Ketonization of a Nitrile-Butadiene Rubber by Nitrous Oxide: Comparison with the Ketonization of Other Type Diene rubbers Full article
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European Polymer Journal
ISSN: 0014-3057 , E-ISSN: 1873-1945 |
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| Output data | Year: 2009, Volume: 45, Number: 12, Pages: 3355-3362 Pages count : 8 DOI: 10.1016/j.eurpolymj.2009.10.007 | ||
| Tags | Diene rubbers, Functional oligomers, Functional polymers, N2O, Nitrile-butadiene rubber, Polyketones | ||
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Abstract:
Noncatalytic ketonization of a nitrile-butadiene rubber (21 mol% acrylonitrile units) by nitrous oxide was shown to yield polymeric products functionalized with carbonyl (mainly ketone) groups. The reaction was conducted in a benzene solvent at 180–230° and pressure of 3–6 MPa. An assumed ketonization mechanism includes a 1,3-dipolar cycloaddition of N2O to Cdouble bond; length as m-dashC bonds in butadiene units.
According to the NMR and GPC data, the main route of the reaction (ca. 85%) proceeds without cleavage of the Cdouble bond; length as m-dashC bonds and yields ketone groups in the polymer backbone. The minor route (ca. 15%) includes the cleavage of Cdouble bond; length as m-dashC bonds resulting in fragmentation of the macromolecules that leads to a decrease in their molecular weight. The nitrile (–CN) groups remain untouched. The resulting product is a bifunctional low-molecular rubber containing, in addition to originally present nitrile groups, a regulated amount of new ketone groups randomly distributed along the polymer backbone.
The results for nitrile-butadiene rubber are compared with the earlier studied ketonization of butadiene and isoprene rubbers. The molecular structure of monomeric units was shown to be an important characteristic of a parent rubber affecting the reaction rate, degree of fragmentation, and consistency (rubber-like, plastic, or liquid) of the resulting material.
Cite:
Semikolenov S.V.
, Dubkov K.A.
, Ivanov D.P.
, Babushkin D.E.
, Matsko M.A.
, Panov G.I.
Ketonization of a Nitrile-Butadiene Rubber by Nitrous Oxide: Comparison with the Ketonization of Other Type Diene rubbers
European Polymer Journal. 2009. V.45. N12. P.3355-3362. DOI: 10.1016/j.eurpolymj.2009.10.007 WOS Scopus РИНЦ ANCAN OpenAlex
Ketonization of a Nitrile-Butadiene Rubber by Nitrous Oxide: Comparison with the Ketonization of Other Type Diene rubbers
European Polymer Journal. 2009. V.45. N12. P.3355-3362. DOI: 10.1016/j.eurpolymj.2009.10.007 WOS Scopus РИНЦ ANCAN OpenAlex
Dates:
| Submitted: | Jun 17, 2009 |
| Accepted: | Oct 4, 2009 |
| Published online: | Oct 13, 2009 |
| Published print: | Dec 1, 2009 |
Identifiers:
| Web of science: | WOS:000272871400005 |
| Scopus: | 2-s2.0-70449507042 |
| Elibrary: | 15301505 |
| Chemical Abstracts: | 2009:1448582 |
| Chemical Abstracts (print): | 152:146529 |
| OpenAlex: | W1969331179 |