CN109554003B - Disperse dye composition, disperse dye, and preparation method and application thereof - Google Patents
Disperse dye composition, disperse dye, and preparation method and application thereof Download PDFInfo
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- CN109554003B CN109554003B CN201811574838.6A CN201811574838A CN109554003B CN 109554003 B CN109554003 B CN 109554003B CN 201811574838 A CN201811574838 A CN 201811574838A CN 109554003 B CN109554003 B CN 109554003B
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0046—Mixtures of two or more azo dyes
- C09B67/0051—Mixtures of two or more azo dyes mixture of two or more monoazo dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/16—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dispersed, e.g. acetate, dyestuffs
- D06P1/18—Azo dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/46—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing natural macromolecular substances or derivatives thereof
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/673—Inorganic compounds
- D06P1/67333—Salts or hydroxides
- D06P1/6735—Salts or hydroxides of alkaline or alkaline-earth metals with anions different from those provided for in D06P1/67341
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/34—Material containing ester groups
- D06P3/52—Polyesters
- D06P3/54—Polyesters using dispersed dyestuffs
Abstract
The invention relates to a disperse dye composition, a disperse dye, and a preparation method and application thereof. The disperse dye composition comprises: at least one component A of formula (I); a component B represented by the formula (II); at least one component C of formula (III); at least one component D of the formula (IV); a component E represented by the formula (V). The disperse dye disclosed by the invention comprises the disperse dye composition and auxiliary materials, is high in strength and low in cost, and has the characteristics of good lifting power, good blackness, excellent rubbing fastness, excellent washing fastness and the like when being applied to dyeing of hydrophobic fiber materials.
Description
Technical Field
The invention relates to a disperse dye composition, a disperse dye, a preparation method and application thereof. The disperse dye is suitable for dyeing terylene and blended fabrics thereof.
Background
Along with the gradual increase of the government on pollution control strength, the environmental protection consciousness of the people in China is strengthened year by year, and great impact is generated on the development of dye enterprises. The traditional disperse dye spliced by C.I. disperse yellow 23# has good level-dyeing property and excellent fastness, is highly approved by wide users, and has larger market share ratio. However, c.i. disperse yellow 23# is a dye obtained by diazotizing p-aminoazobenzene, which generates substances against human cancers, coupled with phenol, and has been completely banned. In addition, the anthraquinone dye component in the disperse dye spliced by the C.I. disperse yellow 23# has high specific gravity, high cost and low cost performance. In the face of huge market demands, how to develop a low-cost, high-performance, economic and environment-friendly disperse dye of the same type is a difficult problem for a plurality of dye enterprises.
Disclosure of Invention
The invention provides a disperse dye composition which has the characteristics of high strength, low cost, good lifting power, good blackness, excellent rubbing fastness, excellent washing fastness and the like.
Means for solving the problems
The invention provides a disperse dye composition, which comprises the following components:
at least one component A of formula (I):
X1、X2each independently of the other being H, Cl, Br or NO2；R1Is H or C1～C4Alkyl groups of (a);
component B of formula (II):
at least one component C represented by formula (III):
X3is H or Br;
at least one component D of formula (IV):
X4is H or Cl; r2、R3Each independently is C1～C4Alkyl or cyano-substituted C1～C4An alkyl group;
a component E represented by the formula (V):
the disperse dye composition provided by the invention is characterized in that the component A is one or more than two of the following compounds:
the disperse dye composition provided by the invention is characterized in that the component C is one or more than two of the following compounds:
the disperse dye composition provided by the invention is characterized in that the component D is one or more than two of the following compounds:
according to the disperse dye composition, based on the total weight of the disperse dye composition, the content of the component A is 15-50%, preferably 22-40%, the content of the component B is 10-40%, preferably 15-32%, the content of the component C is 10-35%, preferably 15-30%, the content of the component D is 5-25%, preferably 7-20%, and the content of the component E is 10-30%, preferably 12-25%.
In practice, the dye components of the present invention may often carry some by-products and other impurities without affecting the practice of the present invention.
The invention also provides a disperse dye, which comprises the disperse dye composition and auxiliary materials; preferably, the auxiliary materials comprise an auxiliary agent and water; more preferably, the auxiliary agent comprises one or more of a surfactant, a bactericide or a dye dispersant; further preferably, the dye dispersant comprises one or a combination of two or more of the following: naphthalene sulfonic acid formaldehyde condensates (e.g., dispersant MF, dispersant CNF, dispersant NNO), lignosulfonates (e.g., lignin 85A, lignin 83A), or anhydrous sodium sulphate.
According to the disperse dye, the weight ratio of the auxiliary agent to the disperse dye composition is 0.2-7.5: 1; preferably, the disperse dye is liquid after being ground by a sand mill or a grinding machine, and the solid content is 20-50%, or the disperse dye is powdery or granular after being spray-dried, and the solid content is 87-96%.
The invention also provides a method for preparing the disperse dye, which is characterized by comprising the following steps:
mixing the dye components, and then carrying out granulation treatment by using a sand mill or a grinding machine in the presence of auxiliary materials; or granulating the dye components by a sand mill or a grinding machine in the presence of auxiliary materials, and mixing.
The invention also provides the use of the disperse dyes according to the invention for dyeing textiles; preferably, the fabric is terylene and blended fabric thereof.
The invention also provides a fabric prepared by dyeing with the disperse dye; preferably, the fabric is terylene and blended fabric thereof.
ADVANTAGEOUS EFFECTS OF INVENTION
The disperse dye disclosed by the invention is low in cost, high in strength, economic and environment-friendly, is applied to dyeing of hydrophobic fiber materials, and has the characteristics of good lifting force, good blackness, excellent rubbing fastness, excellent washing fastness and the like.
Detailed Description
The present invention is further illustrated by the following examples, but the scope of the invention is not limited thereto.
In the examples, component A, B, C, D, E of the present invention is mixed with the assistant and water according to a certain proportion, and then ground and dispersed by a sand mill to prepare slurry, or further spray-dried to prepare disperse dye.
The component A, B, C, D, E is a known dye compound and is commercially available or can be prepared by existing protocols.
The preparation or source of the specific compounds used in the examples are as follows.
A compound of formula (I-1): is prepared by diazotizing 2, 6-dichloro-4-nitroaniline and coupling with N-ethyl-N-chloroethyl-m-toluidine by a known method.
A compound of formula (I-2): prepared by diazotizing 2, 4-dinitro-6-bromoaniline and coupling with N-ethyl-N-chloroethyl m-toluidine by a known method.
A compound of formula (I-3): diazotizing 2-chloro-4-nitroaniline and coupling it with N-ethyl-N-chloroethylaniline by known methods.
A compound of formula (I-4): diazotizing 2-chloro-4-nitroaniline and coupling with N-ethyl-N-chloroethyl-m-toluidine by known methods.
A compound of formula (II): commercial c.i. disperse blue 360;
a compound of formula (III-1): a commercially available C.I. disperse yellow 64 product manufactured by Zhejiang lea soil Limited;
a compound of formula (III-2): commercially available product of C.I. disperse yellow 54 produced by Zhejiang lea soil Limited company;
a compound of formula (IV-1): a commercial product of C.I. disperse orange 25:1 produced by Zhejiang lea soil Limited;
a compound of formula (IV-2): a commercially available C.I. disperse orange 25 manufactured by Zhejiang lea soil Limited;
a compound of formula (IV-3): a commercially available product of disperse red 50 of C.I. produced by Zhejiang lea soil Limited;
a compound of formula (V): a commercially available product of disperse blue 56, c.i. produced by zhejiang lea soil gmbh.
Example 1
28 g of component A of the formula (I-1), 22 g of component B of the formula (II), 20 g of component C of the formula (III-2), 12 g of component D of the formula (IV-3), 18 g of component E of the formula (V) and 262 g of dispersing agent CNF, 543 g of water are added, and after grinding and dispersing with a sand mill, spray drying is carried out to prepare the disperse dye.
Comparative example 1
33 g of the component of the formula (1), 12 g of the component of the formula (2), 13 g of the component of the formula (IV-3), 42 g of the component of the formula (V) and 262 g of a dispersing agent CNF were added with 543 g of water, and after grinding and dispersing with a sand mill, spray drying was carried out to prepare a disperse dye.
The disperse dyes of example 1 and comparative example 1 were subjected to a performance test.
The specific test method is as follows:
1 g of the finished dyes from example 1 and 1 g of comparative example 1 are weighed into a 500ml measuring flask, respectively, according to the method of GB/T2394-2006, to form a disperse dye suspension. 4% of O.W.F.absorbs 40ml of disperse dye suspension to be mixed with 60ml of water, 1% of O.W.F.absorbs 10ml of disperse dye suspension to be mixed with 90ml of water, the pH value of a dye bath is adjusted to 5 by using acetic acid, then the temperature is raised to 60 ℃, 2g of polyester fiber is respectively placed into the dye bath to carry out high-temperature high-pressure dyeing, the temperature is raised to 130 ℃ within 35min, the temperature is kept for 45min, and the sample is taken after being cooled to 80 ℃.
Observing the color light of the cloth sample, and testing the rubbing fastness and washing fastness of 4% of O.W.F.4% of example 1 and comparative example 1 by using GB/T3920-2008 and GB/T3921-2008; the relative strength of O.W.F. 1% for example 1 and comparative example 1 was tested using GB/T6688-2008 and the results are shown in Table 1.
TABLE 1 (Unit: grade)
| Name of the embodiment | Fastness to rubbing | Fastness to washing | Strength of |
| Example 1 | 5 | 5 | 192％ |
| Comparative example 1 | 4-5 | 4-5 | 100％ |
As can be seen from Table 1, example 1 has a clear advantage in rubbing fastness and washing fastness compared to comparative example 1. Meanwhile, the strength of the dye in example 1 is nearly doubled compared with that in comparative example 1, and thus, the disperse dye prepared from the disperse dye composition provided by the invention can greatly reduce the dye consumption and save the printing cost on the basis of improving the printing and dyeing performance.
Examples 2 to 15
Examples 2 to 15 the proportions of the components are shown in Table 2, the disperse dyes are prepared in the same manner as in example 1, and the water content in Table 2 is the water content of the commercial products.
TABLE 2 (Unit: gram)
With reference to the procedure of example 1, 1 g of the finished dyes of examples 2 to 15 were weighed into a 500ml measuring flask, respectively, to prepare a disperse dye suspension. Absorbing 40ml of disperse dye suspension by 4 percent of O.W.F.and mixing with 60ml of water, adjusting the pH value of a dye bath to 5 by using acetic acid, then heating to 60 ℃, simultaneously respectively adding 2g of polyester fiber for high-temperature high-pressure dyeing, heating to 130 ℃ within 35min, preserving heat for 45min, cooling to 80 ℃ and sampling.
Observing the color light of the cloth sample, and testing the color light of 4 percent of O.W.F. by adopting GB/T3920-2008 and GB/T3921-2008
The rubfastness and wash fastness of examples 2-15 are shown in Table 3.
TABLE 3 (Unit: grade)
| Name of the embodiment | Fastness to rubbing | Fastness to washing |
| Example 2 | 5 | 5 |
| Example 3 | 5 | 5 |
| Example 4 | 5 | 5 |
| Example 5 | 5 | 5 |
| Example 6 | 5 | 5 |
| Example 7 | 5 | 5 |
| Example 8 | 5 | 5 |
| Example 9 | 5 | 5 |
| Example 10 | 5 | 5 |
| Example 11 | 5 | 5 |
| Example 12 | 5 | 5 |
| Example 13 | 5 | 5 |
| Example 14 | 5 | 5 |
| Example 15 | 5 | 5 |
As can be seen from Table 3, the rubfastness and the wash fastness of examples 2 to 15 both achieved a 5-grade.
Claims (17)
1. A disperse dye composition characterized by comprising:
at least one component A of formula (I):
X1、X2each independently of the other being H, Cl, Br or NO2；R1Is H or C1～C4Alkyl groups of (a);
component B of formula (II):
at least one component C represented by formula (III):
X3is H or Br;
at least one component D of formula (IV):
X4is H or Cl; r2、R3Each independently is C1～C4Alkyl or cyano-substituted C1～C4An alkyl group;
a component E represented by the formula (V):
2. the disperse dye composition according to claim 1, wherein the component A is one or more of the following compounds:
3. a disperse dye composition according to claim 1 or 2, wherein the component C is one or more than two of the following compounds:
4. a disperse dye composition according to claim 1 or 2, wherein the component D is one or more than two of the following compounds:
5. the disperse dye composition according to claim 1 or 2, wherein the content of component A is 15% to 50%, the content of component B is 10% to 40%, the content of component C is 10% to 35%, the content of component D is 5% to 25%, and the content of component E is 10% to 30% based on the total weight of the disperse dye composition.
6. The disperse dye composition according to claim 1 or 2, wherein based on the total weight of the disperse dye composition, the content of component A is 22 to 40 percent, the content of component B is 15 to 32 percent, the content of component C is 15 to 30 percent, the content of component D is 7 to 20 percent, and the content of component E is 12 to 25 percent.
7. A disperse dye, which is characterized by comprising the disperse dye composition according to any one of claims 1 to 6 and an auxiliary material.
8. A disperse dye according to claim 7, wherein the auxiliary materials comprise auxiliaries and water.
9. The disperse dye according to claim 8, wherein the auxiliary agent comprises one or a combination of two or more of a surfactant, a bactericide or a dye dispersant.
10. The disperse dye according to claim 9, wherein the dye dispersant comprises one or a combination of two or more of the following: naphthalene sulfonic acid formaldehyde condensates, lignosulfonates, or anhydrous sodium sulfate.
11. A disperse dye according to claim 8, wherein the weight ratio of the auxiliary to the disperse dye composition is 0.2-7.5: 1.
12. A disperse dye according to claim 11, wherein the disperse dye is liquid after being ground by a sand mill or a grinder and has a solid content of 20 to 50%, or the disperse dye is powdery or granular after being spray-dried and has a solid content of 87 to 96%.
13. A process for preparing a disperse dye according to any one of claims 7 to 12, comprising the steps of:
mixing all the dye components, and then carrying out particle treatment by using a sand mill or a grinding machine in the presence of auxiliary materials; or granulating the dye components by a sand mill or a grinding machine in the presence of auxiliary materials, and mixing.
14. Use of a disperse dye according to any one of claims 7 to 12 for dyeing textiles.
15. The use according to claim 14, said fabric being polyester and blends thereof.
16. A fabric prepared by dyeing with the disperse dye according to any one of claims 7 to 12.
17. The fabric of claim 16, wherein the fabric is polyester and blends thereof.
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| CN201811574838.6A CN109554003B (en) | 2018-12-21 | 2018-12-21 | Disperse dye composition, disperse dye, and preparation method and application thereof |
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| CN109554003B true CN109554003B (en) | 2020-09-11 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112442283B (en) * | 2019-08-28 | 2022-05-27 | 浙江闰土股份有限公司 | Azo type disperse dye compound suitable for dyeing in acid-alkaline bath, preparation method, composition and application thereof |
| CN114196230B (en) * | 2021-12-21 | 2023-12-19 | 浙江闰土股份有限公司 | Disperse dye composition, disperse dye, preparation method and application thereof |
| CN114163840B (en) * | 2021-12-21 | 2023-12-19 | 浙江闰土股份有限公司 | Disperse dye composition, disperse dye, preparation method and application thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101143973A (en) * | 2007-10-26 | 2008-03-19 | 浙江闰土股份有限公司 | Low-temperature environmental protection disperse yellow dye composition |
| CN101914308A (en) * | 2010-07-23 | 2010-12-15 | 浙江闰土股份有限公司 | Grey disperse dye composition |
| CN102888129A (en) * | 2012-06-26 | 2013-01-23 | 上海宜连化工科技有限公司 | Disperse dye composition and applications thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1209281A3 (en) * | 2000-11-27 | 2003-08-27 | Carl Freudenberg KG | Dyed or printed nonwoven |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101143973A (en) * | 2007-10-26 | 2008-03-19 | 浙江闰土股份有限公司 | Low-temperature environmental protection disperse yellow dye composition |
| CN101914308A (en) * | 2010-07-23 | 2010-12-15 | 浙江闰土股份有限公司 | Grey disperse dye composition |
| CN102888129A (en) * | 2012-06-26 | 2013-01-23 | 上海宜连化工科技有限公司 | Disperse dye composition and applications thereof |
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