Synthesis of Functionalized Liquid Rubbers from Polyisoprene Full article
| Journal |
Journal of Applied Polymer Science
ISSN: 0021-8995 , E-ISSN: 1097-4628 |
||
|---|---|---|---|
| Output data | Year: 2009, Volume: 114, Number: 2, Pages: 1241-1249 Pages count : 9 DOI: 10.1002/app.29637 | ||
| Tags | Functionalization of polymers, Natural rubber, Nitrous oxide, Oligomers, Polyisoprene | ||
| Authors |
|
||
| Affiliations |
|
Funding (1)
| 1 | Russian Foundation for Basic Research | 06-03-08156 |
Abstract:
Noncatalytic transformation of cis-1,4-polyisoprene rubber (Mn = 320,000) into functionalized liquid rubbers containing various amounts of carbonyl groups was studied. The process is performed via selective carboxidation of the polymer C[DOUBLE BOND]C bonds by nitrous oxide (N2O) in the temperature range of 180–230°C and under 3–6 MPa pressure. The carboxidation proceeds by the nonradical type mechanism involving the 1,3-dipolar cycloaddition of N2O to the C[DOUBLE BOND]C bond. The main route of the reaction (ca. 65%) proceeds without cleavage of the internal C[DOUBLE BOND]C bonds and leads to the formation of ketone groups in the polymer backbone. The second route (ca. 35%) includes the cleavage of C[DOUBLE BOND]C bonds, yielding the molecules of a smaller size. This route results in a manifold decrease of the molecular weight, which, depending on the carboxidation degree, may be more than two orders of magnitude less than that of the parent rubber. A series of functionalized liquid rubbers having Mn value from 1000 to 19,000, and the oxygen content from 0.3 to 3.9 wt % was obtained in the form of the liquid unsaturated polyketones. Similar polyketones can also be prepared by carboxidation of the natural rubber.
Cite:
Dubkov K.A.
, Semikolenov S.V.
, Ivanov D.P.
, Babushkin D.E.
, Matsko M.A.
, Panov G.I.
Synthesis of Functionalized Liquid Rubbers from Polyisoprene
Journal of Applied Polymer Science. 2009. V.114. N2. P.1241-1249. DOI: 10.1002/app.29637 WOS Scopus РИНЦ ANCAN OpenAlex
Synthesis of Functionalized Liquid Rubbers from Polyisoprene
Journal of Applied Polymer Science. 2009. V.114. N2. P.1241-1249. DOI: 10.1002/app.29637 WOS Scopus РИНЦ ANCAN OpenAlex
Dates:
| Submitted: | Feb 2, 2008 |
| Accepted: | Nov 1, 2008 |
| Published online: | Jun 18, 2009 |
| Published print: | Oct 15, 2009 |
Identifiers:
| Web of science: | WOS:000268898300071 |
| Scopus: | 2-s2.0-67651006361 |
| Elibrary: | 13600135 |
| Chemical Abstracts: | 2009:848932 |
| Chemical Abstracts (print): | 151:338951 |
| OpenAlex: | W2158445642 |