Reactive antibacterial compound and preparation method thereof
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Solution Overview
Problem
Current antibacterial materials face challenges such as reduced efficacy over time, potential for drug resistance in microorganisms, toxicity, poor heat resistance, and environmental sustainability issues, particularly with organic and polymeric quaternary ammonium salts, and limitations in mass production of natural agents.
Innovation Solution
A reactive antibacterial compound with a zwitterionic structure and a terminal isocyanate group that can bind to surfaces of fibers and materials, providing durable antibacterial effects by reacting with functional groups, thereby denaturing proteins and damaging cell structures of microorganisms like E. coli and S. aureus.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If quaternary ammonium salts are used as antibacterial agents, then antibacterial effectiveness is improved, but heat resistance deteriorates and migration occurs
Solution Approach 1:
The patent combines quaternary ammonium salt antibacterial groups with polyurethane polymer backbone to create a composite material. The polymer provides thermal stability and structural integrity, while the quaternary ammonium groups provide antibacterial activity. This composite structure resolves the contradiction by integrating two materials with complementary properties.
Solution Approach 2:
The antibacterial quaternary ammonium groups are localized within the polyurethane polymer structure at specific segments rather than being distributed freely. This localized incorporation maintains antibacterial effectiveness at the molecular level while the overall polymer structure provides heat resistance and prevents migration.
2Reliability
If quaternary ammonium salts are used as antibacterial agents, then antibacterial effectiveness is improved, but chemical stability deteriorates
Solution Approach 1:
The patent creates a composite where quaternary ammonium salts are chemically bonded to a polyurethane polymer matrix. The polymer provides chemical stability and structural framework, while the quaternary ammonium groups maintain their antibacterial function. This composite approach resolves the contradiction between reactivity and stability.
3Reliability
If metal ions are used for antibacterial properties, then bacteriostasis is achieved, but drug resistance develops and effectiveness reduces over time
Solution Approach 1:
The patent changes the fundamental mechanism from metal ion release (physical/chemical process) to direct contact killing by quaternary ammonium groups (biological interaction). This parameter change in the antibacterial mechanism prevents resistance development and maintains effectiveness over time, as the quaternary ammonium groups physically disrupt bacterial cell membranes rather than relying on slow ion release.
4Speed
If quaternary ammonium salts are used as antibacterial agents, then rapid antibacterial action is achieved, but toxicity and irritation increase
Solution Approach 1:
The quaternary ammonium antibacterial groups are locally incorporated into the polyurethane polymer structure, concentrating the antibacterial function where needed while the polymer matrix distributes and moderates the overall toxicity. This local incorporation maintains rapid antibacterial action at the site of application while reducing systemic irritation and harmful effects.
Applied Scientific Principles
This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.
Function Achieved in This Case
The compound exhibits excellent antibacterial properties, maintaining effectiveness even after repeated washing, and can be applied to various fields like textiles, medicine, and food packaging, offering a green, immobilizable, and durable solution to bacterial infections.
Implementation Method 1
react with and bind to functional groups on surfaces of natural fibers, synthetic fibers and polymeric materials by a terminal isocyanate
Implementation Method 2
cell walls of bacteria are negatively charged, and ions, such as quaternary ammonium salts and the quaternary phosphonium salts, are positively charged. The quaternary ammonium salts with positive charges are liable to be absorbed by the bacteria
Implementation Method 3
penetrating the cell walls after approaching the bacteria, being bonded to the cytomembrane, and disrupting the composition of the cytomembrane, which results in leaking of intracellular materials and eventually death of the bacteria
Data Source
AI summary
A reactive antibacterial compound is represented by formula (I) or (II):wherein R1 represents OCN-L-NHCOOR′, OCN-L-NHCONHR′, OCN-L-NHCOSR′, OCN-L-COOR′, or OCN-L-COONHR′. G1 represents OCN-M-NHCOOG′, OCN-M-NHCONHG′, OCN-M-NHCOSG′, OCN-M-COOG′, or OCN-M-COONHG′. L, M, R′ and G′ independently for each occurrence represent divalent alkyl and cycloalkyl having from 1 to 18 carbon atoms, optionally substituted by up to 18 heteroatoms. R4 and G4 independently for each occurrence represent a divalent alkyl and cycloalkyl having from 1 to 18 carbon atoms, optionally substituted by up to 18 heteroatoms. G2 and G3 independently for each occurrence represent —H, —F, —Cl, —Br, —I, —OCH3, —OCH2CH3, —OPr, —CN, —SCN, —NO, —NO2, a monovalent unsubstituted or substituted alkyl, cycloalkyl, or aryl having from 1 to 7 carbon atoms. Z and X independently for each occurrence represent —COO, —SO3, or —OPO2OR5. R5 represents a monovalent unsubstituted or substituted alkyl, cycloalkyl, or aryl having from 1 to 6 carbon atoms.