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@Mike[trampsparadise]
The problem lies in it being an 'old' shimano (JIS) crank. How worn is the spindle hole? If the JIS crank already sits further in on an ISO taper then an old crank just might bottom out with the crank bolt resting against the spindle instead of holding the crank on in tension. There's only one way to find out.
How long is the phil spindle? If you're using an old 600 crank then the ideal BB would be a shimano 107mm, I reckon a 110,112 symmetrical ISO BB would work on good condition cranks, on worn out cranks you could get away with as much as 115 but I wouldn't venture close to the 107mm mark.*
*of course with an adjustable phil this is only a guideline.