Jump to main content
Jump to site search

Issue 18, 2010
Previous Article Next Article

Halogen-free, low flammability polyurethanes derived from deoxybenzoin-based monomers

Author affiliations

Abstract

Two novel deoxybenzoin-containing monomers, a diisocyanate and a diol, were synthesized and used to prepare polyurethane materials and foams. 4,4′-Diaminodeoxybenzoin was prepared by Ullmann coupling of 4,4′-dibromobenzil with tert-butyl carbamate. Reduction of one of the carbonyl groups, and t-Boc deprotection, gave the aromatic diamine, which was converted to 4,4′-deoxybenzoin diisocyanate (DBDI) with triphosgene. DBDI was then used to prepare two different polyurethanes, one by reaction with 1,3-propanediol, and the other by reaction with deoxybenzoin diol. The polyurethanes obtained from these reactions displayed low heat release capacity (HRC) values relative to conventional polyurethanes prepared from 4,4′-methyldiphenyl diisocyanate (MDI) and 2,4-toluene diisocyanate (TDI). Polyurethanes prepared in this study displayed HRC values as low as ∼130 J g−1 K−1, and char yields as high as ∼40%. In addition, deoxybenzoin-based oligomers containing hydroxyl end groups were also synthesized and used to prepare polyurethane foams that displayed markedly lower HRC values, and higher char yields, than conventional polyurethane foams, which burn readily and drip. Taken together, the integration of deoxybenzoin moieties into the diisocyanate or polyol component of the polymer structure is found to lower heat release rates and reduce flammability in the absence of any added flame retardant, such as halogenated compounds that represent health and environmental hazards.

Graphical abstract: Halogen-free, low flammability polyurethanes derived from deoxybenzoin-based monomers

Back to tab navigation

Article information


Submitted
09 Dec 2009
Accepted
08 Feb 2010
First published
08 Mar 2010

J. Mater. Chem., 2010,20, 3681-3687
Article type
Paper

Halogen-free, low flammability polyurethanes derived from deoxybenzoin-based monomers

T. Ranganathan, P. Cossette and T. Emrick, J. Mater. Chem., 2010, 20, 3681 DOI: 10.1039/B924034A

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.


Search articles by author

Spotlight

Advertisements