RE: Nylon Wing Bolts
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Without the proper education for assessing wear and damage over time, it might be a good idea to toss them occasionally.
We used to boil our nylon props for twenty minutes in order to rehydrate the nylon and restore some strength. Did it work? I don't know, but the props usually looked better afterwards. This might work for the nylon bolts too. Or it might not.
Ed Cregger
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I don't think there's any visual cues, other than the obvious, such as flattened threads or cracks.
Short of subjecting them to a stress test of some kind, or putting them under a microscope...I don't think there's a way anyone would ever know if a bolt is fatigued. Maybe I'm worried over nothing....but I guess they're cheap enough I don't really mind throwing them out occasionally.