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1 w œwz, 48«1y 2011 Textile Science and Engineering Vl. 48, N. 1, 2011»Ÿy w PVA v Ÿy w³p» Á y 1 w w š œw, 1 w ƒ w ( / k) Phtactive and Antimicrbial Prperties f PVA Films Cntaining Varius Organic Phtactivatrs Ki Sub Lim and Kyung Wha Oh 1 Department f Fiber and Plymer Engineering, Hanyang University,G Seul , Krea 1 Department f Hme Ecnmics Educatin, Chung-Ang University, Seul , Krea (Received January 2, 2011/Accepted February 4, 2011) Abstract: Antimicrbial PVA films cntaining varius phtactivatrs were prepared using a slutin casting methd. Benzphenne, 4,4'-bis(dimethylamin)-benzphenne, 1-hydrxycyclhexyl phenyl ketne, 2-methyl-4'-(methylthi)- 2-mrphlinprpiphenne, thixanthen-9-ne, and 4,4'-dihydrxybenzphenne were selected as the phtactive additives. The UV absrptin, transmittance and radical frmatin, thermal stability, structural and antimicrbial prperties f the prepared films were examined by ESR, UV-vis, DSC, XRD and an antimicrbial test. The results shwed that the UV activated benzphenne, 4,4'-bis(dimethylamin)-benzphenne and thixanthen-9-ne prvided excellent antimicrbial prperties after UVA (365 nm) irradiatin. Keywrds: antimicrbial, ply(vinyl achl), phtactivatr 1., ³ w y l x w z ƒ š [1-3]. p z w ƒ w yw»w ƒwš, š w xw., z jš ƒœ s» y,» ³ w y y jš [4,5]. w w y ƒ š. ƒ, ƒ t» w yw ù ³ ww w w, w w, ƒ w y w š. w³ w w š w ù, ù y» ƒ» ã w Crrespndence t Kyung Wha Oh (kwhah@cau.ac.kr) 2011 The Krean Fiber Sciety /2011-1/ [1-3]. w w³ ƒœ w³» w ƒ ù t ƒ w f ƒ š w yy w ww w w w w [6]. Ÿ w y y ww w ³ Ÿ ƒ» š [7]. Ÿ (phtcatalyst) œ» ƒ w yw ü, ü e ƒ. Ÿ ¾ ww» ypk (TiO 2 ) w ƒ w š [8,9], t TiO 2 gqw w» ³ yw q w Á òw w ³ š ³ k w ƒ [10]. ypk (TiO 2 ) Ÿ nx (400 nm), œ ƒ x w y ƒ w e( OH) r (O 2 ) w» yw y w g k ƒ y j w / y w [8,9]. ù y» w t f w 42

2 »Ÿy w PVA v Ÿy w³p 43 ƒ š š, Ÿ yw œ w w,» Ÿ ypk (TiO 2 ) e ùkü» e ƒ y ù yy ƒ w [9,11].» Ÿ w» Ÿ w, x» Ÿ benzphenne ƒ» Ÿ z e š. benzphenne w³ p š» Ÿ ypk (TiO 2 ) j z ü» Ÿ ü t. q Ÿy 50 ƒ Ÿ q w benzphenne sww» Ÿy 6 w ply(vinyl alchl)»» Ÿy w v w. v UV-vis spectrmeter»» w Ÿ p d w. ƒ q (nm) ƒ j w UVA light(365 nm) z ESR(electr spin resnance) d w UVA z free e y d w. w» Ÿy ƒ w PVA v w DSC(differential scanning calrimetry) X- ray diffractin d w p y p y w š,» Ÿy ƒ w PVA v UVA light(365 nm) z UV-vis spectra d w n y d w. Ÿy w PVA v w w³ l p ww » Ÿy benzphenne (99% pure), 4,4-bis (dimethylamin) benzphenne (98% pure), 4,4 -dihydrxybenzphenne (99% pure), 1-hydrxycyclhexyl phenyl ketne (99% pure), 2-methyl-4'-(methylthi)-2-mrphlinprpiphenne (98% pure) š thixanthen-9-ne(97% pure) Sigma-Aldrich l w w, š ply(vinyl alchl)(atactic, 87-89% hydrlyzed, average M w 85, ,000) w Sigma- Aldrich l w w.» Ÿy acetne w v PVA 80 C 2 k w ww,» Ÿy acetne ww w» w q w e 1 w [11,12].» Ÿy /acetne PVA/distilled water z yw 24 p» w. z plyimide v yw slutin castingw 48 k z»(jeio TECH, OV-11) w 60 C 8 w v w Ÿw p :» Ÿy ƒ w PVA v Ÿw y w» w UV-vis spectrmeter(scinc C., S-4100, Krea) w q 200~800 nm Ÿ (absrbance) d w š, UV-vis spectra d q ƒ j» Ÿy 3 w. z pristine PVA v» Ÿy ƒ w PVA v w UVA(365 nm) n d w w. Ÿy p : UV-vis Ÿ k UV Ÿy ƒ» Ÿy PVA w free e y w» w ESR(electrn spin resnance) Spectrmeter(JEOL C., JES-FA200) w MHz frequency X-band d w. UVA light(spectrline C., CC-81, bandwidth: 365 nm, 8 Watt) 30 z ESR d w free e y w. y p : p DSC(TA Instruments, DSC2010) k 10 C/min 250 C¾ g w (T m ) ( H m ) d w. v X-ray diffractin (Rigaku-denki, Japan) d sƒw Cu K α X-rays (α =1.54), w date 2θ =0.05 Step 5-60 (WAXD)» w. w³ p : w³ Ÿy ƒ w PVA v pristine PVA v y s ³(Staphylcccus aureus ATCC 6538P) ³(Escherichia cli, ATCC 8739) w v (JIS Z 2801) ww.»³ 2.2~ w 5 Petril dish 5 5cm v š v 0.4 ml ³ š r 4watt 8 watt UVA(365 nm) light 2 w 1 2 z 20 ml v û ³ ü v ³ w z 1ml w 9mlƒ x w ³ w. ³ 1ml w Petri dish š š w z C w ³ d w (1) (2) w. Textile Science and Engineering, Vl. 48, N. 1, 2011

3 44» Á y Mb Mc Mb Mc (%) = (2) Mb w³y e(s) = lg (1) Ma: t x³ z ³ s³ Mb: t z ³ s³ Mc: w³ƒœ z ³ s³ Ma x³ w z ³ s³ Mbƒ w s³ ³ ƒ z s³ ³ ù y y y w» w» w. Ma Mb d y w w x š w. w³y e(s) (%) t w³ ƒœ z s³ ³ w Ma sw, x q». 3. š 3.1.» Ÿy Ÿp z ƒ»ÿy» w q Ÿ Figure 1. UV-vis spectra f pristine PVA film and PVA films cntaining 6 types f phtactivatrs; (a) benzphenne, (b) 4,4'- bis(dimethylamin)benzphenne, (c) thixanthen-9-ne, (d) 2-methyl-4'-(methylthi)-2-mrphlinprpiphenne, (e) 1- hydrxycyclhexyl phenyl ketne, and (f) 4,4'-dihydrxybenzphenne. w œwz, 48«1y 2011

4 200~400 nm Ÿƒ w r wš Ÿy kw Ÿp w. Figure 1 pristine PVA v Ÿy (1.0 wt%) w w PVA v 6 w UV-vis spectra Ÿ d ùkü. Ÿy w w PVA film pristine PVA v Ÿ ƒ Ÿy q ƒ [12]. benzphenne 250~300 nm, 4,4'-bis(dimethylamin) benzphenne 300~ 400 nm, thixanthen-9-ne 230~300 nm 350~400 nm, 2-methyl-4'-(methylthi)-2-mrphlinprpiphenne 210~240 nm 300~330 nm, 1-hydrxycyclhexyl phenyl ketne 230~260 nm, š 4,4'-dihydrxybenzphenne 250~400 nm w Ÿp ù kþ. q Ÿp w q w» Ÿy ƒ w d m 200~400 nm q sw k Ÿy 3 w. 4,4'-bis(dimethylamin) benzphenne, thixanthen-9-ne 4,4'-dihydrxybenzphenne sww 3, x w [12] Ÿy z ƒ benzphenne ƒ g 4ƒ Ÿy x ww.»ÿy w PVA v Ÿy w³p » Ÿy Ÿy Figure 2 pristine PVA 4 Ÿy UVA (365 nm) w UV z w ESR (electrn spin resnance) d w free e y w. UV chamber 30 UVA w z ESR d w. PVA UV z vjƒ ùkù 4 Ÿy 4,4'-dihydrxybenzphenne w 4,4'-bis(dimethylamin) benzphenne, thixanthen-9-ne benzphenne UV z magnetic field 340~350 mt vjƒ ùk û. Ÿy sw carbnyl grup(c=o) UV π π * triplet biradical x w» [13]. vj ƒ ƒw free e ƒw w [14]. d Ÿy 4,4'- bis(dimethylamin) benzphenne vj ƒ ƒ f UV z vj ƒ ƒw free e û. thixanthen-9-ne e x y UV z vj ƒ ƒw e x y w. benzphenne UV vj dw ù UV z ƒ w vjƒ ùkû. 4,4'-dihydrxybenzphenne v Figure 2. ESR spectra f pristine PVA and the 4 types f phtactivatrs scanned immediately after UVA (365 nm) irradiatin fr 30 min; (a) UV irradiating and (b) n UV. Textile Science and Engineering, Vl. 48, N. 1, 2011

5 46» Á y j ùkù e x ù y w. 3.3.» Ÿy w PVA v p l q UV Ÿ e 4,4'-bis(dimethylamin) benzphenne thixanthen-9-ne z»ÿy wš sww v w ƒ ƒ r» benzphenne w. Figure 3 pristine PVA v 3 Ÿy 1.0 wt% PVA yww v DSC d w ƒ w v. Table 1 DSC d ey w, T m ( C) H m (J/g) ùküš. ƒ T m ( C) w, 4,4'- bis(dimethylamin)benzphenne wš Ÿy w w PVA v T m pristine PVA v T m w y w. ù 1% ƒ vj ƒw H m ƒw ³ w ƒw v ƒ w š. Ÿy 1wt% w w PVA v DSC curve pristine PVA wš Ÿy T m vjƒ ùkù p (T m ) 47~51 C benzphenne vjƒ ùkù» PVA Ÿ y yww v x ƒ w š w ƒ ³ w x [12]. 3.4.» Ÿy w PVA v y Figure 4 pristine PVA v 3 Ÿy 1.0 wt% w w PVA film X-ray diffractin d w ùkü v. pristine PVA v vj [15] semicrystalline vj ùkü [16]. benzphenne 1.0 wt% w PVA film pristine PVA film v j ƒ 2θ=19.5 w ù 4,4'-bis(dimethylamin) benzphenne w w 2θ =19.8 vj ƒ ƒw y ƒ ƒw 2θ =11.7 vjƒ š, thixanthen-9-ne PVA ƒ 2θ = 20.0 vj ƒ ƒw š 2θ = 11.85, 14.9 vjƒ ƒ û. 4,4'- bis(dimethylamin)benzphenne thixanthen-9-ne xk X-ray diffractin ƒ d, e vjƒ ù ƒ Ÿy PVA ùkù v y ƒ k. Ÿy ƒ v y ƒ DSC ew y w. Figure 3. DSC thermgrams f (a) pristine PVA film and PVA films cntaining 1.0 wt% varius phtactivatrs; (b) 4,4'- bis(dimethylamin)benzphenne, (c) benzphenne, and (d) thixanthen-9-ne. Table 1. Thermal characteristics f the pristine PVA film and PVA films cntaining varius phtactivatrs (1.0 wt%) Phtinitiatr T m ( C) H m (J/g) Pristine PVA ,4'-bis(dimethylamin) benzphenne Benzphenne Thixanthen-9-ne Figure 4. X-ray diffractin patterns f (a) pristine PVA film and PVA films cntaining 1.0 wt% varius phtactivatrs, (b) 4,4'-bis(dimethylamin)benzphenne, (c) thixanthen-9-ne, and (d) benzphenne. w œwz, 48«1y 2011

6 »Ÿy w PVA v Ÿy w³p 47 Figure 5. UV-vis spectra (transmittance) f the pristine PVA film and PVA films cntaining 1.0wt% phtactivatrs after UVA (365 nm) irradiatin fr (a) 1 hur, (b) 2 hurs, and (c) 3 hurs. 3.5.» Ÿy w PVA v Ÿw p Figure 5 3 Ÿy 1.0 wt% w w PVA v pristine PVA v UVA(365 nm, UV light 16 cm) 1, 2 š 3 w z v n d w. q 200~800 nm, 4 film UV ƒw n ƒ w y w. UV ƒ v y ù t UV w w [13] n ƒ ù š ƒw. benzphenne ƒ n w 4,4'-bis(dimethylamin)-benzphenne, thixanthen-9- ne n ƒ. 3.6.» Ÿy w PVA v w³ p w [12] 0.5 wt% 1.0 wt% benzphenne PVA w w v z w³ l p w w w w³ y w. ù» ³ 10 v 3 w, 8 watt UVA(365 nm) light 5 w 1 w Ÿy w w v ³ ³ š. ü w» ³ m 10 wš 5 [v (JIS Z 2801)] x ww, UVA û ww x 0.5% w w w³ w Ÿy 1wt% w. Table 2 Figure 6 benzphenne, 4,4'-bis(dimethylamin)-benzphenne thixanthen-9-ne 1wt% w w PVA v pristine PVA v y s ³ (Staphylcccus aureus ATCC 6538P) ³(Escherichia cli, ATCC N ) w v (JIS Z 2801) w³ sƒw. UVA(365 nm) w³ sƒw» w v ³ w z UVA 1 2 w z w³ s ƒw. Ÿy w³ Ÿy carbnyl UV w triplet e wš PVA H dnr l H ñ š w H 2 O 2 w w³ w [17]. Ÿy sww ³ y s ³ w w³ w ùkû. UVA w 4,4'-bis(dimethylamin)-benzphenne thixanthen-9-ne Ÿy ƒ w PVA v y s ³ ³ ³ 87.5% Textile Science and Engineering, Vl. 48, N. 1, 2011

7 48» Á y Table 2. Antimicrbial test results f pristine PVA and PVA film cntaining varius phtinitiatrs (1 wt%) with UVA irradiatin fr 1 and 2 hurs UV (1H) UV (2H) UV (1H) UV (2H) Staphylcccus aureus Ma Mb Mc Antimicrbial activity (S) Reductin (%) Pristine PVA Benzphenne ,4'-bis(dimethylamin)benzphenne Thixanthen-9-ne Pristine PVA Benzphenne ,4'-bis(dimethylamin)benzphenne Thixanthen-9-ne Escherichia cli Ma Mb Mc Antimicrbial activity (S) Reductin (%) Pristine PVA Benzphenne ,4'-bis(dimethylamin)benzphenne Thixanthen-9-ne Pristine PVA Benzphenne ,4'-bis(dimethylamin)benzphenne Thixanthen-9-ne CFU/ml: clny frming unit. w w w³ ùkþ. ³ 4,4'-bis(dimethylamin) benzphenne w PVA v ƒ ³ 98.5% ³. Ÿy ESR e j ùkû w³ sƒ 1 UV w y s ³ 98.5%, ³ 95.7% ³ w w³ ùk þ 2 z y s ³ 99.5%, ³ 98.2% w w³ ƒw. thixanthen-9-ne w PVA v 1 UV z y s ³ 93.1%, ³ 87.5%. 2 z y s ³ 96.6%, ³ 90.2% ³ ƒw. w [12] w w³ benzphenne w 4,4'-bis(dimethylamin) benzphenne thixanthen-9- ne ³ benzphenne y w. Hng Sun[12] û UVA w 4,4'-bis(dimethylamin) benzphenne thixanthen-9-ne UV ƒ û w w³ ùký y w. 4. ey x» Ÿy w š ƒ w ww, p» p, ü w y w» y wš w. w Ÿy»» s wš Ÿy p š» Ÿy w w p w.» z»ÿy benzphenne sww» Ÿy 6 w ply(vinyl alchl)» w» Ÿy w w v w. v UV-vis spectra»» w Ÿ p d w Ÿ q ƒ š Ÿ w w ESR(electr spin resnance) d w free e sƒw. 4,4'-bis(dimethylamin) benzphenne, thixanthen-9-ne benzphenne UV z magnetic field 340~350 mt vj ùk ü w Ÿy x. v w g ƒ w v, w œwz, 48«1y 2011

8 유기광활성제 함유 PVA 필름의 광활성 및 항균특성 49 Images shwing the effects f pristine PVA and PVA films cntaining 1 wt% varius phtinitiatrs with UVA irradiatin fr 1 and 2 hurs n and in petri dishes. Figure 6. Staphylcccus aureus Escherichia cli 적, 광학적 특성 및 항균특성을 파악하였다. 그 결과 선정 된 광활성제 함유시 필름의 열적 특성 및 결정화도는 1wt% 첨가시 별 변화가 없었으며 4,4'-bis(dimethylamin) benzphenne, thixanthen-9-ne의 경우 약간의 결정화도 가 상승하는 것을 보였다. 필름의 투과도는 benzphenne, Textile Science and Engineering, Vl. 48, N. 1, ,4'-bis(dimethylamin) benzphenne, thixanthen-9-ne 순으로 우수하였다. 항균성은 기존에 자가청정제로 사용된 benzphenne과 비교하였을 때 4,4'-bis(dimethylamin) benzphenne과 thixanthen-9-ne 모두 benzphenne 보 다 낮은 강도의 UVA에서 더 우수한 항균성을 보여 우수

9 50» Á y w ƒ ƒ y w. : w w (Prject N ). š x 1. A. Singh, Y. W. Lee, and W. J. Dressick, Self-cleaning Fabrics fr Decntaminatin f Organphsphrus Pesticides and Related Chemical Agents, Adv Mater, 2004, 16, E.-R. Kenawy, S. D. Wrley, and R. Brughtn, The Chemistry and Applicatins f Antimicrbial Plymers, Bimacrmlecules, 2007, 8(5), G. Sun and S. Dave Wrley, Chemistry f Durable and Regenerable Bicidal Textiles, Jurnal f Chemical Educatin, 2005, 82(1), J. Y. Oh, M. K. Kim, H. S. Sn, and K. D. Zh, A Study n the Degradatin Mechanism f Diazinn and the Acute Txicity Assessment in Phtlysis and Phtcatalysis, Krean Sc Envirn Eng, 2008, 30(11), R. Andrezzi, I. D. Smma, R. Martta, G. Pint, A. Plli, and D. Spasian, Oxidatin f 2,4-dichlrphenl and 3,4- dichlrphenl by Means f Fe(III)-hmgeneus Phtcatalysis and Algal Txicity Assessment f the Treated Slutins, Water Research, 2011, 45, T. S. Kim, J. K. Kim, K. H. Chi, and K. D. Zh, A Study n the Degradatin f Parathin and Reductin f Acute Txicity in Slar TiO 2 Phtcatalysis, Krean Sc Evinrn Eng, 2005, 27(8), A. Mills and S. L. Hunte, An Overview f Semicnductr Phtcatalysis, Jurnal f Phtchemistry and Phtbilgy A: Chemistry, 1997, 108(1), Y. Liu, R. Liu, C. Liu, S. Lu, L. Yang, F. Sui, Y. Teng, R. Yang, and Q. Cai, Enhanced Phtcatalysis n TiO 2 Nantube Arrays Mdified with Mlecularly Imprinted TiO 2 Thin Film, J Hazard Mater, 2010, 182(1-3), B. Tryba, Immbilizatin f TiO 2 and Fe-C-TiO 2 Phtcatalysts n the Cttn Material fr Applicatin in a Flw Phtcatalytic Reactr fr Decmpsitin f Phenl in Water, J Hazard Mater, 2008, 151, K. Qi, X. Wang, and J. H. Xin, Phtcatalytic Self-cleaning Textiles Based n Nancrystalline Titanium Dixide, Text Res J, 2011, 81(1), H. Li, Y. Zhang, S. Wang, Q. Wu, and C. Liu, Study n Nanmagnets Supprted TiO 2 Phtcatalysts Prepared by a Sl-gel Prcess in Reverse Micremulsin Cmbining with Slvent-thermal Technique, J Hazard Mater, 2009, 169(1-3), K. H. Hng and G. Sun, Phtinduced Antimicrbial Plymer Blends with Benzphenne as a Functinal Additive, J Appl Plym Sci, 2009, 112, K. H. Hng and G. Sun, Structures and Phtactive Prperties f Ply(styrene-c-vinylbenzphenne), J Appl Plym Sci, 2008, 46, B. Ranby and J. F. Rabek, ESR Spectrscpy in Plymer Research (Plymers Prperties and Applicatins), Springer- Verlag, Berlin, Heidelberg and New Yrk, 1977, 1, pp H. Chen, H. Xu, and P. Cebe, Thermal and Structural Prperties f Blends f Istactic with Atactic Plystyrene, Plymer, 2007, 48(21), K. Nakane, T. Yamashita, K. Iwakura, and F. Suzuki, Prperties and Structure f Ply(vinyl alchl)/silica Cmpsites, J Appl Plym Sci, 1999, 74(1), K. H. Hng and G. Sun, Phtcatalytic Functinal Cttn Fabrics Cntaining Benzphenne Chrmphric Grups, J Appl Plym Sci, 2007, 106, w œwz, 48«1y 2011

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