I have a copy of a songbook entitled "The Sentinel Orange and Patriotic Song Book".Orders were to be sent to "The Sentinel",37-41 McCaul Street, Toronto,Ontario (no postal code, well before those).It is undated and is full of patriotic and orange songs.On the back page is written "ORANGEMEN-WHAT OF THE FUTURE!" I would venture a guess that the book was probably published sometime in the 30s or 40s.