If your chain really has O rings then its outdated... try the new X rings...
Oil acts to lower a chains operating temp... lower temps means more
chain life... and if some of that oil finds its way down into the
rollers then you will arrest wear... if not your chain is ready for
replacement after the 3rd adjustment or about 8 to 12K miles depending
on HP...
The rings you think are made of rubber are actually made of a highly
fluorinated fluoroelastomer known commercially as Viton or Kalrez...
very tough stuff... they do not require oil to remain supple... when I
say the X ring has a excellent resistance to most chemicals including
sulfur... sulfur chloride... sulfur dioxide... sulfur hexaflouride to
name a few... that resistance means it does not soak up oil...
You are not required to lube the O rings in your fuel injection
system... your fuel tank... your dip stick and they stay supple
through out the life of the bike because they are very tough stuff...
The X rings can live through the life of a chain without any external lube...
I only recommend lube at the arrows in a effort that some of it will
reach the inside of the roller... I don't recommend lube at the X rings...