CN114196231B - Disperse dye composition, disperse dye, preparation method and application thereof - Google Patents

Disperse dye composition, disperse dye, preparation method and application thereof Download PDF

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Publication number
CN114196231B
CN114196231B CN202111572696.1A CN202111572696A CN114196231B CN 114196231 B CN114196231 B CN 114196231B CN 202111572696 A CN202111572696 A CN 202111572696A CN 114196231 B CN114196231 B CN 114196231B
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component
disperse dye
weight percentage
dye composition
disperse
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CN114196231A (en
Inventor
顾伟娣
谢子平
袁芝琴
阮芳芳
吴旭宇
阮梦宇
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Zhejiang Runtu Institute Co ltd
Zhejiang Runtu Co Ltd
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Zhejiang Runtu Institute Co ltd
Zhejiang Runtu Co Ltd
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    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00Influencing 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
    • C09B67/0033Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0041Blends of pigments; Mixtured crystals; Solid solutions mixtures containing one azo dye
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00Influencing 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
    • C09B67/0033Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0046Mixtures of two or more azo dyes
    • C09B67/0051Mixtures of two or more azo dyes mixture of two or more monoazo dyes
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00Influencing 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
    • C09B67/0071Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/008Preparations of disperse dyes or solvent dyes
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General 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
    • D06P1/16General 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
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General 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
    • D06P1/16General 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
    • D06P1/18Azo dyes
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General 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
    • D06P1/16General 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
    • D06P1/19Nitro dyes
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General 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
    • D06P1/16General 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
    • D06P1/20Anthraquinone dyes
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34Material containing ester groups
    • D06P3/52Polyesters
    • D06P3/54Polyesters using dispersed dyestuffs
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/82Textiles which contain different kinds of fibres

Abstract

The invention provides a disperse dye composition, a disperse dye, a preparation method and application thereof. The disperse dye composition comprises the following components: a component a represented by formula (1):a component B represented by the formula (2):optionally a component C as shown in formula (3):optionally a component D of formula (4):

Description

Disperse dye composition, disperse dye, preparation method and application thereof
Technical Field
The invention relates to a disperse dye composition, a disperse dye, a preparation method and application thereof, wherein the disperse dye is suitable for dyeing terylene and blended fabrics thereof, and belongs to the field of dyes.
Background
The C.I. disperse yellow 23, which is one of the three primary colors at low temperature, is forbidden due to carcinogenesis to 4-aminoazobenzene, and a plurality of substitutes such as a specific C.I. disperse yellow 54 appear on the market, and the dye is expensive and has general compatibility with the C.I. disperse red 60 and the C.I. disperse blue 56. In recent years, some brands have marked c.i. disperse yellow 54 as a sensitizing dye and require prohibition.
Patent CN104448929a discloses a grey disperse dye composition, disperse dye, preparation method and use thereof. The yellow dye used therein overcomes the above-mentioned problems, but a photosensitive phenomenon occurs during actual use, and thus, the use of this scheme is greatly limited.
The disperse dye is dyed by a high-temperature high-pressure method, the dyeing temperature is 130 ℃, and the required energy consumption is high.
Disclosure of Invention
Problems to be solved by the invention
In view of the technical problems in the prior art, the invention firstly provides a disperse dye composition and a disperse dye which are environment-friendly, have no light-sensitive phenomenon and are excellent in compatibility, color fastness and cost performance.
Furthermore, the disperse dye composition and the disperse dye can be used for low-temperature dyeing, have good fastness, and have strong comprehensive advantages.
Furthermore, the invention also provides a preparation method of the disperse dye, which is simple and easy to implement, raw materials are easy to obtain, and the preparation method is suitable for mass production.
Solution for solving the problem
The invention firstly provides a disperse dye composition which comprises the following components:
a component a represented by formula (1):
a component B represented by the formula (2):
optionally a component C as shown in formula (3):
optionally a component D of formula (4):
the disperse dye composition according to the invention, wherein the weight percentage of the component A is 1-99% based on 100% of the total weight of the disperse dye composition; the weight percentage of the component B is 1-99%; the weight percentage of the component C is 0-78%; the weight percentage of the component D is 0-40%.
The disperse dye composition according to the invention, wherein the weight percentage of the component A is 20-53% based on 100% of the total weight of the disperse dye composition; the weight percentage of the component B is 2-17%; the weight percentage of the component C is 30-78%; the weight percentage of the component D is 0%.
The disperse dye composition according to the invention, wherein the weight percentage of the component A is 20-92% based on 100% of the total weight of the disperse dye composition; the weight percentage of the component B is 4-40%; the weight percentage of the component C is 0%; the weight percentage of the component D is 4-40%.
The disperse dye composition according to the invention, wherein the weight percentage of the component A is 18-52% based on 100% of the total weight of the disperse dye composition; the weight percentage of the component B is 3-19%; the weight percentage of the component C is 15-78%; the weight percentage of the component D is 1-14%.
The present invention also provides a disperse dye comprising a disperse dye composition according to the present invention; preferably, the disperse dye further comprises an auxiliary agent and water, more preferably, the weight ratio of the auxiliary agent to the disperse dye composition is 0.2-6.0:1.
The disperse dye of the invention, wherein the auxiliary agent comprises one or more than two of a surfactant, a bactericide and a dye dispersing agent; preferably, the dye dispersant comprises one or more than two of naphthalene sulfonic acid formaldehyde condensate, lignin sulfonate and anhydrous sodium sulfate.
The disperse dye according to the present invention is in a liquid state after being ground by a sand mill or a grinding machine, and has a solid content of 20 to 50%, or in a powder or granule state after being spray-dried, and has a solid content of 87 to 96%.
The invention also provides a process for preparing the disperse dye according to the invention, comprising the steps of:
mixing the dye components, and then carrying out granulation treatment by a sand mill or a grinding machine in the presence of auxiliary materials; or the dye components are respectively subjected to granulation treatment by a sand mill or a grinding machine in the presence of auxiliary materials, and then are mixed.
The invention further provides a use of the disperse dye according to the invention for dyeing textiles; preferably, the dyeing can be carried out at a temperature above 95 ℃, preferably above 95 ℃ and below 130 ℃.
The invention further provides a fabric which is prepared by dyeing with the disperse dye.
ADVANTAGEOUS EFFECTS OF INVENTION
The disperse dye composition and the disperse dye have obvious advantages in terms of sublimation fastness, chlorinated water-resistant color fastness, light fastness and the like; and has good compatibility, high strength and low cost.
Furthermore, the disperse dye composition and the disperse dye provided by the invention can be used for low-temperature dyeing, and have good fastness, so that the disperse dye composition and the disperse dye have strong comprehensive advantages.
Furthermore, the preparation method of the disperse dye is simple and feasible, raw materials are easy to obtain, and the disperse dye is suitable for mass production.
Detailed Description
The following describes the present invention in detail. The following description of the technical features is based on the representative embodiments and specific examples of the present invention, but the present invention is not limited to these embodiments and specific examples.
Furthermore, in the following detailed description, numerous specific details are set forth in order to provide a better illustration of the invention. It will be understood by those skilled in the art that the present invention may be practiced without some of these specific details. In other instances, well known methods, procedures, means, equipment and steps have not been described in detail so as not to obscure the present invention.
It should be noted that:
in the present specification, the numerical range indicated by the term "numerical value a to numerical value B" means a range including the end point numerical value A, B.
Unless otherwise indicated, all units used in the present invention are international standard units, and numerical values, ranges of values, appearing in the present invention should be understood to include errors permitted in industrial production.
Reference throughout this specification to "some specific/preferred embodiments," "other specific/preferred embodiments," "an embodiment," and so forth, means that a particular element (e.g., feature, property, and/or characteristic) described in connection with the embodiment is included in at least one embodiment described herein, and may or may not be present in other embodiments. In addition, it is to be understood that the elements may be combined in any suitable manner in the various embodiments.
The invention firstly provides a disperse dye composition which comprises the following components:
a component a represented by formula (1):
a component B represented by the formula (2):
optionally a component C as shown in formula (3):
optionally a component D of formula (4):
in the present invention, the compounds represented by the formulae (1) to (4) may be synthesized in a manner well known to those skilled in the art, or commercially available products may be used.
Specifically, in the present invention, the weight percentage of the component a is 1 to 99%, based on 100% of the total weight of the disperse dye composition, for example: 5%, 10%, 15%, 20%, 25%, 30%, 35%, 45%, 50%, 60%, 70%, 75%, 80%, 90%, 95%, etc.; the weight percentage of the component B is 1-99%, for example: 5%, 10%, 15%, 20%, 25%, 30%, 35%, 45%, 50%, 60%, 70%, 75%, 80%, 90%, 95%, etc.; the weight percentage of the component C is 0-78%, for example: 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, etc.; the weight percentage of the component D is 0-40%, for example: 5%, 10%, 15%, 20%, 25%, 30%, 35%, etc.
Further, in some specific embodiments, the disperse dye composition of the present invention includes two components, component a and component B. Specifically, the weight percentage of component a is 1-99%, based on 100% of the total weight of the disperse dye composition, for example: 5%, 10%, 15%, 20%, 25%, 30%, 35%, 45%, 50%, 60%, 70%, 75%, 80%, 90%, 95%, etc.; the weight percentage of the component B is 1-99%, for example: 5%, 10%, 15%, 20%, 25%, 30%, 35%, 45%, 50%, 60%, 70%, 75%, 80%, 90%, 95%, etc.
Further, in other specific embodiments, the disperse dye composition of the present invention includes three components, component a, component B, and component C. Specifically, the weight percentage of component a is 20-53%, based on 100% of the total weight of the disperse dye composition, for example: 21%, 24%, 27%, 29%, 31%, 34%, 37%, 39%, 41%, 44%, 47%, 49%, 51%, 53%, etc.; the weight percentage of the component B is 2-17%, for example: 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, etc.; the weight percentage of the component C is 30-78%, for example: 32%, 35%, 38%, 41%, 45%, 49%, 52%, 55%, 59%, 63%, 66%, 69%, 73%, 77%, etc.
Further, in still other specific embodiments, the disperse dye composition of the present invention includes three components, component a, component B, and component D. Specifically, the weight percentage of component a is 20-92%, based on 100% of the total weight of the disperse dye composition, for example: 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, etc.; the weight percentage of the component B is 4-40%, for example: 4%, 7%, 9%, 12%, 15%, 18%, 20%, 22%, 25%, 28%, 30%, 32%, 35%, 38%, etc.; the weight percentage of the component D is 4-40%, for example: 4%, 7%, 9%, 12%, 15%, 18%, 20%, 22%, 25%, 28%, 30%, 32%, 35%, 38%, etc.
Further, in other specific embodiments, the disperse dye composition of the present invention includes three components, component a, component B, and component C and component D. Specifically, the weight percentage of component a is 18-52%, based on 100% of the total weight of the disperse dye composition, for example: 20%, 22%, 25%, 28%, 30%, 32%, 35%, 38%, 40%, 42%, 45%, 48%, 50%, 52%, etc.; the weight percentage of the component B is 3-19%, for example: 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, etc. The weight percentage of the component C is 15-78%, for example: 20%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, etc. The weight percentage of the component D is 1-14%, for example: 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, etc.
Further, the present invention also provides a disperse dye comprising the disperse dye composition according to the present invention; preferably, the disperse dye further comprises an auxiliary agent and water, more preferably, the weight ratio of the auxiliary agent to the disperse dye composition is 0.2-6.0:1, for example: 0.5:1, 1:1, 1.5:1, 2:1, 2.5:1, 3:1, 3.5:1, 4:1, 4.5:1, 5:1, 5.5:1, etc.
Specifically, the auxiliary agent comprises one or more than two of a surfactant, a bactericide and a dye dispersing agent; in the present invention, the specific kind of the dye dispersant is not particularly limited, and may be a dye dispersant commonly used in the art. Preferably, the dye dispersant may be one or a combination of more than two of naphthalene sulfonic acid formaldehyde condensate, lignin sulfonate and anhydrous sodium sulfate.
Further, in the present invention, the dye dispersant preferably includes one or a combination of two or more of the following: naphthalene sulfonic acid formaldehyde condensate (such as dispersant MF, dispersant CNF, and dispersant NNO), sodium lignin sulfonate (such as lignin 85A and lignin 83A), or sodium sulfate.
The disperse dyes of the present invention may be either liquid or solid. The disperse dye is in liquid state after being ground by a sand mill or a grinding machine, the solid content is 20-50%, or the disperse dye is in powder or granule form after being spray-dried, and the solid content is 87-96%.
The disperse dye has obvious advantages in sublimation fastness, chlorinated water-resistant color fastness, light fastness and the like; and has good compatibility, high strength, low cost and low energy consumption. Furthermore, the disperse dye can be used for low-temperature dyeing, has good fastness, and is a disperse dye composition and a disperse dye with strong comprehensive advantages.
The invention also provides a process for preparing the disperse dye according to the invention, comprising the steps of:
mixing the dye components, and then carrying out granulation treatment by a sand mill or a grinding machine in the presence of auxiliary materials; or the dye components are respectively subjected to granulation treatment by a sand mill or a grinding machine in the presence of auxiliary materials, and then are mixed.
Specifically, the method comprises the following steps: mixing dye monomer compounds of the disperse dye composition according to a proportion, and carrying out micropellet formation by using a grinder such as a sand grinder or a grinding machine in the presence of an auxiliary agent and water; alternatively, the dye monomers may be subjected to a micropellet treatment with a pulverizer such as a sand mill or a grinding machine in the presence of an auxiliary agent and water, respectively, and then mixed in the above proportions. The disperse dye is processed by a pulverizer such as a sand mill or a grinding machine and is in a liquid state. If solid disperse dye is needed, spray drying can be carried out or dry powder and granular can be obtained.
The invention also provides the use of the disperse dyes according to the invention for dyeing textiles. The fabric is terylene and blended fabric thereof; the dyeing includes pad dyeing. The dyeing according to the invention can be carried out at temperatures above 95 ℃, preferably above 95 ℃ and below 130 ℃, for example: 100 ℃, 105 ℃, 110 ℃, 115 ℃, 120 ℃, 125 ℃, etc.; when the disperse dye is used for dyeing, the disperse dye can be used for dyeing at high temperature and high pressure and can be used for dyeing at low temperature. In general, the temperature of the high temperature, high pressure dyeing may be greater than 125 ℃; the low temperature dyeing temperature may be 95-125 ℃.
Further, the invention also provides a fabric which is prepared by dyeing with the disperse dye. The dyeing includes pad dyeing.
Examples
Embodiments of the present invention will be described in detail below with reference to examples, but it will be understood by those skilled in the art that the following examples are only for illustrating the present invention and should not be construed as limiting the scope of the present invention. The specific conditions are not noted in the examples and are carried out according to conventional conditions or conditions recommended by the manufacturer. The reagents or apparatus used were conventional products commercially available without the manufacturer's attention.
In the examples, the component A, B, the optional component C and the optional component D according to the invention are mixed with an auxiliary agent and water according to a certain proportion, and then ground and dispersed by a sand mill to prepare a liquid dye, or further spray-dried to prepare a powdery or granular dye.
Example 1
50 g of the component A of the formula (1) and 50 g of the component B of the formula (2), 100 g of lignin 85A and 300 g of dispersant MF, and 750 g of water are added and stirred uniformly, ground, dispersed and dried to obtain the disperse dye.
Performance testing
The specific test method is as follows:
0.25 g and 1.0 g of the disperse dye of example 1 were weighed and placed in 500ml of water respectively to prepare a disperse dye suspension. Respectively sucking 20ml of disperse dye suspension, mixing with 80ml of water, regulating pH of the dye bath to 5 with acetic acid, heating to 60 ℃, simultaneously respectively placing 2g of polyester fiber for high-temperature and high-pressure dyeing, heating to 130 ℃ within 35 minutes, preserving heat for 45 minutes, cooling to 80 ℃ and sampling, wherein the dyeing depths are respectively 0.5% and 2%.
The light fastness of the dyed cloth sample is measured according to GB/T8427-2019, the sublimation fastness and the color fastness to chlorinated water of the dyed cloth sample are measured according to GB/T5718-1997 and GB/T8433-2013 by using 0.5%, and the test results are shown in Table 1:
table 1: units: stage
As can be seen from table 1, the disperse dye composition of the present invention has excellent light fastness, sublimation fastness and fastness to chlorinated water when dyed at high temperature and high pressure.
Example 2
32 g of the component A of the formula (1), 9 g of the component B of the formula (2) and 59 g of the component C of the formula (3), 400 g of lignin 85A and 80 g of dispersant MF, 870 g of water are added, and the mixture is sufficiently and uniformly stirred, ground, dispersed and dried to obtain the disperse dye.
Comparative example 1
The procedure of example 2 was repeated, except that the component A of the formula (1) of example 2 was replaced with the following formula (5), to give a disperse dye.
Comparative example 2
The procedure of example 2 was repeated, except that the component A of the formula (1) of example 2 was replaced with the following formula (6), to give a disperse dye.
Performance testing
The specific test method is as follows:
the disperse dyes of example 2, comparative example 1 and comparative example 2 were weighed in amounts of 0.25 g and 1.0 g, respectively, and placed in 500ml of water to prepare disperse dye suspensions. Respectively sucking 20ml of disperse dye suspension, mixing with 80ml of water, regulating pH of the dye bath to 5 with acetic acid, heating to 60 ℃, simultaneously respectively placing 2g of polyester fiber for high-temperature and high-pressure dyeing, heating to 130 ℃ within 35 minutes, preserving heat for 45 minutes, cooling to 80 ℃ and sampling, wherein the dyeing depths are respectively 0.5% and 2%.
The light fastness was measured with a 0.5% dyeing cloth according to GB/T8427-2019.
The photosensitive phenomenon was measured by using a method of 0.5% of dyed cloth sample reference GB/T8427-2019. The photosensitive phenomenon is the color escape phenomenon under illumination, and the natural color can be recovered after the light is far away. The specific detection method is a method of referring to GB/T8427-2019, and after the dyed cloth sample is dried for 20 hours, taking out and observing whether the yellow escape is obvious or not; then, the mixture is placed indoors for standing for half an hour, and then, whether the original color light is recovered or not is observed.
The sublimation fastness test results of a 2% dyed cloth sample according to GB/T5718-1997 are shown in Table 2:
table 2: units: stage
As can be seen from Table 2, the disperse dye composition of the present invention was stronger in light fastness and sublimation fastness and was free from a photosensitive phenomenon after dyeing than those of comparative examples 1 and 2.
Comparative example 3
The procedure of example 2 was repeated, except that the component A of the formula (1) of example 2 was replaced with the following formula (7), to give a disperse dye.
Performance testing
The specific test method is as follows:
0.25 g and 1.0 g of the disperse dyes of example 2 and comparative example 3 were weighed respectively and placed in 500ml of water to prepare disperse dye suspensions. Respectively sucking 20ml of disperse dye suspension, mixing with 80ml of water, regulating pH of the dye bath to 5 with acetic acid, heating to 60 ℃, simultaneously respectively placing 2g of polyester fiber for high-temperature and high-pressure dyeing, heating to 130 ℃ within 35 minutes, preserving heat for 45 minutes, cooling to 80 ℃ and sampling, wherein the dyeing depths are respectively 0.5% and 2%.
The light fastness of the dye was measured according to GB/T8427-2019 with 0.5% of the dye cloth sample, the sublimation fastness, the color fastness to chlorinated water, the strength and the 4-aminoazobenzene of the dye cloth sample were measured according to GB/T5718-1997, GB/T8433-2013, GB/T6688-2008 and GB/T24101 with 2% of the dye cloth sample, and the test results are shown in Table 3:
table 3 units: stage
Note that: the 4-aminoazobenzene is over-standard when the content of the 4-aminoazobenzene is more than 150mg/kg, and the limit and the measurement standard of the 4-aminoazobenzene in the GB/T24101-2018 dye product are not met; ND is a small Yu Jianchu limit, where the detection limit is less than 1.0mg/kg.
As can be seen from Table 3, the disperse dye composition of the present invention was higher in strength after dyeing than comparative example 3, and 4-aminoazobenzene was not detected.
Example 3
70 g of the component A of the formula (1), 15 g of the component B of the formula (2) and 15 g of the component D of the formula (4), 100 g of lignin 85A and 180 g of dispersing agent MF, 870 g of water are added, and the mixture is fully and uniformly stirred, ground, dispersed and dried to obtain the disperse dye.
Performance testing
The specific test method is as follows:
0.5 g and 2.0 g of the disperse dye of example 3 were each weighed and placed in 500ml of water to prepare a disperse dye suspension. Respectively sucking 20ml of disperse dye suspension, mixing with 80ml of water, regulating pH of the dye bath to 5 with acetic acid, heating to 60 ℃, simultaneously respectively placing 2g of polyester fiber for low-temperature dyeing, heating to 100 ℃ within 35 minutes, preserving heat for 30 minutes, cooling to 60 ℃ and sampling, wherein the dyeing depths are 1% and 4% respectively.
The light fastness of the dye is measured according to GB/T8427-2019 by using 1% of dyed cloth samples, the sublimation fastness and the color fastness to chlorinated water are measured according to GB/T5718-1997 and GB/T8433-2013 by using 4% of dyed cloth samples, and the test results are shown in Table 4:
table 4 units: stage
As can be seen from table 4, the dye composition of the present invention is capable of dyeing at low temperature and is excellent in various color fastness.
Examples 4 to 12
According to the contents of the components in Table 5, the component A, the component B, the component C, the component D and the auxiliary agent are mixed with water, ground to prepare slurry or spray-dried to prepare the disperse dye.
Table 5 units: gram (g)
Note that: the moisture content in table 5 is the moisture content of the final dye product.
Performance testing
1. 0.25 g and 1.0 g of the disperse dyes of examples 4-12 were each weighed and placed in 500ml of water to prepare a disperse dye suspension. Respectively sucking 20ml of disperse dye suspension, mixing with 80ml of water, regulating pH of the dye bath to 5 with acetic acid, heating to 60 ℃, simultaneously respectively placing 2g of polyester fiber for high-temperature and high-pressure dyeing, heating to 130 ℃ within 35 minutes, preserving heat for 45 minutes, cooling to 80 ℃ and sampling, wherein the dyeing depths are respectively 0.5% and 2%.
The light fastness of the dyed cloth sample is measured according to GB/T8427-2019, the sublimation fastness of the dyed cloth sample is measured according to GB/T5718-1997 and GB/T8433-2013, and the test result is shown in Table 6:
table 6 units: stage
As can be seen from table 6, the dye composition of the present invention is capable of dyeing under high temperature and high pressure conditions, and is excellent in each color fastness.
In addition, the applicant carried out the photosensitizing experiments and the 4-aminoazobenzene detection experiments on examples 3 to 12 according to the method of the present invention, and the results showed that none of examples 3 to 12 was sensitive to light and that no 4-aminoazobenzene was detected.
2. 0.5 g and 2.0 g of the disperse dyes of examples 4-12 were each weighed and placed in 500ml of water, respectively, to prepare a disperse dye suspension. Respectively sucking 20ml of disperse dye suspension, mixing with 80ml of water, regulating pH of the dye bath to 5 with acetic acid, heating to 60 ℃, simultaneously respectively placing 2g of polyester fiber for low-temperature dyeing, heating to 100 ℃ within 35 minutes, preserving heat for 30 minutes, cooling to 60 ℃ and sampling, wherein the dyeing depths are 1% and 4% respectively.
The light fastness of the dye is measured according to GB/T8427-2019 by using 1% of dyed cloth samples, the sublimation fastness and the color fastness to chlorinated water are measured according to GB/T5718-1997 and GB/T8433-2013 by using 4% of dyed cloth samples, and the test results are shown in Table 7:
table 7 units: stage
As can be seen from table 7, the dye composition of the present invention is capable of dyeing at low temperature conditions, and is excellent in each color fastness.
The above examples of the present invention are merely illustrative of the present invention and are not intended to limit the embodiments of the present invention. Other variations or modifications of the above teachings will be apparent to those of ordinary skill in the art. It is not necessary here nor is it exhaustive of all embodiments. Any modification, equivalent replacement, improvement, etc. which come within the spirit and principles of the invention are desired to be protected by the following claims.

Claims (15)

1. A disperse dye composition characterized by comprising the following components:
a component a represented by formula (1):
a component B represented by the formula (2):
component C as shown in formula (3) and/or component D as shown in formula (4):
wherein the weight percentage of the component A is 1-99% based on 100% of the total weight of the disperse dye composition; the weight percentage of the component B is 1-99%; the weight percentage of the component C is 0-78%; the weight percentage of the component D is 0-40%, and the weight percentage of the component C and the weight percentage of the component D are not 0 at the same time.
2. The disperse dye composition according to claim 1, wherein the weight percentage of component a is 20-53% based on 100% of the total weight of the disperse dye composition; the weight percentage of the component B is 2-17%; the weight percentage of the component C is 30-78%; the weight percentage of the component D is 0%.
3. The disperse dye composition according to claim 1, wherein the weight percentage of component a is 20-92% based on 100% of the total weight of the disperse dye composition; the weight percentage of the component B is 4-40%; the weight percentage of the component C is 0%; the weight percentage of the component D is 4-40%.
4. The disperse dye composition according to claim 1, wherein the weight percentage of component a is 18-52% based on 100% of the total weight of the disperse dye composition; the weight percentage of the component B is 3-19%; the weight percentage of the component C is 15-78%; the weight percentage of the component D is 1-14%.
5. Disperse dye characterized in that it comprises a disperse dye composition according to any one of claims 1 to 4.
6. The disperse dye according to claim 5, further comprising an auxiliary agent and water.
7. The disperse dye according to claim 6, wherein the weight ratio of the auxiliary agent to the disperse dye composition is 0.2-6.0:1.
8. The disperse dye according to claim 6 or 7, wherein the auxiliary agent comprises one or a combination of more than two of a surfactant, a bactericide and a dye dispersant.
9. The disperse dye according to claim 8, wherein the dye dispersant comprises one or a combination of more than two of naphthalene sulfonic acid formaldehyde condensate, lignin sulfonate and anhydrous sodium sulfate.
10. The disperse dye according to any of claims 5 to 7, wherein the disperse dye is in liquid form after grinding by a sand mill or a grinding machine, has a solid content of 20 to 50%, or is in powder or granule form after spray drying, and has a solid content of 87 to 96%.
11. A process for preparing a disperse dye according to any one of claims 5 to 10, characterized by comprising the steps of:
mixing the dye components, and performing granulation treatment by a sand mill or a grinding machine in the presence of auxiliary materials; or the dye components are respectively subjected to granulation treatment by a sand mill or a grinding machine in the presence of auxiliary materials, and then are mixed.
12. Use of a disperse dye according to any one of claims 5 to 10 for dyeing textiles.
13. Use according to claim 12, characterized in that the dyeing can be carried out at a temperature above 95 ℃.
14. Use according to claim 13, characterized in that the dyeing can be carried out at a temperature greater than 95 ℃ and below 130 ℃.
15. Fabric, characterized in that it is prepared by dyeing with a disperse dye according to any one of claims 5 to 10.
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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH10130522A (en) * 1996-09-04 1998-05-19 Sumitomo Chem Co Ltd Disperse pigment composition and dyeing of hydrophobic material with the same
JPH11158403A (en) * 1997-11-28 1999-06-15 Sumitomo Chem Co Ltd Disperse dye composition and method for coloring hydrophobic material therbwith
JP2003268255A (en) * 2002-03-19 2003-09-25 Konica Corp Black color composition, dispersion of black fine particle, inkjet ink, and inkjet recording method

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ATE499414T1 (en) * 2001-01-26 2011-03-15 Huntsman Adv Mat Switzerland AZO DYES, PROCESS FOR THEIR PRODUCTION AND THEIR USE FOR DYEING OR PRINTING HYDROPHOBIC FIBER MATERIAL

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH10130522A (en) * 1996-09-04 1998-05-19 Sumitomo Chem Co Ltd Disperse pigment composition and dyeing of hydrophobic material with the same
JPH11158403A (en) * 1997-11-28 1999-06-15 Sumitomo Chem Co Ltd Disperse dye composition and method for coloring hydrophobic material therbwith
JP2003268255A (en) * 2002-03-19 2003-09-25 Konica Corp Black color composition, dispersion of black fine particle, inkjet ink, and inkjet recording method

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