Antimicrobial compound
Inventors
Preda, Dorin V. • Rathmell, Aaron R. • Hessel, Colin M. • Lennhoff, John D. • Antalek, Mitchell T.
Assignees
Publication Number
US-10806140-B2
Publication Date
2020-10-20
Expiration Date
2039-04-04
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Abstract
An antimicrobial composition including low molecular weight dendrimers of formula (1):Q is an antimicrobial moiety in monomer or dendritic form, N is a nitrogen atom, L2 is a linker linking each Y1 molecular spacer to the nitrogen atom, Y1 is a molecular spacer spacing each antimicrobial moiety Q from the L2 linker, there are two or more chains of antimicrobial moieties and molecular spacers, X is a linker configured to covalently bond to surface functionalities of the substrate, and Y2 is a molecular spacer between the linker X and the nitrogen atom.
Core Innovation
The invention provides an antimicrobial composition comprising low molecular weight dendrimers of a specific formula designed to impart antimicrobial properties to various substrates. These dendrimers feature antimicrobial moieties, such as positively charged quaternary ammonium cations, linked via molecular spacers and covalently attached to surface functionalities of substrates through specific linkers. The molecular architecture allows for two or more chains of antimicrobial moieties and spacers, which can be tailored depending on the substrate and desired application.
The problem addressed by this invention is the inadequacy of existing antimicrobial surfaces, which often exhibit low antimicrobial activity and/or suffer from the loss of antimicrobial efficacy due to leaching or laundering. Current technologies do not reliably provide surfaces with both strong, durable antimicrobial effects and resistance to the removal of active agents through washing or use.
This innovation solves the problem by employing novel quaternary ammonium cation dendrimers that are covalently bound to surfaces such as textiles, metals, and polymers, resulting in enhanced and broad-spectrum antimicrobial activity. The covalent attachment ensures the antimicrobial activity remains robust even after exposure to heat or laundering. The approach has demonstrated effectiveness for textile, metal, and polymer surfaces, with the possibility to adapt the attachment chemistry for other types of materials.
Claims Coverage
There are multiple independent claims defining the main inventive features of the patent.
Antimicrobial composition using low molecular weight dendrimers of formula (1)
The invention provides a composition that imparts antimicrobial properties to a substrate. The primary feature is the use of low molecular weight dendrimers of formula (1), comprising: - An antimicrobial moiety (Q) in monomer or dendritic form. - A nitrogen atom (N). - A linker (L2) linking each molecular spacer (Y1) to the nitrogen atom. - Two or more chains of antimicrobial moieties and molecular spacers. - A linker (X) configured to covalently bond to surface functionalities of the substrate. - A molecular spacer (Y2) between the linker X and the nitrogen atom, which may include a ring structure such as a benzene ring.
Composition including a defined antimicrobial moiety, linkers, and spacers for covalent surface attachment
This inventive feature includes compositions where: - The antimicrobial moiety can be in monomer or dendritic form and includes positively charged quaternary ammonium cations as specified (for example, tetrasubstituted +NR1R2R3R4 or trisubstituted Z1Z2N+═CA1A2). - There are two or more chains of antimicrobial moieties and molecular spacers. - Linker X is configured to covalently bond to the surface, selected from amino groups, dichlorotriazine, phosphonic acid, azide, or others. - Linker L2 may be a substituted N-propyl-propionamide; Y1 may include substituted N-ethylurea. - Y2 is a molecular spacer such as a ring structure. - The composition covers the detailed molecular arrangement and surface binding.
Variants of compositions defined by antimicrobially functionalized dendrimers
Several claims independently define variants of the antimicrobial composition, specifically reciting: - The use of particular quaternary ammonium cation species such as substituted dimethyldodecylammonium cation, didodecylmethylammonium cation, dimethyloctylammonium cation, and substituted 2-methyl-1-decylimidazolium. - Molecular arrangements involving specific linker and spacer chemistries to enable optimal covalent attachment and antimicrobial performance. - Claims further define that the antimicrobial dendrimers can have a benzene ring structure within the molecular spacer Y2.
In summary, the claims cover antimicrobial compositions using low molecular weight dendrimers with specific branching, spacer, and linker chemistries, designed for durable covalent attachment to diverse substrates and comprising defined quaternary ammonium cation antimicrobial moieties.
Stated Advantages
Provides high efficacy and broad-spectrum antimicrobial activity, including antibacterial (both vegetative cells and spores), antifungal, and antiviral activity.
Ensures resistance to leaching and laundering by covalent attachment of dendrimers to surfaces, maintaining antimicrobial properties even after washing or heat exposure.
Demonstrates robust performance and durability of antimicrobial finish on various surfaces including textiles, metals, and polymers.
Exhibits biocompatibility as fabrics derivatized with these dendrimers are non-cytotoxic and do not cause skin irritation as determined by standard tests.
Allows for scalable processing and the potential for semi-continuous or batch processing in large-scale applications.
Documented Applications
Functionalization of textile surfaces to produce antimicrobial fabrics that maintain activity after laundering and heat exposure.
Antimicrobial treatment of metallic surfaces, including aluminum and stainless steel, resulting in high efficacy against bacteria and spores.
Modification of polymeric materials such as polyurethane, including potential use on medical devices like tracheal tubes and catheters, to impart antimicrobial properties.
Application to filtration media and potentially to endotracheal tube materials to provide antimicrobial characteristics.
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