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Syntheses and Application of Sulfonic Acid Dyes on Wool Fabric.

Byline: Zeeshan Akhtar, Muhammad Farooq, Mohib Raza Kazimi, Rasheeda Parveen, Syed Ishrat Ali, Aneela Karim and Khalid Mohammed Khan

Summary: Syntheses of acid dyes were done by reacting diazotized substituted aryl amines and substituted naphthalene sulfonic acids as coupling component. Structure elucidation of these synthetic dyes was carried out by their UV-visible, IR, 1HNMR spectra, elemental analysis and negative MALDI-TOF mass spectrometric analysis. The aim of this research is the application of synthesized acid dyes on wool fabric and fastness properties by light, washing, perspiration, crocking data from color spectrophotometer studied.

Keywords: Acid dyes, Data color spectrophotometer, Maldi-TOF mass spectra-negative ion mode.

Introduction

Acid dyes are very large class of dyes and comprises various categories. Most important are sulfonic acid derivatives of azoic dyes. The practical uses of these dyes are characterized by their capacity to dye protein and polyamide fibers. Under certain condition they may be used for dyeing polyacrylonitrile fibers. Similar to direct dyes, they are anionic dyes with general formula RSO3Na but they do not dye or poor dye cellulosic fiber without consuming color fastness. Acid dyes are water soluble anionic dyes, bright in colors and have good washing fastness properties. Acid dyes contain a chromophoric group and an acidic group usually - SO3H in the form of sodium salt, that are soluble in water.

Wool, silk, nylon and protein based natural fibers also have amino group that can bond with acid dyes, the bond formed between the dye and fiber are salt linkages.

FIBER-NH2-HSO3-DYE (Fiber with basic amino group) (Dye with sicidic sulfonic group) - FIBER-NH3.SO3-DYE (Dyed fiber with salt linkage between dye and fiber)

The term acid dyes derive from the dyeing process which is carried out in aqueous acid solution (pH: 2-6). Protein fibers contain amino and carboxyl groups which are ionized mostly to NH3 + and COO-.

In the acid dye bath the carboxyl ions are converted to un-dissociated carboxyl group owing to addition of acid HX (Sulfuric or formic acid) which causes the positively charged wool (H3N-W-COOH) to take up an equivalent amount of acid anions X-, hydrogen sulfate, as depicted in Scheme-1.

(Equations)

The actual dyeing process consists of a replacement of absorbed acid anions X- by the added dye anions (F), since the later exhibit a much greater affinity for the substrate than much smaller acid anions. Thus the dye is bonded to the wool by electrostatic attraction (salt formation) but affinity for the fibers.

Experimental

Material and Analysis

All reagent and solvents were of technical grade. Thin layer chromatography (TLC) was taken on silica gel PF 254 (Merck) plates. UV-visible spectra were taken on a spectromiczo Baush and Lomb in de-ionized water. IR spectra were recorded on a Jasco A-30 spectrometer in KBr disc. 1HNMR spectra were determined on a Bruker AM 300 spectrophotometer in DMSO. Dyeing was carried out on a I.R. dyeing machine of Roaches Int. Touch screen control system. Color fastness properties were studied by using SDC test methods and CIE color coordinates L*, a*, b* were recorded on data color spectroflash-650.

Synthesis of Compounds

Substituted aryl amine (A) 10 m.mol was taken in 2-5 ml of conc. hydrochloric acid. The solution is cooled in ice bath at 0-5 C and sodium nitrite 10 mmol in 20 ml water was added drop wise with constant stirring to the amine hydrochloride. Test of nitrous acid was carried out by starch iodide paper. Excess of sodium nitrite was eliminated by sulfamic acid coupling component (B) as marked in Fig. 1. Amino hydroxyl-naphthalene sulfonic acids 10 mmol in 300 ml water was added to the solution and pH 5-6 was adjusted by addition of 10% sodium carbonate aqueous solution (Table-1).

To this solution, diazotized solution of aryl amines (A) was added drop wise at 0-5 C with pH monitor at constant stirring. pH was maintained at 7-8 by 10% aqueous Na2CO3 solution at temperature 0-5 C.

Reaction completion was checked by b-naphthol solution spot test on filter paper. The aqueous dye solution was stirred for 3-4 h. TLC was checked using (MeOH:Hexane:H20,9:1:1). The dye was separated by salting out with 10% sodium chloride solution. The dye was filtered and dried under vacuum at 60 C and purified by dimethyl formamide. General procedure of synthesis is shown in Fig. 1.

i. Synthesis of 1-Amino-8-naphthol-7-(2-methoxyanilinodiazinyl-5-sulfonic)-3,6-disulfonic acid (C1).

(Equations)

MALDI-ToF (negative) analysis: Mol. Formula C17H15N3O11S3, Mol. Weight: 533.513, MALDI spectra: 533.091, Species Observed: M-H. UV: max: 560 nm; log = 4.5. IR: IR (Jasco/cm-1): max 3449 (NH-Stretch), 1587 (N=N), 1207 (S=O), 1046 (S-O). 1HNMR (300 MHz, DMSO-d6): 3.98 (s, 2H), 6.8 (s, 2H, NH), 7.02-7.06 (m, 2H), 7.27 (s, 1H), 7.40 (dd, J = 2.1, 2.4 Hz, 1H), 7.88 (s, 1H), 8.12 (s, J = 2.1, 1H), 15.79 (br s, OH).

(Equations)

Table-1: Diazo and Coupling Components

###Dyes Code###A###A Diazo Component###B###B Coupling Component

###C1###A1###2-Methoxyaniline-5-sulfonic acid###B1###1-Amino-8-naphthol-3,6-disulfonic acid (H-acid)

###C2###A2###4- Amino-acetophenone###B2###1-Amino-8-naphthol-3,6-disulfonic(H-acid)

###C3###A3###3- Amino-acetophenone###B3###1-Amino-8-naphthol-3-,6-disulfonic acid (H-acid)

###C4###A4###3- Amino sulfonic acid###B4###1-Amino-8-naphthol-3,6-disulfonic acid (H-acid)

###C5###A5###4-Amino sulfonic acid###B5###1-Amino-8-naphthol-3,6-disulfonic acid (H-acid)

###C6###A6###4-Amino sulfonic acid###B6###1-N-Aminoacetye-8-naphthol-3,6-disulfonic acid (H-acid)

###C7###A7###3-Amino sulfonic acid###B7###1-N-Aminoacetye-8-naphthol-3,6-disulfonic acid (1-N-aminoacetyl-H-acid)

###C8###A8###4-Amino-acetophenone###B8###1-N-Aminoacetye-8-naphthol-3,6-disulfonic acid (1-N-aminoacetyl-H-acid)

###C9###A9###3-Amino-acetophenone###B9###1-N-Aminoacetye-8-naphthol-3,6-disulfuric acid

###(1-N-aminoacetyl-H-acid)

ii. Synthesis of 1-Amino-8-naphthol-7-(4-aminoacetophenyldiazinyl)-3,6-disulfonic acid (C2)

(Equations)

MALDI-ToF (negative) analysis: Mol. Formula C18H15N3O8S2, Mol. Weight: 465.459, MALDI spectra: 464.339, Species Observed: M-H-H2O. UV: max: 540nm log = 4.1. IR: max 3421 (NH-Stretch), 1596 (N=N), 1213 (S=O), 1046 (S-O). 1HNMR (300 MHz, DMSO-d6): 2.55 (s, 3H), 6.82 (s, NH, 2H), 7.27(s, NH, 2H), 7.27 (s, 1H) , 7.63 (s, J = 8.7 Hz, 2H) , 7.72 (d, J = 8.7 Hz, 2H) , 7.95 (d, J = 8.7 Hz, 2H) , 15.19 (s, OH, 1H).

iii. Synthesis of 1-Amino-8-naphthol-7-(3-aminoacetophenyldiazinyl)-3,6-disulfonic acid (C3)

(Equations)

MALDI-ToF (negative) analysis: Mol. Formula C18H15N3O8S2, Mol. Weight: 465.459, MALDI spectra: 464.473, Species Observed: M-H. UV: max: 530 nm, log = 4.1. IR: (Jasco/cm-1): max 3426 (NH-Stretch), 1579 (N=N), 1214 (S=O), 1047 (S-O). 1HNMR (300 MHz, DMSO-d6): 2.63 (s, 3H), 6.82 (s, NH, 2H), 7.24 (s, 1H), 7.53 (s, J = 7.8 Hz, 1H), 7.66 (s, J = 7.2 Hz, 1H), 7.99 (s, J = 7.5 Hz, 1H), 8.23 (s, 1H), 15.22 (br s, OH).

Synthesis of 1-Amino-8-naphthol-7-(3-aminosulfophenyldiazinyl)-3,6-disulfonic acid (C4)

(Equations)

MALDI-ToF (negative) analysis, Mol. Formula C16H13N3O10S3, Mol. Weight: 503.487, MALDI spectra: 502.120, Species Observed: M-H. UV: max: 560nm, log = 4.2. IR: max 3421 (NH-Stretch), 1575 (N=N), 1213 (S=O), 1036 (S-O). HNMR (300 MHz, DMSO-d6): 6.83 (s, NH, 2H), 7.03 (2H,d, J = 8.4 Hz), 7.35 (s, 1H), 7.56-7.71 (m, 2H) , 7.97 (d, J = 8.4 Hz, 2H), 15.47 (br s, OH).

3.2.5 Synthesis of 1-Amino-8-naphthol-7-(4-aminosulfophenyldiazinyl)-3,6-disulfonic acid (C5)

(Equations)

MALDI-ToF (negative) analysis: Mol. Formula C16H13N3O10S3, Mol. Weight: 503.487, MALDI spectra: 502.126, Species Observed: M-H. UV: max: 570 nm, log = 4.5. IR: max 3433 (NH-Stretch), 1586 (N=N), 1196 (S=O), 1046 (S-O). HNMR (300 MHz, DMSO-d6): 7.98 (d, J = 8.1 Hz, 1H), 7.70 (t, J = 3 Hz, 1H), 7.63 (d, J = 8.4 Hz, 1H), 7.56 (s, 1H), 7.43 (d, J = 8.7 Hz, 1H), 7.24 (d, J = 8.7 Hz, 1H), 6.43 (d, J = 8.4 Hz, 1H).

Synthesis of 1-Aminoacetyl-8-naphthol-7-(4-aminosulfophenyl-diazinyl)-3,6-disulfonic acid (C6)

(Equations)

MALDI-ToF (negative) analysis: Mol. Formula C18H15N3O11S3, Mol. Weight: 545.523, MALDI spectra: 544.095, Species Observed: M-H. UV: max: 560nm, log = 4.4. IR: max 3452 (NH-Stretch), 1569 (N=N), 1213 (S=O), 1039 (S-O). 1HNMR (300 MHz, DMSO-d6): 2.21 (s, 3H), 6.43 (s, NH, 1H), 7.32-7.42 (m, 2H), 7.58 (d, J = 8.7 Hz, 2H), 7.85 (d, J = 8.7 Hz, 2H).

Synthesis of 1-Aminoacetyl-8-naphthol-7-(3-aminosulphonyldiazinyl)-3,6-disulfonic acid (C7)

(Equations)

MALDI-ToF (negative) analysis: Mol. Formula C18H15N3O11S3, Mol. Weight: 545.523, MALDI spectra: 544.092, Species Observed: M-H. UV: max: 530nm, log = 3.99. IR: max 3454 (NH-Stretch), 1558 (N=N), 1212 (S=O), 1047 (S-O). 1HNMR (300 MHz, DMSO-d6): 2.57 (s, 3H) , 7.14 (d, J = 6.9 Hz, 1H), 7.35 (s, 1H), 7.43-7.43 (m, 2H), 7.98 (s, 1H), 16.36 (br s, OH).

Synthesis of 1-Aminoacetyl-8-naphthol-7-(4-aminoacetophenyl-diazinyl)-3,6-disulfonic acid (C8)

(Equations)

MALDI-ToF (negative) analysis: Mol. Formula C20H17N3O9S2, Mol. Weight: 507.496, MALDI spectra: 506.266, Species Observed: M-H. UV: max: 531nm, log = 4.2. IR: max 3449 (NH-Stretch), 1559 (N=N), 1211(S=O), 1048 (S-O). HNMR (300 MHz, DMSO-d6): 1.7 (s, 2H), 2.57 (s. 3H), 7.37 (s, 1H), 7.94-7.99 (m, 2H).

Synthesis of 1-Aminoacetyl-8-naphthol-7-(3-aminoacetophenyl-diazinyl)-3,6-disulfonic acid (C9)

(Equations)

MALDI-ToF (negative) analysis: Mol. Formula C20H17N3O9S2, Mol. Weight: 507.496, MALDI spectra: 506.428, Species Observed: M-H. UV: max: 523nm, log = 4.3. IR: max 451 (NH-Stretch), 1558 (N=N), 1214 (S=O), 1049 (S-O). HNMR (300 MHz, DMSO-d6): 1.77 (s, 3H), 2.63 (s, 3H), 7.36 (s, 1H), 7.45 (s, 1H), 7.56 (s, 1H), 7.75 (d, J = 7.5Hz, 1H), 7.56 (d, J = 7.5 Hz), 8.19 (d, J = 8.1 Hz).

Application and Evaluation of Acid Dyes on Wool Fabric

Dyeing Method

Scoured and bleached wool fabric was dyed with 1% of synthesized dyes on the weight of fabric (o.w.f.). The liquor to fabric ratio was maintained at 1:20 during dyeing. pH of bath was maintained at 2.5 to 3.5. The temperature of dye bath was raised to 60 C at the rate of 2 C/min for 30 min. Then Glauber's salt was added to the dye bath and process continued further for 30 min. Then dye bath was dropped and fabric rinsed thoroughly with cold water. Fabric was washed with nonionic detergent at 50 C. The dyed fabric was air dried at room temperature.

Results and Discussion

Nine derivatives of acid dyes were synthesized and characterized by different spectroscopic techniques. Substituted aryl amines were used as diazo component and amino-hydroxy substituted naphthalene sulfonic acid were used as coupling component. Synthesized dyes were purified and structures were confirmed by UV-visible, I.R, 1H-NMR, Maldi-TOF spectra in negative ion mode for mass studies. These dyes are applied to wool fabric by exhaust dyeing process. Fastness properties of pre- and post-washing of the dyed fabric are measured by Datacolor SF600 spectrophotometer. The results L*, a*, b* are reported in Table 2-4 as the washing, light, and perspiration tests.

Further washing, light, crocking fastness evaluation of wool dyed fabric on multi-fiber is reported in Table-5. The fastness properties and dye fixation on the wool fabric is reported in Table-6. Overall results of the fastness properties are good while dye fixation C1-C8 was found 80-94%.

Table-2: Spectrophotometric Values of Washing Fastness on Wool dyed fabric in D65. 10 Deg. Observer.

###Sample Name###L*###a*###b*###C*###h*###X###Y###Z###x###y

###C-1 Before Wash###22.45###23.31###-6.23###24.13###345.03###5.12###3.64###5.12###0.3691###0.2623

###C-1 After Wash###21.76###22.20###-5.38###23.15###344.05###5.06###3.13###5.00###0.3836###0.2373

###C-2 Before Wash###18.31###9.98###-7.89###12.72###321.67###2.98###2.59###4.04###0.3104###0.2692

###C-2 After Wash###17.17###8.08###-6.37###11.49###320.40###2.15###2.35###3.95###0.2544###0.2781

###C-3 Before Wash###17.12###10.00###-5.57###11.45###330.89###2.70###2.33###3.30###0.3245###0.2793

###C-3 After Wash###16.55###9.51###-4.65###10.11###329.45###2.17###2.05###3.15###0.2944###0.2781

###C-4 Before Wash###17.67###6.34###-8.70###10.77###306.06###2.63###2.44###3.99###0.2906###0.2696

###C-4 After Wash###16.81###5.45###-7.28###9.56###305.33###2.18###2.28###3.57###0.2714###0.2839

###C-5 Before Wash###17.08###7.13###-8.01###10.73###311.69###2.55###2.32###3.69###0.2975###0.2711

###C-5 After Wash###16.66###6.59###-7.56###9.28###310.10###2.00###2.13###3.11###0.2762###0.2941

###C-6 Before Wash###32.67###52.66###8.68###53.37###9.36###13.71###7.39###5.71###0.5114###0.2755

###C-6 After Wash###31.13###51.50###7.28###52.04###8.16###12.22###6.01###4.91###0.5280###0.2597

###C-7 Before Wash###35.01###50.33###5.91###50.68###6.69###14.96###8.50###7.41###0.4847###0.2754

###C-7 After Wash###34.37###50.15###4.28###49.44###5.19###13.46###7.71###6.22###0.4914###0.2814

###C-8 Before Wash###30.69###47.28###14.03###49.32###16.53###11.64###6.52###3.94###0.5268###0.2950

###C-8 After Wash###29.15###46.19###13.55###48.11###15.45###10.28###5.55###3.35###0.5359###0.2893

###C-9 Before Wash###40.65###51.74###16.40###54.28###17.59###19.65###11.65###7.20###0.5105###0.3025

###C-9 After Wash###39.31###50.68###15.75###53.15###16.45###18.65###10.11###6.22###0.5331###0.2890

Table-3: Spectrophotometric Values of Light Fastness on Wool dyed fabric in D65.10 Deg.Observer.

###Sample Name###L*###a*###b*###C*###h*###X###Y###Z###x###y

###C-1 Untreated###22.45###23.31###-6.23###24.13###345.03###5.12###3.64###5.12###0.3691###0.2623

###C-1 Treated###22.22###22.13###-5.66###23.33###343.05###5.22###3.27###5.00###0.3869###0.2424

###C-2 Untreated###18.31###9.98###-7.89###12.72###321.67###2.98###2.59###4.04###0.3104###0.2692

###C-2 Treated###17.60###8.16###-6.51###11.12###320.51###2.15###2.07###3.81###0.2677###0.2577

###C-3 Untreated###17.12###10.00###-5.57###11.45###330.89###2.70###2.33###3.30###0.3245###0.2793

###C-3 Treated###16.37###9.81###-4.98###10.18###329.16###2.18###2.00###3.31###0.2910###0.4419

###C-4 Untreated###17.67###6.34###-8.70###10.77###306.06###2.63###2.44###3.99###0.2906###0.2696

###C-4 Treated###16.15###6.06###-7.91###9.13###305.15###2.50###2.27###3.14###0.3160###0.2869

###C-5 Untreated###17.08###7.13###-8.01###10.73###311.69###2.55###2.32###3.69###0.2975###0.2711

###C-5 Treated###16.25###6.06###-7.99###9.46###310.15###2.46###2.15###2.96###0.3249###0.2840

###C-6 Untreated###32.67###52.66###8.68###53.37###9.36###13.71###7.39###5.71###0.5114###0.2755

###C-6 Treated###31.46###51.50###7.48###52.55###8.18###12.66###6.41###4.85###0.5292###0.2679

###C-7 Untreated###35.01###50.33###5.91###50.68###6.69###14.96###8.50###7.41###0.4847###0.2754

###C-7 Treated###34.40###49.21###4.70###49.56###5.15###13.12###7.40###7.14###0.4743###0.2675

###C-8 Untreated###30.69###47.28###14.03###49.32###16.53###11.64###6.52###3.94###0.5268###0.2950

###C-8 Treated###29.82###46.96###13.23###48.30###15.46###10.35###5.46###3.25###0.5430###0.2864

###C-9 Untreated###40.65###51.74###16.40###54.28###17.59###19.65###11.65###7.20###0.5105###0.3025

###C-9 Treated###40.47###50.56###15.80###53.61###16.56###18.95###10.11###6.98###0.5258###0.2805

Table-4: Spectrophotometric Values of Perspiration (Alkaline) on Wool dyed fabric in D65.10 Deg. Observer

Sample Name###L*###a*###b*###C*###h*###X###Y###Z###x###y

C-1 Untreated###22.45###23.31###-6.23###24.13###345.03###5.12###3.64###5.12###0.3691###0.2623

C-1 Treated Alkaline###21.66###22.18###-5.79###23.59###344.71###5.05###3.30###4.65###0.3884###0.2538

C-2 Untreated###18.31###9.98###-7.89###12.72###321.67###2.98###2.59###4.04###0.3104###0.2692

C-2 Treated Alkaline###17.07###9.46###-6.81###11.48###320.17###2.21###2.16###4.00###0.2640###0.2580

C-3 Untreated###17.12###10.00###-5.57###11.45###330.89###2.70###2.33###3.30###0.3245###0.2793

C-3 Treated Alkaline###16.55###9.15###-4.18###10.61###330.28###2.27###2.11###3.12###0.3026###0.2813

C-4 Untreated###17.67###6.34###-8.70###10.77###306.06###2.63###2.44###3.99###0.2906###0.2696

C-4 Treated Alkaline###16.48###5.39###-7.15###9.85###305.11###2.19###2.23###3.19###0.2877###0.2930

C-5 Untreated###17.08###7.13###-8.01###10.73###311.69###2.55###2.32###3.69###0.2975###0.2711

C-5 Treated Alkaline###16.16###6.16###-7.87###9.62###310.15###2.05###2.11###3.32###0.2740###0.2820

C-6 Untreated###32.67###52.66###8.68###53.37###9.36###13.71###7.39###5.71###0.5114###0.2755

C-6 Treated Alkaline###31.78###51.54###7.24###52.21###8.30###12.69###6.10###4.70###0.5402###0.2596

C-7 Untreated###35.01###50.33###5.91###50.68###6.69###14.96###8.50###7.41###0.4847###0.2754

C-7 Treated Alkaline###34.15###49.71###4.68###49.16###5.15###13.46###7.21###6.44###0.4064###0.2659

C-8 Untreated###30.69###47.28###14.03###49.32###16.53###11.64###6.52###3.94###0.5268###0.2950

C-8 Treated Alkaline###29.14###46.44###13.12###48.18###15.11###10.25###5.15###3.13###0.5531###0.2779

C-9 Untreated###40.65###51.74###16.40###54.28###17.59###19.65###11.65###7.20###0.5105###0.3025

C-9 Treated Alkaline###39.22###50.16###15.50###53.21###16.44###18.20###10.56###6.55###0.5154###0.2990

Table-5: Washing, Crocking and Light Fastness Evaluations on Wool dyed fabric on multi-fiber.

Dye Code###Change in Shade###CA###CO###PA###PES###PAC###WO###Crocking###Light Fastness

###Dry###Wet

C-1###4-5###4-5###4-5###5.0###4-5###4-5###4.0###5.0###5.0###4-5

C-2###4.0###4-5###3.0###3-4###4-5###4-5###4.0###4-5###4-5###5.0

C-3###4.0###4.0###3-4###4.0###4-5###3-4###5.0###4-5###4-5###4-5

C-4###4-5###5.0###4-5###5.0###5.0###5.0###5.0###5.0###4-5###4-5

C-5###4-5###5.0###4-5###5.0###5.0###5.0###5.0###5.0###4-5###5.0

C-6###4.0###5.0###4.0###4.0###5.0###5.0###4-5###5.0###4-5###4-5

C-7###4.0###5.0###3-4###4.0###5.0###4-5###4.0###4-5###4-5###4-5

C-8###4.0###5.0###4.0###4-5###4-5###5.0###4-5###5.0###4-5###4-5

C-9###4-5###5.0###4-5###4-5###5.0###5.0###4-5###5.0###4-5###4-5

Table-6: Results of Various Fastness Properties of Dyes on Wool Fabric.

###Fastness To

###Dye Code###Light hours###Wash###Perspiration alkaline###Rubbing###% Dye fixation by K/S values

###100###y###s###y###s###dry###wet

###C-1###4-5###4-5###4-5###4-5###4-5###5.0###5.0###94.64

###C-2###5.0###4.0###3.0###4-5###4-5###4-5###4-5###92.62

###C-3###4-5###4.0###3-4###4-5###4-5###4-5###4-5###91.40

###C-4###4-5###4-5###4-5###4-5###4-5###5.0###4-5###88.09

###C-5###5.0###4-5###4-5###4-5###4-5###5.0###4-5###87.80

###C-6###4-5###4.0###4.0###4-5###4-5###5.0###4-5###88.59

###C-7###4-5###4.0###3-4###4.0###3-4###4-5###4-5###80.39

###C-8###4-5###4.0###4.0###4.0###4.0###5.0###4-5###87.59

###C-9###4-5###4-5###4-5###4-5###4-5###5.0###4-5###88.88

Conclusion

The synthesized acid dyes are intense in color and red in shade while applied on wool fabric having good washing, light, rubbing and perspiration. Dyes fixation as calculated from k/s data color spectrophotometer are 80-90%.

References

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3. A. Fritz, J. Cant, Consumer Texitles, Oxford University Press, South Melbourne, p.1 (1988).

4. B.P Corbman, Textiles Fiber to Fabric, McGraw-Hill, Singaporep, p. 3 (1983).

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6. H. Voglar, and U. Wettstreit. Wettstreit um die Polyamidfasern, Polymidfasern. Chemie in unserer, Zeit, 47, 62 (2013).

7. A.K.R. Chaudry, Textile Preparation and dyeing, Science Publishers, USA, p. 134 (2006).

8. K. Hunger, Industrial dyes: chemistry, Properties, Application, John Wiley and Sons, Darmsdart, p. 479 (2003).

9. Color fastness to washing, Standard Methods for determination of the color fastness of textile and leather, The Society of Dyers and Colorist fifth edition, 1990, PP. CO4/1.

10. Color fastness to sublimation, Standard Methods for the determination of the color fastness of textile and leather, The Society of Dyers and Colorist fifth edition, 1990, PP. PO1/1.

11. Color fastness to rubbing, Standard Methods for determination of the color fastness of textile of leather, The Society of Dyers and Colorist fifth edition, 1990, PP.X12/1.

12. Color fastness to perspiration, Standard Methods for the determination of the color fastness of textiles and anther, The Society of Dyers and Colorists, fifth edition, 1990, PP EO4/1.

13. ISO 105 - CO6: 2010 - Textiles - Tests for colour fastness - Part CO6: Colour fastness to domestic and commercial laundering.

14. ISO 105 - BO2: 2013 - Textiles - Test for colour fastness - Part BO2: Colour fastness to artificial light: Xenon arc fading lamp test.

15. ISO 105 - EO3: 2010 - Textiles - Test for colour fastness - Part EO3: Colour fastness to chlorinated water.

16. Color Fastness to Perspiration ISO 105 EO4.
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Author:Akhtar, Zeeshan; Farooq, Muhammad; Kazimi, Mohib Raza; Parveen, Rasheeda; Ali, Syed Ishrat; Karim, A
Publication:Journal of the Chemical Society of Pakistan
Article Type:Report
Date:Feb 29, 2016
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