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Fragrance pro-accords and aldehyde and ketone fragrance libraries

A technology for the raw material of an incense and a fragrance, which is applied in the field of fragrance release systems and can solve the problems of inability to regulate the release performance of fragrance precursors and the like

Inactive Publication Date: 2002-01-23
THE PROCTER & GAMBLE COMPANY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Despite the fact that these materials are capable of delivering the desired aldehydes and ketones under moderately acidic conditions, historically, these compounds have not been able to provide formulators with high levels of sustained and predictable release of aldehydes and ketones due to the inability to control the pro-fragrance release profile. controllable method

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0559] Embodiment 1 Preparation of N-isopropyl-DL-serine methyl ester (1)

[0560] To a slurry of 1 equivalent of DL-serine methyl ester hydrochloride and 2 equivalents of anhydrous sodium sulfate in methanol was added 1.05 equivalents of sodium methoxide. The mixture was stirred at room temperature for 5 minutes after which time 3 equivalents of acetone were added and the slurry was stirred overnight. The solids were removed by filtration and excess acetone was removed from the filtrate under reduced pressure. Once the acetone was removed, platinum(IV) oxide (0.02 equiv) was added. The slurry was stirred at room temperature under an atmosphere of hydrogen for 24 hours. The slurry was then filtered and excess methanol was removed under reduced pressure. The residue was slurried in chloroform and filtered, and the filtrate was washed with dilute sodium bicarbonate, dried over anhydrous sodium sulfate, and filtered. Chloroform was removed under reduce...

Embodiment 2

[0562] Preparation of 2,4-dimethyl-3-cyclohexene-1-carbaldehyde (triplal)-N-isopropyl-DL-serine methyl ester oxazolidine (3)

[0563] 2,4-Dimethyl-3-cyclohexene-1-carbaldehyde (triplal) (2, 1.0 equivalents), N-isopropyl-DL-serine methyl ester (1, 1.05 equivalents) and 2,6- A solution of dichlorobenzoic acid (0.01 equiv) was refluxed in toluene for 6 hours during which time water was removed by azeotropic distillation. The solution was cooled, washed with saturated sodium bicarbonate, dried over anhydrous sodium sulfate, and filtered. Subsequent removal of toluene under reduced pressure yielded the desired product 3.

Embodiment 3

[0565] Preparation of oxazolidine releasers from aldehyde / ketone mixtures

[0566] At room temperature, 1.0 equivalents of 2,4-dimethyl-3-cyclohexene-1-carbaldehyde (2), melonal (4), helional (5), pt-bucinal (7) , cymenal (6) and slurries of methyl dihydrojasmonate (8) with N-isopropyl-DL-serine methyl ester (1, 6.3 equivalents) and anhydrous sodium sulfate (12.0 equivalents) in anhydrous Stir in absolute ethanol for 2 weeks. Sodium sulfate was removed by filtration to obtain an alcoholic solution of the product. This solution was used without further purification. Alternatively, ethanol can be removed under reduced pressure.

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PUM

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Abstract

The present invention relates to novel heterocyclic pro-fragrances, preferably oxazolidines, tertahydro-1,3-oxazines, thiazolidines, or tetrahydro-1,3-thiazines, more preferably oxazolidines, or tertahydro-1,3-oxazines, most preferably oxazolidines, which are capable of sustained release of fragrance raw material ketones and aldehydes and to fragrance delivery systems which comprise said pro-fragrances.

Description

field of invention [0001] The present invention relates to novel fragrance-accord pro-accords (pro-acords), which release the raw material aldehydes and ketones suitable for perfume and fine fragrance compositions, thereby providing the basis for said combination. The compound provides long-lasting aromatic properties. The present invention further relates to a perfume delivery system comprising a) one or more accord precursors, in particular acetals, ketals, orthoesters, orthocarbonate compounds, and b) Novel fragrance accord precursors of the present invention in which one or more fragrance raw materials are combined. Background of the invention [0002] Humans have applied scents and fragrances to their skin since ancient times. Originally, these aesthetically pleasing substances were often resins, gums or essential oils isolated in raw form from natural sources, especially the barks, roots, leaves and fruits of indigenous plants. These resins, gums, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/06C11B9/00
CPCA61K2800/57A61K8/49A61Q13/00C07D263/06
Inventor G·S·米拉克勒K·N·普里斯
Owner THE PROCTER & GAMBLE COMPANY
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