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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) ethyl methacrylate (TBAEMA) and its resulting polymer poly-[2-(tert-butylamino) ethyl methacrylate] (poly(TBAEMA)).
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ijms-16-20050-f001: Structure of 2-(tert-butylamino) ethyl methacrylate (TBAEMA) and its resulting polymer poly-[2-(tert-butylamino) ethyl methacrylate] (poly(TBAEMA)).

Mentions: Poly[2-(tert-butylamino)ethyl methacrylate] (poly(TBAEMA)) is a typical representative of a water-insoluble biocide, its structure is displayed in Figure 1. It was developed in 2001 by Creavis Technologies and Innovation of the Degussa (Marl, Germany). This polymer class was referred as sustainable active microbicidal (SAM-Polymers®, Marl, Germany). According to the patent literature, poly(TBAEMA) exhibits inherent biocidal properties and has shown potential application in antifouling paints and coatings [24,25,26,27] or denture base acrylic resins [28,29]. The antimicrobial activity is caused by the pendant bulky secondary amine of the methacrylate backbone, without the need for quaternization, as is the case for other amine-containing polymers [30]. It must be noted that, although poly(TBAEMA) has high antimicrobial activity and low toxicity, the parent monomer shows no antimicrobial effect even at higher concentrations. This finding suggests that the antimicrobial action is closely related to the molecular structure and conformation of the polymer chains [30]. It has been reported that the solubility of poly(TBAEMA) in water (at pH = 7) is lower than 3.0 mg/L. This renders the biocide especially useful for construction materials designed to be in contact with water, since a very low leachability of poly(TBAEMA) from polymer blends and compounds can be expected [31]. A major drawback of poly(TBAEMA) is the low glass transition temperature (TG) of 40 °C which limits the application as the surface becomes sticky at elevated temperatures. Other weak points are: high water uptake and a tendency for hydrolysis which yields 2-tert-butylamino-ethanol. The aim of this study was the development of a new monomer for this class of SAM®-polymers, especially raising the TG reducing water uptake and avoiding hydrolysis [32].


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) ethyl methacrylate (TBAEMA) and its resulting polymer poly-[2-(tert-butylamino) ethyl methacrylate] (poly(TBAEMA)).
© Copyright Policy
Related In: Results  -  Collection

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

ijms-16-20050-f001: Structure of 2-(tert-butylamino) ethyl methacrylate (TBAEMA) and its resulting polymer poly-[2-(tert-butylamino) ethyl methacrylate] (poly(TBAEMA)).
Mentions: Poly[2-(tert-butylamino)ethyl methacrylate] (poly(TBAEMA)) is a typical representative of a water-insoluble biocide, its structure is displayed in Figure 1. It was developed in 2001 by Creavis Technologies and Innovation of the Degussa (Marl, Germany). This polymer class was referred as sustainable active microbicidal (SAM-Polymers®, Marl, Germany). According to the patent literature, poly(TBAEMA) exhibits inherent biocidal properties and has shown potential application in antifouling paints and coatings [24,25,26,27] or denture base acrylic resins [28,29]. The antimicrobial activity is caused by the pendant bulky secondary amine of the methacrylate backbone, without the need for quaternization, as is the case for other amine-containing polymers [30]. It must be noted that, although poly(TBAEMA) has high antimicrobial activity and low toxicity, the parent monomer shows no antimicrobial effect even at higher concentrations. This finding suggests that the antimicrobial action is closely related to the molecular structure and conformation of the polymer chains [30]. It has been reported that the solubility of poly(TBAEMA) in water (at pH = 7) is lower than 3.0 mg/L. This renders the biocide especially useful for construction materials designed to be in contact with water, since a very low leachability of poly(TBAEMA) from polymer blends and compounds can be expected [31]. A major drawback of poly(TBAEMA) is the low glass transition temperature (TG) of 40 °C which limits the application as the surface becomes sticky at elevated temperatures. Other weak points are: high water uptake and a tendency for hydrolysis which yields 2-tert-butylamino-ethanol. The aim of this study was the development of a new monomer for this class of SAM®-polymers, especially raising the TG reducing water uptake and avoiding hydrolysis [32].

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