Dye for dyeing cotton fiber in supercritical carbon dioxide, preparation method and application thereof

Abstract

The present disclosure discloses a dye for industrialization of dyeing cotton fiber in supercritical carbon dioxide that can react with cotton fiber, wherein a preparation method therefor comprises the following steps: dissolving a hydroxyl-containing natural dye in an organic solvent, dropwise adding an alcohol compound containing a halogen group into a reaction system in the presence of an acid-binding agent, precipitating the product with another solvent after the reaction is completed, and then filtrating and drying to obtain the compound described. The obtained compound is used for dyeing cotton fiber in supercritical carbon dioxide. The dye provided by the present disclosure is capable of dyeing cotton fiber in supercritical carbon dioxide conditions, and has a better color fastness while dyeing the cotton fiber.

Claims

1. A hydroxyalkyl-containing dye, having a structure according to formula I: ##STR00005## wherein R.sub.1 is hydroxyalkyl having a structure of CH.sub.2.sub.nOH, and n is 3, 4, or 5.

2. A preparation method of the dye according to claim 1, comprising: dissolving a hydroxyl-containing natural dye in an organic solvent to form a solution; adding an alcohol compound containing a halogen group and adding an acid-binding agent into the solution; precipitating a product from the solution using water; and filtrating the product and drying the product to obtain the hydroxyalkyl-containing dye, wherein the hydroxyl-containing natural dye is curcumin; and the alcohol compound containing halogen group has a structure of XCH.sub.2.sub.kOH, X chlorine, bromine, or iodine, and k is 3, 4, or 5.

3. The preparation method according to claim 2, wherein the organic solvent is N,N-dimethylformamide, dimethyl sulfoxide, or acetone.

4. The preparation method according to claim 2, wherein the acid-binding agent is potassium carbonate or sodium carbonate.

5. The preparation method according to claim 2, wherein the drying is vacuum drying at 50 to 80 C.

6. A dyeing method, comprising crushing the dye of claim 1 into 10 to 100 mesh in size; adding the crushed dye, cotton fiber, and supercritical carbon dioxide into a supercritical carbon dioxide dyeing device to form a mixture; heating the mixture in the dyeing device to a temperature of 50-150 C.; increasing a pressure in the dyeing device to 12-35 MPa; maintaining the temperature at 50-150 C. and the pressure at 12-35 MPa for 30-150 min; reducing the pressure to 4-5 MPa; recovering carbon dioxide and the dye from the dyeing device at 25-40 C.; and releasing the pressure and cooling the temperature to obtain dyed cotton fiber.

Description

BRIEF DESCRIPTION OF THE DRAWINGS

(1) FIG. 1 illustrates a flow chart of supercritical fluid dyeing;

(2) wherein, 1dyeing kettle, 2dye kettle, 3separator, 4circulating pump, 5high pressure pump, 6refrigeration machine.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

(3) The following embodiments enable those skilled in the art to more comprehensively understand the present disclosure, but the present disclosure is not limited in any way.

Embodiment 1

(4) 20 mL N,N-dimethylformamide and 1.09 g curcumin were added into a 50 mL three-necked flask, the three-necked flask was put into a 40 C. constant-temperature water bath, the curcumin was completely dissolved under stirring, and then 1.2 g anhydrous potassium carbonate was added, to make the reaction solution become reddish-brown. Then 2 mL 4-bromobutanol was dropwise added, after the 4-bromobutanol was completely added into the reaction system, the temperature of the constant-temperature water bath was raised to 80 C., and the reaction was continued for 5 h, and the color of the reaction solution gradually turned into bright yellow. Grafting reaction was monitored by TLC (by volume ratio, a developing solvent to ethyl acetate to petroleum ether is 1 to 3) until no curcumin point appeared in the reactant, which indicates that the grafting reaction was ended.

(5) 50 mL water was added into a 100 mL beaker, 22 mL bright yellow reaction solution containing the product was poured into the water under stirring, and the reaction product was fully precipitated in the water under stirring for 1 h. Then, the mixture was filtered, and dried in a vacuum drying oven at 60 C. for 12 h to obtain a product 1, wherein the yield was 55.9%. Spectrogram data of the product 1 was as follows: ES-API (m/z (%)): 255.12 (199) [M-2H].sup.2/2; 1H NMR (400 MHz, DMSO-d6): 7.56 (d, J=15.8 Hz, 2H, H-j and H-D, 7.33 (d, J=1.9 Hz, 2H, H-I and H-i), 7.16 (dd, J=8.1, 1.9 Hz, 2H, H-h and H-h), 6.84 (d, J=8.1 Hz, 2H, H-g and H-g), 6.76 (d, J=15.8 Hz, 2H, H-k and H-k), 6.07 (s, 1H, H-l), 3.85 (s, 6H, H-f and H-f), 3.83 (obscured signal, 4H, H-b and H-b), 2.56 (t, J=5.5 Hz, 4H, H-e and H-e), 2.51 (m, 10H, H-a, H-a, H-c, H-c, H-d and H-d); IR (KBr): 3231 cm.sup.1 (OH), 2938 cm.sup.1 (.sub.C-H), 1629 cm.sup.1 (.sub.CO), 1588 cm.sup.1 (.sub.CC aromatic ring), 1513 cm.sup.1 (.sub.CC aromatic ring), 1449 cm.sup.1 (.sub.C-H in-plane deformation), 1291 cm.sup.1 (.sub.C-H in-plane deformation), 1263 cm.sup.1 (.sub.C-O-C), 1119 cm.sup.1 (.sub.C-O-C), 846 cm.sup.1 (.sub.C-H aromatic ring), 805 cm.sup.1 (.sub.C-H aromatic ring), 714 cm.sup.1 (.sub.-(CH)4-)

(6) ##STR00002##

Embodiment 2

(7) 20 mL N,N-dimethylformamide and 1.09 g curcumin were added into a 50 mL three-necked flask, the three-necked flask was put into a 40 C. constant-temperature water bath, the curcumin was completely dissolved under stirring, and then 2.4 g anhydrous sodium carbonate was added to make the reaction solution become reddish-brown. Then 2 mL 4-bromobutanol was dropwise added, after the 4-bromobutanol was completely added into the reaction system, a temperature of the constant-temperature water bath was raised to 80 C., and the reaction was continued for 5 h.

(8) 50 mL water was added into a 100 mL beaker, 22 mL bright yellow reaction solution containing the product was poured into the water under stirring, and the reaction product was fully precipitated in the water under stirring for 1 h. Then, the mixture was filtered and dried in a vacuum drying oven at 60 C. for 12 h to obtain the product 1, wherein the yield was 54.1%.

Application Example 1

(9) 1 g product 1 was crushed into 80 mesh size in a fineness crusher and then was placed in a dye kettle of a supercritical carbon dioxide dyeing device (the flow chart was shown in FIG. 1), loose cotton fiber was placed in a dyeing kettle, closed the dyeing kettle, supercritical carbon dioxide was filled in the supercritical dyeing device, the system temperature was increased to 150 C. by heating, opened the high-pressure system to make the pressure be 26 Mpa, then the dye was dissolved and dyeing was performed under this condition for 110 min; then the pressure was reduced to 4-5 MPa, and carbon dioxide and the dye were recovered at 25-40 C.; then the pressure was released again and the temperature was reduced to a normal state; opened the dyeing kettle was to obtain dyed cotton fiber. The dyed cotton fiber was washed with acetone and then washed with water, and the color fastness of the obtained fiber was tested (see Table 1).

Embodiment 3

(10) 20 mL N,N-dimethylformamide and 1.09 g curcumin were added into a 50 mL three-necked flask, the three-necked flask was put into a 40 C. constant-temperature water bath, the curcumin was completely dissolved under stirring, and then 1.2 g anhydrous potassium carbonate was added to make the reaction solution become reddish-brown. Then 2 mL 3-bromopropanol was dropwise added; after the 3-bromopropanol was completely added into the reaction system, the temperature of the constant-temperature water bath was raised to 80 C., the reaction was continued for 5 h, and the color of the reaction solution gradually turned into bright yellow.

(11) 50 mL water was added into a 100 mL beaker, 22 mL bright yellow reaction solution containing the product was poured into the water under stirring, and the reaction product was fully precipitated in the water under stirring for 1 h. Then, the mixture was filtered, and dried in a vacuum drying oven at 60 C. for 12 h to obtain a product 2, wherein the yield was 61.2%.

(12) ##STR00003##

Embodiment 4

(13) 20 mL N,N-dimethylformamide and 1.09 g curcumin were are added into a 50 mL three-necked flask, the three-necked flask was put into a 40 C. constant-temperature water bath, the curcumin was completely dissolved under stirring, and then 2.4 g anhydrous sodium carbonate was added to make the reaction solution become reddish-brown. Then 2 mL 3-bromopropanol was dropwise added; after the 3-bromopropanol was completely added into the reaction system, the temperature of the constant-temperature water bath was raised to 80 C., and the reaction was continued for 5 h.

(14) 50 mL water was added into a 100 mL beaker, 22 mL bright yellow reaction solution containing the product was poured into the water under stirring, and the reaction product was fully precipitated in the water under stirring for 1 h. Then, the mixture was filtered, and dried in a vacuum drying oven at 60 C. for 12 h to obtain the product 2, wherein the yield was 66.1%.

Application Example 2

(15) 1 g product 2 was crushed into 80 mesh size in a fineness crusher and then was placed in a dye kettle of a supercritical carbon dioxide dyeing device (the flow chart was shown in FIG. 1), loose cotton fiber was placed in a dyeing kettle, closed the dyeing kettle, supercritical carbon dioxide was filled in the supercritical dyeing device, the system temperature was increased to 140 C. by heating, opened the high-pressure system to make the system pressure be 25 Mpa, then the dye was dissolved and dyeing was performed under this condition for 120 min; then the pressure was released to 4-5 MPa, and carbon dioxide and the dye were recovered at 25-40 C.; and the pressure was released again, the temperature was reduced to a normal state, and the dyeing kettle was opened to obtain dyed cotton fiber. The dyed cotton fiber was washed with acetone and then washed with water, and the color fastness of the obtained fiber was tested (see Table 1).

Embodiment 5

(16) 20 mL N,N-dimethylformamide and 1.09 g curcumin were added into a 50 mL three-necked flask, the three-necked flask was put into a 40 C. constant-temperature water bath, the curcumin was completely dissolved under stirring, and then 1.2 g anhydrous potassium carbonate was added to make the reaction solution become reddish-brown. Then 2 mL 5-bromopentanol was dropwise added; after the 5-bromopentanol was completely added into the reaction system, the temperature of the constant-temperature water bath temperature was raised to 80 C., the reaction was continued for 5 h, and a color of the reaction solution gradually turned into bright yellow.

(17) 50 mL water was added into a 100 mL beaker, 22 mL bright yellow reaction solution containing the product was poured into the water under stirring, and the reaction product was fully precipitated in the water under stirring for 1 h. Then, the mixture was filtered, and dried in a vacuum drying oven at 60 C. for 12 h to obtain a product 3, wherein the yield was 43.8%.

(18) ##STR00004##

Embodiment 6

(19) 20 mL N,N-dimethylformamide and 1.09 g curcumin were added into a 50 mL three-necked bottle, the three-necked bottle was put into a 40 C. constant-temperature water bath, the curcumin was completely dissolved under stirring, and then 2.4 g anhydrous sodium carbonate was added to make the reaction solution become reddish-brown. Then 2 mL 5-bromopentanol was dropwise added; after the 5-bromopentanol was completely added into the reaction system, the temperature of the constant-temperature water bath was raised to 80 C., and the reaction was continued for 5 h.

(20) 50 mL water was added into a 100 mL beaker, 22 mL bright yellow reaction solution containing the product was poured into the water under stirring, and the reaction product was fully precipitated in the water under stirring for 1 h. Then, the mixture was filtered, and dried in a vacuum drying oven at 60 C. for 12 h to obtain the product 3, wherein the yield was 39.8%.

Application Example 3

(21) 1 g product 3 was crushed into 100 meshes in a fineness crusher and then was placed in a dye kettle of a supercritical carbon dioxide dyeing device (the flow chart was shown in FIG. 1), loose cotton fiber was placed in a dyeing kettle, closed the dyeing kettle, supercritical carbon dioxide was filled in the supercritical dyeing device, the system temperature was increased to 130 C. by heating, opened the high-pressure system to make the pressure of the mixture be 24 Mpa, then the dye was dissolved and dyeing was performed under this condition for 110 min; then the pressure was released to 4-5 MPa, and carbon dioxide and the dye were recovered at 25 40 C.; and the pressure was released again, the temperature was reduced to a normal state, and the dyeing kettle was opened to obtain dyed cotton fiber. The dyed cotton fiber was washed with acetone and then washed with water, and the color fastness of the obtained fiber was tested (see Table 1).

(22) TABLE-US-00001 TABLE 1 Washing fastness Application Color Cotton Fur Rubbing fastness example change staining staining Dry Wet 1 4 4-5 4-5 4 4 2 4-5 5 4-5 5 4-5 3 4 4 4-5 4 3-4 Comparison* 4 3 4-5 4 3 *Ji Ting, Study on one-step extracting-dyeing technology of Supercritical CO.sub.2 of Natural Dye, Thesis of Master's Degree, Dalian Institute of Light Industry, 2007