One other thing to think about (as if you do not have enough already !):

when working with plant extracts I once had a back pressure problem that was due to deposits in the narrow bore tube between injector and column. When I changed to a wider bore tube the problem went away completely. The only explanation I could think of was that some macromolecules in the extract were unravelling due to the very high laminar shear in the tube (at 1 ml/min the linear flow is meters/s) and then cross linking with one another.

Could this be happening here at the head of the column. If it is you could protect your column by sacrificing another component with whatever hydraulic property of the column (e.g. frit pore size) it is that is causing the deposit.

Peter