Automatically set 'From' mail address depending on contact categor

Hi

I was wondering if there is a way to have outlook choose the right 'From'
address and mail signature depending on the category that the contact the
email is going to is in?

Ideally I would like to get it to set the from address and signature for
contacts in my business category to a 'business' facing email and signature
(e.g. appropriate disclaimers etc), but for my personal contacts category to
send from my personal email address.

I'm not using outlook with exchange this is purely with POP3.

Thanks for any tips on how to do this!

Matt