WO2015091294A1 - Compositions à base d'un monorhamnolipide - Google Patents

Compositions à base d'un monorhamnolipide Download PDF

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Publication number
WO2015091294A1
WO2015091294A1 PCT/EP2014/077650 EP2014077650W WO2015091294A1 WO 2015091294 A1 WO2015091294 A1 WO 2015091294A1 EP 2014077650 W EP2014077650 W EP 2014077650W WO 2015091294 A1 WO2015091294 A1 WO 2015091294A1
Authority
WO
WIPO (PCT)
Prior art keywords
rhamnolipid
mono
rha
composition according
rhamnolipids
Prior art date
Application number
PCT/EP2014/077650
Other languages
English (en)
Inventor
Mayri Alejandra DIAZ DE RIENZO
Paul Simon Stevenson
Original Assignee
Unilever Plc
Unilever N.V.
Conopco, Inc., D/B/A Unilever
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 N.V., Conopco, Inc., D/B/A Unilever filed Critical Unilever Plc
Publication of WO2015091294A1 publication Critical patent/WO2015091294A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/005—Antimicrobial preparations
    • 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
    • A61K8/60—Sugars; Derivatives thereof
    • 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
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/12—Preparations containing hair conditioners
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/04—Carboxylic acids or salts thereof
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions

Definitions

  • the present invention relates to an improved bacteriostatic composition
  • CN103215207A discloses bacteriostatic rhamnolipid. Despite the prior art there remains a need for improved bacteriostatic rhamnolipid compositions.
  • the present invention provides a bacteriostatic composition
  • a rhamnolipid comprising at least 50 wt % of mono-rhamnolipid.
  • Mono-rhamnolipids have a single rhamnose sugar ring.
  • the lUPAC Name is 3-[3-
  • rhamnolipids throughout this patent specification, the prefixes mono- and di- are used to indicate respectively mono-rhamnolipids (having a single rhamnose sugar ring) and di-rhamnolipids (having two rhamnose sugar rings). If abbreviations are used R1 is mono-rhamnolipid and R2 is di- rhamnolipid.
  • the mono-rhamnolipid may be L-rhamnosyl- -hydroxydecanoyl- - hydroxydecanoate (RhaC-ioC-io with a formula of C26H 4 8Og) produced by P.
  • a typical di-rhamnolipid is L-rhamnosyl-L-rhamnosyl- -hydroxydecanoyl- - hydroxydecanoate (Rha2CioCio with a formula of C32H58O13).
  • rhamnolipids are sources of mono- and di- rhamnolipids
  • C12:1 , C14:1 indicates fatty acyl chains with double bonds - Rhamnolipids produced by P. aeruginosa (mono-rhamnolipids):
  • Rha-Cs-C-io Rha-C-io, Rha-C-io-Ce, Rha-C-io-C- ⁇ , Rha-C-io-C-12, Rha-Cio-Ci2:i j Rha- C12-C10, Rha-Ci2:i-Cio
  • Rha-C-io-Ce Rha-Cio"CiOi Rha- C"i2:i"C"i2j Rha-C"i 4 -C"i0i Rha-Ci 4: i-Cio.
  • Mono-rhamnolipids may also be produced from P.putida by introduction of genes rhIA and rhIB from Psuedomonas aeruginosa [Cha et al. in Bioresour Technol. 2008. 99(7):2192-9 ]
  • Rha-Rha-Cio-Ci2 i , Rha-Rha-Ci 0 -Ci 2 , Rha-Rha-Ci 2 -Ci 0 , Rha-Rha-Ci 2: i- C"i2i Rha-Rha-Cio"Ci 4: i - Rhamnolipids produced by Burkholdera pseudomallei (di-rhamnolipids only):
  • Rha-Rha-C 4 -C 4 Rha-Rha-C 4 -C 4 .
  • the rhamnolipid comprises at least 50 wt % mono-rhamnolipid, more preferably 60 wt %, even more preferably 75 wt % and most preferably at least 90 wt % mono-rhamnolipid.
  • composition according to the invention can be used as bacteriostatic raw material such that the user e.g. consumer dilutes in a further composition or the composition may be a consumer product the application of which is intended to provide bacteriostatic effect to a substrate or even as a preservative within the consumer composition.
  • composition may comprise further surfactants.
  • each further surfactant comprises a synthetic anionic surfactant.
  • 'Anionic surfactants' are defined herein as amphiphilic molecules comprising one or more functional groups that exhibit a net anionic charge when in aqueous solution at the normal wash pH of between 4 and 1 1 .
  • the alkali metal salts of organic sulphur reaction products having in their molecular structure an alkyl moiety containing from about 6 to 24 carbon atoms, more greater than 12 carbon atoms and preferably also a moiety selected from the group consisting of sulphonic and sulphuric acid ester moieties.
  • the anionic surfactant preferably has low levels of ethoxylation, preferably comprising 1 -12 ethylene oxide units per molecule, more preferably 1 -3 and even more preferably 1 .
  • the units of ethylene oxide may be an average.
  • any anionic surfactant hereinafter described can be used, such as primary alkyl sulphates (PAS) e.g. sodium lauryl sulphate (SLS) and e.g. alkyl ether sulphate such as sodium lauryl ether sulphate(SLES), soaps, fatty acid ester sulphonates, fatty acid sulphates or sulphonates; alkyl benzene sulphonates (LAS), sulphosuccinate esters, olefin sulphonates, paraffin sulphonates and organic phosphates; fatty alcohol sulphates; alkyl phenol ether sulphate; fatty acyl isethionate products which products comprise fatty acyl isethionate and free fatty acid and/or fatty acid salt; alkyl sulphonates such as sodium alkane sulphonate.
  • PES primary alkyl sulphates
  • SLS sodium lauryl sulph
  • Preferred anionic surfactants are the alkali (ammonium or triethylammonium for example) and alkaline earth metal salts of the above.
  • the source oil / alcohol can be plant or animal derived for example coconut or palm or tallow etc.
  • the further surfactant may also comprise a non-ionic, cationic and/or amphoteric and mixtures thereof.
  • the rhamnolipid is present at 1 wt % - 95 wt % of the total surfactant (rhamnolipid and further surfactant) in the composition. More preferably the rhamnolipid is present at 10 - 70 wt % of the total surfactant.
  • the further surfactant is present in the fabric or hard surface washing compositions at a level of from 3 to 85% by weight, preferably from 3 to 60% by weight, more preferably from 3 to 40% by weight, most preferably from 3 to 35% by weight.
  • the further surfactant is present in personal (human skin and hair) wash compositions at a level of 5 to 60%, preferably 10 to 40% surfactant, while cosmetic compositions need not comprise any surfactant, but preferably comprise 1 % to 30% by wt., more preferably 1 to 15% by wt. surfactant.
  • the composition is a home care and personal product.
  • Preferred home care products include laundry detergent/cleaning compositions, laundry conditioning compositions, and hard surface cleaners such as hand and machine dish washing compositions, kitchen and bathroom cleaners.
  • Hard surfaces include kitchen and bathroom surfaces, cutlery, crockery etc.
  • Personal care compositions include shampoos, hair conditioners, deodorants, skin cleansing compositions and oral care products such as toothpastes and mouthwashes.
  • P. aeruginosa ATCC 15442 and Staphylococcus aureus ATCC 9144 were maintained in nutrient broth plus 20% glycerol at -20°C.
  • Bacterial growth from a nutrient agar slant incubated for 24h at 30°C was used to obtain a bacterial suspension with an optical density at 570nm adjusted to give 108 cfu/mL.
  • Rhamnolipid containing 10% (w/v) mono-rhamnolipid (C26H 4 8O9, MW: 504, Critical Micelle Concentration: 20 mg/L M at neutral pH) and 10% (w/v) dirhamnolipid (C 3 2H58O 3 , MW: 650, CMC: 1 .5x10-4 30 mg/L at neutral pH) was obtained separated from a sample obtained from Jeneil Biosurfactant Co. (Saukville, Wisconsin).
  • the Mono- and di-rhamnolipid was separated from the sample obtained from Jeneil using the protocol below and the individual R1/ R2 fractions obtained were used to produce the 10% rhamnolipid solution mentioned above
  • JBR425 A quantified amount of JBR425 was acidified to pH 3 using 12M HCI and placed in a refrigerator overnight. The supernatant was then extracted three times using a 2:1 mixture of Chloroform and Ethanol. The solvent was then removed by rotary evaporation and the isolated rhamnolipid mixture was then re-dissolved in methanol.
  • the process of separating and characterising the mixture was carried out using an HPLC connected to an Ion Trap Electrospray ionisation Mass Spectrometer.
  • the mode of ionisation was in negative mode with a scanning range of 50-1200Da.
  • the column used to separate was a Phenomenex luna C18 250 x 4.6mm 5 ⁇ column.
  • the mobile phase water (mobile phase A) and acetonitrile (mobile phase B) were used to separate via a gradient of 60:40 (A:B) changing to 30:70 (A:B) over 30 minutes.
  • the system was then held for 5 minutes before returning to the start conditions all at a flow rate of 0.5ml/min.
  • the injection volume was 10 ⁇ .
  • P. aeruginosa ATCC 15442 was grown overnight as previously described and diluted 100-fold with TSB 50% following which a 100 ⁇ _ sample of each diluted culture was dispensed (eight replicates) to fill a 96 well Oxoplate OP96C®. After 48h each well was rinsed twice with PBS 1 XS, and the active different treatments were added to each well during 30min at 30°C.
  • OxoPlate OP96C (PreSens, Regensburg, Germany) contains oxygen-sensitive particles PSLi-Pt-1 (Opto- Sense, Worth, Germany), which consist of small polystyrene particles.
  • the sensor has a thickness of about 10 ⁇ and is fixed at the bottom of each well of a 96-flat bottom-well plate (Greiner, Frickenhausen, Germany). The oxygen concentration in each well was followed for 21 h at 20min intervals. Fluorescence of each well was measured in dual kinetic mode (BMG Labtech GmbH, Germany). Filter pair 1 (544/650 nm) detects fluorescence of the indicator dye. The second filter pair (544/590 nm) measures fluorescence of the reference dye. All experiments were repeated on independent days. Oxygen concentration as percentage air saturation was calculated for each well by using the following equation:
  • Biofilms of Pseudomonas aeruginosa ATCC 15442 were formed on an Oxoplate® after 48h at 30°C, once the biofilms were rinsed with PBS 1 X twice they were incubated for half an hour under different treatments as follows:
  • KH 2 PO - (0.24gpl) final concentration at 1X 1 .8mM
  • PBS 1 X dissolve the reagents listed above in 800 ml_ of H 2 O. Adjust the pH to 7.4 with HCI, and then add H 2 O to 1 L. Dispense the solution into aliquots and sterilize them by autoclaving for 20 min at 15 psi (1 .05 kg/cm 2 ) on liquid cycle.
  • Mono-Rhamnolipids 0.04% were produced by dilution of R1 (mono - rhamnolipid) Stock solution.
  • Di-Rhamnolipids 0.04% were produced by dilution of R2 (Di rhamnolipid) stock solution.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • Dermatology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne une composition bactériostatique comprenant un rhamnolipide, ce rhamnolipide comprenant au moins 50 % en poids d'un monorhamnolipide.
PCT/EP2014/077650 2013-12-18 2014-12-12 Compositions à base d'un monorhamnolipide WO2015091294A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP13198100.3 2013-12-18
EP13198100 2013-12-18

Publications (1)

Publication Number Publication Date
WO2015091294A1 true WO2015091294A1 (fr) 2015-06-25

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9884883B2 (en) 2015-01-12 2018-02-06 Logos Technologies, Llc Production of rhamnolipid compositions
WO2018195613A1 (fr) 2017-04-28 2018-11-01 L'oreal Composition de déodorant
CN109289499A (zh) * 2018-11-02 2019-02-01 广州三环保有限公司 生物除臭剂的配方及生物除臭剂的制作方法
WO2019154970A1 (fr) * 2018-02-09 2019-08-15 Evonik Degussa Gmbh Composition de mélange comprenant des glucolipides
US10829507B2 (en) 2017-02-06 2020-11-10 Stepan Company Decolorization of concentrated rhamnolipid composition
EP4155371A1 (fr) 2022-08-29 2023-03-29 Evonik Operations GmbH Composition riche en mono-rhamnolipides
WO2023099346A1 (fr) * 2021-12-02 2023-06-08 Evonik Operations Gmbh Composition comprenant des glucolipides
US11993803B2 (en) 2018-02-09 2024-05-28 Evonik Operations Gmbh Mixture composition comprising glucolipids

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008013899A2 (fr) * 2006-07-27 2008-01-31 Aurora Advance Beauty Labs Formulations à base de rhamnolipides
WO2012010406A1 (fr) * 2010-07-22 2012-01-26 Unilever Plc Combinaisons de rhamnolipides et d'enzymes pour nettoyage amélioré
CN103215207A (zh) * 2013-04-18 2013-07-24 中国科学院微生物研究所 一株适用于油藏环境的假单胞菌菌株及其应用

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008013899A2 (fr) * 2006-07-27 2008-01-31 Aurora Advance Beauty Labs Formulations à base de rhamnolipides
WO2012010406A1 (fr) * 2010-07-22 2012-01-26 Unilever Plc Combinaisons de rhamnolipides et d'enzymes pour nettoyage amélioré
CN103215207A (zh) * 2013-04-18 2013-07-24 中国科学院微生物研究所 一株适用于油藏环境的假单胞菌菌株及其应用

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
LIU Z F ET AL: "Effects of monorhamnolipid and Tween 80 on the degradation of phenol by Candida tropicalis", PROCESS BIOCHEMISTRY, ELSEVIER, NL, vol. 45, no. 5, 1 May 2010 (2010-05-01), pages 805 - 809, XP026991656, ISSN: 1359-5113, [retrieved on 20100125] *
W W CHRISTIE ET AL: "Rhamnolipids, sophorolipids and other glycolipid biosurfactants: structures, occurrence and biology RHAMNOLIPIDS, SOPHOROLIPIDS AND OTHER GLYCOLIPID BIOSURFACTANTS STRUCTURES, OCCURRENCE AND BIOLOGY", 1 July 2013 (2013-07-01), pages 1 - 7, XP055111253, Retrieved from the Internet <URL:http://lipidlibrary.aocs.org/Lipids/rhamno/file.pdf> [retrieved on 20140401] *

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9884883B2 (en) 2015-01-12 2018-02-06 Logos Technologies, Llc Production of rhamnolipid compositions
US10829507B2 (en) 2017-02-06 2020-11-10 Stepan Company Decolorization of concentrated rhamnolipid composition
WO2018195613A1 (fr) 2017-04-28 2018-11-01 L'oreal Composition de déodorant
WO2019154970A1 (fr) * 2018-02-09 2019-08-15 Evonik Degussa Gmbh Composition de mélange comprenant des glucolipides
US11993803B2 (en) 2018-02-09 2024-05-28 Evonik Operations Gmbh Mixture composition comprising glucolipids
CN109289499A (zh) * 2018-11-02 2019-02-01 广州三环保有限公司 生物除臭剂的配方及生物除臭剂的制作方法
WO2023099346A1 (fr) * 2021-12-02 2023-06-08 Evonik Operations Gmbh Composition comprenant des glucolipides
EP4155371A1 (fr) 2022-08-29 2023-03-29 Evonik Operations GmbH Composition riche en mono-rhamnolipides

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