A chemically functional phosphorus version of natural rubber

July 10, 2017, Wiley
A chemically functional phosphorus version of natural rubber

Goodyear's 1839 discovery of the vulcanization of natural rubber obtained from rubber trees marks the beginning of the modern rubber industry. A variety of synthetic rubber products were subsequently developed. In the journal Angewandte Chemie, scientists have now introduced a new, interesting variant: a phosphorus-containing rubber with a structure that corresponds to that of natural rubber.

The similar properties of double bonds between carbon atoms (C=C) and phosphorus–carbon double bonds (P=C) led to the idea to try general polymerization techniques on the latter. After a number of successful attempts, researchers working with Derek P. Gates at the University of British Columbia (Vancouver, Canada) wanted to apply this concept to molecules that contain both P=C and C=C double bonds: phosphorus analogs of the building block of , isoprene (2-methylbuta-1,3-diene) and its close relative, 1,3-butadiene.

Starting with phosphorus-containing precursors, the team was able to synthesize the first examples of poly(1-phospha-isoprene) and poly(1-phospha-1,3-butadiene). Precise characterization with a variety of spectrometric techniques gave some insight into the molecular structures of the resulting polymers. Like in the polymerization of isoprene and related dienes (compounds with two carbon-carbon double bonds), one of the double bonds in each building block is retained. The polymerization mainly occurs through the C=C double bonds and only a tiny proportion happens at the P=C double bonds. This means that only a few are incorporated into the polymer backbone. The majority of the phosphorus atoms form side chains in which the P=C are maintained, leaving them available for further reactions or alterations to the polymers.

"Our functional phosphorus-containing materials are rare examples of polymers containing phosphaalkene moieties and offer many prospects for further derivatization and crosslinking," according to Gates. For example, the researchers were able to bind to the polymers. "As a macromolecular ligand for gold ions, the new polymers may be of future interest in catalysis and nanochemistry. Furthermore, the successful polymerization of P=C/C=C hybrid monomers opens the door to incorporate P-functionalities into commercial rubbers such as butyl rubber or styrene-butadiene rubber that traditionally use isoprene or butadiene comonomers. Such new copolymers promise unique architectures, properties, and functionality when compared to their carbon-only analogues."

Explore further: Clue for efficient usage of low-cost nickel catalysts

More information: Klaus Dück et al. Polymerization of 1-Phosphaisoprene: Synthesis and Characterization of a Chemically Functional Phosphorus Version of Natural Rubber, Angewandte Chemie International Edition (2017). DOI: 10.1002/anie.201703590

Related Stories

Clue for efficient usage of low-cost nickel catalysts

May 24, 2016

A group of researchers at Osaka University developed a method of the consecutive formation of bonds of two butadiene, alkyl groups, and benzene rings by using a cheap nickel catalyst. Using this technique, it has become possible ...

Biodegradable polymers made by chemical vapor deposition

December 1, 2016

Polymerization by chemical vapor deposition (CVD) is a simple method for modifying surfaces by which topologically challenging substrates can be evenly coated with polymers. In the journal Angewandte Chemie, researchers have ...

Recommended for you

Research gives new ray of hope for solar fuel

April 24, 2018

A team of Renewable Energy experts from the University of Exeter has pioneered a new technique to produce hydrogen from sunlight to create a clean, cheap and widely-available fuel.

New theory shows how strain makes for better catalysts

April 20, 2018

Brown University researchers have developed a new theory to explain why stretching or compressing metal catalysts can make them perform better. The theory, described in the journal Nature Catalysis, could open new design ...

Machine-learning software predicts behavior of bacteria

April 19, 2018

In a first for machine-learning algorithms, a new piece of software developed at Caltech can predict behavior of bacteria by reading the content of a gene. The breakthrough could have significant implications for our understanding ...

0 comments

Please sign in to add a comment. Registration is free, and takes less than a minute. Read more

Click here to reset your password.
Sign in to get notified via email when new comments are made.