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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.


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(A) 1H NMR of TBAMS; (B) 13C NMR of TBAMS.
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ijms-16-20050-f005: (A) 1H NMR of TBAMS; (B) 13C NMR of TBAMS.

Mentions: The general procedure for the synthesis of the alkylaminomethylstyrenes was optimized for higher yields employing a 3-fold excess of tert-butalymine and increasing the reaction temperature to 70 °C (Figure 4). Success of the reaction was confirmed by GC-MS, APCI-MS, IR and NMR. The GC-MS showed two new peaks corresponding to the meta- and para-isomers of TBAMS (57% meta, 43% para), whereas the VBC signals, resulting from the starting material, were very small (3% of the total area in GC-MS). The EI-MS of the product peaks exhibit the molecular ion at 189 m/z. The signal at 174 m/z be rationalized a methyl loss, whereas the 117 m/z can be interpreted as a 4-(ethenyl phenyl)methylium ion that was formed by the loss of the tert-butyl amine moiety from the parent ion. The mass peak at 57 m/z corresponds to the tert-butyl group. The infrared spectrum showed at 3306 cm−1 a weak band that can be addressed as the ν(NH) vibration. In the APCI+ mass spectrum the protonated pseudo molecular ion at m/z 190 [M + H]+ was observed. The major fragments are at m/z 174 represents the (M-CH4)+, m/z 132 the (M-tert-butyl)+ (only observed after collision fragmentation of the isolated m/z 190) and m/z 117 for the loss of tert-butylamin. The structure was further confirmed by 1H and 13C NMR (Figure 5).


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)

(A) 1H NMR of TBAMS; (B) 13C NMR of TBAMS.
© Copyright Policy
Related In: Results  -  Collection

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

ijms-16-20050-f005: (A) 1H NMR of TBAMS; (B) 13C NMR of TBAMS.
Mentions: The general procedure for the synthesis of the alkylaminomethylstyrenes was optimized for higher yields employing a 3-fold excess of tert-butalymine and increasing the reaction temperature to 70 °C (Figure 4). Success of the reaction was confirmed by GC-MS, APCI-MS, IR and NMR. The GC-MS showed two new peaks corresponding to the meta- and para-isomers of TBAMS (57% meta, 43% para), whereas the VBC signals, resulting from the starting material, were very small (3% of the total area in GC-MS). The EI-MS of the product peaks exhibit the molecular ion at 189 m/z. The signal at 174 m/z be rationalized a methyl loss, whereas the 117 m/z can be interpreted as a 4-(ethenyl phenyl)methylium ion that was formed by the loss of the tert-butyl amine moiety from the parent ion. The mass peak at 57 m/z corresponds to the tert-butyl group. The infrared spectrum showed at 3306 cm−1 a weak band that can be addressed as the ν(NH) vibration. In the APCI+ mass spectrum the protonated pseudo molecular ion at m/z 190 [M + H]+ was observed. The major fragments are at m/z 174 represents the (M-CH4)+, m/z 132 the (M-tert-butyl)+ (only observed after collision fragmentation of the isolated m/z 190) and m/z 117 for the loss of tert-butylamin. The structure was further confirmed by 1H and 13C NMR (Figure 5).

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