EP1061125A2 - Compositions contenant du di(2-ethylhexyl)adipate et des composés tricycliques d'isochromane et leur utilisation dans des détergents et adoucissants à enzymes actifs - Google Patents

Compositions contenant du di(2-ethylhexyl)adipate et des composés tricycliques d'isochromane et leur utilisation dans des détergents et adoucissants à enzymes actifs Download PDF

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Publication number
EP1061125A2
EP1061125A2 EP00304546A EP00304546A EP1061125A2 EP 1061125 A2 EP1061125 A2 EP 1061125A2 EP 00304546 A EP00304546 A EP 00304546A EP 00304546 A EP00304546 A EP 00304546A EP 1061125 A2 EP1061125 A2 EP 1061125A2
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EP
European Patent Office
Prior art keywords
adipate
fabric
ethyl hexyl
mixture
tricyclic
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.)
Withdrawn
Application number
EP00304546A
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German (de)
English (en)
Other versions
EP1061125A3 (fr
Inventor
Cornelia Elisabeth Maria Meesters
Jens Joannicus Christiaanse
Jan Tijmen Van Elst
Henricus Gerardus Maria Reijmer
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.)
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Publication date
Application filed by International Flavors and Fragrances Inc filed Critical International Flavors and Fragrances Inc
Publication of EP1061125A2 publication Critical patent/EP1061125A2/fr
Publication of EP1061125A3 publication Critical patent/EP1061125A3/fr
Withdrawn legal-status Critical Current

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    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/005—Compositions containing perfumes; Compositions containing deodorants
    • 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
    • C11B9/0069—Heterocyclic compounds
    • C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
    • C11B9/008—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing six atoms
    • 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
    • C11D3/16—Organic compounds
    • C11D3/38—Products with no well-defined composition, e.g. natural products
    • C11D3/386—Preparations containing enzymes, e.g. protease or amylase
    • C11D3/38627—Preparations containing enzymes, e.g. protease or amylase containing lipase
    • 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

Definitions

  • Our invention relates to the field of perfumery and, more particularly, to improved fragranced detergents and fabric softeners.
  • GALAXOLIDE® trademark of International Flavors & Fragrances Inc. of New York, New York
  • GALAXOLIDE® trademark of International Flavors & Fragrances Inc. of New York, New York
  • GALAXOLIDE® has extremely high viscosity and at lower temperatures exists in the crystalline state making it difficult for incorporation into fragrances.
  • the GALAXOLIDE® has been combined with other materials in order to form "eutectic" compositions containing GALAXOLIDE® and other materials, for example, benzophenone.
  • 5,649,979 indicates that a "novel" solution to the problem has been achieved where a process for perfuming textiles washed with detergents containing lipases has been discovered.
  • U.S. Letters Patent No. 5,649,979 establishes that by adding particular ingredients to the fabric detergent and/or fabric softener that is subsequently applied, one could distinctly improve the odor of the fabrics treated with these products and prolong the fragrance of the fabrics after drying.
  • U.S. Letters Patent No. 5,649,979 provides a process for perfuming fabrics washed in the presence of a lipase-containing detergent and, optionally, subsequently treated with a fabric softener with the process being characterized in that the detergent and/or fabric softener contains a compound of the formula: wherein:
  • Our invention concerns a process for the creation of a liquid fragrance composition that is easily used in forming still further liquid fragrance compositions, containing GALAXOLIDE®, a mixture of compounds having the structures: comprising the steps of admixing a sufficient quantity of di(2-ethyl hexyl) adipate with substantially pure GALAXOLIDE®, thereby creating a composition in the liquid phase having a viscosity in the range of from about 180 centipoises (cps) up to about 250 cps at 25°C.
  • cps centipoises
  • our invention is directed to a mixture consisting essentially of:
  • Our invention is further directed to a laundry detergent or fabric softener comprising the above-identified perfuming composition as an active perfume ingredient.
  • Our invention is further directed to a method for perfuming fabrics which comprises washing the fabrics in the presence of a lipase-containing detergent and, optionally, subsequently treating the fabric with a fabric softener wherein the detergent or fabric softener comprises as an active perfume ingredient the above-identified range of mixtures of tricyclic isochroman compounds having the structures: and di(2-ethyl hexyl) adipate having the structure: with the range of weight ratios of tricyclic isochroman:di(2-ethyl hexyl) adipate being from about 1:1 up to about 3:1.
  • C log 10 P the calculated log 10 [n-octanol/water partition coefficient]
  • C log 10 P the calculated log 10 [n-octanol/water partition coefficient]
  • the standard for the optimum GALAXOLIDE® aroma is for the main peak of the GALAXOLIDE® (that is for the presence of the compound having the structure: to be between 52% and 56% by weight of all components obtained in a GLC (liquid chromatography) sample.
  • GLC liquid chromatography
  • the mixture of GALAXOLIDE® and di(2-ethyl hexyl) adipate in combination provides a new aroma containing notes of both 2-ethyl hexanol and GALAXOLIDE®, but also enables the GALAXOLIDE® to be used in much greater proportions than has been used before, for example, with diethyl phthalate.
  • the process of our invention is advantageous whenever other fragrance compounds are also used which show a weak tenacity on fabrics and which are compatible from an olfactory standpoint with GALAXOLIDE® and 2-ethyl hexanol.
  • the GALAXOLIDE® - di(2-ethyl hexyl) adipate of our invention can be added to detergents and fabric softeners either as such or in admixture with other perfuming ingredients, solvents or adjuvants of current use in perfumery.
  • concentrations in which they can be added to the detergents and fabric softeners according to the inventions have the values usual in the art for this type of product. The skilled person in the art is quite able to select such values as a function of the nature of the product to be perfumed and of the desired olfactive effect.
  • concentrations of the order of from about 0.005 up to about 7% by weight of the mixture of GALAXOLIDE® and di(2-ethyl hexyl) adipate relative to the weight of detergent and/or fabric softener composition are useful.
  • the fabric detergents and softeners can take the form of powders or granular solids, bars, pastes as well as aqueous or non-aqueous liquids and contain the usual ingredients for this type of product.
  • the detergents can typically contain, in addition to the lipase enzyme (as specifically disclosed in European Patent No. 430,315) active anionic, cationic, nonionic or zwitterionic surfactants as well as filling agents, bleaching agents, confining agents and other ingredients of current use in the detergent bases intended for washing cloth such as linen.
  • lipase enzyme as specifically disclosed in European Patent No. 430,315
  • active anionic, cationic, nonionic or zwitterionic surfactants as well as filling agents, bleaching agents, confining agents and other ingredients of current use in the detergent bases intended for washing cloth such as linen.
  • a base detergent of this type to which there is added the lipase in the desired concentrations can have the following composition (origin: Henkel KGaA of Düsseldorf, Germany): Ingredients Parts by Weight Linear sodium alkyl benzene sulfonate (average length of the alkyl chain: C 11.5 ) 8.0 Ethoxylated tallow alcohol 2.9 Sodium triphosphate 43.8 Sodium silicate 7.5 Magnesium silicate 1.9 Carboxymethylcellulose 1.2 Sodium ethylenediaminetetraacetate 0.2 Sodium sulfate 21.2 Water 13.3 Total 100.0
  • the peak indicated by reference numeral 10 is the peak for the compound having the structure:
  • the peak indicated by reference numeral 12 is the peak for the di(2-ethyl hexyl) adipate.
  • the peak indicated by reference numeral 20 is the peak for the compound having the structure:
  • the peak indicated by reference numeral 22 is the peak for the di(2-ethyl hexyl) adipate
  • the Y axis for the GLC percent for the main peak of GALAXOLIDE® is indicated by reference numeral 36 and the weight percent GALAXOLIDE® (undiluted) on the X axis is indicated by reference numeral 35 .
  • the graph indicated by reference numeral 30 is the graph for the mixtures of GALAXOLIDE® and diethyl phthalate having the structure:
  • the graph indicated by reference numeral 32 is the graph for mixtures of GALAXOLIDE® and di(2-ethyl hexyl) adipate.
  • the graph indicated by reference numeral 34 is the graph for mixtures of GALAXOLIDE® and 2-ethyl hexyl benzoate having the structure:
  • a standard cotton swatch of 32 grams is placed in a LINITEST® type vessel containing 1.3 grams of a standard powder detergent base comprising 1% by weight of lipase (LIPOLASE® 100T manufactured by Novo Nordisk S.A. of Denmark) and 260 ml water.
  • the cotton swatch is washed for 30 minutes at 40°C. It is then taken out of the vessel and rinsed with 3 x 200 ml portions of water.
  • a fabric softener base which contains a certain percentage by weight comprised between 0.5 and 1% of a mixture of GALAXOLIDE® and di(2-ethyl hexyl) adipate or, when applicable, of the corresponding alcohol which is 2-ethyl hexanol-1.
  • the cotton swatch is then spin-dried without having been used and dried on a clothes line.
  • This method is equivalent to a washing in a real machine for washing 5 kg of linen in approximately 20 liters of water with a rinsing of 4 x 20 liters of water, the fabric softener being applied in the last rinsing water.
  • the fabric softener base used has the following compositions: Ingredients Parts by Weight ARQUAD® 2HT (75%) (trademark of Akzo Corporation of the Netherlands) 5.00 Formalin (40%) 0.20 Demineralized water 94.80 Total 100.00
  • the cotton swatches were treated according to this general method, using as an additive to the fabric softener, respectively, (i) a 2:1 mixture of GALAXOLIDE®:di(2-ethyl hexyl) adipate, 1% in test A ; and (ii) a 2:1 weight:weight mixture of GALAXOLIDE®:2-ethyl hexanol-1 in test B .
  • the two swatches were submitted for a blind panel test evaluation 24 hours after having been taken out of the LINITEST® apparatus. Each member of the panel is then requested to smell a strip which had been dipped into 2-ethyl hexanol-1 in order to cause them to be familiar with the odor of this particular component. Each member of the panel was then asked to smell the two cotton swatches as set forth above and state whether they detect the nuances of (i) 2-ethyl hexanol-1 and (ii) GALAXOLIDE®.
  • a base perfume composition is prepared by admixing the following ingredients: Ingredients Percent by Weight Vetiver Venezuela 30 Phenylethyl alcohol 25 Benzylpropionate 20 10-Undecenal 8 Hexylcinnamic aldehyde 80 Methyl anthranilate 20 Verdyl acetate 30 Trans, trans- ⁇ -damascone 12 Eugenol 8 Isoeugenol 20 Orange essential oil 25 Benzylsalicylate 40 Phenylsalicylate 25 ⁇ -Terpeniol 20
  • compositions are prepared with the aforementioned base as follows:
  • compositions are then each added at the rate of 0.7% by weight to a non-perfumed fabric softener base to prepare two samples: A and B of a perfumed softener.
  • each batch of textiles was sampled by a blind panel of 25 individuals. Each member of the blind panel identified the aroma of the batch treated with perfumed softener samples A and B.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Textile Engineering (AREA)
  • Detergent Compositions (AREA)
EP00304546A 1999-06-18 2000-05-30 Compositions contenant du di(2-ethylhexyl)adipate et des composés tricycliques d'isochromane et leur utilisation dans des détergents et adoucissants à enzymes actifs Withdrawn EP1061125A3 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US33605499A 1999-06-18 1999-06-18
US336054 1999-06-18

Publications (2)

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EP1061125A2 true EP1061125A2 (fr) 2000-12-20
EP1061125A3 EP1061125A3 (fr) 2002-11-13

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1447077A1 (fr) * 2003-02-10 2004-08-18 INTERNATIONAL FLAVORS & FRAGRANCES INC. Composition solide de benzopyrane, procédé pour sa préparation et son utilisation organoleptique
WO2008104352A2 (fr) * 2007-02-26 2008-09-04 Givaudan Nederland Services B.V. Compositions de parfum
WO2020260598A1 (fr) 2019-06-27 2020-12-30 Firmenich Sa Produits de consommation parfumés

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0430315A2 (fr) * 1989-09-29 1991-06-05 Unilever N.V. Compositions détegentes parfumées
US5494892A (en) * 1994-03-17 1996-02-27 International Flavors & Fragrances Inc. Methyl substituted propyl-substituted pentamethyl indane derivatives processes for producing same and perfumery uses thereof
WO1997017419A1 (fr) * 1995-11-07 1997-05-15 Quest International Composition assouplissante pour textiles
US5649979A (en) * 1993-08-09 1997-07-22 Firmenich S.A. Process for perfuming textiles
WO1998056337A1 (fr) * 1997-06-09 1998-12-17 The Procter & Gamble Company Composition desodorisante contenant du musc et de l'ambre
US5891449A (en) * 1993-10-21 1999-04-06 Stockhausen Gmbh & Co. Kg Skin cleaning agents, a process for their production and their use

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0430315A2 (fr) * 1989-09-29 1991-06-05 Unilever N.V. Compositions détegentes parfumées
US5649979A (en) * 1993-08-09 1997-07-22 Firmenich S.A. Process for perfuming textiles
US5891449A (en) * 1993-10-21 1999-04-06 Stockhausen Gmbh & Co. Kg Skin cleaning agents, a process for their production and their use
US5494892A (en) * 1994-03-17 1996-02-27 International Flavors & Fragrances Inc. Methyl substituted propyl-substituted pentamethyl indane derivatives processes for producing same and perfumery uses thereof
WO1997017419A1 (fr) * 1995-11-07 1997-05-15 Quest International Composition assouplissante pour textiles
WO1998056337A1 (fr) * 1997-06-09 1998-12-17 The Procter & Gamble Company Composition desodorisante contenant du musc et de l'ambre

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1447077A1 (fr) * 2003-02-10 2004-08-18 INTERNATIONAL FLAVORS & FRAGRANCES INC. Composition solide de benzopyrane, procédé pour sa préparation et son utilisation organoleptique
US7407928B2 (en) 2003-02-10 2008-08-05 International Flavors & Fragrances Inc. Solid phase benzopyran composition, process for preparing same and organoleptic uses thereof
CN1520801B (zh) * 2003-02-10 2012-07-18 国际香料和香精公司 固相苯并吡喃组合物，其制备方法和其感官用途
WO2008104352A2 (fr) * 2007-02-26 2008-09-04 Givaudan Nederland Services B.V. Compositions de parfum
WO2008104352A3 (fr) * 2007-02-26 2009-01-15 Quest Int Serv Bv Compositions de parfum
WO2020260598A1 (fr) 2019-06-27 2020-12-30 Firmenich Sa Produits de consommation parfumés

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