Due to the increasing need for continuous use of face masks caused by COVID-19, it is essential to evaluate the filtration quality that each face mask provides. In this research, an estimation method based on thermal image processing was developed; the main objective was to evaluate the effectiveness of different face masks while being used during breathing. For the acquisition of heat distribution images, a thermographic imaging system was built; moreover, a deep learning model detected the leakage percentage of each face mask with a mAP of 0.9345, recall of 0.842 and F1-score of 0.82. The results obtained from this research revealed that the filtration effectiveness depended on heat loss through the manufacturing material; the proposed estimation method is simple, fast, and can be replicated and operated by people who are not experts in the computer field.