What materials are available to make a watertight penetration through the top of a concrete pull box for a vertical run of cable tray? In practice, is it preferable to use PVC conduit with rubber pipe sleeves?
The pull box will be situated under a raised GIS building on the Gulf Coast and buried. Ideally, we would like to go straight up through the lid to a building floor penetration.
Sealing the cables individually with pressure fit seals is the only way you're likely to get a truly watertight penetration in the circumstance. As Waross noted their preference, almost any vertical cable entry is extremely difficult to seal.
Roxtec is similar to Hawke and much more prevalent in the USA. It works if you you can set it up properly. I have never come across a properly installed Roxtec transit in the wild. It's no fun working with these transit systems in vertical transits. All of these systems are expensive.
Another option is to build a dam around the wire penetrations and fill it with a flowable silicone like Dow Corning 734. You'll have to get it tight enough so the silicone doesn't flow out before it cures but 734 gets in all of the crevices and does a really good job sealing.
Concrete pull box, Gulf Coast? - my experience is that no mater what you do underground power distribution in waterfront locations stays wet. The cable, elbow connectors, etc can be ordered rated for submergence, then the fact that vertical penetrations out of the concrete pull box can not be sealed perfectly is less of a problem.