If the file already exists / existed in TS with the proper EAs and then is copied over (by import or other process) - I believe the original EAs remain intact (you should be able to easily test this theory)
Instead of sending it out, are you able to make any calls to the translator? Either via a simple javascript or perl http request in which you send out the data. Or some other method of making a connection to the translator to get the data for your fields in the DCR. You could do this on save, on change, or with a callout button, etc.
There is also an OOTB translate workflow in 7.2.1