EP0170688A1 - Utilisation d'esters de l'acide salicylique en tant que parfums et compositions de parfums les contenant. - Google Patents

Utilisation d'esters de l'acide salicylique en tant que parfums et compositions de parfums les contenant.

Info

Publication number
EP0170688A1
EP0170688A1 EP85900999A EP85900999A EP0170688A1 EP 0170688 A1 EP0170688 A1 EP 0170688A1 EP 85900999 A EP85900999 A EP 85900999A EP 85900999 A EP85900999 A EP 85900999A EP 0170688 A1 EP0170688 A1 EP 0170688A1
Authority
EP
European Patent Office
Prior art keywords
salicylic acid
acid esters
salicylate
perfumes
utilization
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP85900999A
Other languages
German (de)
English (en)
Other versions
EP0170688B1 (fr
Inventor
Ulf-Armin Schaper
Benno Streschnak
Siegfried Blosl
Walter Sommer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Priority to AT85900999T priority Critical patent/ATE29734T1/de
Publication of EP0170688A1 publication Critical patent/EP0170688A1/fr
Application granted granted Critical
Publication of EP0170688B1 publication Critical patent/EP0170688B1/fr
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring

Definitions

  • esters of salicylic acid are known from the literature. Some esters have found use in the fragrance industry, e.g. B. the methyl, butyl, amyl, hexyl, benzyl and 3-hexenylsalicylic acid esters (S. Arctander, Perfume and Flavor Chemicals 1969; and P.Z. Bedoukian, Perfum. Flavor 6 (5) 60-61 (1981).
  • salicylic acid esters A group of salicylic acid esters has now been found which is distinguished by surprising and valuable fragrance properties, in particular a very high adhesive strength. These are the salicylic acid esters of secondary or primary branched-chain, saturated aliphatic alcohols. The esters are characterized by the following general formula:
  • R residue of a secondary or primary branched chain, saturated aliphatic alcohol with 6 C atoms.
  • esters are of particular interest because of their distinctive odor characteristics.
  • the salicylic acid esters are prepared by known methods by esterifying salicylic acid with one of the definitions of general formula corresponding secondary or primary branched chain, saturated aliphatic alcohol in the presence of acidic catalysts and with the separation of the water liberated, or by reacting salicylic acid chloride with the alkali metal alcoholate of the alcohol in question, or by transesterification of methyl salicylate with the alcohol in question with the addition of alkaline catalysts.
  • the olfactory characteristics of the salicylic acid esters in question can generally be described with a floral, sweet, balsamic, typical slicylate note, whereby in individual cases floral, honey-like, herbaceous notes essentially determine the smell.
  • the claimed esters are characterized by an extraordinarily good resistance to odors. They do not develop any unpleasant odors even after the products perfumed with them have been stored for a long time. They are therefore particularly suitable for use under practical conditions because of their strong smell and their adhesive strength and at the same time great stability against aggressive media.
  • the claimed esters can be combined to create new, interesting fragrance compositions.
  • Such compositions can be used for perfuming cosmetics, such as scented water, creams, lotions, aerosols, toilet soaps, in a terapéuticas, and for improving the smell of technical articles, such as cleaning agents, Disinfectants, textile treatment agents and the like are used.
  • the esters are of particular interest for the perfuming of textile detergents, fabric softeners and cosmetics.
  • the compostions mentioned are added to the various products in amounts of 0.05 to 2 percent by weight, based on the entire product.
  • 2-Ethylbutyl salicylate was incorporated into the base soap at 1.5%.
  • the forearm of a test subject was foamed with the soap for 15 seconds and the smell of the foam was assessed.
  • the foam was then rinsed off, the arm was dried and the remaining odor was assessed over several hours.
  • 0.15% 2-ethylbutyl salicylate was incorporated as a perfume agent into the formulation of a commercial heavy-duty detergent based on anionic and nonionic surfactants, builder substances, complexing agents, perborate, graying inhibitors, dirt carriers, brighteners and fillers.
  • a second batch was perfumed with 0.15% benzyl salicylate. Normally soiled laundry was washed with the detergent in a drum washing machine in the pre and main wash cycle.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Fats And Perfumes (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Detergent Compositions (AREA)
  • Cosmetics (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

Utilisation d'esters de l'acide salicylique d'alcools aliphatiques saturés à chaîne ramifiée, primaires ou secondaires, avec 6 atomes de C, en tant que parfums.
EP85900999A 1984-02-08 1985-01-31 Utilisation d'esters de l'acide salicylique en tant que parfums et compositions de parfums les contenant Expired EP0170688B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT85900999T ATE29734T1 (de) 1984-02-08 1985-01-31 Verwendung von salicylsaeureestern als riechstoffe und diese enthaltende riechstoffkompositionen.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3404310 1984-02-08
DE19843404310 DE3404310A1 (de) 1984-02-08 1984-02-08 Verwendung von salicylsaeureestern als riechstoffe und diese enthaltende riechstoffkompositionen

Publications (2)

Publication Number Publication Date
EP0170688A1 true EP0170688A1 (fr) 1986-02-12
EP0170688B1 EP0170688B1 (fr) 1987-09-16

Family

ID=6227045

Family Applications (1)

Application Number Title Priority Date Filing Date
EP85900999A Expired EP0170688B1 (fr) 1984-02-08 1985-01-31 Utilisation d'esters de l'acide salicylique en tant que parfums et compositions de parfums les contenant

Country Status (15)

Country Link
US (1) US4652401A (fr)
EP (1) EP0170688B1 (fr)
JP (1) JPS60181012A (fr)
AU (1) AU571071B2 (fr)
BR (1) BR8505161A (fr)
CA (1) CA1252731A (fr)
DE (2) DE3404310A1 (fr)
ES (1) ES540213A0 (fr)
GB (1) GB2153674B (fr)
HK (1) HK38588A (fr)
IT (1) IT1184315B (fr)
MY (1) MY101288A (fr)
SG (1) SG11888G (fr)
WO (1) WO1985003517A1 (fr)
ZA (1) ZA85949B (fr)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5612059A (en) * 1988-08-30 1997-03-18 Pfizer Inc. Use of asymmetric membranes in delivery devices
EP0394810B1 (fr) * 1989-04-27 1993-10-13 Firmenich Sa Procédé de parfumage
US5876752A (en) * 1990-08-07 1999-03-02 Pfizer Inc. Use of interfacially-polymerized membranes in delivery devices
FR2721508B1 (fr) * 1994-06-24 1996-08-09 Rhone Poulenc Chimie Procédé d'obtention de compositions parfumantes et de produits parfumés et produits ainsi obtenus.
US5500138A (en) † 1994-10-20 1996-03-19 The Procter & Gamble Company Fabric softener compositions with improved environmental impact
US5762947A (en) * 1997-05-09 1998-06-09 Elizabeth Arden Co., Division Of Conopco, Inc. Cosmetic skin conditioning compositions containing a salicyloxy α-carboxy acid
US20050032672A1 (en) * 2003-08-06 2005-02-10 Narula Anubhav P.S. Fragrance compositions
GB0518558D0 (en) * 2005-09-12 2005-10-19 Givaudan Sa Improvements in or related to organic compounds
EP1889641A1 (fr) * 2006-08-18 2008-02-20 Cognis IP Management GmbH Compositions cosmétiques contenant un ester obtenu à partir du 2-ethylbutanol
DE102012221619A1 (de) * 2012-11-27 2014-05-28 Henkel Ag & Co. Kgaa Salicylate

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE406225C (de) * 1922-09-02 1924-11-17 Finow Metall Und Chemische Fab Verfahren zur Darstellung eines Riechstoffs und Loesungsmittels
US3714227A (en) * 1970-09-04 1973-01-30 Ueno Seiyaku Oyo Kenkyujo Kk Process for the preparation of p-hydroxybenzoic acid ester alkali metal salts
EP0009699B1 (fr) * 1978-09-30 1981-11-11 Bayer Ag Procédé de préparation de sels de métaux alcalins d'esters d'acide hydroxybenzoique pratiquement exempts d'eau et d'acides hydroxybenzoiques

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO8503517A1 *

Also Published As

Publication number Publication date
SG11888G (en) 1988-07-01
US4652401A (en) 1987-03-24
GB2153674A (en) 1985-08-29
IT8519389A0 (it) 1985-02-05
ES8602401A1 (es) 1985-12-01
GB8502790D0 (en) 1985-03-06
IT1184315B (it) 1987-10-28
JPS60181012A (ja) 1985-09-14
ES540213A0 (es) 1985-12-01
AU571071B2 (en) 1988-03-31
WO1985003517A1 (fr) 1985-08-15
BR8505161A (pt) 1986-04-15
CA1252731A (fr) 1989-04-18
DE3404310A1 (de) 1985-08-08
GB2153674B (en) 1987-10-28
MY101288A (en) 1991-09-05
AU4061185A (en) 1985-08-27
HK38588A (en) 1988-06-03
DE3560634D1 (en) 1987-10-22
EP0170688B1 (fr) 1987-09-16
ZA85949B (en) 1985-09-25

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