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Silicone rubber usually only sticks to silicone rubber (what is usually used for the rubber roads).
I've used silicone caulking thinned with white spirit and mixed with oil paints to paint some of my stuff (which was donated to a former club from the days before digital cameras).
That technique came from friends who work in the FX modelling industry - because it's what they do. There are other ways to paint polyurethane rubbers, too.
It really depends on the type of rubber they are made from.
Latex, silicone or PU rubbers all take different techniques.
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