20 years ago which refridgerant would have been used?
If starting again from no pressure would it work OK with the new gas?
I think the answer is "probably not" - or at least, not very well or for very long. Let's assume this is a car with R 134a as the refrigerant, rather than the older R12 (which has been banned since the early 1990s), or the current R1234YF. The problem with 134a is that the lubricating oil is fiercely hygroscopic and forms quite a corrosive fluid when mixed with water. The systems are designed with a cartridge of desiccant in them to remove all traces of water.
Although refrigerant will leak out slowly with time (say 5-10 years), and if that's the only problem, then putting some more gas in it will work fine, the most common cause of total refrigerant loss is a hole in the condenser. This is the second "radiator" that sits in front of the cooling system radiator, and gets pelted with stones and road grit, as well as salty water in winter. Once that happens, the refrigerant escapes, and you create a path for humidity to enter. This then saturates the desiccant. Once that's saturated, you get the corrosive liquid forming.
If I had a 20 year old car and wanted to get the aircon working again, I'd first try depressing the valves to see if there was
ANY positive pressure in there
AT ALL. If so, it would mean that there's a good chance water won't have entered the system. I'd then (without the engine running) put 12V on to the wire to the compressor clutch to see if I heard a "tick" as the clutch pulled in. I'd then apply a vacuum to the charging ports and see if the system could hold a vacuum for about half an hour. If it could, I'd buy a new receiver / dryer assembly (the bit with the desiccant in it), fit that, and then take it to a Kwik-Fit type place for a regas. However, I'd be taking a gamble that the rest of the components were still in working order. I think some places advertise "cooler aircon or you don't pay"?
However, if there was no pressure at all, I think a 20 year old system would be too much of a gamble. If I was still determined, I might go to a mobile air conditioning specialist, rather than a Kwik-Fit type place, but I'd expect quite a big bill! They have "sniffing" equipment where they can put dry nitrogen into the system and run it, looking for leaks, before they actually put the refrigerant in. The other problem you might run into on an old system, is that most of the joints in an aircon system have o-rings in them, and these will probably have dried out and cracked or at least gone hard, without being in contact with the refrigerant. Likewise the compressor shaft seal. Depending on how accessible all the joints are, you're probably looking at a fair bit of labour to swap all the seals.