Alkenylsuccinic anhydrides
class of chemical compounds
Alkenyl succinic anhydrides (ASA) are derivatives of succinic anhydrides. One H of the succinic anhydride ring is replaced with an iso-alkenyl chain (C14 to C22). ASA's are colorless and usually viscous liquids. They are widely used, especially in surface sizing of paper, paperboard, and cardboard, as well as in the hydrophobicization of cellulose fibers. Products treated with it show reduced penetration of aqueous media, such as inks or drinks (like milk or fruit juices).
In terms of their mode of action, the anhydride is proposed to react with the hydroxyl groups on the cellulose, forming an ester. The alkenyl side-chain modifies the surface properties of the paper product. The application is similar to that for alkyl ketene dimers. In the United States alkenylsuccinic anhydrides are the preferred paper sizing agents, whereas in Europe, alkyl ketene dimers (AKDs) predominate.
History
The reaction of maleic anhydride (MA) with aliphatic monounsaturated n- and iso-alkenes was described as early as 1936 in a patent.
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