I'm not sure about the year for the "Ask Me"
buttons,but Dirty Dan the Carbon Man can be dated to the early to late thirty's. Pictures shown below are dated 1935,1936. I believe the Ask Me buttons are late thirtys to early fortys. Hi-Speed used the Carbon man around 1938 I believe on their maps.
Notice in last picture Dirty Dan "steals power" Carbon Conquered with Super Solvenized Woco Pep.Dirty Dan's done!