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151. Novel Copolymers of Styrene and Halogen Ring‐Substituted 2‐Cyano‐N,N‐Dimethyl‐3‐Phenyl‐2‐Propenamides

Author

Kharas, Gregory B., primary, Tian, Xue, additional, Ackron, Traci A., additional, Akroush, Michael H., additional, O'brien, Kelly A., additional, Ostrovskaya, Ella, additional, Protega, Nicole, additional, Smith, Jennifer E. H., additional, Stock, Megan E., additional, Wenban, Bridget F., additional, and Werner, Eric, additional

Published
2007
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152. Novel Copolymers of Styrene and Halogen Ring‐Disubstituted 2‐Cyano‐N,N‐Dimethyl‐3‐Phenyl‐2‐Propenamides

Author

Kharas, Gregory B., primary, Tian, Xue, additional, Huynh, Trang H., additional, Lyons, Thomas W., additional, Macartney, Lani A., additional, Smith, Dylan, additional, Mallios, Jenelle L., additional, Nguyen, Nancy, additional, Sandifer, Jamie L., additional, Stankovich, Daniel S., additional, Szwajnos, Joanna J., additional, and Tadros, Hakam I., additional

Published
2007
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153. Novel Copolymers of Styrene and Di‐ and Trimethoxy Ring‐Substituted 2‐Cyano‐N,N‐dimethyl‐3‐phenyl‐2‐propenamides

Author

Kharas, Gregory B., primary, Tian, Xue, additional, Denson, Stephen P., additional, Duzo, Emina, additional, Ekram, Adnan, additional, Elnaggar, Dina, additional, Epperson, Megan L., additional, Hai, Asra K., additional, Haider, Ali, additional, Hatch, Amanda C., additional, Johnson, Jennifer, additional, and Palafox, Joana, additional

Published
2007
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155. Novel Copolymers of Styrene and Alkyl Ring‐Substituted 2‐Cyano‐N,N‐dimethyl‐3‐phenyl‐2‐propenamides

Author

Kharas, Gregory B., primary, Tian, Xue, additional, Castle, Whitney K., additional, Curran, Jerry W., additional, Demetzensky, Hellene, additional, Fath, Maria R., additional, Fatima, Farida, additional, Ghorbanpour, Mojgan B., additional, Barnes, Rebecca L., additional, Merideth, Hope, additional, and Russel, Selena M., additional

Published
2007
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156. Novel Copolymers of Styrene. 5. Some Ring-Substituted 2-Cyano-3-phenyl-2-propenamides.

Author

Kharas, Gregory B., De Boer, Deborah M., Fellows, Miranda E., Gonzalez, Sheila, Mahoney, Ryan J., Mandas, Katina C., Mazur, Nicole X., and Michalak, Grzegorz P.

Subjects
*COPOLYMERS, *STYRENE, *CYCLIC compounds, *ACRYLAMIDE, *NUCLEAR magnetic resonance
Abstract

Novel trisubstituted ethylenes, ring substituted 2-cyano-3-phenyl-2-propenamides, RC6H4CH=C(CN)CONH2(where R is 4-carboxy, 2-cyano, 3-cyano, 4-cyano, 4-dimethylamino, and 4-diethylamino) were synthesized by potassium hydroxide catalyzed Knoevenagel condensation of ring-substituted benzaldehydes and cyanoacetamide prepared and characterized by CHN elemental analysis, IR,1H‒ and13C‒NMR. Novel copolymers of the ethylenes and styrene were prepared at equimolar monomer feed composition by solution in the presence of a radical initiation (AIBN) at 70°C. The composition of the copolymers was calculated from nitrogen analysis, and the structures were analyzed by IR,1H‒ and13C‒NMR, GPC, DSC, and TGA. Thus, the order of relative reactivity (1/r1) and the tendency toward alternation of monomer units in the copolymer for the CPA monomers is 4-(C2H5)2N (0.40) > 4-CO2H (0.39) > 3-CN (0.36) > 4-CN (0.35) > 2-CN (0.34) > 4-(CH3)2N (0.33). HighTgof the copolymers in comparison with that of polystyrene indicates a substantial decrease in chain mobility of the copolymer due to the high dipolar character of the trisubstituted ethylene monomer unit. Decomposition of the copolymers in nitrogen occurred in two steps, first in the 200–500°C range with residue (3.5–5.0 wt%), which then decomposed in the 500–800°C range. [ABSTRACT FROM AUTHOR]

Published
2015
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163. Novel Copolymers of Vinyl Acetate and Halogen Ring‐Disubstituted Methyl 2‐Cyano‐3‐phenyl‐2‐propenoates

Author

Kharas, Gregory B., primary, Crawford, Allison L., additional, Aguirre, Patricia, additional, Baran, Annette W., additional, Bernal, Rocio, additional, Breier, Christopher J., additional, Escudero, Carolina, additional, Gomez, Citlaly R., additional, Hughes, Patricia B., additional, Joudeh, Maged J., additional, Kearney, Jannet, additional, and Watson, Kenneth, additional

Published
2005
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165. Novel Copolymers of Vinyl Acetate and Alkoxy Ring‐Substituted Methyl 2‐cyano‐3‐phenyl‐2‐propenoates

Author

Kharas, Gregory B., primary, Crawford, Allison L., additional, Johnson, Jennifer E., additional, Marcus, Marcella M., additional, Martin, Carolyn F., additional, Novales, Jed E., additional, Joudeh, Maged J., additional, Onimole, Yemisi T., additional, Staehlin, Michael, additional, Hoang, Joseph M., additional, Belavsky, Benjamin Z., additional, and Watson, Kenneth, additional

Published
2005
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166. Novel co-polymers of vinyl acetate and halogen ring-substituted methyl 2-cyano-3-phenyl-2-propenoates

Author

Kharas, Gregory B., primary, Barbarawi, Hadeal A., additional, Crawford, Allison L., additional, Dotson-Newman, Ogonnaya I., additional, Dukarevich, Igor J., additional, Ekram, Adnan, additional, Galzin, Nicholas A., additional, Ghattas, Rasha M., additional, Hoang, Joseph M., additional, Hyland, Lesley A., additional, Isic, Bedrija, additional, Gutierrez, Jorge, additional, and Watson, Kenneth, additional

Published
2005
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167. Novel co-polymers of vinyl acetate and alkyl ring-substituted methyl 2-cyano-3-phenyl-2-propenoates

Author

Kharas, Gregory B., primary, Crawford, Allison L., additional, Bernal, Rocio, additional, Kallal, Lara, additional, Thomas, Vickie, additional, Tokman, Sofya, additional, Trnka, Maureen C., additional, Hyland, Lesley A., additional, Hughes, Patricia, additional, Carney, Jason, additional, Trujillo, Anna M., additional, Hanks, Madeleine, additional, and Watson, Kenneth, additional

Published
2005
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168. Synthesis and copolymerization of ring-substituted N-(aminocarbonyl)-2-cyano-3-phenyl-2-propenamides with styrene

Author

Kharas, Gregory B., primary, McColough, Kristen E., additional, Heiskell, Jeffrey R., additional, Herrman, Julia E., additional, Levun, Jami A., additional, Lucchetta, Elena M., additional, Villaseñor, Gilbert, additional, Parish-Chafey, Laurie A., additional, Schreiber, Peter J., additional, O'Malley, Paul A., additional, Starkman, Bela G., additional, Verdoorn, Gretchen, additional, Passe, Laura B., additional, and Watson, Kenneth, additional

Published
2003
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169. NOVEL COPOLYMERS OF TRISUBSTITUTED ETHYLENES AND STYRENE. I. ALKYL AND ALKOXY RING-SUBSTITUTED ETHYL 2-CYANO-1-OXO-3-PHENYL-2-PROPENYLCARBAMATES

Author

Kharas, Gregory B., primary, Fuerst, Antonia M., additional, Scola, Anthony, additional, Bavirsha, Daniel J., additional, Bernau, Bradley M., additional, Brown, Santkileo K., additional, Ece, Pasa, additional, Dabrowski, Anna N., additional, De Angelo, Penny, additional, Fatemi, Farrah R., additional, and Watson, Kenneth, additional

Published
2002
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171. SYNTHESIS AND RADICAL COPOLYMERIZATION OF TRISUBSTITUTED ETHYLENES WITH STYRENE. 6. ALKOXY, PHENOXY, AND CYANO RING-SUBSTITUTED METHYL-2-CYANO-3-PHENYL-2-PROPENOATES

Author

Kim, Katherine, primary, Blaine, Deborah A., additional, Brtek, Lisa M., additional, Flood, Rita M., additional, Krubert, Christopher G., additional, Rizzo, Ann Marie T., additional, Sterner, Elizabeth A., additional, De Armas, Sheila, additional, Kharas, Gregory B., additional, and Watson, Kenneth, additional

Published
2000
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172. Novel copolymers of trisubstituted ethylenes and styrene- 5. Ring-disubstituted methyl 2-cyano-3-phenyl-2-propenoates

Author

Kim, Katherine J., primary, Morales, Michelle, additional, Scully, Michael J., additional, Seitz, Christine D., additional, Sikora, Ann Marie, additional, Spaulding, Angela M., additional, Sudman, Ruthann, additional, Sullivan, Amy C., additional, Dean, Brian C., additional, Kharas, Gregory B., additional, and Watson, Kenneth, additional

Published
1999
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176. Novel Copolymers of Trisubstituted Ethylenes with Styrene. II. Halogen Ring-Substituted Methyl 2-Cyano-3-Phenyl-2-Propenoates

Author

Kharas, Gregory B., primary, Wheeler, Timothy S., additional, Eaker, Julie M., additional, Armatys, Sandra A., additional, Fehringer, Jessica A., additional, Gehant, Rachelle M., additional, Glaser, Elizabeth C., additional, Johnson, Katherine A., additional, Moy, Patricia S., additional, and Quinting, Gregory R., additional

Published
1995
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179. Novel copolymers of trisubstituted ethylenes with styrene — 7. Methyl 2-cyano-3-dihalophenyl-2-propenoates.

Author

Kharas, Gregory B., Kim, Katherine, Beinlich, Kimberly C., Benington, Sarah B., Brennan, Sarah K., Morales, Michelle, Ruano, Norman E., Won, Doo Y., Adibu, Emanuel, and Watson, Kenneth

Abstract

Methyl 2-cyano-3-dihalophenyl-2-propenoates, R2C6H3CH=C(CN)CO2CH3 (R2= 2,4-difluoro, 2,5-difluoro, 2,6-difluoro, 3,4-difluoro, 3,5-difluoro, and 2-chloro-6-fluoro), were prepared by the piperidine catalyzed Knoevenagel condensation of corresponding disubstituted benzaldehydes and methyl cyanoacetate. Novel copolymers of the propenoates and styrene were prepared at equimolar monomer feed by solution copolymerization in the presence of a radical initiator. The order of relative reactivity (1/ r1) was 2,5-difluoro (2.11) > 2,6-difluoro (1.84) > 3,5-difluoro (1.71) > 2,4-difluoro (1.4) > 3,4-difluoro (0.65) > 2-chloro-6-fluoro (0.59). The copolymers were characterized by IR, 1H and 13C NMR, GPC, DSC and TGA. High glass transition temperatures of the copolymers compared that of polystyrene indicates a substantial decrease in chain mobility of the copolymers due to the high dipolar character of the trisubstituted ethylene monomer unit. [ABSTRACT FROM AUTHOR]

Published
2000
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182. Synthesis and copolymerization of halogen phenyl-substituted methyl 2-cyano-3-phenyl-2-propenoates with styrene.

Author

Kim, Katherine, Butler, Cynthia A., Cisneros, Maria R., Ryan, Susan L., Schwartz, Marc A., Lindquist, Nancy A., Kharas, Gregory B., and DeFrancesco, James V.

Abstract

Halogen phenyl-substituted methyl 2-cyano-3-phenyl-2-propenoates, RC6H4CH=C(CN)CO2CH3 (R= 2-fluoro, 3-fluoro, 2-bromo, and 3-bromo), were prepared by the piperidine catalyzed Knoevenagel condensation of corresponding substituted benzaldehydes and methyl cyanoacetate. Novel copolymers of the propenoates and styrene were prepared at equimolar monomer feed by solution copolymerization in the presence of a radical initiator. The order of relative reactivity (1/ r1) was 3Br (3.02) > 2Br (2.63) > 3F (1.84) > 2F (1.66). High glass transition temperatures of the copolymers compared that of polystyrene indicates a substantial decrease in chain mobility of the copolymers due to the high dipolar character of the trisubstituted ethylene monomer unit. [ABSTRACT FROM AUTHOR]

Published
1998
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183. Novel copolymers of trisubstituted ethylenes and styrene - 3. Ring-substituted methyl 2-cyano-3-phenyl-2-propenoates

Author

Sun, Ying, McManigal, Kelly A., Larson, Gregory M., Monohan, Jennifer, Sawicki, Anna D., Kharas, Gregory B., and Quinting, Gregory R.

Abstract

Electrophilic trisubstituted ethylenes, phenyl-substituted methyl 2-cyano-3-phenyl-2-propenoates, RC6H4CH=C(CN)CO2CH3(where R = p-CN, p-NHCOCH3, o-NO2'p-NO2), were prepared and characterized. The feasibility of copolymerization of the monomers with styrene (M1) was investigated in solution at an equimolar feed ratio in the presence of a radical initiator, 2,2-azobisisobutyronitrile (AIBN), at 80°C. Nitro-substituted propenoates did not form styrene copolymers. The relative reactivity (1/r1) for p-CN and p-NHCOCH3substituted monomers was 41.2 and 0.38, respectively.

Published
1998
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186. Synthesis and radical copolymerization of novel propyl cyanoacrylate monomers.

Author

Knight, Jonathon D., Arellano, Lissette, Conger, Kelly O., Crespo, Edgar J., Hollembeak, Jordan E., Jazdzewski, Nicole M., Pater, Adrian A., Possley, Daniel H., Rivera, Kaela N., Saucedo, Cesar, Spitz, Justin E., Vacala, Taylor L., Woo, Nicholas W., Schjerven, William S., and Kharas, Gregory B.

Subjects
*COPOLYMERIZATION, *MONOMERS, *BENZALDEHYDE, *COPOLYMERS
Abstract

Novel phenyl-trisubstituted propyl 3-(R-phenyl)-2-cyanoacrylates (where R is 2,4,5-trimethyl, 2,4,6-trimethyl, 2,3-dimethyl-4-methoxy, 2,5-dimethyl-4-methoxy, 2,4-dimethoxy-3-methyl, 2,4-dimethoxy-6-methyl, 4-hydoxy-3,5-dimethyl, 2,3,4-trimethoxy, 2,4,5-trimethoxy, 2,4,6-trimethoxy, 3,4,5-trimethoxy) were prepared using piperidine-catalyzed condensation of substituted benzoic aldehydes and propyl ester of cyanoacetic acid with good yields (72–97 wt%). The ethenylbenzene copolymerization of cyanoacrylates (at 3/1 mol feed ratio) in solution with radical initiation at 70 °C resulted in formation of copolymers having MW 3.9 to 27.8 kD and 8.4–25.8 mol% of cyanoacrylate. FTIR, 1H and 13C NMR were used to analyze the structure. Thermal behavior of the copolymers was analyzed by DSC, Tg (81–129 °C) and TGA. Decomposition of the copolymers in nitrogen occurred in two steps, first in the 200–500 °C range with residue (0.5–7.3 wt%)and then in the 500–800 °C range. [ABSTRACT FROM AUTHOR]

Published
2020
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187. Synthesis and styrene copolymerization of novel trisubstituted ethylenes: 11. Halogen ring-substituted propyl 2-cyano-3-phenyl-2-propenoates.

Author

Humanski, Kara E., Patterson, Santanna D., Pecorin, Paul J., Perfitt, Madeline M., Romero, Janet, Sassack, William R., Sweeney, Samantha M., Talwar, Camille O., Tolentino, Dominique A., Wilson, Megan E., Schjerven, William S., and Kharas, Gregory B.

Subjects
*STYRENE, *COPOLYMERIZATION, *ALKENES, *FOURIER transform infrared spectroscopy, *COPOLYMERS
Abstract

Novel trisubstituted ethylenes, ring-substituted propyl 2-cyano-3-phenyl-2-propenoates, RPhCH=C(CN)CO2C3H7 (where R is 4-chloro-3-fluoro, 2-fluoro-5-iodo, 2-fluoro-6-iodo, 2-trifluoromethyl, 3-trifluoromethyl, 4-trifluoromethyl, 2-trifluoromethoxy, 3-trifluoromethoxy, and 4-trifluoromethoxy) were prepared and copolymerized with styrene. The ethylenes were synthesized by the piperidine catalyzed Knoevenagel condensation of ring-substituted benzaldehydes and propyl cyanoacetate and characterized by CHN analysis, FTIR, 1H and 13C NMR. All the ethylenes were copolymerized with styrene in solution with radical initiation (ABCN) at 70 °C. The composition of the copolymers was calculated from nitrogen analysis, and the structures were analyzed by FTIR, 1H and 13C NMR. Decomposition of the copolymers in nitrogen (TGA) occurred in two steps, first in the 250-500 °C range with residue (0.5-3.1% wt.), which then decomposed in the 500-700 °C range. [ABSTRACT FROM AUTHOR]

Published
2018
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188. Synthesis and styrene copolymerization of novel trisubstituted ethylenes: 1. Alkyl ring-substituted isopropyl 2-cyano-3-phenyl-2-propenoates.

Author

Pride, Rachel L., Anderson, Cara J., Aelion, Michelle S., Barry, Oumou S., Berry, Michael, Blankemeyer, Erica, Bolton, Madeline M., Bravo, Angelika, Chae, Isabelle, Franco, Cassidy M., Galindo, Mariana, Schjerven, William S., and Kharas, Gregory B.

Subjects
*STYRENE, *SUBSTITUTION reactions, *ALKENES, *COPOLYMERIZATION, *FOURIER transform infrared spectroscopy
Abstract

Novel trisubstituted ethylenes, alkyl ring-substituted isopropyl 2-cyano-3-phenyl-2-propenoates, RPhCH = C(CN)CO2CH(CH3)2 (where R is H, 2-methyl, 3-methyl, 4-methyl, 4-ethyl, 4-propyl, 4-i-propyl, 4-butyl, 4-i-butyl, 4-t-butyl) were prepared and copolymerized with styrene. The ethylenes were synthesized by the piperidine catalyzed Knoevenagel condensation of ring-substituted benzaldehydes and isopropyl cyanoacetate, and characterized by CHN analysis, IR, 1H and 13C NMR. All the ethylenes were copolymerized with styrene in solution with radical initiation (ABCN) at 70°C. The compositions of the copolymers were calculated from nitrogen analysis and the structures were analyzed by FTIR, 1H and 13C NMR. Decomposition of the copolymers in nitrogen occurred in two steps, first in the 250-500°C range with residue (2-5% wt.), which then decomposed in the 500-800°C range. [ABSTRACT FROM AUTHOR]

Published
2018
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189. Synthesis and vinyl benzene copolymerization of novel trisubstituted ethylenes: 15. Halogen and methoxy ring-substituted isopropyl 2-cyano-3-phenyl-2-propenoates.

Author

Kharas GB, Cimino A, Flieger S, Whelpley PM, Ebner D, Groy R, Savittieri CR, Shinde N, Thomas KL, Rocus SM, and Schjerven WS

Abstract

Condensation of isopropyl cyanoacetate and substituted benzoic aldehydes resulted in formation of novel isopropyl esters of 2-cyano-3-phenyl-2-propenoic acid, RPhCH = C(CN)CO 2 CH(CH 3 ) 2 (where R is 2,3,4-trimethoxy, 2,4,5-trimethoxy, 2,4,6-trimethoxy, 3-bromo-4,5-dimethoxy, 5-bromo-2,3-dimethoxy, 5-bromo-2,4-dimethoxy, 6-bromo-3,4-dimethoxy, 2-bromo-3-hydroxy-4-methoxy, 4-bromo-2,6-difluoro, 2-chloro-3,4-dimethoxy, 3-chloro-4,5-dimethoxy, 5-chloro-2,3-dimethoxy, 2,3,6-trichloro, 3-chloro-2,6-difluoro, 2,3,4-trifluoro, 2,4,5-trifluoro, 2,4,6-trifluoro, 3,4,5-trifluoro, 2,3,5,6-tetrafluoro, 2,3,4,5,6-pentafluoro). Copolymerization of the esters with vinyl benzene in solution with radical initiation (ABCN) at 70°C led to formation copolymers. The products were characterized by CHN elemental analysis, IR, 1  H- and 13  C-NMR, GPC, DSC, and TGA., Competing Interests: No potential conflict of interest was reported by the authors., (© 2020 The Author(s). Published by Informa UK Limited, trading as Taylor & Francis Group.)

Published
2020
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190. Synthesis and styrene copolymerization of novel trisubstituted ethylenes: 3. Alkoxy ring-substituted isopropyl 2-cyano-3-phenyl-2-propenoates.

Author

Kharas GB, Shinde N, Jody JK, Mosher EK, Kaur N, Oriol AAR, Perez DM, Ranganathan R, Renteria A, Rydbom TA, Yeager C, and Schjerven WS

Abstract

Novel trisubstituted ethylenes, alkoxy ring-substituted isopropyl 2-cyano-3-phenyl-2-propenoates, RPhCH = C(CN)CO 2 CH(CH 3 ) 2 (where R is 2-methoxy, 3-methoxy, 4-methoxy, 2-ethoxy, 3-ethoxy, 4-ethoxy, 4-propoxy, 4-butoxy, 4-hexyloxy) were prepared and copolymerized with styrene. The ethylenes were synthesized by the piperidine catalyzed Knoevenagel condensation of ring-substituted benzaldehydes and isopropyl cyanoacetate, and characterized by CHN analysis, FTIR, 1 H and 13 C NMR. All the ethylenes were copolymerized with styrene in solution with radical initiation (ABCN) at 70°C. The compositions of the copolymers were calculated from nitrogen analysis and the structures were analyzed by FTIR, 1 H and 13 C NMR. Decomposition of the copolymers in nitrogen occurred in two steps, first in the 250-500ºC range with residue (2.6-3.9% wt.), which then decomposed in the 500-800ºC range.

Published
2018
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