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Textile Research Journal

DOI: 10.1177/0040517508090486 2008; 78; 311 Textile Research Journal

Daryoush Abedi, Sayed Majid Mortazavi, Mohammad Khajeh Mehrizi and Mahmoud Feiz Antimicrobial Properties of Acrylic Fabrics Dyed with Direct Dye and a Copper Salt

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Textile Research Journal Article

Textile Research Journal Vol 78(4): 311–319 DOI: 10.1177/0040517508090486 www.trj.sagepub.com © 2008 SAGE PublicationsFigures 6,7 appear in color online: http://trj.sagepub.com Los Angeles, London, New Delhi and Singapore

Antimicrobial Properties of Acrylic Fabrics Dyed with Direct Dye and a Copper Salt

Daryoush Abedi1 Department of Pharmaceutical Biotechnology and Isfahan Pharmaceutical Sciences Research Center, School of Pharmacy, Isfahan University of Medical Sciences, Isfahan, 81745-359, Iran

Sayed Majid Mortazavi, Mohammad Khajeh Mehrizi and Mahmoud FeizDepartment of Textile Engineering, Isfahan University of Technology, Isfahan, Iran

There is a general trend towards increasingly stringenthygiene standards. Antibacterial fibers work by controllingthe multiplication of micro-organisms, and thus suppress-ing the generation of unpleasant odor [1].

Textiles are carriers of micro-organisms such as patho-genic bacteria and odor-generating bacteria. Controlling thegrowth of bacteria on fibers or fabrics may be achieved by: a)a finishing process in which an antibacterial additive is fixedon the surface of the material by a resin, b) grafting of antibac-terial agents on the cellulose chain, or c) incorporating agentsinto spinning solution of regenerated fibers. The finishingprocess is the technique most frequently employed to impartantibacterial activity to textiles. However, the durability tolaundering achieved by this technique is usually not as goodas that obtained by other methods, such as grafting or incor-

poration. In comparison to an incorporation process, graft-ing is a more complicated and expensive technology [2–4].1

The main antimicrobial agents used in textiles includeorgano-metallic compounds, phenols, quaternary ammo-nium salts and organo-silicons. To be successful in the mar-ketplace, these finishing agents should be durable and haveselective activity towards undesirable organisms. Safety,non-toxicity and biodegradability are required for antimi-

Abstract In this research work, acrylic fabricwith an antimicrobial function was prepared bydyeing with C.I. Direct Blue 168 and copper sul-fate as mordanting agent. The effects of variousfactors which may affect the antimicrobial prop-erty of the treated fabric, such as copper sulfateconcentration and temperature in pre- and post-mordanting procedures, were studied. Antimicro-bial properties of treated fabrics were evaluatedagainst common pathogenous bacteria, Staphylo-coccus aureus and Escherichia coli. Untreatedacrylic fabric showed no antimicrobial behavior,whilst dyed and copper mordanted fabrics pos-sessed considerable antimicrobial properties. Itwas found that the treated fabric with 2 % coppersulfate in pre- and post-mordanting scenariosretained the highest antimicrobial property withgood washing fastness. It was also shown thatusing higher temperature in the mordanting stagecould lead to a higher antimicrobial functionalityon mordanted dyed fabrics. Furthermore, K/Svalue, FTIR spectra, light and washing fastnessesof the treated fabrics were evaluated.

Key words antimicrobial activity, acrylic fab-rics, copper salt, dyeing

1 Corresponding author: Department of Pharmaceutical Bio-technology and Isfahan Pharmaceutical Sciences Research Center,School of Pharmacy, Isfahan University of Medical Sciences, Isfa-han, 81745-359, Iran. Tel: 98 311 792 2606; fax: 98 311 668 0011;e-mail: abedi@mui.ac.ir

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312 Textile Research Journal 78(4)TRJTRJ

crobial agents, and the active ingredients used in antimi-crobial finish need to be registered after they have beendemonstrated effective and safe to use [5].

Recent studies have reported the antibacterial proper-ties of fibers and fabrics, employing different approachessuch as addition of photo-stable inorganic powder as an anti-bacterial additive to the melt polyester stream before spin-ning [1], surface coating by water-based silver colloidalsolution and ethanol-based nanosilver colloids on polyesternonwoven [6], development of antimicrobial cotton fabric bytreatment with the tannin-rich extract of quercus infectoria(QI) plant in combination with aluminum, copper and fer-rous mordants [7]. Such properties are affected by addingvarious metal salts to the substrate [8]. Some researchersinvestigated the effect of a metallic salt treatment on theantibacterial activity of cellulosic fabrics against variouskinds of bacteria. These studies resulted in proving a directrelationship between the degree of antibacterial activity ofsamples, treated with copper salt against S. aureus, and theamount of adsorbed copper ion [2]. Among these ions,some are also expected to work as deodorants [8, 9]. Anumber of these metallic species are considered as pollut-ant and are likely to be restricted in the near future for envi-ronmental reasons [10].

There have been several studies on antimicrobial acrylicfibers containing amino nitrogen [11]. In this regard, the pro-duction of an acid dyeable blend of acrylic fiber and a water-soluble chitosan derivative, N-(2-hydroxy)propyl-3-trimethyl-ammonium chitosan chloride, has been reported [12]. Dur-ing the last few years, some progress has been made towardsintroduction of antimicrobial functionality into acrylic fabricseither by N-halamine moieties or quaternary ammoniumsalts (QAS) [13, 14]. Unfortunately, both treatments maylimit or affect the dyeing properties of the finished acrylicsubstrate because of the chlorine bleach needed in N-hala-mine treatment, while the use of QAS may occupy someavailable dye sites within the fiber structure [15].

Deodorizing on wool samples using ethyl mercapthanhas been reported [7], but in our study properties antimi-crobial activity of treated fabrics against S. aureus andE. coli on acrylic samples depicted durable antimicrobialproperties.

Sawa and Hoten investigated the antimicrobial activityof six basic dyes and benzylkonium chloride as a retarding

agent in the dyed acrylic fibers by means of JIS testmethod. They showed that antimicrobial activity of thedyed samples depended on the chemical structure of dyes.Bactericidal activity against S. aureus was shown in all dyesexcept thiazine, whereas the activity against E. coli wasreported to be low [16]. This research work mainly dealswith the modification of acrylic fabrics using an easy andcost-effective method with good laundering durability. Theprimary objective of this novel work was to fix direct dyeson acrylic fabrics in the presence of copper cations as dyeassistant and simultaneously to achieve durable antibacte-rial properties. The main applications of fabrics producedby this novel procedure would be for medical clothing andfloor-covering.

Experimental

MaterialsAcrylic fabric having plain weave (11 ends and 10 picksthread per cm, 20/2 warp and weft yarn metric, 230 g/m2)was kindly supplied by Poly-Acryl Co. Ltd. (Iran). This fab-ric was produced from 94 % acrylonitril, 5 % methylacr-ylate and a trace of acrylamidomethylpropeosulfate. Theacrylic fabric was soaped with 0.5 % owf nonionic deter-gent at 60 °C for 30 min, then thoroughly rinsed and airdried. Copper sulfate was selected as the metal salt in dye-ing of the acrylic fabric with C.I. Direct Blue 168 (DirectCopper Blue 2B), which was used as a diazo direct dye withformula shown in Figure 1.

Dyeing procedure (treatment) was carried out in anAHIBA 1000 Polymath apparatus made by Data ColorCompany. The maximum absorbance of all used bacterialconcentration was measured at λ = 580 nm using spectro-photometer, Spectronic 70 [17].

Cultures of the following micro-organisms were used inthis research work: Staphylococcus aureus ATCC 6538 andEscherichia coli ATCC 4157.

Dyeing MethodThe dyeing process consisted of three steps: pre-mordant-ing, dyeing and post-mordanting. In pre-mordanting stage,

Figure 1 Chemical structure of C.I. Direct Blue 168.

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Antimicrobial Properties of Acrylic Fabrics Dyed with Direct Dye and a Copper Salt D. Abedi et al. 313 TRJ

0.5–15.0 % owf metal salt solutions were prepared by dis-solving the metal salts in hot water. Acrylic fabric (3 g) wasthen immersed in the solution at a liquor ratio of 30:1 for150 min at 50–95 °C. Fabrics were then washed with deion-ized water and air dried at room temperature. After thepre-metallization stage, the samples were soaked in a dye-bath comprising 3 % owf dye, 3 % owf acetic acid (5 %)and a liquor ratio of 30:1. The dyebath temperature wasraised from 25 °C to 100 °C in 30 min and then kept at100 °C for 90 min. Post-mordanting step commenced byimmersing the rinsed and air dried dyed samples in anaqueous solution of 1–4 % metal salt and liquor ratio of30:1 for 30 min at 80 °C and 100 °C. The samples were thenthoroughly rinsed and air dried.

Antimicrobial PropertiesMordanted and dyed fabrics were washed in a Launder-Ometer according to AATCC 61-1994 test method to eval-uate their washing durability. One cycle of a Launder-Ometer washing test by AATCC test method is consideredequivalent to five home laundering cycles.

The antimicrobial properties of fabrics were quantita-tively evaluated against S. aureus, a gram-positive bacte-rium and E. coli, a gram-negative bacterium, according toAATCC 100-1993 test method. Circular fabric swatches(about 1 g) were challenged with 1.0 ± 0.1 ml of bacterialinoculum in a 250 ml container. The inoculum was a nutri-ent broth culture containing 1.0 × 104–1.0 × 106 colonyforming units (CFU)/ml of bacteria. After bringing the con-trol (untreated acrylic) and test swatches in contact withbacteria for 24 hours, 100 ml of sterilized distilled water waspoured into the vessel and vigorously shook prior to thedilution of the supernatant to 103 ml. The diluted solutionaliquots were plated on a nutrient agar and incubated for 18hours at 37 °C. Viable colonies of bacteria on the agar platewere counted, and the reduction in numbers of bacteria wascalculated using equation (1):

Reduction rate (%) = (A – B)/A*100 (1)

where A and B are the number of bacterial colonies fromuntreated and treated fabrics, respectively [18].

Color StrengthThe relative color strength (K/S) of dyed fabrics was meas-ured by the light reflectance technique using the Kubelka-Munk equation (2) [19]:

K/S = (1 – R)2/2R (2)

The reflectance (R) of the dyed fabrics was measured ona reflectance model Carry Vis-uv 300 spectrophotome-ter.

Light and Washing FastnessDyed samples were tested according to ISO standardmethods for fastness measurements; ISO 105 C03 (1989)for evaluating color fastness to washing and ISO 105 B02(1989) for color fastness to light.

Results and Discussion

The mechanism of interaction between acrylic fabric andcopper sulfate was considered as the following:

1. absorption of aqueous copper ions into the fabric2. formation of a strong covalent bond between copper

and the pendant nitril groups of acrylic polymers[20].

Figure 2 shows schematically the mechanism of binding ofcopper ions to acrylic fibers. Coordination bonds formedamong the copper, dye and acrylic polymers, which hav-ing a strong affinity for copper ions, ensured that theabsorbed copper was strongly bound. Copper ions (II) inthese mechanisms could form a coordination bond withboth polymers and the donor groups in the dye structure.Preliminary experiments were performed to dye acrylicfabrics in the presence of CuSO4 and hydroxylamine incomparison to dyeing in the presence of CuSO4 alone.The results of these two different pre-mordanting experi-ments were identical. Table 1 shows the mean, standarddeviation (SD) and number of available samples undervarious conditions.

Effect of temperatureThe temperature effect was studied in two stages: pre-mor-danting and post-mordanting. Treated fabrics with differ-ent temperatures in pre-mordanting were screened fortheir antimicrobial activity against S. aureus. The pre-mor-danting conditions under which the fabrics were treatedare summarized in Table 2. The antimicrobial properties ofthe treated fabrics under various pre-mordanting condi-tions are depicted in Figure 3. Durability of antimicrobialactivity to washing is one of the major concerns of textileresearchers and users, since textiles are subjected to fre-quent laundering. Figure 3 shows the antimicrobial proper-ties of treated fabrics after repeated home launderings. Asshown, the antibacterial activity after two home launderingcycles of all sample fabrics was not reduced. However,increasing the washing cycles to eight could decrease theantibacterial activity of samples around 90–99 %. The fab-ric sample 4, which underwent pre-mordanting at 95 °C,demonstrated the greatest durability of antimicrobial activ-ity among all the fabric samples. The difference in antimi-

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314 Textile Research Journal 78(4)TRJTRJ

crobial activity of various fabric samples may have arisenfrom their different glass transition temperatures (Tg). Byincreasing the temperature to 95 °C at sample 4, a moreopen structure of the fabric was obtained, and hence more

active sites were available. Consequently, more copperions reacted, resulting in more copper ions (II) attached tothe fabrics [15, 21].

To study the effect of post-mordanting bath tempera-ture on the antimicrobial activity of the studied acrylic fab-ric, acrylic fabrics were treated for 30 min at 80 °C and 100°C (Table 3). Antimicrobial activity of the treated fabricsunder various temperatures at post-mordanting stage isshown in Figure 4. It can be seen from the results in Figure4 that samples 5 and 6 retained 90 % and 95 % antibacte-rial activity against S. aureus after eight cycles of Launder-Ometer, respectively. It was concluded that post-mordant-ing of fabrics with copper sulfate was accomplished at thetemperature above the glass transition temperature.Hence, more copper ions (II) reacted to the fabrics, andthus retained durable antimicrobial function after eightlaundering cycles.

Effect of Salt ConcentrationThe effect of salt concentration was also studied in theacrylic pre-mordanting and post-mordanting. Fabricstreated with different concentrations of salt in 95 °C in pre-mordant stage were dyed using C.I. Direct Blue 168 fol-lowed by 2 % owf salt in 100 °C. The results are shown in

Figure 2 The mechanism of interaction between acrylic fibers and copper sulfate.

Figure 3 Antimicrobial activity of available samples inTable 2 against S. aureus to repeated home laundering(mean ± SD, n = 4).

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Antimicrobial Properties of Acrylic Fabrics Dyed with Direct Dye and a Copper Salt D. Abedi et al. 315 TRJ

Figure 5. The amount of copper sulfate exhausted on thefabrics determined their antimicrobial efficacy, and moreimportantly, affected washing fastness of the products. Fig-ure 5 shows the improvement of antibacterial activity of

treated fabrics by increasing salt concentration from 0.5 to2.0 % owf. However, no further improvement was achievedat concentrations of greater than 2 % owf.

Table 4 shows the post-mordanting conditions. The resultsobtained for antimicrobial functionality of treated acrylicfabrics for different concentrations of copper sulfate are pre-sented in Figure 6. As can be seen, the antimicrobial activ-ity against S. aureus after eight cycles of launder decreasedto 90 % for sample 7, but only to 99 % for samples 8 and 9.As evident from Figure 6, there was no significant effect onthe antimicrobial activity above 2 % copper concentration.This could be explained by the fact that in the low copper

Table 1 Mean, standard deviation (SD) and number of available samples under various conditions.

Samples Washing cycle N Mean SD

Sample 1 02468

44444

100.0099.5092.2590.7590.25

0.0000.5770.5001.7071.707

Sample 2 02468

44444

99.9899.7595.5093.2592.00

0.0500.5000.5771.7071.414

Sample 3 02468

44444

99.5099.2398.7596.2596.25

0.5770.9320.9571.5000.957

Sample 4 02468

44444

99.8099.4399.2599.2394.13

0.4000.9320.5000.9323.423

Sample 5 02468

44444

99.9599.8298.1094.2589.20

0.5770.2221.2670.9570.854

Sample 6 02468

44444

99.7099.2299.2298.8795.50

0.4700.9320.9321.0300.707

Sample 7 02468

44444

99.9898.7598.7598.2197.00

0.8180.8570.9571.2200.816

Sample 8 02468

44444

99.1498.8998.1797.9296.75

1.4361.9301.9752.2200.957

Sample 9 02468

44444

99.2598.9597.8296.1290.13

0.9570.8220.7671.6900.854

Figure 4 Antimicrobial activity of available samples inTable 3 against S. aureus to repeated home laundering(mean ± SD, n = 4).

Figure 5 Effect of salt concentration in pre-mordantingagainst E. coli to repeated home laundering.

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316 Textile Research Journal 78(4)TRJTRJ

concentration of the post-mordanting bath, fewer copperions (II) were available to react with the active sites of pen-

dant ligands. As the copper ions concentration increased inthe after-treatment bath, more copper sulfate could beformed on the surface of acrylic fibers, and the antibacte-rial function increased. Therefore, it was concluded that2 % copper sulfate was the optimum concentration whichgave acceptable antibacterial properties.

Assessment of Color StrengthColor strength of treated fabrics was measured by a spec-trophotometer at λmax = 560 nm. Figure 7 shows the effectof copper concentration on K/S values of fabrics in the pre-mordanting step. The results in Figure 7 reflected the factthat using copper in the pre-mordanting stage increasedthe K/S value of treated fabrics. When we did not use saltin pre-mordanting, the color absorbance was very low.However, by adding copper, color strength of treated fab-rics sharply increased. The greatest K/S value was obtainedwhen fabrics were treated with 0.5 % owf copper sulfate.However, at copper concentrations above 0.5 % owf, theK/S value decreased to 4.9 with 2 % copper. Also, itseemed that treating fabric with 2 % owf copper, thecapacity of copper absorbance was at a high level, there-fore, increasing the level of the salt concentration from 2 to

Table 2 Variation of treated fabrics’ temperature in pre-mordanting stage.

Sample code

Pre-mordanting with 10 %owf copper sulfate Dye used,

% owf

Post-mordanting with 2 %owf copper sulfate

Temp. (°C) Time (min) Temp. (°C) Time (min)

1234

50758595

150150150150

3333

80808080

30303030

Table 3 Summary of conditions of treated fabrics under various post-mordanting.

Sample code

Pre-mordanting with 10 %owf copper sulfate Dye used,

% owf

Post-mordanting with 2 %owf copper sulfate

Temp. (°C) Time (min) Temp. (°C) Time (min)

56

9595

150150

33

80100

3030

Table 4 Variation of copper sulfate concentration in post-mordanting stage on treated fabrics.

Sample code

Pre-mordanting with 10 %owf copper sulfate Dye used,

% owf

Post-mordanting

Temp. (°C) Time (min) % owf Temp. (°C) Time (min)

789

959595

150150150

333

124

808080

303030

Figure 6 Effect of salt concentration in post-mordantingagainst S. aureus to repeated home laundering (mean ±SD, n = 4).

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Antimicrobial Properties of Acrylic Fabrics Dyed with Direct Dye and a Copper Salt D. Abedi et al. 317 TRJ

15 % did not affect the K/S value and it was almost constant.The presence of NH2, OCH3, OH and even N2 in direct dyestructure led to the formation of dye-CuSO4 complexesresulting in high exhaustion percentage of the direct dye intothe fabric. However, increasing the copper concentrationabove 0.5 % may cause reduction of azo groups in the dyestructure causing a decrease in dyeing depth. Using higher

concentrations (higher than 2 %) would not change theobserved reduction potential of copper sulfate on azo groups[22].

FTIR analysisThe FTIR spectra of untreated acrylic (sample A) andmordanted-dyed acrylic (sample B) are presented in Fig-ure 8. The typical absorption peaks of untreated acrylic fib-ers (spectrum A) were shown to be at 3539, 2940, 2247,1738, 1454, 1358, 1249 and 1075 cm–1, due to the stretchingof OH, CH2, C≡N, C=O, bending deformation of CH2,rocking of CH2, and CH and/or C–O vibration, respectively[22]. The weak peak at 1630 cm–1 was most likely caused bythe impurities of the fibers. Figure 8 indicated that theband at 2247 cm–1 remained unaltered, indicating the nitrilgroups were not involved in the interaction with copperions (II), but the changes that did take place revealed that,in the complex formation, the ions interacted with theother functional groups of polymer. The main changebetween sample A and B was observable at 1668 cm–1

where disappearance of this band in sample B could beattributed to ester group of methylacrylate or carbonylgroup of acrylamidomethylpropeosulfate. It seemed thatoxygen atoms in methylacrylate groups could form a coor-dination bond with copper ions (II). The formed bonds

Figure 7 Color strength of treated fabrics using variousconcentrations of copper sulfate in pre-mordanting step.

Figure 8 FTIR spectra of (A) untreated acrylic and (B) acrylic pre-mordanted with 1 % owf copper sulfate at 95 °C for 150min, dyed and by 2 % owf salt solution at 100 °C for 30 min further-treated.

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318 Textile Research Journal 78(4)TRJTRJ

between copper ions and nitrogen or oxygen atom gener-ally appear in complexes at frequencies lower than 500 cm–1,their recording and assignment being difficult [20–23].

Assessment of Fastness PropertiesTable 5 presents the fastness properties to washing and lightof mordanted-dyed acrylic fabric. It can be seen that copperpre-treatment could increase samples’ light fastness, whereasthe pre-treated samples with no copper possessed the lowestlight fastness. When the washing fastnesses were examined, itcould be seen that there was no significant differencebetween the values on un-treated and pre-treated samples.It should be taken into consideration that, if the wash fast-ness values of pre-treated samples, which were 3–4 timesdarker, were the same as the values for un-treated sample,this would mean that in treated samples the dye-fiber inter-action was stronger which could be considered as a sign ofpossible coordinative copper bridging between the dye andfiber in treated samples. With no such dye-fiber interaction,the washing fastness of pre-treated samples, which were 3–

4 times deeper, would be expected to be lower compared toun-treated sample.

Although comparing the fastness values (Table 5) ofpre-treated samples with 2 % copper solution which werepost-mordanted or not post-mordanted could lead to theconclusion that post-mordanting process may increase dyefastness to both washing and light, reaching a final conclu-sion requires more research into the above-mentionedobservation.

Conclusions

In this study, the antimicrobial properties of acrylic fabricsdyed with C.I. Direct Blue 168 pre- and post-treated by cop-per sulfate were studied. Pre- and post-mordanted sampleswith 1 % and 2 % owf copper sulfate and dyed with thedirect dye exhibited the best antimicrobial activity against S.aureus and E. coli after eight laundering cycles. The highestK/S value was obtained when fabrics were treated with 0.5% owf copper sulfate in pre-mordanting bath, whilst dyedacrylic with no copper ion in pre-mordanting stage pos-sessed the lowest color strength. In FTIR spectra, the mainchange between untreated acrylic (control sample) andmordanted dyed sample was observable at 1668 cm–1 wheredisappearance of this band in mordanted dyed acrylic couldbe attributed to ester group of methylacrylate or carbonylgroup of acrylamidomethylpropeosulfate. Also, light fast-ness of treated samples by various concentrations of copper(II) in pre-mordanting treatment was good, whereas theircolor fastness to washing was moderate.

AcknowledgmentWe wish to thank Mrs. Shafizadegan for her assistance.

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Table 5 Fastness properties of treated acrylic fabrics.

SampleaWashingb

LightA1 B A2

Pre-treated without copper (X)

3 2 4 3

Pre-treated with 0.5 % copper (X)

2–3 2 4 6

Pre-treated with 1.0 % copper (X)

2–3 2 4 6

Pre-treated with 1.5 % copper (X)

3 2 4 5

Pre-treated with 2.0 % copper (X)

3 2 4 5

Pre-treated with 5.0 % copper (X)

3 2 4 5

Pre-treated with 10.0 % copper (X)

3 2 4 5

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3 2 4 5

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2 2 4 4

a Pre-treated samples with mentioned concentration and dyed and post-treated with 2 % copper.b A1 = change in color; B = staining on cotton; A2 = staining on acrylic.c Pre-treated sample with 2 % concentration and dyed and not post-mordanted. X = post-mordanted sample; Y = not post-mordanted sample.

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Antimicrobial Properties of Acrylic Fabrics Dyed with Direct Dye and a Copper Salt D. Abedi et al. 319 TRJ

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