Two times Soulless!Sam helped Dean, even when there was nothing in it for him. It’s interesting because SS felt no emotional connection to Dean. He stayed with him because they were partners, in a way, so he worked with him but beyond that, there was no loyalty or love. But here we see two examples of him going out of his way to help and save Dean. It seems to me that even though he couldn’t feel his deeply rooted loyalty to Dean, it was still there somewhere.