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Controlled release of active aldehydes and ketones from equilibrated dynamic mixtures

A mixture, reactive aldehyde technology, applied in animal repellents, organic active ingredients, detergent composition fragrances, etc., can solve the problem of not mentioning the principle of dynamic mixture

Inactive Publication Date: 2009-12-16
FIRMENICH SA +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In this document, there is no mention of the principle of generating a dynamic mixture

Method used

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  • Controlled release of active aldehydes and ketones from equilibrated dynamic mixtures
  • Controlled release of active aldehydes and ketones from equilibrated dynamic mixtures
  • Controlled release of active aldehydes and ketones from equilibrated dynamic mixtures

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0232] Generation of the dynamic mixture of the present invention

[0233] In deuterated aqueous buffer solution (DMSO-d 6 / D 2 O 2:1 (v / v)) through 1 H-NMR spectroscopy monitors the formation of kinetic mixtures. The aqueous portion of the deuterated buffer stock was prepared from the following quantities of product:

[0234] Na 2 HPO 4 0.817g

[0235] K H 2 PO 4 0.107g

[0236] D. 2 O 22.10g (= 20ml)

[0237] Add 1.0ml DMSO-d 6 into the aqueous portion of 0.5 ml deuterated buffered stock solution to produce a final reaction solution whose pH was determined to be 6.5-7.0 (using Merck pH test paper 5.5 ~ 9.0).

[0238] In order to verify the generation and hydrolysis of the aminal derivatives of the present invention, the same equilibrium is formed, in DMSO-d 6 180 mM solutions of diamine derivatives, reactive aldehydes or ketones and corresponding aminal derivatives were prepared in . Then, add 0.05 ml of diamine derivative solution, 0.05 ml of reac...

Embodiment 2

[0246] The reversibility of the equilibrium of the dynamic mixture of the present invention

[0247] In order to demonstrate that the same equilibrium is obtained in both directions of the reaction and to determine the corresponding equilibrium constants, after the generation and hydrolysis of the aminals of the present invention, the deuterated aqueous buffer stock solution (THF-d 8 / D 2 O 2:1 (v / v)) 1 H-NMR. The aqueous portion of the deuterated buffer stock was prepared as described above (Example 1).

[0248] For this assay, in THF-d 8 180 mM solutions of diamine derivatives and reactive aldehydes were prepared in . Similarly, 90 mM solutions of the corresponding aminals were prepared in the same solvent. Then, to 0.3 ml of aqueous buffer stock solution in an NMR tube, add 0.05 ml of diamine derivative solution, 0.05 ml of reactive aldehyde solution, and 0.50 ml of THF-d 8 , or add 0.10ml of the corresponding aminal derivative and 0.50ml of THF-d 8 . Thus, each t...

Embodiment 3

[0263] Properties of Softener Bases Comprising Kinetic Mixtures of the Invention

[0264] The mixtures of the invention have been tested for use as perfuming ingredients in fabric softeners. A fabric softener base has been prepared with the following final composition:

[0265] VK90 (source: Stepan) 16.5wt%

[0266] Calcium chloride 0.2wt%

[0267] Water 83.3wt%

[0268] The perfuming performance over time of free aromatized aldehydes / ketones and mixtures according to the invention (i.e. free aromatized aldehydes / ketones and diamine derivatives as additives) was determined by the following test:

[0269] Weigh (1R,2R)-N,N'-dibenzyl-1,2-cyclohexanediamine (73.4 mg, 2.46 mmol) into a vial. Then add 1.80 g of the above fabric softener base, containing equimolar amounts (0.41 mmol) of 2-furfuraldehyde (furfural, 39.4 mg), (R)-3,7-dimethyl-6-octane in 10 ml of ethanol Enal (citronellal, 63.2mg), 3-phenylbutyraldehyde ( 60.8 mg), 2-pentyl-1-cyclopentanone (Delphone, 63.2 ...

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Abstract

The present invention concerns a dynamic mixture obtained by combining, in the presence of water, at least one diamine derivative, comprising at least one benzylamine moiety, with at least one active aldehyde or ketone. The invention's mixture is capable of releasing in a controlled and prolonged manner said active compound, in particular perfuming ingredients, in the surrounding environment.

Description

technical field [0001] The present invention relates to a dynamic mixture obtainable by combining at least one diamine derivative of formula (I) as further defined below with at least one volatile reactive aldehyde or ketone in the presence of water. The mixtures according to the invention release the active substances in the surrounding environment in a controlled and sustained manner. [0002] The invention also relates to the use of said dynamic mixtures as perfuming ingredients and to perfuming compositions or fragranced articles comprising the mixtures according to the invention. Another object of the invention is the use of said diamine derivatives as additives to prolong the perfuming effect of specific aldehydes or ketones. Background technique [0003] Flavoring and perfuming agents, as well as insect attractants or repellents, are volatile molecules that are only perceived for a limited period of time. [0004] The perfumery industry is particularly interested in...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/04C11D3/50C07D233/02A61Q13/00
CPCA01N43/50C07D233/02C11B9/00C11D3/50A61K31/505C07D239/04A01N35/04A01N35/02A61Q13/00A61K31/415A01N43/54C11D3/30A01N25/18A01N33/02
Inventor 安德烈亚斯·赫尔曼纪尧姆·戈丹让-马里·莱恩让－马里·莱恩
Owner FIRMENICH SA
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