These mother-of-pearl chips are listed in the late Efrain Archilla-Diez book "Catalog Numismatico de Puerto Rico" with catalog numbers H0685 - $5, H0690 - $50, H0695 - $100 and H0700 - $500. He has only the $100 chip pictured which is what similar to the $500 and $1000 chips you show. The $1000 chip was not listed and probably not known to him at that time. This book was very comprehensive for the time and much more has come to light since the 1990 publication of this catalog.