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Development of a New Monomer for the Synthesis of Intrinsic Antimicrobial Polymers with Enhanced Material Properties.

Brodkorb F, Fischer B, Kalbfleisch K, Robers O, Braun C, Dohlen S, Kreyenschmidt J, Lorenz R, Kreyenschmidt M - Int J Mol Sci (2015)

Bottom Line: The use of biocidal compounds in polymers is steadily increasing because it is one solution to the need for safety and hygiene.The biocidal action results from contact of the polymer to the microorganisms, with no release of active molecules.The antimicrobial activity was analyzed by the test method JIS Z 2801:2000.

View Article: PubMed Central - PubMed

Affiliation: Institute of Construction and Functional Materials, University of Applied Sciences Münster, Stegerwaldstraße 39, 48565 Steinfurt, Germany. f.brodkorb@fh-muenster.de.

ABSTRACT
The use of biocidal compounds in polymers is steadily increasing because it is one solution to the need for safety and hygiene. It is possible to incorporate an antimicrobial moiety to a polymer. These polymers are referred to as intrinsic antimicrobial. The biocidal action results from contact of the polymer to the microorganisms, with no release of active molecules. This is particularly important in critical fields like food technology, medicine and ventilation technology, where migration or leaching is crucial and undesirable. The isomers N-(1,1-dimethylethyl)-4-ethenyl-benzenamine and N-(1,1-dimethyl-ethyl)-3-ethenyl-benzenamine (TBAMS) are novel (Co-)Monomers for intrinsic anti-microbial polymers. The secondary amines were prepared and polymerized to the corresponding water insoluble polymer. The antimicrobial activity was analyzed by the test method JIS Z 2801:2000. Investigations revealed a high antimicrobial activity against Staphylococcus aureus and Escherichia coli with a reduction level of >4.5 log10 units. Furthermore, scanning electron microscopy (SEM) of E. coli. in contact with the polymer indicates a bactericidal action which is caused by disruption of the bacteria cell membranes, leading to lysis of the cells.

No MeSH data available.


Related in: MedlinePlus

Structure of 2-(tert-butylamino) methylstyrene (TBAMS) and its resulting polymer.
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ijms-16-20050-f006: Structure of 2-(tert-butylamino) methylstyrene (TBAMS) and its resulting polymer.

Mentions: Success of the polymerization was confirmed by 1H and 13C NMR (Figure 7). First experiments to polymerize TBAMS in bulk resulted in small molecular weight polymers. Therefore it was necessary to increase the molecular weight to an acceptable level for technical application. Accordingly polymerization of TBAMS was carried out in ethanol using 2,2′-azobisisobutyronitrile (AIBN) as initiator(Figure 6). The molecular weight (Mw) was raised to about 185 kDa in typical experiments. The polydispersity (MW/Mn) of 5.2 is rather high. A pronounced polydispersity (2.5–3) is typical for AIBN initiated radical reactions. The high polydispersity observed in the poly(TBAMS) polymer can be an indication, that grafting occurs during polymerization. Probably chain transfer occurs at the benzylic position of poly(TBAMS) and TBAMS. Poly(TBAMS) possesses a TG of about 68 °C, which is considerably higher than the TG of poly(TBAEMA). The poly(TBAMS) was soluble in ethanol and formed uniform, colorless and transparent films upon solvent evaporation. Glass transition temperatures can be further be adjusted by copolymerization to about 160 °C without the loss of the antimicrobial activity. The copolymer was synthetized using 42 mol % TBAMS, 42 mol % 4-vinylpyridine and 16 mol % 4-vinylbenzoic acid. The log reduction of this copolymer was 3.5 for S. aureus.


Development of a New Monomer for the Synthesis of Intrinsic Antimicrobial Polymers with Enhanced Material Properties.

Brodkorb F, Fischer B, Kalbfleisch K, Robers O, Braun C, Dohlen S, Kreyenschmidt J, Lorenz R, Kreyenschmidt M - Int J Mol Sci (2015)

Structure of 2-(tert-butylamino) methylstyrene (TBAMS) and its resulting polymer.
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4581340&req=5

ijms-16-20050-f006: Structure of 2-(tert-butylamino) methylstyrene (TBAMS) and its resulting polymer.
Mentions: Success of the polymerization was confirmed by 1H and 13C NMR (Figure 7). First experiments to polymerize TBAMS in bulk resulted in small molecular weight polymers. Therefore it was necessary to increase the molecular weight to an acceptable level for technical application. Accordingly polymerization of TBAMS was carried out in ethanol using 2,2′-azobisisobutyronitrile (AIBN) as initiator(Figure 6). The molecular weight (Mw) was raised to about 185 kDa in typical experiments. The polydispersity (MW/Mn) of 5.2 is rather high. A pronounced polydispersity (2.5–3) is typical for AIBN initiated radical reactions. The high polydispersity observed in the poly(TBAMS) polymer can be an indication, that grafting occurs during polymerization. Probably chain transfer occurs at the benzylic position of poly(TBAMS) and TBAMS. Poly(TBAMS) possesses a TG of about 68 °C, which is considerably higher than the TG of poly(TBAEMA). The poly(TBAMS) was soluble in ethanol and formed uniform, colorless and transparent films upon solvent evaporation. Glass transition temperatures can be further be adjusted by copolymerization to about 160 °C without the loss of the antimicrobial activity. The copolymer was synthetized using 42 mol % TBAMS, 42 mol % 4-vinylpyridine and 16 mol % 4-vinylbenzoic acid. The log reduction of this copolymer was 3.5 for S. aureus.

Bottom Line: The use of biocidal compounds in polymers is steadily increasing because it is one solution to the need for safety and hygiene.The biocidal action results from contact of the polymer to the microorganisms, with no release of active molecules.The antimicrobial activity was analyzed by the test method JIS Z 2801:2000.

View Article: PubMed Central - PubMed

Affiliation: Institute of Construction and Functional Materials, University of Applied Sciences Münster, Stegerwaldstraße 39, 48565 Steinfurt, Germany. f.brodkorb@fh-muenster.de.

ABSTRACT
The use of biocidal compounds in polymers is steadily increasing because it is one solution to the need for safety and hygiene. It is possible to incorporate an antimicrobial moiety to a polymer. These polymers are referred to as intrinsic antimicrobial. The biocidal action results from contact of the polymer to the microorganisms, with no release of active molecules. This is particularly important in critical fields like food technology, medicine and ventilation technology, where migration or leaching is crucial and undesirable. The isomers N-(1,1-dimethylethyl)-4-ethenyl-benzenamine and N-(1,1-dimethyl-ethyl)-3-ethenyl-benzenamine (TBAMS) are novel (Co-)Monomers for intrinsic anti-microbial polymers. The secondary amines were prepared and polymerized to the corresponding water insoluble polymer. The antimicrobial activity was analyzed by the test method JIS Z 2801:2000. Investigations revealed a high antimicrobial activity against Staphylococcus aureus and Escherichia coli with a reduction level of >4.5 log10 units. Furthermore, scanning electron microscopy (SEM) of E. coli. in contact with the polymer indicates a bactericidal action which is caused by disruption of the bacteria cell membranes, leading to lysis of the cells.

No MeSH data available.


Related in: MedlinePlus