The Procter Gamble Company

Gregory Mark Bunke

Kenneth Edward Yelm

John Christian Haught

Alan David Willey

Robb Richard Gardner

Jacob Robert Adams

Kady Lynn Willison

Photoactivators comprise a photoactive moiety and a hydrophilic moiety. The photoactivators preferably comprise less than about 35%, by weight of the photoactivator, of the photoactive moiety. The photoactivators can be activated to a photo-excited state by excitation with incident radiation of a wavelength between about 350 nm and 750 nm, preferably between about 350 nm and about 420 nm. The photoactivators further encompass those having certain chemical formulations.

Photoactivators

The present invention provides synthetic routes for preparing various isomers of cyclohexane-based coolants, such as menthyl esters and menthanecarboxamide derivatives, in particular those substituted at the amide nitrogen, for example with an aromatic ring or aryl moiety. Such structures have high cooling potency and long lasting sensory effect, which make them useful in a wide variety of consumer products. One synthetic route involves a copper catalyzed coupling of a primary menthanecarboxamide with an aryl halide, such reaction working best in the presence of potassium phosphate and water. Using this synthetic route, specific isomers can be prepared including the menthanecarboxamide isomer having the same configuration as l-menthol and new isomers such as a neoisomer having opposite stereochemistry at the carboxamide (C-1) position. The neoisomer unexpectedly has potent and long lasting cooling effect. Preparation schemes for neoisomers of other menthyl derivatives which are useful as coolants, including esters, ethers, carboxy esters and other N-substituted carboxamides are also provided.

Synthesis of cyclohexane derivatives useful as sensates in consumer products

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Lawrenceburg, IN, United States of America

Gregory Mark Bunke