Gas hydrate deposition is a complex issue with significant implications for the oil and gas industry. The formation of solid gas hydrates in the hydrocarbon transportation pipelines leads to production disruptions and potentially even complete blockages, resulting in huge financial losses and operational difficulties. For over two decades, kinetic gas hydrate inhibitors have played a crucial role in preventing the formation of gas hydrates within the flow lines of oil and gas production. They directly influence the kinetics of hydrate formation, hindering nucleation and slowing down crystal growth. In this study, five new waterborne polyurethanes (WPUs) with varying degrees of hydrophobicity as inhibitors for cubic structure II gas hydrates were synthesized and tested using rocking cells and differential scanning calorimetry. The synthesis of WPUs involved the reaction between dialkylamines (diethyl, dipropyl, dibutyl, dibenzyl, and dioctyl) and glycidol under mild conditions. All WPUs effectively prevented gas hydrate formation, and a correlation between their efficiency and the alkyl chain length was observed. The inhibitory efficacy of WPUs increased with the extension of the alkyl chain from ethyl to butyl. WPU-DBuA, featuring butyl groups, exhibited the highest inhibition activity. It provided a subcooling temperature of 12.9 and 15.6 °C at 0.25 and 0.5 wt%, respectively, surpassing commercial samples, such as Luvicap EG and Luvicap 55 W. Additionally, the solutions containing 1 and 2 wt% of WPU-DBu exhibited maximum subcooling temperatures of 16.2 °C and 16.7 °C, respectively, which correspond to a 79.7 % and 85.4 % reduction in gas uptake during hydrate growth compared to pure water. However, the inhibitory power of WPUs diminished with larger alkyl (dioctyl) or aromatic groups (dibenzyl), indicating that dibutyl represents the optimal alkyl length for achieving maximum performance. Moreover, WPUs demonstrated a reduction in hydrate conversion under static conditions, signifying their efficiency when the flow is stopped. WPUs lowered the onset temperature of hydrate formation from 3 °C in pure water to temperatures below −12 °C. Thus, WPUs demonstrated a remarkable ability to prevent the formation of structure II gas hydrates, even under high subcooling conditions. Additionally, WPU-DBuA exhibits a considerable degree of biodegradability, as evidenced by its biodegradation level of 44 %, suggesting that it has the potential to break down more easily in the environment compared to Luvicap 55 W. This research contributes to a deeper understanding of the structure–property relationships of KHIs. This can facilitate the development of more effective and eco-friendly inhibitors, which helps address environmental concerns associated with using KHIs in the oil and gas industry.