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US 2017/0303541 A1Published application
Antimicrobial guanidinium and thiouronium functionalized polymers
AssigneesInternational Business Machines Corporation, Agency for Science, Technology and Research
InventorsWilly Chin, James L. Hedrick, Ashlynn L. Z. Lee, Robert J. Ono, Yi Yan Yang
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Abstract
Antimicrobial cationic polycarbonates and polyurethanes have been prepared comprising one or more pendent guanidinium and/or isothiouronium groups. Additionally, antimicrobial particles were prepared having a silica core linked to surface groups comprising a guanidinium and/or isothiouronium group. The cationic polymers and cationic particles can be potent antimicrobial agents against Gram-negative microbes, Gram-positive microbes, and/or fungi.
Claims20
A method, comprising:
- forming an initial polymer by organocatalyzed ring opening polymerization of a cyclic carbonate monomer of formula (M-1):
- wherein
- ring atoms of (M-1) are numbered 1 to 6,
- each B′ is an independent acid-labile protecting group,
- L′ is a divalent hydrocarbon radical comprising 2 to 30 carbons,
- each R′ is an independent monovalent radical selected from the group consisting of hydrogen and alkyl groups comprising 1 to 6 carbons,
- R″ is a monovalent radical selected from the group consisting of hydrogen and alkyl groups comprising 1 to 6 carbons, and
- Y′ is *—O—* or *—N(H)—*;
- and
- treating the initial polymer with a protic acid, thereby forming a cationic polymer, the cationic polymer comprising a cationic subunit of formula (A-1):
- wherein
- atoms numbered 1, 2, 3, 4, 5, and 6 of (A-1) are backbone atoms of the cationic polymer,
- m is 1 or 2,
- n is 0 or 1, wherein when m is 2, n is 0,
- each R′ is an independent monovalent radical selected from the group consisting of hydrogen and alkyl groups comprising 1 to 6 carbons,
- R″ is a monovalent radical selected from the group consisting of hydrogen and alkyl groups comprising 1 to 6 carbons, and
- each Q″ is an independent group comprising a guanidinium group.
14 more elements
A method, comprising:
- forming an initial polymer by organocatalyzed ring opening polymerization of a cyclic carbonate monomer of formula (M-6):
- wherein
- ring atoms of (M-6) are numbered 1 to 6,
- Lb is a divalent linking group comprising 1 or more carbons,
- E′ is a substituent capable of undergoing a nucleophilic substitution reaction with thiourea to form an isothiouronium group,
- each R′ is an independent monovalent radical selected from the group consisting of hydrogen and alkyl groups comprising 1 to 6 carbons, and
- R″ is a monovalent radical selected from the group consisting of hydrogen and alkyl groups comprising 1 to 6 carbons;
- and
- treating the initial polymer with thiourea, thereby forming a cationic polymer, the cationic polymer comprising a cationic subunit of formula (A-1):
- wherein
- atoms numbered 1, 2, 3, 4, 5, and 6 of (A-1) are backbone atoms of the cationic polymer,
- m is 1 or 2,
- n is 0 or 1, wherein when m is 2, n is 0,
- each R′ is an independent monovalent radical selected from the group consisting of hydrogen and alkyl groups comprising 1 to 6 carbons,
- R″ is a monovalent radical selected from the group consisting of hydrogen and alkyl groups comprising 1 to 6 carbons, and
- each Q″ is an independent group comprising a isothiouronium group.
13 more elements
Dependencies are inferred from the claim text.