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Any tips or methods for getting paint out of a spray can into a dropper bottle/ screw top jar? Without making the worlds largest mess or wasting paint? How long will it last once successfully transferred??

I've seen some people use straws to decant spray bottles. I've only ever decanted spray paint directly in to my airbrush, and I literally just sprayed it straight in to the paint cup from close range Did it in a spray booth with a strong exhaust fan to carry away the excess fumes.

Make sure you let the paint sit for a while before trying to put a cap on it because there'll be some propellant left in the paint that needs to slowly boil off.

Be aware that spray paints are more than likely going to have different solvents to normal out of the bottle paints, so they may not thin with whatever you thin bottled paints from the same manufacturer.

Tamiya has an article on decanting....

https://www.tamiyausa.com/articles/decanting-tamiya-spray-301#.WLLXAG996Uk

I actually didn't have any problems with outgassing when I sprayed directly in to my paint cup, it boiled for a few seconds then was fine, maybe because I didn't use a straw or tube or anything perhaps the propellant boiled off easier? Don't know. But if I were going to close the bottle I'd definitely wait a few hours before putting a cap on it.