These things have a way of cropping up.
Your design works even without the lettering. I'll just not worry about most of the text that are too faint then.
I have never used a resin printer (if this is what you printed with).
I was under the impression that overhangs would be less of a problem in liquid resin. That it creates neutral buoyancy. But that's just an assumption.
Printhead collisions would be even less of a problem if a whole layer is being lit at once.
It seems like those are not your problems? You mentioned clogging - but doesn't that have to do with heated extruders?
I'm trying to understand what you mean by pooling. Is liquid resin being attracted to the hardened cured crevices because of capillary action, and lensing the UV light?
If the resin composition is giving you trouble, try switching to Siraya Blu resin. I'm hearing good things about it.
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Resin printers are outside of my experience. So anything I say about it is just throwing ideas out there.
Your other problems though are familiar to me. And I can give experiential advice about it:
Watch this person try to slide a sleeve from a box.
It's parallel, so it should slide easily. But it's actually very difficult. Slight angle variance, and surface friction, combine to grip the sleeve in place.
Almost none of the plastic items you find have flat sides that are exactly perpendicular to a table surface. Where the shells diverge at a middle seam, they slope away from each other. Every shell has a trapezoid cross section which makes it easier to demold. Like when you stack or pull apart nesting bins. This is called "draft angle". Industry practice is to set the draft angle at 2 degrees. Although it's possible to go as small as 0.5 degrees. Your mold might tear less if you apply draft angles to the sides of your text.
When molding, pour your combined resin mix from one cup into another. This separates the unmixed portion stuck to the bottom of the first cup.
Put a third empty cup, or your mold, on the ground. Hold the filled second cup high. Pour in a thin stream. What this does is stretch out the liquid, and helps to eliminate bubbles.
This technique is taught by Smooth-On.
A vacuum chamber only shrinks bubbles. Not all of them will rise to the surface. They need to be shaken free by holding a vibrating device against the mold. This is why concrete vibrators exist. It might help to support your mold on upholstery foam while doing so.
A better way would be to place your mold on a vibrating table; maybe with the vacuum chamber too. To make sure they don't rattle apart, brace the mold within the vacuum chamber, and strap the vacuum chamber to the vibrating table.
One thing I'd like to add to my shop is a vibrating table to help reduce trapped bubbles when making molds or casting.
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