CN110922784B - Disperse yellow-to-red dye composition, dye product and application thereof - Google Patents

Disperse yellow-to-red dye composition, dye product and application thereof Download PDF

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Publication number
CN110922784B
CN110922784B CN201911164913.6A CN201911164913A CN110922784B CN 110922784 B CN110922784 B CN 110922784B CN 201911164913 A CN201911164913 A CN 201911164913A CN 110922784 B CN110922784 B CN 110922784B
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component
disperse
dye composition
disperse yellow
dye
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CN110922784A (en
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孟明
孟福庆
田景峰
韩伟
吴于鑫
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Shaoxing Shangyu Jinguan Chemical Co ltd
ZHEJIANG LONGSHENG CHEMICAL RESEARCH CO LTD
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Shaoxing Shangyu Jinguan Chemical Co ltd
ZHEJIANG LONGSHENG CHEMICAL RESEARCH CO LTD
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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
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/008—Preparations of disperse dyes or solvent dyes
    • 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
    • C09B67/0047—Mixtures of two or more reactive 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
    • D06P1/16—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
    • 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

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  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)

Abstract

The invention discloses a disperse yellow-to-red dye composition which comprises a component A and a component B, wherein the component A is selected from at least one compound shown in a formula (I), the component B is selected from at least one compound shown in a formula (II), based on the component A and the component B, the mass percentage of the component A is 5-95%, and the mass percentage of the component B is 5-95%. When the disperse yellow-to-red dye composition is applied to dyeing or printing of polyester and blend fiber materials thereof, the disperse yellow-to-red dye composition has comprehensive and excellent color fastness.

Description

Disperse yellow-to-red dye composition, dye product and application thereof
(I) technical field
The invention relates to a disperse yellow to red dye composition, a dye product thereof and application of the dye product in dyeing of hydrophobic fiber materials.
(II) background of the invention
With the development of polyester and blended fabrics thereof, particularly in recent years, spandex-containing elastic fabrics are very popular in domestic and foreign markets, the products have excellent resilience, soft hand feeling and comfortable wearing, are easy to absorb sweat and can not generate static electricity, the fabrics are mainly dyed by disperse dyes, but the general disperse dyes have high affinity and good dyeability to spandex, so that the disperse dyes are seriously stained to the spandex. During the fastness test, disperse dyes stained on spandex are easy to migrate out of the fiber, and the wet treatment fastness of the terylene/spandex textile is influenced. Many disperse dyes have good fastness to rubbing, washing and light on terylene, but the fastness on spandex can only reach a medium level, so that products with high requirements on the fastness have a great problem in dyeing processing.
The heterocyclic ring-containing disperse dye is one direction of more researches in the field in recent years, because the dye has better dark color effect and higher molar extinction coefficient, a group of disperse dyes (ZL200880013404.7) taking benzyl substituted pyridone as a coupling component is developed by Kelaien in 2008, the disperse dyes are mainly used for optically recording data, are used for dyeing fabrics poorly and are difficult to color, and the applicant finds that the disperse dyes can be used for dyeing textile materials after being improved and have outstanding performance.
Disclosure of the invention
The invention aims to provide a disperse yellow-to-red dye composition and a dye product thereof, which have comprehensive and excellent color fastness performance when applied to dyeing of hydrophobic fibers, particularly polyester and blend fiber materials thereof.
In order to achieve the purpose, the invention adopts the technical scheme that:
a disperse yellow-to-red dye composition comprises a component A and a component B, wherein the component A is selected from at least one compound shown in a formula (I), the component B is selected from at least one compound shown in a formula (II), based on the component A and the component B, the mass percent of the component A is 5-95%, the mass percent of the component B is 5-95%,
Figure BDA0002287198620000011
Figure BDA0002287198620000021
in formula (I):
X1is H, NO2CN or-OCH3，X2Is H, NO2、-OCH3Cl or Br;
R1is benzyl or phenethyl.
In formula (II):
X3is Cl, Br, NO2Or CN, X4H, Cl or Br;
R2is C1～C4Alkyl radical, C1～C4Alkoxyalkyl or benzyl.
In the above formulas (I) and (II), C1～C4The alkyl group may be methyl, ethyl, linear or branched propyl, linear or branched butyl, said C1～C4The alkoxyalkyl group can be methoxyethyl, methoxypropyl, ethoxyethyl, ethoxypropyl, and the like. R2Preferably methyl or ethyl.
The component a and the component B are the main components of the disperse yellow to red dye composition, and within the scope known to those skilled in the art, the composition of the present invention may further comprise other dye monomers or auxiliaries applicable to compounding, such as c.i. disperse orange 288, c.i. disperse red 73, etc., and the compound dye composition obtained by the above modification is also within the protection scope of the present invention.
In the disperse yellow to red dye composition of the present invention, component A is preferably at least one selected from the following formulas (I-1) to (I-10), wherein Ph is a phenyl group:
Figure BDA0002287198620000022
Figure BDA0002287198620000031
Figure BDA0002287198620000041
the component B is preferably at least one selected from the following formulas (II-1) to (II-10):
Figure BDA0002287198620000042
Figure BDA0002287198620000051
Figure BDA0002287198620000061
preferably, the disperse yellow-to-red dye composition comprises a component A and a component B, wherein the component A is at least one of formulas (I-1) to (I-7), the component B is at least one of formulas (II-1) to (II-6), based on the component A and the component B, the mass percent of the component A is 5-95%, and the mass percent of the component B is 5-95%.
Further preferably, the disperse yellow to red dye composition consists of component a and component B, wherein:
the component A is at least one of formulas (I-1) to (I-7);
the component B is at least one of formulas (II-1) to (II-6).
Based on the total weight of the dye component A, B, the mass percentage of the component A is 5-95%, and the mass percentage of the component B is 5-95%.
It should be emphasized that in the disperse yellow to red dye composition according to the present invention, the dye coupled at the ortho position of the pyridone or tetrahydroquinolinone hydroxyl group generally exists in the form of quinone hydrazone structure, that is, the dye of the general formulas (i), (ii) substantially has the quinone hydrazone structure shown in the following formulas (ia), (iia), and in consideration of the writing habit of those skilled in the art, the writing form of azo is still adopted in the summary and the examples section, which does not affect the essence of the present invention:
Figure BDA0002287198620000071
wherein X1、X2、X3、X4、R1、R2The same as defined above for the compounds of the formulae (I) and (II).
The disperse yellow to red dye composition of the invention usually needs to be added with conventional auxiliary agents in the commercial process. Therefore, the invention also provides a disperse dye product which contains the disperse yellow-to-red dye composition and an auxiliary agent, wherein the weight ratio of the auxiliary agent to the disperse yellow-to-red dye composition is (0.2-5): 1, preferably (0.5-2): 1. Preferably, the disperse dye product consists of a disperse yellow to red dye composition and an auxiliary agent. The auxiliary agent is a dispersing agent, other surfactants and the like which are commonly used in the process of compounding disperse dyes, and is particularly preferably selected from one or a mixture of more than two of the following components: lignosulfonate (e.g., commercially available dispersant Reax 83A, Reax 8A), methyl naphthalenesulfonic acid formaldehyde condensate (dispersant MF), naphthalenesulfonic acid formaldehyde condensate (dispersant NNO), benzylnaphthalenesulfonic acid formaldehyde condensate (dispersant CNF), anhydrous sodium sulfate, polycarboxylic acid polymer dispersant, and the like.
The disperse yellow to red dye product of the invention can be obtained by the following method: mixing A, B monomer compound (crude dye) at a certain ratio, and micronizing with a grinder such as a sand mill or a grinder in the presence of adjuvant and water; alternatively, the monomeric dye compounds of component A, B may be subjected to a pulverization treatment using a pulverizer such as a sand mill or a grinder in the presence of an auxiliary agent or water, and then mixed in a certain proportion. The disperse dye preparations according to the invention can be liquid after grinding with a sand mill or a grinding mill and can be in the form of powder or granules after spray drying, which is a process known to the person skilled in the art, since it is not possible to remove 100% of the water during spray drying, so that even in the case of pulverulent or granular dye preparations a certain amount of water is still allowed, preferably not more than 10% of the total weight of the dye preparation.
In addition, when the dye product is applied to printing and dyeing of textile fibers, the technical characteristics which contribute to the improvement of the dyeing effect are the components and the proportion of the dye contained in the product.
The disperse yellow to red dye compositions of the present invention, the dye compounds of the formulae (I) and (II) can be conveniently synthesized in a manner well known to those skilled in the art, and commercially available products can also be used.
The invention provides the application of the disperse yellow-to-red dye composition and the dye product in dyeing hydrophobic fiber materials. The dye prepared by the dye composition can dye hydrophobic fiber materials (such as polyester and blended fabrics thereof) in a conventional mode in the industry, such as dyeing by a common dip dyeing method or a high-temperature high-pressure dyeing method, and can also be used for direct printing. Wherein, the common dip-dyeing method comprises the steps of pretreating the hydrophobic fiber material, putting the hydrophobic fiber material into a dye vat for dip-dyeing, washing the hydrophobic fiber material to be neutral by cold water after dyeing, wringing, reducing, washing and drying; the direct printing is to carry out dyeing pretreatment, drying and setting on the fabric, print disperse dye color paste on a printing machine, then carry out steaming, fix the color of the dye on the fabric by using a steaming mode, finally wash and tenter setting.
When the disperse dye composition and the dye product provided by the invention are applied to printing and dyeing of hydrophobic fiber materials, after heat setting treatment, the disperse dye composition still has good fastness to washing, sublimation and rubbing, does not contain carcinogenic sensitizing dye, and meets the ecological and environment-friendly requirements of high-grade fabric dyeing.
(IV) detailed description of the preferred embodiments
The invention will be further described with reference to specific examples, but the scope of the invention is not limited thereto:
example 1
40 g of dye compound shown in formula (I-1), 60 g of dye compound shown in formula (II-1) and 150 g of dispersing agent MF are mixed with 500 g of water, and then the mixture is ground, dispersed and spray-dried to obtain a finished product, wherein the finished product can provide orange red color tone for polyester and blended fabrics thereof.
Figure BDA0002287198620000081
Examples 2 to 30
According to the method described in the example 1, except that the structures and the weights of the component A and the component B in the following table 1 are adopted, 160 g of the auxiliary agent (150 g of the dispersing agent MF and 10 g of the sodium lignosulfonate) is added, 650 g of water is added for blending to prepare slurry, and the slurry is ground, dispersed and dried to prepare the finished product, and the dye can provide yellow to red tones with excellent fastness properties for polyester and blended fabrics thereof.
TABLE 1
Figure BDA0002287198620000091
Figure BDA0002287198620000101
Example 31
70 g of dye compound shown as a formula (I-2), 25 g of dye compound shown as a formula (II-1), 5 g of dye compound shown as C.I. disperse orange 288 and 150 g of dispersant CNF are mixed with water, ground and dispersed by a grinding machine and dried to obtain the finished dye, and the dye can provide uniform yellowish-brown color tone with good fastness performance for polyester and blended fabrics thereof.
Example 32
50 g of a compound of a formula (I-1), 25 g of a compound of a formula (II-2), 25 g of C.I. disperse red 73 and 150 g of a dispersant CNF are mixed with water, ground and dispersed by a grinding machine and dried to obtain the finished dye, and the dye can provide uniform orange color tone with good fastness performance for polyester and blended fabrics thereof.
Dyeing examples
Respectively weighing 2 g of the disperse dyes prepared in the embodiments 1-32, treating the polyester/ammonia mixed fabric by adopting a conventional high-temperature high-pressure dyeing method, controlling the dyeing depth (o.w.f) to be 3.0% in the treatment process, regulating the pH value of a dyeing bath to be 4-5, dyeing at room temperature, heating to 130 ℃ at the speed of 1 ℃/min, keeping the temperature for 45min, reducing, cleaning, washing, drying and carrying out heat setting at 180 ℃ for 30 seconds according to the conventional method to obtain the dyed fabric. The color fastness to rubbing, washing and sublimation is respectively tested by adopting international standards ISO 105-X12 and AATCC 61-2A, ISO 105-P01, and the color fastness to rubbing, washing and sublimation is specifically shown in the table 2:
TABLE 2
Figure BDA0002287198620000102
Figure BDA0002287198620000111
Therefore, after the disperse yellow-to-red dye composition is subjected to high-temperature heat setting treatment, the fastness is excellent, and the requirement of printing and dyeing of the blended fabric with high fastness can be met.

Claims (8)

1. A disperse yellow-to-red dye composition comprises a component A and a component B, wherein the component A is selected from at least one compound shown in a formula (I), the component B is selected from at least one compound shown in a formula (II), based on the component A and the component B, the mass percent of the component A is 5-95%, the mass percent of the component B is 5-95%,
Figure FDA0002944981740000011
in formula (I):
X1is H, NO2CN or-OCH3，X2Is H, NO2、-OCH3Cl or Br;
R1is benzyl or phenethyl;
in formula (II):
X3is Cl, Br, NO2Or CN, X4H, Cl or Br;
R2is C1～C4Alkyl radical, C1～C4Alkoxyalkyl or benzyl.
2. A disperse yellow to red dye composition according to claim 1, wherein: the component A is selected from at least one of the following formulas, wherein Ph is phenyl,
Figure FDA0002944981740000012
Figure FDA0002944981740000021
Figure FDA0002944981740000031
3. a disperse yellow to red dye composition according to claim 1, wherein: the component B is selected from at least one of the following formulas:
Figure FDA0002944981740000032
Figure FDA0002944981740000041
Figure FDA0002944981740000051
4. a disperse yellow to red dye composition according to claim 1, wherein:
the component A is at least one of formulas (I-1) to (I-7);
the component B is at least one of formulas (II-1) to (II-6).
5. A disperse yellow to red dye composition according to claim 1 consisting of component a, component B, wherein:
the component A is at least one of formulas (I-1) to (I-7);
the component B is at least one of formulas (II-1) to (II-6);
based on the total weight of the dye component A, B, the mass percentage of the component A is 5-95%, and the mass percentage of the component B is 5-95%.
6. A disperse dye product comprising a disperse yellow to red dye composition according to any one of claims 1 to 5 and an auxiliary, the weight ratio of the auxiliary to the disperse yellow to red dye composition being from 0.2 to 5: 1.
7. A disperse dye preparation according to claim 6, wherein the auxiliaries are one or a combination of any of the following: naphthalene sulfonic acid formaldehyde condensate, methyl naphthalene sulfonic acid formaldehyde condensate, benzyl naphthalene sulfonate formaldehyde condensate, anhydrous sodium sulphate and polycarboxylic acid polymer dispersant.
8. Use of the disperse dye preparation according to claim 7 for dyeing polyester and polyester blend fabrics.
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CN115124858B (en) * 2022-06-30 2023-08-29 浙江龙盛集团股份有限公司 Disperse orange dye composition and product thereof
CN116396625A (en) * 2022-06-30 2023-07-07 浙江龙盛集团股份有限公司 Disperse orange dye composition and product thereof

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CN1322227A (en) * 1999-07-29 2001-11-14 三井化学株式会社 Yellow compound and water-based ink-jet recording ink containing compound
CN106479221A (en) * 2015-08-24 2017-03-08 杭州福莱蒽特精细化工有限公司 A kind of dark blue to black disperse dye mixture
WO2019068443A1 (en) * 2017-10-02 2019-04-11 Dystar Colours Distribution Gmbh High wet fast disperse dye mixtures

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JP2612294B2 (en) * 1988-03-11 1997-05-21 三井東圧化学株式会社 Yellow color toner composition

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Publication number Priority date Publication date Assignee Title
CN1322227A (en) * 1999-07-29 2001-11-14 三井化学株式会社 Yellow compound and water-based ink-jet recording ink containing compound
CN106479221A (en) * 2015-08-24 2017-03-08 杭州福莱蒽特精细化工有限公司 A kind of dark blue to black disperse dye mixture
WO2019068443A1 (en) * 2017-10-02 2019-04-11 Dystar Colours Distribution Gmbh High wet fast disperse dye mixtures

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