Hi; The Listing for the Waterbury button Co, Conn is listed as having been in business from 1849 - 1965. The following is a Generalized breakdown of your buttons ok.:
TOP ROW:
#1 = Mass. State Seal Button = Modern
#5 = What was the 17th State admitted to the United States ?? Count the Stars. - This may be modern.
Answer: Ohio on March 1st, 1803. The Button may be a Commemorative Button this dating it to 1903.
https://en.wikipedia.org/wiki/Ohio
SECOND ROW:
#1 = WW2 Naval Officers shirt button
#2 = WW2 Naval Officers Coat Button
#3 = WW2 Naval Officers shirt button
#4 & 5 = Naval Officers shirt buttons = Modern
THIRD ROW :
#1 = WW2 Marines Coat Button
#2 = Naval Aviation Officers Coat Button
#4 = WW2 Enlisted Mans coat Button
FOURTH ROW:
#1 = WW2 Naval Officers Coat Button
#2 = WW1 Naval Officers Coat Button
I hope this clarifies your finds for you. The best button there I think is the WW1 Naval Officers Coat Button. Value: $15. The rest about $3 - $5 each. Good luck. Happy Hunting. PEACE:RONB