Starting in the early 1900's, several of the Illinois Outman's, including William Henry Outman and his sons
Orr, Winifred, and Leslie, worked for the Certain-Teed roofing company, both in Illinois and California.
In May 1931 Winfred H. Outman applied for 2 U. S. Patents for a type of roofing shingle and a method of making
of these shingles. These patents were issued in November 1937. Winfred's patent for the shingle-making process was an
improvement on his brother Orr's 1922 patent. Here are links to his patents on Google:
Below are images from his 2 patents: