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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

Structures of the alkylaminomethylstyrenes used for screening purpose.
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ijms-16-20050-f003: Structures of the alkylaminomethylstyrenes used for screening purpose.

Mentions: In order to screen a wider variety of different polymers for their glass transition temperatures, a series of aminomethylstyrenes was synthetized using a mixture of meta- and para-Isomers of vinylbenzyl chloride (VBC) and primary amines as starting materials (Figure 2). The reaction proceeds via an SN2 mechanism. In order to eliminate salt formation of the secondary amine an excess of sodium hydroxide (NaOH) was used. For a high conversion and short reaction times a twofold excess of amine was applied. The reaction can be carried out under mild conditions due to the high reactivity of the benzyl chloride moiety. Success of the reaction was confirmed by GC-MS and Infrared spectroscopy (IR). The yields were moderate to good (65%–80%), depending on the amine used. The structures of the alkylaminomethylstyrenes are displayed in Figure 3.


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)

Structures of the alkylaminomethylstyrenes used for screening purpose.
© Copyright Policy
Related In: Results  -  Collection

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

ijms-16-20050-f003: Structures of the alkylaminomethylstyrenes used for screening purpose.
Mentions: In order to screen a wider variety of different polymers for their glass transition temperatures, a series of aminomethylstyrenes was synthetized using a mixture of meta- and para-Isomers of vinylbenzyl chloride (VBC) and primary amines as starting materials (Figure 2). The reaction proceeds via an SN2 mechanism. In order to eliminate salt formation of the secondary amine an excess of sodium hydroxide (NaOH) was used. For a high conversion and short reaction times a twofold excess of amine was applied. The reaction can be carried out under mild conditions due to the high reactivity of the benzyl chloride moiety. Success of the reaction was confirmed by GC-MS and Infrared spectroscopy (IR). The yields were moderate to good (65%–80%), depending on the amine used. The structures of the alkylaminomethylstyrenes are displayed in Figure 3.

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