EP0168415B1 - Verwendung von salicylsäureestern als riechstoffe, diese enthaltende riechstoffkompositionen, sowie neue salicylsäureester - Google Patents

Verwendung von salicylsäureestern als riechstoffe, diese enthaltende riechstoffkompositionen, sowie neue salicylsäureester Download PDF

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Publication number
EP0168415B1
EP0168415B1 EP85900107A EP85900107A EP0168415B1 EP 0168415 B1 EP0168415 B1 EP 0168415B1 EP 85900107 A EP85900107 A EP 85900107A EP 85900107 A EP85900107 A EP 85900107A EP 0168415 B1 EP0168415 B1 EP 0168415B1
Authority
EP
European Patent Office
Prior art keywords
salicylic acid
acid esters
salicylate
perfuming
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.)
Expired
Application number
EP85900107A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0168415A1 (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.)
BASF Personal Care and Nutrition GmbH
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 AT85900107T priority Critical patent/ATE28892T1/de
Publication of EP0168415A1 publication Critical patent/EP0168415A1/de
Application granted granted Critical
Publication of EP0168415B1 publication Critical patent/EP0168415B1/de
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. the methyl, butyl, amyl, hexyl, benzyl and 3-hexenylsalicylic acid esters (S. Arctander, Perfume and Flavor Chemicals, 1969; and PZ Bedoukian, Perfum. Flavor 6 (5), 60-61 (1981). )
  • the salicylic acid esters are prepared by known methods by esterifying salicylic acid with a carbocyclic alcohol corresponding to the definition of the general formula, if appropriate in the presence of acidic or alkaline catalysts and with removal of the water thereby released, or by reacting salicylic acid chloride with the alkali metal alcoholate of the carbocyclic alcohol, or by transesterification of methyl salicylate with the carbocyclic alcohol.
  • the olfactory characteristics of the salicylic acid esters in question can generally be described with a flowery, typical salicylate note, whereby in individual cases floral, aromatic, balsamic notes essentially determine the smell.
  • the claimed esters 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.
  • the esters are of particular interest for the perfuming of textile detergents, fabric softeners and cosmetics.
  • the compositions mentioned are added to the various products in amounts of 0.05 to 2 percent by weight, based on the entire product.
  • the claimed esters are furthermore distinguished by an extraordinarily good resistance to the odor. They do not develop any unpleasant odors even after the products perfumed with them have been stored for a long time.
  • the cyclopentyl and the cyclohexyl esters are particularly preferred for use under practical conditions because of their strong-smelling odor and their adhesive strength and at the same time great stability towards aggressive media.
  • Cyclohexyl salicylate was incorporated 1.5% in basic soap.
  • the forearm of a test person was foamed with the soap for 15 s 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.
  • the benzyl salicylate known as a fragrance was used. Radiance and adhesive strength were assessed according to the following scheme.
  • cyclohexyl salicylate 0.3% was incorporated as perfuming agent into the formulation of a commercially available laundry softener based on cationic quaternary ammonium compounds, emulsifiers, viscosity regulators, solvents and diluents.
  • 0.15% cyclohexyl salicylate 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)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fats And Perfumes (AREA)
  • Detergent Compositions (AREA)
  • Cosmetics (AREA)
  • Paper (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Chemical Or Physical Treatment Of Fibers (AREA)
  • Beans For Foods Or Fodder (AREA)
EP85900107A 1984-01-07 1984-12-14 Verwendung von salicylsäureestern als riechstoffe, diese enthaltende riechstoffkompositionen, sowie neue salicylsäureester Expired EP0168415B1 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT85900107T ATE28892T1 (de) 1984-01-07 1984-12-14 Verwendung von salicylsaeureestern als riechstoffe, diese enthaltende riechstoffkompositionen, sowie neue salicylsaeureester.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19843400342 DE3400342A1 (de) 1984-01-07 1984-01-07 Verwendung von salicylsaeureestern als riechstoffe, diese enthaltende riechstoffkompositionen, sowie neue salicylsaeureester
DE3400342 1984-01-07

Publications (2)

Publication Number Publication Date
EP0168415A1 EP0168415A1 (de) 1986-01-22
EP0168415B1 true EP0168415B1 (de) 1987-08-12

Family

ID=6224448

Family Applications (1)

Application Number Title Priority Date Filing Date
EP85900107A Expired EP0168415B1 (de) 1984-01-07 1984-12-14 Verwendung von salicylsäureestern als riechstoffe, diese enthaltende riechstoffkompositionen, sowie neue salicylsäureester

Country Status (15)

Country Link
US (1) US4624802A (es)
EP (1) EP0168415B1 (es)
JP (1) JPH0739589B2 (es)
AU (1) AU575115B2 (es)
BR (1) BR8407262A (es)
CA (1) CA1292238C (es)
DE (2) DE3400342A1 (es)
ES (1) ES8607207A1 (es)
GB (1) GB2152374B (es)
HK (1) HK93687A (es)
IT (1) IT1196379B (es)
MY (1) MY100883A (es)
SG (1) SG57087G (es)
WO (1) WO1985003084A1 (es)
ZA (1) ZA85104B (es)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024037712A1 (en) 2022-08-17 2024-02-22 Symrise Ag 1-cyclooctylpropan-2-one as a fragrance

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5298632A (en) * 1990-05-15 1994-03-29 Sumitomo Chemical Company, Limited Herbicidal pyrimidine compounds, compositions containing the same and method of use
US5232897A (en) * 1990-05-15 1993-08-03 Sumitomo Chemical Company, Limited Herbicidal pyrimidine compounds, compositions containing the same and method of use
AU645452B2 (en) * 1990-05-15 1994-01-13 Sumitomo Chemical Company, Limited Intermediate useful in the production of pyrimidine derivatives having herbicidal activity
CA2041615A1 (en) * 1990-05-15 1991-11-16 Mitsunori Hiratsuka Pyrimidine derivatives
DE4344358A1 (de) * 1993-12-24 1995-06-29 Henkel Kgaa Verfahren zum Aufarbeiten eines Reaktionsgemischs mittels einer auf den Reaktor aufgesetzen Kolonne
EP0694605B1 (fr) * 1994-07-01 1999-10-13 Firmenich Sa Diester cyclique et son utilisation à titre d'ingrédient parfumant
GB2303789A (en) * 1995-07-29 1997-03-05 Procter & Gamble Perfumed compositions containing formaldehyde generating preservatives
FR2740450B1 (fr) * 1995-10-27 2001-09-28 Rhone Poulenc Chimie Procede d'obtention de compositions parfumantes et de produits parfumes et produits ainsi obtenus
US6939835B2 (en) * 1999-03-26 2005-09-06 Firmenich Sa Cyclic compounds and their use as precursors of fragrant alcohols
DE10248952A1 (de) * 2002-10-21 2004-04-29 Bayer Ag Polycarbonate, Polyestercarbonate und Polyester mit lateral-ständigen Cycloalkyl-substituierten Phenolen
US6916899B2 (en) * 2002-10-21 2005-07-12 Bayer Aktiengesellschaft Polycarbonates, polyester carbonates and polyesters having lateral, cycloalkyl-substituted phenols
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
EP2046772A1 (en) * 2006-07-17 2009-04-15 Flexitral, Inc. Thiophenemethyl salicylate and related compounds as flavours and fragrances
CN105541634A (zh) * 2014-11-04 2016-05-04 南京秾康生物科技有限公司 一种胡莫柳酯的合成方法
CN112858650B (zh) * 2021-01-13 2023-08-18 上海应用技术大学 一种基于σ-τ强度法改善汽车革气味的分析研究方法

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE144002C (es) *
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
DE2247309A1 (de) * 1972-09-27 1974-04-25 Bayer Ag Verfahren zur herstellung von aromatischen o-hydroxycarbonsaeurealkylestern
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
JPS56108705A (en) * 1980-01-29 1981-08-28 Takasago Corp Perfume composition

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024037712A1 (en) 2022-08-17 2024-02-22 Symrise Ag 1-cyclooctylpropan-2-one as a fragrance

Also Published As

Publication number Publication date
WO1985003084A1 (fr) 1985-07-18
GB8500253D0 (en) 1985-02-13
SG57087G (en) 1987-09-18
ZA85104B (en) 1985-09-25
MY100883A (en) 1991-05-16
IT8424209A0 (it) 1984-12-21
HK93687A (en) 1987-12-18
GB2152374B (en) 1987-05-13
EP0168415A1 (de) 1986-01-22
DE3465333D1 (en) 1987-09-17
ES539388A0 (es) 1986-05-16
GB2152374A (en) 1985-08-07
CA1292238C (en) 1991-11-19
DE3400342A1 (de) 1985-07-18
JPH0739589B2 (ja) 1995-05-01
US4624802A (en) 1986-11-25
ES8607207A1 (es) 1986-05-16
BR8407262A (pt) 1985-12-24
AU3830985A (en) 1985-07-30
AU575115B2 (en) 1988-07-21
JPS60160040A (ja) 1985-08-21
IT1196379B (it) 1988-11-16

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