WO2014000982A1 - Compositions de soin buccal - Google Patents

Compositions de soin buccal Download PDF

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Publication number
WO2014000982A1
WO2014000982A1 PCT/EP2013/060473 EP2013060473W WO2014000982A1 WO 2014000982 A1 WO2014000982 A1 WO 2014000982A1 EP 2013060473 W EP2013060473 W EP 2013060473W WO 2014000982 A1 WO2014000982 A1 WO 2014000982A1
Authority
WO
WIPO (PCT)
Prior art keywords
total weight
oral care
fatty acyl
care composition
acyl isethionate
Prior art date
Application number
PCT/EP2013/060473
Other languages
English (en)
Inventor
Kavssery Parameswaran Ananthapadmanabhan
Caroline Alexandra Hall
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 WO2014000982A1 publication Critical patent/WO2014000982A1/fr

Links

Classifications

    • 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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/25—Silicon; Compounds thereof
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/345—Alcohols containing more than one hydroxy group
    • 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A61K8/442—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof substituted by amido group(s)
    • 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
    • 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
    • A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • 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
    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/28—Rubbing or scrubbing compositions; Peeling or abrasive compositions; Containing exfoliants

Definitions

  • the present invention relates to oral care compositions. More particularly the invention relates to oral care compositions which comprise fatty acyl isethionate.
  • Foam is a desirable characteristic of oral care compositions such as dentifrices, since it enables the dentifrice to spread throughout the oral cavity during brushing and contact tooth surfaces thoroughly.
  • Compositions with good foaming ability are also preferred by consumers since the foaming provides the perception that the composition is cleaning effectively.
  • SLS sodium lauryl sulphate
  • a typical dentifrice contains up to 2 or 3% of SLS (by weight based on total weight) for its foaming and surfactant action.
  • Anionic surface active agents such as SLS have been associated in some cases with mild adverse effects such as unpleasant flavour reactions when drinking or eating citrus shortly after tooth brushing. Accordingly, for consumers susceptible to these effects it would be desirable to reduce the content of anionic surface active agents such as SLS.
  • the present invention provides an oral care composition comprising:
  • fatty acyl isethionate product is defined as a mixture comprising: (i) from 40 to 80wt% (by weight based on the total weight of the fatty acyl isethionate product) of one or more fatty acyl isethionate salts having the general formula (I):
  • composition of the invention has a liquid continuous phase comprising water or polyhydric alcohol or a mixture thereof.
  • compositions of the invention are those which are suitable for brushing and/or rinsing the surfaces of the oral cavity.
  • the amount of water and/or polyhydric alcohol will generally be at least 10wt%, preferably at least 30wt%, more preferably at least 50wt% (by total weight water and/or polyhydric alcohol based on the total weight of the composition).
  • dentifrice An example of a preferred type of product form in the context of the present invention is a dentifrice.
  • the term "dentifrice” generally denotes formulations which are used to clean the surfaces of the oral cavity.
  • the dentifrice is an oral composition that is not intentionally swallowed for purposes of systemic
  • the dentifrice is used in conjunction with a cleaning implement such as a toothbrush, usually by applying it to the bristles of the toothbrush and then brushing the accessible surfaces of the oral cavity.
  • a cleaning implement such as a toothbrush
  • the dentifrice is in the form of a paste or a gel (or a combination thereof).
  • a dentifrice composition according to the invention will usually contain a liquid continuous phase in an amount of from 40 to 99wt% (by total weight liquid continuous phase based on the total weight of the dentifrice).
  • a liquid continuous phase will typically comprise a mixture of water and polyhydric alcohol in various relative amounts, with the amount of water generally ranging from 10 to 45wt% (by total weight water based on the total weight of the dentifrice) and the amount of polyhydric alcohol generally ranging from 30 to 70wt% (by total weight polyhydric based on the total weight of the dentifrice).
  • Typical polyhydric alcohols include humectants such as glycerol, sorbitol, polyethylene glycol, polypropylene glycol, propylene glycol, xylitol (and other edible polyhydric alcohols),
  • the composition of the invention comprises a particulate abrasive cleaning agent in an amount of from 3 to 75wt% (by total weight particulate abrasive cleaning agent based on the total weight of the oral care composition).
  • suitable particulate abrasive cleaning agents include silica xerogels, hydrogels and aerogels and precipitated particulate silicas; calcium carbonate, dicalcium phosphate, tricalcium phosphate, calcined alumina, sodium and potassium metaphosphate, sodium and potassium pyrophosphates, sodium trimetaphosphate, sodium hexametaphosphate, particulate hydroxyapatite and mixtures thereof.
  • the fatty acyl isethionate product as defined above may typically be prepared by the reaction of at least one fatty acid of formula R C(0)OH (in which R has the definition described above) with at least one hydroxyalkylsulfonic acid salt of the formula HOR 2 S03M (in which R 2 and M have the definitions described above).
  • Suitable fatty acids for use in the preparation of the fatty acyl isethionate product include those in which R is a linear or branched, saturated or unsaturated hydrocarbon radical having 5 to 21 carbon atoms. Such fatty acids may be naturally occurring or synthetic or a mixture thereof. Naturally occurring fatty acids are usually mixtures of acids having a hydrocarbon chain of varying length. For example, "coconut fatty acid” as used herein is a mixture containing a range of carboxylic acids in which the R carbon chain length ranges from about 7 to 17 carbon atoms, with some unsaturation which may be removed by hydrogenation.
  • hydrogenated coconut fatty acid is a mixture containing a range of carboxylic acids in which the R carbon chain length ranges from about 7 to 17 carbon atoms, mostly lauric and myristic acids, together with some capric and caprylic acids, and contains very little, if any, unsaturation.
  • Preferred fatty acids are those in which R is a linear or branched, saturated or unsaturated hydrocarbon radical having 7 to 17 carbon atoms.
  • Specific examples of preferred fatty acids include coconut fatty acid (R having 7 to 17 carbon atoms), hydrogenated coconut fatty acid (R having 7 to 17 carbon atoms), lauric acid (R having 1 1 carbon atoms), palmitic acid (R having 15 carbon atoms), palm kernel fatty acid (R having 7 to 17 carbon atoms), oleic acid (unsaturated R having 17 carbon atoms), stearic acid (saturated R having 17 carbon atoms), tallow fatty acid (partially unsaturated R mainly having 15 and 17 carbon atoms), and hydrogenated tallow fatty acid. Mixtures of any of the above described fatty acids may also be used.
  • Suitable hydroxyalkylsulfonic acid salts for use in the preparation of the fatty acyl isethionate product include those in which R 2 has the general formula (II):
  • hydroxyalkylsulfonic acid salts include
  • hydroxyethylsulfonic acid salts such as sodium hydroxyethylsulfonate.
  • Other specific examples of preferred hydroxyalkylsulfonic acid salts include alkyl- substituted hydroxyethylsulfonic acid salts such as the sodium salts of methyl and/or ethyl-substituted hydroxyethylsulfonic acid salts, for example sodium 1 - methyl 2-hydroxy ethane 1 -sulfonate, sodium 2-methyl, 2-hydroxy ethane 1 - sulfonate, sodium 1 -ethyl 2-hydroxy ethane 1 -sulfonate and sodium 2-ethyl, 2- hydroxy ethane 1 -sulfonate.
  • hydroxyalkylsulfonic acid salts may also be used.
  • the fatty acid and hydroxyalkylsulfonic acid salt are mixed and heated in the presence of a metal catalyst.
  • a metal catalyst Generally, an excess of fatty acid is used in order to shift the reaction equilibrium to fatty acyl isethionate synthesis.
  • the molar ratio of fatty acid to hydroxyalkylsulfonic acid salt may range from 1 .3:1 to 1 .1 :1 .
  • the resulting fatty acyl isethionate product is usually termed "directly esterified fatty isethionate" (or DEFI) and may be characterized as a mixture of 40 to 80wt% fatty acyl isethionate (formed from the reaction), 15 to 50wt% free fatty acids, in addition to unreacted hydroxyalkylsulfonic acid salt (generally at levels less than 5 wt%) and traces of other impurities (generally at levels less than 2 wt%).
  • DEFI directly esterified fatty isethionate
  • a preferred class of fatty acyl isethionate product for use in the present invention and obtainable by a direct esterification process such as that described above, comprises:
  • R C(0)OR 2 S0 3 M in which R is a linear or branched, saturated or unsaturated hydrocarbon radical having 7 to 17 carbon atoms, R 2 is -CH 2 CH 2 - or -CH(CH3)- CH 2 - , and M is a solubilising cation such as sodium;
  • the one or more fatty acyl isethionate salts (i) are selected from sodium cocoyl isethionate, sodium cocoyl methyl isethionate, sodium cocoyl ethyl isethionate and mixtures thereof.
  • the one or more fatty acids (ii) may be defined as a mixture (for example of coconut fatty acid and stearic acid and/or their corresponding sodium salts), in which the content of long chain material (typically C16 to ds) is at least 25wt% by weight based on the total weight of the fatty acids (b).
  • the total amount of fatty acyl isethionate product in compositions of the invention preferably ranges from 1 to 4wt%, more preferably from 1 .1 to 3.5wt% (by total weight fatty acyl isethionate product based on the total weight of the composition).
  • Amphoteric surfactant preferably ranges from 1 to 4wt%, more preferably from 1 .1 to 3.5wt% (by total weight fatty acyl isethionate product based on the total weight of the composition).
  • compositions according to the invention comprise from 0.1 to 2wt% (by weight based on the total weight of the oral care composition) of amphoteric surfactant.
  • amphoteric surfactants include alkyl amine oxides, alkyl betaines, alkyl amidopropyl betaines, alkyl sulphobetaines (sultaines), alkyl glycinates, alkyl carboxyglycinates, alkyl amphopropionates,
  • alkylamphoglycinates alkyl amidopropyl hydroxysultaines, acyl taurates and acyl glutamates.
  • the alkyl and acyl groups generally contain from 8 to 22 carbon atoms, may be straight or branched chain, and may be saturated or unsaturated.
  • a preferred class of amphoteric surfactants for use in the invention are alkyl amidopropyl betaines of general formula: R 5 -CO-NH-(CH 2 )3-N + (CH3)2-CH 2 COO- in which R 5 is a straight or branched chain alkyl group having 10 to 18, preferably 12 to 14 carbon atoms. Mixtures of any of the foregoing amphoteric surfactants may also be suitable.
  • the total amount of amphoteric surfactant in compositions of the invention preferably ranges from 0.3 to 1 .5%, more preferably from 0.4 to 1 .2% by weight based on the total weight of the composition.
  • the oral care composition of the invention comprises from 0 to 1 .5% alkyl sulfate anionic surfactant (by total weight alkyl sulfate anionic surfactant based on the total weight of the composition).
  • alkyl sulfate anionic surfactant is generally meant one or more Ce-ie alkyl sulfates and/or Ce-ie alkyl ether sulfates, such as those materials having the general formula:
  • Specific examples include sodium lauryl sulfate (SLS), sodium dodecyl sulfate (SDS), sodium lauryl ether sulfate (SLES) having an average degree of ethoxylation of from 0.5 to 3 (preferably 1 to 3) and mixtures thereof.
  • the total amount of alkyl sulfate anionic surfactant in compositions of the invention preferably ranges from 0 to 0.5%, more preferably from 0 to 0.25% by weight based on the total weight of the composition.
  • compositions according to the invention comprise:
  • an alkyl sulfate anionic surfactant which is sodium lauryl sulphate.
  • composition according to the invention will generally contain further ingredients to enhance performance and/or consumer acceptability.
  • a composition according to the invention which is formulated as a dentifrice will usually contain one or more thickening agents.
  • suitable thickening agents include carboxyvinyl polymers (such as polyacrylic acids cross-linked with polyallyl sucrose or polyallyl pentaerythritol), hydroxyethyl cellulose, hydroxypropyl cellulose, water soluble salts of cellulose ethers (such as sodium carboxymethyl cellulose and sodium carboxymethyl hydroxyethyl cellulose), natural gums (such as carrageenan, gum karaya, guar gum, xanthan gum, gum arabic, and gum tragacanth), finely divided silicas, hectorites, colloidal magnesium aluminium silicates and mixtures thereof.
  • carboxyvinyl polymers such as polyacrylic acids cross-linked with polyallyl sucrose or polyallyl pentaerythritol
  • hydroxyethyl cellulose hydroxypropyl cellulose
  • the one or more thickening agents will generally be present in sufficient quantities to ensure that the dentifrice is extrudable, retains its shape when squeezed from a tube onto a toothbrush, and will not fall between the bristles of the brush during normal consumer usage.
  • the total amount of such one or more thickening agents in compositions of the invention generally ranges from 0.1 to 15wt% (by total weight thickening agent based on the total weight of the composition).
  • the individual levels of such one or more thickening agents depends on the material chosen.
  • Polymeric thickening agents such as the carboxyvinyl polymers and natural gums described above
  • Inorganic thickening agents (such as the finely divided silicas described above) will generally be present in individual amounts ranging from about 2 to about 10%, preferably about 3 to about 8%, weight based on the total weight of the composition.
  • compositions of the present invention may also contain further optional ingredients customary in the art such as fluoride ion sources, anticalculus agents, buffers, flavouring agents, sweetening agents, colouring agents, opacifying agents, preservatives, antisensitivity agents and antimicrobial agents.
  • Directly esterified fatty isethionate a mixture of about 70wt% (by weight based on total mixture weight) of sodium cocoyi isethionate with about 20wt% (by weight based on total mixture weight) of free palmitic and stearic fatty acids

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Emergency Medicine (AREA)
  • Cosmetics (AREA)

Abstract

La présente invention concerne une composition de soin buccal comprenant : (a) une phase liquide continue comprenant de l'eau ou un polyol, ou un mélange de ces derniers; (b) de 3 à 75 % en poids (en poids basé sur le poids total de la composition de soin buccal) d'agent de nettoyage particulaire abrasif; (c) de 0,5 à 5 % en poids (en poids basé sur le poids total de la composition de soin buccal) de produit d'iséthionate d'acyle gras; (d) de 0,1 à 2 % en poids (en poids basé sur le poids total de la composition de soin buccal) de tensioactif amphotérique; et (e) de 0 à 1,5 % en poids (en poids basé sur le poids total de la composition de soin buccal) de tensioactif anionique de sulfate d'alkyle. Selon l'invention, le produit d'iséthionate d'acyle gras est défini en tant que mélange comprenant : (i) de 40 à 80 % en poids (en poids basé sur le poids total du produit d'iséthionate d'acyle gras) d'un ou de plusieurs sels d'iséthionate d'acyle gras de la formule générale (I) : R1C(O)OR2 SO3M ; dans la formule (I), R1 est choisi à partir de radicaux d'hydrocarbure monovalents, linéaires ou ramifiés, saturés ou insaturés possédant 5 à 31 atomes de carbone, R2 est choisi à partir de radicaux d'hydrocarbure divalents, linéaires ou ramifiés, saturés comprenant de 2 à 6 atomes de carbone, et M est un cation solubilisant (comme de lithium, de sodium, de potassium, d'ammonium ou d'ammonium substitué); et (ii) de 15 à 50 % en poids (en poids basé sur le poids total du produit d'iséthionate d'acyle gras) d'un ou de plusieurs acides gras de la formule R1C(O)OX, R1 étant tel que défini ci-dessus et X étant de l'hydrogène ou un cation solubilisant M tel que défini ci-dessus.
PCT/EP2013/060473 2012-06-26 2013-05-22 Compositions de soin buccal WO2014000982A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP12173555.9 2012-06-26
EP12173555 2012-06-26

Publications (1)

Publication Number Publication Date
WO2014000982A1 true WO2014000982A1 (fr) 2014-01-03

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PCT/EP2013/060473 WO2014000982A1 (fr) 2012-06-26 2013-05-22 Compositions de soin buccal

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Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2955985A (en) * 1956-06-18 1960-10-11 Bristol Myers Co Dentifrice compositions
US4828824A (en) * 1986-09-15 1989-05-09 L'oreal Dentifrice containing a poly(hydroxypropyl ether) non-ionic surfactant and a salt of a specific derivative of a protein degradation product
EP0354447A2 (fr) * 1988-08-10 1990-02-14 The Procter & Gamble Company Compositions orales
US5120528A (en) * 1991-06-12 1992-06-09 Block Drug Company, Inc. Taste preserving, mild oral hygiene compositions
US5622689A (en) * 1994-05-13 1997-04-22 The Procter & Gamble Company Oral compositions
US20040052736A1 (en) * 2002-09-12 2004-03-18 The Procter & Gamble Company Dentifrice compositions comprising talc
WO2005021701A1 (fr) * 2003-08-27 2005-03-10 Unilever Plc Detergent en pain ameliore et son procede de fabrication
WO2007091856A1 (fr) * 2006-02-10 2007-08-16 Lg Household & Health Care Ltd. Fusion et gélification sur place de composition de comprimé pour soins buccaux
US20080272339A1 (en) * 2007-05-02 2008-11-06 Conopco, Inc. D/B/A Unilever No-strip process for producing bars comprising acyl-isethionate and free fatty acid, and having consumer desirable properties
WO2010114538A1 (fr) * 2009-04-01 2010-10-07 Colgate-Palmolive Company Dentifrice désensibilisant présentant une absorption d'agent antibactérien pour tissu dentaire
EP2371347A2 (fr) * 2010-03-31 2011-10-05 McNeil-PPC, Inc. Compositions de soins buccaux

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2955985A (en) * 1956-06-18 1960-10-11 Bristol Myers Co Dentifrice compositions
US4828824A (en) * 1986-09-15 1989-05-09 L'oreal Dentifrice containing a poly(hydroxypropyl ether) non-ionic surfactant and a salt of a specific derivative of a protein degradation product
EP0354447A2 (fr) * 1988-08-10 1990-02-14 The Procter & Gamble Company Compositions orales
US5120528A (en) * 1991-06-12 1992-06-09 Block Drug Company, Inc. Taste preserving, mild oral hygiene compositions
US5622689A (en) * 1994-05-13 1997-04-22 The Procter & Gamble Company Oral compositions
US20040052736A1 (en) * 2002-09-12 2004-03-18 The Procter & Gamble Company Dentifrice compositions comprising talc
WO2005021701A1 (fr) * 2003-08-27 2005-03-10 Unilever Plc Detergent en pain ameliore et son procede de fabrication
WO2007091856A1 (fr) * 2006-02-10 2007-08-16 Lg Household & Health Care Ltd. Fusion et gélification sur place de composition de comprimé pour soins buccaux
US20080272339A1 (en) * 2007-05-02 2008-11-06 Conopco, Inc. D/B/A Unilever No-strip process for producing bars comprising acyl-isethionate and free fatty acid, and having consumer desirable properties
WO2010114538A1 (fr) * 2009-04-01 2010-10-07 Colgate-Palmolive Company Dentifrice désensibilisant présentant une absorption d'agent antibactérien pour tissu dentaire
EP2371347A2 (fr) * 2010-03-31 2011-10-05 McNeil-PPC, Inc. Compositions de soins buccaux

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