US 12,227,653 B2
Fluorinated coumarins
Nicholas L. Untiedt, Minneapolis, MN (US); Paul B. Armstrong, St. Paul, MN (US); Patricia M. Savu, Maplewood, MN (US); and Phillip E. Tuma, Faribault, MN (US)
Assigned to 3M Innovative Properties Company, St. Paul, MN (US)
Appl. No. 17/767,468
Filed by 3M INNOVATIVE PROPERTIES COMPANY, St. Paul, MN (US)
PCT Filed Dec. 10, 2020, PCT No. PCT/IB2020/061758
§ 371(c)(1), (2) Date Apr. 8, 2022,
PCT Pub. No. WO2021/124032, PCT Pub. Date Jun. 24, 2021.
Claims priority of provisional application 62/950,172, filed on Dec. 19, 2019.
Prior Publication US 2024/0117191 A1, Apr. 11, 2024
Int. Cl. C09B 57/02 (2006.01); C09B 69/10 (2006.01); G01M 3/20 (2006.01)
CPC C09B 57/02 (2013.01) [C09B 69/109 (2013.01); G01M 3/20 (2013.01)] 12 Claims
 
1. A fluorinated dye comprising:
a fluorescing coumarin-derived moiety connected to an oligomer of hexafluoropropylene oxide via a non-fluorinated divalent linking group, wherein the fluorinated dye is

OG Complex Work Unit Chemistry
where R1 is H or methyl; Z is a —C(═O)— or —S(═O)2—; Rf is a perfluorinated alkyl group comprising 1 to 20 carbon atoms and optionally comprising at least one catenated in-chain oxygen atom; n is greater than 2; R2 is H or methyl, and OHFPO is an oligomer of hexafluoropropylene oxide connected together via ring opening of the oligomerization.