Fluorinated coumarins

Patent metadata

Field	Value
Publication number	US-12227653-B2
Application number	US-202017767468-A
Country	US
Kind code	B2
Filing date	Dec 10, 2020
Priority date	Dec 19, 2019
Publication date	Feb 18, 2025
Grant date	Feb 18, 2025

Abstract

Described herein is fluorinated dye comprising: a fluorescing coumarin-derived moiety connected to an oligomer of hexafluoropropylene oxide via a non-fluorinated divalent linking group. Such fluorinated dyes are soluble in fluorinated fluids and may be used to detect leaks in various systems such as refrigerant, air conditioning and/or heat transfer systems.

First claim

What is claimed is:

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

where R 1 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; R 2 is H or methyl, and OHFPO is an oligomer of hexafluoropropylene oxide connected together via ring opening of the oligomerization.

2. The fluorinated dye according to claim 1 , wherein the oligomer comprises at least 2 interpolymerized hexafluoropropylene oxide units.

3. The fluorinated dye according to claim 1 , wherein the fluorinated dye does not sufficiently absorb visible electromagnetic radiation.

4. The fluorinated dye according to claim 1 , wherein the fluorinated dye absorbs ultraviolet electromagnetic radiation.

5. A testing composition comprising the fluorinated dye according to claim 1 and fluorinated fluid.

6. The testing composition according to claim 5 , wherein the fluorinated fluid comprises a perfluorocarbon, a perfluoropolyether, a hydrochlorofluorocarbon, a hydrofluoroether, a hydrofluorocarbon, a hydrohalofluoroether, a hydrofluoroolefins, or mixtures thereof.

7. The testing composition according to claim 5 , wherein the fluorinated dye has a solubility in the fluorinated fluid of at least 0.1% by weight.

8. The testing composition according to claim 5 , wherein the fluorinated dye has a solubility in the fluorinated fluid of at least 1.0% by weight.

9. The testing composition according to claim 5 , wherein the fluorinated dye is miscible with the fluorinated fluid.

10. The testing composition according to claim 5 , wherein the fluorinated fluids comprise at least one of a hydrofluoroether or a perfluorinated cyclic amine.

11. A method of using the fluorinated dye according to claim 1 as a leak detector.

12. A method for detecting leaks in a refrigeration system comprising (a) introducing a fluorinated dye comprising a fluorescing coumarin-derived moiety connected to an oligomer of hexafluoropropylene oxide via a non-fluorinated divalent linking group according to claim 1 , within a refrigeration system comprising a refrigerant composition comprising a fluorinated fluid, (b) operating the refrigeration system for a sufficient time to allow for thorough mixing of the fluorinated dye and the refrigerant composition; and (c) determining the presence of a leak in the refrigeration system by directing an ultraviolet light at the refrigeration system and subsequently detecting a fluorescing color.

Assignees

• 3M Innovative Properties Company

Inventors

• Untiedt Nicholas L
• Armstrong Paul B
• Savu Patricia M
• Tuma Phillip E

Classifications

• G01M3/20

  using special tracer materials, e.g. dye, fluorescent material, radioactive material · CPC title

• C09B69/109

  containing other specific dyes · CPC title

• G01M3/228

  for radiators · CPC title

• C09B57/02 Primary

  Coumarine dyes · CPC title