CN104788994A - Dispersed azo dye mixture, product thereof, and use of product in printing and dyeing of hydrophobic synthetic materials - Google Patents

Dispersed azo dye mixture, product thereof, and use of product in printing and dyeing of hydrophobic synthetic materials Download PDF

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Publication number
CN104788994A
CN104788994A CN201510114166.0A CN201510114166A CN104788994A CN 104788994 A CN104788994 A CN 104788994A CN 201510114166 A CN201510114166 A CN 201510114166A CN 104788994 A CN104788994 A CN 104788994A
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formula
compound
dyestuff
iii
weight
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计刘华
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TAIHU PACIFIC REFINING Co Ltd
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TAIHU PACIFIC REFINING Co Ltd
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Priority to CN201510114166.0A priority Critical patent/CN104788994A/en
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Abstract

The invention discloses a dispersed azo dye mixture, a product thereof, and a use of the product in printing and dyeing of hydrophobic synthetic materials. The mixture and the product contain at least one compound represented by formula (I) and at least one compound represented by formula (II) and/or formula (III), and substituent groups in the above formulas are defined as in the specification. The mixture and the product are especially useful in the printing and dyeing of hydrophobic synthetic materials.

Description

A kind of Dispers ozoic dyestuff mixture and goods thereof and the purposes for printing hydrophobic synthetic materials thereof
Technical field
The present invention relates to dye field, is exactly a kind of Dispers ozoic dyestuff mixture and goods thereof and the purposes for printing hydrophobic synthetic materials thereof.
Background technology
The serial kind maximum as usage quantity in deep color dispersion dyes of blue-black, C.I. DISPERSE ORANGE 30 200 76 is because of its colour fastness excellence, and colorant match excellent property, normal and C.I. 63 ,DIS,PER,SE ,Vio,let, 63 93, C.I. EX-SF DISPERSE BLUE EX-SF 300 291:1 blending obtain the blue-black series dispersed dye of excellent property.But because C.I. DISPERSE ORANGE 30 200 76 under given conditions can cracking and produce harmful arylamine, human body is produced irritated, therefore by C.I. DISPERSE ORANGE 30 200 76 blending blue-black series dispersed dye be classified as prohibitive dye by European Union member countries, seek environment-friendly type, colour fastness excellence blue-black series dispersed dye become the task of top priority.Patent CN102702790A discloses and is undertaken composite by novel orange structure replacement C.I. DISPERSE ORANGE 30 200 76, can obtain new disperse black dye composition, but this disperse black dye composition particularly still has the space promoted further in washing fastness in dyeing behavior.Along with the minimizing of monogenetic dyestuff mechanical development and the limitation in deep colour dyeing thereof, the compound synergic between dyestuff and dyestuff has become trend and the emphasis of industry research in recent years.GB 1576063A discloses a kind of blue, find in research to adopt this blueness as black or navy colorant match component, there is very outstanding performance in dyeing behavior and washing fastness, can be used as a kind of novel black or navy dye goods, there is very good application prospect.
Summary of the invention
An object of the present invention is to provide the navy with various applications well performance to the admixture of disperse dyes of black and goods thereof.
Above-mentioned purpose is realized by following scheme:
A kind of Dispers ozoic dyestuff mixture, is characterized in that: it contains the compound that at least one following formula (I) represents:
In formula:
X 1for NO 2or CN,
X 2for Br, Cl or CN,
R 1for the C of the straight or branched of replacement 2~ C 4-alkyl, the substituting group of described alkyl is selected from-C l~ C 4-alkoxyl group ,-OC 6h 5;
One or more in the compound that it also represents containing following formula (II) and following formula (III):
In formula:
Y 1and Y 2be hydrogen, Cl or Br independently of each other,
R 2and R 3be hydrogen, C independently of each other 2~ C 4-alkenyl, unsubstituted or quilt-OH ,-CN ,-COOR ,-C 6h 5,-OCOR ,-OCOC 6h 5and/or C 1~ C 4the C that-alkoxyl group replaces 1~ C 4-alkyl, R is hydrogen or C l~ C 4-alkyl;
Z 1for NO 2or CN,
Z 2for Br, Cl or CN,
R 4for hydrogen or OCH 3,
R 5and R 6be hydrogen, C independently of each other 2~ C 4-alkenyl, unsubstituted or quilt-OCOR ,-C 6h 5,-CN ,-COOR ,-OC 6h 5and/or C l~ C 4the C that-alkoxyl group replaces 1~ C 4-alkyl, R is hydrogen or C 1~ C 4-alkyl.
Described Dispers ozoic dyestuff mixture, is characterized in that: the compound that described formula (I) represents is formula
(I-1) one of compound that ~ (I-8) represents:
Described Dispers ozoic dyestuff mixture, is characterized in that: the compound that described formula (II) represents is one of compound of representing of following formula (II-1) ~ (II-5):
Described Dispers ozoic dyestuff mixture, is characterized in that: the compound that described formula (III) represents is one of compound of representing of following formula (III-1) ~ (III-16):
Described Dispers ozoic dyestuff mixture, is characterized in that: one or more in the compound that the formula (II) of the compound that at least one formula (I) that it contains 1-99 % by weight represents and 1-99 % by weight and formula (III) represent.
A kind of dye preparations, is characterized in that: it contains the Dispers ozoic dyestuff mixture according to claim 1 of 10-60 % by weight, and the dispersion agent of 40-90 % by weight.
Described dye preparations, is characterized in that: described dispersion agent is selected from one of following or wherein two or more mixtures: naphthalene sulfonic acidformaldehyde condensation product, sulfonated lignin, alkyl naphthalene sulfonic acid formaldehyde condensation products, naphthalene sulfonic acidformaldehyde condensation product, benzyl naphthalene sulfonic formaldehyde condensation compound, sodium lignosulfonate.
Described dye preparations is for dyeing and printing hydrophobic synthetic materials or the solution dyed purposes for hydrophobic synthetic material.
Based on the total amount of dyestuff, dye mixture of the present invention preferably contains 1 ~ 99% (weight), is preferably 20 ~ 99% (weight), is particularly preferably the dyestuff and 1 ~ 99% (weight) of at least one formula (I) of 35 ~ 95% (weight), is preferably 1 ~ 80% (weight), is particularly preferably at least one formula (II) of 5 ~ 65% (weight) and/or the dyestuff of formula (III).
Divide three kinds of situations specifically:
A) based on the total amount of dyestuff, the dyestuff that dye mixture of the present invention preferably contains 1 ~ 99% (weight), is preferably 20 ~ 99% (weight), is particularly preferably the dyestuff and 1 ~ 99% (weight) of at least one formula (I) of 35 ~ 95% (weight), is preferably 1 ~ 80% (weight), is particularly preferably at least one formula (II) of 5 ~ 65% (weight).
B) based on the total amount of dyestuff, the dyestuff that dye mixture of the present invention preferably contains 1 ~ 99% (weight), is preferably 20 ~ 99% (weight), is particularly preferably the dyestuff and 1 ~ 99% (weight) of at least one formula (I) of 35 ~ 95% (weight), is preferably 1 ~ 80% (weight), is particularly preferably at least one formula (III) of 5-~ 65% (weight).
C) based on the total amount of dyestuff, dye mixture of the present invention preferably contains 1 ~ 99% (weight), is preferably
20 ~ 99% (weight), be particularly preferably dyestuff and 0.5 ~ 98.5% (weight) of at least one formula (I) of 35 ~ 95% (weight), be preferably 0.5 ~ 79.5% (weight), be particularly preferably the dyestuff and 0.5 ~ 98.5% (weight) of at least one formula (II) of 2.5 ~ 62.5% (weight), be preferably 0.5 ~ 79.5% (weight), be particularly preferably the dyestuff of at least one formula (III) of 2.5 ~ 62.5% (weight).Dye mixture of the present invention, particularly when having above-mentioned specific blending ratio, will obtain black to atroceruleous tone.
Inventive mixture is remarkable in especially the distillation fastness of excellence and good affinity.In addition, tinctorial yield (color yield) height all the time within the scope of pH widely.
Dye mixture of the present invention can comprise other dispersed dye.
Dye mixture of the present invention, as commodity selling or be applied to textile materials painted time, usually also need to add auxiliary agent and carry out aftertreatment.Therefore, present invention also offers a kind of Dispers ozoic dyestuff mixture goods, it is mainly containing described dye mixture and auxiliary agent, and it contains: the described dye mixture of 10 ~ 60 % by weight, and the dispersion agent of 40 ~ 90 % by weight.Described auxiliary agent be dispersed dye composite time conventional dispersion agent, diffusant and other tensio-active agent etc., preferred auxiliary agent is one of following or wherein two or more mixture: naphthalene sulfonic acidformaldehyde condensation product, sulfonated lignin, alkyl naphthalene sulfonic acid formaldehyde condensation products (as condensation compound of methyl naphthalene sulfonic acid and formaldehyde (Dispersant MF)), naphthalene sulfonic acidformaldehyde condensation product (dispersing agent NNO), benzyl naphthalene sulfonic formaldehyde condensation compound (dispersing agent CNF), sodium lignosulfonate (xylogen 85A, xylogen 83A) etc.
Due to the singularity of dye industry, be difficult to also there is no need to make dyestuff sterling, and usually with the impurity in some preparation process, when dye mixture of the present invention makes finished product, can also allow the physical impurity containing a small amount of moisture and trace.
The preparation method of Dispers ozoic dyestuff mixture goods of the present invention is as follows:
By the dye monomer compound (former dyestuff) represented by formula (I), formula (II) and/or formula (III) by after the mixing of above-mentioned proportioning, under the existence of auxiliary agent, water or other wetting agent, carry out corpusculed with the pulverizer such as sand mill or shredder; Also mix with above-mentioned ratio after the dye monomer compound represented by formula (I), formula (II) and formula (III) can being carried out corpusculed process with the pulverizer such as sand mill or shredder respectively under the existence of auxiliary agent, water or other wetting agent in addition.The sapphire blue dye composite of dispersion of the present invention, aqueous with can be after sand mill or shredder grinding, can be powdery, particulate state after spraying dry.This well known to a person skilled in the art preparation method.
Present invention also offers described Dispers ozoic dyestuff mixture goods in dyeing and printing hydrophobic synthetic materials or the solution dyed purposes for hydrophobic synthetic material.
The Dispers ozoic dyestuff mixture goods that Dispers ozoic dyestuff mixture of the present invention is made, for hydrophobic material dyeing keratin-fiber and stamp, due to distillation fastness and the good affinity of excellence, lifting force is good, is applicable to deep colour dyeing, and washing fastness is given prominence to.
Embodiment
Below in conjunction with specific embodiment, the invention will be further described, but protection scope of the present invention is not limited to this.
Embodiment 1
A) by the dyestuff of 14 grams of following formulas (I-1):
With
The dyestuff of 20 grams of following formulas (II-1):
And
The dyestuff of 10 grams of following formulas (III-1):
In sand mill, grind 3 hours with 300 ml waters and 56 grams of sulfonated lignin (sodium salt) together, then carry out spraying dry (inlet temperature 130 DEG C, temperature out 60 DEG C).The powder (about 100 grams) of gained is easy to be distributed in water.
B) by the powder of 0.4 gram of above-mentioned preparation PH=4.5 with process about 60 minutes by the conventional H T method of printing and dyeing together with 10 grams of poly-vinegar textile materialss at 130 DEG C.Carry out washing, obtain having after rinsing and drying the as black as jet dyeing of goodish fastness performance.
Embodiment 2-8
Other dye mixture is obtained by the method for embodiment 1, and use it for the dyeing of poly-vinegar, the raw material of obtained dye mixture adopts the dyestuff of the formula (II-1) of 20 grams of embodiments 1, the dyestuff of the formula (III-1) of 10 grams of embodiments 1, and the dyestuff of 14 grams of general formulas (I) (wherein various substituting group is defined in table 1), the dyestuff of table 1 general formula (I)
Embodiment sequence number X 1 X 2 R 1
2 NO 2 Br C 2H 4OCH 3
3 NO 2 Br C 2H 4OC 2H 4
4 NO 2 Br C 3H 6OC 2H 4
5 NO 2 Cl C 3H 6OCH 3
6 NO 2 Cl C 2H 4OCH 3
7 NO 2 Cl C 2H 4OC 2H 5
8 NO 2 Cl C 3H 6OC 2H 5
Embodiment 9
Grind by the method for embodiment 1:
The dyestuff of 30 grams of following formulas (I-1):
With
The dyestuff of 9 grams of following formulas (I-3):
And
The dyestuff of 5 grams of following formulas (II-1):
And this millbase is dry.
Adopt as in embodiment 1 relative to the sulfonated lignin (sodium salt) of dyestuff total amount same ratio.Then use the dye mixture of gained (0.1 gram) to be 10 grams of poly-vinegar fiber dyeing, obtain the bright atroceruleous printing product with excellent washing and distillation fastness performance.
Embodiment 10-16
Repeat the method for embodiment 9, mix with the dyestuff of the formula of following table 2 (I) and formula (II).Keep formula (the I-1)+formula (I-3) of embodiment 9: the weight ratio of formula (I I-1), the i.e. dyestuff 39 grams of formula (I), the dyestuff of formula (II) 5 grams.Obtain band green to reddish navy printing product.
The dyestuff of table 2 general formula (I) and general formula (II)
Embodiment 17
Grind by the method for embodiment 1:
The dyestuff of 35 grams of following formulas (I-1):
The dyestuff of 9 grams of following formulas (III-11):
And this millbase is dry.
Adopt as in embodiment 1 relative to the sulfonated lignin (sodium salt) of dyestuff total amount same ratio.Then use the dye mixture of gained (0.1 gram) to be 10 grams of poly-vinegar fiber dyeing, obtain the bright atroceruleous printing product with excellent washing and distillation fastness performance.
Embodiment 18-24
Repeat the method for embodiment 17, mix with the dyestuff of the formula of following table 3 (I) and formula (III).Keep the formula (I-1) of embodiment 17: the weight ratio of formula (III-11).Obtain band green to reddish navy printing product.
The dyestuff of table 3 general formula (I) and general formula (III)
Embodiment 25
Grind by the method for embodiment 1:
A) by the dyestuff of 12 grams of following formulas (I-1):
With
The dyestuff of 20 grams of following formulas (II-1):
With
The dyestuff of 8 grams of following formulas (III-1):
And
The dyestuff of 4 grams of following formulas (III-11):
And this millbase is dry.
Adopt as in embodiment 1 relative to the sulfonated lignin (sodium salt) of dyestuff total amount same ratio.Then use the dye mixture of gained (0.1 gram) to be 10 grams of poly-vinegar fiber dyeing, obtain the printing product of the black with excellent washing and distillation fastness performance.
Embodiment 26-40
Repeat the method for embodiment 25, mix with the dyestuff of the dyestuff of the formula of following table 4 (III) and formula (I-1), formula (II-1) and formula (III-1).Keep the formula (I-1) of embodiment 25: formula (II-1): formula (III-1): the weight ratio of formula (III-11).Obtain the black printing product of ruddiness to green light.In all situations, result all obtains good pH interdependence, excellent dye uptake (bath exhaustion) and good distillation fastness performance.
The dyestuff of table 4 general formula (III)
Embodiment sequence number Z 1 Z 2 R 4 R 5 R 6
26 NO 2 Cl OCH 3 C 2H 5 C 2H 4CN
27 NO 2 Br OCH 3 C 2H 5 C 2H 4CN
28 NO 2 Cl OCH 3 C 2H 4OCH 3 C 2H 4OCH 3
29 NO 2 Br OCH 3 C 2H 4OCH 3 C 2H 4OCH 3
30 NO 2 CN H C 2H 5 C 2H 5
31 NO 2 Cl OCH 3 C 2H 5 C 2H 5
32 NO 2 Cl OCH 3 H CH 2CH=CH 2
33 NO 2 Br OCH 3 H CH 2CH=CH 2
34 NO 2 Br OCH 3 C 2H 4COOCH 3 C 2H 4COOCH 3
35 NO 2 Br OCH 3 C 2H 4CN C 2H 4CN
36 NO 2 Br OCH 3 C 2H 4CN CH 2C 6H 5
37 NO 2 Cl OCH 3 C 2H 4CN C 2H 4COOCH 3
38 NO 2 Br OCH 3 C 2H 4OCOC 6H 5 C 2H 4OCOC 6H 5
39 NO 2 Br OCH 3 H C 2H 4CN
40 NO 2 Cl H CH 2CH=CH 2 CH 2CH=CH 2

Claims (8)

1. a Dispers ozoic dyestuff mixture, is characterized in that: it contains the compound that at least one following formula (I) represents:
In formula:
X 1for NO 2or CN,
X 2for Br, Cl or CN,
R 1for the C of the straight or branched of replacement 2~ C 4-alkyl, the substituting group of described alkyl is selected from-C l~ C 4-alkoxyl group ,-OC 6h 5;
One or more in the compound that it also represents containing following formula (II) and following formula (III):
In formula:
Y 1and Y 2be hydrogen, Cl or Br independently of each other,
R 2and R 3be hydrogen, C independently of each other 2~ C 4-alkenyl, unsubstituted or quilt-OH ,-CN ,-COOR ,-C 6h 5,-OCOR ,-OCOC 6h 5and/or C 1~ C 4the C that-alkoxyl group replaces 1~ C 4-alkyl, R is hydrogen or C l~ C 4-alkyl;
Z 1for NO 2or CN,
Z 2for Br, Cl or CN,
R 4for hydrogen or OCH 3,
R 5and R 6be hydrogen, C independently of each other 2~ C 4-alkenyl, unsubstituted or quilt-OCOR ,-C 6h 5,-CN ,-COOR ,-OC 6h 5and/or C l~ C 4the C that-alkoxyl group replaces 1~ C 4-alkyl, R is hydrogen or C 1~ C 4-alkyl.
2. Dispers ozoic dyestuff mixture according to claim 1, is characterized in that: the compound that described formula (I) represents is one of compound of representing of formula (I-1) ~ (I-8):
3. Dispers ozoic dyestuff mixture according to claim 1, is characterized in that: the compound that described formula (II) represents is one of compound of representing of following formula (II-1) ~ (II-5):
4. Dispers ozoic dyestuff mixture according to claim 1, is characterized in that: the compound that described formula (III) represents is one of compound of representing of following formula (III-1) ~ (III-16):
5. Dispers ozoic dyestuff mixture according to claim 1, is characterized in that: one or more in the compound that the formula (II) of the compound that at least one formula (I) that it contains 1-99 % by weight represents and 1-99 % by weight and formula (III) represent.
6. a dye preparations, is characterized in that: it contains the Dispers ozoic dyestuff mixture according to claim 1 of 10-60 % by weight, and the dispersion agent of 40-90 % by weight.
7. dye preparations according to claim 6, is characterized in that: described dispersion agent is selected from one of following or wherein two or more mixtures: naphthalene sulfonic acidformaldehyde condensation product, sulfonated lignin, alkyl naphthalene sulfonic acid formaldehyde condensation products, naphthalene sulfonic acidformaldehyde condensation product, benzyl naphthalene sulfonic formaldehyde condensation compound, sodium lignosulfonate.
8. the dye preparations of claim 6 is used for dyeing and printing hydrophobic synthetic materials or the solution dyed purposes being used for hydrophobic synthetic material.
CN201510114166.0A 2015-03-16 2015-03-16 Dispersed azo dye mixture, product thereof, and use of product in printing and dyeing of hydrophobic synthetic materials Pending CN104788994A (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107345083A (en) * 2017-06-28 2017-11-14 浙江龙盛化工研究有限公司 It is a kind of blue to black disperse dye composition and dye preparations
CN110776439A (en) * 2019-11-06 2020-02-11 蓬莱嘉信染料化工股份有限公司 Azo compound, preparation method and application thereof, dye composition, dye, preparation method and application thereof
CN112724705A (en) * 2020-12-31 2021-04-30 浙江龙盛染料化工有限公司 Blue-to-black disperse dye composition and dye product

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1576063A (en) * 1978-03-02 1980-10-01 Yorkshire Chemicals Ltd Monoazo disperse dyes
GB2346150A (en) * 1999-02-01 2000-08-02 Ciba Sc Holding Ag Dye mixtures and their use for dyeing or printing cellulose acetate-containing fibre materials
CN1696205A (en) * 2005-05-20 2005-11-16 浙江闰土股份有限公司 Composite environment-friendly disperse dye
CN1793240A (en) * 2005-09-28 2006-06-28 杭州吉华化工有限公司 Dispersing dye mixture and dye products
CN1844260A (en) * 2006-04-29 2006-10-11 浙江闰土股份有限公司 Mixed black and blue series combined disperse dye
CN102702790A (en) * 2012-06-07 2012-10-03 江苏之江化工有限公司 Disperse black azo dye mixture

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1576063A (en) * 1978-03-02 1980-10-01 Yorkshire Chemicals Ltd Monoazo disperse dyes
GB2346150A (en) * 1999-02-01 2000-08-02 Ciba Sc Holding Ag Dye mixtures and their use for dyeing or printing cellulose acetate-containing fibre materials
CN1696205A (en) * 2005-05-20 2005-11-16 浙江闰土股份有限公司 Composite environment-friendly disperse dye
CN1793240A (en) * 2005-09-28 2006-06-28 杭州吉华化工有限公司 Dispersing dye mixture and dye products
CN1844260A (en) * 2006-04-29 2006-10-11 浙江闰土股份有限公司 Mixed black and blue series combined disperse dye
CN102702790A (en) * 2012-06-07 2012-10-03 江苏之江化工有限公司 Disperse black azo dye mixture

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107345083A (en) * 2017-06-28 2017-11-14 浙江龙盛化工研究有限公司 It is a kind of blue to black disperse dye composition and dye preparations
CN107345083B (en) * 2017-06-28 2019-08-13 浙江龙盛化工研究有限公司 It is a kind of blue to black disperse dye composition and dye preparations
CN110776439A (en) * 2019-11-06 2020-02-11 蓬莱嘉信染料化工股份有限公司 Azo compound, preparation method and application thereof, dye composition, dye, preparation method and application thereof
CN110776439B (en) * 2019-11-06 2022-11-01 蓬莱嘉信染料化工股份有限公司 Azo compound, preparation method and application thereof, dye composition, dye, preparation method and application thereof
CN112724705A (en) * 2020-12-31 2021-04-30 浙江龙盛染料化工有限公司 Blue-to-black disperse dye composition and dye product

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