I could also be wrong, but I believe SDS has less ‘affinity’ for protons than acetic acid (which is part of the reason why detergents work so well). You’d need sulfuric acid, or something stronger, and removal from solution of its buddy ion sodium. Then I think you could protonate dodecyl sulfate.

Now acetic acid and soaps…yeah, far more likely to generate scum. The polar head is a weaker acid.

The importance of soap to human civilization is documented by history, but some problems associated with its use have been recognized. One of these is caused by the weak acidity (pKa ca. 4.9) of the fatty acids. Solutions of alkali metal soaps are slightly alkaline (pH 8 to 9) due to hydrolysis. If the pH of a soap solution is lowered by acidic contaminants, insoluble fatty acids precipitate and form a scum. A second problem is caused by the presence of calcium and magnesium salts in the water supply (hard water). These divalent cations cause aggregation of the micelles, which then deposit as a dirty scum.

These problems have been alleviated by the development of synthetic amphiphiles called detergents (or syndets). By using a much stronger acid for the polar head group, water solutions of the amphiphile are less sensitive to pH changes. Also the sulfonate functions used for virtually all anionic detergents confer greater solubility on micelles incorporating the alkaline earth cations found in hard water.

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