WO2000001354A1 - Cosmetic composition - Google Patents

Cosmetic composition Download PDF

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Publication number
WO2000001354A1
WO2000001354A1 PCT/GB1999/002143 GB9902143W WO0001354A1 WO 2000001354 A1 WO2000001354 A1 WO 2000001354A1 GB 9902143 W GB9902143 W GB 9902143W WO 0001354 A1 WO0001354 A1 WO 0001354A1
Authority
WO
WIPO (PCT)
Prior art keywords
lysozyme
ncimb
vfa
deodorising
flasks
Prior art date
Application number
PCT/GB1999/002143
Other languages
French (fr)
Inventor
John Casey
Alexander Gordon James
Original Assignee
Unilever Plc
Unilever Nv
Hindustan Lever Limited
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 Unilever Plc, Unilever Nv, Hindustan Lever Limited filed Critical Unilever Plc
Priority to AU46360/99A priority Critical patent/AU4636099A/en
Publication of WO2000001354A1 publication Critical patent/WO2000001354A1/en

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q15/00—Anti-perspirants or body deodorants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/463—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfuric acid derivatives, e.g. sodium lauryl sulfate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/74—Biological properties of particular ingredients
    • A61K2800/78—Enzyme modulators, e.g. Enzyme agonists
    • A61K2800/782—Enzyme inhibitors; Enzyme antagonists

Definitions

  • This invention relates to deodorant or antiperspirant compositions.
  • it relates to compositions comprising an active capable of selectively increasing the population of naturally occurring deodorising microorganisms on the surface of the skin.
  • the invention also relates to a method of reducing or preventing body malodour by applying to the surface of the skin a composition comprising said active.
  • a deodorising composition will attempt to significantly reduce or prevent body odour by reducing either perspiration or the number of microorganisms on the surface of the skin.
  • the former is usually referred to as an antiperspirant composition and the latter a deodorant.
  • Compositions reducing perspiration often comprise a metal salt, such as aluminium or zirconium salt which blocks the sweat pores. This method is very simple yet a perspiration reduction of more than 50% is rarely achieved.
  • Deodorants reduce the numbers of microorganisms on the surface of the skin. It is well known that sweat is odourless until it has been degraded by the skin microflora. Typical deodorants include ethanol and triclosan (2,4,4' -trichloro, 2 ' -hydroxy-diphenyl ether) which is a well known antimicrobial agent. However, the deodorising effect obtained with such deodorants wears off rather rapidly as the microflora soon recover their numbers. A criticism of many deodorant actives is that they indiscriminately affect all populations of microorganism resident on the surface of the skin. This mechanism of controlling body odour may be effective, for a limited period of time, but is thought to be medically undesirable as the skin' s natural microflora is often considered the first barrier against disease.
  • WO 87/06827 (Robertet SA) describes inhibitors of esterase- producing microorganisms. It is suggested that deodorant compositions may comprise such inhibitors as deodorising actives .
  • EP-A1-0 750 903 (Co ⁇ peratie Cosun UA) describes compositions comprising sugar-fatty acid esters which are said to be specific against lipophilic diphtheroids . This reference discloses that this group of microorganisms is responsible for body malodour.
  • VFAs volatile fatty acids
  • compositions comprising actives which are capable of reducing or preventing malodour by increasing the numbers of a particular population of deodorising microorganisms naturally occurring on the surface of the skin have not been found in the prior art .
  • the invention relates to a composition
  • a composition comprising an active capable of selectively increasing the population of naturally occurring deodorising microorganisms on the surface of the skin.
  • Naturally occurring deodorising microorganisms are members of the cutaneous microflora which are capable of degrading odoriferous molecules.
  • degrading is meant that the odoriferous molecules are transformed, by the deodorising microorganisms, to molecules which have either no odour, a reduced malodour or a preferred odour.
  • naturally occurring deodorising microorganisms include members of the Micrococcus and Brevibacterium genera.
  • selectively increasing is meant that the active is capable of increasing the population of deodorising microorganisms while not, or substantially not, affecting the population of non-deodorising microorganisms.
  • Non-deodorising microorganisms includes all other members of the cutaneous microflora.
  • Lysozyme is a glycosidase enzyme which degrades certain bacterial cell walls and is found on the surface of the skin.
  • We have surprisingly found that the population of naturally occurring deodorising microorganisms on the surface of the skin may be increased by inactivating or reducing lysozyme activity. This may be done by contacting lysozyme with antibodies or antibody fragments; using lysozyme substrate analogues; adjusting local pH; and distorting the structure of the enzyme, e.g. with detergents.
  • Such lysozyme substrate analogues include oligomers of N- acetyl glucosamine comprising at least one residue, chitin, chitosan and derivatives thereof.
  • Detergents are preferred actives according to the invention.
  • anionic detergents and especially alkali metal alkyl sulphate based anionic detergents, where the alkyl group contains from 10 to 20 carbon atoms e.g. Sodium dodecyl sulphate (SDS) and sodium tetradecyl sulphate.
  • actives according to the invention include phytic acid, n-pentane and bile acids, in particular conjugated bile acids, e.g. glycocholic acid.
  • the invention also provides a composition comprising an active capable of selectively increasing the population of naturally occurring deodorising microorganisms on the surface of the skin characterised in that the active is an inhibitor of lysozyme.
  • actives according to the invention do not include perfume components.
  • perfume component is meant an ingredient which is added to a perfume to contribute to the olfactory properties of the perfume .
  • perfume By perfume is meant a mixture of perfume components, and optionally a suitable diluent, which is added to a product to provide it with a pleasing fragrance.
  • composition according to the invention can take the form of a product suited to or adapted for topical application to human skin, in particular the underarm, e.g. a deodorant or antiperspirant, as well as a composition applied to the human skin more generally, e.g. shampoos, conditioners, skin cleansers, detergents, hair conditioners, sunscreens, sun tan lotions, skin conditioners, etc. It is to be understood that this list is not exhaustive with regard to suitable products comprising active agents according to the invention.
  • the active may be present in an amount of from 0.01 to 4% by weight of the composition, preferably from 0.01 to 2% and more preferably from 0.01 to 1%.
  • composition according to the invention may also comprise an antiperspirant active or an additional deodorising active, examples of which are common in the art.
  • ingredients which can optionally be present in the composition will depend on the formulation type. Typical formulation types include roll-on, aerosol, stick, cream, gel, powder, pump, etc. and are all common in the art. Examples of such optional ingredients according to the invention include:
  • emollients such as volatile silicones, non-volatile silicones, hydrocarbons or mineral oils, at e.g. 0 to 95%.
  • Volatile silicones often comprise polydimethylsiloxanes or polycyclodimethylsiloxanes containing from 3 to 8 silicons and especially 4, 5 and/or 6 silicons.
  • Non-volatile silicones include polydimethylsiloxane having -a viscosity in excess of 5 for example, from 50 to 1000 mm 2 s "1 , such as DOW CORNING 200 Fluids (standard viscosities 50-1000 mmV 1 ) .
  • emollients include PEG 400 distearate, and ethylene oxide and/or propylene oxide condensation products having the following formula:
  • R is either hydrogen or a hydrocarbon chain having from about 2 to 20 carbon atoms, and a and b are each from about 0 to 35 and a + b is from about 5 to 35.
  • emollient is Fluid AP, a condensate of about 14 moles of propylene acid with about 1 mole of butyl alcohol sold by Union Carbide .
  • compositions according to the invention in the form of a stick include fatty acid and fatty alcohol esters and water insoluble ethers .
  • -thickeners such as clays, for example Bentone 38; and silica, for example Aerosil 200;
  • -skin feel improvers such as talc and finely divided polyethylene, an example of which is ACUMIST B18;
  • -cosmetically acceptable vehicles such as anhydrous ethanol and other emollients, e.g. 0 to 95%;
  • Aerosol formulations contain a propellant, which commonly is a volatile hydrocarbon, usually boiling at -45 to 5°C such as propane, cyclopropane and/or butane, or ether such as dimethylether.
  • a propellant commonly is a volatile hydrocarbon, usually boiling at -45 to 5°C such as propane, cyclopropane and/or butane, or ether such as dimethylether.
  • ingredients which can optionally be present in the composition can conveniently form the balance of the composition.

Abstract

Composition comprising an active capable of selectively increasing the population of naturally occurring deodorising microorganisms on the surface of the skin.

Description

COSMETIC COMPOSITION
This invention relates to deodorant or antiperspirant compositions. In particular, it relates to compositions comprising an active capable of selectively increasing the population of naturally occurring deodorising microorganisms on the surface of the skin. The invention also relates to a method of reducing or preventing body malodour by applying to the surface of the skin a composition comprising said active.
Typically, a deodorising composition will attempt to significantly reduce or prevent body odour by reducing either perspiration or the number of microorganisms on the surface of the skin. The former is usually referred to as an antiperspirant composition and the latter a deodorant.
Compositions reducing perspiration often comprise a metal salt, such as aluminium or zirconium salt which blocks the sweat pores. This method is very simple yet a perspiration reduction of more than 50% is rarely achieved.
Deodorants, on the other hand, reduce the numbers of microorganisms on the surface of the skin. It is well known that sweat is odourless until it has been degraded by the skin microflora. Typical deodorants include ethanol and triclosan (2,4,4' -trichloro, 2 ' -hydroxy-diphenyl ether) which is a well known antimicrobial agent. However, the deodorising effect obtained with such deodorants wears off rather rapidly as the microflora soon recover their numbers. A criticism of many deodorant actives is that they indiscriminately affect all populations of microorganism resident on the surface of the skin. This mechanism of controlling body odour may be effective, for a limited period of time, but is thought to be medically undesirable as the skin' s natural microflora is often considered the first barrier against disease.
WO 87/06827 (Robertet SA) describes inhibitors of esterase- producing microorganisms. It is suggested that deodorant compositions may comprise such inhibitors as deodorising actives .
EP-A1-0 750 903 (Coόperatie Cosun UA) describes compositions comprising sugar-fatty acid esters which are said to be specific against lipophilic diphtheroids . This reference discloses that this group of microorganisms is responsible for body malodour.
It is well known that volatile fatty acids (VFAs) play a major role in malodour perception. GB 1 517 042 (Personal Products Company) describes deodorant compositions comprising particular actives for reducing malodour by sub- lethally inhibiting fatty acid formation by CoryπeJbacterium species.
Whereas these prior proposals are mainly concerned with inhibiting the growth of malodour producing microorganisms, the present invention is, on the contrary, concerned with increasing the growth of malodour-reducing microorganisms. References to compositions comprising actives which are capable of reducing or preventing malodour by increasing the numbers of a particular population of deodorising microorganisms naturally occurring on the surface of the skin have not been found in the prior art .
Accordingly, the invention relates to a composition comprising an active capable of selectively increasing the population of naturally occurring deodorising microorganisms on the surface of the skin.
Naturally occurring deodorising microorganisms are members of the cutaneous microflora which are capable of degrading odoriferous molecules. By degrading is meant that the odoriferous molecules are transformed, by the deodorising microorganisms, to molecules which have either no odour, a reduced malodour or a preferred odour. In particular, naturally occurring deodorising microorganisms include members of the Micrococcus and Brevibacterium genera.
By selectively increasing is meant that the active is capable of increasing the population of deodorising microorganisms while not, or substantially not, affecting the population of non-deodorising microorganisms.
Non-deodorising microorganisms includes all other members of the cutaneous microflora.
Lysozyme is a glycosidase enzyme which degrades certain bacterial cell walls and is found on the surface of the skin. We have surprisingly found that the population of naturally occurring deodorising microorganisms on the surface of the skin may be increased by inactivating or reducing lysozyme activity. This may be done by contacting lysozyme with antibodies or antibody fragments; using lysozyme substrate analogues; adjusting local pH; and distorting the structure of the enzyme, e.g. with detergents.
Such lysozyme substrate analogues include oligomers of N- acetyl glucosamine comprising at least one residue, chitin, chitosan and derivatives thereof.
Detergents are preferred actives according to the invention. In particular, anionic detergents and especially alkali metal alkyl sulphate based anionic detergents, where the alkyl group contains from 10 to 20 carbon atoms, e.g. Sodium dodecyl sulphate (SDS) and sodium tetradecyl sulphate.
Other actives according to the invention include phytic acid, n-pentane and bile acids, in particular conjugated bile acids, e.g. glycocholic acid.
Accordingly the invention also provides a composition comprising an active capable of selectively increasing the population of naturally occurring deodorising microorganisms on the surface of the skin characterised in that the active is an inhibitor of lysozyme.
It should be noted that actives according to the invention do not include perfume components. By perfume component is meant an ingredient which is added to a perfume to contribute to the olfactory properties of the perfume .
By perfume is meant a mixture of perfume components, and optionally a suitable diluent, which is added to a product to provide it with a pleasing fragrance.
The composition according to the invention can take the form of a product suited to or adapted for topical application to human skin, in particular the underarm, e.g. a deodorant or antiperspirant, as well as a composition applied to the human skin more generally, e.g. shampoos, conditioners, skin cleansers, detergents, hair conditioners, sunscreens, sun tan lotions, skin conditioners, etc. It is to be understood that this list is not exhaustive with regard to suitable products comprising active agents according to the invention.
The active may be present in an amount of from 0.01 to 4% by weight of the composition, preferably from 0.01 to 2% and more preferably from 0.01 to 1%.
A composition according to the invention may also comprise an antiperspirant active or an additional deodorising active, examples of which are common in the art.
Other ingredients which can optionally be present in the composition will depend on the formulation type. Typical formulation types include roll-on, aerosol, stick, cream, gel, powder, pump, etc. and are all common in the art. Examples of such optional ingredients according to the invention include:
-carriers and emollients, such as volatile silicones, non-volatile silicones, hydrocarbons or mineral oils, at e.g. 0 to 95%.
Volatile silicones often comprise polydimethylsiloxanes or polycyclodimethylsiloxanes containing from 3 to 8 silicons and especially 4, 5 and/or 6 silicons. Non-volatile silicones include polydimethylsiloxane having -a viscosity in excess of 5
Figure imgf000008_0001
for example, from 50 to 1000 mm2s"1, such as DOW CORNING 200 Fluids (standard viscosities 50-1000 mmV1) .
Other useful emollients include PEG 400 distearate, and ethylene oxide and/or propylene oxide condensation products having the following formula:
RO(C2H40)a(C3H60)bH
where R is either hydrogen or a hydrocarbon chain having from about 2 to 20 carbon atoms, and a and b are each from about 0 to 35 and a + b is from about 5 to 35. One example of such an emollient is Fluid AP, a condensate of about 14 moles of propylene acid with about 1 mole of butyl alcohol sold by Union Carbide .
Still further emollients suitable for use in compositions according to the invention in the form of a stick include fatty acid and fatty alcohol esters and water insoluble ethers .
-thickeners, such as clays, for example Bentone 38; and silica, for example Aerosil 200;
-skin feel improvers, such as talc and finely divided polyethylene, an example of which is ACUMIST B18;
-cosmetically acceptable vehicles, such as anhydrous ethanol and other emollients, e.g. 0 to 95%;
-perfumes;
-preservatives; and
-other cosmetic adjuncts conventionally employed in stick deodorant or antiperspirant products.
Aerosol formulations contain a propellant, which commonly is a volatile hydrocarbon, usually boiling at -45 to 5°C such as propane, cyclopropane and/or butane, or ether such as dimethylether.
The ingredients which can optionally be present in the composition, such as the ingredients mentioned hereinabove, can conveniently form the balance of the composition.

Claims

EXAMPLE 1The ability of selected actives to increase the deodorizing members of the axillary microflora is presented below.The model system for malodour generation employed is the in vi tro reproduction of fatty acid catabolism and volatile fatty acid (VFA) generation. The method consisted of 250 ml baffled shake flasks, to which were added 30 ml semi- synthetic medium supplemented with 2.0 mg/ml pentadecanoic acid (see below) and, where specified, lysozyme at 5 mg/1. Flasks were inoculated with microbial biomass (mixed cultures of CoryπeJbacteriu-ri sp. (NCIMB 40928) and Micrococcus luteus (NCIMB 40927) , individually pre-grown in TSBT (see below) for 24 h) to give starting optical densities (A590) of 3.0-4.0. The flasks were then incubated aerobically at 35°C, with agitation (130 rpm) , and analysed after 24 h. Upon completion of each experiment, culture viability and purity were qualitatively determined by streaking 1.0 μl culture medium onto TSAT plates (see below) . Fatty acids, including VFAs, were determined by capillary gas chromatography (GC) (see below) .Fatty acid/VFA levels in the flasks were determined by capillary GC analysis. Initially, 5.0 ml aliquots from each flask were rapidly transferred into universal tubes; an internal standard (1.0 mg/ml lauric acid) was added to each universal and the culture medium was acidified (pH ~2) by the addition of hydrochloric acid. Liquid-liquid extraction was then carried out using 2 vol (10 ml) ethyl acetate; organic and aqueous phases were resolved by centrifugation (2000 rpm, 3 min) . 2.0 ml of each organic (upper) phase was then transferred to a sampling tube prior to analysis on a Perkin Elmer 8000 (Series 2) GC fitted with a 15 m x 0.32 mm (internal diameter) FFAP (nitroterephalic acid modified PEG/siloxane copolymer) fused silica capillary column (film thickness 0.25 μm) (Quadrex) . This column was attached to the split-splitless injector and flame ionisation detector (FID) of the GC; injector and detector temperatures were each 300°C. Carrier gas for the column was helium (6.0 psi) , while hydrogen (17 psi) and air (23 psi) supplied the FID. The temperature programme for fatty acid analysis was 80°C (2 min) ; 80-250°C (20°C/min) ; 250°C (5 min) . Sample size for injection was 0.5-1.0 μl . Fatty acid levels in the flasks were quantified by comparison of peak areas with known levels of both internal (lauric acid) and externally run (pentadecanoic and propionic acids) standards.Prior to inoculation, flasks were supplemented with selected materials (eg. SDS) , at a range of concentrations, to determine their ability to inhibit lysozyme activity and allow naturally deodorising micrococci to proliferate. Stock active solutions were prepared in semi-synthetic medium (see below) . At the end of each experiment, culture viabilities and fatty acid/VFA levels in the experimental flasks were compared to those in control flasks.Composition of Tween-supplemented Tryptone soya broth/agar (TSBT, TSAT) used for growth/maintenance of axillary bacteria (g/1) : Tryptone soya broth (30.0) (Merck), Yeast extract (10.0) (Beta Lab), Tween 80 (1.0) (Tween is a trade mark ICI Speciality Chemicals), + Agar (20.0) . Composition of semi-synthetic medium used in laboratory systems simulating fatty acid catabolism and VFA generation by axillary bacteria (mg/ml): KH2P04 (1.6), (NH4)2HP04 (5.0), Na2S04 (0.38), Yeast Nitrogen Base (Difco) (3.35), Yeast Extract (0.5), Tween 80 (0.2), Triton X-100 (trademark of Union Carbide) (0.2), MgCl2.6H20 (0.5), Pentadecanoic acid (2.0) .The effect of the lysozyme inhibitor SDS on viability and VFA levels, after 24 h incubation, in in vi tro biotransformation model systems supplemented with pentadecanoic acid (2.0 g/1) and inoculated with Corynejbacteritun and Micrococcus spp. is presented in Table 1. Initial biomass levels in each assay were identical. TABLE 1Viability assessment :+++, confluent growth; ++, semi-confluent growth; +, single colonies ; - , no growthCulture system A:CoryneJacterium sp. (NCIMB 40928) + Micrococcus luteus(NCIMB 40927)Culture system B:(NCIMB 40928) + (NCIMB 40927)+ Lysozyme (5 mg/1)Culture system C:(NCIMB 40928) + (NCIMB 40927)+ Lysozyme (5 mg/1) + SDS (0.1 g/i)Culture system D: (NCIMB 40928) + (NCIMB 40927)+ Lysozyme (5 mg/1) + SDS (0.2 g/i)In culture system A, pentadecanoic acid was fully degraded to C02/H20, due to the efficient removal, by M. luteus, of both the substrate and any VFA product generated by the CoryneJbacterium species. The presence of lysozyme in system B caused micrococcal lysis and conversion of the substrate to propionic acid, due to corynebacterial metabolism. Thus is demonstrated both the natural VFA-deodorising properties of micrococci and the detrimental effect lysozyme has on this process. SDS, at 0.1 mg/ml, inhibited lysozyme insufficiently to affect net VFA levels; however, at 0.2 mg/ml SDS, micrococcal lysis was curbed enough to reduce net VFA generation by >80%. This demonstrates the ability of lysozyme inhibitors to significantly reduce net VFA levels in vi tro by increasing micrococcal numbers and exploiting the natural deodorising properties of these bacteria.EXAMPLE 2The following is a typical formulation which comprises an active according to the invention.It is made by methods common in the art . CLAIMS ;
1. Composition comprising an active capable of selectively increasing the population of naturally occurring deodorising microorganisms on the surface of the skin.
2. Composition according to claim 1 wherein the naturally occurring deodorising microorganisms are members of the Micrococcus genus.
3. Composition according to claim 1 wherein the naturally occurring deodorising microorganisms are members of the BreviJbacterium genus.
4. Composition comprising an active according to claim 1 characterised in that the active is an inhibitor of lysozyme.
5. Composition according to claim 4, characterised in that the active is an alkali metal alkyl sulphate based anionic detergent where the alkyl group contains from 10 to 20 carbon atoms.
6. Method of reducing or preventing malodour by applying to the surface of the skin a composition according to any preceding claim.
PCT/GB1999/002143 1998-07-07 1999-07-05 Cosmetic composition WO2000001354A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU46360/99A AU4636099A (en) 1998-07-07 1999-07-05 Cosmetic composition

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GBGB9814734.1A GB9814734D0 (en) 1998-07-07 1998-07-07 Cosmetic composition
GB9814734.1 1998-07-07

Publications (1)

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WO2000001354A1 true WO2000001354A1 (en) 2000-01-13

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AR (1) AR019340A1 (en)
AU (1) AU4636099A (en)
CO (1) CO5070577A1 (en)
GB (1) GB9814734D0 (en)
WO (1) WO2000001354A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9228284B2 (en) 2011-02-15 2016-01-05 Novozymes North America, Inc. Mitigation of odor in cleaning machines and cleaning processes

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0650720A1 (en) * 1993-10-28 1995-05-03 Sanwa Kagaku Kenkyusho Co., Ltd. Skin care and deodorant compositions
EP0591443B1 (en) * 1991-06-27 1996-10-23 Bioeurope Use of cosmetic compositions containing oligosaccharides
EP0750903A1 (en) * 1995-06-28 1997-01-02 Coöperatie Cosun U.A. Deodorant composition

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0591443B1 (en) * 1991-06-27 1996-10-23 Bioeurope Use of cosmetic compositions containing oligosaccharides
EP0650720A1 (en) * 1993-10-28 1995-05-03 Sanwa Kagaku Kenkyusho Co., Ltd. Skin care and deodorant compositions
EP0750903A1 (en) * 1995-06-28 1997-01-02 Coöperatie Cosun U.A. Deodorant composition

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9228284B2 (en) 2011-02-15 2016-01-05 Novozymes North America, Inc. Mitigation of odor in cleaning machines and cleaning processes
US9404208B2 (en) 2011-02-15 2016-08-02 Novozymes Biologicals, Inc. Mitigation of odor in cleaning machines and cleaning processes
US9982382B2 (en) 2011-02-15 2018-05-29 Novozymes Biologicals, Inc. Mitigation of odor in cleaning machines and cleaning processes
US10577738B2 (en) 2011-02-15 2020-03-03 Novozymes Biologicals, Inc. Mitigation of odor in cleaning machines and cleaning processes
US10968556B2 (en) 2011-02-15 2021-04-06 Novozymes Biologicals, Inc. Mitigation of odor in cleaning machines and cleaning processes

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AU4636099A (en) 2000-01-24
CO5070577A1 (en) 2001-08-28
AR019340A1 (en) 2002-02-13

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