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We describe an exploration of small molecules capable of suppressing the solubility of polymers with pendent carboxylic acid groups. We evaluate the use of small molecules such as alkyl amines, benzyl bromide, N,N’-dicyclohexylcarbodiimide (DCC) and N,N-diisopropylcarbodiimide (DIC). We have combined polymers containing carboxylic acids with these reagents and evaluated their changes in dissolution rate in n-butyl acetate and 0.26 N TMAH. We have also conducted model reactions of non-polymeric carboxylic acids in NMR tubes to help characterize the reactions occurring with polymers.
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Jacob Sitterly, Justin Nhan, Moira Niluxsshun, Stephen Smith, Robert L. Brainard, "Switching the solubility of polymers using intermolecular reactions and diffusion of small molecules," Proc. SPIE 12498, Advances in Patterning Materials and Processes XL, 124980V (30 April 2023); https://doi.org/10.1117/12.2659167