EP0170688B1 - Verwendung von salicylsäureestern als riechstoffe und diese enthaltende riechstoffkompositionen - Google Patents

Verwendung von salicylsäureestern als riechstoffe und diese enthaltende riechstoffkompositionen Download PDF

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Publication number
EP0170688B1
EP0170688B1 EP85900999A EP85900999A EP0170688B1 EP 0170688 B1 EP0170688 B1 EP 0170688B1 EP 85900999 A EP85900999 A EP 85900999A EP 85900999 A EP85900999 A EP 85900999A EP 0170688 B1 EP0170688 B1 EP 0170688B1
Authority
EP
European Patent Office
Prior art keywords
salicylic acid
perfumes
utilization
acid esters
ester
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.)
Expired
Application number
EP85900999A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0170688A1 (de
Inventor
Ulf-Armin Schaper
Benno Streschnak
Siegfried BLÖSL
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/de
Application granted granted Critical
Publication of EP0170688B1 publication Critical patent/EP0170688B1/de
Expired legal-status Critical Current

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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).
  • DE-C-406 225 describes a process for the preparation of a fragrance, in which salicylic acid is mixed directly with fusel oils, i.e. the mixture of aliphatic alcohols of this name, which drops out when fermentation alcohol is obtained, to esterification.
  • fusel oils i.e. the mixture of aliphatic alcohols of this name
  • the result is products which, in addition to the amyl esters generally used in large quantities, especially by soap perfumery, also contain butyl and propyl esters.
  • a salicylic acid ester has now been found which is distinguished by surprising and valuable fragrance properties, in particular a very high adhesive strength. It is 2-ethylbutyl salicylate.
  • This ester is of particular interest because of its distinctive odor characteristics.
  • the present invention relates to the use of an ester of salicylic acid with a primary, saturated, aliphatic alcohol, which has 6 carbon atoms, as a fragrance, characterized in that the ester is 2-ethylbutyl salicylate.
  • This salicylic acid ester is prepared by known methods by esterifying salicylic acid with 2-ethylbutyl alcohol in present-day catalysts and separating off 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 alkaline catalysts.
  • the ester is known from the literature, but without mentioning its fragrance properties.
  • the olfactory characteristics of the salicylic acid ester in question can generally be described with a floral sweet, balsamic, herbaceous, typical salicylate note.
  • the claimed ester is characterized by an extraordinarily good resistance to the smell. Even after a long period of storage of the products scented with it, it does not develop any unpleasant odors. It is therefore particularly suitable for use under practical conditions due to its strong smell and its adhesive strength with great stability against aggressive media.
  • the claimed ester can be combined to create new, interesting fragrance compositions.
  • Such compositions can serve for the perfuming of cosmetics, such as scented water, creams, lotions, aerosols, toilet soaps, in a terapéutica, and for improving the odor of technical articles, such as cleaning agents, disinfectants, textile treatment agents and the like. Due to its unusual charisma and adhesive strength, the perfume ester of textile detergents, fabric softeners and cosmetics is of particular interest.
  • the compositions mentioned are added to the various products in amounts of 0.05 to 2 percent by weight, based on the entire product.
  • 2-ethyl butyl salicylate was incorporated 1.5% in basic soap.
  • the forearm of a test person 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-ethylbutylsalicylate as a perfuming agent was incorporated 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.

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)
EP85900999A 1984-02-08 1985-01-31 Verwendung von salicylsäureestern als riechstoffe und diese enthaltende riechstoffkompositionen Expired EP0170688B1 (de)

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
DE19843404310 DE3404310A1 (de) 1984-02-08 1984-02-08 Verwendung von salicylsaeureestern als riechstoffe und diese enthaltende riechstoffkompositionen
DE3404310 1984-02-08

Publications (2)

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

Family

ID=6227045

Family Applications (1)

Application Number Title Priority Date Filing Date
EP85900999A Expired EP0170688B1 (de) 1984-02-08 1985-01-31 Verwendung von salicylsäureestern als riechstoffe und diese enthaltende riechstoffkompositionen

Country Status (15)

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

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
ATE118345T1 (de) * 1990-08-07 1995-03-15 Pfizer Verwendung von interfacial polymerisierten membranen in abgabevorrichtungen.
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 (de) * 2006-08-18 2008-02-20 Cognis IP Management GmbH Kosmetische Zusammensetzungen enthaltend Ester auf Basis von 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
DE2961325D1 (en) * 1978-09-30 1982-01-14 Bayer Ag Process for preparation of alkali salts of hydroxybenzoic acid esters essentially free of water and hydroxybenzoic acids

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Chemical Abstracts, vol. 92, 21. January 1980, Columbus, Ohio, (US), D.L.J. Opdyke: "Monographs on Fragrance Raw Materials CIS-3-Hexenyl-Salicylate", page 398, column 1, abstract 28371v *

Also Published As

Publication number Publication date
SG11888G (en) 1988-07-01
CA1252731A (en) 1989-04-18
GB2153674A (en) 1985-08-29
WO1985003517A1 (en) 1985-08-15
AU571071B2 (en) 1988-03-31
JPS60181012A (ja) 1985-09-14
DE3404310A1 (de) 1985-08-08
GB2153674B (en) 1987-10-28
DE3560634D1 (en) 1987-10-22
IT8519389A0 (it) 1985-02-05
MY101288A (en) 1991-09-05
BR8505161A (pt) 1986-04-15
ZA85949B (en) 1985-09-25
HK38588A (en) 1988-06-03
AU4061185A (en) 1985-08-27
US4652401A (en) 1987-03-24
ES8602401A1 (es) 1985-12-01
GB8502790D0 (en) 1985-03-06
ES540213A0 (es) 1985-12-01
EP0170688A1 (de) 1986-02-12
IT1184315B (it) 1987-10-28

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