US3325369A - Perfume compositions containing geranonitrile, cinnamyl nitrile or 2-nonenyl nitrile - Google Patents

Perfume compositions containing geranonitrile, cinnamyl nitrile or 2-nonenyl nitrile Download PDF

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Publication number
US3325369A
US3325369A US355071A US35507164A US3325369A US 3325369 A US3325369 A US 3325369A US 355071 A US355071 A US 355071A US 35507164 A US35507164 A US 35507164A US 3325369 A US3325369 A US 3325369A
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US
United States
Prior art keywords
nitrile
geranonitrile
odor
nonenyl
mixtures
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 - Lifetime
Application number
US355071A
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English (en)
Inventor
Willard T Somerville
Edward J Shuster
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.)
International Flavors and Fragrances Inc
Original Assignee
International Flavors and Fragrances Inc
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
Priority to NL136826D priority Critical patent/NL136826C/xx
Application filed by International Flavors and Fragrances Inc filed Critical International Flavors and Fragrances Inc
Priority to US355071A priority patent/US3325369A/en
Priority to GB17209/64A priority patent/GB1018836A/en
Priority to FR972656A priority patent/FR1392973A/fr
Priority to DEJ25748A priority patent/DE1213942B/de
Priority to BE647423D priority patent/BE647423A/xx
Priority to NL6404880A priority patent/NL6404880A/xx
Priority to CH574264A priority patent/CH436541A/de
Application granted granted Critical
Publication of US3325369A publication Critical patent/US3325369A/en
Priority to NL6918946A priority patent/NL6918946A/xx
Priority to NL6918947A priority patent/NL6918947A/xx
Priority to US27332D priority patent/USRE27332E/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L9/00—Disinfection, sterilisation or deodorisation of air
    • A61L9/01—Deodorant compositions
    • 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
    • C11B9/0007—Aliphatic compounds
    • C11B9/0023—Aliphatic compounds containing nitrogen as the only heteroatom
    • 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
    • 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
    • C11B9/0065—Nitriles
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50—Perfumes
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D9/00—Compositions of detergents based essentially on soap
    • C11D9/04—Compositions of detergents based essentially on soap containing compounding ingredients other than soaps
    • C11D9/44—Perfumes; Colouring materials; Brightening agents ; Bleaching agents
    • C11D9/442—Perfumes

Definitions

  • Soaps and similar compositions are generally blended with perfume mixtures containing at least one ingredient selected to impart a pleasing odor. Often o e-unsaturated aldehydes are used to impart the desired odor. It has been found that one of the most pleasant and acceptable odors is the fresh, citrusy, lemon-like odor which is obtained by blending citral either alone or as an ingredient in a perfume mixture in soaps and like compositions. Other desirable odors are imparted with other aldehydes such as cinnamaldehyde and 2-nonenyl aldehyde.
  • citral and other such aldehydes have poor stability.
  • citral when incorporated in various compositions either alone or in a mixture discolors on standing and its odor becomes degraded.
  • the principal object of the our invention accordingly, is to find a substitute for .u o-unsaturated aldehydes such as citral which, while possessing the desirable characteristics of the aldehydes can be blended in the compositions mentioned either alone or as part of a perfume mixture without substantial deterioration with respect to odor, color or other desirable qualities.
  • citral has the desired citr-usy, lemon-like odor of citral and when blended in compositions including soap, detergents, cosmetics, space deodorants and the like, shows substantially no discoloration or degradation of odor on storage for long periods of time.
  • cinnamonitrile has the quality characteristic of cinnamaldehyde, but with a special green top note. In soap and other compositions, it is decidedly superior to the corresponding aldehyde in both color and odor stability.
  • 2-nonenyl nitrile has the cinnamon-like characteristics of the corresponding aldehyde.
  • the fragrance quality of the latter disappears so rapidly in all media that it is worthless as a perfume.
  • the nitrile is stable and retains its fragrance characteristics as a perfume and in perfume mixtures when used in compositions such as soaps, powders and others as referred to above.
  • the invention comprises the novel products, the specific embodiments of which are described hereinafter by way of example and in accordance with which we now prefer to practice the invention.
  • Cinnamonitrile and 2-nonenyl nitrile are prepared in accordance with standard procedures for example from the corresponding oxime and may be obtained either as pure isomers or as mixtures of cis and trans forms. Whether utilized as isomers or as mixtures, the compounds are re markably stable in odor and color.
  • nitriles may be utilized alone, as above stated, for example in sachets for use in bureaus and in closets, and in other ways that compositions are normally employed. They may also be employed alone or in mixtures in detergents, cosmetics, soaps, space deodorants and other formulations.
  • geranonitrile may be combined with soaps which have an alkaline reaction in use, or.in some detergents which have an acid reaction, without changing. its stability with respect to color or odor.
  • Compositions of this sort which include geranonitrile have an extremely long shelf life, while citral, when included in the same compositions, has a relatively short shelf life, as shown by the test below. Similar results are obtained with the nitriles mentioned above and similar nitriles.
  • soap chips were mixed with one gram of the perfume mixture given below until a substantially homogeneous composition was obtained.
  • Another soap composition- was identically prepared except that the geranonitrile of the perfume mixture was replaced with three times the amount of citr-al. Both soap compositions manifested a characteristic lemon-like odor despite the lesser amount of geranonitrile employed.
  • the perfume mixture consisted of the following ingredients in the parts by weight indicated:
  • Example II - Testing of soups containing geranortitrile containers in an oven at 140 F. for five days, after which they were compared with duplicate samples kept in closed containers at room temperature. In all cases, soaps containing citral were discolored. The odor of citral was al-' ready in the process of degradation. In contrast, the soaps containing geranonitrile were unchanged both in color and odor.
  • Example IlI.Preparation of detergent compositions containing geranonitrile A total of 100 grams of a detergent were mixed with 0.15 gram of the perfume mixture given below until a substantially homogeneous composition was obtained. Other detergent compositions were similarly prepared ex- 'cept that the geranonitrile was replaced with three times the amount of citral. Both compositions manifested a characteristic lemon-like odor of substantially equal strength despite the lesser amount of geranonitrile used.
  • compositions were identically tested in accordance with the procedure described in Example II with the same results.
  • the perfume mixture used in preparing the detergents of this example consisted of the following ingredients in parts by weight indicated:
  • Example VII -Liquid detergent containing cinnamonitrile Concentrated liquid detergent samples containing, in the one case 0.2% by weight of cinnamonitrile and in the other 0.2% by weight of cinnamaldehyde were held at room temperature for ten days and compared with one another. At the end of this period an examination showed that the nitrile imparted a more powerful cassia note than the aldehyde, and that with the nitrile there was no change Terpinyl acetate a 100 Terpineol 40 Linalyl acetate 100 Orange oil 350 Geranyl acetate 100 Geraniol Coumarin 2 Geranonitrile 3.5
  • Example IV Preparation of cosmetic powder composition containing geranonitrile
  • a cosmetic powder was prepared by mixing 100 grams of powder with 0.25 gram of geranonitrile in a ball mill.
  • a second cosmetic powder was similarly prepared except that the geranonitrile was replaced with citral.
  • Example VI oilet soap composition with a perfume composition containing cinnamonitrile
  • a perfume mixture containing the following ingredients in the parts by weight indicated was prepared:
  • the detergent samples were further tested under use conditions by dissolving 0.5 gram of the perfumed detergents in separate 200 gram portions of warm water.
  • the detergent containing the aldehyde in water exhibited evidence of degradation by change of the characteristic odor and loss of such odor, whereas the comparable nitrile-containing composition retained its full strong cinamon-like odor, without loss of color, whereas the aldehyde containing composition exhibited a yellowish discoloration.
  • Example VIII -Powder detergent containing cinnamonitrile
  • a comparison experiment was carried out in which detergent base powder samples containing 0.2 gram of cinnamaldehyde or 0.2 gram of cinnamonitrile per grams of unperfumed detergent base powder were thoroughly mixed in a high speed rotary roller blender. The samples were examined after 10 days storage in closed glass containers at room temperature. It was found that the odor of the aldehyde had lost its characteristics very rapidly, and that the powder had acquired a yellowish cast. The sample containing the nitrile retained its typical cinnamon note in full volume, and there was no change in color.
  • Example IX --Cosmetic powder containing cinnamonitrile
  • cosrnetic talcum powder samples containing one gram of cinnamaldehyde or one gram of cinnamonitrile per 100 grams of unperfumed talcum powder were thoroughly mixed in a high speed rotary blender. The samples were stored in closed glass containers in an oven for one week at 100 F. In this medium the aldehyde note was completely altered and the talcum powder acquired a pale, ivory tint, whereas the nitrile retained its typical note with no discoloration of the powder base.
  • Example X .C0smetic powder containing trans-Z-nonenyl nitrile Separate mixtures, used as described in the following paragraph, were prepared containing one part trans-2- 'nonenyl nitrile in 1,000 parts of methyl ionone and one part trans-Z-nonenal in 1,000 parts of the same substance.
  • Example XI.Sap bars containing trans-Z-nonenyl nitrile Separate mixtures were prepared containing one part trans-Z-nonenyl nitrile in 1,000 parts para tertiary amyl cyclohexanone and one part trans-Z-nonenal in 1,000 parts of the same substance.
  • nitriles in cosmetic powders is an especially rigorous test of their stability, since in powders, degradation due to oxidation is accelerated because of the enormous surface area of the powder.
  • nitrile which will be effective in our compositions depends upon many factors, including for example, the selected nitrile, the other ingredients present, their amounts and the effects which are desired.
  • perfume mixtures containing as little as 0.02% by weight of nitrile or even less may be usefully employed. For certain mixtures as much as 12% by Weight or even higher is useful.
  • these perfume mixtures are used in soaps and other products the amount is the same as is generally employed with ordinary perfume mixtures, i.e., from about 1% to about 3% by weight.
  • 0.0002% 'by weight of the selected nitrile may be employed to impart desirable aroma characteristics to soaps, cosmetics and other products.
  • the soap base and soap chips used consisted of unperfumed sodium base toilet soap made from tallow and coconut oil.
  • detergent powder was a powder obtained from Lever Bros, Co. being sold under the trademark Rinso.
  • liquid detergent was a product manufactured by Ultra Chemical Co., known as P-87 Liquid Detergent Base.
  • a composition comprising a soap together with a perfume mixture containing an effective amount of a nitrile selected from the group consisting of geranonitrile, cinnamyl nitrile, 2-nonenyl nitrile and mixtures thereof characterized by substantial freedom from discoloration and odor degradation on storage.
  • a nitrile selected from the group consisting of geranonitrile, cinnamyl nitrile, 2-nonenyl nitrile and mixtures thereof characterized by substantial freedom from discoloration and odor degradation on storage.
  • a composition comprising a detergent together with a perfume mixture containing an effective amount of a nitrile selected from the group consisting of geranonitrile, cinnamyl nitrile, 2-nonenyl nitrile and mixtures thereof characterized by substantial freedom from discoloration and odor degradation on storage.
  • a nitrile selected from the group consisting of geranonitrile, cinnamyl nitrile, 2-nonenyl nitrile and mixtures thereof characterized by substantial freedom from discoloration and odor degradation on storage.
  • a composition comprising a cosmetic together with a perfume mixture containing an effective amount of a nitrile selected from the group consisting of geranonitrile, cinnamyl nitrile, 2.-nonenyl nitrile and mixtures thereof characterized by substantial freedom from discoloration and odor degradation on storage.
  • a nitrile selected from the group consisting of geranonitrile, cinnamyl nitrile, 2.-nonenyl nitrile and mixtures thereof characterized by substantial freedom from discoloration and odor degradation on storage.
  • a composition comprising a space deodorant together With a perfume mixture containing an effective amount of a nitrile selected from the group consisting of geranonitrile, cinnamyl nitrile, 2-nonenyl nitrile and mixtures thereof characterized by substantial freedom from discoloration and odor degradation on storage.
  • a nitrile selected from the group consisting of geranonitrile, cinnamyl nitrile, 2-nonenyl nitrile and mixtures thereof characterized by substantial freedom from discoloration and odor degradation on storage.
  • a perfume consisting of a mixture of cis and trans isomers of geranonitrile having a citrusy lemon-like odor substantially identical with that of citral but substantially free from discoloration and odor degradation.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Fats And Perfumes (AREA)
  • Detergent Compositions (AREA)
US355071A 1963-05-03 1964-03-26 Perfume compositions containing geranonitrile, cinnamyl nitrile or 2-nonenyl nitrile Expired - Lifetime US3325369A (en)

Priority Applications (11)

Application Number Priority Date Filing Date Title
NL136826D NL136826C (enrdf_load_stackoverflow) 1963-05-03
US355071A US3325369A (en) 1963-05-03 1964-03-26 Perfume compositions containing geranonitrile, cinnamyl nitrile or 2-nonenyl nitrile
GB17209/64A GB1018836A (en) 1963-05-03 1964-04-24 Perfume compositions
FR972656A FR1392973A (fr) 1963-05-03 1964-04-28 Perfectionnements apportés aux compositions parfumées utilisables dans des savons, cosmétiques, désodorisants d'atmosphère et analogues
BE647423D BE647423A (enrdf_load_stackoverflow) 1963-05-03 1964-04-30
DEJ25748A DE1213942B (de) 1963-05-03 1964-04-30 Riechstoffzusammensetzung
NL6404880A NL6404880A (enrdf_load_stackoverflow) 1963-05-03 1964-05-01
CH574264A CH436541A (de) 1963-05-03 1964-05-01 Verwendung von neuen Nitrilen als Duftstoffe
NL6918946A NL6918946A (enrdf_load_stackoverflow) 1963-05-03 1969-12-17
NL6918947A NL6918947A (enrdf_load_stackoverflow) 1963-05-03 1969-12-17
US27332D USRE27332E (en) 1963-05-03 1970-03-23 Perfume compositions containing geranonitrile, cinnamyl nitrile or z-nonenyl nitrile

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US27769563A 1963-05-03 1963-05-03
US355071A US3325369A (en) 1963-05-03 1964-03-26 Perfume compositions containing geranonitrile, cinnamyl nitrile or 2-nonenyl nitrile
US2207270A 1970-03-23 1970-03-23

Publications (1)

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US3325369A true US3325369A (en) 1967-06-13

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Family Applications (2)

Application Number Title Priority Date Filing Date
US355071A Expired - Lifetime US3325369A (en) 1963-05-03 1964-03-26 Perfume compositions containing geranonitrile, cinnamyl nitrile or 2-nonenyl nitrile
US27332D Expired USRE27332E (en) 1963-05-03 1970-03-23 Perfume compositions containing geranonitrile, cinnamyl nitrile or z-nonenyl nitrile

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Application Number Title Priority Date Filing Date
US27332D Expired USRE27332E (en) 1963-05-03 1970-03-23 Perfume compositions containing geranonitrile, cinnamyl nitrile or z-nonenyl nitrile

Country Status (6)

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US (2) US3325369A (enrdf_load_stackoverflow)
BE (1) BE647423A (enrdf_load_stackoverflow)
CH (1) CH436541A (enrdf_load_stackoverflow)
DE (1) DE1213942B (enrdf_load_stackoverflow)
GB (1) GB1018836A (enrdf_load_stackoverflow)
NL (4) NL6404880A (enrdf_load_stackoverflow)

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2604655A1 (de) * 1975-02-11 1976-08-19 Naarden International Nv Verfahren zur herstellung von riechstoffkompositionen
DE2910282A1 (de) * 1978-03-20 1979-10-04 Unilever Nv Nicht keimtoetende, desodorierende toiletteseife, verfahren zu ihrer herstellung und ihre verwendung
US4277377A (en) * 1979-03-22 1981-07-07 Bush Boake Allen Limited Perfume compositions containing dimethyl heptenonitriles
US4863631A (en) * 1988-06-24 1989-09-05 International Flavors & Fragrances Inc. Dimethyl substituted alkyl nitriles, perfume and bleach compositions containing same organoleptic uses thereof and process intermediates for producing same
US4962089A (en) * 1988-11-18 1990-10-09 International Flavors & Fragrances Inc. Cyano-substituted sulfur-containing compounds, and compositions containing same and organoleptic uses thereof
US4983579A (en) * 1988-11-18 1991-01-08 International Flavors & Fragrances Inc. Cyano-substituted sulfur containing compounds, compositions containing same, processes for preparing same and organoleptic uses thereof
US4985402A (en) * 1990-04-25 1991-01-15 International Flavors & Fragrances Inc. 2-Methyl-1-nitrilo-2-methyl -1-hydroxylamino-3-(methoxyphenyl) propane, organoleptic uses thereof and processes for preparing same
US5105005A (en) * 1989-09-28 1992-04-14 Haarmann & Reimer Gmbh Alkadienenitriles, process for their preparation and their use
WO2000001360A1 (en) * 1998-07-07 2000-01-13 Quest International B.V. Perfume compositions
EP1174117A1 (en) * 2000-07-21 2002-01-23 Givaudan SA Fragrance composition comprising a mixture of nitriles
EP1174116A1 (en) * 2000-07-21 2002-01-23 Givaudan SA Fragrance composition comprising a mixture of nitriles
US20070231885A1 (en) * 2005-12-09 2007-10-04 Norcal Waste Systems, Inc. Biomechanical device for producing a biomass
US20070231877A1 (en) * 2003-04-30 2007-10-04 Norcal Waste Systems, Inc. Systems and processes for treatment of organic waste materials with a biomixer
KR100818139B1 (ko) * 1999-10-08 2008-03-31 가부시키가이샤 시세이도 피부면역기능 조절제
US7955839B2 (en) 2006-06-23 2011-06-07 Recology Inc. Systems and methods for converting organic waste materials into useful products
US8809038B1 (en) 2003-04-30 2014-08-19 Recology Inc. Process for treatment of organic waste materials
WO2015048163A1 (en) * 2013-09-25 2015-04-02 Takasago International Corp. (Usa) (6z)-non-6-enenitrile as a fragrance and flavor material

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1534132A (en) 1975-12-11 1978-11-29 Polak Frutal Works Alpha beta-disubstituted conjugated nitriles for perfume use
CA1174694A (en) 1981-09-03 1984-09-18 Charles S. Sell Aliphatic nitriles
US5143899A (en) * 1991-09-13 1992-09-01 International Flavors & Fragrances Inc. Process for preparing phenyl butyronitriles and perfumery use of 2,2-dimethyl-4-phenyl valeronitrile
EP0780132B1 (en) * 1995-12-21 2002-07-24 INTERNATIONAL FLAVORS & FRAGRANCES INC. Malodor counteractant composition and process for using same
US7361630B2 (en) * 2005-09-07 2008-04-22 International Flavors & Fragranies Inc. Alkyl substituted octennitrile derivatives

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
None *

Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2604655A1 (de) * 1975-02-11 1976-08-19 Naarden International Nv Verfahren zur herstellung von riechstoffkompositionen
JPS51104044A (en) * 1975-02-11 1976-09-14 Naarden International Nv Kosuisoseibutsunoseiho
DE2910282A1 (de) * 1978-03-20 1979-10-04 Unilever Nv Nicht keimtoetende, desodorierende toiletteseife, verfahren zu ihrer herstellung und ihre verwendung
US4277377A (en) * 1979-03-22 1981-07-07 Bush Boake Allen Limited Perfume compositions containing dimethyl heptenonitriles
US4863631A (en) * 1988-06-24 1989-09-05 International Flavors & Fragrances Inc. Dimethyl substituted alkyl nitriles, perfume and bleach compositions containing same organoleptic uses thereof and process intermediates for producing same
US4962089A (en) * 1988-11-18 1990-10-09 International Flavors & Fragrances Inc. Cyano-substituted sulfur-containing compounds, and compositions containing same and organoleptic uses thereof
US4983579A (en) * 1988-11-18 1991-01-08 International Flavors & Fragrances Inc. Cyano-substituted sulfur containing compounds, compositions containing same, processes for preparing same and organoleptic uses thereof
US5105005A (en) * 1989-09-28 1992-04-14 Haarmann & Reimer Gmbh Alkadienenitriles, process for their preparation and their use
US4985402A (en) * 1990-04-25 1991-01-15 International Flavors & Fragrances Inc. 2-Methyl-1-nitrilo-2-methyl -1-hydroxylamino-3-(methoxyphenyl) propane, organoleptic uses thereof and processes for preparing same
WO2000001360A1 (en) * 1998-07-07 2000-01-13 Quest International B.V. Perfume compositions
US6475473B1 (en) 1998-07-07 2002-11-05 Quest International B.V. Perfume compositions
KR100818139B1 (ko) * 1999-10-08 2008-03-31 가부시키가이샤 시세이도 피부면역기능 조절제
JP2002080886A (ja) * 2000-07-21 2002-03-22 Givaudan Sa ニトリルの混合物を含む芳香組成物
EP1174116A1 (en) * 2000-07-21 2002-01-23 Givaudan SA Fragrance composition comprising a mixture of nitriles
US6743768B2 (en) 2000-07-21 2004-06-01 Givaudan Sa Fragrance composition comprising a mixture of nitriles
EP1174117A1 (en) * 2000-07-21 2002-01-23 Givaudan SA Fragrance composition comprising a mixture of nitriles
US20070231877A1 (en) * 2003-04-30 2007-10-04 Norcal Waste Systems, Inc. Systems and processes for treatment of organic waste materials with a biomixer
US7985577B2 (en) 2003-04-30 2011-07-26 Recology, Inc. Systems and processes for treatment of organic waste materials with a biomixer
US8809038B1 (en) 2003-04-30 2014-08-19 Recology Inc. Process for treatment of organic waste materials
US20070231885A1 (en) * 2005-12-09 2007-10-04 Norcal Waste Systems, Inc. Biomechanical device for producing a biomass
US7955839B2 (en) 2006-06-23 2011-06-07 Recology Inc. Systems and methods for converting organic waste materials into useful products
WO2015048163A1 (en) * 2013-09-25 2015-04-02 Takasago International Corp. (Usa) (6z)-non-6-enenitrile as a fragrance and flavor material
JP2016540100A (ja) * 2013-09-25 2016-12-22 高砂香料工業株式会社 フレグランス原料及び香料原料としての（６ｚ）−６−ノネンニトリル
US10017711B2 (en) 2013-09-25 2018-07-10 Takasago International Corporation (6Z)-non-6-enenitrile as a fragrance and flavor material

Also Published As

Publication number Publication date
NL136826C (enrdf_load_stackoverflow)
BE647423A (enrdf_load_stackoverflow) 1964-10-30
DE1213942B (de) 1966-04-07
USRE27332E (en) 1972-04-11
NL6918947A (enrdf_load_stackoverflow) 1970-03-23
CH436541A (de) 1967-05-31
GB1018836A (en) 1966-02-02
NL6404880A (enrdf_load_stackoverflow) 1964-11-04
NL6918946A (enrdf_load_stackoverflow) 1970-03-23

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