Novel copolymers of 4-fluorostyrene. 2. Alkoxy ring-substituted 2-phenyl-1,1-dicyanoethylenes

Gregory B. Kharas; Emi Hanawa; Benjamin L. Hill; Katherine T. Flynn; Nikesh H. Bajaj; Yousef Bittar; Mathew R. Dow; Sean Moloney; Thuy A. Nguyen; Stuart A. Pitts; Christina A. Serret; Janeth Valadez; Ana C. Vallejo; Salima Atlas; Mustapha Raihane

doi:10.1080/10601325.2010.506107

Novel copolymers of 4-fluorostyrene. 2. Alkoxy ring-substituted 2-phenyl-1,1-dicyanoethylenes

Gregory B. Kharas, Emi Hanawa, Benjamin L. Hill, Katherine T. Flynn, Nikesh H. Bajaj, Yousef Bittar, Mathew R. Dow, Sean Moloney, Thuy A. Nguyen, Stuart A. Pitts, Christina A. Serret, Janeth Valadez, Ana C. Vallejo, Salima Atlas, Mustapha Raihane

Research output: Contribution to journal › Article › peer-review

2 Scopus citations

Abstract

Novel copolymers of trisubstituted ethylene monomers, alkoxy ring-substituted 2-phenyl-1,1-dicyanoethylenes, RC6H4CH = C(CN)2 (where R is 2-methoxy, 3-methoxy, 4-methoxy, 2-ethoxy, 3-ethoxy, 4-ethoxy, 4-propoxy, 4-buthoxy, 4-hexyloxy) and 4-fluorostyrene were prepared at equimolar monomer feed composition by solution copolymerization in the presence of a radical initiator (ABCN) at 70C. The composition of the copolymers was calculated from nitrogen analysis, and the structures were analyzed by IR, 1H and 13C-NMR. The order of relative reactivity (1/r1) for the monomers is 2-methoxy (1.5) 4-ethoxy (1.0) 4-methoxy (0.8) 3-ethoxy (0.7) = 3-methoxy (0.7) 4-hexyloxy (0.6) = 2-ethoxy (0.6) 4-butoxy (0.5) = 4-propoxy (0.5). High Tg of the copolymers, in comparison with that of poly(4-fluorostyrene) 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 284-500C range with residue (5-9% wt), which then decomposed in the 500-800C range.

Original language	English (US)
Pages (from-to)	973-976
Number of pages	4
Journal	Journal of Macromolecular Science - Pure and Applied Chemistry
Volume	47
Issue number	10
DOIs	https://doi.org/10.1080/10601325.2010.506107
State	Published - Oct 2010
Externally published	Yes

Keywords

4-fluorostyrene copolymers
radical copolymerization
Trisubstituted ethylenes

ASJC Scopus subject areas

Ceramics and Composites
Chemistry(all)
Polymers and Plastics
Materials Chemistry

Access to Document

10.1080/10601325.2010.506107

Cite this

Kharas, G. B., Hanawa, E., Hill, B. L., Flynn, K. T., Bajaj, N. H., Bittar, Y., Dow, M. R., Moloney, S., Nguyen, T. A., Pitts, S. A., Serret, C. A., Valadez, J., Vallejo, A. C., Atlas, S., & Raihane, M. (2010). Novel copolymers of 4-fluorostyrene. 2. Alkoxy ring-substituted 2-phenyl-1,1-dicyanoethylenes. Journal of Macromolecular Science - Pure and Applied Chemistry, 47(10), 973-976. https://doi.org/10.1080/10601325.2010.506107

Kharas, GB, Hanawa, E, Hill, BL, Flynn, KT, Bajaj, NH, Bittar, Y, Dow, MR, Moloney, S, Nguyen, TA, Pitts, SA, Serret, CA, Valadez, J, Vallejo, AC, Atlas, S & Raihane, M 2010, 'Novel copolymers of 4-fluorostyrene. 2. Alkoxy ring-substituted 2-phenyl-1,1-dicyanoethylenes', Journal of Macromolecular Science - Pure and Applied Chemistry, vol. 47, no. 10, pp. 973-976. https://doi.org/10.1080/10601325.2010.506107

@article{b9d4acc3418d49d98c20141f40a272cf,

title = "Novel copolymers of 4-fluorostyrene. 2. Alkoxy ring-substituted 2-phenyl-1,1-dicyanoethylenes",

abstract = "Novel copolymers of trisubstituted ethylene monomers, alkoxy ring-substituted 2-phenyl-1,1-dicyanoethylenes, RC6H4CH = C(CN)2 (where R is 2-methoxy, 3-methoxy, 4-methoxy, 2-ethoxy, 3-ethoxy, 4-ethoxy, 4-propoxy, 4-buthoxy, 4-hexyloxy) and 4-fluorostyrene were prepared at equimolar monomer feed composition by solution copolymerization in the presence of a radical initiator (ABCN) at 70C. The composition of the copolymers was calculated from nitrogen analysis, and the structures were analyzed by IR, 1H and 13C-NMR. The order of relative reactivity (1/r1) for the monomers is 2-methoxy (1.5) 4-ethoxy (1.0) 4-methoxy (0.8) 3-ethoxy (0.7) = 3-methoxy (0.7) 4-hexyloxy (0.6) = 2-ethoxy (0.6) 4-butoxy (0.5) = 4-propoxy (0.5). High Tg of the copolymers, in comparison with that of poly(4-fluorostyrene) 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 284-500C range with residue (5-9% wt), which then decomposed in the 500-800C range.",

keywords = "4-fluorostyrene copolymers, radical copolymerization, Trisubstituted ethylenes",

author = "Kharas, {Gregory B.} and Emi Hanawa and Hill, {Benjamin L.} and Flynn, {Katherine T.} and Bajaj, {Nikesh H.} and Yousef Bittar and Dow, {Mathew R.} and Sean Moloney and Nguyen, {Thuy A.} and Pitts, {Stuart A.} and Serret, {Christina A.} and Janeth Valadez and Vallejo, {Ana C.} and Salima Atlas and Mustapha Raihane",

note = "Funding Information: We thank the National Science Foundation Polymer Program (DMR-0710520) for support. We are grateful to acknowledge that the project is partly supported by the Coatings Industry Education Foundation, Chicago Society of Coating Technology and Office of Sponsored Programs and Research of DePaul University. We are grateful that the project is supported by the CNRST of Morocco for the framework of cooperation Morocco-USA in the field of Materials (n◦ 87/2007: Materials World Network).",

year = "2010",

month = oct,

doi = "10.1080/10601325.2010.506107",

language = "English (US)",

volume = "47",

pages = "973--976",

journal = "Journal of Macromolecular Science - Pure and Applied Chemistry",

issn = "1060-1325",

publisher = "Taylor and Francis Ltd.",

number = "10",

}

TY - JOUR

T1 - Novel copolymers of 4-fluorostyrene. 2. Alkoxy ring-substituted 2-phenyl-1,1-dicyanoethylenes

AU - Kharas, Gregory B.

AU - Hanawa, Emi

AU - Hill, Benjamin L.

AU - Flynn, Katherine T.

AU - Bajaj, Nikesh H.

AU - Bittar, Yousef

AU - Dow, Mathew R.

AU - Moloney, Sean

AU - Nguyen, Thuy A.

AU - Pitts, Stuart A.

AU - Serret, Christina A.

AU - Valadez, Janeth

AU - Vallejo, Ana C.

AU - Atlas, Salima

AU - Raihane, Mustapha

N1 - Funding Information: We thank the National Science Foundation Polymer Program (DMR-0710520) for support. We are grateful to acknowledge that the project is partly supported by the Coatings Industry Education Foundation, Chicago Society of Coating Technology and Office of Sponsored Programs and Research of DePaul University. We are grateful that the project is supported by the CNRST of Morocco for the framework of cooperation Morocco-USA in the field of Materials (n◦ 87/2007: Materials World Network).

PY - 2010/10

Y1 - 2010/10

N2 - Novel copolymers of trisubstituted ethylene monomers, alkoxy ring-substituted 2-phenyl-1,1-dicyanoethylenes, RC6H4CH = C(CN)2 (where R is 2-methoxy, 3-methoxy, 4-methoxy, 2-ethoxy, 3-ethoxy, 4-ethoxy, 4-propoxy, 4-buthoxy, 4-hexyloxy) and 4-fluorostyrene were prepared at equimolar monomer feed composition by solution copolymerization in the presence of a radical initiator (ABCN) at 70C. The composition of the copolymers was calculated from nitrogen analysis, and the structures were analyzed by IR, 1H and 13C-NMR. The order of relative reactivity (1/r1) for the monomers is 2-methoxy (1.5) 4-ethoxy (1.0) 4-methoxy (0.8) 3-ethoxy (0.7) = 3-methoxy (0.7) 4-hexyloxy (0.6) = 2-ethoxy (0.6) 4-butoxy (0.5) = 4-propoxy (0.5). High Tg of the copolymers, in comparison with that of poly(4-fluorostyrene) 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 284-500C range with residue (5-9% wt), which then decomposed in the 500-800C range.

AB - Novel copolymers of trisubstituted ethylene monomers, alkoxy ring-substituted 2-phenyl-1,1-dicyanoethylenes, RC6H4CH = C(CN)2 (where R is 2-methoxy, 3-methoxy, 4-methoxy, 2-ethoxy, 3-ethoxy, 4-ethoxy, 4-propoxy, 4-buthoxy, 4-hexyloxy) and 4-fluorostyrene were prepared at equimolar monomer feed composition by solution copolymerization in the presence of a radical initiator (ABCN) at 70C. The composition of the copolymers was calculated from nitrogen analysis, and the structures were analyzed by IR, 1H and 13C-NMR. The order of relative reactivity (1/r1) for the monomers is 2-methoxy (1.5) 4-ethoxy (1.0) 4-methoxy (0.8) 3-ethoxy (0.7) = 3-methoxy (0.7) 4-hexyloxy (0.6) = 2-ethoxy (0.6) 4-butoxy (0.5) = 4-propoxy (0.5). High Tg of the copolymers, in comparison with that of poly(4-fluorostyrene) 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 284-500C range with residue (5-9% wt), which then decomposed in the 500-800C range.

KW - 4-fluorostyrene copolymers

KW - radical copolymerization

KW - Trisubstituted ethylenes

UR - http://www.scopus.com/inward/record.url?scp=77956362789&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=77956362789&partnerID=8YFLogxK

U2 - 10.1080/10601325.2010.506107

DO - 10.1080/10601325.2010.506107

M3 - Article

AN - SCOPUS:77956362789

SN - 1060-1325

VL - 47

SP - 973

EP - 976

JO - Journal of Macromolecular Science - Pure and Applied Chemistry

JF - Journal of Macromolecular Science - Pure and Applied Chemistry

IS - 10

ER -

Novel copolymers of 4-fluorostyrene. 2. Alkoxy ring-substituted 2-phenyl-1,1-dicyanoethylenes

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this