CN118109063A - Disperse red dye composition and dye product - Google Patents

Disperse red dye composition and dye product Download PDF

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Publication number
CN118109063A
CN118109063A CN202211506027.9A CN202211506027A CN118109063A CN 118109063 A CN118109063 A CN 118109063A CN 202211506027 A CN202211506027 A CN 202211506027A CN 118109063 A CN118109063 A CN 118109063A
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CN
China
Prior art keywords
component
disperse red
red dye
dye composition
dye
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Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
CN202211506027.9A
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Chinese (zh)
Inventor
阮存凡
陈泽
沈杰
刘振涛
赵鹏
王专
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
ZHEJIANG LONGSHENG CHEMICAL RESEARCH CO LTD
Zhejiang Longsheng Group Co Ltd
Original Assignee
ZHEJIANG LONGSHENG CHEMICAL RESEARCH CO LTD
Zhejiang Longsheng Group Co Ltd
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Filing date
Publication date
Application filed by ZHEJIANG LONGSHENG CHEMICAL RESEARCH CO LTD, Zhejiang Longsheng Group Co Ltd filed Critical ZHEJIANG LONGSHENG CHEMICAL RESEARCH CO LTD
Priority to CN202211506027.9A priority Critical patent/CN118109063A/en
Publication of CN118109063A publication Critical patent/CN118109063A/en
Pending legal-status Critical Current

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Classifications

    • 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
    • C09B67/0079Azoic dyestuff preparations
    • 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
    • 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
    • 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
    • D06P3/8204Textiles which contain different kinds of fibres fibres of different chemical nature
    • D06P3/8214Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing ester and amide groups

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

Abstract

The invention provides a disperse red dye composition and a product thereof, comprising a component A and a component B, wherein the component A is selected from one or more of compounds shown in a formula (I), the component B is selected from one or more of compounds shown in a formula (II), and the dye and the product thereof have the characteristics of good washing fastness, rubbing fastness, bubble fastness and the like when being applied to dyeing of hydrophobic fiber materials.

Description

Disperse red dye composition and dye product
Field of the art
The invention relates to the field of disperse dyes, in particular to a high-fastness disperse red dye composition, a dye product and dyeing application of the dye product to hydrophobic fiber materials, particularly polyester and blended fabrics thereof.
(II) background art
In recent years, polyester-polyurethane blended fabrics are popular in the market because of better elasticity, wrinkle resistance, skin affinity and sweat absorption. Meanwhile, the cleaning condition of the blended fabric is not high, and the blended fabric can be cleaned by hand, machine and dry, so that the fabric is not damaged, and the requirements of sportswear and other middle-high-end clothing fabrics are met. At present, the blended fabric has the defects of poor stability and easy fading compared with pure polyester fabric. Therefore, the dye has higher requirements for coloring, wherein the disperse red dye is used as a color species with wider application, namely, can be used for monochromatic application and can be used for the compounding synergy of dark dye varieties. The color fastness and the lifting property of the red monochromatic and compound dye for the polyester-polyurethane blended fabric in the market at present are still to be further improved.
(III) summary of the invention
In order to solve the problems, the invention provides a disperse red dye composition and a dye product, which are applied to dyeing or printing of hydrophobic fiber materials, particularly polyester-polyurethane blended fabrics, have bright color, and have the characteristics of good lifting force, excellent fastness such as water washing resistance, sublimation resistance, friction resistance and the like, good bubble dropping performance and the like.
The technical scheme adopted by the invention is as follows:
A disperse red dye composition comprising a component a and a component B, wherein the component a is selected from one or more of the compounds of formula (I), the component B is selected from one or more of the compounds of formula (II), the mass percentage of the component a is 1 to 99% and the mass percentage of the component B is 1 to 99% based on the total weight of the component a and the component B:
In the above formula (I):
Each X 1、X2 is independently hydrogen, halogen, nitro or cyano;
R 1、R2 are each independently-CH 2COOK1 or-C 2H4COOK2, wherein K 1、K2 are each independently C 1~C4 alkyl;
In the above formula (II):
X 3、X4 are each independently hydrogen, nitro, cyano or halogen;
R 3 is-CH 2COOK3 or-C 2H4COOK4, wherein K 3、K4 is each independently C 1~C4 alkyl.
In the above formula (I) or formula (II), the C 1~C4 alkyl group may be methyl, ethyl, straight or branched propyl, straight or branched butyl. The halogen is Cl or Br.
Preferably, in the disperse red dye composition, the mass percentage of the component A is 1-50%, and the mass percentage of the component B is 50-99%; more preferably, the mass percentage of the component A is 1-25%, and the mass percentage of the component B is 75-99%.
Further, the disperse red dye composition of the present invention, component A is preferably at least one of the following formulas (I-1) to (I-13):
Even more preferably, component A is at least one of formulas (I-1), (I-2), (I-4), (I-8), (I-9) and (I-11).
The disperse red dye composition disclosed by the invention is preferable to be prepared from at least one of the following formulas (II-1) to (II-9):
Still more preferably, component B is at least one of the formulae (II-1) to (II-4) and (II-7) to (II-8).
Preferably, the disperse red dye composition consists of a component A and a component B, wherein the mass percentage of the component A is 1-50%, and the mass percentage of the component B is 50-99%.
As a further preference, the disperse red dye composition consists of a component a and a component B, wherein:
Component A is at least one of formulas (I-1), (I-2), (I-4), (I-8), (I-9) and (I-11);
the component B is at least one of formulas (II-1) to (II-4) and (II-7) to (II-8).
The disperse red dye composition of the invention generally requires the addition of conventional auxiliary agents in the commercialization process. Therefore, the invention also provides a disperse red dye product which contains the disperse red dye composition and an auxiliary agent, wherein the weight ratio of the auxiliary agent to the disperse red dye composition is 0.2-5:1. Preferably, the disperse red dye product consists of the disperse red dye composition and an auxiliary agent. The auxiliary agent is a dispersing agent, other surfactants and the like which are commonly used in disperse dye compounding, and is preferably one or a mixture of more than two of the following components: lignosulfonate (lignin 85A, lignin 83A, etc.), alkyl naphthalene sulfonic acid formaldehyde condensate (such as methyl naphthalene sulfonic acid formaldehyde condensate (dispersant MF)), naphthalene sulfonic acid formaldehyde condensate (dispersant NNO), benzyl naphthalene sulfonic acid formaldehyde condensate (dispersant CNF), anhydrous sodium sulfate, etc.
The preparation method of the disperse red dye product provided by the invention comprises the following steps: mixing dye monomer compounds (raw dyes) forming the disperse red dye composition according to a proportion, and then carrying out micropellet formation by using a pulverizer such as a sand mill or a grinding machine in the presence of an auxiliary agent and water; alternatively, the dye monomer compounds may be subjected to a fine particle formation treatment by 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 proportion. The disperse red dye preparation according to the invention is liquid after grinding by a sand mill or a grinding machine, and can be in powder or granule form after spray drying, which is a preparation method known to the person skilled in the art, since 100% removal of moisture is not possible during spray drying, a certain amount of moisture is allowed to exist in the dye preparation even in powder or granule form, preferably not more than 10% of the total weight of the dye preparation.
In addition, when the dye product is applied to dyeing of textile fibers, the technical feature contributing to the improvement of dyeing effect is the dye component and the proportion contained in the product.
The disperse red dye composition provided by the invention also allows the disperse red dye composition to be further compounded and synergized with other dyes to prepare a new dye variety.
In the present invention, the dye compounds represented by the formula (I) and the formula (II) can be conveniently synthesized by diazotization and coupling methods well known to those skilled in the art, and commercially available products can be used.
The invention also provides application of the disperse red dye product in dyeing or printing of hydrophobic fiber materials.
The dye product prepared by the dye composition can be used for dyeing hydrophobic fiber materials (such as polyester and blended fabrics thereof, such as polyester/ammonia fabrics) in a manner conventional in 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 pretreated hydrophobic fiber material into a dye vat for dip dyeing, washing the dyed hydrophobic fiber material to be neutral by cold water, wringing the hydrophobic fiber material, carrying out reduction washing and drying the hydrophobic fiber material; and (3) directly printing, namely, carrying out dyeing pretreatment on the fabric, drying, setting, printing disperse dye color paste on a printing machine, steaming, fixing the dye on the fabric by utilizing a steaming mode, washing with water, and tentering and setting.
The disperse red dye composition and the dye product provided by the invention are used for dyeing or printing hydrophobic fiber materials, have bright color, have good lifting power, and have the characteristics of excellent fastness such as water washing resistance, sublimation resistance, friction resistance and the like, good blister dropping performance and the like.
(IV) detailed description of the invention
The invention will be further described with reference to the following specific examples, but the scope of the invention is not limited thereto:
example 1:
20 g of dye shown in formula (I-1), 80 g of dye shown in formula (II-1) and 250 g of dispersing agent MF are mixed together by adding 2000 g of water, and then are ground, dispersed and dried to obtain a finished product, and the finished product can provide red color tone for polyester and blended fabrics thereof.
Example 2:
50g of dye shown in formula (I-1), 50g of dye shown in formula (II-2) and 200 g of sodium lignin sulfonate are mixed with 2000 g of water, and then are ground, dispersed and dried to obtain a finished product, and the finished product can provide red color tone for polyester and blended fabrics thereof.
Example 3:
12 g of dye shown in formula (I-1), 88 g of dye shown in formula (II-3), 200 g of dispersing agent MF and 50 g of sodium lignin sulfonate are mixed together by adding 2500 g of water, and then are ground, dispersed and dried to obtain a finished product, and the finished product can provide polyester and the red color tone of the blended fabric.
Examples 4 to 25
According to the method described in examples 1-3, except that 200 g of auxiliary agent (150 g of dispersing agent MF and 50 g of sodium lignin sulfonate) and 2000 g of water are added to the components A and B shown in Table 1, and the components A and B are blended to prepare slurry, and the slurry is ground, dispersed and dried to prepare the finished product, wherein the dye can provide red color tone with excellent fastness properties for polyester and blended fabrics thereof.
TABLE 1
Dyeing examples:
2g of the disperse red dye prepared in examples 1-25 is weighed respectively, the polyester-spandex knitted fabric is treated by a conventional high-temperature high-pressure dyeing method and a heat setting method, in the treatment process, the dyeing depth (o.w.f) is controlled to be 4.0 percent, the bath ratio is controlled to be 1:40, the pH value of a dyeing bath is regulated to be 4-5, the dyeing is carried out at room temperature, the temperature is increased to 130 ℃ at 1 ℃/min, the dyeing is carried out for 30min, and the red dyed fabric is obtained by washing, reduction cleaning (flake alkali 2g/L, sodium hydrosulfite 3g/L and sodium hydrosulfite 85 ℃ x20 min) and acid washing neutralization (acetic acid 2g/L and 40 ℃ x 15 min) through water washing and drying and heat setting for 30 seconds at 180 ℃. The fastness to rubbing, to sublimation and to washing were tested according to ISO 105-X12, ISO 105-P01, ISO 105-C10, respectively. In addition, after 2g of red dyed fabric and 2g of white cloth with the same specification are sewed, the fabric is soaked in 95 ℃ (5 g/L of washing powder) for 15min, the bath ratio is 1:50, the dyeing grade of the light and heavy falling color and the white cloth is judged, and the water bubble falling color fastness is evaluated. The results of the above test are shown in table 2 below.
TABLE 2
Therefore, the disperse red dye composition and the dye product thereof have excellent fastness, particularly excellent washing fastness and bubble drop fastness, and can meet the high-fastness requirement of fabric printing and dyeing.

Claims (10)

1. A disperse red dye composition comprising a component a and a component B, wherein the component a is selected from one or more of the compounds of formula (I), the component B is selected from one or more of the compounds of formula (II), the mass percentage of the component a is 1 to 99% and the mass percentage of the component B is 1 to 99% based on the total weight of the component a and the component B:
In the above formula (I):
Each X 1、X2 is independently hydrogen, halogen, nitro or cyano;
R 1、R2 are each independently-CH 2COOK1 or-C 2H4COOK2, wherein K 1、K2 are each independently C 1~C4 alkyl;
In the above formula (II):
X 3、X4 are each independently hydrogen, nitro, cyano or halogen;
R 3 is-CH 2COOK3 or-C 2H4COOK4, wherein K 3、K4 is each independently C 1~C4 alkyl.
2. The disperse red dye composition of claim 1, wherein: the C 1~C4 alkyl group can be methyl, ethyl, straight or branched propyl, straight or branched butyl; the halogen is Cl or Br.
3. The disperse red dye composition of claim 1, wherein: the mass percentage of the component A is 1-50%, and the mass percentage of the component B is 50-99%.
4. The disperse red dye composition according to claim 1, wherein the component A is at least one selected from the following formulas (I-1) to (I-13):
5. disperse red dye composition according to claim 1, wherein component B is preferably selected from at least one of the following formulae (ii-1) to (ii-9):
6. The disperse red dye composition according to claim 4, wherein component A is at least one of formulas (I-1), (I-2), (I-4), (I-8), (I-9) and (I-11).
7. The disperse red dye composition according to claim 5, wherein the component B is at least one of the formulas (II-1) to (II-4) and (II-7) to (II-8).
8. The disperse red dye composition according to claim 1, which consists of a component A and a component B, wherein the mass percentage of the component A is 1-50%, and the mass percentage of the component B is 50-99%.
9. A disperse red dye product comprises an auxiliary agent and the disperse red dye composition as defined in claim 1, wherein the weight ratio of the auxiliary agent to the disperse red dye composition is 0.2-5:1, and the auxiliary agent is a dispersing agent, a dispersing agent or other surfactants commonly used in disperse dye compounding: naphthalene sulfonic acid formaldehyde condensate, lignin sulfonate, alkyl naphthalene sulfonic acid formaldehyde condensate, benzyl naphthalene sulfonic acid formaldehyde condensate, sodium lignin sulfonate, and anhydrous sodium sulfate.
10. Use of the disperse red dye composition according to claim 1 or the disperse red dye article according to claim 9 for dyeing hydrophobic fiber materials.
CN202211506027.9A 2022-11-29 2022-11-29 Disperse red dye composition and dye product Pending CN118109063A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202211506027.9A CN118109063A (en) 2022-11-29 2022-11-29 Disperse red dye composition and dye product

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202211506027.9A CN118109063A (en) 2022-11-29 2022-11-29 Disperse red dye composition and dye product

Publications (1)

Publication Number Publication Date
CN118109063A true CN118109063A (en) 2024-05-31

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Family Applications (1)

Application Number Title Priority Date Filing Date
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Country Status (1)

Country Link
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