Plasma Induced Graft Polymerization of Cationic and Fluorocarbon

Subscriber access provided by - Access paid by the | UCSB Libraries

Article

Plasma Induced Graft Polymerization of Cationic and Fluorocarbon Monomers into Cotton: Enhanced Dyeability and Photostability Amsarani Ramamoorthy, Hany M. Helmy, Rajeev Rajbhandari, Peter J. Hauser, and Ahmed El-Shafei Ind. Eng. Chem. Res., Just Accepted Manuscript • DOI: 10.1021/acs.iecr.6b01069 • Publication Date (Web): 20 Jun 2016 Downloaded from http://pubs.acs.org on June 25, 2016

Just Accepted “Just Accepted” manuscripts have been peer-reviewed and accepted for publication. They are posted online prior to technical editing, formatting for publication and author proofing. The American Chemical Society provides “Just Accepted” as a free service to the research community to expedite the dissemination of scientific material as soon as possible after acceptance. “Just Accepted” manuscripts appear in full in PDF format accompanied by an HTML abstract. “Just Accepted” manuscripts have been fully peer reviewed, but should not be considered the official version of record. They are accessible to all readers and citable by the Digital Object Identifier (DOI®). “Just Accepted” is an optional service offered to authors. Therefore, the “Just Accepted” Web site may not include all articles that will be published in the journal. After a manuscript is technically edited and formatted, it will be removed from the “Just Accepted” Web site and published as an ASAP article. Note that technical editing may introduce minor changes to the manuscript text and/or graphics which could affect content, and all legal disclaimers and ethical guidelines that apply to the journal pertain. ACS cannot be held responsible for errors or consequences arising from the use of information contained in these “Just Accepted” manuscripts.

Industrial & Engineering Chemistry Research is published by the American Chemical Society. 1155 Sixteenth Street N.W., Washington, DC 20036 Published by American Chemical Society. Copyright © American Chemical Society. However, no copyright claim is made to original U.S. Government works, or works produced by employees of any Commonwealth realm Crown government in the course of their duties.

Page 1 of 26

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60

Industrial & Engineering Chemistry Research

Plasma Induced Graft Polymerization of Cationic and Fluorocarbon Monomers into Cotton: Enhanced Dyeability and Photostability Amsarani Ramamoorthy1, Hany M. Helmy2, Rajeev Rajbhandari1, Peter Hauser1, Ahmed El-Shafei1* 1

North Carolina State University, Fiber and Polymer Science Program, Department of Textile Engineering, Chemistry and Science, , Raleigh, NC 27695 2

National Research Centre, Dokki, Cairo, Egypt

*Corresponding Author: [email protected]

Abstract The objective of this work was to increase color yield of direct dyes on cotton with the aid of grafted quaternary ammonium monomers. Plasma-induced graft polymerization

of

diallyldimethylammonium

chloride

(DADMAC)

and

[2-

(acryloyloxy) ethyl] trimethylammonium chloride (AOETMAC) on cotton followed by dyeing with direct dyes was studied using different concentrations of the monomers and plasma conditions, and the color yield was evaluated using K/S measurements. Colorfastness and staining after laundering were evaluated using the standard grayscale. A significant increase of 149% in color yield was achieved when 30 g/L of DADMAC was used. 100-300% increase in K/S was achieved when ~20g/L of AOETMAC was used. To enhance the wash and lightfastness of the direct dyes on cotton, plasma-induced graft polymerization of 1,1,2,2-tetrahydroperfluorododecyl acrylate was achieved on the dyed cotton and showed considerable enhancement in both the wash and lightfastness.

1 ACS Paragon Plus Environment


1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60

Page 2 of 26

Key Words: Atmospheric pressure plasma grafting, quaternary monomer, cotton, color yield, direct dyes, K/S, lightfastness. 1. Introduction Cationization of Cotton Cationic pre-treatments of cotton using 3-chloro-2-hydroxypropyltrimethyl ammonium chloride (CHPTAC), prior to dyeing, to increase dye affinity and color yield was first reported by Hauser et.al 1. Cationized cotton offers several advantages compared to untreated cotton including 40-50% reduction in dyeing time, reduced effluent toxicity, zero salt, lower temperature, less water, fewer no fixing agents, nearly 100% dye exhaustion, significantly less water for rinsing, little or no cleaning of equipment for faster turnaround and brighter colors manufacturing,

performance

and

environmental

2, 3

. This technology has

advantages;

shown

to

be

biodegradable and practically non-toxic to aquatic organisms 3. Cationization of cotton fabric prior to dyeing with reactive dyes results in excellent washfastness indicating that the cationization reaction took place throughout the cotton fibers, not just on the surface 4. However, CHPTAC in alkaline medium undergoes SN2 to form 2,3-epoxypropyltrimethylammonium chloride (EPTAC), which undergoes hydrolysis in-situ accounting for ~60% loss of the quaternary monomer and great care must be taken in order to minimize hydrolysis. Furthermore, EPTAC presents occupational hazard due to its epoxy nature. Work reported by Hebeish etal. 5 also involved the use of CHPTAC, and it was also reported the reaction yield was low due to hydrolysis. To overcome this 2 ACS Paragon Plus Environment

Page 3 of 26

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


hydrolysis issue, in the present study, we propose different quaternary monomers diallyldimethylammonium chloride (DADMAC) and [2- (acryloyloxy) ethyl] trimethylammonium chloride (AOETMAC) that can be plasma graft polymerized throughout cotton fibers to generate positive charges thereby enabling it to have higher interactions towards negatively charged dyes including acid, direct and reactive dyes resulting higher color yield on the fabrics and enhanced wet fastness properties. DADMAC is manufactured by reaction of allyl chloride with dimethyl amine in a closed system. It was found to improve dyeability of polypropylene and cotton-nylon fabric

6, 7

. Poly-DADMAC was used in textile for dye-fixation, anti-static and

effective against wide range of micro-organisms. It is cheap, environmentally safe and it is the first polymer approved by USFDA for use in potable water treatment 8. And most importantly, it gives high reaction yield, and completely crosslinked network is formed as a result of poly-DADMAC formation. Plasma-induced graft polymerization involves the use of plasma to generate free radicals to initiate a free radical graft polymerization of a monomer to a substrate via covalent bonding

9, 10

. Chemicals that are grafted to a polymer may form either a

monolayer or may subsequently undergo polymerization and form a desired thickness 11

. Plasma has been shown to form free radicals on a substrate’s surface;

subsequently, these radicals are available for reaction with a monomer to form a permanent or durable finish with certain functionalities

12

. Atmospheric pressure

plasma is an alternative to conventional wet chemical grafting 3 ACS Paragon Plus Environment

13, 14

. The plasma


1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60

Page 4 of 26

approach has the advantage of reducing water consumption and reaction time over conventional processes. This technology has been used to generate hydrophilic

15-19

,

hydrophobic 20-23 or oleophobic 24, 25 treatment in the textile field without affecting the bulk properties of a sample at lower processing temperatures 26. Moreover, plasma has been used for other textile applications including biocidal finishes

27, 28

, enhancing

dyeability 29, flame retardancy 30, 31, wrinkle resistance 32, water/fuel separation 33 and antistatic finishes 34. The objectives of this work were two-fold: 1) to increase color yield of direct dyes on cotton with the aid of quaternary ammonium monomers using plasmainduced graft polymerization and 2) to achieve highly durable water and oil repellent fluorocarbon on dyed cotton fabrics to improve wash and light fastness35. 1, 1, 2, 2tetrahydroperfluorododecyl acrylate (THPFDA) fluorocarbon monomer was used to achieve water and oil repellent cotton. The colorfastness to laundering was evaluated following plasma treatment using the AATCC standard Test Methods. The color yield, following surface modifications of cotton with the quaternary monomers and dyeing was evaluated using K/S measurements.

2. Experimental 2.1 Materials and chemicals Cotton twill fabric (bleached and mercerized, 15 cm x 15 cm) was used in this work. DADMAC (Figure 1a) solution (65 wt. % in H2O) and AOETMAC (Figure 1b) solution (80 wt. % in H2O) was purchased from Sigma Aldrich. Figure 1c shows the 4 ACS Paragon Plus Environment

Page 5 of 26

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


chemical structure of 1, 1, 2, 2-tetrahydroperfluorododecyl acrylate (THPFDA), which was obtained from Daikin America. Ultrahigh pure helium (grade 5.0, 99.999% Helium) supplied by Machine and Welding Co., North Carolina was used to generate plasma. Direct dyes (C. I. Direct Yellow 106; 100%, C.I. Direct Blue 106; 180% and C. I. Direct Red 80; 100%) were purchased from Crompton and Knowles Colors, Inc. North Carolina. A conventional repellent finish containing 70 g/L fluorocarbon polymer, 50 g/L wax extender, 15 g/L silicone softener, and 20 g/L polyethylene softener was pad applied to the cotton fabric at 75% wet pick up, dried at 120 °C and cured at 175 °C for one minute 36.

2.2 Atmospheric pressure plasma jet system (APJeT) Plasma polymerization was carried out using the e-RioTMAtmospheric Pressure Plasma System Model APPR-D300-13 (APJeT, Inc. Santa Fe, New Mexico) (Figure 2). It is a glow-discharge plasma reactor having dimensions of 33 cm x 12.5 cm powered by a RF (13.56 MHz) power supply and a matching network. The substrate is passed under the plasma volume at a certain distance that can be adjusted externally with the use of a synchronized adjustment screw. All plasma experiments in this study were carried out in the downstream mode. Preliminary study included a series of experiments with varied plasma applied power ranging from 400W to 800W and plasma exposure times of 30 sec to 120 sec. Conditions were optimized beyond which there was no significant difference in color yield of the dyed cotton fabrics. Monomer concentration was found to be the most significant factor. Plasma power of 675W was 5 ACS Paragon Plus Environment


1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60

used to generate helium plasma at a flow of 40 L/min. The distance between substrate surface and electrode is kept at approx. 4mm. For induced graft polymerization of DADMAC and AOETMAC, fabrics were exposed into plasma in three ways. i. pre-plasma before padding, ii. post-plasma after padding and iii. plasma treatment before and after padding. In the pre-plasma treatment, fabrics were exposed to plasma for 1 min on both sides and then immediately padded in aqueous solutions of DADMAC (10 - 30 g/L). The padded fabrics were dried at 60°C for 3 min. In post-plasma after padding, fabrics were padded in aqueous solutions of DADMAC (10 - 30 g/L) and plasma treatment were performed on each side. In plasma treatment before and after padding, fabrics were exposed to plasma for 1 min on both the sides and then immediately padded in aqueous solutions of DADMAC (10 - 30 g/L) or AOETMAC (1 - 28 g/L). The padded fabrics were dried at 60°C for 3 min. Then, the fabrics were plasma treated again by running the fabric through the plasma chamber twice, each run was for 30 sec. 2.3 Dyeing Procedure Dyeing of cotton fabrics treated and untreated with quaternary monomers was carried out in an AHIBA TEXOMAT, Model 1000 (Salvis AG, Switzerland). Three dyes were used in this experiment namely: C. I. Direct Blue 106 , C. I. Direct Red 80 and C. I. Direct Yellow 106 (Figure 3). Fabrics were dyed by the procedure prescribed by Crompton and Knowles Colors, Inc. for direct dyes (atmospheric dyeing procedure and after treatment), at a liquor ratio of 50:1, in the presence of 0.1 6 ACS Paragon Plus Environment

Page 6 of 26

Page 7 of 26

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


g/L of soda ash and 20 g/L of Glauber’s salt (only for control samples) using 1% dye on the weight of the fabric. Fabric was immersed in the dyeing bath at 50°C for 5 min. The temperature was slowly raised (2°C per min) to 100°C and the dyeing was continued for 40 min. Twenty grams of salt (Na2SO4) was divided into three equal parts. First part (6.67g) was added in the dye-bath at 40 min of dyeing process and the remaining two parts were added thereafter every five min. After 50 min, the dyeing solution was cooled to room temperature. Dyed fabrics were rinsed in cold water followed by washing in 2 g/L of non-ionic detergent at 80°C for 15 min and dried at 60°C for 5 min. 2.4 Washing Test Method AATCC Test Method 61 (2A conditions), Colorfastness to Laundering, Home and Commercial: Accelerated (equivalent to ISO Test Method 105 C- 06- 2A) was performed to study the colorfastness of dyed cotton fabrics to laundering 37. Samples subjected to this test should show color change similar to that produced by five home launderings at medium or warm setting. Cotton samples were paired with a multifiber strip, then accelerated washing in the temperature range of 48 ± 3°C was performed with a detergent solution and stainless steel balls. Color change of the sample and staining of the multi-fiber strip were evaluated according to the grayscale.

2.5 Evaluation of dyed fabrics The color strength K/S of dyed fabric was measured using a Datacolor Spectra Flash SF600X (Datacolor) and was assessed using Kubelka-Munk equation 7 ACS Paragon Plus Environment


1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60

K/S = (1-R)2/2R where R is the reflectance of the dyed fabric at λmax, K is the absorption coefficient, and S is the scattering coefficient. A four-layer fabric sample was measured four times by rotating the sample 90 degrees between each measurement, and the average value was recorded. 2.6 Plasma-inducted graft polymerization of THPFDA 1, 1, 2, 2-tetrahydroperfluorododecyl acrylate (THPFDA) was vapor deposited at a flow rate of 1 ml/min and plasma was used for graft polymerization on dyed fabric.

2.7 Lightfastness Test Light fastness was performed in a Ci3000 + Xenon Weather-Ometer®/FadeOmeter® manufactured by Atlas Materials Testing Solutions, following AATCC TM16-2004. Two borosilicate filters were used to simulate outdoor conditions. Fabrics were exposed to UV for 20 and 40 hours. The energy was measured at 340 nm, which is about 1% of the energy in the UV range. The irradiation (IR) was set at 0.55 W/m2, which gives 1.98 kj in one hour. The following Equation was used to calculate the amount of energy produced in a number of hours: IR x 3.6 x # light hours = #kj. The 3.6 is constant (3600 sec/hr), where IR=0.55 W/m2. Color change of the samples was evaluated using the blue scale.


Page 8 of 26

Page 9 of 26

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


3. Results and Discussion 3.1. Enhancing the dyeability of cotton using DADMAC quaternary monomer The quaternary monomer DADMAC was plasma graft polymerized (Figure 4) to study its cationic effect on enhancing the dyeability of cotton with C. I. Direct Blue 106. Plasma treatment conditions were kept constant and DADMAC concentration was varied from 10 to 30 g/L. Prior to dyeing, cotton was treated with plasma before and/or after padding the fabric (1min each side) with aqueous solutions of (10 to 30 g/L) DADMAC (100% wet pick up, dried at 60°C for 3 min). Plasma treatments were also compared to conventional pad-dry-cure method, where samples were padded followed by drying at 100°C for 2 min and heat curing at 160°C for 90 sec and dyed using the same dyeing procedure. After dyeing and washing, prior to K/S measurements, samples were conditioned at relative temperature and humidity overnight. Figure 5 shows a schematic representation of the quaternary ammonium poly DADMAC grafted on cotton surface and is ionically bonded to direct dye molecules. Table 1 shows the color strength values of cotton pre-treated with different DADMAC concentrations, cured thermally or plasma treated using different combinations and dyed using C. I. Direct Blue 106, along with the corresponding values of the untreated cotton fabric before and after testing for colorfastness to laundering . It is found that the color yield of the fabrics pre-treated with DADMAC was enhanced and a reasonable increase in the K/S values was observed as the concentration of DADMAC increased from 10 to 30 g/L. However, the color yield of



1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60

fabrics that were treated using plasma before and after padding with DADMAC was lower than that of the pre-plasma or post-plasma treatment alone. Greater K/S values, following laundering, were achieved in the samples that were plasma treated after padding than those that were prior and/or post plasma treated or heat cured. Samples treated with 30g/L DADMAC retained upto 140% more color strength compared to the control sample. Table 2 shows the color change and staining as a result of washing procedure. It was found to improve as a result of DADMAC polymerization by thermal curing or plasma curing.

3.2. Enhancing cotton dyeability using AOETMAC quaternary monomer Three dyes, C. I. Direct Yellow 106 and C. I. Direct Red 80, and C. I. Direct Blue 106 were used. The quaternary monomer AOETMAC was plasma-induced graft polymerized onto cotton fabric (Figure 6) to study its effect of cationic nature on enhancing the dyeability of cotton fabric when dyed with different direct dyes. Plasma treatments were compared with conventional pad-dry-cure method, where samples were padded followed by drying at 100°C for 2 min and heat curing at 160°C for 90 sec and dyed using the same dyeing procedure. Figures 7-9- show the effect of different concentrations of AOETMAC on the dyeability of cotton fabrics using C. I. Direct Blue106, C. I. Direct Red 80 and C. I. Direct Yellow 106, respectively. Figure 7 shows the K/S values of cationized cotton dyed with C. I. Direct Blue 106. The K/S value increased with the increase in the concentration of AOETEAC up to 20 g/L. At 20 g/L of AOETMAC, the color yield 10 ACS Paragon Plus Environment

Page 10 of 26

Page 11 of 26

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


increased by 148% (before washing) and 251% (after washing) for plasma treated fabric compared to the control. However, for heat cured fabric, the color yield increased by 20% (before washing) and 28% (after washing) at 20 g/L. The K/S values decreased after 20 g/L of AOETMAC for plasma treated fabric while it remained the same for heat cured fabric. Figure 8 shows the K/S values for cationized cotton dyed with C. I. Direct Red 80.

The K/S values increased with the increase in

the concentration of AOETEAC. For plasma treated fabric at 20 g/L, the K/S increased by 65% before washing. However, after washing, the highest K/S was observed at 28 g/L and is increased by 101% compared to the control. For heat cured fabric, at 20 g/L the K/S value increased by 6% and 40% before and after washing, respectively compared to the control. Figure 9 shows the K/S of cationized cotton dyed with C. I. Direct Yellow 106. For plasma treated fabric at 24 g/L, K/S increased by 25% before washing. However, after washing, the highest K/S was observed at 28 g/L and increased by 93% compared to the control. For heat cured fabric, the K/S values at 28 g/L remained the same as the control before washing. However, after washing it is increased by 17%. These results indicate that the color strength of dyed fabric not only depends on the concentration of cationic monomer but also on the graft polymerization approach of the quaternary ammonium salt.3.3. Lightfastness

This study was conducted to investigate the likelihood of enhancing the photostability of direct dyes on cotton. THPFDA was vapor deposited at a flow rate of 1 ml/min and plasma was used for graft polymerization. Table 3 shows light fastness of 3 dyes (Direct Blue 106, Direct Red 80 and Direct Yellow 106) for control fabric, 11 ACS Paragon Plus Environment


1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60

fabric treated with AOETMAC only and fabric treated with AOETMAC followed by THPFDA treatment after 20 and 40 hours of UV exposure. The results showed that cotton samples treated with AOETMAC had no effect on the photostability of these dyes as compared to control. However, the photostability of dyed fabric that were AOETMAC treated followed by THPFDA treatment was improved. This is because perfluoroalkyl groups are strong electron withdrawing

38, 39

and acceptor system and

can act as a radical scavenger, and therefore protects the dyes against the UV fading.

4. Conclusions Plasma-induced graft polymerization of DADMAC and AOETMAC on cotton fabrics enhanced the color yields of direct dyes considerably. Plasma treatment of cotton fabrics before or after padding with DADMAC furnished better activated cotton surfaces (for C. I. Direct Blue 106) than that of the plasma treatment before and after padding and are comparable to heat curing. Color yield of cotton was enhanced as a result of DADMAC polymerization and and gave a good colorfastness to laundering. However, with AOETMAC, plasma treatment of cotton fabrics before and after padding furnished better activated cotton surfaces for direct dyes than that of the plasma treatment before or after padding or heat curing, which was inferred from the better K/S values. Moreover, furnishing a flurorocarbon layer on dyed cotton enhanced the lightfastness of the direct dyes because fluorocarbons are strong electron acceptors, and, therefore, can act as strong electron scavengers. The procedures outlined in this work can provide better activated cotton surfaces for dyeing with 12 ACS Paragon Plus Environment

Page 12 of 26

Page 13 of 26

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


direct and potentially acid dyes without any thermal input. Additional work is needed to demonstrate commercial feasibility.

Acknowledgment The authors are grateful to Cotton Inc. for the financial support.



1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60

5. References (1) (2) (3)

(4) (5)

(6)

(7)

(8) (9)

(10)

(11)

(12)

(13)

(14)

Hauser, P..; Helfrich, S. G. Heather dyed fabric and method of producing same 1997, US5667533 A. Hauser, P., Reducing Pollution and Energy Requirements in Cotton Dyeing. Text. Chem. Color AM. D. 2000, 32, 44. Cationic Technology: http://msdssearch.dow.com/PublishedLiteratureDOWCOM/dh_0937/0901b80 38093742a.pdf?filepath=productsafety/pdfs/noreg/23301201.pdf&fromPage=GetDoc, Accessed date: 03/15/2016. Hauser, P.; Tabba, A. H., Dyeing of cationic cotton with fiber reactive dyes: Effect of reactive chemistries. AATCC Review 2002, 5, 36. Hebeish, A.; Hashem, M.; Abdel-Rahman, A.; El-Hilw, Z., Improving easy care nonformaldehyde finishing performance using polycarboxylic acids via precationization of cotton fabric. J. Appl. Polym. Sci. 2006, 100, 2697. Malshe, P.; Mazloumpour, M.; El-Shafei, A.; Hauser, P., Functional Military Textile: Plasma-Induced Graft Polymerization of DADMAC for Antimicrobial Treatment on Nylon-Cotton Blend Fabric. Plasma Chem. Plasma Process. 2012, 32, 833. Mazloumpour, M.; Malshe, P.; El-Shafei, A.; Hauser, P., Conferring Durable Antimicrobial Properties on Nonwoven Polypropylene via PlasmaAssisted Graft Polymerization of DADMAC, Surf. Coat. Tech. 2013, 224, 1. PEOPLE. C&EN 1968, 46, 36. Patiño, A.; Canal, C.; Rodríguez, C.; Caballero, G.; Navarro, A.; Canal, J., Surface and bulk cotton fibre modifications: plasma and cationization. Influence on dyeing with reactive dye. Cellulose 2011, 18, 1073. Shahidi, S.; Ghoranneviss, M.; Moazzenchi, B.; Anvari, A.; Rashidi, A., Aluminum coatings on cotton fabrics with low temperature plasma of argon and oxygen. Surf. Coat. Tech. 2007, 201, 5646. Bhattacharya, A.; Rawlins, J.; Ray, P.; Wiley, I. Polymer grafting and crosslinking: http://site.ebrary.com/lib/alltitles/docDetail.action?docID=10275746, Accessed: 3/16/2016 Morent, R.; De Geyter, N.; Verschuren, J.; De Clerck, K.; Kiekens, P.; Leys, C., Non-thermal plasma treatment of textiles. Surf. Coat. Tech. 2008, 202, 3427. Inbakumar, S.; Morent, R.; De Geyter, N.; Desmet, T.; Anukaliani, A.; Dubruel, P.; Leys, C., Chemical and physical analysis of cotton fabrics plasma-treated with a low pressure DC glow discharge. Cellulose 2010, 17, 417. Sun, D.; Stylios, G., Fabric surface properties affected by low temperature plasma treatment. J. Mater. Process. Technol. 2006, 173, 172.


Page 14 of 26

Page 15 of 26

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


(15)

(16)

(17)

(18)

(19)

(20) (21)

(22)

(23)

(24)

(25) (26) (27)

(28)

(29)

Costa, T.; Feitor, M.; Alves Jr, C.; Freire, P.; de Bezerra, C., Effects of gas composition during plasma modification of polyester fabrics. J. Mater. Process. Technol. 2006, 173, 40. Negulescu, I.; Despa, S.; Chen, J.; Collier, B.; Despa, M.; Denes, A.; Sarmadi, M.; Denes, F., Characterizing Polyester Fabrics Treated in Electrical Discharges of Radio-Frequency Plasma. Text. Res. J. 2000, 70, 1. Tsai, P.; Wadsworth, L.; Roth, J., Surface Modification of Fabrics Using a One-Atmosphere Glow Discharge Plasma to Improve Fabric Wettability. Text. Res. J. 1997, 67, 359. Verschuren, J.; Van Herzele, P.; De Clerck, K.; Kiekens, P., Influence of Fiber Surface Purity on Wicking Properties of Needle-Punched Nonwoven after Oxygen Plasma Treatment. Text. Res. J. 2005, 75, 437. Wróbel, A.; Kryszewski, M.; Rakowski, W.; Okoniewski, M.; Kubacki, Z, Effect of plasma treatment on surface structure and properties of polyester fabric. Polym. 1978, 19, 908. Li, S.; Jinjin, D., Improvement of hydrophobic properties of silk and cotton by hexafluoropropene plasma treatment. Appl. Surf. Sci. 2007, 253, 5051. Zhang, J.; France, P.; Radomyselskiy, A.; Datta, S.; Zhao, J.; van Ooij, W., Hydrophobic cotton fabric coated by a thin nanoparticulate plasma film. J. Appl. Polym. Sci. 2003, 88, 1473. Chaivan, P.; Pasaja, N.; Boonyawan, D.; Suanpoot, P.; Vilaithong, T., Lowtemperature plasma treatment for hydrophobicity improvement of silk. Surf. Coat. Tech. 2005, 193, 356. Hochart, F.; De Jaeger, R.; Levalois-Grützmacher, J., Graft-polymerization of a hydrophobic monomer onto PAN textile by low-pressure plasma treatments. Surf. Coat. Tech. 2003, 165, 201. Vaswani, S.; Koskinen, J.; Hess, D., Surface modification of paper and cellulose by plasma-assisted deposition of fluorocarbon films. Surf. Coat. Tech. 2005, 195, 121. Hegemann, D., Stain Repellent Finishing on Fabrics. Adv. Eng. Mater. 2005, 7, 401. Karahan, H.; Özdoğan, E., Improvements of surface functionality of cotton fibers by atmospheric plasma treatment. Fibers Polym. 2008, 9, 21. Yuranova, T.; Rincon, A.; Bozzi, A.; Parra, S.; Pulgarin, C.; Albers, P.; Kiwi, J., Antibacterial textiles prepared by RF-plasma and vacuum-UV mediated deposition of silver. J. Photochem. Photobiol., A 2003, 161, 27. Gawish, S.; Matthews, S.; Wafa, D.; Breidt, F.; Bourham, M., Atmospheric plasma-aided biocidal finishes for nonwoven polypropylene fabrics. I. Synthesis and characterization. J. Appl. Polym. Sci. 2007, 103, 1900. Wakida, T.; Tokino, S.; Shouhua Niu; Lee, M.; Uchiyama, H.; Kaneko, M., Dyeing Properties of Wool Treated with Low-Temperature Plasma Under Atmospheric Pressure. Text. Res. J. 1993, 63, 438.



1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60

(30)

(31) (32)

(33)

(34)

(35) (36) (37) (38)

(39)

Tsafack, M.; Levalois-Grützmacher, J., Towards multifunctional surfaces using the plasma-induced graft-polymerization (PIGP) process: Flame and waterproof cotton textiles. Surf. Coat. Tech. 2007, 201, 5789. Lu, S.-Y.; Hamerton, I., Recent developments in the chemistry of halogen-free flame retardant polymers. Prog. Polym. Sci. 2002, 27, 1661. Lam, Y.; Kan, C.; Yuen, C., Effect of plasma pretreatment on enhancing wrinkle resistant property of cotton fiber treated with BTCA and TiO2 System. J. Appl. Polym. Sci. 2012, 124, 3341. Zanini, S.; Massini, P.; Mietta, M.; Grimoldi, E.; Riccardi, C., Plasma treatments of PET meshes for fuel–water separation applications. J. Colloid Interface Sci. 2008, 322, 566. Kan, C.; Yuen, C., Static properties and moisture content properties of polyester fabrics modified by plasma treatment and chemical finishing. Nucl. Instrum. Methods Phys. Res., Sect. B 2008, 266, 127. Shahidi, S., Plasma sputtering as a novel method for improving fastness and antibacterial properties of dyed cotton fabrics. J. Text. I. 2015, 106, 162. Tyner, D. Evaluation of Repellent Finishes Applied by Atmospheric Plasma. North Carolina State University, Raleigh, NC, US, 2007. Technical Manual. In American Association of Textile Chemists and Colorists: North Carolina, USA, 2010. Li, Y.; Tan, L.; Wang, Z.; Qian, H.; Shi, Y.; Hu, W., Air-Stable n-Type Semiconductor: Core-Perfluoroalkylated Perylene Bisimides. Org. Lett. 2008, 10, 529. Sun, H.; Putta, A.; Kloster, J.; Tottempudi, U., Unexpected photostability improvement of aromatics in polyfluorinated solvents. Chem. Commun. 2012, 48, 12085.


Page 16 of 26

Page 17 of 26

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


Abbreviations:

DADMAC: diallyldimethylammonium chloride AOETMAC: [2-(acryloyloxy) ethyl] trimethylammonium chloride THPFDA: 1,1,2,2-tetrahydroperfluorododecyl acrylate CHPTAC: 3-chloro-2-hydroxypropyltrimethyl ammonium chloride AATCC: American Association of Textile Chemists and Colorists APPR: Atmospheric pressure plasma reactor USFDA: U. S. Food and Drug Administration HCAP: Heat curing after padding PrePBP: Pre-plasma before padding PostPAP: Post-plasma after padding PlasmaBAP: Plasma treatment before and after padding



1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60

a.

diallyldimethylammonium chloride (DADMAC).

b. [2-(acryloyloxy) ethyl] trimethylammonium chloride (AOETMAC)

c.

1,1,2,2-Tetrahydroperfluorododecyl acryla(THPFDA) Figure 1. Chemical structures of a) DADMAC, b) AOETMAC and c) THPFDA.


Page 18 of 26

Page 19 of 26

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


Figure 2. A schematic diagram of the pressure plasma reactor APPR-D300-13 device.

Direct Blue 106 (λmax 610)



1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60

Red 80 (λmax 530)

Yellow 106 (λmax 430) Figure 3 Chemical structures of Direct Blue 106, Direct Red 180 and Direct Yellow 106.

Figure 4. Free radical polymerization mechanism of DADMAC.


Page 20 of 26

Page 21 of 26

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


Figure 5. Dyeing cationized cotton.

R

N O

H2C

CH n

Cl O

R

O

+

O

N Cl Figure 6. Free radical polymerization mechanism of AOETMAC.



1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60

Figure 7. Effect of the quaternary monomer (AOETMAC) concentration (g/L) on the dyeability of Direct Blue 106 for Cotton.

Figure 8. Effect of the quaternary monomer (AOETMAC) concentration (g/L) on the dyeability of Direct Red 80 for Cotton. 22 ACS Paragon Plus Environment

Page 22 of 26

Page 23 of 26

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


Figure 9. Effect of the quaternary monomer AOETMAC concentration (g/L) on the dyeability of Direct Yellow 106 for Cotton.



1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60

Page 24 of 26

Table 1. Effect of concentrations of DADMAC and treatment conditions on the dyeability of cotton with direct blue 106 Color Yield (K/S) Before Washings

After Washings

Control

2.84

2.26

Conc.of DADMAC

HCAP

PrePBP

PostPAP Plasma

(g/L)

HCAP

PrePBP

PostPAP Plasma

BAP

BAP

10

6.48

-

5.59

4.63

3.94

-

4.75

2.74

20

7.2

6.64

5.66

5.94

3.5

4.63

4.43

3.76

30

7.09

6.77

6.82

5.34

4.47

3.81

3.98

3.83

*HCAP:Heat curing after padding; PrePBP: Pre-plasma before padding; PostPAP: Post-plasma after padding; PlasmaBAP: Plasma treatment before and after padding.

Table 2.Grayscale for color change and staining Grayscale Color Change

Staining

Control

3-4

2-3

Conc.of

HCAP

PrePBP

PostPAP Plasma

DADMAC (g/L)

HCAP

PrePBP

PostPAP Plasma

BAP

BAP

10

3-4

-

3-4

3-4

3

-

3-4

3-4

20

4

3-4

4

3-4

3-4

3

3-4

3

30

3

3-4

3-4

3-4

3

3

3-4

3-4


Page 25 of 26

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


Table 3. Lightfastness of Direct Blue 106, Direct Red 80, and Direct Yellow 106 Lightfastness Direct Blue 106 after 20 hr

Direct Red 80 after Direct Yellow 106 after

40 hr

20 hr

40 hr

20 hr

40 hr

Controla

3

2-3

2

1

3

2

AOETMACb

3

2-3

2

1

3

2

THPFDAc

5

4

3

2

4

3

a

cotton fabric without treatment plasma treated cotton before & after padding with 20 g/L AOETMAC c plasma treated cotton before & after padding with 20 g/L AOETMAC followed by THPFDA treatment. b



1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60

For Table of Contents Only


Page 26 of 26

Plasma Induced Graft Polymerization of Cationic and Fluorocarbon

Recommend Documents