I've owned the M-100, Momentum, MDR1R at the same time. Bear with me as I'm writing from my memory of the phones so take it with a grain of salt.
Momentum > the other two In mids for my preferences + sounded better all round. Very subjective of course. I listen to Rock, Metal, Jazz, Punk, Kpop, Pop and Hip Hop. So for me it was a better all rounder.The M-100 had more bass, but less defined than the Momentum. The Momentum was about the same in instrument separation. Case is bulky and headphone does not fold. It has the best build quality of the 3 I mention, but the M-100 still has it beat in this regard.
The MDR-1r of course can also include noise cancelling I believe, nice warmer sound. Prefered the fuller midrange than the M-100. Less bass than the M-100, with my type of music separation was worse. Comfort was incredible. Doesn't come with a good case for travel only a pouch and a cardboard box case. Doesn't fold down. Plastic construction.
UE6000 is another to look at. Noise Cancelling, good bass, at least as good overall as the M-100 in my audition. Supremely comfortable. Comes with a soft carry case which is rather nice. Folds nicely.
None of the 3 are massive improvements IMO, can very much come down to taste + YMMV
My source was a Sony E475 - LOD - Hippo Cri Cri dac/amp - HP's
Sorry if I'm not helpful