the black blue series of dispersed dye is to use one of wider dyestuff.The serial dispersed dye of black indigo plant of environment-friendly type are generally by EX-SF DISPERSE BLUE EX-SF 300 291:1,63 DISPERSE Violet 63 93#, DISPERSE ORANGE 30 200 76# or formed by EX-SF DISPERSE BLUE EX-SF 300 291#, 63 DISPERSE Violet 63 93:1, DISPERSE ORANGE 30 200 288# blending in the market.But DISPERSE ORANGE 30 200 76# under given conditions can cracking and produce harmful arylamine, human body is produced irritated, is classified as the forbidding dyestuff by European Union member countries such as Germany.
Although DISPERSE ORANGE 30 200 288# is the environmental protection dyestuff, it remains further to be improved at compatibleness, depth, the aspect such as opacifying property, and particularly the third of the twelve Earthly Branches, look more serious, is subject to certain limitation to the printing and dyeing of the higher high-grade import trevira of look requirement in the third of the twelve Earthly Branches time.Therefore, dyeing is badly in need of seeking an environment-friendly type, high-performance, is deceived blue series disperse dye composition cheaply, to satisfy the needs of outlet.
Summary of the invention
The invention provides a kind of black blue series disperse dye composition, solved a difficult problem of being brought by DISPERSE ORANGE 30 200 76# and DISPERSE ORANGE 30 200 288#.Composition of the present invention when dyeing the pH value applied widely, depth is strong, dye yield is high, every fastness is all good.
A kind of black blue series disperse dye composition contains at least a suc as formula the dye monomer A shown in (I) and at least a suc as formula the dye monomer B shown in (II);
Wherein, formula (I) is:
Figure BDA0000029500330000011
In formula, X is cyano group or halogen; R 1Be hydrogen or C 1~C 4Alkoxyl group; R 2Be C 1~C 4Alkyl; R 3, R 4Independent separately is hydrogen, C 1~C 4Alkyl, C 2~C 4Alkenyl or C 1~C 4Alkyl on a hydrogen quilt-OH ,-CN ,-OCOR 5,-OCOOR 5,-COOR 5,-C 6H 5,-OC 6H 5Or C 1~C 4Alkoxyl group replaces, R 5Be hydrogen or C 1~C 4Alkyl.
Formula (II):
Figure BDA0000029500330000021
X in formula 1, X 2, X 3Separately independent be H ,-CN ,-NO 2, halogen or C 1~C 4Alkyl, and work as X 1For-NO 2, X 2During for H, X 3For-CN ,-NO 2Or C 1~C 4Alkyl; X 4For H ,-CN, halogen, C 1~C 4Alkyl or C 1~C 4Alkoxyl group; R 6Be C 1~C 4Alkyl, C 2~C 4Alkenyl, or C 1~C 4Alkyl a hydrogen quilt-CN ,-COOR 8,-OCOR 8,-OCOOR 8Or C 1~C 4Alkoxyl group replace, R wherein 8Be C 1~C 4Alkyl; R 7Be H or C 1~C 4Alkyl, n is 1 or 2.
In production, selecting formula (I) dye monomer is weight 50%~85%, and the dye monomer of formula (II) is weight 15%~50%.
Preferably, described black blue series disperse dye composition contains at least a suc as formula the dye monomer A shown in (I) and at least a suc as formula the dye monomer B shown in (II) and suc as formula the dye monomer C shown in (III):
Figure BDA0000029500330000022
Wherein: X is-CN, Br, Cl, R1 is C 1~C 4Alkoxyl group, R 2Be C 1~C 4Alkyl, R 3, R 4Independent separately is C 1~C 4Alkyl ,-CH 2CH=CH 2,-CH 2CH 2OCOCH 3,
Figure BDA0000029500330000023
Figure BDA0000029500330000031
Wherein: X 1, X 2, X 3Separately independent be H ,-CN ,-NO 2, halogen or C 1~C 4Alkyl and X 1For-NO 2, X 2During for H, X 3Be not H or halogen; X 1, X 2, X 3Be not H simultaneously;
Wherein: Y is Br or Cl.
The dye monomer B of through type (II) adds separately, and the crock fastness after dye composite is used is excellent especially; Adding of the dye monomer of through type (III) can be regulated coloured light, satisfies the requirement of different occasions.
In production, selecting formula (I) dye monomer is weight 27%~66%, and the dye monomer of formula (II) is weight 14%~40%, and the dye monomer of formula (III) is weight 20%~43%.
More preferred, described (I) formula dye monomer is one or more of following compounds:
Figure BDA0000029500330000033
Figure BDA0000029500330000041
Figure BDA0000029500330000051
Described (II) formula dye monomer is one or more of following compounds:
Figure BDA0000029500330000052
Figure BDA0000029500330000061
Figure BDA0000029500330000071
Dye monomer A and dye monomer B are mixture state when producing.
Disperse dye composition of the present invention generally need to add auxiliary agent to disperse during application.Described auxiliary agent is dispersed dye dispersion agent commonly used, diffusants etc. when composite, is preferably one of following or any one mixture wherein: the anionic dispersing agents such as naphthalene sulfonic acidformaldehyde condensation product, alkyl naphthalene sulfonic acid formaldehyde condensation products, benzyl sulfonic formaldehyde condensation compound, sulfonated lignin.
More preferred, described auxiliary agent is one of following or any one mixture wherein: dispersing agent NNO (sodium methylene bis-naphthalene sulfonate), Dispersant MF (condensation compound of methyl naphthalene sulfonic acid and formaldehyde), dispersing agent CNF (benzyl naphthalenesulfonate formaldehyde condensation compound), sodium lignosulfonate (as commercial dispersants Reax83A, Reax 85A) etc.Usually, auxiliary agent and dye monomer weight and ratio be 0.8~5: 1.
Disperse dye composition of the present invention can prepare by the following method: after the former dyestuff of dye monomer is mixed by a certain percentage, under existing, auxiliary agent, water or other tensio-active agent carry out particlized with pulverizers such as sand mill or shredders, then spraying drying.Above-mentioned dye monomer all can adopt commercially available prod or preparation voluntarily.
Black blue series disperse dye composition of the present invention can be aqueously after corpusculed, can be powdery, particulate state after spraying drying.Disperse dye composition compatibleness of the present invention is fabulous, when dyeing the pH value applied widely, depth is strong, dye yield is high, every fastness is all good, and low, the low price that manufactures a finished product, environmental-protecting performance is high, is a black blue series disperse dye composition that over-all properties is superior.
Embodiment
The invention will be further described below in conjunction with implementation column, but protection scope of the present invention is not limited to this.
Embodiment 1~18
According to data shown in table 1, with dye monomer A, dye monomer B and condensation compound of methyl naphthalene sulfonic acid and formaldehyde (Dispersant MF), naphthalene sulfonic acidformaldehyde condensation product (dispersing agent NNO), sodium lignosulfonate (xylogen 83A, 85A), after adding the water blending, carry out grinding distribution, then spraying drying with sand mill.
Dye monomer wherein all can adopt commercially available prod or preparation voluntarily.
The EX-SF DISPERSE BLUE EX-SF 300 291:1 that structural formula (I-1) can adopt Zhejiang Province Runtu intercalated Co., Ltd to produce;
The EX-SF DISPERSE BLUE EX-SF 300 291:2 that structural formula (I-2) can adopt Zhejiang Province Runtu intercalated Co., Ltd to produce;
The EX-SF DISPERSE BLUE EX-SF 300 291# that structural formula (I-3) can adopt Zhejiang Province Runtu intercalated Co., Ltd to produce;
The EX-SF DISPERSE BLUE EX-SF 300 modification 291# that structural formula (I-4) can adopt Zhejiang Province Runtu intercalated Co., Ltd to produce;
The Disperse Blue-79 that structural formula (I-5) can adopt Zhejiang Province Runtu intercalated Co., Ltd to produce: 1;
The Disperse Blue-79 # that structural formula (I-6) can adopt Zhejiang Province Runtu intercalated Co., Ltd to produce;
The Disperse Blue-79 that structural formula (I-7) can adopt Zhejiang Province Runtu intercalated Co., Ltd to produce: 2;
The EX-SF DISPERSE BLUE EX-SF 300 165:1 that structural formula (I-8) can adopt Zhejiang Province Runtu intercalated Co., Ltd to produce;
The 63 DISPERSE Violet 63 93# that structural formula (I-9) can adopt Zhejiang Province Runtu intercalated Co., Ltd to produce;
The 63 DISPERSE Violet 63 93:1 that structural formula (I-10) can adopt Zhejiang Province Runtu intercalated Co., Ltd to produce;
The EX-SF DISPERSE BLUE EX-SF 300 316:1 that structural formula (I-11) can adopt Zhejiang Province Runtu intercalated Co., Ltd to produce;
The EX-SF DISPERSE BLUE EX-SF 300 291:4 that structural formula (I-12) can adopt Zhejiang Province Runtu intercalated Co., Ltd to produce;
The preparation method of structural formula (II-1) is: after adjacent cyano-aniline diazotization, then form with N-cyanoethyl-Phenhenzamine coupling;
The preparation method of structural formula (II-2) is: after 2-nitro-4-chloroaniline diazotization, then form with N-cyanoethyl-Phenhenzamine coupling;
The preparation method of structural formula (II-3) is: after 3-chloroaniline diazotization, then form with 3-methyl-N-ethyl-Phenhenzamine coupling;
The preparation method of structural formula (II-4) is: after 2-N-methyl-p-nitroaniline diazotization, then form with N-cyanoethyl-Phenhenzamine coupling;
The preparation method of structural formula (II-5) is: after 2-cyano group-4-dinitraniline diazotization, then form with N-cyanoethyl-Phenhenzamine coupling;
The preparation method of structural formula (II-6) is: after 3-N-methyl-p-nitroaniline diazotization, then form with N-cyanoethyl-Phenhenzamine coupling;
The preparation method of structural formula (II-7) is: after 2-chloroaniline diazotization, then form with N-cyanoethyl-Phenhenzamine coupling;
The preparation method of structural formula (II-8) is: after 2,4-dinitraniline diazotization, then form with N-cyanoethyl-Phenhenzamine coupling;
The preparation method of structural formula (II-9) is: after aniline diazotization, then form with N-cyanoethyl-Phenhenzamine coupling;
The preparation method of structural formula (II-10) is: after 3-N-methyl-p-nitroaniline diazotization, then form with 3-oxyethyl group-N-propenyl-Phenhenzamine coupling;
The preparation method of structural formula (II-11) is: after 2-N-methyl-p-nitroaniline diazotization, then form with 3-methyl-N-ethyl-N-styroyl aniline coupling;
The preparation method of structural formula (II-12) is: after 4-chloroaniline diazotization, then form with N-methyl-Phenhenzamine coupling;
The preparation method of structural formula (II-13) is: after aniline diazotization, then form with N-methyl-Phenhenzamine coupling.
Table 1
Figure BDA0000029500330000101
Annotate: all added the dye monomer of formula (III) in embodiment, wherein embodiment 1,2,3,5,9,10,12,16 has added preferably the dye monomer suc as formula (II).
Performance test
The dye mixture that above-described embodiment 1~18 is made carries out performance test, and testing method is as follows:
According to the similar method of GB/T2394-2003, respectively get the dispersed dye that 0.5 gram embodiment 1~18 makes, water is mixed with respectively the dispersed dye suspension that concentration is 0.5g/500ml, get 20ml and mix with the water of 80ml, regulate dye bath pH to 5 with acetic acid, then be warmed up to 60 ℃, put into respectively simultaneously 2 gram trevira and carry out high-temperature pressure dyeing, be warmed up to 130 ℃ in 35 minutes, be incubated 30 minutes, be cooled to 80 ℃ of samplings.
Observe cloth specimen coloured light and adopt GB/T3921-1997, GB/T3920-1997, GB/T5718-1997 to measure its dyefastness, measurement result sees Table 2.
Table 2
Figure BDA0000029500330000111
By the test result of table 2 as can be known, dye composite dyeing compatibleness of the present invention is splendid, and every fastness such as light fastness, crock fastness, sublimation fastness, washing fastness are all excellent.Have wide market outlook.

Claims (7)

1. a black blue series disperse dye composition, contain at least a suc as formula the dye monomer A shown in (I) and at least a suc as formula the dye monomer B shown in (II);
Wherein, formula (I) is:
Figure FDA0000029500320000011
In formula, X is cyano group or halogen; R 1Be hydrogen or C 1~C 4Alkoxyl group; R 2Be C 1~C 4Alkyl; R 3, R 4Independent separately is hydrogen, C 1~C 4Alkyl, C 2~C 4Alkenyl or C 1~C 4Alkyl on a hydrogen quilt-OH ,-CN ,-OCOR 5,-OCOOR 5,-COOR 5,-C 6H 5,-OC 6H 5Or C 1~C 4Alkoxyl group replaces, R 5Be hydrogen or C 1~C 4Alkyl;
Formula (II) is:
Figure FDA0000029500320000012
X in formula 1, X 2, X 3Separately independent be H ,-CN ,-NO 2, halogen or C 1~C 4Alkyl, and work as X 1For-NO 2, X 2During for H, X 3For-CN ,-NO 2Or C 1~C 4Alkyl; X 4For H ,-CN, halogen, C 1~C 4Alkyl or C 1~C 4Alkoxyl group; R 6Be C 1~C 4Alkyl, C 2~C 4Alkenyl or C 1~C 4Alkyl a hydrogen quilt-CN ,-COOR 8,-OCOR 8,-OCOOR 8Or C 1~C 4Alkoxyl group replace, R wherein 8Be C 1~C 4Alkyl; R 7Be H or C 1~C 4Alkyl, n is 1 or 2.
2. black blue series disperse dye composition according to claim 1, it is characterized in that: described black blue series disperse dye composition contains at least a suc as formula the dye monomer A shown in (I) and at least a suc as formula the dye monomer B shown in (II) and at least a suc as formula the dye monomer C shown in (III):
Wherein: X is-CN, Br or Cl, R 1Be C 1~C 4Alkoxyl group, R 2Be C 1~C 4Alkyl, R 3, R 4Independent separately is C 1~C 4Alkyl ,-CH 2CH=CH 2,-CH 2CH 2OCOCH 3,
Wherein: X 1, X 2, X 3Separately independent be H ,-CN ,-NO 2, halogen or C 1~C 4Alkyl and X 1For-NO 2, X 2During for H, X 3Be not H or halogen; X 1, X 2, X 3Be not H simultaneously;
Figure FDA0000029500320000023
Wherein: Y is Br or Cl.
3. black blue series disperse dye composition according to claim 1, it is characterized in that: described (I) formula dye monomer is one or more of following compounds:
Figure FDA0000029500320000024
Figure FDA0000029500320000031
Figure FDA0000029500320000041
4. black blue series disperse dye composition according to claim 1, it is characterized in that: described (II) formula dye monomer is one or more of following compounds:
Figure FDA0000029500320000042
5. black blue series disperse dye composition according to claim 1, it is characterized in that: it is weight 50%~85% that described black blue series disperse dye composition is selected formula (I) dye monomer, and the dye monomer of formula (II) is weight 15%~50%.
6. black blue series disperse dye composition according to claim 2, it is characterized in that: it is weight 27%~66% that described black blue series disperse dye composition is selected formula (I) dye monomer, the dye monomer of formula (II) is weight 14%~40%, and the dye monomer of formula (III) is weight 20%~43%.
7. the described black blue series disperse dye composition of according to claim 1~6 arbitrary claims, it is characterized in that: in described black blue series disperse dye composition, dye monomer with the ratio of auxiliary agent weight is: 1: 0.8~5.
CN 201010519396 2010-10-26 2010-10-26 Black and blue series disperse dye composition Expired - Fee Related CN101974254B (en)

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CN102153888A (en) * 2011-02-24 2011-08-17 浙江万丰化工有限公司 Disperse dye compound
CN102344694B (en) * 2011-11-14 2012-07-04 浙江闰土股份有限公司 Composite dye composition, composite disperse dye and preparation method thereof
CN102344695B (en) * 2011-11-14 2012-07-04 浙江闰土股份有限公司 Composite dye composition, composite disperse dye and preparation method thereof
CN102660145B (en) * 2012-04-28 2014-06-25 浙江万丰化工有限公司 Disperse dye composition for disperse/reactive dye combination printing, and preparation and application thereof
CN102702790B (en) * 2012-06-07 2014-06-18 江苏之江化工有限公司 Disperse black azo dye mixture
CN102775809B (en) * 2012-08-09 2014-07-02 江苏之江化工有限公司 Cyano-containing azo disperse dye
CN103275512A (en) * 2013-05-28 2013-09-04 江苏之江化工有限公司 Blue monoazo dye
CN111500088B (en) * 2020-04-24 2021-08-17 王羽蘅 Disperse yellow dye composition, dye product and application

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CN101307191A (en) * 2008-06-28 2008-11-19 浙江龙盛集团股份有限公司 Disperse dye composition and disperse dye

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CN101307191A (en) * 2008-06-28 2008-11-19 浙江龙盛集团股份有限公司 Disperse dye composition and disperse dye

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