There is lots of weird sh!t going on in this thread.
I'm tempted to run a non-slip washer but after hearing about the bolts that are breaking off in the shaft it gave me pause.
Don't do it!
Using a soft metal washer against a hardened shaft will do nothing to stop the bolt backing out and will only ensure that the internal oil hole doesn't line-up anymore... creating a whole new set of problems with an unoiled drive chain.
The 272 loctite you used is slightly higher temperature and slightly higher strength than the 263 but is not oil resistant
24 hour cure for steel.
Chemical/Solvent Resistance Motor oil - at 87C -- 62% strength (I assume much worse at engine oil temperatures)
Rated for 230C (450F)
3 hour cure for steel (but hey, longer won't hurt)
Chemical/Solvent Resistance Motor oil 125C -- 75% strength after 5000 hours.
Rated for 180C (360F)
The 263 should be less likely to wash away in oil and should be a better choice for this bolt. As diligent as your application was, I think you simply used the wrong loctite.
7 day cure for steel
Chemical/Solvent Resistance Motor oil 125C -- >100% strength (this one gets stronger with heat)
Rated for 180C (356F)
Gives best resistance to dynamic, axial and radial loads. Recommended for retaining shafts, gears, pulleys, and similar cylindrical parts.
This one that
posted is interesting, being made for shafts, gears and pulleys and gets stronger with heat and oil. Maybe putting this on the shafts would keep the gears in place and negate the problem altogether?