Supercharge Your Innovation With Domain-Expert AI Agents!

Photolabile acetal and ketal compounds for controlled release of reactive volatile carbonyl compounds

A technology for releasing active compounds, applied in softening compositions, detergent compositions, fragrances, organic chemistry, etc.

Active Publication Date: 2021-06-18
FIRMENICH SA
View PDF18 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

To the best of our knowledge, none of the prior art literature suggests or anticipates that photosensitive acetal and ketal compounds of formula (I) are indeed suitable as delivery systems for controlled release of volatile compounds

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Photolabile acetal and ketal compounds for controlled release of reactive volatile carbonyl compounds
  • Photolabile acetal and ketal compounds for controlled release of reactive volatile carbonyl compounds
  • Photolabile acetal and ketal compounds for controlled release of reactive volatile carbonyl compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0077] Preparation of non-commercial diols of formula (II) according to the invention

[0078] a) Preparation of 2-(bis(3-(dimethylamino)phenyl)(hydroxyl)methyl)phenol

[0079] Phenyl lithium (2M in cyclohexane, 9.86 mL, 19.7 mmol) was added to a solution of methyl salicylate (3.00 g, 19.7 mmol) in tetrahydrofuran (THF, 20 mL) at -78 °C over 15 minutes . After stirring at -78°C for 5 minutes, the reaction mixture was transferred to a solution of 3-bromo-N,N-dimethylaniline (7.89 g, 39.4 mmol) and magnesium turnings (1.15 g, 47.3 mmol) in THF over 20 minutes. (approximately 110 mL) of the Grignard reagent prepared in (approximately 110 mL) was kept at 0 °C during the addition. The reaction mixture was warmed to room temperature. After stirring at room temperature for 24 hours, the reaction mixture was decanted and quenched with saturated ammonium chloride solution (about 200 mL). Extracted with ethyl acetate, dried (Na 2 SO 4 ) and concentrated to give 7.97 g of crude p...

Embodiment 2

[0103] Preparation of photosensitive acetal or ketal of formula (I) according to the present invention

[0104] a) (±)-3,3'-(2-(9-decenyl)-4H-benzo[d][1,3]dioxane-4,4-diyl)bis(N, Synthesis of N-dimethylaniline)

[0105] 2-(bis(3-(dimethylamino)phenyl)(hydroxyl)methyl)phenol (0.50g, 1.4mmol) and 10-undecenal (0.46g, 2.8mmol) were mixed at 140°C The mixture was stirred for 2 hours to obtain a crude reaction product. Column chromatography (SiO 2 , heptane / ethyl acetate 3:1) and bulb-to-bulb distillation (110° C., 0.2 mbar) to remove residual 10-undecenal to yield 0.61 g (86%) of the title compound.

[0106] 1 H-NMR: 7.17(t,1H),7.14-7.09(m,1H),7.08(t,1H),6.91-6.84(m,2H),6.81-6.74(m,3H),6.72-6.66(m ,2H),6.64-6.57(m,1H),6.56-6.51(m,1H),5.86-5.75(m,1H),5.10-5.05(m,1H),5.02-4.89(m,2H),2.87 (s,6H),2.83(s,6H),2.08-1.99(m,2H),1.92-1.77(m,2H),1.58-1.41(m,2H),1.41-1.15(m,10H).

[0107] 13 C-NMR:152.38,150.31,150.14,147.02,145.17,139.21,129.83,128.29,128.15,127.94,126.21,119.75,11...

Embodiment 3

[0141] All R in formula (I) 4 and R 5 Preparation of Photosensitive Acetal or Ketal Compounds Both Are Hydrogen Atoms

[0142] a) Synthesis of 2-(hydroxydiphenylmethyl)phenol

[0143] Bromobenzene (27.70 g, 176 mmol) was weighed into a dropping funnel, and to a suspension of magnesium turnings (5.10 g, 210 mmol) in diethyl ether (10 mL) were added about 50 drops of pure compound and a few crystals of iodine. Diethyl ether (50 mL) was then added to the residual bromobenzene and the solution was added dropwise over 30 minutes. The reaction mixture was heated to reflux for 1 hour. After cooling to room temperature, salicylic acid (2.89 g, 21 mmol) in diethyl ether (50 mL) was added dropwise over 30 minutes. The reaction mixture was stirred overnight at room temperature, then poured into aqueous HCl (10%, 100 mL) and ice (100 g). Extracted with diethyl ether (2 x 100 mL), using aqueous NaOH (10%, 100 mL) and ice (50 mL), saturated NaHCO 3 aqueous solution (2x 50mL), satur...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
wavelengthaaaaaaaaaa
Login to View More

Abstract

The present invention relates to a delivery system based on photosensitive acetal or ketal compounds capable of releasing reactive volatile carbonyl compounds from surfaces to the surroundings in a controlled manner upon exposure to light. The delivery system can be used to deliver active substances such as flavours, fragrances, malodor counteractants, insect attractants or insect repellents. The invention also relates to the use of said acetal or ketal compounds in perfumery and in perfuming compositions or perfuming consumer articles.

Description

technical field [0001] The present invention relates to the field of fragrances. More specifically, the present invention relates to delivery systems based on photosensitive acetal or ketal compounds of formula (I) capable of releasing active volatile compounds in a controlled manner upon exposure to light. carbonyl compounds. The invention also relates to the use of said acetal or ketal compounds in perfumery and in perfuming compositions or perfuming consumer articles. Background technique [0002] Seasonings and spices as well as insect attractants or repellents are volatile molecules that can only be perceived for a limited time. [0003] The perfumery industry is of particular interest in compositions or additives capable of prolonging or enhancing the perfuming action of a mixture of several fragrances simultaneously over a period of time. It is particularly desirable to obtain the long-lasting properties of standard fragrance raw materials which are too volatile or...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07D319/08C11B9/00
CPCC07D319/08C11B9/0003C11B9/0015C11D3/001C11D3/50
Inventor A·赫尔曼
Owner FIRMENICH SA
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com