+

US20090257974A1 - Perfume Compositions - Google Patents

Perfume Compositions Download PDF

Info

Publication number
US20090257974A1
US20090257974A1 US12/375,756 US37575607A US2009257974A1 US 20090257974 A1 US20090257974 A1 US 20090257974A1 US 37575607 A US37575607 A US 37575607A US 2009257974 A1 US2009257974 A1 US 2009257974A1
Authority
US
United States
Prior art keywords
perfume
methyl
group
ingredients
methyloxy
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.)
Abandoned
Application number
US12/375,756
Inventor
Gordon Michael Evans
Alan Forbes Provan
David Jonathan Bradshaw
John Martin Behan
Keith Douglas Perring
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
Assigned to GIVAUDAN NEDERLAND SERVICES B.V. reassignment GIVAUDAN NEDERLAND SERVICES B.V. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: BRADSHAW, DAVID JONATHAN, EVANS, GORDON MICHAEL, PERRING, KEITH DOUGLAS, PROVAN, ALAN FORBES, BEHAN, JOHN MARTIN
Publication of US20090257974A1 publication Critical patent/US20090257974A1/en
Abandoned legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01K—ANIMAL HUSBANDRY; AVICULTURE; APICULTURE; PISCICULTURE; FISHING; REARING OR BREEDING ANIMALS, NOT OTHERWISE PROVIDED FOR; NEW BREEDS OF ANIMALS
    • A01K1/00—Housing animals; Equipment therefor
    • A01K1/015—Floor coverings, e.g. bedding-down sheets ; Stable floors
    • A01K1/0152—Litter
    • 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
    • A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
    • A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
    • A61L15/20—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons containing organic materials
    • 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
    • A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
    • A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
    • A61L15/42—Use of materials characterised by their function or physical properties
    • A61L15/46—Deodorants or malodour counteractants, e.g. to inhibit the formation of ammonia or bacteria
    • 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
    • C11B9/0015—Aliphatic compounds containing oxygen 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
    • C11B9/0007—Aliphatic compounds
    • C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
    • C11B9/0019—Aliphatic compounds containing oxygen as the only heteroatom carbocylic acids; Salts or esters thereof
    • 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
    • C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
    • C11B9/003—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing less than six carbon atoms
    • 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
    • C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
    • C11B9/0034—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing six carbon atoms
    • 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
    • C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
    • C11B9/0038—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing more than six carbon atoms
    • 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
    • C11B9/0069—Heterocyclic compounds
    • C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
    • C11B9/0076—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing less than six atoms
    • 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
    • C11B9/0084—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing more than six atoms
    • 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
    • C11B9/0088—Spiro compounds
    • 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
    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/20—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials
    • A61L2300/216—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials with other specific functional groups, e.g. aldehydes, ketones, phenols, quaternary phosphonium groups

Definitions

  • This invention relates to perfume compositions, to consumer products containing such perfume compositions, and to the use of such perfume compositions to provide deodourant effects including in particular inhibiting and ameliorating the odour of urine.
  • the invention is particularly concerned with perfume compositions that inhibit the bacterial generation of ammonia from urea.
  • Urine is a clear, transparent fluid that normally has an amber color, and when fresh is generally of low odour.
  • the average amount of urine excreted by a human in 24 hours is about 1,200 cubic centimeters.
  • Chemically, urine is mainly an aqueous solution of sodium chloride and organic substances such as urea and uric acid. Normally, it contains about 960 parts of water to 40 parts of solid matter. Many hundreds of different mineral salts and organic compounds are present in urine, albeit at trace levels for a significant proportion of these.
  • the pH of normal urine is between 4.5 and 7.8, but usually it ranges between 5.0 and 6.0, due to obligatory excretion of acid produced every day.
  • the major components of urine malodour are: ammonia, volatile fatty acids (primarily acetic, propionic, butyric, formic); volatile sulphur compounds e.g hydrogen sulfide (H 2 S) and methyl sulphides such as methyl mercaptan (CH 3 SH); other nitrogenous compounds such as indole, skatole, pyridine, pyrrole, ethylamine; various other volatiles including benzyl alcohol, phenol, p-cresol, ethanol, methanol, acetone, methyl ethyl ketone, acetaldehyde, propionaldehyde, pentanone, heptanone, propanol, butanol, octanol.
  • volatile fatty acids primarily acetic, propionic, butyric, formic
  • volatile sulphur compounds e.g hydrogen sulfide (H 2 S) and methyl sulphides such as methyl mer
  • odourous molecules are mainly produced as a result of the bacterial degradation of exogenous materials such as urea and uric acid found in urine, though trace levels of certain materials may reflect materials found in the diet or in the environment.
  • the nitrogenous bases in particular amnmonia, contribute significantly to the malodour recognised by most people from used diapers or other hygiene products such as adult incontinence products.
  • This malodour arises at least partly from the bacterially mediated degradation of urea, from the metabolism of microorganisms present on the skin or from the urogenital tract, for example from the growth of Proteus and Micrococcus species. All strains of Proteus spp. form the enzyme urease during their metabolism.
  • Urease has the ability to rapidly break down urea (constituting about 2% of human urine) into ammonia causing unpleasant odour.
  • the headspace composition above stale urine comprises a variety of materials, but the dominant malodour contributor under most conditions is invariably ammonia. Techniques that lead to reduction in the amount of ammonia present above urine are therefore of possible utility in product sectors associated with sanitation, hygiene, and incontinence. Several approaches are known in the art that address this need.
  • Antimicrobial agents used in personal products are designed to reduce the population, inhibit the growth or diminish the metabolic activities of microorganisms associated closely with the body—on the surface of the skin, in mucosal surfaces, in the urogenital tract, etc.
  • Typical agents of this nature include triclosan (2′,4,4′-trichloro-2-hydroxydiphenyl ether) and zinc oxide which are well known to exert antimicrobial and deodourant effects.
  • triclosan (2′,4,4′-trichloro-2-hydroxydiphenyl ether) and zinc oxide which are well known to exert antimicrobial and deodourant effects.
  • the use of common deodourant actives results in a non-selective antimicrobial action exerted upon most of the skin's natural microflora.
  • PCT publication WO 2002/47472 relates to products and methods that utilise a urease inhibitor formed from a polyanionic, and preferably amine-based, chelating agent and a divalent heavy metal ion, to prevent or minimize ammonia odour produced by the degradation of urea in secreted or excreted body fluids.
  • WO 97/46187 relates to absorbent articles in particular sanitary napkins and panty liners having an odour control system comprising a polyfunctionally substituted aromatic chelating agent for improved odour control.
  • WO 2001/80915 relates to absorbent articles that comprise a cationic polysaccharide, preferably chitosan material, and silicate. These articles claim to deliver improved odour control performance (synergistic odour reduction) and improved fluid handling properties/absorption performance.
  • WO 94/25077 relates to odour control through an absorbent article containing a boric acid/sodium tetraborate buffer.
  • EP 509409 relates to malodour control though the design of an absorbent article containing a deodourizing blend of anhydrous, non-buffer blend of at least basic and pH neutral odour absorbing particles.
  • Pat. No. 6,031,147 discloses an absorbent product comprising a hydrogel-forming polymeric absorbent material and a surface-active agent such as ethoxylated sorbitan monooleate, having a hydrophilic/lipophilic balance of less than about 12.
  • WO 99/06078 describes absorbent materials containing cyclodextrin as an odour control material.
  • WO 98/26808 describes odour control provided by a combination of a material that inhibits the formation of odour (and has at least one attribute selected from the group consisting of antimicrobial activity, urease inhibition activity, pH adjustment activity) and an odour-absorbing material for objectionable odour molecules selected from the group consisting of cyclodextrin, zeolite, activated carbon, kieselguhr, acid salt forming materials and mixtures thereof.
  • the scent signal is provided by cyclodextrin/perfume inclusion complexes and/or matrix perfume microcapsules to assure the wearer that the product is working.
  • WO 2000/51652 describes the use of oxidising agents such as a peroxyacid in combination with an odour-absorbing agent such as silica and/or zeolite.
  • WO2003/051413 and WO 2003/051410 relate to a fibrous absorbent material or cellulose fibers treated with a carboxylic acid based odour control agent.
  • WO 98/25562 describes a diaper design that contains perfume zones and microcapsules as release agents to provide odour control.
  • Published application US 2003/072733 describes a process for absorbing moisture and/or malodour while providing a fragrance to the surrounding ambience.
  • WO 2005/044320 relates to a dual purpose volatile substance controlling composition comprising a sorbent and a fragrance component designed to control malodours including those resulting from bodily fluids. The design involves volatile substance sorption directly linked to fragrance release.
  • Perfumes may simply mask malodours.
  • WO 2004/10325 describes sanitary absorbent articles comprising a non-aqueous volatile cooling agent such as menthyl lactate or perfume.
  • WO 2004/108177 describes the incorporation of a starch-encapsulated accord into products that releases perfume to minimise odour.
  • perfume compositions have been disclosed which exhibit effective deodourant action for specific malodours.
  • WO 2000/01356 describes certain perfume components and compositions thereof, useful in reducing or preventing body malodour.
  • the perfume components are described as inhibiting coryneform bacteria that are capable of catabolising fatty acids and are responsible for the production of short chain fatty acid malodour.
  • the perfume components (or compositions thereof) in-use produce a deodourant effect.
  • many of the deodourant perfumes disclosed in the art have relatively high odour intensities that are unsuitable for use in the sanitary or incontinence product sector, and/or are not effective in counteracting or inhibiting ammonia malodour.
  • perfume compositions are capable of inhibiting the development of ammonia from urea at sub-minimum inhibitory growth concentrations (MIC), and are effective in counteracting urine malodour in spite of exhibiting relatively low perfume odour intensities.
  • MIC sub-minimum inhibitory growth concentrations
  • this invention provides a perfume composition that inhibits the formation of urine malodour, and is effective in ameliorating the perception of urine malodour if present.
  • a perfume composition comprises between 10% and 30% in total by weight of perfume ingredients selected from two groups:
  • Group A consisting of (3Z)-hex-3-enyl acetate; 3-(1,3-benzodioxol-5-yl)-2-methylpropanal; (3Z)-hex-3-en-1-ol; 1-[4-(methyloxy)phenyl]ethanone; 3-methyl-5-phenylpentan-1-ol; 5-heptyldihydrofuran-2(3H)-one; phenylmethyl acetate; 2-(4-methylcyclohex-3-en-1-yl)propan-2-ol; (3E)-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one; (3E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one; 4-hydroxy-3-(methyloxy)benzaldehyde; 1-methyl-3-(2-methylpropyl)cyclohexanol; 7,9-dimethylspiro[5.5]unde
  • the invention in another aspect, relates to a method of preventing or ameliorating urine malodour comprising bringing into contact with urine or urine residues an effective amount of a perfume composition according to the invention.
  • At least 0.3 wt % of a perfume ingredient must be present before it may be considered to contribute significantly towards the efficacy of the compositions, i.e. perfume ingredients present at concentrations below 0.3 wt % and ignored in the calculation of the number of Group A and Group B ingredients in the composition.
  • Preferred perfume compositions comprise at least three Group A ingredients, more preferably at least four ingredients and most preferably at least six ingredients.
  • a perfume composition is defined as a mixture of perfume ingredients, if desired mixed with or dissolved in a suitable solvent or solvents and/or mixed with a solid substrate.
  • Perfume 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, Ill. USA.
  • Perfume ingredients may include natural products such as extracts, essential oils, absolutes, resinoids, resins, concretes etc., and also synthetic substances such as hydrocarbons, alcohols, aldehydes, ketones, ethers, acids, esters, acetals, ketals, nitriles, etc., including saturated and unsaturated compounds, aliphatic, macrocyclic and heterocyclic compounds.
  • references herein to the percentage by weight of perfume ingredients means relative to the total weight of perfume ingredients in the perfume composition and includes materials that are used within perfumery as vehicles or solvents for other perfume ingredients, for example dipropylene glycol, isopropyl myristate, benzyl benzoate, diethyl phthalate, triacetin and triethyl citrate.
  • Perfumes constructed according to the above design provide effective urease inhibition without being overtly strongly antimicrobial (as indicated by tests described below) and also are able to counteract urine malodour olfactorily.
  • the invention provides a perfumed consumer product comprising a perfume composition in accordance with the invention.
  • a consumer product means comprises a solid, liquid or soft solid formulation especially for use in or on a substrate such as skin, hair (including fur), clothing or hard surface.
  • Examples of such consumer products include bathroom and kitchen cleaners, carpet cleaners, polishes, personal body refreshers and deodourants, pet deodourants, in a variety of formats such as liquids (particularly as delivered by trigger sprays or aerosols), gels and powders, all of which are well known in the art.
  • Another example of a consumer product relevant to the present invention is pet litter.
  • the invention also covers use of a perfume composition according to the invention for the purpose of inhibiting urea breakdown to form ammonia. Preferred features of this aspect are as discussed below in connection with the perfume composition of the invention.
  • a concomitant effect of the inhibition of ammonia production is that pH remains relatively constant, or at least the rate of increase of pH is much lower than in the absence of the perfume composition. Such pH control may be of indirect benefit in areas other than malodour management.
  • the invention provides an article suitable for preventing or ameliorating urine malodour, comprising an effective amount of a perfume composition according to the invention.
  • articles of manufacture include diapers, incontinence pads, hygienic body wipes, and catamenials including sanitary pads and sanitary towels.
  • Perfume compositions of the invention may be incorporated into or onto such articles by any suitable means known in the art, for example by bringing them into contact with adsorbents present in such articles, although they be used in association with a wide variety of elements of such articles. It may sometimes be advantageous to encapsulate the perfumes of the invention prior to incorporation into such articles.
  • Perfumes formulated to the guidelines described herein will maintain the pH of a urea-supplemented microbial suspension (as described below in Example 1) at a pH that is at least 1.2 pH units lower than that of a non-perfumed control. It is believed that this difference in pH is directly correlated to a decrease in ammonia production. It is highly desirable that the effect is achieved at sub-inhibitory growth levels. Two groups of perfume ingredients have been identified. Group A materials have the highest efficacy, but Group B may be used in place of a fraction of the Group A materials where this is desirable in order to achieve the right balance of hedonic properties, anti-microbial action and sensory-derived malodour counteraction.
  • Group A ingredients are listed below, where names in parentheses represents equivalent names—either trivial names commonly used within the fragrance and flavour industry, or tradenames that are sources for the material cited.
  • Particularly preferred Group A materials are:
  • the minimum inhibitory concentration of perfumes may be determined by the following method.
  • Proteus vulgaris NCTC 4175 National Collection of Type Cultures, Public Health Laboratory Service, Central Public Health Laboratory, 61 Colindale Avenue, London
  • Test ingredients were diluted in sterile TSB.
  • A-H a standard, 96-well plastic microtitre plate
  • Row H contained only TSB for use as a bacterial control to indicate the degree of turbidity resulting from bacterial growth in the absence of any test material.
  • 200 ⁇ l of the initial dilution of ingredient was transferred to the 1st and 7th well of the appropriate row. All other test wells were filled with 100 ⁇ l of sterile TSB using an 8-channel micropipette.
  • a blank plate was prepared for each set of eight samples in exactly the same way, except that 100 ⁇ l of sterile 0.1% special peptone was added instead of bacterial culture. Test and control plates were sealed using autoclave tape and incubated for 18 hours at 37° C.
  • the microtitre plate reader (Thermo Multiskan Ascent) was preset to gently agitate the plates, to mix the contents. The absorbance at 540 nm was used as a measure of turbidity resulting from bacterial growth. Both control (un-inoculated plate) and inoculated plates were read for each set of samples. The absorbance readings from the control plate were subtracted from the relevant inoculated plate readings thus removing turbidity due to perfume and possible colour changes during incubation. Thus the corrected readings generated were absorbances resulting from turbidity from bacterial growth. The MIC was taken as the concentration of ingredient required to inhibit growth so that the average change in absorbance during the incubation period was ⁇ 0.3.
  • SSR Medium 380 ml distilled water, 364 mg KH 2 PO 4 , 380 mg Na 2 HPO 4 , 8 g Urea, 40 mg Yeast extract, 20 ml 0.02% phenol red indicator, pH 6.8, solution filter sterilised.
  • Culture Liquid culture of P. vulgaris NCTC4175 was prepared by adding loops of fresh culture from solid media (Tryptone Soya Agar) to sterile 0.1% special peptone solution. Absorbance of culture was adjusted to be OD610 nm>2.3
  • Fragrances were aseptically prepared at 2500 ppm in medium in duplicate (5 ml volumes) using solubiliser Synperonic 91/10 at ratio of 1:2 fragrance: solubiliser.
  • 5 ml volumes of positive and negative controls were prepared. Positive controls and all test solutions were inoculated by adding 200 ⁇ l of prepared culture, mixed and incubated for 24 hours @ 37oC. No culture was added to the negative growth controls. Initially solutions were orange in colour. Urease activity can be noted by the production of a purple/red colour, indicating high pH resulting from ammonia production. The degree of urease activity/ammonia production was assessed by pH electrode.
  • Fragrance formulations 3.2, 3.4, and 3.8 detailed in Table 1 were created following the creative guidelines of the present invention.
  • Formulations, 3.1, 3.3, 3.5, 3.6 and 3.7 are comparatives that fall outside these guidelines. All examples bar numbers 3.5 and 3.6 meet the Urease Inhibition Assay target of a difference of 1.2 pH units compared to the positive control. However only Formulations 3.2, 3.4 and 3.8 achieve this effect at sub-MIC level.
  • These three perfumes were also evaluated in a urine malodour test as described in example 3 of PCT/GB2007/001172 using malodour model A of example 1 therein. All three were found to be effective in reducing the perception of the urine malodour.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Environmental Sciences (AREA)
  • Materials Engineering (AREA)
  • Hematology (AREA)
  • Biodiversity & Conservation Biology (AREA)
  • Zoology (AREA)
  • Animal Husbandry (AREA)
  • Fats And Perfumes (AREA)
  • Cosmetics (AREA)
  • Disinfection, Sterilisation Or Deodorisation Of Air (AREA)

Abstract

Perfume compositions comprise between 10% and 30% in total by weight of perfume ingredients selected from two groups, Group A, Group B, with the provisos that over 5% but less than 15% of the perfume composition must comprise Group A ingredients, and for compositions comprising less than 10% of Group A ingredients the agregate percentage of Group B ingredients present must be at least equal to the expression 2*/10-A%) where A% is the total percentage of Group A ingredients in the composition.

Description

    FIELD OF THE INVENTION
  • This invention relates to perfume compositions, to consumer products containing such perfume compositions, and to the use of such perfume compositions to provide deodourant effects including in particular inhibiting and ameliorating the odour of urine. The invention is particularly concerned with perfume compositions that inhibit the bacterial generation of ammonia from urea.
    • BACKGROUND TO THE INVENTION
  • The unpleasantness of urine malodour is an age-old problem. When urine is excreted into absorbent articles such as clothing, diapers or incontinence pads, or onto floors surrounding urinals or WC bowls, an ammoniacal malodour may often be detected within a short time. The same problem occurs in pet litter, and may of course be relevant anywhere in the house for households including cats or dogs, etc.
  • Urine is a clear, transparent fluid that normally has an amber color, and when fresh is generally of low odour. The average amount of urine excreted by a human in 24 hours is about 1,200 cubic centimeters. Chemically, urine is mainly an aqueous solution of sodium chloride and organic substances such as urea and uric acid. Normally, it contains about 960 parts of water to 40 parts of solid matter. Many hundreds of different mineral salts and organic compounds are present in urine, albeit at trace levels for a significant proportion of these. The pH of normal urine is between 4.5 and 7.8, but usually it ranges between 5.0 and 6.0, due to obligatory excretion of acid produced every day.
  • The major components of urine malodour are: ammonia, volatile fatty acids (primarily acetic, propionic, butyric, formic); volatile sulphur compounds e.g hydrogen sulfide (H2S) and methyl sulphides such as methyl mercaptan (CH3SH); other nitrogenous compounds such as indole, skatole, pyridine, pyrrole, ethylamine; various other volatiles including benzyl alcohol, phenol, p-cresol, ethanol, methanol, acetone, methyl ethyl ketone, acetaldehyde, propionaldehyde, pentanone, heptanone, propanol, butanol, octanol. These odourous molecules are mainly produced as a result of the bacterial degradation of exogenous materials such as urea and uric acid found in urine, though trace levels of certain materials may reflect materials found in the diet or in the environment. The nitrogenous bases, in particular amnmonia, contribute significantly to the malodour recognised by most people from used diapers or other hygiene products such as adult incontinence products. This malodour arises at least partly from the bacterially mediated degradation of urea, from the metabolism of microorganisms present on the skin or from the urogenital tract, for example from the growth of Proteus and Micrococcus species. All strains of Proteus spp. form the enzyme urease during their metabolism. Urease has the ability to rapidly break down urea (constituting about 2% of human urine) into ammonia causing unpleasant odour. The headspace composition above stale urine comprises a variety of materials, but the dominant malodour contributor under most conditions is invariably ammonia. Techniques that lead to reduction in the amount of ammonia present above urine are therefore of possible utility in product sectors associated with sanitation, hygiene, and incontinence. Several approaches are known in the art that address this need.
  • Antimicrobial agents used in personal products are designed to reduce the population, inhibit the growth or diminish the metabolic activities of microorganisms associated closely with the body—on the surface of the skin, in mucosal surfaces, in the urogenital tract, etc. Typical agents of this nature include triclosan (2′,4,4′-trichloro-2-hydroxydiphenyl ether) and zinc oxide which are well known to exert antimicrobial and deodourant effects. The use of common deodourant actives results in a non-selective antimicrobial action exerted upon most of the skin's natural microflora. This can represent an undesirable feature of such deodourant formulations, since the natural microflora provides a protective barrier (colonisation resistance) against invasion by potentially pathogenic bacteria. Certain perfume components and mixtures thereof may contribute to such antimicrobial effects. For example, published US application US2004266302 relates to a disposable absorbent article containing an encapsulated antimicrobial essential oil for odour control.
  • PCT publication WO 2002/47472 relates to products and methods that utilise a urease inhibitor formed from a polyanionic, and preferably amine-based, chelating agent and a divalent heavy metal ion, to prevent or minimize ammonia odour produced by the degradation of urea in secreted or excreted body fluids. Similarly WO 97/46187 relates to absorbent articles in particular sanitary napkins and panty liners having an odour control system comprising a polyfunctionally substituted aromatic chelating agent for improved odour control.
  • Much of the art is concerned with the use of odour absorbent materials. For example, WO 2001/80915 relates to absorbent articles that comprise a cationic polysaccharide, preferably chitosan material, and silicate. These articles claim to deliver improved odour control performance (synergistic odour reduction) and improved fluid handling properties/absorption performance. WO 94/25077 relates to odour control through an absorbent article containing a boric acid/sodium tetraborate buffer. EP 509409 relates to malodour control though the design of an absorbent article containing a deodourizing blend of anhydrous, non-buffer blend of at least basic and pH neutral odour absorbing particles. U.S. Pat. No. 6,031,147 discloses an absorbent product comprising a hydrogel-forming polymeric absorbent material and a surface-active agent such as ethoxylated sorbitan monooleate, having a hydrophilic/lipophilic balance of less than about 12.
  • WO 99/06078 describes absorbent materials containing cyclodextrin as an odour control material. WO 98/26808 describes odour control provided by a combination of a material that inhibits the formation of odour (and has at least one attribute selected from the group consisting of antimicrobial activity, urease inhibition activity, pH adjustment activity) and an odour-absorbing material for objectionable odour molecules selected from the group consisting of cyclodextrin, zeolite, activated carbon, kieselguhr, acid salt forming materials and mixtures thereof. The scent signal is provided by cyclodextrin/perfume inclusion complexes and/or matrix perfume microcapsules to assure the wearer that the product is working.
  • WO 2000/51652 describes the use of oxidising agents such as a peroxyacid in combination with an odour-absorbing agent such as silica and/or zeolite. WO2003/051413 and WO 2003/051410 relate to a fibrous absorbent material or cellulose fibers treated with a carboxylic acid based odour control agent.
  • Perfumes have long been recognised as beneficial in hygiene and sanitary sectors. WO 98/25562 describes a diaper design that contains perfume zones and microcapsules as release agents to provide odour control. Published application US 2003/072733 describes a process for absorbing moisture and/or malodour while providing a fragrance to the surrounding ambience. WO 2005/044320 relates to a dual purpose volatile substance controlling composition comprising a sorbent and a fragrance component designed to control malodours including those resulting from bodily fluids. The design involves volatile substance sorption directly linked to fragrance release.
  • Perfumes may simply mask malodours. WO 2004/10325 describes sanitary absorbent articles comprising a non-aqueous volatile cooling agent such as menthyl lactate or perfume. WO 2004/108177 describes the incorporation of a starch-encapsulated accord into products that releases perfume to minimise odour. However, perfume compositions have been disclosed which exhibit effective deodourant action for specific malodours. For example, WO 2000/01356 describes certain perfume components and compositions thereof, useful in reducing or preventing body malodour. The perfume components (or compositions comprising the perfume components) are described as inhibiting coryneform bacteria that are capable of catabolising fatty acids and are responsible for the production of short chain fatty acid malodour. In this way, the perfume components (or compositions thereof) in-use produce a deodourant effect. However, many of the deodourant perfumes disclosed in the art have relatively high odour intensities that are unsuitable for use in the sanitary or incontinence product sector, and/or are not effective in counteracting or inhibiting ammonia malodour.
  • In spite of the above mentioned disclosures there still exists a need for cost-effective products that combat urine-derived malodour more efficiently, both from the perspective of malodour prevention as well as malodour amelioration, and do not suffer from the potential disadvantages of exploiting highly antimicrobial actives, whilst benefiting from the presence of perfumes that enjoy broad consumer acceptability.
  • It has now been surprisingly found that particular perfume compositions are capable of inhibiting the development of ammonia from urea at sub-minimum inhibitory growth concentrations (MIC), and are effective in counteracting urine malodour in spite of exhibiting relatively low perfume odour intensities.
    • SUMMARY OF THE INVENTION
  • In one aspect, this invention provides a perfume composition that inhibits the formation of urine malodour, and is effective in ameliorating the perception of urine malodour if present. Such a perfume composition comprises between 10% and 30% in total by weight of perfume ingredients selected from two groups:
  • Group A, consisting of (3Z)-hex-3-enyl acetate; 3-(1,3-benzodioxol-5-yl)-2-methylpropanal; (3Z)-hex-3-en-1-ol; 1-[4-(methyloxy)phenyl]ethanone; 3-methyl-5-phenylpentan-1-ol; 5-heptyldihydrofuran-2(3H)-one; phenylmethyl acetate; 2-(4-methylcyclohex-3-en-1-yl)propan-2-ol; (3E)-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one; (3E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one; 4-hydroxy-3-(methyloxy)benzaldehyde; 1-methyl-3-(2-methylpropyl)cyclohexanol; 7,9-dimethylspiro[5.5]undecan-3-one; perfume 1 being Lavandin AB8381™; methyl 2,4-dihydroxy-3,6-dimethylbenzoate; 3,7-dimethyloctan-1-ol; 2-(methyloxy)-4-propylphenol; perfume 2 being Rosenta AB8428™; 1-{[(1R,2S)-2-(1,1-dimethylethyl)cyclohexyl]oxy}butan-2-ol; perfume 3 being Headspace Freesia AB7254A™; 5-hexyldihydrofuran-2(3H)-one; prop-2-enyl [(2-methylbutyl)oxy]acetate; 1,3-benzodioxole-5-carbaldehyde; [4-(1-methylethyl)cyclohexyl]methanol; 2-hexylcyclopent-2-en-1-one; methyl (2E)-3-phenylprop-2-enoate; 2,6-dimethyloct-7-en-2-ol; 2-methyl-3-[4-(1-methylethyl)phenyl]propanal; and
    Group B consisting of 2-phenylethanol; 3,7-dimethyloctan-3-ol (tetrahydro linalol), 2-(methyloxy)-4-[(1E)-prop-1-enyl]phenyl acetate; 4-(methyloxy); (2E)-1-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-en-1-one; perfume 4 being Bergamot AB8392™, (3E)-3-methyl-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one; cyclopentadecanone; cyclohexadecanolide; prop-2-enyl 3-cyclohexylpropanoate; 3-[3-(1-methylethyl)phenyl]butanal; (3Z)-hex-3-enyl methyl carbonate; (1-methyl-2-{[(1S,3R,5R)-1,2,2-trimethylbicyclo[3.1.0]hex-3-yl]methyl}cyclopropyl)methanol; [3,3-bis(methyloxy)propyl]benzene; perfume 5 being Coumarex I Mod™;
    tricyclo[5.2.1.0{2,6}]dec-4-en-8-yl propanoate;
    with the provisos that over 5% but less than 15% of the perfume composition must comprise Group A ingredients, and for compositions comprising less than 10% of Group A ingredients the percentage of Group B ingredients present must be at least equal to the expression 2*(10-A%) where A% is the total percentage of Group A ingredients in the composition.
  • In another aspect, the invention relates to a method of preventing or ameliorating urine malodour comprising bringing into contact with urine or urine residues an effective amount of a perfume composition according to the invention.
  • At least 0.3 wt % of a perfume ingredient must be present before it may be considered to contribute significantly towards the efficacy of the compositions, i.e. perfume ingredients present at concentrations below 0.3 wt % and ignored in the calculation of the number of Group A and Group B ingredients in the composition.
  • Preferred perfume compositions comprise at least three Group A ingredients, more preferably at least four ingredients and most preferably at least six ingredients.
  • For the purposes of this invention a perfume composition is defined as a mixture of perfume ingredients, if desired mixed with or dissolved in a suitable solvent or solvents and/or mixed with a solid substrate. Perfume 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, Ill. USA. Perfume ingredients may include natural products such as extracts, essential oils, absolutes, resinoids, resins, concretes etc., and also synthetic substances such as hydrocarbons, alcohols, aldehydes, ketones, ethers, acids, esters, acetals, ketals, nitriles, etc., including saturated and unsaturated compounds, aliphatic, macrocyclic and heterocyclic compounds.
  • References herein to the percentage by weight of perfume ingredients means relative to the total weight of perfume ingredients in the perfume composition and includes materials that are used within perfumery as vehicles or solvents for other perfume ingredients, for example dipropylene glycol, isopropyl myristate, benzyl benzoate, diethyl phthalate, triacetin and triethyl citrate.
  • Perfumes constructed according to the above design provide effective urease inhibition without being overtly strongly antimicrobial (as indicated by tests described below) and also are able to counteract urine malodour olfactorily.
  • In a further aspect, the invention provides a perfumed consumer product comprising a perfume composition in accordance with the invention. For the purposes of this invention a consumer product means comprises a solid, liquid or soft solid formulation especially for use in or on a substrate such as skin, hair (including fur), clothing or hard surface. Examples of such consumer products include bathroom and kitchen cleaners, carpet cleaners, polishes, personal body refreshers and deodourants, pet deodourants, in a variety of formats such as liquids (particularly as delivered by trigger sprays or aerosols), gels and powders, all of which are well known in the art. Another example of a consumer product relevant to the present invention is pet litter.
  • In such consumer products as little as 0.1% by weight of the perfume composition in the product will suffice.
  • The invention also covers use of a perfume composition according to the invention for the purpose of inhibiting urea breakdown to form ammonia. Preferred features of this aspect are as discussed below in connection with the perfume composition of the invention. A concomitant effect of the inhibition of ammonia production is that pH remains relatively constant, or at least the rate of increase of pH is much lower than in the absence of the perfume composition. Such pH control may be of indirect benefit in areas other than malodour management.
  • In a further aspect, the invention provides an article suitable for preventing or ameliorating urine malodour, comprising an effective amount of a perfume composition according to the invention. Such articles of manufacture include diapers, incontinence pads, hygienic body wipes, and catamenials including sanitary pads and sanitary towels. Perfume compositions of the invention may be incorporated into or onto such articles by any suitable means known in the art, for example by bringing them into contact with adsorbents present in such articles, although they be used in association with a wide variety of elements of such articles. It may sometimes be advantageous to encapsulate the perfumes of the invention prior to incorporation into such articles.
    • Perfume Ingredients of the Invention
  • Perfumes formulated to the guidelines described herein will maintain the pH of a urea-supplemented microbial suspension (as described below in Example 1) at a pH that is at least 1.2 pH units lower than that of a non-perfumed control. It is believed that this difference in pH is directly correlated to a decrease in ammonia production. It is highly desirable that the effect is achieved at sub-inhibitory growth levels. Two groups of perfume ingredients have been identified. Group A materials have the highest efficacy, but Group B may be used in place of a fraction of the Group A materials where this is desirable in order to achieve the right balance of hedonic properties, anti-microbial action and sensory-derived malodour counteraction.
  • Group A ingredients are listed below, where names in parentheses represents equivalent names—either trivial names commonly used within the fragrance and flavour industry, or tradenames that are sources for the material cited.
    • Group A Materials:
    • (3Z)-hex-3-enyl acetate (cis-3-hexenyl acetate),
    • 3-(1,3-benzodioxol-5-yl)-2-methylpropanal [Helional™(IFF)],
    • (3Z)-hex-3-en-1-ol (cis-3-hexenol)
    • 1-[4-(methyloxy)phenyl]ethanone (paramethoxy acetophenone),
    • 3-methyl-5-phenylpentan-1-ol [Mefrosol™(G)],
    • 5-heptyldihydrofuran-2(3H)-one (undecalactone gamma),
    • phenylmethyl acetate (benzyl acetate),
    • 2-(4-methylcyclohex-3-en-1-yl)propan-2-ol (terpineol alpha),
    • (3E)-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one (ionone alpha),
    • (3E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one (ionone beta),
    • 4-hydroxy-3-(methyloxy)benzaldehyde (vanillin),
    • 1-methyl-3-(2-methylpropyl)cyclohexanol [Rossitol™ (G)],
    • 7,9-dimethylspiro[5.5]undecan-3-one [Dispirone™ (G)],
    • perfume 1 being Lavandin AB8381™,
    • methyl 2,4-dihydroxy-3,6-dimethylbenzoate (moss oakmoss synthetic),
    • 3,7-dimethyloctan-1-ol (tetrahydrogeraniol),
    • 2-(methyloxy)-4-propylphenol (dihydroeugenol),
    • perfume 2 being Rosenta AB8428™,
    • 1-{[(1R,2S)-2-(1,1-dimethylethyl)cyclohexyl]oxy}butan-2-ol [Amber Coretm (G)],
    • perfume 3 being Headspace Freesia AB7254A™,
    • 5-hexyldihydrofuran-2(3H)-one (decalactone gamma),
    • prop-2-enyl [(2-methylbutyl)oxy]acetate (Allyl amyl glycolate),
    • 1,3-benzodioxole-5-carbaldehyde (heliotropin),
    • [4-(1-methylethyl)cyclohexyl]methanol [Mayol™(F)],
    • 2-hexylcyclopent-2-en-1-one (iso-jasmone),
    • methyl (2E)-3-phenylprop-2-enoate (methyl cinnamate),
    • 2,6-dimethyloct-7-en-2-ol (dihydromyrcenol),
    • 2-methyl-3-[4-(1-methylethyl)phenyl]propanal (Cyclamen aldehyde).
      Group B ingredients:
    • 2-phenylethanol (phenyl ethyl alcohol);
    • 3,7-dimethyloctan-3-ol (tetrahydrolinalol);
    • 2-(methyloxy)-4-[(1E)-prop-1-enyl]phenyl acetate (isoeugenyl acetate);
    • 4-(methyloxy)benzaldehyde (anisic aldehyde);
    • (2E)-1-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-en-1-one (damascone alpha);
    • perfume 4 being Bergamot AB8392™;
    • (3E)-3-methyl-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one (Methyl ionone alpha iso);
    • Cyclopentadecanone[Silvanone™ (G)];
    • Oxacycloheptadecan-2-one (Silvanone™ (G), cyclohexadecanolide);
    • prop-2-enyl 3-cyclohexylpropanoate (allyl cyclo hexyl propionate);
    • 3-[3-(1-methylethyl)phenyl]butanal [Florohydral™ (G)];
    • (3Z)-hex-3-enyl methyl carbonate (cis-3-hexenyl methyl carbonate);
    • (1-methyl-2-{[(1S,3R,5R)-1,2,2-trimethylbicyclo[3.1.0]hex-3-yl]methyl}cyclopropyl)methanol [Javanol™(G)];
    • [3,3-bis(methyloxy)propyl]benzene (dimethyl hydro cinnamyl);
    • perfume 5 being Coumarex I Mod™ (IFF);
    • tricyclo[5.2.1.0{2,6}]dec-4-en-8-yl propanoate [Florocyclene™ (G)].
    Key:
    • G=Givaudan;
    • IFF=International Flavours and Fragrances;
    • F=Firmenich
      wherein perfumes 1 to 5 have the following compositions:
  • Ingredient Perfume 1 Perfume 2 Perfume 3 Perfume 4 Perfume 5
    Allylamyl glycolate 0.8
    Anisaldehyde 0.3
    Benzophenone 2.0
    Borneol 1.0
    Camphene 0.8
    Camphor 9.2
    Caryophyllene 4.5
    Cedarwood Texan oil 0.8
    Cineole 7.0
    Citral Diethylacetal 1.5
    Citronellyl formate 1.8
    Citronellyl propionate 2.5
    Dihydrolinalol 6.5
    Dihydro myrcenyl acetate 11.0
    Dihydro Terpinyl Acetate 13.5 31.5
    2,6-Dimethylheptan-2-ol 2.0
    Dipropylene glycol 5.0 88.0
    Geranylacetate 5.0
    Geranylacetone 1.0
    Geranyl formate 1.2
    Hercolyn DE (TM) 4.5
    gamma-hexalone 5.6
    beta-ionone 3.0 24.5
    Linalyl acetate 1.0 32.0
    Mefrosol (TM) 10.0 14.0
    3-Methylbut-2-enyl benzoate 4.5
    Neryl acetate 1.0
    Ocimene 1.0
    para-tert-butylcyclohexyl acetate 4.5
    Phenyl acetaldehyde dimethylacetal 2.0
    2-phenylethyl alcohol 27.0
    2-phenylethyl phenylacetate 24.0
    2-phenylethyl salicylate 1.0
    alpha-pinene 1.4
    beta-pinene 6.8
    Clary sage oil 0.8
    gamma-terpinene 6.0
    alpha-terpineol 4.2 12.2
    Terpinyl acetate 17.9
    alpha-terpinyl isobutyrate 2.5
    Tetrahydrogeraniol 1.4
    Tetrahydrolinalol 60.3 4.0
    Tetrahydrolinalyl acetate 4.5
    Minor components 6.8 5.3 3.0 4.8 1.6
    Totals 100 100 100 100 100
    Key
    Mefrosol is 3-methyl-5-phenylpentan-1-ol
    Hercolyn DE is a mixture of methyl dihydroabietate and tetrahydroabietate
  • Particularly preferred Group A materials are:
    • (3Z)-hex-3-enyl acetate; 3-(1,3-benzodioxol-5-yl)-2-methylpropanal; (3Z)-hex-3-en-1-ol; 3-methyl-5-phenylpentan-1-ol; 5-heptyldihydrofuran-2(3H)-one; phenylmethyl acetate; 2-(4-methylcyclohex-3-en-1-yl)propan-2-ol; 2,6-dimethyloct-7-en-2-ol; (3E)-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-n-2-one; (3E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl) but-3-en-2-one; 4-hydoxy-3-(methyloxy)benzaldehyde; 1,3-benzodioxole-5-carbaldehyde.
  • It has also been discovered that the presence of different perfume solvents within the composition may affect activity slightly. Embodiments incorporating triethyl citrate are preferred.
    • EXAMPLES Example 1 MIC Estimation for Fragrance and Fragrance Ingredients
  • The minimum inhibitory concentration of perfumes may be determined by the following method.
  • Stock solutions (8% w/w) of perfume were prepared in sterile tryptone soya broth.
    • Test Strain:
  • Proteus vulgaris NCTC 4175 (National Collection of Type Cultures, Public Health Laboratory Service, Central Public Health Laboratory, 61 Colindale Avenue, London)
  • Cultures were grown in 10 ml of tryptone soya broth (TSB) (Oxoid, Basingstoke, UK), for 16-24 hours, in shaken flasks at 37° C. The cultures were then diluted in sterile 0.1% special peptone solution (Oxoid, Basingstoke, UK) to give a concentration of bacteria of approximately 106 colony-forming units (cfu) per ml.
  • Test ingredients were diluted in sterile TSB. For each test bacterial culture, each row of a standard, 96-well plastic microtitre plate (labelled A-H) was allocated to one sample, thus eight samples per plate. Row H contained only TSB for use as a bacterial control to indicate the degree of turbidity resulting from bacterial growth in the absence of any test material. Aseptically, 200 μl of the initial dilution of ingredient was transferred to the 1st and 7th well of the appropriate row. All other test wells were filled with 100 μl of sterile TSB using an 8-channel micropipette. The contents of each of the wells in column 1 were mixed by sucking samples up and down in pipette tips, before 100 μl was transferred to column 2. The same sterile pipette tips were used to transfer 100 μl of each well in column 7, into the appropriate well in column 8. This set of eight tips was then discarded into disinfectant solution. Using eight fresh, sterile tips the process was repeated by transferring 100 μl from column 2 into column 3 (and 8 into 9). The process was continued until all wells in columns 6 and 12 contained 200 μl. After mixing, 100 μl was discarded from wells in columns 6 and 12 to waste. Finally, 100 μl of pre-diluted bacterial culture (approx. 106 cfu/ml) was added, thus giving 200 μl final volume in each well.
  • A blank plate was prepared for each set of eight samples in exactly the same way, except that 100 μl of sterile 0.1% special peptone was added instead of bacterial culture. Test and control plates were sealed using autoclave tape and incubated for 18 hours at 37° C.
  • The microtitre plate reader (Thermo Multiskan Ascent) was preset to gently agitate the plates, to mix the contents. The absorbance at 540 nm was used as a measure of turbidity resulting from bacterial growth. Both control (un-inoculated plate) and inoculated plates were read for each set of samples. The absorbance readings from the control plate were subtracted from the relevant inoculated plate readings thus removing turbidity due to perfume and possible colour changes during incubation. Thus the corrected readings generated were absorbances resulting from turbidity from bacterial growth. The MIC was taken as the concentration of ingredient required to inhibit growth so that the average change in absorbance during the incubation period was <0.3.
    • Example 2 Urease Assay—Estimation of Fragrance and Fragrance Ingredients Effect on Ammonia Production
  • The method adopted was based on the rapid method devised by C. A. Stuart, Elizabeth van Stratum and Robert Rustigan Further Studies on Urease Production by Proteus and Related Organisms J. Bacteriol. 1945, 49: 437-444.
  • SSR Medium: 380 ml distilled water, 364 mg KH2PO4, 380 mg Na2HPO4, 8 g Urea, 40 mg Yeast extract, 20 ml 0.02% phenol red indicator, pH 6.8, solution filter sterilised. Culture: Liquid culture of P. vulgaris NCTC4175 was prepared by adding loops of fresh culture from solid media (Tryptone Soya Agar) to sterile 0.1% special peptone solution. Absorbance of culture was adjusted to be OD610 nm>2.3
  • Fragrances were aseptically prepared at 2500 ppm in medium in duplicate (5 ml volumes) using solubiliser Synperonic 91/10 at ratio of 1:2 fragrance: solubiliser. In addition 5 ml volumes of positive and negative controls were prepared. Positive controls and all test solutions were inoculated by adding 200 μl of prepared culture, mixed and incubated for 24 hours @ 37oC. No culture was added to the negative growth controls. Initially solutions were orange in colour. Urease activity can be noted by the production of a purple/red colour, indicating high pH resulting from ammonia production. The degree of urease activity/ammonia production was assessed by pH electrode.
    • Example 3 Perfume Compositions
  • Fragrance formulations 3.2, 3.4, and 3.8 detailed in Table 1 were created following the creative guidelines of the present invention. Formulations, 3.1, 3.3, 3.5, 3.6 and 3.7 are comparatives that fall outside these guidelines. All examples bar numbers 3.5 and 3.6 meet the Urease Inhibition Assay target of a difference of 1.2 pH units compared to the positive control. However only Formulations 3.2, 3.4 and 3.8 achieve this effect at sub-MIC level. These three perfumes were also evaluated in a urine malodour test as described in example 3 of PCT/GB2007/001172 using malodour model A of example 1 therein. All three were found to be effective in reducing the perception of the urine malodour.
  • TABLE 1
    Perfume Formulations (% w/w)
    Ingredient 3.1 3.2 3.3 3.4 3.5 3.6 3.7 3.8
    Acetyl tributyl citrate 10 10 5 5
    Allyl amyl glycolate (A) 1 3
    Amyl salicylate 5 5 4 7
    Anisic aldehyde (B) 5 4 0.5
    Bangaloltm(G) 0.3 0.3
    Benzyl acetate (A) 1
    cis-3-hexenol (A) 0.5 0.5
    cis-3-hexenyl salicylate 1
    coumarex I modtm(B) 5
    Cyclamen aldehyde (A) 5
    Decalactone gamma (A) 0.5
    Dihydromyrcenol (A) 10 5
    Dispironetm (G) (A) 0.1 0.5
    Ethylene brassylate 10 15 10 14.5 12 12
    Ethyl safranatetm (G) 0.2
    Florosatm (G) 0.2 0.5
    Habanolidetm(F) 1 2 3
    Helionaltm (A) 1 1 1 1 2
    Heliotropin (A) 3 1 1 2
    Hexyl salicylate 5 12 10 12 10 15
    Ionone alpha (A) 2
    Mayoltm (F) (A) 1
    Mefrosoltm (G) (A) 0.9 1 1 1 2.5
    Methyl dihydrojasmonate 8 14 15 15 10 8
    para tert butyl cyclo hexyl 5
    acetate
    Moss oakmoss synthetic (A) 0.1
    Phenoxyethanol 5 10 5
    Phenyl ethyl alcohol (B) 10 7.5 5 6.5 7 10
    Rossitoltm (G) (A) 2
    Silvanonetm (G) (B) 1
    Terpineol alpha (A) 6 5 2
    Tetrahydrogeraniol (A) 1.5 3
    Tetrahydrolinalol (B) 5 2 1 1 3 10.5
    Triethyl citrate 34 36 50 33 48 50 45 50
    Undecalactone gamma (A) 0.5 0.5
    Vanillin (A) 2 1.9 2 1
    Total Group A ingredients 20 5.5 15 7 5 0 14.5 10
    Total Group B ingredients 16 19.5 10 8 10 0 20.5 0
    Total Group A + Group B 36 25 25 15 15 0 35 10
    KEY: (A) = group A material:
    (B) = Group B material
    (G) = Givaudan;
    (F) = Firmenich
  • Following the methods outlined previously, the above examples give results detailed in Table 2.
  • TABLE 2
    Results of MIC and Urease inhibition assays
    Urease Inhibition Assay Results
    at 2500 ppm MIC assay
    pH unit difference MIC vs Pr. vulgaris
    Fragrance Average pH from +ve control (ppm)
    Example 3.1 7.50 1.60 2500
    Example 3.2 7.85 1.25 5000
    Example 3.3 7.69 1.41 1250
    Example 3.4 7.67 1.43 10000
    Example 3.5 8.44 0.66 10000
    Example 3.6 8.78 0.32 10000
    Example 3.7 7.64 1.46 2500
    Example 3.8 7.58 1.52 5000
    +ve control 9.10 N/A N/A
    −ve control 6.99 N/A N/A

Claims (9)

1. A perfume composition comprising between 10% and 30% in total by weight of perfume ingredients selected from two groups:
Group A, consisting of (3Z)-hex-3-enyl acetate; 3-(1,3-benzodioxol-5-yl)-2-methylpropanal; (3Z)-hex-3-en-1-ol; 1-[4-(methyloxy)phenyl]ethanone; 3-methyl-5-phenylpentan-1-ol; 5-heptyldihydrofuran-2(3H)-one; phenylmethyl acetate; 2-(4-methylcyclohex-3-en-1-yl)propan-2-ol; (3E)-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one; (3E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one; 4-hydroxy-3-(methyloxy)benzaldehyde; 1-methyl-3-(2-methylpropyl)cyclohexanol; 7,9-dimethylspiro[5.5]undecan-3-one; perfume 1 being Lavandin AB8381™ ; methyl 2,4-dihydroxy-3,6-dimethylbenzoate; 3,7-dimethyloctan-1-ol; 2-(methyloxy)-4-propylphenol; perfume 2 being Rosenta AB8428™m; 1-{[(1R,2S)-2-(1,1-dimethylethyl)cyclohexyl]oxy}butan-2-ol; perfume 3 being Headspace Freesia AB7254A™; 5-hexyldihydrofuran-2(3H)-one; prop-2-enyl [(2-methylbutyl)oxy]acetate; 1,3-benzodioxole-5-carbaldehyde; [4-(1-methylethyl)cyclohexyl]methanol; 2-hexylcyclopent-2-en-1-one; methyl (2E)-3-phenylprop-2-enoate; 2,6-dimethyloct-7-en-2-ol; 2-methyl-3-[4-(1-methylethyl)phenyl]propanal; and
Group B consisting of 2-phenylethanol; 3,7-dimethyloctan-3-ol (tetrahydro linalol), 2-(methyloxy)-4-[(1E)-prop-1-enyl]phenyl acetate; 4-(methyloxy)benzaldehyde; (2E)-1-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-en-1-one; perfume 4 being Bergamot AB8392™, (3E)-3-methyl-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one; cyclopentadecanone; cyclohexadecanolide; prop-2-enyl 3-cyclohexylpropanoate; 3-[3-(1-methylethyl)phenyl]butanal; (3Z)-hex-3-enyl methyl carbonate; (1-methyl-2-{[(1S,3R,5R)-1,2,2-trimethylbicyclo[3.1.0]hex-3-yl]methyl}cyclopropyl)methanol; [3,3-bis(methyloxy)propyl]benzene; perfume 5 being Coumarex I Mod™;
tricyclo[5.2.1.0{2,6}]dec-4-en-8-yl propanoate;
with the provisos that offer 5% bat less than 15% of the perfume composition must comprise Group A ingredients, and for compositions comprising less than 10% of Group A ingredients the agregate percentage of Group B ingredients present must be at least
equal to the expression 2*(10-A%) where A% is the total percentage of Group A ingredients in the composition.
2. A perfume composition according to claim 1 wherein it comprises at least 3, preferably at least 4, most preferably at least 6 Group A ingredients.
3. A perfume composition according to claim 1 or claim 2, wherein the Group A ingredients are selected from:
(3)-hex-3-enyl acetate;
3-(1,3-benzodioxol-5yl)-2-methylpropanal; (3Z)-hex-3-en-1-ol;
3-methyl-5-phenylpentan-1-ol; 5-heptyldihydrofuran-2(3H)-one;
phenylmethyl acetate; 2-(4-methylcyclohex-3en-1-yl)propan-2-ol;
2,6-dimethyloct-7en-2-ol; (3E)-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one;
(3E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3en-one; 4-hydoxy-3-(methyloxy)benzaldehyde;
1,3-benzodioxole-5-carbaldehyde.
4. A method of preventing or ameliorating urine malodour comprising the step of: bringing an effective amount of a composition according to claim 1 into contact with urine or urine residues.
5. A consumer product comprising a perfume composition according to claim 1.
6. A urine malodor preventing or ameliorating article urine malodour, comprising an effective amount of a perfume composition according to claim 1.
7. A catamenial article according to claim 6.
8. An incontinence control article according to claim 6.
9. A method inhibiting the formation of ammonia from urea the method comprising the step of: contacting urea with a perfume composition according to claim 1.
US12/375,756 2006-08-05 2007-08-03 Perfume Compositions Abandoned US20090257974A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB0615583.2 2006-08-05
GB0615583A GB0615583D0 (en) 2006-08-05 2006-08-05 Perfume compositions
PCT/GB2007/002980 WO2008017820A1 (en) 2006-08-05 2007-08-03 Perfume compositions

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB2007/002980 A-371-Of-International WO2008017820A1 (en) 2006-08-05 2007-08-03 Perfume compositions

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US13/651,899 Division US20130039876A1 (en) 2006-08-05 2012-10-15 Perfume Compositions
US13/651,958 Continuation US9011829B2 (en) 2006-08-05 2012-10-15 Perfume compositions

Publications (1)

Publication Number Publication Date
US20090257974A1 true US20090257974A1 (en) 2009-10-15

Family

ID=37027299

Family Applications (5)

Application Number Title Priority Date Filing Date
US12/375,756 Abandoned US20090257974A1 (en) 2006-08-05 2007-08-03 Perfume Compositions
US13/651,958 Active US9011829B2 (en) 2006-08-05 2012-10-15 Perfume compositions
US13/651,899 Abandoned US20130039876A1 (en) 2006-08-05 2012-10-15 Perfume Compositions
US14/548,858 Abandoned US20150079017A1 (en) 2006-08-05 2014-11-20 Perfume Compositions
US14/658,871 Active US10722607B2 (en) 2006-08-05 2015-03-16 Perfume compositions

Family Applications After (4)

Application Number Title Priority Date Filing Date
US13/651,958 Active US9011829B2 (en) 2006-08-05 2012-10-15 Perfume compositions
US13/651,899 Abandoned US20130039876A1 (en) 2006-08-05 2012-10-15 Perfume Compositions
US14/548,858 Abandoned US20150079017A1 (en) 2006-08-05 2014-11-20 Perfume Compositions
US14/658,871 Active US10722607B2 (en) 2006-08-05 2015-03-16 Perfume compositions

Country Status (7)

Country Link
US (5) US20090257974A1 (en)
EP (1) EP2049638B1 (en)
CN (1) CN101501169A (en)
BR (1) BRPI0715173B1 (en)
ES (1) ES2395409T3 (en)
GB (1) GB0615583D0 (en)
WO (1) WO2008017820A1 (en)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090263344A1 (en) * 2006-08-05 2009-10-22 Givaudan Nederland Services B.V. Perfume Compositions
US20100292128A1 (en) * 2007-06-11 2010-11-18 Givaudan Sa Organic Compounds
WO2014056848A1 (en) * 2012-10-08 2014-04-17 Dsm Ip Assets B.V. Flavor and fragrance formulation (iii)
WO2014082834A1 (en) * 2012-11-27 2014-06-05 Henkel Ag & Co. Kgaa Aromatic substance mixtures containing hexyl salicylate
US20160129144A1 (en) * 2009-12-17 2016-05-12 The Procter & Gamble Company Malodor control composition having a mixture of volatile aldehydes and methods thereof
WO2017090518A1 (en) * 2015-11-24 2017-06-01 花王株式会社 Urine odor suppressor
JP2017101224A (en) * 2015-11-24 2017-06-08 花王株式会社 Urinary odor suppressor
US20190218476A1 (en) * 2016-09-14 2019-07-18 Givaudan Sa Fragrance compositions
JP2019531267A (en) * 2016-08-05 2019-10-31 フイルメニツヒ ソシエテ アノニムＦｉｒｍｅｎｉｃｈ Ｓａ Antimicrobial composition
US10722607B2 (en) 2006-08-05 2020-07-28 Givaudan S.A. Perfume compositions

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MX375207B (en) * 2016-01-28 2025-03-06 Johnson & Johnson Consumer Inc PERFUME COMPOSITIONS.

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3195629A (en) * 1962-12-31 1965-07-20 Pan American Petroleum Corp Use of partially oxidized oil in a waterflooding process
US5837671A (en) * 1995-11-10 1998-11-17 Givaudan-Roure (International) Sa Organoleptic compound and composition
US5919440A (en) * 1997-05-05 1999-07-06 Procter & Gamble Company Personal care compositions containing an odor masking base
US5942217A (en) * 1997-06-09 1999-08-24 The Procter & Gamble Company Uncomplexed cyclodextrin compositions for odor control
US5990076A (en) * 1997-09-09 1999-11-23 Firemenich Sa Benzodioxepinone and its use in perfumery
US20020192174A1 (en) * 2001-03-23 2002-12-19 Ken Kawakami Perfume mixtures with increased odor intensity
US20050154133A1 (en) * 2002-03-08 2005-07-14 Friedrich Engelhardt Polymer mixtures with improved odor control
US7585833B2 (en) * 2005-02-17 2009-09-08 Givaudan Fragrances Corporation Malodor covering perfumery

Family Cites Families (59)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US588961A (en) 1897-08-31 Executrix of albert m
GB841921A (en) * 1958-02-11 1960-07-20 Polak & Schwarz Internationaal 2-piperonyl-propanal, a new perfume, and process for making same
US3945950A (en) 1974-10-02 1976-03-23 Universal Oil Products Company Solid perfumed compositions of matter
US4113645A (en) 1977-07-26 1978-09-12 Polak's Frutal Works, Inc. Bleach compositions containing perfume oils
US4548821A (en) 1984-03-14 1985-10-22 International Flavors & Fragrances Inc. Flavoring with tertiary pentamethylindanol derivatives
US4740366A (en) 1986-01-21 1988-04-26 Church & Dwight Co., Inc. Air deodorizer composition and method
US4808569A (en) 1986-10-24 1989-02-28 Gaf Corporation Fragrance additive
US5089162A (en) 1989-05-08 1992-02-18 Lever Brothers Company, Division Of Conopco, Inc. Cleaning compositions with bleach-stable colorant
GB9022147D0 (en) 1990-10-11 1990-11-21 Unilever Plc Perfumed underarm hygiene products
MX9201361A (en) 1991-04-15 1992-10-01 Kimberly Clark Co AN ABSORBING ARTICLE CONTAINING ANHYDROUS DEODORANT.
DE69221087T2 (en) 1991-11-08 1997-11-13 Quest Int Perfume compilation
US5260053A (en) 1991-12-30 1993-11-09 Tom's Of Maine Herbal deodorant
CA2072914C (en) 1992-03-27 2004-04-20 James Richard Gross Method for reducing malodor in absorbent products and products formed thereby
ATE140723T1 (en) 1992-12-11 1996-08-15 Quest Int DEMETHYL-CYCLOHEXANECARBOXYLIC ACID ESTERS IN PERFUMERY
IT1260656B (en) 1993-04-23 1996-04-22 P & G Spa ABSORBENT ITEM INCLUDING A MATERIAL FOR THE CONTROL OF THE ODOR AND ITS USE.
DE4411664A1 (en) 1994-04-05 1995-10-12 Beiersdorf Ag Novel deodorant and antimicrobial compositions for use in cosmetic or topical preparations
WO1996012467A1 (en) 1994-10-20 1996-05-02 The Procter & Gamble Company Personal treatment compositions and/or cosmetic compositions containing enduring perfume
JP3356242B2 (en) 1995-03-08 2002-12-16 高砂香料工業株式会社 (6E) Perfume containing 2,3-dihydrofarnesol
JP3740515B2 (en) 1995-03-25 2006-02-01 クエスト・インターナショナル・ビー・ブイ Fragrance
EP0912149A1 (en) 1996-06-07 1999-05-06 The Procter & Gamble Company Absorbent article comprising a polyfunctionally substituted aromatic chelating agent for odour control
US5769833A (en) 1996-12-12 1998-06-23 Hasse; Margaret Henderson Diaper having perfume zones
AU739247B2 (en) 1996-12-17 2001-10-04 Procter & Gamble Company, The Absorbent articles with odor control system
US5874073A (en) 1997-05-05 1999-02-23 Procter & Gamble Styling shampoo compositions containing an odor masking base
ID28183A (en) * 1997-06-09 2001-05-10 Procter & Gamble FOOD CLEANING COMPOSITION CONTAINING CYCODODSTRINE
US5874070A (en) 1997-06-09 1999-02-23 The Procter & Gamble Company Compositions for reducing body odor
TW527191B (en) 1997-07-09 2003-04-11 Kao Corp Hair treatment composition
EP0894502A1 (en) 1997-07-30 1999-02-03 The Procter & Gamble Company Cyclodextrin-containing odour control material for absorbent articles
US6025186A (en) 1997-08-14 2000-02-15 Novo Nordisk A/S Reduction of malodor
DE69838130T2 (en) * 1998-06-15 2008-04-10 The Procter & Gamble Company, Cincinnati fragrance compositions
GB9814648D0 (en) 1998-07-07 1998-09-02 Quest Int Sub-lethal perfumes
GB9814653D0 (en) 1998-07-07 1998-09-02 Quest Int Method of reducing or preventing malodour
EP1140223B1 (en) 1998-12-22 2004-08-04 Quest International B.V. Compositions and methods for the reduction of malodour
EP1034800A1 (en) 1999-03-05 2000-09-13 The Procter & Gamble Company Articles having an odour control system comprising an oxidising agent and an odour absorbing agent
JP4520682B2 (en) * 1999-12-13 2010-08-11 シムライズ・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング・ウント・コンパニー・コマンジツト・ゲゼルシヤフト Odor neutralizer
EP1116788A1 (en) * 2000-01-12 2001-07-18 The Procter & Gamble Company Pro-perfume composition
WO2001093814A2 (en) * 2000-06-02 2001-12-13 The Procter & Gamble Company Fragrance compositions
US6403075B1 (en) 2000-03-15 2002-06-11 Dragoco Gerberding & Co. Ag Odor suppression in ammonia-containing cosmetic products
US6372513B1 (en) 2000-04-19 2002-04-16 Ansys Technologies, Inc. Device and process for lateral flow saliva testing
EP1190725A3 (en) 2000-09-25 2003-01-29 Givaudan SA Process for maintaining fragrance perception in the presence of an absorbent material
EP1214878A1 (en) 2000-12-15 2002-06-19 The Procter & Gamble Company Methods, compositions and articles for control of malodor produced by urea-containing body fluids
GB0031047D0 (en) * 2000-12-20 2001-01-31 Quest Int Perfume compositions
JP2003147386A (en) * 2001-11-09 2003-05-21 Soda Aromatic Co Ltd Fragrance composition and fragrant cosmetic comprising the same
US6903067B2 (en) * 2001-12-18 2005-06-07 Takasago International Corporation Fragrance composition containing 3-(3-hexenyl)-2-cyclopentenone
US6852904B2 (en) 2001-12-18 2005-02-08 Kimberly-Clark Worldwide, Inc. Cellulose fibers treated with acidic odor control agents
US6767553B2 (en) 2001-12-18 2004-07-27 Kimberly-Clark Worldwide, Inc. Natural fibers treated with acidic odor control/binder systems
JP2003277246A (en) 2002-03-22 2003-10-02 Takasago Internatl Corp Deodorant composition
US20030194416A1 (en) * 2002-04-15 2003-10-16 Adl Shefer Moisture triggered release systems comprising aroma ingredients providing fragrance burst in response to moisture
JP3714305B2 (en) 2002-07-11 2005-11-09 ダイキン工業株式会社 Refrigeration apparatus and refrigerant charging method for refrigeration apparatus
GB0216940D0 (en) * 2002-07-20 2002-08-28 Givaudan Sa Improvements in or relating to organic compounds
WO2004010325A1 (en) 2002-07-22 2004-01-29 Contivo, Inc. Method and system for transforming semantically related documents
JP3947149B2 (en) * 2002-10-28 2007-07-18 高砂香料工業株式会社 Deodorant composition
BRPI0410150A (en) * 2003-05-09 2006-05-09 Quest Int Serv Bv method of neutralizing or reducing odors associated with body fluids or solids, use of a fragrance material composition, and, article
US20040241333A1 (en) 2003-05-30 2004-12-02 The Procter & Gamble Company Composition and process for coating a substrate
US20040266302A1 (en) 2003-06-30 2004-12-30 Disalvo Anthony L. Absorbent article having odor control properties
US7234648B2 (en) 2003-10-31 2007-06-26 The Procter And Gamble Company Volatile substance-controlling composition
EP1748800B1 (en) 2004-05-12 2008-10-22 Quest International Services B.V. Odour reduction compositions
GB0504924D0 (en) * 2005-03-10 2005-04-20 Quest Int Serv Bv Perfume compositions
GB0615580D0 (en) 2006-08-05 2006-09-13 Quest Int Serv Bv Perfume compositions
GB0615583D0 (en) 2006-08-05 2006-09-13 Quest Int Serv Bv Perfume compositions

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3195629A (en) * 1962-12-31 1965-07-20 Pan American Petroleum Corp Use of partially oxidized oil in a waterflooding process
US5837671A (en) * 1995-11-10 1998-11-17 Givaudan-Roure (International) Sa Organoleptic compound and composition
US5919440A (en) * 1997-05-05 1999-07-06 Procter & Gamble Company Personal care compositions containing an odor masking base
US5942217A (en) * 1997-06-09 1999-08-24 The Procter & Gamble Company Uncomplexed cyclodextrin compositions for odor control
US5990076A (en) * 1997-09-09 1999-11-23 Firemenich Sa Benzodioxepinone and its use in perfumery
US20020192174A1 (en) * 2001-03-23 2002-12-19 Ken Kawakami Perfume mixtures with increased odor intensity
US20050154133A1 (en) * 2002-03-08 2005-07-14 Friedrich Engelhardt Polymer mixtures with improved odor control
US7585833B2 (en) * 2005-02-17 2009-09-08 Givaudan Fragrances Corporation Malodor covering perfumery

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090263344A1 (en) * 2006-08-05 2009-10-22 Givaudan Nederland Services B.V. Perfume Compositions
US8821847B2 (en) 2006-08-05 2014-09-02 Givaudan Nederland Services B.V. Perfume compositions
US10722607B2 (en) 2006-08-05 2020-07-28 Givaudan S.A. Perfume compositions
US20100292128A1 (en) * 2007-06-11 2010-11-18 Givaudan Sa Organic Compounds
US9012391B2 (en) * 2007-06-11 2015-04-21 Givaudan Sa Organic compounds
US20160129144A1 (en) * 2009-12-17 2016-05-12 The Procter & Gamble Company Malodor control composition having a mixture of volatile aldehydes and methods thereof
WO2014056848A1 (en) * 2012-10-08 2014-04-17 Dsm Ip Assets B.V. Flavor and fragrance formulation (iii)
CN104704094A (en) * 2012-10-08 2015-06-10 帝斯曼知识产权资产管理有限公司 Flavor and fragrance formulation (iii)
US9567286B2 (en) 2012-10-08 2017-02-14 Dsm Ip Assets B.V. Flavor and fragrance formulation (III)
WO2014082834A1 (en) * 2012-11-27 2014-06-05 Henkel Ag & Co. Kgaa Aromatic substance mixtures containing hexyl salicylate
JP2017101224A (en) * 2015-11-24 2017-06-08 花王株式会社 Urinary odor suppressor
CN108289973A (en) * 2015-11-24 2018-07-17 花王株式会社 Urinate smelly inhibitor
WO2017090518A1 (en) * 2015-11-24 2017-06-01 花王株式会社 Urine odor suppressor
CN108289973B (en) * 2015-11-24 2021-03-30 花王株式会社 Urine odor inhibitor
JP2019531267A (en) * 2016-08-05 2019-10-31 フイルメニツヒ ソシエテ アノニムＦｉｒｍｅｎｉｃｈ Ｓａ Antimicrobial composition
JP7051813B2 (en) 2016-08-05 2022-04-11 フイルメニツヒ ソシエテ アノニム Antimicrobial composition
JP2022088563A (en) * 2016-08-05 2022-06-14 フイルメニツヒ ソシエテ アノニム Antimicrobial composition
JP7405893B2 (en) 2016-08-05 2023-12-26 フイルメニツヒ ソシエテ アノニム antimicrobial composition
US20190218476A1 (en) * 2016-09-14 2019-07-18 Givaudan Sa Fragrance compositions
US10982173B2 (en) * 2016-09-14 2021-04-20 Givaudan Sa Fragrance compositions

Also Published As

Publication number Publication date
BRPI0715173B1 (en) 2017-06-06
US20130039877A1 (en) 2013-02-14
GB0615583D0 (en) 2006-09-13
WO2008017820A1 (en) 2008-02-14
US20150182656A1 (en) 2015-07-02
ES2395409T3 (en) 2013-02-12
EP2049638B1 (en) 2012-10-03
EP2049638A1 (en) 2009-04-22
US20150079017A1 (en) 2015-03-19
US10722607B2 (en) 2020-07-28
US9011829B2 (en) 2015-04-21
BRPI0715173A8 (en) 2017-01-24
US20130039876A1 (en) 2013-02-14
CN101501169A (en) 2009-08-05
BRPI0715173A2 (en) 2015-02-18

Similar Documents

Publication Publication Date Title
US10722607B2 (en) Perfume compositions
US8821847B2 (en) Perfume compositions
JP5548451B2 (en) β-glucuronidase inhibitor
EP1884251B1 (en) Use of fragrance compositions for restricting the formation of indole from faecal and urine based soils
WO2019008089A1 (en) 2,4-disubstituted pyridines as malodor counteracting ingredients
US11691036B2 (en) Macrocyclic ketone as malodor counteracting ingredient
US8580728B2 (en) Use of fragrance compositions for the prevention of the development of indole base malodours from fecal and urine based soils
JP5619484B2 (en) Composition for suppressing urine odor production
JP2010246905A (en) Composition for restraining uraroma formation
JP6581778B2 (en) Urine odor deodorant
JP5806716B2 (en) β-glucuronidase inhibitor
JP2010227130A (en) Beta-glucuronidase inhibitor
US20240390544A1 (en) 2,4-disubstituted pyridines as malodor counteracting ingredients

Legal Events

Date Code Title Description
AS Assignment

Owner name: GIVAUDAN NEDERLAND SERVICES B.V., NETHERLANDS

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:EVANS, GORDON MICHAEL;PROVAN, ALAN FORBES;BRADSHAW, DAVID JONATHAN;AND OTHERS;REEL/FRAME:022279/0824;SIGNING DATES FROM 20090113 TO 20090120

STCB Information on status: application discontinuation

Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION

点击 这是indexloc提供的php浏览器服务，不要输入任何密码和下载