Polymers with paraffin-like structures have been used as middle distillate flow improvers in the petroleum industry. Hundreds of ppm of these polymers can dramatically improve the cold properties of diesel (cloud point, cold filter plugging point, pour point). Starting from mono-substituted alkylphenols, novolac resins and acrylic polymers were newly designed and synthesized. It has also been found that structural differences in alkyl chain can have a significant impact on performance. Among the samples, PPDPA can improve all cold properties, and NPDP was highly effective in reducing pour point. It should be noted that these polymers exhibit superior performances over conventional EVA-based polymers.