Typically, the lengths of cast guttering were held together with a nut and bolt at the ends, and the water seal was formed with pitch soaked rope....naturally over time this has degraded, giving you those leaks. If you can cut the bolt away, you can get into the joint with a good squirt of silicone, but if this is impossible, use some self adhesive flashing tape over the inside of the joint. If you want to paint your gutters use black Hammerite - just make sure its a dry day! Personally, give me plastic anytime...!
John, May 2009