WO1988010147A1 - Composition moussante - Google Patents

Composition moussante Download PDF

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Publication number
WO1988010147A1
WO1988010147A1 PCT/DK1988/000099 DK8800099W WO8810147A1 WO 1988010147 A1 WO1988010147 A1 WO 1988010147A1 DK 8800099 W DK8800099 W DK 8800099W WO 8810147 A1 WO8810147 A1 WO 8810147A1
Authority
WO
WIPO (PCT)
Prior art keywords
hexose
ester
foaming
glucose
composition
Prior art date
Application number
PCT/DK1988/000099
Other languages
English (en)
Inventor
Martin Barfoed
Fredrik Bjoerkling
Original Assignee
Novo-Nordisk A/S
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 Novo-Nordisk A/S filed Critical Novo-Nordisk A/S
Publication of WO1988010147A1 publication Critical patent/WO1988010147A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/34—Higher-molecular-weight carboxylic acid 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/662—Carbohydrates or derivatives
    • 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
    • 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
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
    • C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
    • C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
    • C07H13/06—Fatty acids
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • 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
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/0094—High foaming compositions

Definitions

  • This invention relates to foaming cleaning and personal-care compositions, such as shampoo, shaving cream, tooth paste, carpet shampoo, dish-washing liquid, foaming industrial cleaner, and liquid soap, and to foaming food compositions, such as sponge cake, whipping cream and ice cream.
  • foaming cleaning and personal-care compositions such as shampoo, shaving cream, tooth paste, carpet shampoo, dish-washing liquid, foaming industrial cleaner, and liquid soap
  • foaming food compositions such as sponge cake, whipping cream and ice cream.
  • the ability to create a voluminous foam is considered essential in the compositions to which the invention relates.
  • a number of foaming agents are known, and can be incorporated to achieve the desired foaming.
  • foaming agents include anionics, nonionics and amphoterics. Many of them are also active as surfactants and/or emulsifiers.
  • anionic foaming agents is alkyl ether sulphate (AES) , especially sodium lauryl ether sulphate, which is commonly incorporated in shampoo to provide foaming and cleaning effect.
  • An example of nonionic foaming agents is coconut fatty acid diethanol amide (CDE), which is commonly used together with AES in shampoo to increase the foaming.
  • Carbohydrate fatty acid esters are also known as ingredients in some foaming personal-care, cleaning and food compositions, such as shampoo, tooth paste, shaving cream, sponge cake and whipping cream.
  • the carbohydrate fatty acid esters used in the above-mentioned prior art are mono-esters or mixtures of mono- and di-esters of sucrose or other oligosaccharides with fatty acids of 12-20 carbon atoms.
  • the prior art indicates that incorporation of these esters improves the foaming of some products, but that the foaming is in some cases less than desired.
  • the prior art indicates that in some cases the carbohydrate ester performs other useful functions, e.g. as an emulsifier or a surfactant. It is the object of the invention to provide foaming cleaning and personal-care compositions and foaming food compositions comprising carbohydrate fatty acid ester with improved foaming.
  • the group consists of the monoesters, wherein the carbohydrate is a hexose (monohexose) and the acyl group is straight-chain with 7-10 carbon atoms.
  • the foaming ability of these hexose esters is better than that of carbohydrate esters used in the prior art and better than similar hexose esters with a shorter or longer acyl group (acyl group with 6 or 12 carbon atoms) .
  • the invention provides a foaming personal-care or cleaning composition, containing as an essential ingredient therein a hexose fatty acid ester, said fatty acid being heptanoic, octanoic, nonanoic or decanoic acid.
  • the invention also provides a foaming food composition containing as an essential ingredient therein a hexose fatty acid ester, said fatty acid being heptanoic, octanoic, nonanoic or decanoic acid. 5
  • hexose esters of the invention contain a single acyl group attached to the oxygen atom of any hydroxyl group in a hexose (monohexose).
  • the hexose may be an aldose or a ketose.
  • Glucose, galactose or fructose (D-forms) are preferred for reasons of 0 economy.
  • the acyl group has a straight chain with 7-10 carbon atoms. It is heptanoyl (enanthyl), octanoyl
  • acyl groups with an even number of carbon atoms (i.e. 5 octanoyl and decanoyl) are preferred due to raw material availability.
  • 3- or 6-position (3-0-acyl-D-glucose or 6-0-acyl-D-glucose) are preferred due to ease of preparation.
  • two particularly preferred hexose esters are
  • hexose esters of the invention can be prepared according to methods known in the art. See E. Reinefeld, supra; K. Yoshimoto et al «, Chem.Pharm.Bull. , 2_7_(11), 2661- 2674(1979) .
  • Foaming, cleaning and personal-care compositions form a class of products where foaming is considered essential.
  • Typical products in this class are shampoo, shaving cream, tooth paste, carpet shampoo, dish-washing liquid, foaming industrial cleaner or liquid soap.
  • Concerning the importance of foaming in some of these products see Journal of the Society of Cosmetic Chemists, vol. 10, pp. 390-414 (.1960).
  • Preferred ranges for the amount of hexose ester of the invention are as follows (% by weight):
  • Shampoo e.g. hair shampoo, body shampoo
  • the shampoo of the invention may contain the hexose ester as the main surfactant, in which case the content is preferably 10-20%.
  • the shampoo may contain a combination of the hexose ester (e.g. 1-10%) with anionic surfactant (e.g. 10-20%).
  • the anionic may be linear alkyl benzene sulphonate (LAS) or alkyl ether sulphate (AES, especially sodium lauryl ether sulphate) .
  • the shampoo of the invention may contain a foam booster (e.g. 0.5-8%), such as a long-chain fatty acid dialkanol amide (e.g. the aforementioned CDE), a long-chain N-acyl amino acid (e.g. N-acyl-sarcosinate or N- acylglutamate) or a betain derivative.
  • a foam booster e.g. 0.5-8%
  • the anionic surfactant may be linear alkyl benzene sulphonate (LAS) or alkyl ether anionic sulphate (AES). If shampoo with higher viscosity is desired, this can be obtained by incorporating a thickener known in the art such as CMC (carboxy-methyl cellulose) or, in case AES is also used, it can be controlled by incorporation of salt.
  • LAS linear alkyl benzene sulphonate
  • AES alkyl ether anionic sulphate
  • compositions are formulated as follows:
  • the foaming food composition of the invention may be sponge cake, whipping cream or ice cream. These products form a class where foaming is considered essential.
  • the hexose ester of the invention is preferably incorporated in an amount of 0.1-2.0% (by weight), to improve the foaming.
  • the hexose ester may also act as an emulsifier in these compositions.
  • glucose esters used each consisted of approx 85% of 6-ester (ester with the acyl group in the 6-position of glucose) and approx 15% of 3- ester.
  • AES alkyl ether sulphate
  • CDE indicates coconut acid diethanolamide (Empilan CDE, Albright & Wilson, United Kingdom) .
  • volume of foam collected 2 liters - Inner diameter of foam tube: 26 mm
  • This glucosyl-octanoate 75 seconds invention glucosyl-decanoate 130 -
  • sucrose esters were chosen to represent the carbohydrate esters of prior-art shampoos, that are most similar to the esters of the invention, and to represent various ratios of monoester to higher esters. It is seen that foaming of sucrose esters used in the prior art are far inferior to the invention.
  • Foaming was measured with 2% of AES and 0.4% of a test compound to show foam boosting effect (all % as active material). Results (filling times) were as follows:
  • ester of the invention is active as a foam booster, as it gives better foaming than AES alone used at the same concentration.
  • CDE was more effective as a foam booster.
  • a shampoo was formulated as follows (% as active matter) :
  • the shampoo was found to show good foaming when used for washing of the hair by test persons.
  • the ingredients are mixed with a whipper, and the batter is baked at 200°C for 25 min.
  • Tooth pastes are prepared by kneading the following ingredients:
  • NTA Nitrilo tri-acetic acid
  • Additives include coloring agent, perfume, and preservative.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Materials Engineering (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Genetics & Genomics (AREA)
  • Biotechnology (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Cosmetics (AREA)
  • Detergent Compositions (AREA)

Abstract

Des compositions moussantes de nettoyage, de soins personnels et de produits alimentaires, tels que shampooings, etc., contiennent un ester d'acide gras d'hexose. L'ester comporte un groupe acyle ayant 7 à 10 atomes de carbone et présentent un pouvoir moussant accru.
PCT/DK1988/000099 1987-06-23 1988-06-23 Composition moussante WO1988010147A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DK3183/87 1987-06-23
DK318387A DK318387D0 (da) 1987-06-23 1987-06-23 Overfladeaktivt stof og dets anvendelse

Publications (1)

Publication Number Publication Date
WO1988010147A1 true WO1988010147A1 (fr) 1988-12-29

Family

ID=8120018

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/DK1988/000099 WO1988010147A1 (fr) 1987-06-23 1988-06-23 Composition moussante

Country Status (2)

Country Link
DK (1) DK318387D0 (fr)
WO (1) WO1988010147A1 (fr)

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1990008182A1 (fr) * 1989-01-23 1990-07-26 Novo Nordisk A/S Composition detergente de blanchissage
EP0380406A2 (fr) * 1989-01-25 1990-08-01 Colgate-Palmolive Company Composition détergente pour matériaux textiles fins avec des esters de sucre comme agents adoucissants et de blanchiment
EP0423968A1 (fr) * 1989-10-06 1991-04-24 Unilever Plc Composition détergente
EP0427210A2 (fr) * 1989-11-06 1991-05-15 Lion Corporation Agent tensioactif non ionique
EP0428157A2 (fr) * 1989-11-14 1991-05-22 Lion Corporation Composition émulsifiée
EP0485251A1 (fr) * 1990-11-09 1992-05-13 L'oreal Composition cosmétique, pharmaceutique ou alimentaire comportant une dispersion de vésicules lipidiques
US5190747A (en) * 1989-11-06 1993-03-02 Lion Corporation Oral or detergent composition comprising a nonionic surface active agent
FR2698004A1 (fr) * 1992-11-13 1994-05-20 Oreal Dispersion aqueuse cosmétique ou dermatologique pour le traitement des cheveux ou de la peau, à base d'esters d'acide gras de sucre ou d'alkylsucre et de copolymères réticulés d'acrylamide.
WO1995005798A1 (fr) * 1993-08-24 1995-03-02 Henkel Kommanditgesellschaft Auf Aktien Compositions aqueuses douces de rasage
FR2731365A1 (fr) * 1995-03-10 1996-09-13 Agency Of Ind Science Et Techn Tensioactif glycolipidique et procede pour sa preparation
WO2001070188A1 (fr) * 2000-03-21 2001-09-27 Unilever Plc Creme de jour a faible ph et a teneur elevee en acide gras
WO2003092644A2 (fr) * 2002-04-29 2003-11-13 Symrise Gmbh & Co. Kg Produits d'hygiene buccale
WO2004064799A1 (fr) * 2003-01-17 2004-08-05 Cognis Ip Management Gmbh Gels d'agent tensioactif aqueux a cristaux liquides

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2973353A (en) * 1956-06-29 1961-02-28 Monsanto Chemicals Carbohydrate mono-esters
US3231561A (en) * 1962-01-03 1966-01-25 Economics Lab Fatty acid sugar esters and fatty acid sugar-boron esters
US4450090A (en) * 1983-05-16 1984-05-22 Clairol Incorporated Thickened alpha-olefin sulfonate containing formulations

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2973353A (en) * 1956-06-29 1961-02-28 Monsanto Chemicals Carbohydrate mono-esters
US3231561A (en) * 1962-01-03 1966-01-25 Economics Lab Fatty acid sugar esters and fatty acid sugar-boron esters
US4450090A (en) * 1983-05-16 1984-05-22 Clairol Incorporated Thickened alpha-olefin sulfonate containing formulations

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, Vol. 100 (1984), abstract No. 108977 w, CS 206 143. *
CHEMICAL ABSTRACTS, Vol. 102 (1985), abstract No. 119422 d; & JP,A,59 184 299. *
DERWENT'S ABSTRACT NO. 79-86601 B/48; & JP,A,54 134 711. *

Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5431849A (en) * 1989-01-23 1995-07-11 Novo Nordisk A/S Bleaching detergent composition containing acylated sugar bleach activators
WO1990008182A1 (fr) * 1989-01-23 1990-07-26 Novo Nordisk A/S Composition detergente de blanchissage
EP0380406A2 (fr) * 1989-01-25 1990-08-01 Colgate-Palmolive Company Composition détergente pour matériaux textiles fins avec des esters de sucre comme agents adoucissants et de blanchiment
EP0380406A3 (fr) * 1989-01-25 1991-03-06 Colgate-Palmolive Company Composition détergente pour matériaux textiles fins avec des esters de sucre comme agents adoucissants et de blanchiment
EP0423968A1 (fr) * 1989-10-06 1991-04-24 Unilever Plc Composition détergente
US5190747A (en) * 1989-11-06 1993-03-02 Lion Corporation Oral or detergent composition comprising a nonionic surface active agent
EP0427210A2 (fr) * 1989-11-06 1991-05-15 Lion Corporation Agent tensioactif non ionique
US5109127A (en) * 1989-11-06 1992-04-28 Lion Corporation Nonionic surface active agent
EP0427210A3 (fr) * 1989-11-06 1995-01-18 Lion Corp
EP0428157A3 (en) * 1989-11-14 1991-07-31 Lion Corporation An emulsified composition
US5154855A (en) * 1989-11-14 1992-10-13 Lion Corporation Emulsified composition
EP0428157A2 (fr) * 1989-11-14 1991-05-22 Lion Corporation Composition émulsifiée
EP0485251A1 (fr) * 1990-11-09 1992-05-13 L'oreal Composition cosmétique, pharmaceutique ou alimentaire comportant une dispersion de vésicules lipidiques
FR2668930A1 (fr) * 1990-11-09 1992-05-15 Oreal Composition cosmetique, pharmaceutique ou alimentaire comportant une dispersion aqueuse de vesicules lipidiques.
US5268180A (en) * 1990-11-09 1993-12-07 L'oreal Cosmetic pharmaceutical or foodstuff composition comprising an aqueous dispersion of lipidic vesicles
FR2698004A1 (fr) * 1992-11-13 1994-05-20 Oreal Dispersion aqueuse cosmétique ou dermatologique pour le traitement des cheveux ou de la peau, à base d'esters d'acide gras de sucre ou d'alkylsucre et de copolymères réticulés d'acrylamide.
US5368850A (en) * 1992-11-13 1994-11-29 L'oreal Aqueous cosmetic or dermatological dispersion for treatment of hair or skin based on sugar or alkylsugar fatty acid esters and reticulated acrylamide copolymers
EP0603019A1 (fr) * 1992-11-13 1994-06-22 L'oreal Dispersion aqueuse cosmétique ou dermatologique à base d'esters d'acide gras de sucre et de copolymères réticulés d'acrylamide
WO1995005798A1 (fr) * 1993-08-24 1995-03-02 Henkel Kommanditgesellschaft Auf Aktien Compositions aqueuses douces de rasage
FR2731365A1 (fr) * 1995-03-10 1996-09-13 Agency Of Ind Science Et Techn Tensioactif glycolipidique et procede pour sa preparation
WO2001070188A1 (fr) * 2000-03-21 2001-09-27 Unilever Plc Creme de jour a faible ph et a teneur elevee en acide gras
WO2003092644A2 (fr) * 2002-04-29 2003-11-13 Symrise Gmbh & Co. Kg Produits d'hygiene buccale
WO2003092644A3 (fr) * 2002-04-29 2004-04-22 Symrise Gmbh & Co Kg Produits d'hygiene buccale
WO2004064799A1 (fr) * 2003-01-17 2004-08-05 Cognis Ip Management Gmbh Gels d'agent tensioactif aqueux a cristaux liquides

Also Published As

Publication number Publication date
DK318387D0 (da) 1987-06-23

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