CN113214678B

CN113214678B - Environment-friendly disperse dye composition, disperse dye, and preparation method and application thereof

Info

Publication number: CN113214678B
Application number: CN202110500883.2A
Authority: CN
Inventors: 陆根发; 阮光栋; 景浙湖; 孙娴; 彭婷婷
Original assignee: Yorkshire Zhejiang Dyeing And Chemical Co ltd
Current assignee: Yorkshire Zhejiang Dyeing And Chemical Co ltd
Priority date: 2021-05-08
Filing date: 2021-05-08
Publication date: 2023-12-29
Anticipated expiration: 2041-05-08
Also published as: CN113214678A

Abstract

The invention provides an environment-friendly disperse dye composition, a disperse dye, a preparation method and application thereof. The disperse dye composition comprises the following components: component A of formula (I):a component B represented by the formula (II):

Description

Environment-friendly disperse dye composition, disperse dye, and preparation method and application thereof

Technical Field

The invention belongs to the field of dyes, and particularly relates to an environment-friendly disperse dye composition, a disperse dye, a preparation method and application thereof.

Background

In recent years, with the continuous improvement of health and environmental awareness of people, the requirements of consumers on the performance, the fastness grade and the ecological protection of textiles are also increasing. The environment-friendly dye can greatly improve the added value and competitiveness of the textile. For disperse dyes, there are currently a large number of disperse dyes in the market, such as: a low-temperature disperse dye formed by combining C.I. disperse yellow 64 and C.I. disperse yellow 54. However, the low-temperature disperse dye is not environment-friendly, contains substances which are harmful to the environment and human health, has the defect of poor sublimation fastness when printing and dyeing hydrophobic fibers, and cannot meet the market demand.

Therefore, an environment-friendly alternative dye is developed, and meanwhile, the performance of the dye is similar to that of the low-temperature dye, various color fastness are excellent, and a product with good compatibility has great market potential.

Disclosure of Invention

Problems to be solved by the invention

The invention provides an alternative low-temperature environment-friendly disperse dye composition, a disperse dye and a preparation method thereof, which are applied to printing and dyeing of hydrophobic fiber materials without multiple reduction cleaning, and dyed fibers have good washing fastness, perspiration fastness, friction fastness and excellent sublimation fastness.

Solution for solving the problem

The invention provides a disperse dye composition, which comprises the following components:

component A of formula (I):

a component B represented by the formula (II):

the disperse dye composition according to the invention, wherein the content of the component A is 5-95%, preferably 10-95%, based on 100% of the total mass of the disperse dye composition; the content of component B is 5 to 95%, preferably 5 to 90%.

The disperse dye composition according to the invention further comprises a component C shown as a formula (III) and/or a component D shown as a formula (IV);

the disperse dye composition according to the invention, wherein the content of the component A is 5-50%, preferably 5-45% based on 100% of the total mass of the disperse dye composition; the content of the component B is 5-50%, preferably 5-45%; the content of component C is 0-85%, preferably 5-85%; the content of component D is 0 to 80%, preferably 5 to 80%.

The invention also provides a disperse dye, which comprises the disperse dye composition and auxiliary materials; optionally, the auxiliary materials comprise an auxiliary agent and water.

The disperse dye according to the invention, wherein the mass ratio of the auxiliary agent to the disperse dye composition is 0.4-5:1;

preferably, the auxiliary agent comprises one or more than two of dispersing agent, dyeing auxiliary agent and surfactant;

more preferably, the auxiliary agent comprises one or more than two of naphthalene sulfonic acid formaldehyde condensate, alkyl naphthalene sulfonic acid formaldehyde condensate, benzyl naphthalene sulfonic acid formaldehyde condensate, lignosulfonate and sodium sulfate;

further preferably, the alkyl naphthalene sulfonic acid formaldehyde condensate comprises methyl naphthalene sulfonic acid formaldehyde condensate.

The invention also provides a preparation method of the disperse dye, wherein each dye component mixture is subjected to granulation treatment by a pulverizer in the presence of auxiliary materials; or the dye components are respectively subjected to granulation treatment by a pulverizer in the presence of auxiliary materials, and then are mixed.

The invention also provides an application of the disperse dye or the disperse dye prepared by the preparation method of the invention in dyeing and printing fabrics; preferably, the fabric comprises a hydrophobic fibrous material.

The invention also provides a fabric which is prepared by dyeing and printing by using the disperse dye or the disperse dye prepared by the preparation method.

ADVANTAGEOUS EFFECTS OF INVENTION

The low-temperature disperse dye composition and the disperse dye have the characteristics of safety and environmental protection, and under normal use conditions, the dye and the textile can meet the requirements of Oeko-Tex standard 100. And when being applied to dyeing of hydrophobic fiber materials, the color fastness is excellent.

In particular, the disperse dye composition and the disperse dye can obtain various color fastness higher than that of the traditional dye on hydrophobic fiber materials, and particularly have good washing fastness and sublimation fastness on light-colored fabrics.

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.

< first aspect >

In a first aspect the present invention provides a disperse dye composition comprising the following components:

component A of formula (I):

a component B represented by the formula (II):

further, in order to obtain a disperse dye composition having more excellent properties, the content of the component A is 5 to 95%, preferably 10 to 95%, based on 100% by mass of the total mass of the disperse dye composition; the content of component B is 5 to 95%, preferably 5 to 90%.

Specifically, the content of the component a may be 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95%, etc.; the component B may be present in an amount of 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, etc.

In some specific embodiments of the present invention, the disperse dye composition further comprises a component C as shown in formula (III) and/or a component D as shown in formula (IV);

preferably, the content of component A is from 5 to 50%, preferably from 5 to 45%, based on 100% of the total mass of the disperse dye composition; the content of the component B is 5-50%, preferably 5-45%; the content of component C is 0-85%, preferably 5-85%; the content of component D is 0 to 80%, preferably 5 to 80%.

Specifically, the content of the component a may be 15%, 20%, 25%, 30%, 35%, 40%, 45%, etc.; the content of the component B may be 10%, 15%, 20%, 25%, 30%, 35%, 40%, etc. The content of component C may be 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, etc.; the component D may be present in an amount of 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, etc.

In the present invention, the compounds represented by the formulae (I) to (IV) may be synthesized in a manner well known to those skilled in the art, or commercially available ones may be used.

The disperse dye composition and the disperse dye have excellent compatibility, and can be used for forming a yellow dye composition by using the component A and the component B or can be used for color matching with the component C and/or the component D, particularly when the component C and the component D are used for color matching, a gray dye composition is formed.

< second aspect >

In a second aspect the present invention provides a dye comprising a dye composition according to the first aspect and an auxiliary material. In some specific embodiments of the invention, the adjuvant comprises an adjuvant and water. In particular, the dye may be a yellow disperse dye and a gray disperse dye.

In some specific embodiments of the invention, the mass ratio of the auxiliary agent to the dye composition is from 0.4 to 5:1. Specifically, the mass ratio of the auxiliary agent to the disperse dye composition may be 0.5:1, 1:1, 2:1, 3:1, 4:1, 4.5:1, etc.

In some specific embodiments of the invention, the adjuvant comprises one or a combination of two or more of a dispersant, a dispersing agent, a dyeing auxiliary and a surfactant.

In the present invention, the specific kinds of the dispersant, the dispersing agent, the dyeing auxiliary and the surfactant are not particularly limited. May be dispersing agents, dyeing aids and surfactants commonly used in the art. Specifically, the dispersant may include one or a combination of two or more of naphthalene sulfonic acid formaldehyde condensate, alkyl naphthalene sulfonic acid formaldehyde condensate (e.g., methyl naphthalene sulfonic acid formaldehyde condensate, i.e., dispersant MF); the dispersing agent comprises one or more of benzyl naphthalene sulfonic acid formaldehyde condensate (dispersing agent CNF), lignin sulfonate and naphthalene sulfonic acid formaldehyde condensate (dispersing agent NNO); the dyeing auxiliary may include anhydrous sodium sulfate (sodium carbonate); the surfactant may include anionic surfactants, cationic surfactants, and the like.

In some specific embodiments of the invention, the auxiliary comprises one or a combination of more than two of naphthalene sulfonic acid formaldehyde condensate, alkyl naphthalene sulfonic acid formaldehyde condensate, benzyl naphthalene sulfonic acid formaldehyde condensate, sodium lignin sulfonate, naphthalene sulfonic acid formaldehyde condensate, sodium sulfate. Preferably, the alkyl naphthalene sulfonic acid formaldehyde condensate may include methyl naphthalene sulfonic acid formaldehyde condensate.

The dye composition or the dye provided by the invention is a safe and environment-friendly composite disperse dye with excellent color fastness.

< third aspect >

The invention further provides a preparation method of the dye according to the second aspect, which specifically comprises the following steps: in the presence of auxiliary materials, carrying out granulation treatment on each dye component mixture by using a pulverizer; or the dye components are respectively subjected to granulation treatment by a pulverizer in the presence of auxiliary materials, and then are mixed.

Specifically, in some specific embodiments of the present invention, the respective dye compound components of the dye composition are mixed in a specific ratio, and subjected to granulation treatment with a pulverizer such as a sand mill or a grinding machine in the presence of an auxiliary agent and water; in other embodiments of the present invention, the individual components of the dye composition may also be separately granulated in the presence of an auxiliary agent and water using a pulverizer such as a sand mill or a grinding mill, and mixed in a specific ratio after the granulation.

In some specific embodiments of the present invention, the dye is in a liquid state after being processed by a pulverizer such as a sand mill or a grinding mill, and the liquid dye may be dried, for example, spray dried, etc., to be made into a dry powder, a granule, etc.

< fourth aspect >

The fourth aspect of the present invention further provides the use of a dye composition according to the second aspect or a dye prepared by a method of preparation according to the third aspect for dyeing and/or printing fabrics.

In some specific embodiments of the invention, the fabric of the invention comprises a hydrophobic fiber fabric, preferably the fabric is a polyester fiber fabric.

In the present invention, the disperse dye may be dyed by a dyeing process conventionally used in the industry. The dyeing process comprises pad dyeing, jet dyeing and common dip dyeing.

The invention also provides a fabric prepared by dyeing and printing with the dye composition according to the second aspect of the invention or the dye prepared by the preparation method of the third aspect.

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 each embodiment of the invention, the dye composition inevitably contains a small amount of moisture and a small amount of physical impurities in the process of preparing the dye, belongs to a normal phenomenon, and does not influence the implementation of the technical scheme and the implementation of the technical effect.

Example 1

After mixing 14 g of the compound of formula (I), 12 g of the compound of formula (II) and 74 g of an auxiliary agent (12 g of sodium lignin sulfonate and 62 g of dispersing agent MF) with 150 g of water, the mixture was ground and dispersed by using a grinder and spray-dried to prepare yellow disperse dye products with excellent fastness properties.

Example 2

After mixing 21 g of the compound of formula (I), 15 g of the compound of formula (II) and 64 g of an auxiliary agent (20 g of sodium lignin sulfonate and 44 g of dispersant MF) with 150 g of water, the mixture was ground and dispersed by using a grinder and spray-dried to obtain yellow disperse dye products with excellent fastness properties.

Examples 3 to 6:

according to the structures and weights of the components A to B, the auxiliary agent and the water in Table 1, the components A to B, the auxiliary agent and the water were mixed to prepare a slurry by the method described in example 1 or 2, and the slurry was ground, dispersed and spray-dried to prepare a yellow disperse dye product.

Table 1 units: g

Example 7

After 9 g of the compound of formula (I), 7 g of the compound of formula (II), 25 g of the compound of formula (III), 24 g of the compound of formula (IV) and 35 g of dispersant MF were blended with 150 g of water, they were ground with a grinder to disperse and spray-dried to obtain gray disperse dye products excellent in each fastness property.

Examples 8 to 10:

the components A to D, auxiliaries and water were mixed to prepare slurries according to the structures and weights of the components A to D, auxiliaries and water in Table 1 by the method described in example 7, and the slurries were ground, dispersed and spray-dried to prepare grey disperse dye preparations.

Table 1 units: g

Comparative example 1:

16 g of C.I. disperse yellow 64, 13 g of C.I. disperse yellow 54 and 71 g of auxiliary agent (14 g of sodium lignin sulfonate and 57 g of dispersing agent MF) are added with 150 g of water, stirred uniformly, ground, dispersed and dried to obtain the finished dye.

Comparative example 2:

and adding 150 g of water into 8 g of C.I. disperse yellow 64, 5 g of C.I. disperse yellow 54, 27 g of a compound of formula (III), 25 g of a compound of formula (IV) and 35 g of a dispersing agent MF, uniformly stirring, grinding, dispersing and drying to obtain the finished dye.

Dyeing examples:

2.5 g of the disperse dyes prepared in examples 1 to 10 and comparative examples 1 to 2 were accurately weighed, dissolved, stirred uniformly, and fixed to a volume of 500 mL with a volumetric flask, 20 mL of dye liquor was sucked into a dyeing cup, 2 mL of a disperse leveling agent (manufacturer: joker's chemical industry control stock Co., model: deubao XLF) and 1 mL of acetic acid buffer (pH=4.5) were added, 77mL of water was then added, 5 g of polyester cloth was put in, and the dyeing depth (o.w.f) was controlled to 2.0% and the bath ratio was 1:20. Initially, the temperature was raised to 70 ℃ at a temperature rise rate of 3 ℃/min, then the temperature was raised from 70 ℃ to 130 ℃ at a temperature rise rate of 1.5 ℃/min, the temperature was kept for 50 min, and the temperature was lowered to 50 ℃ at a rate of 9.9 ℃/min to start sampling. And washing and drying the cloth sample to obtain the polyester fiber fabric.

And (3) testing various fastness:

the dyed polyester fiber fabrics were tested for fastness to washing, rubbing, sublimation and perspiration according to ISO 105-C10, ISO 105-X12, ISO 105-P01 and ISO 105-E04, respectively, and the results are shown in tables 1-4 below.

TABLE 1

TABLE 2

TABLE 3 Table 3

TABLE 4 Table 4

From the above data, it is clear that the dye finished products of examples 1 to 10 provided by the present invention have at least comparable or more excellent fastness properties when dyeing on polyester fiber fabrics, as compared with the dye finished products of comparative examples 1 to 2.

Environment protection test

The disperse dyes prepared in examples 1 to 10 and comparative examples 1 to 2 were each tested for their organochlorine carrier content according to DIN 54232:2010-08, and the results are shown in Table 5 below.

Table 5 units: mg/kg

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Note that: mg/kg=mg/kg nd=undetected limit=0.1 mg/kg

The dyes prepared in examples 1 to 10 and comparative examples 1 to 2 were dyed according to the method of dyeing example 1, and the resultant polyester fiber fabrics were respectively tested for the content of the organochlorine carrier according to the method of DIN 54232:2010-08, and the results are shown in Table 6 below.

Table 6 units: mg/kg

Note that: mg/kg=mg/kg nd=undetected limit=0.1 mg/kg

From the above data, it is clear that the dye finished products of examples 1 to 10 provided by the invention are compared with the dye finished products of comparative examples 1 to 2, and the dye-dyed polyester fiber fabric is compared with the dye finished products of comparative examples 1 to 10, so that the dye-dyed polyester fiber fabric has more excellent environmental protection performance, and can meet the environmental protection requirement of Oeko-Tex standard 100.

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

1. A disperse dye composition characterized by comprising the following components:

component A of formula (I):

a component B represented by the formula (II):

a component C represented by the formula (III) and a component D represented by the formula (IV):

the content of the component A is 5-45% based on 100% of the total mass of the disperse dye composition; the content of the component B is 5-45%; the content of the component C is 5-85%; the content of the component D is 5-80%.

2. A disperse dye, characterized in that it comprises a disperse dye composition according to claim 1 and an auxiliary material.

3. Disperse dye according to claim 2, characterized in that the auxiliary material comprises an auxiliary agent and water.

4. A disperse dye according to claim 3, characterized in that the mass ratio of auxiliary agent to disperse dye composition is 0.4-5:1.

5. The disperse dye according to claim 4, wherein the auxiliary agent comprises one or a combination of two or more of a dispersing agent, a dyeing auxiliary and a surfactant.

6. The disperse dye according to claim 5, wherein the auxiliary agent comprises one or a combination of more than two of naphthalene sulfonic acid formaldehyde condensate, alkyl naphthalene sulfonic acid formaldehyde condensate, benzyl naphthalene sulfonic acid formaldehyde condensate, lignin sulfonate and sodium sulfate.

7. The disperse dye according to claim 6, wherein the alkyl naphthalene sulfonic acid formaldehyde condensate comprises methyl naphthalene sulfonic acid formaldehyde condensate.

8. A process for the preparation of disperse dyes according to any one of claims 2 to 7, characterized in that the mixture of the dye components is subjected to a granulation treatment with a pulverizer in the presence of auxiliary materials; or the dye components are respectively subjected to granulation treatment by a pulverizer in the presence of auxiliary materials, and then are mixed.

9. Use of a disperse dye according to any one of claims 2 to 7 or a disperse dye prepared by a preparation method according to claim 8 for dyeing and printing textiles.

10. Use according to claim 9, characterized in that the fabric comprises a hydrophobic fibre material.

11. Fabric, characterized in that it is produced by dyeing and printing using the disperse dye according to any one of claims 2 to 7 or the disperse dye produced by the production method of claim 8.