WO1996001616A1 - Composition a base d'ester de polyglycerol et son procede de production - Google Patents

Composition a base d'ester de polyglycerol et son procede de production Download PDF

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Publication number
WO1996001616A1
WO1996001616A1 PCT/US1995/009387 US9509387W WO9601616A1 WO 1996001616 A1 WO1996001616 A1 WO 1996001616A1 US 9509387 W US9509387 W US 9509387W WO 9601616 A1 WO9601616 A1 WO 9601616A1
Authority
WO
WIPO (PCT)
Prior art keywords
composition
polyglycerol ester
water
dentifrice
polyol
Prior art date
Application number
PCT/US1995/009387
Other languages
English (en)
Inventor
Andre Joseph Eydt
Original Assignee
Lonza Inc.
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 Lonza Inc. filed Critical Lonza Inc.
Priority to AU31461/95A priority Critical patent/AU3146195A/en
Publication of WO1996001616A1 publication Critical patent/WO1996001616A1/fr

Links

Classifications

    • 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
    • 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
    • A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
    • 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
    • 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
    • C11D1/66—Non-ionic compounds
    • C11D1/667—Neutral esters, e.g. sorbitan esters
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2003—Alcohols; Phenols
    • C11D3/2041—Dihydric alcohols
    • C11D3/2044—Dihydric alcohols linear
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2003—Alcohols; Phenols
    • C11D3/2065—Polyhydric alcohols

Definitions

  • This invention relates to polyglycerol ester additives for a wide variety of formulations, such as personal care products, particularly dentifrices, containing such additives as surfactants and/or viscosity modifiers.
  • Conventional personal care formulations such as dentifrices, generally contain surfactants to increase their cleaning action and provide the foaming properties expected by the user.
  • Polyglycerol esters have been used for this purpose, as described in U.S. Patent 4,865,839 to Saso.
  • a dentifrice should be formulated to conveniently extrude from a tube as a ribbon, break sharply, and retain integrity for a reasonable period of time on a toothbrush.
  • dentifrices containing polyglycerol esters require additional thickeners, such as sodium carboxymethyl cellulose, carrageenan or polyethylene glycol, to control formulation flow properties.
  • additional thickeners such as sodium carboxymethyl cellulose, carrageenan or polyethylene glycol
  • polyglycerol esters are insoluble in water at room temperature, and the highly viscous solutions which result when the compound is mixed with water cannot readily be added to the dentifrice in a room temperature manufacturing process.
  • the polyglycerol esters may be added to the dentifrice formulation using a high temperature processing step, but such a procedure is undesirable because it is not part of the conventional manufacturing processes.
  • polyglycerol esters provide many potential benefits in personal care formulations
  • the use of these compounds requires incorporation of additional thickening ingredients in the formulation, or a difficult to implement high temperature processing step.
  • a polyglycerol ester composition has now been discovered which may be incorporated into personal care products at room temperature in a conventional manufacturing process.
  • the resulting personal care products do not require additional thickening agents to control their viscosity.
  • the present invention also includes a method of preparing a polyglycerol ester composition for subsequent introduction at room temperature into a personal care formulation.
  • the polyglycerol ester is first added to a mixture of a polyol and water at a temperature above room temperature, and allowed to cool to room temperature to produce a polyglycerol ester additive composition.
  • the resulting composition is flowable at room temperature, and may easily be incorporated at room temperature into dentifrices and other personal care products.
  • the polyglycerol ester composition of the invention makes it possible to prepare personal care products at room temperature which are thickened with polyglycerol esters, and are substantially free of other viscosity modifiers, without altering the conventional manufacturing process.
  • the resulting personal care products are an improvement over prior art in that a well performing product can be more simply and economically manufactured with a smaller number of ingredients.
  • the polyglycerol ester composition of the invention is formulated with an amount of water sufficient to prevent gelation of the composition at room temperature, i.e., with a viscosity of less than 100K cps, but not so great as to permit the spoilage of the composition by microorganisms such as bacteria, molds and yeasts.
  • the properly prepared composition has a long shelf life, i.e., it may be stored for extended periods, e.g., up to six months.
  • the polyglycerol ester composition of the invention may be utilized as a surfactant and viscosity modifier in a wide variety of formulations. It is provided as a liquid composition which, while flowable at room temperature, thickens to the desired viscosity upon the introduction of additional formulation ingredients.
  • the polyglycerol ester composition of the invention comprises about 1 to 5 wt% of a polyglycerol fatty acid ester, about 1 to 20 wt% of water, and about 75 to 95 wt% of a polyol. It generates the desired viscosity when incorporated into a personal care formulation.
  • the polyglycerol esters have 6 to 12 glycerol units, more preferably, 6 to 10, 1 to 3 ester linkages, more preferably, 1 or 2.
  • the fatty acids used for esterification may have from 10 to 20 carbon atoms, preferably, from 12 to 18.
  • polyglycerol esters are hexaglyceryl distearate, decaglyceryl mono- and dipalmitate, decaglyceryl mono and distearate, and mixtures thereof.
  • the preferred polyglycerol esters are decaglyceryl distearate and decaglyceryl dipalmitate.
  • the polyols which can be utilized in the composition of the invention may vary widely and include any polyol which is compatible with the polyglycerol ester and the resultant personal care formulation.
  • Typical examples of polyols which may be used include glycerol, polyglycerol, propylene glycol, sorbitol and hydrogenated starch hydrolysates.
  • the preferred polyols are glycerol and sorbitol, and the most preferred is glycerol.
  • Mixtures of polyols may also be used, such as, mixtures of sorbitol and glycerol or mixtures of sorbitol with polyglycerols.
  • the water utilized in formulating the composition of the invention should be of a high purity, e.g., deionized water or distilled water.
  • the amount added is such that the water activity of the finished solution is below 0.7 and preferably below 0.5.
  • the water activity is the relative humidity over the solution at a given temperature, and is measured with a hygrometer, such as the AquaLab, manufactured by Decagon Devices, Pullman, Washington. If the water activity level is maintained below 0.7, no preservatives need be added to the composition of the invention and a long shelf life is assured.
  • the composition of the invention is prepared by dissolving the polyglycerol ester in a solution containing the polyol and water.
  • the dissolution is performed at a temperature of about 60 °C to about 80 °C with stirring, preferably, at about 75 °C.
  • the composition is cooled to room temperature.
  • the amount of water added to the composition of the invention should be sufficient to prevent gelation of the composition at temperatures from about 15 to 30°C.
  • the amount needed varies depending on the particular polyglycerol ester employed.
  • the viscosity of the solution should not be above about 150K cps at a temperature of 25 °C, as measured by a Brookfield Viscometer. Typical viscosities range from about 5K cps to 100K cps, preferably, about 10K cps to 40K cps, at a temperature of 25 °C.
  • composition of the invention may be prepared well in advance at a different location from the final product, as for example by the supplier of the polyglycerol esters.
  • the shelf life is normally in excess of about 6 months.
  • the polyglycerol ester composition may be utilized alone to control the texture and flow properties of a personal care formulations, or in combination with a minor amount of other conventional viscosity modifiers such as, for example, sodium carboxymethyl cellulose, carrageenan or polyethylene glycol.
  • the effective amount is about 0.5% by weight to about 2 wt%, preferably, about 1 wt%. These ranges are particularly applicable to a dentifrice.
  • the dentifrices may include a wide variety of conventional ingredients which are well known in the art.
  • abrasives such as silicas, calcium carbonate, dicalcium phosphate, calcium pyrophosphate, insoluble sodium metaphosphate, and silicic anhydride
  • humectants such as glycerol, sorbitol, hydrogenated starch hydroiysates, propylene glycol and polyethylene glycol
  • binders such as carboxymethyl cellulose, carrageenan, sodium alginate, locust bean gum, hydroxyethyl cellulose and polyvinyl alcohol
  • sweeteners such as sodium saccharin, glycyrrhizin salts, steviocide, neohesperidin dihydrochalcone, p-methoxycinnamic aldehyde and perillartine
  • flavors such as carvone, anethole, peppermint, spearmint and cinnamon
  • bactericides such as fluor
  • a typical dentifrice formulation which may be made using the composition of the invention is composed of 30 to 70 wt% of a polyol humectant, such as USP sorbitol; 10 to 50 wt% of an abrasive, such as Zeodent ® 1 13 or 165 (Zeodent is a trademark for precipitated silica abrasives made by the J.M. Huber Corp.); 0.3 to 2 wt% of the polyglycerol ester; and further includes a small amount of a flavoring agent, such as mint extract.
  • the composition generally contains about 5 to 30 wt% water. To more fully illustrate the invention the following examples are presented. It will be understood, however, that these examples are not intended to limit the scope of the invention.
  • the polyglycerol ester composition and the dentifrice formulation were easily mixed by hand with a spatula until a smooth paste was formed.
  • the resulting paste could be easily extruded from a tube and retained its integrity for a reasonable time when applied to a toothbrush.
  • the paste showed no syneresis after six month storage at 25 °C, illustrating that dentifrices prepared with the polyglycerol ester composition of the invention will maintain their viscosity over an extended period.
  • Viscosity 25 °C
  • compositions were prepared to establish the most useful range of ingredients compatible with the conventional dentifrice manufacturing process, while still producing a toothpaste with good shelf-stability.
  • Part B A therapeutic solution for forming a dentifrice was prepared by mixing of 195 parts by weight of 70% USP sorbitol, 1.2 parts by weight sodium fluoride, and 8 parts by weight water. To produce the dentifrice, 29.4 g of the polyglycerol ester Composition C were admixed and blended at room temperature with 40.8 g of the therapeutic solution, 18.0 g Zeodent 113, 5.5 g Zeodent 165, and 0.5 ml mint extract. The blending was easily done by hand at room temperature with a spatula.
  • Composition A which contained 3.5 parts of the polyglycerol ester and 14.5 parts of water, formed a non-flowable gel when cooled to room temperature, and could not be blended with a dentifrice formulation.
  • Composition B in which the amount of polyglycerol ester was reduced to 1.7 parts, was less viscous than composition A, but was too viscous at room temperature to easily blend with a dentifrice formulation.
  • Composition C in which the amount of polyglycerol ester was reduced to 1 part by weight, contained a sufficient amount of water, about 15 parts, to flow easily at room temperature and blend with the dentifrice formulation to form a toothpaste.
  • Composition C also contained sufficient amounts of polyglycerol ester such that, when the dentifrice was added, the composition thickened and formed a toothpaste which could be conveniently extruded from a tube, and which retained its integrity for a reasonable period of time on a toothbrush.
  • the dentifrice paste produced using composition C did not develop any syneresis following storage at room temperature for 6 months; the paste made with composition D failed after one week.

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

Abstract

Une composition liquide comprend 1 à 5 % en poids environ d'un ester d'acide gras de polyglycérol, 1 à 20 % en poids environ d'eau et 75 à 95 % en poids environ d'un polyol. On décrit un procédé permettant de produire de telles compositions, ainsi que des formulations pour soins d'hygiène personnelle qui contiennent de telle compositions. Ce procédé consiste à dissoudre un ester de polyglycérol, à une température allant de 60 à 80 °C environ, dans une solution comprenant un polyol et de l'eau, la quantité d'eau étant suffisante pour prévenir la gélification de cette composition à température ambiante.
PCT/US1995/009387 1994-07-11 1995-07-10 Composition a base d'ester de polyglycerol et son procede de production WO1996001616A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU31461/95A AU3146195A (en) 1994-07-11 1995-07-10 Polyglycerol ester composition and method for its production

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US27340394A 1994-07-11 1994-07-11
US273,403 1994-07-11

Publications (1)

Publication Number Publication Date
WO1996001616A1 true WO1996001616A1 (fr) 1996-01-25

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ID=23043796

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1995/009387 WO1996001616A1 (fr) 1994-07-11 1995-07-10 Composition a base d'ester de polyglycerol et son procede de production

Country Status (3)

Country Link
AU (1) AU3146195A (fr)
IL (1) IL114550A0 (fr)
WO (1) WO1996001616A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8466100B2 (en) 2008-08-15 2013-06-18 The Procter & Gamble Company Benefit compositions comprising polyglycerol esters

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4435380A (en) * 1982-01-29 1984-03-06 Lever Brothers Company Humectants for clear gel dentifrice compositions
US4865839A (en) * 1986-09-02 1989-09-12 Lion Corporation Oral composition containing a polyglycerol fatty acid monoester and an N-acylamino acid or a salt thereof
US5109127A (en) * 1989-11-06 1992-04-28 Lion Corporation Nonionic surface active agent
US5130060A (en) * 1983-10-14 1992-07-14 Igor Beseda Method of manufacturing polyglycerol esters
US5154855A (en) * 1989-11-14 1992-10-13 Lion Corporation Emulsified composition

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4435380A (en) * 1982-01-29 1984-03-06 Lever Brothers Company Humectants for clear gel dentifrice compositions
US5130060A (en) * 1983-10-14 1992-07-14 Igor Beseda Method of manufacturing polyglycerol esters
US4865839A (en) * 1986-09-02 1989-09-12 Lion Corporation Oral composition containing a polyglycerol fatty acid monoester and an N-acylamino acid or a salt thereof
US5109127A (en) * 1989-11-06 1992-04-28 Lion Corporation Nonionic surface active agent
US5154855A (en) * 1989-11-14 1992-10-13 Lion Corporation Emulsified composition

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8466100B2 (en) 2008-08-15 2013-06-18 The Procter & Gamble Company Benefit compositions comprising polyglycerol esters

Also Published As

Publication number Publication date
IL114550A0 (en) 1995-11-27
AU3146195A (en) 1996-02-09

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