Pencil and Paper Estimation of Hansen Solubility Parameters

Abstract

Simple procedures to estimate Hansen solubility parameter (HSP) components from structural formulas are investigated. The best results are obtained using a simple relationship with molar volume and refractivity for the dispersion component, and using additivity models based on tailored fragments specifically designed for the polar and hydrogen bonding components. Despite large errors for some classes of chemicals, including small inorganic molecules, ionic liquids, and high halogen compounds, these models yield average absolute deviations from reference on par with state-of-the-art models and lower than reported using molecular dynamics simulations or nonlinear quantitative structure–property relationship models based on a limited set of quantum chemical descriptors. In contrast to group contribution methods that are either more restricted in scope or heavily parameterized, they are thoroughly validated and very easy to apply. Furthermore, the errors observed are easy to rationalize and may usually be anticipated. This work sheds light on some limitations inherent to pure additivity approaches for HSP prediction and provides a first step toward better models. A Python script implementing the procedure and the fully detailed results are provided as the Supporting Information.

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“…HSP is expressed as “ δ ”, and its international standard unit is “MPa”. Based on the different groups with different contributing components, the HSP of the compound is calculated by the group contribution method, the calculation formula is as follows [ 18 , 22 , 23 , 24 ]: …”

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“…The solubility parameters of the compounds were calculated based on the Mathieu method. 47 The authors developed a simple method to estimate Hansen parameter solubilities. The HSP values corresponding to dispersion forces (δD), dipole interaction (δP), and hydrogen bonding (δd, δp, and δh, respectively) for solvents, cellulose, and blocking agents were obtained using group contribution calculations.…”

“…The solubility parameters of the compounds were calculated based on the Mathieu method . The authors developed a simple method to estimate Hansen parameter solubilities.…”

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“…The approach to derive HSP data for each of the studied OPEs, which was not available in the literature, is described in detail in the Supporting Information . In brief, models were developed using partial least squares regression 34 with HSP data for 71 similar compounds from the literature 35 (see Supporting Information ) and a set of 65 calculated molecular descriptors (MOE 36 ) that had been used in previous studies. 27 , 37 , 38 These models were applied to predict HSP parameters for the studied OPEs ( Table S2 ).…”

“…The approach to derive HSP data for each of the studied OPEs, which was not available in the literature, is described in detail in the Supporting Information. In brief, models were developed using partial least squares regression with HSP data for 71 similar compounds from the literature (see Supporting Information) and a set of 65 calculated molecular descriptors (MOE) that had been used in previous studies. ,, These models were applied to predict HSP parameters for the studied OPEs (Table S2). D HSP was then calculated to provide a rough estimate of the solubility of each OPE in the studied polymer films following the equation , where δ D1 , δ P1 , and δ H1 are the HSP values for polymers, and δ D2 , δ P2 , and δ H2 are the HSP values for OPEs.…”