CN111484752A

CN111484752A - Dye compound, dye composition, and preparation method and application thereof

Info

Publication number: CN111484752A
Application number: CN202010183926.4A
Authority: CN
Inventors: 张伟伟
Original assignee: Individual
Current assignee: Individual
Priority date: 2020-03-16
Filing date: 2020-03-16
Publication date: 2020-08-04

Abstract

The invention provides a dye compound, a dye composition, a preparation method and an application thereof. The dye compound has the following structural formulaShown in the figure:

Description

Dye compound, dye composition, and preparation method and application thereof

Technical Field

The invention relates to the field of dyes, in particular to a dye compound, a dye composition, and a preparation method and application thereof.

Background

The disperse yellow dyes commercially available and published in the literature are of a wide variety, and are typically: c.i. disperse yellow 114 and c.i. disperse yellow 246. In a printing and dyeing factory, c.i. disperse yellow 246 and disperse yellow 114 are used in a large amount as one of three primary colors of a high-fastness disperse dye.

However, because o-nitro-p-methoxyaniline (jujube red base GP) which is an intermediate for preparing C.I. disperse yellow 246 dye is a highly toxic chemical, the requirement in use is high, and meanwhile, the production of the raw materials of the disperse yellow 246 and the disperse yellow 114, namely the jujube red base GP and the m-aminophenol, relates to nitration reaction, the production difficulty is high, the danger is high, the treatment difficulty of the three wastes of the raw materials is high, and the raw materials are not easy to obtain; meanwhile, c.i. disperse yellow 114 and yellow 246 have low sublimation fastness and thus have limitations in application. However, c.i. disperse yellow 114 also has a number of problems, such as: the dye uptake is low, the lift force is poor, the dyeing residual liquid is dark, and the like, which are not beneficial to the treatment of dye wastewater, yellow 246 is golden yellow light, the sublimation fastness is low, the red light is heavy, and the application limitation is also large.

In addition, the existing other types of yellow disperse dyes have the problems of relatively poorer fastness in different degrees, harmful substances generated in the production process, environmental friendliness and the like.

In view of the above, the present invention is particularly proposed.

Disclosure of Invention

The invention aims to provide a dye compound, a dye composition, a preparation method and application thereof, so as to solve the problems.

In order to achieve the above purpose, the invention adopts the following technical scheme:

a dye compound having the general structural formula:

wherein R is₁Is selected from CH₃NH-、C₂H₅NH-、C₃H₇NH-、C₄H₉NH-、(CH₃)₂N-、(C₂H₅)₂N-、

R₂Selected from the group consisting of methyl, ethyl, propyl, butyl, benzyl, and methoxypropyl.

Preferably, the dye compound has the structural formula:

preferably, the dye compound has the structural formula:

a dye composition comprising one or more of said dye compounds.

Preferably, the dye composition further comprises a disperse red dye and/or a disperse blue dye.

Still further preferably, the disperse red dye comprises one or more of disperse red 4BS, disperse red 376, disperse red RS;

preferably, the disperse blue dye comprises one or more of disperse blue BFS, disperse blue BRS, disperse blue BGF.

Optionally, the dye composition further comprises an auxiliary agent.

A method for preparing the dye compound comprises the following steps:

and carrying out diazotization reaction on the raw material of the diazo part of the dye compound to obtain diazonium salt, and then adding the raw material of the coupling part to carry out coupling reaction to obtain the dye compound.

The dye compound and the application of the dye composition are used for dyeing acetate fiber fabrics, nylon fiber fabrics or polyester fiber fabrics.

Preferably, the dyeing temperature is 110-130 ℃ in the dyeing process of the polyester fiber fabric.

Compared with the prior art, the invention has the beneficial effects that:

the dye compound provided by the application has a special mother ring structure and R₁And R₂The substituted group has bright middle-green light yellow, high dye uptake, excellent dyeing performances such as color fastness, sublimation fastness, washing fastness and the like, does not contain forbidden aromatic amine, and is green and environment-friendly; the dye composition provided by the application is suitable for the requirements of various dyeing processes; the preparation method of the dye compound provided by the application is simple in process operation and mild in reaction condition; the dye compound and the dye composition provided by the application can be suitable for dyeing polyester fiber fabrics, polyamide fiber fabrics and acetate fiber fabrics, and have very wide application prospects.

Detailed Description

The terms as used herein:

"prepared from … …" is synonymous with "comprising". The terms "comprises," "comprising," "includes," "including," "has," "having," "contains," "containing," or any other variation thereof, as used herein, are intended to cover a non-exclusive inclusion. For example, a composition, process, method, article, or apparatus that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, process, method, article, or apparatus.

The conjunction "consisting of … …" excludes any unspecified elements, steps or components. If used in a claim, the phrase is intended to claim as closed, meaning that it does not contain materials other than those described, except for the conventional impurities associated therewith. When the phrase "consisting of … …" appears in a clause of the subject matter of the claims rather than immediately after the subject matter, it defines only the elements described in the clause; other elements are not excluded from the claims as a whole.

When an amount, concentration, or other value or parameter is expressed as a range, preferred range, or as a range of upper preferable values and lower preferable values, this is to be understood as specifically disclosing all ranges formed from any pair of any upper range limit or preferred value and any lower range limit or preferred value, regardless of whether ranges are separately disclosed. For example, when the range "1 ~ 5" is disclosed, the ranges described should be construed to include the ranges "1 ~ 4", "1 ~ 3", "1 ~ 2 and 4 ~ 5", "1 ~ 3 and 5", and the like. When a range of values is described herein, unless otherwise stated, the range is intended to include the endpoints thereof and all integers and fractions within the range.

In these examples, the parts and percentages are by mass unless otherwise indicated.

"part by mass" means a basic unit of measure indicating a mass ratio of a plurality of components, and 1 part may represent any unit mass, for example, 1g or 2.689 g. If we say that the part by mass of the component A is a part by mass and the part by mass of the component B is B part by mass, the ratio of the part by mass of the component A to the part by mass of the component B is a: b. alternatively, the mass of the A component is aK and the mass of the B component is bK (K is an arbitrary number, and represents a multiple factor). It is unmistakable that, unlike the parts by mass, the sum of the parts by mass of all the components is not limited to 100 parts.

"and/or" is used to indicate that one or both of the illustrated conditions may occur, e.g., a and/or B includes (a and B) and (a or B).

Embodiments of the present invention will be described in detail below with reference to specific examples, but those skilled in the art will appreciate that the following examples are only illustrative of the present invention and should not be construed as limiting the scope of the present invention. The examples, in which specific conditions are not specified, were conducted under conventional conditions or conditions recommended by the manufacturer. The reagents or instruments used are not indicated by the manufacturer, and are all conventional products available commercially.

Example 1

A dye compound having the structural formula:

the preparation method of the dye compound comprises the following steps:

and (2) diazotization, namely adding 210m L water and 43m L mass percent of hydrochloric acid into a reaction vessel, then adding 22.8g of p-benzenesulfonyl butylamine aniline under the stirring condition, pulping, then dropwise adding 24g of 30 mass percent sodium nitrite aqueous solution at 0-5 ℃, and reacting until diazotization components disappear.

Coupling reaction in a reaction vessel, 190m L of water, 18.5g of sodium carbonate and 24.4g of sodium carbonate are added

And (3) completely dissolving, adding a certain amount of crushed ice for cooling, slowly adding the diazo liquid obtained in the previous step, adjusting the pH of the system to be 8-9, reacting at 0-5 ℃ until diazonium salt disappears, filtering, collecting solids, washing with water to be neutral, and drying to obtain 44g of the target dye compound.

The dye compound is used for dyeing polyester fabrics to obtain bright medium-yellow colored fabrics.

Example 2

A dye compound having the structural formula:

the preparation method of the dye compound comprises the following steps:

diazotization reaction: the diazotization reaction process provided in example 1 was followed;

coupling reaction, namely, in a reaction vessel, adding 320m of L water and 10g of 30 percent NaOH aqueous solution in sequence, and adding 21.6g of NaOH aqueous solution into the reaction vessel under stirring

Stirring until the raw materials are completely dissolved, adding 17.5g sodium carbonate, stirring until the raw materials are completely dissolved, adding appropriate amount of crushed ice to cool, slowly adding diazo liquid obtained by the above reaction, adjusting the pH of the system to 5-6 at 0-5 deg.CAnd (3) reacting under the condition until the diazonium salt disappears, filtering and collecting a solid, washing to be neutral, and drying to obtain 41g of the target dye compound.

The dye compound is used for dyeing polyester fabrics to obtain bright green-light yellow fabrics.

Example 3

A dye compound having the structural formula:

the preparation method of the dye compound comprises the following steps:

the coupling reaction is carried out by adding 240m L water and 10g NaOH aqueous solution with mass fraction of 30% into a reaction vessel in sequence, stirring and adding 18.6g

And continuously stirring until the raw materials are completely dissolved, then adding 11g of sodium carbonate, stirring until the sodium carbonate is completely dissolved, then adding a proper amount of crushed ice to reduce the temperature, slowly adding a diazo liquid, adjusting the pH of the reaction system to be 7.5-8.5, reacting at the temperature of 0-5 ℃ until diazonium salt disappears, washing the solid obtained by filtering to be neutral, and drying to obtain 38.4g of the target dye compound.

Example 4

A dye compound having the structural formula:

the preparation method of the dye compound comprises the following steps:

and (2) diazotization, namely adding 230m L water and 43m L mass percent of hydrochloric acid into a reaction container, then adding 20.0g of p-benzenesulfonylethylaminoaniline under stirring, pulping for 2.5h, then adding a certain amount of crushed ice, cooling the reaction system, dropwise adding 24g of sodium nitrite aqueous solution with the mass percent of 30% at the temperature of 0-5 ℃, and reacting until diazo components disappear.

Coupling reaction into a three-necked flask, 210m L of water, 18.5g of sodium carbonate and 18.6g of sodium carbonate were added in this order

Stirring until the mixture is dissolved, then adding a proper amount of crushed ice for cooling, slowly adding the diazo liquid, adjusting the pH of the system to be 8-9, reacting at the temperature of 0-5 ℃ until diazo salt disappears, washing the solid obtained by filtering to be neutral, and drying to obtain 35.8g of the target dye compound.

Example 5

A dye compound having the structural formula:

the preparation method of the dye compound comprises the following steps:

and (2) diazotization reaction, namely adding 220m L water and 43m L mass percent of hydrochloric acid into a reaction container, then adding 18.6g of p-benzenesulfonyl methylamino aniline under the stirring condition, pulping for 3h, adding a proper amount of crushed ice to cool the system, slowly dropwise adding 24g of sodium nitrite aqueous solution with the mass percent of 30% at the temperature of 0-5 ℃, reacting until diazo components disappear, testing the bluish of potassium iodide test paper, and finishing the diazotization reaction.

Coupling reaction in a reaction vessel, 200m L of water, 19g of sodium carbonate and 18.6g of sodium carbonate were added in this order

Stirring until the mixture is dissolved, then adding a proper amount of crushed ice for cooling, slowly adding the diazo liquid, adjusting the pH of a reaction system to be 8-9, reacting at the temperature of 0-5 ℃ until diazo salt disappears, washing the solid obtained by filtering with water to be neutral, and drying to obtain 34.5g of the target dye compound.

Example 6

A dye compound having the structural formula:

the preparation method of the dye compound comprises the following steps:

diazotization reaction: the procedure for the diazotization reaction provided in example 5 was followed.

The coupling reaction is carried out by adding 250m L water and 10g NaOH aqueous solution with the mass fraction of 30 percent into a three-mouth bottle in turn, and adding 21g NaOH aqueous solution into the three-mouth bottle under the condition of stirring

And continuously stirring until the mixture is completely dissolved, then adding 10g of sodium carbonate, stirring until the mixture is completely dissolved, adding a proper amount of crushed ice to reduce the temperature, slowly adding a diazo liquid, adding liquid caustic soda to adjust the pH of the system to be 7.5-8, reacting at the temperature of 0-5 ℃ until diazo salt disappears, washing the solid obtained by filtering with deionized water, and drying to obtain 37g of the target dye compound.

Example 7

A dye compound having the structural formula:

the preparation method of the dye compound comprises the following steps:

and (2) diazotization, namely adding 210m L water and 44m L mass percent of 30% hydrochloric acid into a reaction vessel, adding 20.0g of p-benzenesulfonylethylaminoaniline under the stirring condition, pulping for 2.5h, adding a proper amount of crushed ice, reducing the temperature of a reaction system, dripping 24g of sodium nitrite aqueous solution with the mass percent of 30% at the temperature of 0-5 ℃, reacting until diazo components disappear, keeping a potassium iodide test paper bluish, and finishing the diazotization reaction.

Coupling reaction in a reaction vessel, 200m L of water, 18g of sodium carbonate and 21g of sodium carbonate are added in this order

Stirring until the mixture is dissolved, then adding a proper amount of crushed ice for cooling, slowly adding the diazo liquid, adjusting the pH of a reaction system to be 8-9, reacting at the temperature of 0-5 ℃ until diazo salt disappears, filtering and collecting a solid, filtering, washing with water to be neutral, and drying to obtain 38.4g of a target dye compound.

Example 8

A dye compound having the structural formula:

the preparation method of the dye composition comprises the following steps:

coupling reaction in a reaction vessel, 210m L of water, 18g of sodium carbonate and 24.5g of sodium carbonate were added in this order

Stirring until the mixture is dissolved, then adding a proper amount of crushed ice for cooling, slowly adding the diazo liquid, adjusting the pH of a reaction system to be 8-9, reacting at the temperature of 0-5 ℃ until diazo salt disappears, washing the filtered solid with deionized water, and drying until the solid is neutral to obtain 44g of the target dye compound.

Example 9

This example provides a method for preparing a commercial disperse dye, comprising the steps of:

10g of the dye compound prepared in example 1, 8g of a dispersing agent MF, 5g of sodium lignosulfonate and 55g of water are added into a sand mill, ground to a grade of 4-5 of diffusibility, and rapidly dried at 80 ℃ to obtain 25g of commercial yellow disperse dye.

200g of deionized water, 10g of pure cellulose acetate cloth and 0.2g of the commercial dye obtained in example 9 were added into a 500m L dyeing cup, the dyeing was carried out at a constant temperature of 85 ℃ for 45min, and the fabric was taken out, washed with water and soaped to obtain a bright green-yellow fabric.

The dye compounds of examples 2 to 8 were prepared in the same manner as above to give respective single-colored commercial disperse dyes.

Example 10

This example provides dye compositions comprising the dye compounds provided in examples 1 and 2.

The preparation method of the dye composition comprises the following steps: and uniformly mixing the obtained single-color commercial disperse dyes according to a certain proportion to obtain the dye composition.

The dye compounds provided in examples 1 to 8 can be mixed together at will to give different dye compositions.

Example 11

This example provides a dye composition comprising, in parts by weight, 28 parts of the dye compound provided in example 1, 26.6 parts of disperse red 4BS, and 45.4 parts of disperse blue BFS. After the three components are mixed, the color light of the color-changing agent is similar to the color light of the black SFN sold in the market, the intensity is equivalent to that of the black SFN sold in the market, and the fastness is better.

The structural formula of disperse red 4BS is:

the structural formula of the disperse blue BFS is as follows:

in addition, the dye compounds and combinations thereof provided in examples 1-8 can be used in combination with disperse red and disperse blue dyes. Wherein, disperse red RS can be used, and the structural formula is as follows:

disperse blue BRS, which has the formula:

in order to comparatively illustrate the performance of the commercial dye provided by the invention and the existing commercial dye in polyester dyeing, the commercial disperse dyes prepared from the dye compositions obtained in the examples and the disperse dyes of the comparative example 1 and the comparative example 2 are respectively adopted to dye pure polyester woven fabrics by a high-temperature high-pressure method, under the same dye concentration (2%), the bath ratio is 1: 20, the dyeing time is 45min, the dye uptake, the integer value and the sublimation fastness of different dyes at different dyeing temperatures (the sample is treated at 180 ℃ for 30s) are tested, and the six-fiber color fastness is measured.

Comparative example 1

Comparative example 1 the dye is now commercial disperse yellow 6GS L (c.i. disperse yellow 114) belonging to the high fastness series.

Wherein, the structural formulas of the dyes of C.I. disperse yellow 114 are respectively as follows:

comparative example 2

Comparative example 2 the dye is now commercially available disperse yellow 246, having the formula:

the test results of examples 1 to 8 and comparative examples 1 to 2 are shown in tables 1 and 2 below:

TABLE 1 dye uptake and Integ values for the different dyeing temperature treatments

As can be seen from the above Table 1, the disperse dye prepared from the dye compound provided by the invention is suitable for dyeing under the conditions of 110-130 ℃.

TABLE 2 sublimation fastness and six-fiber staining fastness for different dyeing temperature treatments

As can be seen from Table 2 above, the dye compounds provided by the present invention have sublimation fastness comparable to or slightly higher than that of the dyes provided by comparative examples 1-2, are superior to those of the comparative examples in terms of six-fiber color fastness, and have very high sublimation fastness and washing fastness.

The invention is calculated from the embodiment 1-8 and compared with the comparative example, the product has great cost performance advantage, while the performance is outstanding, the cost of the dye raw material of the invention of the embodiment 1-8 is about 4.5-5 ten thousand yuan per ton according to the market price, while the cost of the raw material of the comparative example 1 is about 7.5 ten thousand yuan, and the cost of the raw material of the comparative example 2 is about 8.9 ten thousand yuan.

The dye compound and the composition belong to medium-green yellow disperse dyes, have very high sublimation fastness and washing fastness, are bright in color, high in color yield, excellent in level-dyeing property, very high in dye uptake, good in cost performance, free of banned aromatic amine compounds, green and environment-friendly, and low in dye wastewater treatment cost after use.

Finally, it should be noted that: the above embodiments are only used to illustrate the technical solution of the present invention, and not to limit the same; while the invention has been described in detail and with reference to the foregoing embodiments, it will be understood by those skilled in the art that: the technical solutions described in the foregoing embodiments may still be modified, or some or all of the technical features may be equivalently replaced; and the modifications or the substitutions do not make the essence of the corresponding technical solutions depart from the scope of the technical solutions of the embodiments of the present invention.

Furthermore, those skilled in the art will appreciate that while some embodiments herein include some features included in other embodiments, rather than other features, combinations of features of different embodiments are meant to be within the scope of the invention and form different embodiments. For example, in the claims above, any of the claimed embodiments may be used in any combination. The information disclosed in this background section is only for enhancement of understanding of the general background of the invention and should not be taken as an acknowledgement or any form of suggestion that this information forms the prior art already known to a person skilled in the art.

Claims

1. A dye compound characterized by the general structural formula:

2. The dye compound according to claim 1, wherein the structural formula of the dye compound is:

3. the dye compound according to claim 1, wherein the structural formula of the dye compound is:

4. a dye composition comprising one or more of the dye compounds according to any one of claims 1 to 3.

5. The dye composition according to claim 4, further comprising a disperse red dye and/or a disperse blue dye.

6. The dye composition according to claim 5, wherein the disperse red dye comprises one or more of disperse red 4BS, disperse red 376 and disperse red RS;

7. Dye composition according to any one of claims 4 to 6, characterized in that it further comprises auxiliaries.

8. A method for producing the dye compound according to any one of claims 1 to 3, comprising:

9. Use of a dye compound according to any one of claims 1 to 3 and a dye composition according to any one of claims 4 to 7 for dyeing acetate fabrics, polyamide fabrics or polyester fabrics.

10. The use as claimed in claim 9, wherein the dyeing temperature during the dyeing of the polyester fiber fabric is 110-130 ℃.