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Alkyl enol ether properfume

A technology of alkyl and cycloalkyl, which is applied in the preparation of essential oils/fragrances, detergent composition fragrances, and carbon-based compounds, and can solve problems such as lack of persistence, non-retention, and short-term fragrance effect

Pending Publication Date: 2021-05-04
FIRMENICH SA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In fact, many actives which are particularly suitable for this type of application are known to lack tenacity on the laundry, or do not remain on the laundry when rinsed, with the result that their perfuming effect is only transient and not very intense experience

Method used

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  • Alkyl enol ether properfume
  • Alkyl enol ether properfume
  • Alkyl enol ether properfume

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0086] The preparation of aqueous dispersions / slurries of core-shell microcapsules is well known to those skilled in the art. In one form, the microcapsule wall material may comprise any suitable resin and include melamine, glyoxal, polyurea, polyurethane, polyamide, polyester, and the like, among others. Suitable resins include the reaction products of aldehydes and amines, suitable aldehydes include formaldehyde and glyoxal. Suitable amines include melamine, urea, benzoguanamine, glycoluril and mixtures thereof. Suitable melamines include methylol melamine, methylated methylol melamine, imino melamine and mixtures thereof. Suitable ureas include dimethylol urea, methylated dimethylol urea, urea-resorcinol, and mixtures thereof. Suitable materials of manufacture can be obtained from one or more of Solutia Inc. (St Louis, Missouri U.S.A.), Cytec Industries (West Paterson, New Jersey U.S.A.), Sigma-Aldrich (St. Louis, Missouri U.S.A.).

[0087] According to a particular embo...

Embodiment 1 to 6

[0219] Dimethyl acetal (35mmol), alcohol (70mmol) and KHSO 4 (48mg, 0.35mmol) was added to a 25ml round bottom flask equipped with a distillation head and nitrogen bubbler. The mixture was heated (oil bath at 150°C) while distilling off the liberated methanol (vapor temperature 64°C) until the vapor temperature dropped (40-60 minutes), indicating that most of the methanol had been removed. The mixture was placed under vacuum (300 mTorr) and heated (180-190° C. oil bath) for 2-3 hours while the liberated alcohol was distilled from the reaction flask. Adding Na 2 CO 3 (0.5 g), the enol ether was isolated from the reaction flask by vacuum distillation, or by flash chromatography on silica gel followed by Kugelrohr distillation.

Embodiment 1

[0220] Example 1. (2-((2-methylundec-1-en-1-yl)oxy)ethyl)benzene:

[0221] Starting from the dimethyl acetal of 2-methylundecanal and 2-phenylethanol, the title compound was isolated by distillation (bp 130 °C, 30 mTorr) as a colorless oil in 91% yield (E / Z=59:41).

[0222] 1 H NMR (CDCl 3 , 500MHz, E-isomer): δ0.88(t, J=7.0Hz, 3H), 1.19-1.39(m, 14H), 1.57(s, 3H), 1.85(t, J=7.5Hz, 2H ),2.91(t,J=7.3Hz,2H),3.86(t,J=7.3Hz,2H),5.81(s,1H),7.17-7.30(m,5H).

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Abstract

The present invention relates to compounds of formula (I) as properfume compounds. In particular, the present invention relates to a method to release a compound being a ketone of formula (II), a formate ester of formula (III) and / or an alcohol of formula (IV) by exposing the compound of formula (I) to an environment wherein it is oxidized. Moreover, the present invention relates to a perfuming composition and a perfumed consumer product comprising at least one compound of formula (I).

Description

technical field [0001] The present invention relates to compounds of formula (I) as properfumes. In particular, the present invention relates to the release of ketones of formula (II), formates of formula (III) and / or alcohols of formula (IV) by exposing compounds of formula (I) to an environment in which they are oxidized. method. Furthermore, the present invention relates to perfuming compositions and perfumed consumer products comprising at least one compound of formula (I). Background technique [0002] The fragrance (perfume) industry is particularly interested in compositions or additives capable of prolonging or enhancing the perfuming effect of mixtures of several fragrances simultaneously over a certain period of time. Achieving long-lasting performance is particularly desirable for standard fragrance raw materials, which are inherently too volatile or have poor substantivity, or deposit only a small amount on the end-use surface. Additionally, some fragrance ing...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/15C07C43/166C07C43/168C07C43/188C07C43/215C07C45/34C07C45/36C07C67/39A61K8/30
CPCC07C43/15C07C43/166C07C67/39C07C43/168C07C43/188C07C43/215C07C45/34C07C45/36C07C63/16C07C45/37C07C49/04C07C47/02C07C2601/18C07C2601/16A61K8/33A61Q5/02A61Q5/12A61Q15/00A61Q19/10C07C29/50C11B9/0061C11D3/2068C11D3/50
Inventor G·B·沃玛克B·因德拉达斯
Owner FIRMENICH SA