Rational Design of Efficient Amine Reductant Initiators for Amine–Peroxide Redox Polymerization

Kim, Kangmin; Singstock, Nicholas R.; Childress, Kimberly K.; Sinha, Jasmine; Salazar, Austyn M.; Whitfield, Savannah N.; Holder, Aaron M.; Stansbury, Jeffrey W.; Musgrave, Charles B.

doi:10.1021/jacs.8b13679

Rational Design of Efficient Amine Reductant Initiators for Amine–Peroxide Redox Polymerization

Journal Article · Wed Mar 27 00:00:00 EDT 2019 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/jacs.8b13679· OSTI ID:1508958

Kim, Kangmin ^[1]; Singstock, Nicholas R. ^[1]; Childress, Kimberly K. ^[1]; Sinha, Jasmine ^[1]; Salazar, Austyn M. ^[1]; Whitfield, Savannah N. ^[1]; Holder, Aaron M. ^[2]; Stansbury, Jeffrey W. ^[3]; Musgrave, Charles B. ^[2]

Univ. of Colorado, Boulder, CO (United States)
Univ. of Colorado, Boulder, CO (United States); National Renewable Energy Lab. (NREL), Golden, CO (United States)
Univ. of Colorado, Boulder, CO (United States); Univ. of Colorado, Denver, CO (United States)

Amine-peroxide redox polymerization (APRP) has been highly prevalent in industrial and medical applications since the 1950s, yet the initiation mechanism of this radical polymerization process is poorly understood so that innovations in the field are largely empirically driven and incremental. Through a combination of computational prediction and experimental analysis, we elucidate the mechanism of this important redox reaction between amines and benzoyl peroxide for the ambient production of initiating radicals. Our calculations show that APRP proceeds through S_N² attack by the amine on the peroxide but that homolysis of the resulting intermediate is the rate-determining step. We demonstrate a correlation between the computationally predicted initiating rate and the experimentally measured polymerization rate with an R² = 0.80. The new mechanistic understanding was then applied to computationally predict amine reductant initiators with faster initiating kinetics. This led to our discovery of N-(4-methoxyphenyl)pyrrolidine (MPP) as amine reductant, which we confirmed significantly outperforms current state-of-the-art tertiary aromatic amines by ~20-fold, making it the most efficient amine-peroxide redox initiator to date. The application of amines with superior kinetics such as MPP in APRP could greatly accelerate existing industrial processes, facilitate new industrial manufacturing methods, and improve biocompatibility in biomedical applications conducted with reduced initiator concentrations yet higher overall efficiency.

View Accepted Manuscript (DOE)

Research Organization:: National Renewable Energy Laboratory (NREL), Golden, CO (United States)

Sponsoring Organization:: National Science Foundation (NSF)

Grant/Contract Number:: AC36-08GO28308

OSTI ID:: 1508958

Report Number(s):: NREL/JA--5K00-73770

Journal Information:: Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 15 Vol. 141; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

References (82)

Application of long chain amine activator in conventional acrylic bone cement Vazquez, B.; San Roman, J.; Deb, S. Journal of Biomedical Materials Research, Vol. 43, Issue 2 https://doi.org/10.1002/(SICI)1097-4636(199822)43:2<131::AID-JBM7>3.0.CO;2-P	journal	July 1998
Analyzing Reaction Rates with the Distortion/Interaction-Activation Strain Model Bickelhaupt, F. Matthias; Houk, Kendall N. Angewandte Chemie International Edition, Vol. 56, Issue 34 https://doi.org/10.1002/anie.201701486	journal	July 2017
Polystyrene/attapulgite nanocomposites prepared via in situ suspension polymerization with redox initiation system Yang, Haicun; Zhang, Liu; Ma, Wenzhong Journal of Applied Polymer Science https://doi.org/10.1002/app.41567	journal	October 2014
Fabrication of poly(methyl methacrylate) microfluidic chips by redox-initiated polymerization Chen, Jiang; Lin, Yuehe; Chen, Gang ELECTROPHORESIS, Vol. 28, Issue 16 https://doi.org/10.1002/elps.200700071	journal	August 2007
A self-healing biomaterial based on free-radical polymerization: A Self-Healing Biomaterial Dailey, Mary M. Caruso; Silvia, Alexander W.; McIntire, Patrick J. Journal of Biomedical Materials Research Part A, Vol. 102, Issue 9 https://doi.org/10.1002/jbm.a.34975	journal	October 2013
6-31G* basis set for third-row atoms Rassolov, Vitaly A.; Ratner, Mark A.; Pople, John A. Journal of Computational Chemistry, Vol. 22, Issue 9 https://doi.org/10.1002/jcc.1058	journal	January 2001
The role of amine in vinyl radical polymerization Feng, Xin-De Makromolekulare Chemie. Macromolecular Symposia, Vol. 63, Issue 1 https://doi.org/10.1002/masy.19920630105	journal	October 1992
Investigation of redox initiators for free radical frontal polymerization: Redox initiators for free radical frontal polymerization Yu, Huan; Fang, Yuan; Chen, Li Polymer International, Vol. 58, Issue 8 https://doi.org/10.1002/pi.2590	journal	June 2009
Do general nucleophilicity scales exist?: NUCLEOPHILICITY SCALES Mayr, Herbert; Ofial, Armin R. Journal of Physical Organic Chemistry, Vol. 21, Issue 7-8 https://doi.org/10.1002/poc.1325	journal	May 2008
Vinyl polymerization. V. Decomposition of sym-substituted benzoyl peroxides in the presence of dimethylaniline Imoto, Minoru; Choe, Seuckon Journal of Polymer Science, Vol. 15, Issue 80 https://doi.org/10.1002/pol.1955.120158015	journal	February 1955
Polymerization with redox initiators. III. Complex formation between benzoyl peroxide and dimethylaniline O'Driscoll, K. F.; Richezza, E. N. Journal of Polymer Science, Vol. 46, Issue 147 https://doi.org/10.1002/pol.1960.1204614719	journal	September 1960
Kinetics of polymerization of styrene initiated by substituted benzoyl peroxides. III. Induced decomposition O'Driscoll, K. F.; Lyons, P. F.; Patsiga, R. Journal of Polymer Science Part A: General Papers, Vol. 3, Issue 4 https://doi.org/10.1002/pol.1965.100030424	journal	April 1965
Kinetics of polymerization of styrene initiated by substituted benzoyl peroxides. IV. Decomposition induced by substituted diethylanilines O'driscoll, Kenneth F. Journal of Polymer Science Part A-1: Polymer Chemistry, Vol. 5, Issue 7 https://doi.org/10.1002/pol.1967.150050726	journal	July 1967
Evaluation of peroxide initiators for radical polymerization-based self-healing applications: Evaluation of Peroxide Initiators Wilson, Gerald O.; Henderson, James W.; Caruso, Mary M. Journal of Polymer Science Part A: Polymer Chemistry, Vol. 48, Issue 12 https://doi.org/10.1002/pola.24053	journal	May 2010
Domino free radical photopolymerization based on phototriggered base proliferation reaction and redox initiation He, Minghui; Jiang, Shun; Xu, Ruixin Journal of Polymer Science Part A: Polymer Chemistry, Vol. 52, Issue 11 https://doi.org/10.1002/pola.27149	journal	March 2014
3D Printing of Flexible Electronic Devices Yang, Hui; Leow, Wan Ru; Chen, Xiaodong Small Methods, Vol. 2, Issue 1 https://doi.org/10.1002/smtd.201700259	journal	November 2017
Organic Flexible Electronics Ling, Haifeng; Liu, Shenghua; Zheng, Zijian Small Methods, Vol. 2, Issue 10 https://doi.org/10.1002/smtd.201800070	journal	June 2018
Heavy Metal Toxicity and the Environment Tchounwou, Paul B.; Yedjou, Clement G.; Patlolla, Anita K. Experientia Supplementum https://doi.org/10.1007/978-3-7643-8340-4_6	book	January 2012
Effect of cross-linking agents on the molecular properties of denture base resins Moharram, M. A.; Abdel Nour, K. N.; Abdel Hakeem, N. Journal of Materials Science, Vol. 27, Issue 22 https://doi.org/10.1007/BF01133747	journal	January 1992
The influence of tertiary aromatic amines on the BPO initiated cure of unsaturated epoxy polyesters with styrene studied by non-isothermal DSC Worzakowska, Marta Journal of Thermal Analysis and Calorimetry, Vol. 105, Issue 3 https://doi.org/10.1007/s10973-011-1561-2	journal	April 2011
The interaction between benzoyl peroxide and triethylamine and polymerization in the presence of this system Margaritova, M. F.; Musabekova, I. Yu. Polymer Science U.S.S.R., Vol. 3, Issue 4 https://doi.org/10.1016/0032-3950(62)90315-5	journal	January 1962
Redox polymerization Misra, G. S.; Bajpai, U. D. N. Progress in Polymer Science, Vol. 8, Issue 1-2 https://doi.org/10.1016/0079-6700(82)90008-9	journal	January 1982
Effect of phenolic compounds on the polymerization of methyl methacrylate Fujisawa, S.; Kadoma, Y. Dental Materials, Vol. 8, Issue 5 https://doi.org/10.1016/0109-5641(92)90108-O	journal	September 1992
Temperature and viscosity dependence of the electron-transfer reaction between plastocyanin and cytochrome c labeled with a ruthenium(II) bipyridine complex Harris, Michele R.; Davis, Dan J.; Durham, Bill Biochimica et Biophysica Acta (BBA) - Bioenergetics, Vol. 1319, Issue 2-3 https://doi.org/10.1016/S0005-2728(96)00155-7	journal	April 1997
Contribution of Translational and Rotational Motions to Molecular Association in Aqueous Solution Yu, Y. Bruce; Privalov, Peter L.; Hodges, Robert S. Biophysical Journal, Vol. 81, Issue 3 https://doi.org/10.1016/S0006-3495(01)75817-1	journal	September 2001
N-(Benzoyloxy)amines: an investigation of their thermal stability, synthesis, and incorporation into novel peptide constructs Nemchik, Anne; Badescu, Valentina; Phanstiel, Otto Tetrahedron, Vol. 59, Issue 24 https://doi.org/10.1016/S0040-4020(03)00635-5	journal	June 2003
The mechanism of radical production from the reaction of N,N-dimethylaniline with benzoyl peroxide. Pryor, William A.; Hendrickson, William H. Tetrahedron Letters, Vol. 24, Issue 14 https://doi.org/10.1016/S0040-4039(00)81681-0	journal	January 1983
Redox polymerization Sarac, A. S. Progress in Polymer Science, Vol. 24, Issue 8 https://doi.org/10.1016/S0079-6700(99)00026-X	journal	October 1999
Analysis of the leaching and toxicity of new amine activators for the curing of acrylic bone cements and composites Liso, Pedro A.; Vázquez, Blanca; Rebuelta, Mercedes Biomaterials, Vol. 18, Issue 1 https://doi.org/10.1016/S0142-9612(96)00082-8	journal	January 1997
Solvent fluctuations and viscosity-dependent rates of solution reactions in a regime indescribable by the transition state theory Sumi, Hitoshi Journal of Molecular Liquids, Vol. 90, Issue 1-3 https://doi.org/10.1016/S0167-7322(01)00121-0	journal	February 2001
Systematic review of the chemical composition of contemporary dental adhesives Van Landuyt, Kirsten L.; Snauwaert, Johan; De Munck, Jan Biomaterials, Vol. 28, Issue 26 https://doi.org/10.1016/j.biomaterials.2007.04.044	journal	September 2007
Electrical properties of resin monomers used in restorative dentistry Breschi, Marco; Fabiani, Davide; Sandrolini, Leonardo Dental Materials, Vol. 28, Issue 9 https://doi.org/10.1016/j.dental.2012.05.009	journal	September 2012
3D printing with polymers: Challenges among expanding options and opportunities Stansbury, Jeffrey W.; Idacavage, Mike J. Dental Materials, Vol. 32, Issue 1 https://doi.org/10.1016/j.dental.2015.09.018	journal	January 2016
Redox and photoinitiated crosslinking polymerization Studer, Katia; Nguyen, Phuong Tri; Decker, Christian Progress in Organic Coatings, Vol. 54, Issue 3 https://doi.org/10.1016/j.porgcoat.2005.06.011	journal	November 2005
Polymers for 3D Printing and Customized Additive Manufacturing Ligon, Samuel Clark; Liska, Robert; Stampfl, Jürgen Chemical Reviews, Vol. 117, Issue 15 https://doi.org/10.1021/acs.chemrev.7b00074	journal	July 2017
Amine Induced Retardation of the Radical-Mediated Thiol–Ene Reaction via the Formation of Metastable Disulfide Radical Anions Love, Dillon M.; Kim, Kangmin; Goodrich, John T. The Journal of Organic Chemistry, Vol. 83, Issue 5 https://doi.org/10.1021/acs.joc.8b00143	journal	February 2018
Effect of Solution Viscosity on Intramolecular Electron Transfer in Sulfite Oxidase ^† Feng, Changjian; Kedia, Rohit V.; Hazzard, James T. Biochemistry, Vol. 41, Issue 18 https://doi.org/10.1021/bi016059f	journal	May 2002
Reaction of nucleophiles with electron acceptors by SN2 or electron transfer (ET) mechanisms: tert-butyl peroxybenzoate/dimethyl sulfide and benzoyl peroxide/N,N-dimethylaniline systems Pryor, William A.; Hendrickson, William H. Journal of the American Chemical Society, Vol. 105, Issue 24 https://doi.org/10.1021/ja00362a016	journal	November 1983
Relationship between the gas-phase entropies of molecules and their entropies of solvation in water and 1-octanol Wertz, David H. Journal of the American Chemical Society, Vol. 102, Issue 16 https://doi.org/10.1021/ja00536a033	journal	July 1980
Natural hybrid orbitals Foster, J. P.; Weinhold, F. Journal of the American Chemical Society, Vol. 102, Issue 24 https://doi.org/10.1021/ja00544a007	journal	September 1980
Studies of the Mechanisms of the Reactions of Benzoyl Peroxide with Secondary Amines and Phenols Denney, Donald B.; Denney, Dorothy Z. Journal of the American Chemical Society, Vol. 82, Issue 6 https://doi.org/10.1021/ja01491a026	journal	March 1960
Solvent Effects and Initiator Efficiency in the Benzoyl Peroxide-Dimethylaniline System ¹ Walling, Cheves; Indictor, Norman Journal of the American Chemical Society, Vol. 80, Issue 21 https://doi.org/10.1021/ja01554a057	journal	November 1958
Iridium-Catalyzed Borylation of Benzene with Diboron. Theoretical Elucidation of Catalytic Cycle Including Unusual Iridium(V) Intermediate Tamura, Hitoshi; Yamazaki, Hideki; Sato, Hirofumi Journal of the American Chemical Society, Vol. 125, Issue 51 https://doi.org/10.1021/ja0302937	journal	December 2003
Theoretical Study of the Cp ₂ Zr-Catalyzed Hydrosilylation of Ethylene. Reaction Mechanism Including New σ-Bond Activation Sakaki, Shigeyoshi; Takayama, Tatsunori; Sumimoto, Michinori Journal of the American Chemical Society, Vol. 126, Issue 10 https://doi.org/10.1021/ja0304345	journal	February 2004
Theoretical Study of Trans-metalation Process in Palladium-Catalyzed Borylation of Iodobenzene with Diboron Sumimoto, Michinori; Iwane, Naoki; Takahama, Tomohiko Journal of the American Chemical Society, Vol. 126, Issue 33 https://doi.org/10.1021/ja040020r	journal	August 2004
Reduction of CO ₂ to Methanol Catalyzed by a Biomimetic Organo-Hydride Produced from Pyridine Lim, Chern-Hooi; Holder, Aaron M.; Hynes, James T. Journal of the American Chemical Society, Vol. 136, Issue 45 https://doi.org/10.1021/ja510131a	journal	November 2014
Radical Cage Effects: Comparison of Solvent Bulk Viscosity and Microviscosity in Predicting the Recombination Efficiencies of Radical Cage Pairs Barry, Justin T.; Berg, Daniel J.; Tyler, David R. Journal of the American Chemical Society, Vol. 138, Issue 30 https://doi.org/10.1021/jacs.6b05432	journal	July 2016
Polymerization Initiated by Particle Contact: A Quiescent State Trigger for Materials Synthesis Hutchins, Kristin M.; Sekerak, Nina M.; Moore, Jeffrey S. Journal of the American Chemical Society, Vol. 138, Issue 38 https://doi.org/10.1021/jacs.6b07742	journal	September 2016
Estimating the Entropic Cost of Self-Assembly of Multiparticle Hydrogen-Bonded Aggregates Based on the Cyanuric Acid·Melamine Lattice Mammen, Mathai; Shakhnovich, Eugene I.; Deutch, John M. The Journal of Organic Chemistry, Vol. 63, Issue 12 https://doi.org/10.1021/jo970944f	journal	June 1998
Synthesis of Secondary Amines via N -(Benzoyloxy)amines and Organoboranes Phanstiel, O.; Wang, Q. X.; Powell, D. H. The Journal of Organic Chemistry, Vol. 64, Issue 3 https://doi.org/10.1021/jo981613l	journal	January 1999
Qualitative Features of Electron Transfer Reaction for High Viscosity of Solvent and Low Activation Barrier Okada, Akira The Journal of Physical Chemistry A, Vol. 104, Issue 33 https://doi.org/10.1021/jp0006328	journal	August 2000
Universal Solvation Model Based on Solute Electron Density and on a Continuum Model of the Solvent Defined by the Bulk Dielectric Constant and Atomic Surface Tensions Marenich, Aleksandr V.; Cramer, Christopher J.; Truhlar, Donald G. The Journal of Physical Chemistry B, Vol. 113, Issue 18, p. 6378-6396 https://doi.org/10.1021/jp810292n	journal	May 2009
Kinetics of the Benzoyl Peroxide/Amine Initiated Free-Radical Polymerization of Dental Dimethacrylate Monomers: Experimental Studies and Mathematical Modeling for TEGDMA and Bis-EMA Achilias, Dimitris S.; Sideridou, Irini D. Macromolecules, Vol. 37, Issue 11 https://doi.org/10.1021/ma049803n	journal	June 2004
Reactivity of Benzoyl Peroxide/Amine System as an Initiator for the Free Radical Polymerization of Dental and Orthopaedic Dimethacrylate Monomers: Effect of the Amine and Monomer Chemical Structure Sideridou, Irini D.; Achilias, Dimitris S.; Karava, Olga Macromolecules, Vol. 39, Issue 6 https://doi.org/10.1021/ma0521351	journal	March 2006
Atom Transfer Radical Polymerization (ATRP): Current Status and Future Perspectives Matyjaszewski, Krzysztof Macromolecules, Vol. 45, Issue 10, p. 4015-4039 https://doi.org/10.1021/ma3001719	journal	April 2012
Phototriggered Base Proliferation: A Highly Efficient Domino Reaction for Creating Functionally Photo-Screened Materials He, Minghui; Huang, Xun; Zeng, Zhaohua Macromolecules, Vol. 46, Issue 16 https://doi.org/10.1021/ma400983t	journal	August 2013
A DFT Study of the Full Catalytic Cycle of the Suzuki−Miyaura Cross-Coupling on a Model System Braga, Ataualpa A. C.; Ujaque, Gregori; Maseras, Feliu Organometallics, Vol. 25, Issue 15 https://doi.org/10.1021/om060380i	journal	July 2006
Mechanistic Studies on the Reversible Hydrogenation of Carbon Dioxide Catalyzed by an Ir-PNP Complex Tanaka, Ryo; Yamashita, Makoto; Chung, Lung Wa Organometallics, Vol. 30, Issue 24 https://doi.org/10.1021/om2010172	journal	December 2011
Redox initiation of bulk thiol–ene polymerizations Cole, Megan A.; Jankousky, Katherine C.; Bowman, Christopher N. Polym. Chem., Vol. 4, Issue 4 https://doi.org/10.1039/C2PY20843A	journal	January 2013
Simulation of radical polymerization of methyl methacrylate at room temperature using a tertiary amine/BPO initiating system Zoller, Alexander; Gigmes, Didier; Guillaneuf, Yohann Polymer Chemistry, Vol. 6, Issue 31 https://doi.org/10.1039/C5PY00229J	journal	January 2015
Benzoylformamides as versatile photocaged bases for redox free radical photopolymerization Xu, Ruixin; He, Minghui; Yang, Jianwen Photochemical & Photobiological Sciences, Vol. 15, Issue 11 https://doi.org/10.1039/C6PP00301J	journal	January 2016
MN15: A Kohn–Sham global-hybrid exchange–correlation density functional with broad accuracy for multi-reference and single-reference systems and noncovalent interactions Yu, Haoyu S.; He, Xiao; Li, Shaohong L. Chemical Science, Vol. 7, Issue 8 https://doi.org/10.1039/C6SC00705H	journal	January 2016
Photopolymerization processes of thick films and in shadow areas: a review for the access to composites Garra, Patxi; Dietlin, Céline; Morlet-Savary, Fabrice Polymer Chemistry, Vol. 8, Issue 46 https://doi.org/10.1039/C7PY01778B	journal	January 2017
On the Relative Roles of Free Volume and Activation Energy in the Viscosity of Liquids Macedo, P. B.; Litovitz, T. A. The Journal of Chemical Physics, Vol. 42, Issue 1 https://doi.org/10.1063/1.1695683	journal	January 1965
Viscosity, Plasticity, and Diffusion as Examples of Absolute Reaction Rates Eyring, Henry The Journal of Chemical Physics, Vol. 4, Issue 4 https://doi.org/10.1063/1.1749836	journal	April 1936
A restricted-open-shell complete-basis-set model chemistry Wood, Geoffrey P. F.; Radom, Leo; Petersson, George A. The Journal of Chemical Physics, Vol. 125, Issue 9 https://doi.org/10.1063/1.2335438	journal	September 2006
Dynamical effects in electron transfer reactions Sumi, H.; Marcus, R. A. The Journal of Chemical Physics, Vol. 84, Issue 9 https://doi.org/10.1063/1.449978	journal	May 1986
Is coupled cluster singles and doubles (CCSD) more computationally intensive than quadratic configuration interaction (QCISD)? Scuseria, Gustavo E.; Schaefer, Henry F. The Journal of Chemical Physics, Vol. 90, Issue 7 https://doi.org/10.1063/1.455827	journal	April 1989
Coupled‐cluster methods with noniterative triple excitations for restricted open‐shell Hartree–Fock and other general single determinant reference functions. Energies and analytical gradients Watts, John D.; Gauss, Jürgen; Bartlett, Rodney J. The Journal of Chemical Physics, Vol. 98, Issue 11 https://doi.org/10.1063/1.464480	journal	June 1993
A complete basis set model chemistry. VII. Use of the minimum population localization method Montgomery, J. A.; Frisch, M. J.; Ochterski, J. W. The Journal of Chemical Physics, Vol. 112, Issue 15 https://doi.org/10.1063/1.481224	journal	April 2000
Single-reference coupled cluster theory for multi-reference problems Margraf, Johannes T.; Perera, Ajith; Lutz, Jesse J. The Journal of Chemical Physics, Vol. 147, Issue 18 https://doi.org/10.1063/1.5003128	journal	November 2017
Study of the Effect of two Bpo/Amine Initiation Systems on the Free-Radical Polymerization of mma used in Dental Resins and bone Cements Achilias, Dimitris S.; Sideridou, Irini Journal of Macromolecular Science, Part A, Vol. 39, Issue 12 https://doi.org/10.1081/MA-120016045	journal	January 2002
Electron transfer reactions in chemistry. Theory and experiment Marcus, Rudolph A. Reviews of Modern Physics, Vol. 65, Issue 3, p. 599-610 https://doi.org/10.1103/RevModPhys.65.599	journal	July 1993
Cure mechanisms in materials for use in esthetic dentistry: Cure mechanisms in dentistry Kwon, Tae-Yub; Bagheri, Rafat; Kim, Young K. Journal of Investigative and Clinical Dentistry, Vol. 3, Issue 1 https://doi.org/10.1111/j.2041-1626.2012.00114.x	journal	February 2012
Oxidation of N,N-Dimethylaniline: I.The Reaction with Benzoyl Peroxide Graham, Donald M.; Mesrobian, Robert B. Canadian Journal of Chemistry, Vol. 41, Issue 12 https://doi.org/10.1139/v63-432	journal	December 1963
Origins and Development of Initiation of Free Radical Polymerization Processes Braun, Dietrich International Journal of Polymer Science, Vol. 2009 https://doi.org/10.1155/2009/893234	journal	January 2009
Amine Accelerators for Methacrylate Resin Systems Bowen, R. L.; Argentar, H. Journal of Dental Research, Vol. 50, Issue 4 https://doi.org/10.1177/00220345710500042301	journal	July 1971
Tertiary Aromatic Amine Accelerators with Molecular Weights Above 400 Bowen, R. L.; Argentar, H. Journal of Dental Research, Vol. 51, Issue 2 https://doi.org/10.1177/00220345720510023801	journal	March 1972
Polymerizable Amines as Promoters of Cold-Curing Resins and Composites Dneboský, J.; Hynková, V.; Hrabák, F. Journal of Dental Research, Vol. 54, Issue 4 https://doi.org/10.1177/00220345750540041301	journal	July 1975
4-N,N-Dialkylaminophenethanols,-Alkanoic Acids and Esters: New Accelerators for Dental Composites Brauer, G. M.; Stansbury, J. W.; Antonucci, J. M. Journal of Dental Research, Vol. 60, Issue 7 https://doi.org/10.1177/00220345810600071001	journal	July 1981
The effect of amine-free initiator system and the polymerization type on color stability of resin cements Ural, Çağrı; Duran, İbrahim; Tatar, Numan Journal of Oral Science, Vol. 58, Issue 2 https://doi.org/10.2334/josnusd.15-0619	journal	January 2016
13C-NMR Based Evaluation of the Electronic and Steric Interactions in Aromatic Amines Zakrzewska, Anna; Gawinecki, Ryszard; Kolehmainen, Erkki International Journal of Molecular Sciences, Vol. 6, Issue 1 https://doi.org/10.3390/i6010052	journal	January 2005

Cited By (1)

Catalyst-free, aza-Michael polymerization of hydrazides: polymerizability, kinetics, and mechanistic origin of an α-effect Love, Dillon; Kim, Kangmin; Domaille, Dylan W. Polymer Chemistry, Vol. 10, Issue 42 https://doi.org/10.1039/c9py01199d	journal	January 2019

Similar Records

Computational and Experimental Evaluation of Peroxide Oxidants for Amine-Peroxide Redox Polymerization

Journal Article · Thu Nov 12 23:00:00 EST 2020 · Macromolecules · OSTI ID:1770899

Skin tumor-promoting activity of benzoyl peroxide, a widely used free radical-generating compound

Journal Article · Fri Aug 28 00:00:00 EDT 1981 · Science (Washington, D.C.); (United States) · OSTI ID:5850793

Influence of solid compounds of vanadium on the decomposition of organic peroxides

Journal Article · Thu Aug 01 00:00:00 EDT 1985 · J. Gen. Chem. USSR (Engl. Transl.); (United States) · OSTI ID:7202785

Related Subjects

36 MATERIALS SCIENCE
APRP
amine-peroxide redox polymerization
polymerization
redox reactions

Rational Design of Efficient Amine Reductant Initiators for Amine–Peroxide Redox Polymerization

Citation Formats

References (82)

Cited By (1)

Similar Records

Related Subjects