Hardly it's possible with pure SQL or SSIS.

You need some pdf-aware soft, MS Word for example. Create vba macro which will retrieve proper images from DB and place it in a proper document layout and them save document as .pdf (word 2007+).

Or you may want to create an app using java iText lib, free for non-commercial usage. C# port is also available http://sourceforge.net/projects/itextsharp/ so SQL CLR proc may be created as well.