Slow release of fragrance aldehydes and ketones in functional perfumery from dynamic mixtures generated with N‐heteroarylmethyl‐substituted secondary diamines

Abstract

Dynamic mixtures of aminals generated by reversible reaction of diamines with volatile aldehydes and ketones are suitable delivery systems to increase the long‐lastingness of fragrance perception in functional perfumery applications. N‐Heteroarylmethyl‐substituted secondary diamines of 1,2‐diaminocyclohexane, 1,3‐diaminocyclohexane, 1,2‐diaminoethane, 1,2‐diaminopropane, 1,3‐diaminopropane or 2‐(aminomethyl)piperidine were prepared by reaction with furan‐, 1H‐pyrrole‐, thiophene‐ or pyridine‐2‐carbaldehyde and reduction of the intermediate imines with NaBH4. The performance of the delivery system was evaluated in a fabric softener application in the presence and absence of a diamine by following the evaporation of a mixture of 18 fragrance aldehydes and ketones on dry cotton using dynamic headspace analysis. Equilibration of the mixture in the presence of a diamine simultaneously increased the headspace concentrations of several fragrance raw materials above the cotton surface as compared to a reference sample without diamine. Equilibrated dynamic mixtures of diamines were found to be suitable delivery systems to prolong the evaporation of fragrance aldehydes and ketones in practical applications of functional perfumery. Copyright © 2013 John Wiley & Sons, Ltd.

Functionalized cellulose nanocrystals as nanocarriers for sustained fragrance release

“…3.1. As it has been shown in the past for polymeric and small molecule systems, [20][21][22][23][24]49 and in the kinetic experiment shown in Fig. 3, an acidic environment is favorable for storing thiolene adducts, because the retro 1,4-Michael-type reaction (Scheme 1) is suppressed in the acidic environment.…”

“…[20][21][22][23][24]49 Dry βD-CNCs (100 mg) were mixed directly with the aqueous surfactant emulsion (1.8 g) and deionized water (1 mL) was added to permit better mixing. The mixtures were stirred for 10 min, transferred into 1 L beakers and diluted with deionized water (600 g).…”

Sustained‐release properties of cotton fabrics impregnated with nanotuberose fragrance

“…The main absorption peaks appearing in the FTIR spectra of the TF corresponded to the absorption peak of OH (3538 cm − ), the three absorption peaks of (O)CH (2860, 2930, and 2962 cm − ), the absorption peak of CO (1728 cm − ), and the two absorption peaks of benzene ring (monosubstituted or disubstituted) in the fingerprint region (751 and 698 cm − ). For PBCA, the characteristic absorption bands at 3430 cm − were attributed to the stretching vibrations of OH groups, which belonged to OH − as an initiator during the polymerization of PBCA [Figure (D)]. All of these peaks appeared in the spectrum of Nano‐TF, however, the stretching vibrations peak of OH shifted to 3482 cm − because of the function of the hydrogen bonds between TF and PBCA.…”

“…Fragrances and flavors as small molecular compounds have been applied in many fields, including perfumes, textiles, food additives, medicines, cosmetics, tobacco, leather, and carbonless copying paper. However, the easy volatilization, oxidation, and distortion of flavors and fragrances during their manufacturing, storage, and use inhibits their utilization .…”

“Old” chemistry in a new context: photocleavable 2-oxoacetate-containing latex dispersions and core–shell microcapsules for the controlled release of volatile compounds

“…26 The delivery systems were added to an aqueous emulsion of quaternised triethanolamine esters of fatty acids (TEA-esterquats) 27 and diluted with tap water. A cotton sheet was then added and moved around in the emulsion for a few minutes before being wrung out and line dried in the dark for 1 day.…”