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WO2003095601A1 - Derives d'acides gras ramifies en tant qu'ingredients de regulation de la viscosite ou d'anti-gelification - Google Patents

Derives d'acides gras ramifies en tant qu'ingredients de regulation de la viscosite ou d'anti-gelification Download PDF

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Publication number
WO2003095601A1
WO2003095601A1 PCT/IB2003/001970 IB0301970W WO03095601A1 WO 2003095601 A1 WO2003095601 A1 WO 2003095601A1 IB 0301970 W IB0301970 W IB 0301970W WO 03095601 A1 WO03095601 A1 WO 03095601A1
Authority
WO
WIPO (PCT)
Prior art keywords
formula
saturated
compound
unsaturated hydrocarbon
independently
Prior art date
Application number
PCT/IB2003/001970
Other languages
English (en)
Inventor
Ferdinand Naef
Thierry Stora
Olivier Haefliger
Original Assignee
Firmenich Sa
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 Firmenich Sa filed Critical Firmenich Sa
Priority to EP03720814A priority Critical patent/EP1506275A1/fr
Publication of WO2003095601A1 publication Critical patent/WO2003095601A1/fr
Priority to US10/988,016 priority patent/US20050176609A1/en

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Classifications

    • 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
    • C11D3/001—Softening compositions
    • C11D3/0015—Softening compositions liquid
    • 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
    • C11D1/38—Cationic compounds
    • C11D1/62—Quaternary ammonium compounds
    • 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
    • C11D3/50—Perfumes

Definitions

  • the present invention relates to the field of softeners. More particularly, the invention concerns a compound derived from a 3-(dialkylamino)-l,2-propanediol and a non-linear fatty acid, as well as the use of said compound as anti-gelling or viscosity- control ingredient in softening articles.
  • Gelation of softening articles is a known problem which is notably enhanced, at low or high temperature, by a prolonged storage time and/or the presence of alcohols, in particular perfumery alcohols.
  • This gelation manifests itself macroscopically by an increase of the composition viscosity and a concomitant and irreversible thickening, or sometimes even by a solidification of the softener compositions.
  • the gelation is believed to be due to the surfactants present in composition, and possibly to the interactions of said surfactants with other ingredients.
  • all existing or commercial softener compositions contain surfactants which have a linear chain residue.
  • EP 280550 discloses the use of non-ionic surfactants, e.g. alkoxylated aliphatic alcohols, as a viscosity-control agent or an anti-gelling ingredient in softener compositions containing not more that 6% of a cationic fabric softener and a free fatty acid.
  • non-ionic surfactants e.g. alkoxylated aliphatic alcohols
  • WO 95/22594 teaches the use of a perfume which is associated with a carrier to avoid the gelation of bases containing ionic surfactants; however this solution is useful only when the gelation is due to the sole perfume.
  • WO 97/17419 proposes to use specific non-ionic di- or tri- esters.
  • the present invention relates to the use of a compound as anti-gelling or viscosity-control ingredient, i.e. capable of preventing or delaying the gelation of a softener composition.
  • Said compound is a nonlinear fatty acid derivative.
  • nonlinear fatty acid we mean here a fatty acid having at least a tertiary carbon atom in its hydrocarbon radical, or a fatty acid having up to six hydroxyl functions, said hydroxyl being possibly derivatized as ethers or esters bonded to its hydrocarbon radical.
  • a fatty acid having at least a tertiary carbon atom in its hydrocarbon radical we mean here a fatty acid containing a moiety which is cyclic, aromatic or branched.
  • Non-limiting examples of said non-linear fatty acid are of the formulae (a), (b) or (c) wherein the asterisk indicate one of the tertiary carbon atom:
  • Suitable compounds for the purpose of the invention e.g. for a use as anti-gelling ingredient in a softening articles, are of formula
  • n is 0.5 or 1 ;
  • A represents an anion of an acid such as a chloride, a bromide, a iodide, a CO 3 2" or HCO 3 " , a sulfate, a methyl or ethyl sulfate, a tosylate or a nitrate; and each R 1 represents, simultaneously or independently, a hydrogen or oxygen atom, a benzyl or Ci to C 6 alkyl group or a polyethylene- or polypropyleneglycol group, having from 1 to 5 monomer units; and each R 2 represents, simultaneously or independently, a C ⁇ o-C 3 o saturated or unsaturated hydrocarbon radical having at least a tertiary carbon atom, or a C ⁇ o-C 30 saturated or unsaturated hydrocarbon radical having from one to six -OCOR or -OR groups bonded to its hydrocarbon chain; R 3 being an hydrogen atom, or a C ⁇ -C 22 saturated or unsaturated hydrocarbon group
  • the compounds of formula (I) are those wherein n is 0.5 or 1;
  • the compounds of the invention may be obtainable by the reaction of one molar equivalent of an appropriate al andiol amine of formula
  • source of the fatty acid R 2 COOH (R 2 being defined as in formula (I)), or of the corresponding triglyceride
  • R 2 being defined as in formula (I)
  • a natural oil or a product obtained by a transformation of a natural oil examples of such oils are isostearic acids, hydroxystearic acid, ricinoleic acid or polyterpenic acids such as farnesic acid.
  • one of the objects of the present invention is the use as anti-gelling or viscosity-control ingredient of a compound of formula (I).
  • said use consists of a method to prevent or delay the gelation of a softening article, which method comprises adding to said article an effective amount of at least one compound of formula (I).
  • use of a compound of formula (I) it has to be understood here also the use of the compound (I) in any of its forms which can be advantageously employed as anti-gelling ingredient.
  • Said forms are also an object of the present invention. hi an embodiment of the invention, one of said forms is a composition of matter consisting of at least one compound of formula (I) and a perfume base.
  • one of the elements which may be at the origin of the gelling phenomenon is admixed with the anti-gel ingredient, and therefore said two ingredients will be added at the same time into the softener base, minimizing thus any risk of formation of gel into the softening article.
  • perfume base we mean here a composition comprising at least one perfuming compound and possibly one or more solvents or adjuvants commonly used in the perfume industry.
  • perfuming compound it is meant here a compound, which is of current use in the perfume industry, i.e. a compound which is used as ingredient in perfuming preparation or composition in order to impart an hedonic effect.
  • such a compound, to be considered as being a perfuming one must be recognized by a person skilled in the art as being able to impart or modify in a positive or pleasant way the odor of a composition, and not just as having an odor. Its is therefore understood here that any mixture resulting directly from a chemical synthesis in which the compound of the invention is involved as a starting intermediate or as an end-product is not a composition of matter according to the invention.
  • these perfuming co-ingredients belong to chemical classes as varied as alcohols, aldehydes, ketones, esters, ethers, acetates, nitriles, terpene hydrocarbons, nitrogenous or sulphurous heterocyclic compounds and essential oils of natural or synthetic origin. Many of these co-ingredients are in any case listed in reference texts such as the book by S.
  • perfume bases which contain alcohols or aldehydes, as perfuming compounds, are particularly interesting.
  • solvents and adjuvants commonly used in perfume bases cannot be exhaustive. A skilled person in the art is able to select them on the basis of the nature of the product to be perfumed.
  • solvents commonly used in perfumery bases one can cite compounds such as dipropyleneglycol, diethyl phthalate, isopropyl myristate, benzyl benzoate, 2-(2-ethoxyethoxy)-l-ethanol or ethyl citrate, which are the most commonly used.
  • another object of the present invention is a softening article comprising: a) a compound of formula (I), as defined above, or a composition of matter, as defined above, and b) a softening base.
  • a perfumed product according to the invention comprises at least a part of the whole formulation corresponding to an unperfumed softener, e.g. one or more suitable surfactant, an anti-gel effective amount of at least an invention's compound and possibly an olfactive effective amount of a perfume base as defined above.
  • an unperfumed softener e.g. one or more suitable surfactant, an anti-gel effective amount of at least an invention's compound and possibly an olfactive effective amount of a perfume base as defined above.
  • Suitable softening bases comprise fabric softeners, shampoos, hair conditioners and other hair care products or yet skin emollients or cosmetic products.
  • the fabric softeners being the preferred bases.
  • the softening base advantageously contains at least a surfactant obtainable by the reaction of one to three molar equivalents of a C10-C20 fatty acid with one molar equivalent of an amino alcohol of formula
  • a and n are as defined in formula (I), d is 1 or 2, R represents a hydrogen atom or a R 1 group as defined formula (I), m is 2 or 3 and (m+s) - 4.
  • the proportions in which the compounds according to the invention can be incorporated into the various aforementioned compositions or articles vary within a wide range of values. These values are dependent on the nature of the composition or product as well as the nature of the co-ingredients in a given composition.
  • concentrations of the compound of formula (I) in one of the aforementioned product are in the order of 0.01% to 10% by weight, percentage being based on the weight of the article into which they are incorporated. Concentrations higher than these, such as in the order of 2% to 80% by weight, can be used when these compounds are incorporated into compositions.
  • Emersol ® 874 contains approximately 90% w/w of branched C 18 carboxylic acids, amongst which there are linear C ⁇ 7 fatty acids substituted with a methyl group, for example in the position 8, 9 or 10, Cj 8 fatty acids of formula H-(CH 2 ) x -C 6 H 4 -(CH 2 ) y -
  • Table 2 Physical status of the perfumed softener bases after 15 days of storage
  • Softener 1 A softener (referenced as Softener 1) was obtained by admixing the following ingredients:
  • Stepantex ® VK90 is a product from Stepan Ltd.
  • Softener 2 Another softener (referenced as Softener 2) and containing an anti-gel ingredient according to the invention was obtained by admixing the following ingredients:

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Fats And Perfumes (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne un dérivé d'ester d'amine quaternisé qui est utilisé comme ingrédient de régulation de la viscosité ou d'anti-gélification dans des articles d'assouplissage, notamment, un produit assouplissant. Ce dérivé d'ester d'amine quaternisé est un composé dérivé de 3-(dialkylamino)-1,2-propanédiol et d'un acide gras non linéaire, tel qu'un acide isostéarique.
PCT/IB2003/001970 2002-05-13 2003-05-13 Derives d'acides gras ramifies en tant qu'ingredients de regulation de la viscosite ou d'anti-gelification WO2003095601A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP03720814A EP1506275A1 (fr) 2002-05-13 2003-05-13 Derives d'acides gras ramifies en tant qu'ingredients de regulation de la viscosite ou d'anti-gelification
US10/988,016 US20050176609A1 (en) 2002-05-13 2004-11-12 Branched fatty acid derivatives as anti-gelling or viscosity-control ingredients

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IB0201661 2002-05-13
IBPCT/IB02/01661 2002-05-13

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US10/988,016 Continuation US20050176609A1 (en) 2002-05-13 2004-11-12 Branched fatty acid derivatives as anti-gelling or viscosity-control ingredients

Publications (1)

Publication Number Publication Date
WO2003095601A1 true WO2003095601A1 (fr) 2003-11-20

Family

ID=29415741

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2003/001970 WO2003095601A1 (fr) 2002-05-13 2003-05-13 Derives d'acides gras ramifies en tant qu'ingredients de regulation de la viscosite ou d'anti-gelification

Country Status (2)

Country Link
EP (1) EP1506275A1 (fr)
WO (1) WO2003095601A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2691503B1 (fr) 2011-03-30 2018-08-15 The Procter and Gamble Company Compositions de soins des tissus comprenant des agents de stabilité initiale

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992008837A2 (fr) * 1990-11-16 1992-05-29 Akzo N.V. Adoucissants biodegradables pour tissus
US5422021A (en) * 1989-09-19 1995-06-06 Lever Brothers Company, Division Of Conopco, Inc. Fabric softening
US5474690A (en) * 1994-11-14 1995-12-12 The Procter & Gamble Company Concentrated biodegradable quaternary ammonium fabric softener compositions containing intermediate iodine value fatty acid chains
JPH08245527A (ja) * 1995-03-16 1996-09-24 Kao Corp 新規な第４級アンモニウム塩及びその製造法
JPH1072772A (ja) * 1996-08-26 1998-03-17 Kao Corp 衣料用色調変化抑制剤組成物
JPH10183468A (ja) * 1996-12-18 1998-07-14 Kao Corp 衣料用柔軟仕上剤組成物

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5422021A (en) * 1989-09-19 1995-06-06 Lever Brothers Company, Division Of Conopco, Inc. Fabric softening
WO1992008837A2 (fr) * 1990-11-16 1992-05-29 Akzo N.V. Adoucissants biodegradables pour tissus
US5474690A (en) * 1994-11-14 1995-12-12 The Procter & Gamble Company Concentrated biodegradable quaternary ammonium fabric softener compositions containing intermediate iodine value fatty acid chains
JPH08245527A (ja) * 1995-03-16 1996-09-24 Kao Corp 新規な第４級アンモニウム塩及びその製造法
JPH1072772A (ja) * 1996-08-26 1998-03-17 Kao Corp 衣料用色調変化抑制剤組成物
JPH10183468A (ja) * 1996-12-18 1998-07-14 Kao Corp 衣料用柔軟仕上剤組成物

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
PATENT ABSTRACTS OF JAPAN vol. 1997, no. 01 31 January 1997 (1997-01-31) *
PATENT ABSTRACTS OF JAPAN vol. 1998, no. 08 30 June 1998 (1998-06-30) *
PATENT ABSTRACTS OF JAPAN vol. 1998, no. 12 31 October 1998 (1998-10-31) *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2691503B1 (fr) 2011-03-30 2018-08-15 The Procter and Gamble Company Compositions de soins des tissus comprenant des agents de stabilité initiale
EP2691503B2 (fr) † 2011-03-30 2021-08-11 The Procter & Gamble Company Compositions de soins des tissus comprenant des agents de stabilité initiale

Also Published As

Publication number Publication date
EP1506275A1 (fr) 2005-02-16

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