Exploration of cardanol-based phenolated and epoxidized resins by size exclusion chromatography and MALDI mass spectrometry

• Phenolated and epoxidized cardanol-based resins were analyzed by SEC and MS.
• A nomenclature was proposed for the main products of both resins.
• Unsaturation patterns of cardanol-based species were simulated.
• Comparison of simulated and detected unsaturation pattern provided insight into the changes induced by the chemical treatments.
• SEC peaks convolution and MALDI artifacts were evidenced by SEC–MALDI off line coupling.

Cardanol and cardanol derivatives are among the most important biobased materials currently investigated in green chemistry, as renewable and promising building blocks in lieu of traditional raw materials from non renewable resources, in particular owing to the olefinic linkages on the C15 alkyl side-chain. Despite the increasing interest they arouse, analytical chemistry dedicated to cardanol and associated resins has been rarely reported in the literature, found even poorer when dealing with chromatography and mass spectrometry. In this work, a thorough molecular characterization was conducted using matrix assisted laser desorption ionization (MALDI) mass spectrometry, size exclusion chromatography (SEC), and SEC–MALDI coupling to gain insights into the composition of phenolated, epoxidized, and epoxidized phenolated cardanol. A nomenclature was proposed to properly describe the numerous species found in these materials, while simulations of the unsaturation patterns and their comparison with the detected patterns in MALDI-MS gave useful details about the phenolation treatment expected to occur on the polyunsaturated C15 side chain. Finally, the SEC–MALDI off-line coupling allowed SEC peaks to be deconvoluted by mass spectrometry and MALDI artefacts related to matrix adduction to be pointed out.

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