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@absurdbird
^ I was going to guess at late 40's early fifties for the white bike and a few years later for the green -based mainly on trademarks etc
The basic design is the same as the Cyclo which was used since forever (20's) but Simplex mechs had a return spring.
Simplex made a very similar derailleur in the late 30's but with a straighter mounting bracket which mounted further along the chainstay called the Route, they produced the same derailleurs for many years with small changes to the design.
Show us some more of the bikes.
RVL, where did you get the patent apps from? -really cool.