Reactive Disperse Yellow Dye for Supercritical CO2 Dyeing and Methods of Production and Use Thereof

Abstract

A reactive disperse yellow dye is suitable for supercritical CO.sub.2 anhydrous dyeing. The reactive disperse yellow dye in has a parent of azo structure, and has monochlorometriazinyl groups thereon. The reactive disperse yellow dye can be used for supercritical CO.sub.2 anhydrous dyeing of cellulose fiber, protein fiber, chemical fiber and the blended fabrics thereof, and has good dyeing effect particularly for cotton-polyester blended products.

Claims

1. A reactive disperse yellow dye, having a structural according to formula I: ##STR00007## wherein R is C.sub.2H.sub.5 or C.sub.3H.sub.7.

2. A method for preparing the reactive disperse yellow dye according to claim 1, comprising following steps of: S1. dissolving N, N-dimethyl disperse dye II in a mixed solution of dioxane and water to obtain a N, N-dimethyl disperse dye II solution; dissolving cyanuric chloride in dioxane to obtain a mixture, followed by dropwise adding the mixture into the N, N-dimethyl disperse dye II solution, adjusting the solution's pH to 6 to 7 and conducting a reaction in an ice bath for 2 to 4 hours; after completion of the reaction, filtering a product, removing a solvent from the product, drying the product, and separating and purifying the product to obtain a N, N-dimethyl-s-triazine reactive disperse dye A; wherein the N, N-dimethyl disperse dye II has a structural according to formula II: ##STR00008## the N, N-dimethyl-s-triazine reactive disperse dye A has a structural according to formula A: ##STR00009## S2. dissolving the N, N-dimethyl-s-triazine reactive disperse dye A obtained in step S1 in a mixed solution of dioxane and water to obtain a N, N-dimethyl-s-triazine reactive disperse dye A solution; dissolving 4-ethylaniline or 4-propylaniline in dioxane to obtain a mixture, followed by dropwise adding the mixture into the N, N-dimethyl-s-triazine reactive disperse dye A solution, adjusting the solution's pH to 6 to 7 and conducting a reaction for 2.5 to 4.5 hours at 60 to 65° C.; after completion of the reaction, filtering a product, removing a solvent form the product, drying the product, and separating and purifying the product to obtain the reactive disperse yellow dye.

3. The method for preparing the reactive disperse yellow dye according to claim 1, wherein in step S1, a molar ratio of the N, N-dimethyl disperse dye II and the cyanuric chloride is 1:1 to 1:3; in step S2, a molar ratio of the N, N-dimethyl-s-triazine reactive disperse dye A and 4-ethylaniline or 4-propylaniline is 1:0.5 to 1:2.

4. The method for preparing the reactive disperse yellow dye according to claim 1, wherein in steps S1 and S2, a volume ratio of dioxane and water in the mixed solution of dioxane and water is 3:1; and the method for removing the solvent is rotary evaporation.

5. The method for preparing the reactive disperse yellow dye according to claim 1, wherein in steps S1 and S2, the drying is conducted at 60 to 80° C. for 12 hours.

6. The method for preparing the reactive disperse yellow dye according to claim 1, wherein in steps S1 and S2, sodium carbonate is used to adjust the pH to 7; and the separation and purification is to recrystallize the product by N, N-dimethylformamide.

7. A method for anhydrous dyeing, comprising dispersing the reactive disperse yellow dye in a supercritical CO.sub.2 fluid to form a dyeing medium; and dying a textile using the dyeing medium.

8. The method according to claim 7, further comprising adding 1 to 4% (o.w.f) of the reactive dispersive yellow dye and the supercritical CO.sub.2 fluid into a dye kettle; and placing the textile in the dyeing kettle to dye for 40 to 120 minutes at 80 to 140° C. under 16 to 26 MPa.

9. The method according to claim 7, wherein the textile is selected from cellulose fiber, protein fiber and chemical fiber, and a blended fabric thereof.

10. The method according to claim 9, wherein the cellulose fiber is cotton fiber or fibrilia, the protein fiber is wool fiber, and the chemical fiber is polyester; and the blended fabric is cotton-polyester blended fabric.

Description

DETAILED DESCRIPTION OF DRAWINGS

[0024] FIG. 1 shows the UV absorption spectrum of the dye A, dye C and dye D.

[0025] FIG. 2 shows the infrared spectrum of the dye A and dye C.

[0026] FIG. 3 shows the infrared spectrum of the dye A and dye D.

[0027] As shown in FIG. 2 and FIG. 3, the synthesized two reactive disperse dyes (dye C and dye D) appears an out-of-plane bending vibration peak of C—H on the benzene ring at 600 to 900 cm.sup.−1, an out-of-skeleton vibration peak of benzene ring at 1400-1600 cm.sup.−1, a stretching vibration absorption peak of C—Cl at 800 cm.sup.−1, and a stretching vibration absorption peak of —NH at 3440 cm.sup.−1.

[0028] FIG. 4 shows a HNMR spectrum of the dye C.

[0029] FIG. 5 shows a CNMR spectrum of the dye C.

[0030] FIG. 6 shows a HNMR spectrum of the dye D.

[0031] FIG. 7 shows a CNMR spectrum of the dye D.

DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS

[0032] The following non-limited embodiments enable those ordinary skilled in the art to understand the present disclosure more comprehensively, but do not limit the present disclosure in any way.

Embodiment 1

[0033] 4-nitroaniline (0.02 mol, 2.76 g) was dissolved in 120 mL water, the mixed solution was heated to 75° C. and 8 mL of concentrated hydrochloric acid was added in the mixed solution to make its pH to 3 to 4. After complete dissolution of the 4-nitroaniline, the solution was continued to stir for 0.5 hours, and then was cooled down to 0 to 5° C. in an ice bath. Sodium nitrite (0.022 mol, 1.52 g) was dissolved in 20 mL water, and the mixture was quickly added into the above solution to react. After 2 hours of reaction, Erich reagent was used to check whether the diazotization reaction was completed. After completion of the reaction, a small amount of sulphamic acid was added to remove excessive sodium nitrite, and starch KI test paper was used to check until the starch KI test paper did not change color within 1 to 2 seconds, to obtain a p-nitroaniline diazonium salt solution.

[0034] N, N-dimethylaniline (0.02 mol, 1.42 g) and sodium carbonate (0.02 mol, 2.21 g) were dissolved in a mixed solution of 80 mL water and 20 mL methanol. 4-nitroaniline diazonium salt was dropwise added into the N, N-dimethylaniline mixed solution in an ice bath and the pH thereof was adjusted to 7 with a 10% (o.m.f) sodium carbonate solution, followed by reacting for 2.5 hours. A product was filtered to obtain a solid product. The solid product was dried in a vacuum drying oven at 60° C. for 24 hours to obtain a coupling dye parent (5.3 g).

[0035] The coupling dye parent (2.66 g, 0.02 mol) was dissolved in 120 mL ethanol with stirring at 75° C. Sodium sulfide nonahydrate (4.8 g, 0.02 mol) and sodium bicarbonate (1.76 g, 0.02 mol) were dissolved in 20 mL water to obtain a mixture. The mixture was dropwise added into the coupling dye parent solution to obtain a mixed solution to react with quick stirring for 4 hours. There was only one reduction product point by detecting the reaction with thin layer chromatography (TLC for short, toluene:ethyl acetate=14:3, and R.sub.f=0.38). The reaction solution was cooled to room temperature and was conducted a vacuum filtration to obtain a N,N-dimethyl disperse dye (2.1 g).

[0036] N, N-dimethyl disperse dye (1.19 g, 0.005 mol) was dissolved in a mixed solution of 150 mL dioxane and 50 mL water. Cyanuric chloride (0.005 mol, 0.92 g) was dissolved in 50 mL dioxane and was dropwise added into the N, N-dimethyl disperse dye mixed solution, the pH thereof was adjusted to 7 with enough sodium carbonate, followed by reacting for 3 hours in an ice bath (0 to 5° C.). TLC (toluene:ethyl acetate=14:3 and R.sub.f=0.38) was used to check the reaction endpoint. A reaction product was filtered and conducted a rotary evaporation, and the product was dried in a vacuum oven at 60° C. for 12 hours. The product was collected to recrystallize and purify with DMF to remove impurities, and 1.95 g of the dye A was obtained. The equation is as follows:

##STR00004##

[0037] The dye A (0.002 mol, 0.75 g) was dissolved in a mixed solution of 150 mL dioxane and 50 mL water. 4-ethylaniline (0.268 g, 0.002 mol) was dissolved in 50 mL dioxane to obtain a mixture. The mixture was dropwise added into the dye A mixed solution and the pH thereof was adjusted to 7 with enough sodium carbonate, followed by reacting for 3 hours at 65° C. TLC (toluene:ethyl acetate=14:3 and R.sub.f=0.38) was used to check the reaction endpoint. A reaction product was filtered and conducted a rotary evaporation, and the product was dried in a vacuum oven at 60° C. for 12 hours. The products were collected to recrystallize and purify with DMF to remove impurities, and 0.76 g of 2-chloro-4-ethylaniline-s-triazine reactive disperse dye (dye C) was obtained. The equation is as follows:

##STR00005##

Embodiment 2

[0038] The synthesis method of the dye A refers to Embodiment 1.

[0039] The dye A (0.002 mol, 0.75 g) was dissolved in a mixed solution of 150 mL dioxane and 50 mL water. 4-propylaniline (0.268 g, 0.002 mol) was dissolved in 50 mL dioxane to obtain a mixture. The mixture was dropwise added into the dye A mixed solution and the pH thereof was adjusted to 7 with enough sodium carbonate, followed by reacting for 3 hours at 65° C. TLC (toluene:ethyl acetate=14:3 and R.sub.f=0.38) was used to check the reaction endpoint. A reaction product was filtered and conducted a rotary evaporation, and the product was dried in a vacuum oven at 60° C. for 12 hours. The products were collected to recrystallize and purify with DMF to remove impurities, and 0.76 g of 2-chloro-4-propylaniline-s-triazine reactive disperse dye (dye D) was obtained. The equation is as follows:

##STR00006##

Embodiment 3

[0040] A supercritical CO.sub.2 anhydrous dyeing method for cotton fabrics: 2% (o.w.f) of dye C was added into a dye kettle and cotton fabric to-be-dyed was placed into a dyeing kettle. The cotton fabric to-be-dyed was dyed at 120° C. and 24 MPa for 60 minutes by using supercritical CO.sub.2 fluid as the dyeing medium.

[0041] The K/S of the dyed cotton fabric is 6.8, and the color fastness to washing and the color fastness to rubbing are 4 to 5.

Embodiment 4

[0042] A supercritical CO.sub.2 anhydrous dyeing method for cotton fabrics: 2% (o.w.f) of dye D was added into a dye kettle and cotton fabric to-be-dyed was placed into a dyeing kettle. The cotton fabric to-be-dyed was dyed at 100° C. and 24 MPa for 60 minutes by using the supercritical CO.sub.2 fluid as the dyeing medium.

[0043] The K/S of the dyed cotton fabric is 5.7, and the color fastness to washing and the color fastness to rubbing are 4 to 5.

Embodiment 5

[0044] A supercritical CO.sub.2 anhydrous dyeing method for wool fibers: 2% (o.w.f) of dye C was added into a dye kettle and wool fiber to-be-dyed was placed into a dyeing kettle. The wool fiber to-be-dyed was dyed at 100° C. and 24 MPa for 60 minutes by using supercritical CO.sub.2 fluid as the dyeing medium.

[0045] The K/S of the dyed wool fiber is 4.2, and the color fastness to washing and the color fastness to rubbing are 4 to 5.

Embodiment 6

[0046] A supercritical CO.sub.2 anhydrous dyeing method for wool fibers: 4% (o.w.f) of dye D was added into a dye kettle and wool fiber to-be-dyed was placed into a dyeing kettle. The wool fiber to-be-dyed was dyed at 100° C. and 24 MPa for 60 minutes by using supercritical CO.sub.2 fluid as the dyeing medium.

[0047] The K/S of the dyed wool fiber is 5.3, and the color fastness to washing and the color fastness to rubbing are 4 to 5.

Embodiment 7

[0048] A supercritical CO.sub.2 anhydrous dyeing method for polyester/cotton (65/35, mass ratio) fabrics: 2% (o.w.f) of dye C was added into a dye kettle and the fabric to-be-dyed was placed in a dyeing kettle. The fabric to-be-dyed was dyed at 100° C. and 24 MPa for 60 minutes by using supercritical CO.sub.2 fluid as the dyeing medium.

[0049] The K/S of the dyed polyester/cotton fabric is 4.0, and the color fastness to washing and the color fastness to rubbing are 4 to 5.

Embodiment 8

[0050] A supercritical CO.sub.2 anhydrous dyeing method for polyester/cotton (65/35, mass ratio) fabrics:

[0051] 2% (o.w.f) of dye D was added into a dye kettle and the fabric to-be-dyed was placed into a dyeing kettle. The fabrics to-be-dyed was dyed at 100° C. and 24 MPa for 60 minutes by sing supercritical CO.sub.2 fluid as the dyeing medium.

[0052] The K/S of the dyed polyester/cotton fabric is 5.8, and the color fastness to washing and the color fastness to rubbing are 4 to 5.

Embodiment 9

[0053] A supercritical CO.sub.2 anhydrous dyeing method for polyester/cotton (50/50, mass ratio) fabrics: 4% (o.w.f) of dye D was added into a dye kettle and the fabric to-be-dyed was placed into a dyeing kettle. The fabric to-be-dyed was dyed at 130° C. and 24 MPa for 60 minutes by using the supercritical CO.sub.2 fluid as the dyeing medium.

[0054] The K/S of the dyed polyester/cotton fabric was 6.3, and the color fastness to washing and the color fastness to rubbing are 4 to 5.

Embodiment 10

[0055] A supercritical CO.sub.2 anhydrous dyeing method for polyester/cotton (50/50, mass ratio) fabrics: 2% (o.w.f) of dye D was added in a dye kettle and the fabric to-be-dyed, after pretreated with DMSO, was placed into a dyeing kettle, and the mangle expression was 80%. The fabric to-be-dyed was dyed at 120° C. and 25 MPa for 60 minutes by using supercritical CO.sub.2 fluid as the dyeing medium.

[0056] The K/S of the dyed polyester/cotton fabric is 8.2, and the color fastness to washing and the color fastness to rubbing are 4 to 5.

Embodiment 11

[0057] A supercritical CO.sub.2 anhydrous dyeing method for polyester/cotton (50/50, mass ratio) fabrics: 2% (o.w.f) of dye C was added into a dye kettle and the fabric to-be-dyed was placed into a dyeing kettle. The fabric to-be-dyed was dyed at 120° C. and 22 MPa for 60 minutes by using supercritical CO.sub.2 fluid as the dyeing medium.

[0058] The K/S of the dyed polyester/cotton fabric is 6.5, and the color fastness to washing and the color fastness to rubbing are 4 to 5.

[0059] It will be readily apparent to one skilled in the art that varying substitutions and modifications can be made to the invention disclosed herein without departing from the scope and spirit of the invention. Thus, such additional embodiments are within the scope of the present invention and the following claims. Therefore, any simple amendment, equivalent change and modification of the above embodiments according to the technical essence of the present disclosure, which is not separated from the content of the technical solution of the present disclosure, shall still fall within the scope of protection of the technical solution of the present disclosure.