Based on what I found in regard to changes in addresses and logos over the years, it looks like your book was issued around 1930 or later. For as long as MB was in business, there really isn't much information to be found.
1852-1853 John McLoughlin No. 3 Tyron Row, NYC
1854-1858 John McLoughlin 24 Beekman St., NYC
1858-1862 McLoughlin Brothers 24 Beekman St., NYC
1863-1870 McLoughlin Brothers 30 Beekman St., NYC
1871-1886 McLoughlin Brothers 71 & 73 Duane St., NYC
1886-189? McLoughlin Brothers 623 Broadway, NYC
1898-1919 McLoughlin Brothers 890 Broadway, NYC
1920-1929 McLoughlin Brothers Springfield, Mass., No M/B logo
1930-196? McLoughlin Brothers Springfield Mass., with M/B logo