Synthesis and Structural Characterization of Novel Urethane-Dimethacrylate Monomers with Two Quaternary Ammonium Groups Based on Cycloaliphatic Diisocyanates †
Abstract
1. Introduction
2. Materials and Methods
2.1. Materials
2.2. Synthesis of Monomers Possessing Quaternary Ammonium Groups
2.2.1. Synthesis of N,N-(2-hydroxyethyl)methylaminoethyl Methacrylate (HAMA)
2.2.2. Synthesis of 2-(Methacryloyloxy)ethyl-2-dodecylhydroxyethylmethylammonium Bromide (QAHAMA-12)
2.2.3. Synthesis of Quaternary Ammonium Urethane-Dimethacrylate Monomers (QA12 + IPDI and QA12 + CHMDI)
2.3. Nuclear Magnetic Resonance Spectroscopy (NMR)
2.4. Fourier Transform Infrared Spectroscopy (FTIR)
3. Results
3.1. 1H NMR
3.2. 13C NMR
3.3. FTIR Spectra
4. Discussion
5. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Substance | Mass (g) | Moles (mol) |
---|---|---|
Substrates | ||
MMA | 100.12 | 1.00 |
MDEA | 79.85 | 0.67 |
Transesterification catalyst | ||
K2CO3 | 14.40 | 1 |
Polymerization inhibitor | ||
PTZ | 0.05 | 1 |
Solvent | ||
Toluene | 346 | 1 |
Substance | Mass (g) | Moles (mol) |
---|---|---|
Substrates | ||
HAMA | 20.00 | 0.107 |
DDB | 26.67 | 0.107 |
Polymerization inhibitor | ||
PTZ | 0.01 | 1 |
QAUDMA | Substance | Mass (g) | Moles (mol) |
---|---|---|---|
QA12 + IPDI | QAHAMA-12 | 20.34 | 0.047 |
IPDI | 5.18 | 0.023 | |
DBTDL | 0.008 | 1 | |
QA12 + CHMDI | QAHAMA-12 | 22.82 | 0.052 |
CHMDI | 6.86 | 0.026 | |
DBTDL | 0.009 | 1 |
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Drejka, P.; Kula, P.; Barszczewska-Rybarek, I. Synthesis and Structural Characterization of Novel Urethane-Dimethacrylate Monomers with Two Quaternary Ammonium Groups Based on Cycloaliphatic Diisocyanates. Eng. Proc. 2025, 87, 20. https://doi.org/10.3390/engproc2025087020
Drejka P, Kula P, Barszczewska-Rybarek I. Synthesis and Structural Characterization of Novel Urethane-Dimethacrylate Monomers with Two Quaternary Ammonium Groups Based on Cycloaliphatic Diisocyanates. Engineering Proceedings. 2025; 87(1):20. https://doi.org/10.3390/engproc2025087020
Chicago/Turabian StyleDrejka, Patryk, Patrycja Kula, and Izabela Barszczewska-Rybarek. 2025. "Synthesis and Structural Characterization of Novel Urethane-Dimethacrylate Monomers with Two Quaternary Ammonium Groups Based on Cycloaliphatic Diisocyanates" Engineering Proceedings 87, no. 1: 20. https://doi.org/10.3390/engproc2025087020
APA StyleDrejka, P., Kula, P., & Barszczewska-Rybarek, I. (2025). Synthesis and Structural Characterization of Novel Urethane-Dimethacrylate Monomers with Two Quaternary Ammonium Groups Based on Cycloaliphatic Diisocyanates. Engineering Proceedings, 87(1), 20. https://doi.org/10.3390/engproc2025087020