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I also have a ctb file I created to convert all standard colors to greyscale shades. I edited color 220 to "Red" and get the results I expected- see images attached. I am using (plain vanilla) AutoCAD 2020.1 on Win10 Pro v1903 build 18362.356.
Plotted using Adobe Acrobat pdf driver. Not a lot of contrast between the almost-magenta native color 220 and red, but enough to see that it works on my end.
What is your AutoCAD version/Windows version, and are both up-to-date?
Also a dumb question- when you plot and do not get the desired/expected result, are you certain you are using the newly edited version of the ctb file in question? No chance your acad file directory is pointing to an older, un-edited ctb file? Network copy instead of a local or vice-versa?
Are you plotting to pdf or a physical printer? In either case, is there an override in place in the driver settings (or on physical printer) to convert colors to greyscale or print Black&White?
That's about all the ideas I have- hope one works...