Sulfonation of a Polypentenamer and Preparation of Its Hydrogenated Derivatives

Abstract

Polypentenamer has been sulfonated using a 1: 1 complex of sulfur trioxide and triethyl phosphate in chloroform. A range of polymers containing from 1.9 to 19.1 mol % sulfonate groups was prepared by this reagent and isolated in the form of sodium salts. These materials are initially free from covalent cross-links but cross-linking occurs with aging unless the polymers are stabilized with a free-radical scavenger such as hydroquinone. The unsaturated bonds in these materials can be removed by hydrogenation with ptoluenesulfonyl hydrazide. The hydrogenated derivatives are crystalline and no longer require a stabilizer to inhibit cross-linking. Both the unsaturated and hydrogenated polymers are hydrophilic.

Structural Properties of Ionomers

“…These reactions can be carried out in solution or via reactive milling in an extruder. During the last decade, a novel ionic elastomer was developed based on a polypentenamer backbone (15)(16)(17)(18)(19)(20)(21). The starting poly pentenamer was prepared via ring-opening polymerization of cyclo pentane.…”

Polypentenamer Renaissance: Challenges and Opportunities

“…This strategy was the subject of extensive reports (hydrogenation, ionization, hydroformylation, etc.) through the 1970s. − Recently, Buchmeiser and co-workers performed hydrobromination and hydroboration chemistry on PCP along with further modifications (hydroxylation, amination, and grafting) to access functional polar olefins with a large range of glass transition temperature, T g , values (−45 to 50 °C) depending on the type and extent of functionality . Although an elegant and facile method for producing a variety of properties, precision topologies are lost due to the propensity for incomplete functionalization and nonregioselective alkene addition (Figure a).…”

Thermal and Dynamic Mechanical Properties of Sulfonated Polypentenamers

“…The sulfonated material was neutralized by precipitating the reaction mixture into a 0.25M solution of NaOH in ethanol. This reaction is described in detail elsewhere ( 5) and is summarized as follows:…”

“…We reported previously the modification of a PP by phosphonylation ( 1 ) and by the addition of thioglycolate side groups ( 2), and exam- ined the thermal and dynamic mechanical properties of the neutralized derivatives of these systems ( 3,4). Recently we were able to extend this series by preparing sulfonated PP's free of covalent cross-links, in the form of sodium salts ( 5). In this study we used thermal and dynamic mechanical techniques to investigate a range of the sulfonated materials containing up to four sulfonate groups per 100 backbone carbon atoms.…”