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Many of us have experienced the failure of nitrile gloves when exposed to chloroform. What's going on at a mechanistic level when this occurs?

I would guess that the chloroform dissolves some of the polymer into its constituent monomers, but I've never heard anything more definite than that. Is it a similar mechanism to what happens when chloroform is left too long in a plastic bottle?

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    $\begingroup$ +1 Interesting question. If the chloroform does dissolve the polymer, it most probably does not depolymerize it. I think dissolution is much more probable than depolymerization. $\endgroup$ – CHM Apr 26 '12 at 3:29
  • $\begingroup$ Its not a reaction. Its more like acetone and plastic. You get the plastic back when the acetone evaporates. $\endgroup$ – Kevin Kostlan May 11 '15 at 14:17
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Nitrile gloves are made of nitrile rubber, or poly(butadiene/acrylonitrile). This polymer is highly soluble in chloroform, with some papers I found indicating that one can dissolve up to 18% in mass of nitrile butadiene rubber in chloroform. Moreover, it permeates easily through NBR, meaning we can expect the dissolution to be fast in addition to thermodynamically favourable.

Finally, I would not expect the mechanism here to be any different from that of any polymer dissolution by a good solvent. The solvent will permeate through the polymer, intercalate between polymer chains, and solvate them (inducing swelling). Once solvated, the network of polymer chains looses its mechanical properties and they can fully separate. (I wish I could find a good existing illustration for that part, but I can't right now… If anyone can, feel free to edit!)

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Close but no cigar. It does dissolve the polymer, but certainly not into its constituent monomers. That would be one heck of a chemical reaction.

Make sure you choose the proper gloves for whatever you are working with.

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