Dyeing Cationic Cotton with Fiber Reactive
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peerreviewed
Hale Waihona Puke Baidu
Dyeing Cationic Cotton with Fiber Reactive Dyes: Effect of Reactive Chemistries
By Peter J. Hauser and Adham H. Tabba, North Carolina State University, Raleigh Dyeing cotton with fiber reactive dyes is for water solubility, the electrostatic intercurrently a high energy consuming, water action between a positively charged fiber intensive, pollution generating process. and negatively charged dye molecules Since cotton has only a moderate affinity can substantially increase the affinity of for most fiber reactive dyes, high concen- dyes for the fiber and reduce the need for trations of electrolytes and extended dye- dyebath electrolytes. Numerous studies ing cycles at high temperatures are needed have reported a variety of chemicals that to achieve reasonable dye exhaustion. Al- can impart a cationic charge to cotton though significant improvements in dye- fibers.^"" Of particular interest is 2,3fiber affinities have been realized with new epoxypropyltrimethylammonium chlodye molecules, dyebath electrolytes are still ride, a product that has been shown to needed. Since the reactive groups in fiber be able to provide a cotton fabric with reactive dyes can react with water as well greatly enhanced affinity for anionic dyes as with the cotton fiber, this unavoidable with resulting reduced environmental hydrolysis leaves unfixed dye molecules impact, lower energy consumption, and that must be removed by multiple rinses increased dyehouse productivity (Fig. and after-washing in order to meet washfastness requirements. As a result, the This work looks at dyeing cotton typical cotton dyehouse discharges high modified with 2,3-epoxypropyltnmethylvolumes of wastewater containing signifi- ammonium chloride with commercially cant amounts of dyes and chemicals. available fiber reactive dyes having a vaModifying cotton fibers with cationic riety of reactive groups to determine how charges prior to dyeing is an attractive the structure of the reactive groups afroute to improving dye-fiber affinity. Since fiber reactive dyes contain anionic groups CH3
1
Key Terms Cationic Cotton Dyeing Reactive Dyes
AATCC REVIEW Bifunctional-bisnicotinotriazine
Bifunctional - vinyl sulfone/pyrimidine
36
peerreviewed
Cl. F chlorodifluoropyrimidine monofluorotriazine
ABSTRACT
fects color yields and colorfastness of the dyed fabric.
EXPERIMENTAL
Materials
The fabric used for all the dyeings was a 100% cotton single jersey knit that had been scoured and bleached before cationization or dyeing. The use of absorbent fabric eliminated the need for wetting agents in the pretreatment or dyebaths. 3-chloro-2-hydroxypropyltri methylammonium chloride is commercially available as a 65% solution in water and was used as received. The dyes in this study (Table I) were all obtained from commercial sources and were used as received. These dyes were chosen because of their commercial availability and known reactive groups. Vinyl sulfone dyes, a major reactive dye chemistry, were evaluated in CH3 -OCH2CHCH2N-CH3 OH CH3
-D-UV/ -^ N ^
S-CH2CH2OSO3 nicotinotriazine O
vinylsulfone
and held at that temperature for 45 mm. The fabric was then removed from the bath and rinsed once with 50C water, once with a 1-g/L acetic acid solution at 50C, and once again with 50C water. A 1 -g/L scouring agent solution was added to a dyeing can with the dyed fabric, heated to 90C at 3C/min, and held at that temperature for 10 min. The fabric was removed from the scouring bath and rinsed with 60C water until a clear rinse achieved. The fabric was allowed to air dry. Procedure 2
Fig. 1. Reaction of 2,3-epoxypropyltrimethylammonium chloride with cellulose.
TABLE 1.
Dyes Used in this Study Reactive Functionality Chlorodifluoropyrimidine Monofluorotriazine Colour Index Number Reactive Red 147 Reactive Blue 209 Reactive Orange 91 Reactive Red 184 Reactive Blue 182 Reactive Yellow 162 Reactive Red 221 Reactive Blue 217 not available
-D-|— Fig. 2. Reactive groups for fiber reactive dyes.
dye molecule
Procedure 2 was used with the bifunctional-bisnicotinotriazine dyes for conventional cotton. The appropriate amounts of salt and dye (Table II) were added to a room temperature bath earlier work.'' Commercially available so- Dyeing Procedures (~22C) in a dyeing can. Fabric, wetted dium hydroxide (50% solution), acetic All of the dyeings were done in a Mathis with water, was added to the can, and acid (97%), sodium carbonate, sodium Labomat laboratory dyeing machine at a the can was sealed. Immediately, the bath sulfate, and sodium chloride were used as 13.3:1 liquor ratio with 2% dye on was heated to 95C at 1 C/min and held at received. A commercial scouring agent weight of fabric. Two different dyeing that temperature for 15 min. The fabric was used where indicated in the procedures were used with conventional was removed from the bath, rinsed once procedures. cotton (scoured and bleached only) and with 50C water and allowed to air dry. the reactive dyes. In this work, unmodified Cationic Reactant cotton was dyed using the procedures rec- Procedure 3 Application ommended by the dye manufacturers. Fig. Procedure 3, was used with cationic cotA solution consisting of 50 g/L 3-chloro2 shows generalized representations of the ton and all four reactive dye types. A 2-hydroxypropyltrimethylammonium reactive groups investigated. The two bi- room temperature bath (~22C) in a dyechloride (65% solution) and 36 g/L of functional dye chemistries studied have ing can was adjusted to pH 9 with so50% sodium hydroxide was pad applied two reactive groups per dye molecule. The dium carbonate. The dye and prewetted to the well-prepared bleached cotton knit dyeing procedure for cationic cotton was fabric were added and the can was fabric at 100% wet pickup. The 2,3chosen to not only allow dyeing without sealed. Immediately, the dyebath was epoxypropyltrimethylammonium chloride electrolytes, but also without the usual heated to 100C at 1 C/min and held at reactant is formed in situ in the pad bath. high level of alkalinity associated with fiber that temperature for 45 mm. The bath To minimize hydrolysis of the epoxy reacreactive dyes.^ was cooled to 60C, the pH adjusted to 5tant, the sodium hydroxide was added to 6 with acetic acid, and the bath held at the bath just prior to application. The Procedure 1 60C for 5 min. The fabric was removed padded fabric was wrapped in plastic to Procedure 1 was used with the from the bath, rinsed once with 50C prevent chemical migration due to evapochlorodifluoropyrimidine, monofluoro- water and allowed to air dry. ration of water and to exclude carbon triazine, and bifunctional vinyl sulfone/ dioxide from the padded fabric. The pyrimidine dyes for conwrapped fabric was stored at room temventional cotton. The ap- TABLE II. perature (~22C) for 24 hr, then rinsed propriate amounts of alseveral times with water and finally with kali, salt, and dye (Table II) Alkali and Salt Concentrations for Conventional Cotton a dilute (1-2 g/L) acetic acid solution. The were added to a room Dyeings with Reactive Dyes final fabric pH (AATCC Test Method 81) Sodium Sodium temperature bath (~22C) was 7.4.^ The amount of nitrogen in the Carbonate Chloride in a dyeing can. Fabric, Reactive treated fabric attributed to the cationic Functionality Concentration Concentration prewetted with water, reagent was 0.15%, which corresponds 20 g/L 50 g/L was added to the can,and chlorodifluoropyrimidine to a cellulose fiber with 1.7 mole % catmonofluorotriazine 8 g/L 40 g/L the can was sealed. Immebifunctional vinyl ionic substitution; i.e., there are 1.7 catdiately, the bath was sulfone/pyrimidine 8 g/L 40 g/L ionic dye sites in every 100 cellulose reheated to 60C at 1 C/min bifunctional-bisnicotinotriazine 40 g/L (sodium sulfate) leat units. V ao02 in
,©
-OH
+
CH2CHCH2N-CH3 ^O^ CH3
Fiber reactive dyes with four different reactive groups were used to dye both unmodified cotton and cotton cationized with 2,3epoxypropyltrimethylammonium chloride. Supplier recommended dyeing procedures were used with unmodified cotton, while a non-salt, non-afterscour procedure was used with the cationic cotton dyeings. Color yields and colorfastness (washfastness, crockfastness, and lightfastness) properties were determined. Dyeings with cationic cotton showed equivalent fastness with generally higher color yields. The implications and challenges of using cationized cotton are discussed.
Hale Waihona Puke Baidu
Dyeing Cationic Cotton with Fiber Reactive Dyes: Effect of Reactive Chemistries
By Peter J. Hauser and Adham H. Tabba, North Carolina State University, Raleigh Dyeing cotton with fiber reactive dyes is for water solubility, the electrostatic intercurrently a high energy consuming, water action between a positively charged fiber intensive, pollution generating process. and negatively charged dye molecules Since cotton has only a moderate affinity can substantially increase the affinity of for most fiber reactive dyes, high concen- dyes for the fiber and reduce the need for trations of electrolytes and extended dye- dyebath electrolytes. Numerous studies ing cycles at high temperatures are needed have reported a variety of chemicals that to achieve reasonable dye exhaustion. Al- can impart a cationic charge to cotton though significant improvements in dye- fibers.^"" Of particular interest is 2,3fiber affinities have been realized with new epoxypropyltrimethylammonium chlodye molecules, dyebath electrolytes are still ride, a product that has been shown to needed. Since the reactive groups in fiber be able to provide a cotton fabric with reactive dyes can react with water as well greatly enhanced affinity for anionic dyes as with the cotton fiber, this unavoidable with resulting reduced environmental hydrolysis leaves unfixed dye molecules impact, lower energy consumption, and that must be removed by multiple rinses increased dyehouse productivity (Fig. and after-washing in order to meet washfastness requirements. As a result, the This work looks at dyeing cotton typical cotton dyehouse discharges high modified with 2,3-epoxypropyltnmethylvolumes of wastewater containing signifi- ammonium chloride with commercially cant amounts of dyes and chemicals. available fiber reactive dyes having a vaModifying cotton fibers with cationic riety of reactive groups to determine how charges prior to dyeing is an attractive the structure of the reactive groups afroute to improving dye-fiber affinity. Since fiber reactive dyes contain anionic groups CH3
1
Key Terms Cationic Cotton Dyeing Reactive Dyes
AATCC REVIEW Bifunctional-bisnicotinotriazine
Bifunctional - vinyl sulfone/pyrimidine
36
peerreviewed
Cl. F chlorodifluoropyrimidine monofluorotriazine
ABSTRACT
fects color yields and colorfastness of the dyed fabric.
EXPERIMENTAL
Materials
The fabric used for all the dyeings was a 100% cotton single jersey knit that had been scoured and bleached before cationization or dyeing. The use of absorbent fabric eliminated the need for wetting agents in the pretreatment or dyebaths. 3-chloro-2-hydroxypropyltri methylammonium chloride is commercially available as a 65% solution in water and was used as received. The dyes in this study (Table I) were all obtained from commercial sources and were used as received. These dyes were chosen because of their commercial availability and known reactive groups. Vinyl sulfone dyes, a major reactive dye chemistry, were evaluated in CH3 -OCH2CHCH2N-CH3 OH CH3
-D-UV/ -^ N ^
S-CH2CH2OSO3 nicotinotriazine O
vinylsulfone
and held at that temperature for 45 mm. The fabric was then removed from the bath and rinsed once with 50C water, once with a 1-g/L acetic acid solution at 50C, and once again with 50C water. A 1 -g/L scouring agent solution was added to a dyeing can with the dyed fabric, heated to 90C at 3C/min, and held at that temperature for 10 min. The fabric was removed from the scouring bath and rinsed with 60C water until a clear rinse achieved. The fabric was allowed to air dry. Procedure 2
Fig. 1. Reaction of 2,3-epoxypropyltrimethylammonium chloride with cellulose.
TABLE 1.
Dyes Used in this Study Reactive Functionality Chlorodifluoropyrimidine Monofluorotriazine Colour Index Number Reactive Red 147 Reactive Blue 209 Reactive Orange 91 Reactive Red 184 Reactive Blue 182 Reactive Yellow 162 Reactive Red 221 Reactive Blue 217 not available
-D-|— Fig. 2. Reactive groups for fiber reactive dyes.
dye molecule
Procedure 2 was used with the bifunctional-bisnicotinotriazine dyes for conventional cotton. The appropriate amounts of salt and dye (Table II) were added to a room temperature bath earlier work.'' Commercially available so- Dyeing Procedures (~22C) in a dyeing can. Fabric, wetted dium hydroxide (50% solution), acetic All of the dyeings were done in a Mathis with water, was added to the can, and acid (97%), sodium carbonate, sodium Labomat laboratory dyeing machine at a the can was sealed. Immediately, the bath sulfate, and sodium chloride were used as 13.3:1 liquor ratio with 2% dye on was heated to 95C at 1 C/min and held at received. A commercial scouring agent weight of fabric. Two different dyeing that temperature for 15 min. The fabric was used where indicated in the procedures were used with conventional was removed from the bath, rinsed once procedures. cotton (scoured and bleached only) and with 50C water and allowed to air dry. the reactive dyes. In this work, unmodified Cationic Reactant cotton was dyed using the procedures rec- Procedure 3 Application ommended by the dye manufacturers. Fig. Procedure 3, was used with cationic cotA solution consisting of 50 g/L 3-chloro2 shows generalized representations of the ton and all four reactive dye types. A 2-hydroxypropyltrimethylammonium reactive groups investigated. The two bi- room temperature bath (~22C) in a dyechloride (65% solution) and 36 g/L of functional dye chemistries studied have ing can was adjusted to pH 9 with so50% sodium hydroxide was pad applied two reactive groups per dye molecule. The dium carbonate. The dye and prewetted to the well-prepared bleached cotton knit dyeing procedure for cationic cotton was fabric were added and the can was fabric at 100% wet pickup. The 2,3chosen to not only allow dyeing without sealed. Immediately, the dyebath was epoxypropyltrimethylammonium chloride electrolytes, but also without the usual heated to 100C at 1 C/min and held at reactant is formed in situ in the pad bath. high level of alkalinity associated with fiber that temperature for 45 mm. The bath To minimize hydrolysis of the epoxy reacreactive dyes.^ was cooled to 60C, the pH adjusted to 5tant, the sodium hydroxide was added to 6 with acetic acid, and the bath held at the bath just prior to application. The Procedure 1 60C for 5 min. The fabric was removed padded fabric was wrapped in plastic to Procedure 1 was used with the from the bath, rinsed once with 50C prevent chemical migration due to evapochlorodifluoropyrimidine, monofluoro- water and allowed to air dry. ration of water and to exclude carbon triazine, and bifunctional vinyl sulfone/ dioxide from the padded fabric. The pyrimidine dyes for conwrapped fabric was stored at room temventional cotton. The ap- TABLE II. perature (~22C) for 24 hr, then rinsed propriate amounts of alseveral times with water and finally with kali, salt, and dye (Table II) Alkali and Salt Concentrations for Conventional Cotton a dilute (1-2 g/L) acetic acid solution. The were added to a room Dyeings with Reactive Dyes final fabric pH (AATCC Test Method 81) Sodium Sodium temperature bath (~22C) was 7.4.^ The amount of nitrogen in the Carbonate Chloride in a dyeing can. Fabric, Reactive treated fabric attributed to the cationic Functionality Concentration Concentration prewetted with water, reagent was 0.15%, which corresponds 20 g/L 50 g/L was added to the can,and chlorodifluoropyrimidine to a cellulose fiber with 1.7 mole % catmonofluorotriazine 8 g/L 40 g/L the can was sealed. Immebifunctional vinyl ionic substitution; i.e., there are 1.7 catdiately, the bath was sulfone/pyrimidine 8 g/L 40 g/L ionic dye sites in every 100 cellulose reheated to 60C at 1 C/min bifunctional-bisnicotinotriazine 40 g/L (sodium sulfate) leat units. V ao02 in
,©
-OH
+
CH2CHCH2N-CH3 ^O^ CH3
Fiber reactive dyes with four different reactive groups were used to dye both unmodified cotton and cotton cationized with 2,3epoxypropyltrimethylammonium chloride. Supplier recommended dyeing procedures were used with unmodified cotton, while a non-salt, non-afterscour procedure was used with the cationic cotton dyeings. Color yields and colorfastness (washfastness, crockfastness, and lightfastness) properties were determined. Dyeings with cationic cotton showed equivalent fastness with generally higher color yields. The implications and challenges of using cationized cotton are discussed.