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Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis01:13

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Hydrolysis of esters under acidic conditions proceeds through a nucleophilic acyl substitution. In the presence of excess water, the reaction proceeds in a reversible manner, forming carboxylic acids and alcohols.
During hydrolysis, the ester is first activated towards nucleophilic attack through the protonation of the carboxyl oxygen atom by the acid catalyst. The protonation makes the ester carbonyl carbon more electrophilic. In the next step, water acts as a nucleophile and adds to the...
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Related Experiment Video

Updated: Jun 23, 2026

Surface Functionalization of Metal-Organic Frameworks for Improved Moisture Resistance
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Surface Functionalization of Metal-Organic Frameworks for Improved Moisture Resistance

Published on: September 5, 2018

Water-Based Polyurethane Dispersions: New Insights into the Intrinsic Stabilization Using Carboxylate Groups.

Christoph Grau1, Annette M Schmidt2, Jan Wilkens1

  • 1Faculty of Applied Natural Sciences, TH Köln-University of Applied Science, Leverkusen D-51379, Germany.

Langmuir : the ACS Journal of Surfaces and Colloids
|June 21, 2026
PubMed
Summary

Dimethylolpropionic acid (DMPA) content and incorporation timing influence water-based polyurethane dispersion (PUD) stability. Early DMPA addition affects charge distribution but not overall stability, with polyol type significantly impacting critical coagulation concentration.

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Area of Science:

  • Polymer Chemistry
  • Materials Science
  • Colloid Science

Background:

  • Water-based polyurethane dispersions (PUDs) require ionizable groups like dimethylolpropionic acid (DMPA) for stability.
  • DMPA's pH-dependent dissociation influences electrostatic repulsion between PUD particles.
  • Understanding the structure-stability relationship is crucial for optimizing PUD performance.

Purpose of the Study:

  • To investigate the structure-stability relationship in PUDs with varying soft segments and DMPA content.
  • To analyze the dissociation behavior of carboxyl groups and particle charge.
  • To evaluate dispersion stability using critical coagulation concentration (ccc) and theoretical models.

Main Methods:

  • Synthesis of PUDs with different polyols (polyether, polyester, polycarbonate) and DMPA content via the acetone process.
  • Potentiometric acid-base titration to characterize carboxyl group dissociation and particle charge.
  • Electrokinetic measurements and hard particle theory to determine surface potentials.
  • DLVO and XDLVO theory for dispersion stability analysis.
  • Contact angle measurements and van Oss-Chaudhury-Good theory for Hamaker constants.

Main Results:

  • Potentiometric titration may not detect all incorporated carboxyl groups, suggesting hindered dissociation and nonuniform charge distribution.
  • Titration curves fit best with at least two functional groups of different acid strengths.
  • Early DMPA incorporation increases internal charge groups but minimally impacts surface potential and stability.
  • Surface potentials decrease slightly with increasing DMPA content due to smaller particle size.
  • Critical coagulation concentration (ccc) increases with DMPA content and is strongly influenced by the polyol component.

Conclusions:

  • The dissociation of DMPA in PUDs is complex, involving multiple acid strengths and potentially hindered dissociation.
  • While early DMPA incorporation affects internal charge localization, it does not significantly alter overall dispersion stability or surface potential.
  • The polyol component plays a critical role in PUD dispersion stability, necessitating extensions to the DLVO theory to include hydrophobic interactions.