Skip to main content
Disciplines
Automotive Business IT + Informatics Construction + Real Estate Electrical Engineering + Electronics Energy + Sustainability Insurance + Risk Finance + Banking Management + Leadership Marketing + Sales Mechanical Engineering + Materials
Events
DE
EN
Books
Journals
Topic Page
Marketing
Start single access now
Access for companies
EXTENDED SEARCH
Log in
Top
Polymer Bulletin
Published in: Polymer Bulletin 9/2017

30-01-2017 | Original Paper

Effect of the ionized carboxyl group on the water compatibility and the antifungal activity of the benzimidazole-grafted polyurethane

Authors: Yong-Chan Chung, Ha Youn Kim, Jae Won Choi, Byoung Chul Chun

Published in: Polymer Bulletin | Issue 9/2017

Log in

Activate our intelligent search to find suitable subject content or patents.

search-config
loading …

Abstract

Two series of polyurethane (PU) containing 2,2-bis(hydroxymethyl)propanoic acid (DMPA) and the grafted benzimidazole (BI) were prepared to compare their antifungal activities. The DMPA carboxyl group of BN series was completely ionized using a strong base (NaOH) and the DMPA carboxyl group of BT series was partly ionized by a weak base (trimethylamine). The BN series exhibited a faster decrease in maximum tensile strength and strain at break compared to the BT series. The fully ionized DMPA carboxyl group of BN series severely affected the thermal and mechanical properties. Finally, the BN series demonstrated a complete suppression of fungal growth (Chaetomium globosum) whereas unmodified PU and the BT series could not fully suppress the growth of fungi at the same BI content. Therefore, the complete ionization of DMPA carboxyl group played an important role in the antifungal activity.
previous article Dielectric properties of three-phase PS-BiFeO3-GNP nanocomposites
next article Effect of amine-functionalized silica nanoparticles on thermal and mechanical behaviors of DGEBA/IPD epoxy networks

Dont have a licence yet? Then find out more about our products and how to get one now:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

  • über 102.000 Bücher
  • über 537 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Finance + Banking
  • Management + Führung
  • Marketing + Vertrieb
  • Maschinenbau + Werkstoffe
  • Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

inform now

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

  • über 67.000 Bücher
  • über 390 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Maschinenbau + Werkstoffe




 

Jetzt Wissensvorsprung sichern!

inform now
Literature
1.
Spontak RJ, Patel NP (2000) Thermoplastic elastomers: fundamentals and applications. Curr Opin Colloid Interface 5:333–340CrossRef
2.
Chen LW, Lin JR (1998) Study on shape-memory behavior of polyether-based polyurethanes. II. Influence of soft-segment molecular weight. J Appl Polym Sci 69:1575–1586CrossRef
3.
Petrović ZS, Ferguson J (1991) Polyurethane elastomers. Prog Polym Sci 16:695–836CrossRef
4.
Chung YC, Park HS, Choi JW, Chun BC (2012) Characterization and low temperature test of the flexibly crosslinked polyurethane copolymer by poly(dimethylsiloxane). High Perform Polym 24:200–209CrossRef
5.
Chung YC, Jung IH, Choi JW, Chun BC (2014) Characterization and proof testing of the halochromic shape memory polyurethane. Polym Bull 71:1153–1171CrossRef
6.
Chung YC, Choi JW, Lee SH, Chun BC (2011) Investigation of fluorescent shape memory polyurethane grafted with various dyes. Bull Korean Chem Soc 32:2988–2996CrossRef
7.
Tischer M, Pradel G, Ohlsen K, Holzgrabe U (2012) Quaternary ammonium salts and their antimicrobial potential: targets or nonspecific interactions. Chem Med Chem 7:22–31CrossRef
8.
Kenawy ER, Abdel-Hay FI, El-Magd AA, Mahmoud Y (2006) Biologically active polymers: VII. Synthesis and antimicrobial activity of some crosslinked copolymers with quaternary ammonium and phosphonium groups. React Funct Polym 66:419–429CrossRef
9.
Rogalskyy S, Bardeau JF, Tarasyuk O, Fatyeyeva K (2012) Fabrication of new antifungal polyamide-12 material. Polym Int 61:686–691CrossRef
10.
Vlad S, Tanase C, Macocinschi D, Ciobanu C, Balaes T, Filip D, Gostin IN, Gradinaru LM (2012) Antifungal behavior of polyurethane membrane with zinc oxide nanoparticles. Dig J Nanomater Biosci 7:51–58
11.
Meng N, Zhou NL, Zhang SQ, Shen J (2009) Synthesis and antifungal activities of polymer/montmorillonite–terbinafine hydrochloride nanocomposite films. Appl Clay Sci 46:136–140CrossRef
12.
Paladini F, Cooper IR, Pollini M (2014) Development of antibacterial and antifungal silver-coated polyurethane foams as air filtration units for the prevention of respiratory diseases. J Appl Microbiol 116:710–717CrossRef
13.
Napoli M, Saturnino C, Cianciulli EI, Varcamonti M, Zanfardino A, Tommonaro G, Longo P (2013) Silver(I) N-heterocyclic carbene complexes: synthesis, characterization and antibacterial activity. J Organomet Chem 725:46–53CrossRef
14.
Patel RV, Patel PK, Kumari P, Rajani DP, Chikhalia KH (2012) Synthesis of benzimidazolyl-1,3,4-oxadiazol-2ylthio-N-phenyl (benzothiazolyl) acetamides as antibacterial, antifungal and antituberculosis agents. Eur J Med Chem 53:41–51CrossRef
15.
Ansari KF, Lal C (2009) Synthesis, physicochemical properties and antimicrobial activity of some new benzimidazole derivatives. Eur J Med Chem 44:4028–4033CrossRef
16.
Sheehan DJ, Hitchcock CA, Sibley CM (1999) Current and emerging azole antifungal agents. Clin Microbiol Rev 12:40–79
17.
Song S, Kim J, Shim JY, Kim G, Lee BH, Jin Y, Park SH, Kim I, Lee K, Suh H (2012) Synthesis and characterization of dimethyl-benzimidazole based low bandgap copolymers for OPVs. Synth Met 162:988–994CrossRef
18.
Song S, Park SH, Jin Y, Kim I, Lee K, Suh H (2012) Conjugated copolymers based on dihexyl-benzimidazole moiety for organic photovoltaics. Polymer 51:5385–5391CrossRef
19.
Choi H, Chung IS, Hong K, Park CE, Kim SY (2008) Soluble polyimides from unsymmetrical diamine containing benzimidazole ring and trifluoromethyl pendent group. Polymer 49:2644–2649CrossRef
20.
Linlin M, Mishra AK, Kim NH, Lee JH (2012) Poly(2,5-benzimidazole)–silica nanocomposite membranes for high temperature proton exchange membrane fuel cell. J Membr Sci 411:91–98CrossRef
21.
Kim SK, Kim KH, Park JO, Kim K, Ko T, Choi SW, Pak C, Chang H, Lee JC (2013) Highly durable polymer electrolyte membranes at elevated temperature: cross-linked copolymer structure consisting of poly(benzoxazine) and poly(benzimidazole). J Power Sour 226:346–353CrossRef
22.
Petrovic ZS, Javni I, Divjakovic VJ (1998) Structure and physical properties of segmented polyurethane elastomers containing chemical crosslinks in the hard segment. J Polym Sci Pol Phys 36:221–235CrossRef
23.
Sekkar V, Gopalakrishnan S, Devi KA (2003) Studies on allophanate–urethane networks based on hydroxyl terminated polybutadiene: effect of isocyanate type on the network characteristics. Eur Polym J 39:1281–1290CrossRef
24.
Sekkar V, Rama Rao M, Krishinamurthy VN, Jane SR (1996) Modeling of polyurethane networks based on hydroxy-terminated polybutadiene and poly(12-hydroxy stearic acid–co–TMP) ester polyol: correlation of network parameters with mechanical properties. J Appl Polym Sci 62:2317–2327CrossRef
25.
Freij-Larsson C, Wesslen B (1993) Grafting of polyurethane surfaces with poly(ethylene glycol). J Appl Polym Sci 50:345–352CrossRef
26.
Archambault JG, John L (2004) Protein resistant polyurethane surfaces by chemical grafting of PEO: amino-terminated PEO as grafting reagent. Colloid Surface B 39:9–16CrossRef
27.
Tan K, Obendorf SK (2006) Surface modification of microporous polyurethane membrane with poly(ethylene glycol) to develop a novel membrane. J Mem Sci 274:150–158CrossRef
28.
Alves P, Coelho JFJ, Haack J, Rota A, Bruinink A, Gil MH (2009) Surface modification and characterization of thermoplastic polyurethane. Eur Polym J 45:1412–1419CrossRef
29.
Huang J, Xu W (2010) Zwitterionic monomer graft copolymerization onto polyurethane surface through a PEG spacer. Appl Surf Sci 256:3921–3927CrossRef
30.
Chung YC, Kim HY, Choi JW, Chun BC (2015) Preparation of water-compatible antifungal polyurethane with grafted benzimidazole as the antifungal agent. J Appl Polym Sci 132:41676–41684CrossRef
31.
Chung YC, Choi JW, Chung HM, Chun BC (2012) The MDI-mediated lateral crosslinking of polyurethane copolymer and the impact on tensile properties and shape memory effect. Bull Korean Chem Soc 33:692–694CrossRef
32.
Choi T, Weksler J, Padsalgikar A, Runt J (2010) Microstructural organization of polydimethylsiloxane soft segment polyurethanes derived from a single macrodiol. Polymer 51:4375–4382CrossRef
33.
Russo P, Lavorgna M, Piscitelli F, Acierno D, Di Maio L (2013) Thermoplastic polyurethane films reinforced with carbon nanotubes: the effect of processing on the structure and mechanical properties. Eur Polym J 49:379–388CrossRef
34.
Chung YC, Kim HY, Yu JH, Chun BC (2015) Impact of cholesterol grafting on molecular interactions and low temperature flexibility of polyurethanes. Macromol Res 23:350–359CrossRef
35.
Chung YC, Lee BH, Jo SH, Chun BC (2015) Preparation and characterization of polyurethane copolymer grafted with polystyrene side chains. Polym Plast Technol 54:1066–1076CrossRef
Metadata
Title
Effect of the ionized carboxyl group on the water compatibility and the antifungal activity of the benzimidazole-grafted polyurethane
Authors
Yong-Chan Chung
Ha Youn Kim
Jae Won Choi
Byoung Chul Chun
Publication date
30-01-2017
Publisher
Springer Berlin Heidelberg
Published in
Polymer Bulletin / Issue 9/2017
Print ISSN: 0170-0839
Electronic ISSN: 1436-2449
DOI
https://doi.org/10.1007/s00289-017-1916-3

Other articles of this Issue 9/2017

Polymer Bulletin 9/2017 Go to the issue

Original Paper

Epoxidation of eucommia ulmoides gum by emulsion process and the performance of its vulcanizates

Original Paper

Synthesis and application of fluorinated α-diimine nickel catalyst for ethylene polymerization: deactivation mechanism

Original Paper

The synthesis and adsorption performance of polyamine Cu2+ imprinted polymer for selective removal of Cu2+

Original Paper

Thermal decomposition reaction of pinacolone diperoxide: its use as radical initiator in the styrene polymerization

Original Paper

Synthesis of gold nanoparticles using poly(ethyleneglycol)-b-poly(N,N-diethylaminoethylmethacrylate) as nanoreactors

Original Paper

Synthesis and characterization of new shellac–hydroxypropylmethylcellulose composite for pharmaceutical applications

Premium Partners

    Image Credits