Novel Copolymers of Styrene. 15. Phenoxy Ring-Substituted Methyl 2-Cyano-3-Phenyl-2-Propenoates
Electrophilic trisubstituted ethylenes, phenoxy ring-substituted methyl 2-cyano-3-phenyl-2-propenoates, RPhCH=C(CN)CO 2 CH 3 , where R is 4-(4-BrC 6 H 5 O), 2-(4-ClC 6 H 5 O), 3-(4-ClC 6 H 5 O), 4-(3-ClC 6 H 5 O), 4-(4-ClC 6 H 5 O), 4-(4-FC 6 H 5 O), 2-(3-CH 3 OC 6 H 5 O), 2-(4-CH 3 OC 6 H 5 O), 3-(...
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| Published in: | Journal of macromolecular science. Part A, Pure and applied chemistry Vol. 51; no. 9; pp. 683 - 688 |
|---|---|
| Main Authors: | , , , , , , , , , , , , |
| Format: | Journal Article |
| Language: | English |
| Published: |
Colchester
Taylor & Francis
01-01-2014
|
| Subjects: | |
| Online Access: | Get full text |
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| Summary: | Electrophilic trisubstituted ethylenes, phenoxy ring-substituted methyl 2-cyano-3-phenyl-2-propenoates, RPhCH=C(CN)CO
2
CH
3
, where R is 4-(4-BrC
6
H
5
O), 2-(4-ClC
6
H
5
O), 3-(4-ClC
6
H
5
O), 4-(3-ClC
6
H
5
O), 4-(4-ClC
6
H
5
O), 4-(4-FC
6
H
5
O), 2-(3-CH
3
OC
6
H
5
O), 2-(4-CH
3
OC
6
H
5
O), 3-(4-CH
3
OC
6
H
5
O), 4-(4-CH
3
OC
6
H
5
O), 3-(4-CH
3
C
6
H
5
O) were prepared and copolymerized with styrene. The monomers were synthesized by the piperidine catalyzed Knoevenagel condensation of phenoxy ring-substituted benzaldehydes and methyl cyanoacetate, and characterized by CHN analysis, IR,
1
H and
13
C-NMR. All the ethylenes were copolymerized with styrene (M
1
) 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 IR,
1
H and
13
C-NMR. The order of relative reactivity (1/r
1
) for the monomers is 4-(4-CH
3
OC
6
H
5
O) (6.07) > 3-(4-ClC
6
H
5
O) (3.38) > 3-(4-CH
3
OC
6
H
5
O) (2.78) > 4-(3-ClC
6
H
5
O) (2.77) > 2-(4-ClC
6
H
5
O) (2.29) > 3-(4-CH
3
C
6
H
5
O) (1.98) > 4-(4-FC
6
H
5
O) (1.92) > 4-(4-ClC
6
H
5
O) (1.89) > 2-(3-CH
3
OC
6
H
5
O) (1.39) > 2-(4-CH
3
OC
6
H
5
O) (0.90) > 4-(4-BrC
6
H
5
O) (0.77). Relatively high T
g
of the copolymers in comparison with that of polystyrene indicates a 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 (2.5-8.0% wt), which then decomposed in the 500-800°C range. |
|---|---|
| Bibliography: | ObjectType-Article-2 SourceType-Scholarly Journals-1 ObjectType-Feature-1 content type line 23 ObjectType-Article-1 ObjectType-Feature-2 |
| ISSN: | 1060-1325 1520-5738 |
| DOI: | 10.1080/10601325.2014.936229 |