from datetime import datetime,timedelta
import time
startdate = '09:00:00.499'
end = '15:23:20'
i = 0.5
while True:
date = (datetime.strptime(startdate, '%H:%M:%S.%f') + timedelta(seconds=i)).strftime('%H:%M:%S.%f')
end_time = date.replace(':','')[:-3]
print(end_time)
i+=0.5
if date >= end:
break