EP2129758A2 - Parfüm-zusammensetzungen - Google Patents

Parfüm-zusammensetzungen

Info

Publication number
EP2129758A2
EP2129758A2 EP08716029A EP08716029A EP2129758A2 EP 2129758 A2 EP2129758 A2 EP 2129758A2 EP 08716029 A EP08716029 A EP 08716029A EP 08716029 A EP08716029 A EP 08716029A EP 2129758 A2 EP2129758 A2 EP 2129758A2
Authority
EP
European Patent Office
Prior art keywords
methyl
group
weight
lipase
ingredients
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Withdrawn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
EP08716029A
Other languages
English (en)
French (fr)
Inventor
Paula Maria Cawkill
Roger John Henry Duprey
Jeremy Nicholas Ness
David Jonathan Bradshaw
Michael Steven Watson
John Martin Behan
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.)
Givaudan Nederland Services BV
Original Assignee
Givaudan Nederland Services BV
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 Givaudan Nederland Services BV filed Critical Givaudan Nederland Services BV
Publication of EP2129758A2 publication Critical patent/EP2129758A2/de
Withdrawn legal-status Critical Current

Links

Classifications

    • 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

  • perfume compositions For the purposes of this invention a perfume composition is defined as a mixture of fragrance ingredients, if desired mixed with or dissolved in a suitable solvent or solvents and/or mixed with a solid substrate.
  • perfume and fragrance are used synonymously.
  • Perfume or fragrance ingredients are well known to those skilled in the art, and include those mentioned, for example, in S. Arctander, Perfume and Flavor Chemicals (Montclair, N.J., 1969), in S. Arctander, Perfume and Flavor Materials of Natural Origin (Elizabeth, N.J., 1960) and in "Flavor and Fragrance Materials - 1991", Allured Publishing Co. Wheaton, III. USA.
  • Perfume ingredients may include natural products such as extracts, essential oils, absolutes, resinoids, resins, concretes etc., and also synthetic basic substances such as hydrocarbons, alcohols, aldehydes, ketones, ethers, acids, esters, acetals, ketals, nitriles, etc., including saturated and unsaturated compounds, aliphatic, alicyclic and heterocyclic compounds.
  • the invention is particularly concerned with perfume compositions that have the ability to reduce or prevent residual malodours of laundry treated with the enzyme lipase.
  • the invention thus also relates to perfumed laundry detergents. More specifically it relates to perfumed laundry detergents containing a lipase.
  • the invention also relates to perfumes suitable for addition to laundry detergents containing lipase. In particular, it relates to fragrance ingredients, mixtures thereof, and perfume compositions for inhibiting the activity of lipases that may cause a post-wash malodour problem.
  • Lipases are of great benefit in laundry detergents since such detergents are more able to deal with greasy soils on cloth by hydrolysis of the fat therein.
  • laundry detergents may sometimes leave residual odours attached to the cloth.
  • This problem is not alleviated by the use of "odour-purified” lipases ("odour-purified” defined as per test method of EP 142 886, described for proteases).
  • odour-purified lipases odour-purified lipases
  • Such residual malodours detract from the overall performance of the detergent as perceived by the customer. It has been found that this malodour effect cannot be overcome simply by adding traditional perfumes to the detergent. Indeed, some perfumes are found to make the situation even worse.
  • perfumes containing at least a certain minimum quantity of fragrance ingredients chosen from certain groups are active in the inhibition of lipases and can thereby reduce the generation of malodours from degradation of fats and oils and so produce a marked counteraction of the malodour generated following washing of dairy- soiled cloths in lipase-containing washing products.
  • the present invention is based on extensive testing of fragrance ingredients and mixtures thereof in lipase inhibition tests, details of which are given below.
  • the ingredients were classified into different groups based on the ability to inhibit lipase, as represented by a lipase inhibition score, as follows:
  • fragrance ingredients falling into the different groups are given below. Based on this classification of fragrance ingredients, the invention enables perfume compositions to be formulated that can reduce or counteract residual malodours associated with lipases.
  • the invention provides a perfume composition comprising at least about 60% by weight of fragrance ingredients selected from Groups A and B, wherein:
  • Group A consists of:
  • fragrance ingredients constituting the perfume composition, thus excluding any solvents, diluents etc. such as diethyl phthalate, dipropylene glycol, benzyl benzoate, acetyl tributyl citrate, Hercolyn D, isopropyl myristate etc.
  • the perfume composition optionally contains up to about 40 by weight % of ingredients selected from Group C, wherein Group C consists of:
  • the perfume composition preferably contains less than about 40%, more preferably less than about 30% and most preferably less than about 10% by weight of fragrance ingredients selected from Class Z as listed below:
  • 3,7-dimethyloctan-3-ol (tetrahydrolinalol); ethyl vanillin; dodecanal; 1-methyl-1-(4- methylcyclohex-3-en-1-yl)ethyl acetate ⁇ terpinyl acetate); 3-methyl-5-phenylpentan-1-ol (e.g. PhenoxanolTM (IFF) or MefrosolTM (Q); geraniol; decen-9-ol; 2,4-dimethyl-4- phenyltetrahydrofuran (e.g. RhubafuranTM (Q)); 4,6-dimethyl-2-phenyl-3,6-dihydro-2H-pyran (e.g.
  • PhenoxanolTM IFF
  • MefrosolTM MefrosolTM
  • geraniol decen-9-ol
  • 2,4-dimethyl-4- phenyltetrahydrofuran e.g. Rhubafuran
  • PelargeneTM (Q)); tricyclo[5.2.1.0 ⁇ ⁇ 2,6 ⁇ ]dec-3-en-8-yl 2,2-dimethylpropanoate (e.g. PivacycleneTM (Q)); gamma-decalactone ; methyl 2- ⁇ [7-hydroxy-3,7- dimethyloctylidene]amino ⁇ benzoate (AurantionTM (Q)); 1 ,3-benzodioxole-5-carbaldehyde ⁇ heliotropin); eugenol; isoeugenol; 1-methyl-3-(2-methylpropyl)cyclohexanol (RossitolTM (Q)); triethyl citrate; decanal (aldehyde C10); citronellol; 3,7,11-trimethyldodeca-1 ,6,10-trien- 3-ol (nerolidol); l y-dioxacycloheptadecan-
  • Group Z 1 ,7,7-trimethylbicyclo[2.2.1]hept-2-yl acetate ⁇ isobornyl acetate); "l-(methyloxy)-4-[prop-1- enyl]benzene ⁇ anethole); 4-(4-hydroxy-4-methylpentyl)cyclohe ⁇ -3-ene-1 -carbaldehyde (LyralTM (IFF)); 1-(3,5,5,6,8,8-hexamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethanone (TonalidTM); benzyl benzoate; methyl salicylate; 1-(methyloxy)-4-prop-2-enylbenzene (methyl chavicol); 3-methyl-4-(1 ,2,2-trimethylpropyl)pent-4-en-2-one (acetyl di iso amylene); oxacyclohexadecan-2-one (cyclopentadecanolide or ExaltolideTM (F)); tri
  • the perfume composition may optionally include one or more additional ingredients selected from solvents, diluents, additives, excipients etc. Suitable materials and quantities are well known to those skilled in the art.
  • the perfume composition conveniently includes at least 65%, at least 70% or at least 75% by weight of ingredients in Groups A and B. Desirably at least 65% by weight of the weight in toto of the perfume composition (including any solvents, diluents etc) comprises fragrance ingredients selected from Groups A and B.
  • the perfume composition desirably includes at least 40%, preferably at least 50%, more preferably at least 60% by weight and possibly more of ingredients in Group A.
  • At least 70%, more preferably at least 85% by weight, of the total Group A and Group B ingredients comprise Group A ingredients.
  • the perfume composition comprises at least 3, 4, 5, 6, 7, 8 or more ingredients from Groups A and B.
  • the composition comprises at least 3, 4, 5, 6, 7, 8 or more ingredients from Group A.
  • the composition may additionally or alternatively comprise at least 3, 4, 5, 6, 7, 8 or more ingredients from Group B.
  • the use of a mixture of several fragrance ingredients assists formulation of perfume compositions having good or desired hedonic properties as well as lipase-associated malodour counteracting properties.
  • Group A and Group B ingredients for which the value of the octanol-water partition coefficient (as expressed in its logarithmic form as logi 0 P) is greater than about 3, where Log P is calculated from group contribution methods using ACD Labs Log P db V9.0, Advanced Chemistry Development Inc. Toronto, Canada.
  • Preferred Group A and B materials on this basis are listed in Table 1 below according to their trivial names, with ACD values of log P.
  • the average of the log P values of the Group A and B ingredients in the composition is greater than about 3.
  • fragrance ingredients and mixtures with a log P value in excess of 3 assists in deposition and retention of the perfume composition on cloth, thus enhancing lipase- associated malodour counteraction in normal use.
  • perfume compositions of the invention find application in laundry products, particularly laundry detergents containing lipase.
  • the invention thus provides a laundry product including a composition containing at least about 60% by weight of one or more fragrance ingredients selected from Groups A and B as specified above.
  • composition is preferably a perfume composition in accordance with the invention, with preferred features as specified above.
  • the laundry product is conveniently in the form of a laundry detergent containing lipase.
  • the perfume is suitably present in an amount in the range 0.05 to 1.5% by weight based on the weight of the laundry product.
  • Laundry detergents according to the invention may be in any convenient form including powdered or granular solids, bars, pastes or liquids, either aqueous or non-aqueous. Apart from lipase they may contain ingredients usual in the art e.g. anionic, cationic, zwitterionic or nonionic detergent active compounds, builders, sequestrants, inorganic fillers, bleaching agents, optical brighteners, antiredeposition agents, fabric conditioning agents, other enzymes and the like. Such laundry detergents may further contain other conventional ingredients such as described in the literature cited above.
  • a typical laundry detergent comprises: 5-40% anionic detergent active, 1-20% non-ionic detergent active, 0-5% lather booster, 0-30% builders/sequestrants, 0-60% inorganic fillers, 0-15% bleaching agent, up to 15% of one or more of optical brighteners, anti-redeposition agents, enzymes and fabric conditioning agents and 0.05-1.5% of perfume.
  • Suitable lipases for inclusion in laundry detergents according to the invention are e.g. Lipozyme, Lipolase, Lipex 100T, SP-285, SP-356 and SP-400 of Novo lndustri A/S, Denmark, Amano lipases P, B, CES, CE, AP, M-AP, and AML of Amano Pharmaceutical Co., Japan, Meito lipases MY-30, OF and PL, Saiken lipase and Enzeco lipase (trade names). Lipases may be added in admixture with other enzymes.
  • the quantity of lipase in the laundry detergent is preferably such as to produce a lipolytic enzyme activity of at least 20 LU/g, particularly 100 LU/g or more, most suitably at least 500 LU/g.
  • the laundry product may alternatively comprise a product such as a fabric conditioner, fabric conditioner ball, tumble drier sheet, fabric refresher spray and similar products that may reasonably be expected to come into contact with cloth or fabric, particularly cloth or fabric that has been or will be treated with a lipase-containing consumer product.
  • the laundry product may also be in the form of pre-wash treatment product, particularly when using compositions with a log P above 3, to enhance retention on cloth or fabric.
  • a further aspect of the invention relates to a method of preventing or reducing lipase- derived malodour on cloth or fabric laundered in lipase-containing laundry products, comprising contacting the cloth or fabric with a composition containing at least about 60% by weight of one or more fragrance ingredients selected from Groups A and B as specified above.
  • the composition is preferably a perfume composition in accordance with the invention, which is conveniently present in a laundry product in accordance with the invention.
  • the invention covers use of composition containing at least about 60% by weight of one or more fragrance ingredients selected from Groups A and B as specified above for the purpose of preventing or reducing lipase-derived malodour on cloth or fabric.
  • the composition is preferably a perfume composition in accordance with the invention, which is conveniently present in a laundry product in accordance with the invention.
  • the cloth or fabric is suitably contacted with the composition before, during or after washing with a lipase-containing laundry product, preferably during or after washing, with the composition desirably being present on the cloth or fabric during drying.
  • the perfume composition as hereinabove described my optionally be entrapped with an entrapment material such as polymers, capsules, microcapsules and nanocapsules, liposomes, film formers, absorbents such as carbon or zeolites, cyclic oligosaccharides and mixtures thereof, and/or they may be chemically bonded to substrates, which are adapted to release the fragrance molecule upon application of an external stimulus such as light, enzyme, or the like, and then mixed with laundry products, particular laundry detergents containing lipase.
  • an entrapment material such as polymers, capsules, microcapsules and nanocapsules, liposomes, film formers, absorbents such as carbon or zeolites, cyclic oligosaccharides and mixtures thereof, and/or they may be chemically bonded to substrates, which are adapted to release the fragrance molecule upon application of an external stimulus such as light, enzyme, or the like, and then mixed with laundry products, particular laundry detergents containing lipas
  • the invention thus provides a laundry product including an entrapped, preferably encapsulated, e.g. microencapsulated, composition containing at least about 60% by weight of one or more fragrance ingredients selected from Groups A and B as specified above.
  • Example 1 Lipase Inhibition Test
  • BIS-TRIS buffer pH 6.5 0.1 M BIS-TRIS buffer pH 6.5. Prepared by dissolving 10.46g BIS-TRIS buffer in distilled water to 100ml. Adjusted to pH 6.5 with concentrated HCI (measured using Corning 215 pH meter) and made up to 500ml with distilled water.
  • Lipex® 100T Enzyme Solution Prepared by dissolving 0.05g Lipex (Novozymes) in BIS-TRIS buffer to 2ml to give a 25mg/ml solution. This was diluted 1/100 in BIS-TRIS buffer to give a final concentration of 0.25mg/ml. Use Immediately.
  • TMUO 4-trifluoromethylumbelliferyl oleate
  • Each fragrance ingredient was tested at three different concentrations (2500, 1250 and 312 ppm).
  • Three ingredient stock solutions were made for each ingredient to be tested.
  • a 15,000ppm ingredient stock fragrance solution was made by dissolving 75mg of ingredient in 5g of BIS-TRIS buffer and vortexed. 2ml of this solution was mixed with 2ml of BIS-TRIS buffer and vortexed to create a 7,500ppm stock solution. Finally to create a 1 ,875ppm stock solution 1 ml of the 7,500ppm solution was added to 3ml of BIS-TRIS buffer and vortexed. This was repeated for all twenty-four ingredients to be screened per micro-titre plate.
  • tetrahydrolinalol inhibited lipase activity completely at both 2500ppm and 1250ppm, and aldehyde c12 by more than 90% at these concentrations.
  • Group A used in the invention Materials such as lononeTM and Nonanal at concentrations of 2500ppm inhibited lipase >15% and ⁇ 25% and are thus classified in Group B.
  • Materials such as phenylethyl phenylacetate inhibited lipase > 5% and ⁇ 15% at 2500ppm and are classified in Group C.
  • Materials with inhibition scores ⁇ 5% at 2500ppm, such as isobornyl acetate are classified in Group Z and are preferably to be avoided in preparing perfumes of the invention. Further examples of results are given in Table 3.
  • Perfume compositions were tested on their ability to counteract residual malodour on cloth washed in lipase containing laundry detergent.
  • a standard soiling method was used as described below: 10 g of dairy product (preferably milk) was applied evenly over squares of acrylic cloth of 1600 cm 2 . The cloths were then sealed in plastic bags for 1 hour. Thereafter, the cloths were line dried overnight.
  • dairy product preferably milk
  • Laundry detergent powder composition percent w/w
  • Perfume composition (as specified below) 0.1 Bleaching agents (Sodium perborate/EDTA) 6.8
  • the dried cloths were evaluated by an expert panel, to assess reductions in lipase-derived malodour.
  • perfume compositions 1 to 3 are in accordance with the invention and composition 4 is a comparative example outside the scope of the invention.
  • Perfume compositions 1-5 designed according to the invention when evaluated by an expert panel, were found to offer significant reductions in lipase-derived malodour over the comparative example taken from the prior art.

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)
  • Detergent Compositions (AREA)
  • Fats And Perfumes (AREA)
  • Cosmetics (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
EP08716029A 2007-02-26 2008-02-26 Parfüm-zusammensetzungen Withdrawn EP2129758A2 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB0703679A GB0703679D0 (en) 2007-02-26 2007-02-26 Perfume compositions
PCT/EP2008/001486 WO2008104352A2 (en) 2007-02-26 2008-02-26 Perfume compositions

Publications (1)

Publication Number Publication Date
EP2129758A2 true EP2129758A2 (de) 2009-12-09

Family

ID=37945719

Family Applications (1)

Application Number Title Priority Date Filing Date
EP08716029A Withdrawn EP2129758A2 (de) 2007-02-26 2008-02-26 Parfüm-zusammensetzungen

Country Status (5)

Country Link
EP (1) EP2129758A2 (de)
JP (1) JP2010519368A (de)
BR (1) BRPI0808420A2 (de)
GB (1) GB0703679D0 (de)
WO (1) WO2008104352A2 (de)

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US8754028B2 (en) * 2008-12-16 2014-06-17 The Procter & Gamble Company Perfume systems
EP2204155A1 (de) 2008-12-30 2010-07-07 Takasago International Corporation Duftstoffzusammensetzung für Kernhüllenmikrokapseln
CN107028801A (zh) 2009-12-18 2017-08-11 宝洁公司 香料和香料包封物
US9186642B2 (en) 2010-04-28 2015-11-17 The Procter & Gamble Company Delivery particle
US20110269657A1 (en) * 2010-04-28 2011-11-03 Jiten Odhavji Dihora Delivery particles
US9993793B2 (en) 2010-04-28 2018-06-12 The Procter & Gamble Company Delivery particles
GB201021050D0 (en) 2010-12-13 2011-01-26 Givaudan Sa Moc compositions
CA2869877A1 (en) * 2012-04-10 2013-10-17 The Procter & Gamble Company Malodor reduction compositions
JP2013249293A (ja) * 2012-06-04 2013-12-12 Kao Corp リパーゼ活性阻害剤、抗真菌剤、及びフケ抑制剤
JP5925605B2 (ja) * 2012-06-04 2016-05-25 花王株式会社 リパーゼ活性阻害剤、抗真菌剤、及びフケ抑制剤
CN105579075A (zh) * 2013-08-01 2016-05-11 宝洁公司 包含恶臭减少组合物的制品
EP2865739B1 (de) 2013-10-28 2018-09-19 Symrise AG Verwendung von Lactonen
MY193669A (en) * 2016-05-11 2022-10-24 Lion Corp Perfume composition for clothing detergents and detergent composition for clothing
FR3052665B1 (fr) 2016-06-16 2018-06-08 Expressions Parfumees Melange comprenant au moins de la dihydro-5-pentyl-2(3h)-furanone et du 2,4-dimethyl-4-phenyltetrahydrofurane et son utilisation pour masquer les mauvaises odeurs
WO2019078385A1 (ko) * 2017-10-20 2019-04-25 주식회사 엘지생활건강 이취 억제용 향료 조성물
US12486478B2 (en) 2020-10-16 2025-12-02 The Procter & Gamble Company Consumer products comprising delivery particles with high core:wall ratios
MX2023004231A (es) 2020-10-16 2023-04-21 Procter & Gamble Composiciones de producto de consumo que comprenden una poblacion de encapsulados.
JP2023543578A (ja) 2020-10-16 2023-10-17 ザ プロクター アンド ギャンブル カンパニー 少なくとも２つの封入体集団を有する消費者製品組成物
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Also Published As

Publication number Publication date
BRPI0808420A2 (pt) 2014-07-22
WO2008104352A3 (en) 2009-01-15
WO2008104352A2 (en) 2008-09-04
JP2010519368A (ja) 2010-06-03
GB0703679D0 (en) 2007-04-04

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