Clickable antimicrobial molecules and polymers
Inventors
Liu, Chao • Hu, Jianqing • Peng, Kaimei • Ding, Wei
Assignees
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Publication Number
US-10709130-B2
Publication Date
2020-07-14
Expiration Date
Abstract
In one aspect, the present disclosure relates to click-functional antimicrobial molecules (including small molecules or, in some cases, macromolecules) and the construction of antimicrobial polymers such as polyurethanes, polyesters, and polyacrylates, including through the use of such molecules. In some cases, the antimicrobial click-functional molecules are based on 1,2-benzisothiazolin-3-one (BIT), trimethylguanidine or tetramethylguanidine (TMG), polyhexamethylene guanidine (PHMG), fluorine-containing molecules, or a combination thereof. For example, 1,2-benzisothiazolin-3-one (BIT) functionalized with an alkyne (BIT-Al), trimethylguanidine or tetramethylguanidine (TMG) functioned with an alkyne (TMG-Al) or dual alkynes (TMG-dAl), and/or polyhexamethylene guanidine (PHMG) functionalized with an alkyne (PHMG-Al) are described herein. Clickable antimicrobial polymers can be used to form coatings or films.
Core Innovation
The invention relates to click-functional antimicrobial molecules and antimicrobial polymers formed by integrating antimicrobial moieties into polymer backbones and/or side chains via click chemistry. Structural components are defined by Formula (I), Formula (II), Formula (II-1), and Formula (III), where azide-functional antimicrobial groups and/or quaternary ammonium elements are incorporated into the polymer or oligomer structure. The resulting polymer or oligomer includes quaternary ammonium moiety within the backbone and is antimicrobial.
A first antimicrobial moiety or a first dehydrogenated antimicrobial moiety is used as part of a compound having the structure of Formula (I). One or more second monomers react with the compound of Formula (I) to form a polymer or oligomer, and the formed polymer or oligomer is further reacted with a compound having the structure of Formula (II) such that a leaving group of the second antimicrobial moiety is replaced with the azido group of Formula (II). This azido-functional element is incorporated to enable click-functional antimicrobial polymer formation.
The polymer or oligomer may be defined according to Formula (III), including a polymer or oligomer structure that incorporates quaternary ammonium moiety within the backbone. The disclosed antimicrobial polymers are formed as polyurethane and other polymer classes through reaction product formation and incorporation of clickable monomers, and the document describes antimicrobial performance trends associated with the resulting compositions.
Claims Coverage
The document provides two independent claims: a composition claim and a method-of-making claim. Across these independent claims, the coverage centers on forming an antimicrobial polymer or oligomer from a Formula (I)-based reaction product and then reacting it with a Formula (II) compound having azido-functional antimicrobial functionality, yielding a polymer or oligomer containing quaternary ammonium moieties in the backbone.
Antimicrobial polymer or oligomer with quaternary ammonium backbone and azido-functional antimicrobial incorporation
A composition comprising a polymer or oligomer formed from a reaction product of a compound having the structure of Formula (I) wherein R1 comprises a first antimicrobial moiety or a first dehydrogenated antimicrobial moiety, and one or more second monomers that react with the compound of (i) to form the polymer or oligomer; and a reaction product of the formed polymer or oligomer with a compound having the structure of Formula (II) where R2 comprises a second antimicrobial moiety in which a leaving group of the second antimicrobial moiety has been replaced with the azido group of the structure of Formula (II), wherein the resulting polymer or oligomer comprises a quaternary ammonium moiety within the backbone and is antimicrobial.
Method of making an antimicrobial composition via Formula (I) polymer or oligomer formation and Formula (II) azido-functional substitution
A method of making an antimicrobial composition comprising reacting a compound having the structure of Formula (I) wherein R1 comprises an antimicrobial moiety or a dehydrogenated antimicrobial moiety with one or more second monomers that react with the compound of (i) to form a polymer or oligomer, and reacting the formed polymer or oligomer with a compound having the structure of Formula (II) where R2 comprises an antimicrobial moiety in which a leaving group of the second antimicrobial moiety has been replaced with the azido group of the structure of Formula (II), wherein the resulting polymer or oligomer comprises a quaternary ammonium moiety within the backbone and is antimicrobial.
Collectively, the independent claims cover an antimicrobial composition where a Formula (I)-derived polymer or oligomer is further reacted with a Formula (II) azido-functional antimicrobial compound to yield quaternary ammonium moiety within the backbone, and a corresponding method of making the antimicrobial composition using the same Formula (I) polymer or oligomer formation followed by the Formula (II) reaction.
Stated Advantages
Antimicrobial functionality of the resulting polymer or oligomer.
Documented Applications
The polymer or oligomer forms an antimicrobial coating on a surface.
A method that reduces microbial proliferation on a surface by disposing the composition on a surface.
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