EP2294168B1 - Améliorations associées aux adoucissants textiles - Google Patents

Améliorations associées aux adoucissants textiles Download PDF

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Publication number
EP2294168B1
EP2294168B1 EP09757364A EP09757364A EP2294168B1 EP 2294168 B1 EP2294168 B1 EP 2294168B1 EP 09757364 A EP09757364 A EP 09757364A EP 09757364 A EP09757364 A EP 09757364A EP 2294168 B1 EP2294168 B1 EP 2294168B1
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EP
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Prior art keywords
fatty
sucrose
use according
ester
quaternary ammonium
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EP09757364A
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German (de)
English (en)
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EP2294168A1 (fr
Inventor
Mansur Sultan Mohammadi
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Unilever PLC
Unilever NV
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Unilever PLC
Unilever NV
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Priority to PL09757364T priority Critical patent/PL2294168T3/pl
Priority to EP09757364A priority patent/EP2294168B1/fr
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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
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/835—Mixtures of non-ionic with cationic 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
    • C11D3/0005—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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/22—Carbohydrates or derivatives thereof
    • C11D3/221—Mono, di- or trisaccharides or derivatives 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
    • 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

Definitions

  • the present invention concerns the use of sugar esters to reduce and eliminate fatty base off-odours in fabric conditioner compositions which contain actives having unsaturated fatty chains.
  • So-called 'soft' fabric softening actives derived from unsaturated fatty acyl or acid feedstock have the advantages of ease of formulation and manufacture and a greater physical stability under varying climatic storage conditions, when compared to the so-called 'hardened' softeners (i.e. those derived from fully or nearly fully saturated fatty compounds).
  • Perfume ingredients have been used to counteract the malodours generated on different substrates.
  • WO 2008/026140 A2 uses malodour counteracting mixtures of perfume ingredients containing at least one nitrile material in combination with another fragrance material to neutralise tobacco, bathroom or kitchen malodours, animal malodours, etc in a variety of products including textile treatment products such as fabric softeners.
  • WO 2006/058297 A1 uses perfume compositions for masking fatty acid odours in a range of cleaning and treatment compositions including laundry and dishwashing detergents, particularly those odours arising from enzyme-generated short chain fatty acids such as butyric acid.
  • WO 2006/066705 A1 (Unilever), describes a malodour reducing toilet bar composition comprising a pyranone derivative.
  • Use of pyran-4-one derivates as a specific odour masking agent in toilet bars enables the inclusion of reduced levels of perfume in the bar composition.
  • US 2004/220064 is concerned with imparting fragrance perception to a product and a substrate, such as dry fabric or hair. It discloses a fragrance delivery vehicle comprising a water insoluble oil, a conditioner containing > 0.5 wt % of a cationic active and at least 0.1 wt % of a fragrance composition comprising specific aroma chemicals.
  • Example 1 B discloses a softener composition comprising RYOTO ER290 in combination with HEQ derived from hardened tallow.
  • WO 01/46361 discloses compositions comprising (i) cationic softening compounds having two or more alkyl or alkenyl chains of at least C8 chain length, (ii) at least one oily sugar derivative and (iii) a deposition aid, which comprises a mixture of nonionic surfactant(s) and cationic polymer(s).
  • Tables 3 and 4 disclose compositions comprising RYOTO ER290 and unsaturated di(tallowoyloxyethyl) dimethyl ammonium chloride.
  • WO 01/92447 discloses fabric conditioner compositions having defined viscosity properties, comprising a cationic fabric softener and a fatty acid partial ester of a polyhydric alcohol.
  • Example 6 discloses Tetranyl AT-7590, which is a triethanolamine quaternary ammonium compound derived from partially saturated tallow having an iodine value of 34, in combination with ER290 (sucrose tetraerucate).
  • WO 02/04587 discloses a process for conditioning and fragrancing a substrate, which includes contacting a fragrance delivery vehicle containing a water insoluble oil, a cationic active, and at least 0.1 wt % of a fragrance composition with a substrate in an aqueous solution.
  • the examples disclose compositions comprising HEQ (dialkylyloxy dimethyl ammonium chloride, where the alkyl is hardened tallow) and SPE (Ryoto ER290).
  • WO 03/087286 discloses a heat activated fabric treatment composition for use in a tumble dryer.
  • the composition comprises a fabric treatment active, water, oil, which may be an oily sugar ester compound and an optional non-ionic surfactant.
  • Example 10 discloses a composition comprising a tallow based TEA quat with an IV of about 35 and the sugar ester oil Emnon SCR-PK.
  • WO 97/15651 discloses an aqueous fabric softening composition
  • aqueous fabric softening composition comprising (a) a water insoluble quaternary ammonium compound comprising at least one ester link and two C12-28 alkyl or alkenyl groups, and (b) a sucrose ester or alkyl polyglucoside.
  • Compositions comprising HEQ and sucrose esters of the Crodesta series are exemplified.
  • SPEs have been used as fabric softeners and are known as principle softeners, as co-softeners and as stabilisers.
  • sucrose ester to reduce base off-odour in a composition
  • a sucrose ester is defined by the formula (I): M(OH) 8-x (OC(O)R') x
  • M(OH) 8 is sucrose in which M is the main backbone of the sucrose and (OH) represents the available hydroxyl groups on a sucrose molecule
  • x is an integer selected from 1 to 8, preferably 4
  • R' is a fatty chain and is linear or branched, cyclic or acyclic, saturated or unsaturated, substituted or unsubstituted and is independently selected from (C 8 -C 18 ) and (C 20 -C 22 ) with the proviso that, when R' is C 8 -C 18 , the iodine value of the fatty chains is from 0 to 25, preferably 0 to 20, more
  • Further aspects of the invention provide for the use of a sugar ester in a composition to improve freshness of laundered articles, to improve clean smell of laundered articles and to improve the longevity of fragrance of a laundry conditioning product.
  • Sucrose ester is composed of a sucrose moiety having one or more of its hydroxyl groups esterified.
  • Sucrose is a disaccharide.
  • the sucrose molecule can be represented by the formula: M(OH) 8 wherein M is the disaccharide backbone and there are a total of 8 hydroxyl groups in the molecule.
  • a suitable sucrose ester can be represented by the following formula (I): M(OH) 8-x (OC(O)R') x formula (I) wherein, M(OH) 8 is sucrose in which M is the main backbone of the sucrose and (OH) represents the available hydroxyl groups on a sucrose molecule; x is an integer selected from 1 to 8, preferably 4 and is the hydroxyl groups that are esterified and (8-x) is the hydroxyl groups that remain unchanged; R' is a fatty chain and is linear or branched, cyclic or acyclic, saturated or unsaturated, substituted or unsubstituted.
  • Substituent groups can include, for example, hydroxyl, halide, alkoxy, and the like.
  • R' is independently selected from (C 8 -C 18 , preferably (C 12 -C 18 ) and (C 20 -C 22 ) with the proviso that, when R' is C 8 -C 18 , the iodine value of the fatty chains is from 0 to 25, preferably 0 to 20, more preferably from 1 to 5, most preferably from 1 to 2; and when R' is C 20 -C 22 , the iodine value of the fatty chains is from 0 to 120, preferably, from 20 to 100, more preferably from 25 to 90, most preferably from 25 to 80.
  • a mixture of chains may be used in the SPE.
  • the sucrose ester is preferably solid, or substantially solid in nature, and has an iodine value of from 0 to 15, preferably from 0 to 10, more preferably from 0 to 5 and most preferably from 1 to 5.
  • compositions are preferably substantially free and more preferably free from the presence of SPEs that do not conform to the formula (I) given above.
  • the unsaturated R' moieties may comprise a mixture of "cis” and “trans” forms about the unsaturated sites.
  • the "cis” / "trans” ratios may range from about 1:1 to about 50:1, or from about 2:1 to about 40:1, or from about 3:1 to about 30:1, or from about 4:1 to about 20: 1.
  • the sucrose ester is present in compositions comprising a quaternary ammonium compound having unsaturated fatty chains, at a level of from 0.1 to 5, preferably from 0.2 to 4.5, more preferably from 0.2 to 4 % by weight of the total composition.
  • a particularly preferred range is from 0.1 to 4 %, preferably from 0.2 to 3 %, more preferably from 0.5 to 2 %, even more preferably from 0.6 to 1.5 %.
  • the SPEs are preferably tallow or plant or vegetable based.
  • Preferred plant and vegetable based SPEs include those derived from palm, canola, high erucate rape and soya bean.
  • sucrose esters are the Ryoto range (ex Mitsubishi) of liquid, soft solid or solid from and fully or partially hardened sucrose esters based on vegetable oils.
  • sucrose ester is SCR-PK-H (ex Kao), which is derived from hardened palm kernel oil with a chain length of C 16 and mainly C 18 .
  • the present invention relates to quaternary ammonium compounds having unsaturated chains.
  • Such compounds are typically derived from fatty acyl or fatty acid feed stock having an Iodine Value of from 20 to 140, preferably from 20 to 60, more preferably from 20 to 50, most preferably from 25 to 45.
  • the unsaturated chains come from the unsaturated fatty feed stock.
  • the iodine value represents the mean iodine value of the parent fatty acyl compounds or fatty acids of all of the quaternary ammonium materials present.
  • the iodine value represents the mean iodine value of the parent fatty acyl compounds or fatty acids of all of the quaternary ammonium materials present.
  • Such compounds have a strong base odour of parent fatty compound such as tallow or oily smells from other plant sources such as palm.
  • High IV softener materials hence require odour masking perfume and increased perfume levels which this invention circumvents.
  • Iodine value is defined as the number of grams of iodine absorbed per 100 g of test material. NMR spectroscopy is a suitable technique for determining the iodine value of the softening agents of the present invention, using the method described in Anal. Chem., 34, 1136 (1962) by Johnson and Shoolery and in EP 593,542 (Unilever, 1993).
  • the quaternary ammonium compound is preferably present in the compositions suitable for use in the invention at a level of from 2 % to 55 %, preferably from 3 % to 50 %, more preferably from 4 % to 40 % preferably from 5 % to 25 %, by weight of the total composition, for example from 6 to 20 % by weight.
  • the quaternary ammonium compound may be present at a level of greater than 80 %, preferably 90 % by weight of the total composition.
  • the preferred quaternary ammonium fabric conditioner for use in compositions suitable for use in the present invention are the so called "ester quats”.
  • Particularly preferred materials are the ester-linked triethanolammonium (TEA) quaternary ammonium compounds comprising a mixture of mono-, di- and tri-ester linked components.
  • TAA triethanolammonium
  • such TEA-based fabric softening compounds comprise a mixture of mono, di- and tri-ester forms of the compound.
  • the di-ester linked component comprises no more than 70 % by weight of the fabric softening compound, preferably no more than 60 %, e.g. no more than 55 %, or even no more than 45 % of the fabric softening compound and at least 10 % of the monoester linked component.
  • a first group of quaternary ammonium compounds (QACs) suitable for use in the present invention is represented by formula (I): [(CH 2 ) n (TR)] m -(R 1 ).N + -(CH 2 ) n (OH)] 3-m X - (I) wherein each R is independently selected from a C 5-35 alkyl or alkenyl group; R 1 represents a C 1-4 alkyl, C 2-4 alkenyl or a C 1-4 hydroxyalkyl group; T is generally O-CO. (i.e. an ester group bound to R via its carbon atom), but may alternatively be CO.O (i.e.
  • TEA ester quats preparations which are rich in the di-esters of triethanolammonium methylsulphate, otherwise referred to as "TEA ester quats".
  • TetranylTM ex Kao TetranylTM ex Kao, AT-1 (di-[tallow ester] of triethanolammonium methylsulphate), and L5/90 (di-[palm ester] of triethanolammonium methylsulphate), both ex Kao, and RewoquatTM WE15 (a di-ester of triethanolammonium methylsulphate having fatty acyl residues deriving from C 10 -C 20 and C 16 -C 18 unsaturated fatty acids), ex Witco Corporation and the Stepantex (ex Stepan) soft range, Stepantex VT90, VA90 and SP90.
  • a second group of quaternary ammonium compounds suitable for use in the invention is represented by formula (II): (R 1 ) 3 N + -(CH 2 ) n -CH.(CH 2 TR 2 )-TR 2 X - (II) wherein each R 1 group is independently selected from C 1-4 alkyl, hydroxyalkyl or C 2-4 alkenyl groups; and wherein each R 2 group is independently selected from C 8-28 alkyl or alkenyl groups; and wherein n, T, and X - are as defined above.
  • Preferred materials of this second group include 1,2 bis[tallowoyloxy]-3-trimethylammonium propane chloride, 1,2 and 1,2-bis[oleoyloxy]-3-trimethylammonium propane chloride. Such materials are described in US 4,137,180 (Lever Brothers). Preferably, these materials also comprise an amount of the corresponding mono-ester.
  • a third group of quaternary ammonium compounds suitable for use in the invention is represented by formula (III): (R 1 ) 2 -N + -[(CH 2 ) n -T-R 2 ] 2 X - (III) wherein each R 1 group is independently selected from C 1-4 alkyl, or C 2-4 alkenyl groups; and wherein each R 2 group is independently selected from C 8-28 alkyl or alkenyl groups; and n, T, and X - are as defined above.
  • Preferred materials of this third group include bis(2-tallowoyloxyethyl)dimethyl ammonium chloride.
  • compositions for use in the invention are preferably free from perfume.
  • the malodour reducing effect of the sugar esters are such that perfume is not required to mask the malodour.
  • compositions of the invention are preferably free from perfume.
  • the malodour reducing effect of the sugar esters are such that perfume is not required to mask the malodour.
  • Useful components of the perfume include materials of both natural and synthetic origin. They include single compounds and mixtures. Specific examples of such components may be found in the current literature, e.g., in Fenaroli's Handbook of Flavor Ingredients, 1975, CRC Press ; Synthetic Food Adjuncts, 1947 by M. B. Jacobs, edited by Van Nostr and; or Perfume and Flavor Chemicals by S. Arctander 1969, Montclair, N.J. (USA ).
  • perfume in this context is not only meant a fully formulated product fragrance, but also selected components of that fragrance, particularly those which are prone to loss, such as the so-called 'top notes'.
  • Top notes are defined by Poucher (Journal of the Society of Cosmetic Chemists 6(2):80 [1955 ]). Examples of well known top-notes include citrus oils, linalool, linalyl acetate, lavender, dihydromyrcenol, rose oxide and cis-3-hexanol. Top notes typically comprise 15-25%wt of a perfume composition and in those embodiments of the invention which contain an increased level of top-notes it is envisaged at that least 20%wt would be present within the encapsulate.
  • perfume or pro-fragrance may be encapsulated, typical perfume components which it is advantageous to encapsulate, include those with a relatively low boiling point, preferably those with a boiling point of less than 300, preferably 100-250 Celsius and pro-fragrances which can produce such components.
  • perfume components which have a low Clog P (ie. those which will be partitioned into water), preferably with a Clog P of less than 3.0.
  • Clog P ie. those which will be partitioned into water
  • materials, of relatively low boiling point and relatively low Clog P have been called the "delayed blooming" perfume ingredients and include the following materials:
  • Preferred non-encapsulated perfume ingredients are those hydrophobic perfume components with a ClogP above 3.
  • ClogP means the logarithm to base 10 of the octanol/water partition coefficient (P).
  • the octanol/water partition coefficient of a PRM is the ratio between its equilibrium concentrations in octanol and water. Given that this measure is a ratio of the equilibrium concentration of a PRM in a non-polar solvent (octanol) with its concentration in a polar solvent (water), ClogP is also a measure of the hydrophobicity of a material--the higher the ClogP value, the more hydrophobic the material.
  • ClogP values can be readily calculated from a program called "CLOGP" which is available from Daylight Chemical Information Systems Inc., Irvine Calif., USA. Octanol/water partition coefficients are described in more detail in U.S. Pat. No. 5,578,563 .
  • Perfume components with a ClogP above 3 comprise: Iso E super, citronellol, Ethyl cinnamate, Bangalol, 2,4,6-Trimethylbenzaldehyde, Hexyl cinnamic aldehyde, 2,6-Dimethyl-2-heptanol, Diisobutylcarbinol, Ethyl salicylate, Phenethyl isobutyrate, Ethyl hexyl ketone, Propyl amyl ketone, Dibutyl ketone, Heptyl methyl ketone, 4,5-Dihydrotoluene, Caprylic aldehyde, Citral, Geranial, Isopropyl benzoate, Cyclohexanepropionic acid, Campholene aldehyde, Caprylic acid, Caprylic alcohol, Cuminaldehyde, 1-Ethyl-4-nitrobenzene, Heptyl formate, 4-I
  • compositions suitable for use in the present invention it is envisaged that there will be four or more, preferably five or more, more preferably six or more or even seven or more different perfume components from the list given of delayed blooming perfumes given above and/or the list of perfume components with a ClogP above 3 present in the perfume.
  • perfumes with which the present invention can be applied are the so-called 'aromatherapy' materials. These include many components also used in perfumery, including components of essential oils such as Clary Sage, Eucalyptus, Geranium, Lavender, Mace Extract, Neroli, Nutmeg, Spearmint, Sweet Violet Leaf and Valerian.
  • the SPEs for use in the invention described above can be used in encapsulated form along with perfume.
  • Co-softeners may be used. When employed, they are typically present at from 0.1 to 20% and particularly at from 0.5 to 10%, based on the total weight of the composition.
  • Preferred co-softeners include fatty esters, and fatty N-oxides.
  • Fatty esters that may be employed include fatty monoesters, such as glycerol monostearate, fatty sugar esters, such as those disclosed WO 01/46361 (Unilever).
  • compositions for use in the present invention will preferably comprise a fatty complexing agent.
  • suitable fatty complexing agents include fatty alcohols and fatty acids. Of these, fatty alcohols are most preferred.
  • the fatty complexing material improves the viscosity profile of the composition by complexing with mono-ester component of the fabric conditioner material thereby providing a composition which has relatively higher levels of di-ester and tri-ester linked components.
  • the di-ester and tri-ester linked components are more stable and do not affect initial viscosity as detrimentally as the mono-ester component.
  • compositions comprising quaternary ammonium materials based on TEA may destabilise the composition through depletion flocculation.
  • depletion flocculation is significantly reduced.
  • the fatty complexing agent at the increased levels as required by the present invention, "neutralises” the mono-ester linked component of the quaternary ammonium material. This in situ di-ester generation from mono-ester and fatty alcohol also improves the softening of the composition.
  • Preferred fatty acids include hardened tallow fatty acid (available under the trade name PristereneTM, ex Uniqema).
  • Preferred fatty alcohols include hardened tallow alcohol (available under the trade names StenolTM and HydrenolTM, ex Cognis and LaurexTM CS, ex Albright and Wilson).
  • the fatty complexing agent is preferably present in an amount greater than 0.3 to 5% by weight based on the total weight of the composition. More preferably, the fatty component is present in an amount of from 0.4 to 4%.
  • the weight ratio of the mono-ester component of the quaternary ammonium fabric softening material to the fatty complexing agent is preferably from 5:1 to 1:5, more preferably 4:1 to 1:4, most preferably 3:1 to 1:3, e.g. 2:1 to 1:2.
  • compositions may further comprise a nonionic surfactant, especially where the level of quaternary ammonium compound is above about 8 % by weight of the total composition. Typically these can be included for the purpose of stabilising the compositions.
  • Suitable nonionic surfactants include addition products of ethylene oxide and/or propylene oxide with fatty alcohols, fatty acids and fatty amines. Any of the alkoxylated materials of the particular type described hereinafter can be used as the nonionic surfactant.
  • Suitable surfactants are substantially water soluble surfactants of the general formula: R-Y- (C 2 H 4 O) z -CH 2 -CH 2 -OH where R is selected from the group consisting of primary, secondary and branched chain alkyl and/or acyl hydrocarbyl groups; primary, secondary and branched chain alkenyl hydrocarbyl groups; and primary, secondary and branched chain alkenyl-substituted phenolic hydrocarbyl groups; the hydrocarbyl groups having a chain length of from 8 to about 25, preferably 10 to 20, e.g. 14 to 18 carbon atoms.
  • Y is typically:
  • the nonionic surfactant has an HLB of from about 7 to about 20, more preferably from 10 to 18, e.g. 12 to 16.
  • GenapolTM C200 (Clariant) based on coco chain and 20 EO groups is an example of a suitable nonionic surfactant.
  • the nonionic surfactant is present in an amount from 0.01 to 10%, more preferably 0.1 to 5 by weight, based on the total weight of the composition.
  • Alternative stabilising agents may be used.
  • Alternative stabilisers include single long chain ethoxylated cationic surfactant with a counter ion which is preferably an alkyl sulphate, such as methyl sulphate and ethyl sulphate, and most preferably is a methylsulphate counter-ion.
  • the single long chain cationic surfactants alternatives are alkoxylated cationic quaternary ammonium surfactants.
  • Those suitable for use in this invention are generally derived from fatty alcohols, fatty acids, fatty methyl esters, alkyl substituted phenols, alkyl substituted benzoic acids, and/or alkyl substituted benzoate esters, and/or fatty acids that are converted to amines which can optionally be further reacted with another long chain alkyl or alkyl-aryl group; this amine compound is then alkoxylated with one or two alkylene oxide chains each having less than or equal to about 50 moles alkylene oxide moieties (e.g. ethylene oxide and/or propylene oxide) per mole of amine.
  • alkylene oxide moieties e.g. ethylene oxide and/or propylene oxide
  • Typical of this class are products obtained from the quaternization of aliphatic saturated or unsaturated, primary, secondary, or branched amines having one hydrocarbon chain from about 12 to about 22 carbon atoms alkoxylated with one or two alkylene oxide chains on the amine atom each having less than or equal to about 50 alkylene oxide moieties.
  • the amine hydrocarbons for use herein have from about 12 to about 22 carbon atoms, and are preferably in a straight chain configuration.
  • Suitable quaternary ammonium surfactants are made with one or two alkylene oxide chains attached to the amine moiety, in average amounts of less than or equal to about 50 moles of alkylene oxide per alkyl chain, more preferably from about 3 to about 20 moles of alkylene oxide, and most preferably from about 5 to about 12 moles of alkylene oxide per hydrophobic, e.g., alkyl group.
  • Suitable stabilizers of this type include Ethoquad® 18/25, C/25, and O/25 from Akzo and Variquat®-66 (soft tallow alkyl bis(polyoxyethyl) ammonium ethyl sulfate with a total of about 16 ethoxy units) from Goldschmidt.
  • Preferred commercial surfactants include Tomah QC-15, cocopoly (15) oxyethylene methyl ammonium chloride (ex Tomah Products); and Rewoquat CPEM, coco pentaethoxymethyl ammonium methosulphate (ex Witco).
  • Preferred commercial surfactants include Rewoquat V3351, a tallow alkyl amido-amine methyl sulphate quat (ex Goldschmidt), Surfac ARF, a tallow amine ethoxy ammonium methyl sulphate (ex Surfachem).
  • amido-amine single long chain cationic surfactants for use in the present invention may be alkoxylated.
  • These alkoxylated amido-amine single chain cationic surfactants comprise one or more alkylene oxide chains each having less than or equal to about 50 moles alkylene oxide moieties (e.g. ethylene oxide and/or propylene oxide) per mole of amine.
  • the preferred alkoxylated surfactants for use in the present invention comprise at least one ethoxylate group.
  • compositions for use in the invention may contain one or more other ingredients.
  • ingredients include photobleaches, fluorescent agents, dyes, preservatives (e.g. bactericides), pH buffering agents, perfume carriers, hydrotropes, anti-redeposition agents, soil-release agents, polyelectrolytes, anti-shrinking agents, anti-wrinkle agents, anti-oxidants, sunscreens, anti-corrosion agents, drape imparting agents, anti-static agents and ironing aids.
  • the products of the invention preferably contain pearlisers and/or opacifiers.
  • cationic polymeric deposition aids include cationic guar polymers such as JaguarTM (ex Rhone Poulenc), cationic cellulose derivatives such as CelquatsTM (ex National Starch), FlocaidTM (ex National Starch), cationic potato starch such as SoftGelTM (ex Aralose), cationic polyacrylamides such as PCG (ex Allied Colloids).
  • a composition for use in the invention may be in dry solid or liquid form.
  • the composition may be a concentrate to be diluted, rehydrated and/or dissolved in a solvent, including water, before use.
  • the composition may also be a ready-to-use (in-use) composition.
  • the composition is provided as a ready to use liquid comprising an aqueous phase.
  • the aqueous phase may comprise water-soluble species, such as mineral salts or short chain (C 1-4 ) alcohols.
  • the mineral salts may aid the attainment of the required phase volume for the composition, as may water soluble organic salts and cationic deflocculating polymers, as described in EP 41,698 A2 (Unilever). Such salts may be present at from 0.001 to 1% and preferably at from 0.005 to 0.1% by weight of the total composition. Examples of suitable mineral salts for this purpose include calcium chloride and magnesium chloride.
  • the compositions of the invention may also contain pH modifiers such as hydrochloric acid.
  • the short chain alcohols include primary alcohols, such as ethanol, propanol, and butanol, and secondary alcohols such as isopropanol. The short chain alcohol may be added with the cationic softening agent during the preparation of the composition.
  • the composition is preferably a fabric softener or fabric conditioner composition, and is preferably for use in the rinse cycle of a home textile laundering operation, where, it may be added directly in an undiluted state to a washing machine, e.g. through a dispenser drawer or, for a top-loading washing machine, directly into the drum. Alternatively, it can be diluted prior to use.
  • the compositions may also be used in a domestic hand-washing laundry operation.
  • compositions used in the invention are not detergent compositions and are preferably substantially free (for example having less than 0.1 weight %, preferably less than 0.05 weight % by weight of the total composition), more preferably free from one or more detersive surfactants such as anionic, ampholytic, zwitterionic surfactants, and cleaning soaps.
  • compositions for use in the present invention can be used in industrial laundry operations, e.g. as a finishing agent for softening new clothes prior to sale to consumers.
  • the cationic softening agent and SPE, and any optional components such as co-softener or complexing agent are heated together until a co-melt is formed. Water and other components are heated and the co-melt is added to the water with stirring.
  • SPE SPE
  • Alternative methods of addition for the SPE will be to post dose it at the end of the process, as is, or as an emulsion. If the SPE is solid the batch temperature should be above its melting point for its emulsification by the softener active.
  • Example 1 Preparation of Compositions 4-7, Comparative Examples 1-3 and Control A
  • Compositions 4-7, Comparative Examples 1-3 and Control A were prepared in a bench top mixer equipped with a top 3-stage stirrer and a recirculation bath for temperature control.
  • the quaternary softening agent, SPE, and complexing agent were heated together until a co-melt was formed. Water was heated and the co-melt added to the water with stirring. The batch was cooled to room temperature.
  • THSBO Clariant
  • Clariant is a pure sucrose polyester based on touch hardened soya bean oil.
  • ER290 (ex Mitsubishi) is a food grade pure sucrose polyester based on C22:1 erucic acid.
  • SCR-PK-H (ex KAO) is a sucrose polyester derived from hardened palm kernel oil (C16 and mainly C18) and contains about 20% impurities mainly fatty acids and soaps as specified in WO2006/076952 A1 (Unilever).
  • composition of Compositions 4-7, Comparative Examples 1-3 and Control A are given in Table 1 below.
  • Table 1 Composition of Compositions 4-7, Comparative Examples 1-3 and Control A Component Control Comparative Examples Compositions A 1 2 3 4 5 6 7 Stepantex VT90 4.4 4 3.4 3 4 3.4 4 3.4 Stenol 16/18 L 0.48 0.48 0.48 0.48 0.48 0.48 0.48 THSBO 0 0.4 1 1.4 0 0 0 0 ER290 0 0 0 0 0 0.4 1 0 0 SCR-PK-H 0 0 0 0 0 0 0.4 1 demineralised water to 100 to 100 to 100 to 100 to 100 to 100 to 100 to 100 to 100 to 100 to 100 to 100 to 100 to 100 to 100 to 100
  • Stepantex VT90 is a soft tallow TEA quaternary ammonium softening compound containing 90 % active and 10 % IPA.
  • Stenol 16/18 L is a fatty alcohol (complexing agent) with a mixture of C16 and C18 saturated chains.
  • Table 2 gives the ester distributions of the ER290 and SCR-PK sucrose polyesters used in these examples.
  • Table 2 Ester distribution in ER290 and SCR-PK sucrose polyesters Sucrose polyester Mono- di- Tri- Tetra- Penta- Hexa- Hepta- Octa- ER290 0 5 17.5 19.1 20.5 20.3 10.8 3.8 SCR-PK 0 3.2 14.6 27.5 24.6 10.1 9.0 2.9
  • Table 3 gives the level of unsaturation and the odour description of the quaternary ammonium compound VT90.
  • Table 3 Chain distribution and odour description of VT90.
  • Softener material Odour description C10 C12 C14 C14 uns C16 C16:1 C18 C18:1 C18: 2 VT90 Fatty/ tallow 0.1 0.1 2.7 0.3 30.6 2.2 32.6 28.6 2.8
  • sucrose polyesters The odour of sucrose polyesters was as follows:-
  • Example 2 Evaluation of the base odour from Comparative Examples 1-3
  • Terry towelling monitors measuring about 20 x 20 cm were desized by twice washing in a washing machine at 90 °C. Sets of two monitors were placed in Tergo pots with 1 litre of demineralised water per pot and agitated for 10 minutes.
  • the Tergos were dosed with the formulations in the amounts shown in Table 3 below and allowed to agitate for a further 15 minutes. The monitors were then removed and spinned and line dried.
  • Table 4 shows the amount of product used in each treatment to equalise the amount of VT90 deposited on the monitors.
  • Table 4 Product dosage in Tergo-to-meters and the level of VT90 and sucrose polyester deposited per monitor for Comparative Example A and Compositions 1-3.
  • a 1 2 3 Product dose/g 2.0 2.28 2.50 2.93 VT90g/monitor 0.044 0.044 0.044 0.044 Sucrose polyester g/monitor 0.0 0.004 0.012 0.020
  • the monitors were line dried for three days. Then one monitor of each set was presented to an expert panel for odour evaluation whilst the other was kept in a bottle under fluorescent light (for build-up of odour).
  • the odour descriptors used were based on those known in the art.
  • the panel members described the odour and assigned a number to quantify the intensity of the odour they perceived. Table 5 summarises the outcome of this evaluation. Table 5.
  • a 1 2 3 Odour score 1.2 1.5 1.3 1.4 Odour quality Fatty Fatty, oily Fatty, oily Fatty, oily Fatty, oily Fatty, oily
  • the panel results show that there is very little difference between Compositions 1-3 and Control A. There was a directional worsening of the smell in presence of soyabean sucrose polyester and the rancid smell of oil was noticed by the panel.
  • Table 6 The product dosage in Tergo-to-meters and the level of VT90 and sucrose polyesters deposited per monitor. A 4 5 6 7 Product dose/g 2.00 2.29 2.59 2.29 2.59 VT90 g/monitor 0.044 0.044 0.044 0.044 0.044 ER290 g/monitor 0.000 0.004 0.013 0.004 0.013
  • the monitors were line dried and on the first day one set presented to the panel and another set stored in bottles for later evaluation.
  • Table 6 summarises the odour quality and scores.
  • Table 7. Average (of 8 panellists) odour intensity and odour quality of day 1 of treated monitors.
  • a 4 5 6 7 Odour score 1.3 0.2 0.2 0.3 0.2 Odour quality Fatty, stale Clean, fresh Clean, fresh Clean, fresh Clean, fresh Clean, fresh A hint sweet
  • sucrose esters have efficiently suppressed the base odour of the soft tallow active on the monitors.
  • the monitors with sucrose polyesters in accordance with the invention have reduced the base odour efficiently and have a clean smell.
  • the monitors with SCR-PK-H were surprisingly preferred by the panel for softness.

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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)
  • Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Emergency Medicine (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Detergent Compositions (AREA)

Claims (11)

  1. Utilisation d'un ester de saccharose pour réduire une odeur atypique de base dans une composition comprenant un composé d'ammonium quaternaire ayant des chaînes grasses insaturées ; dans laquelle l'ester de saccharose est défini par la formule (I) :

            M(OH)8-x (OC(O)R')x

    dans laquelle M(OH)8 est un saccharose dans lequel M est la chaîne principale du saccharose et (OH) représente les groupes hydroxyles disponibles sur une molécule de saccharose ; x est un nombre entier choisi parmi les nombres allant de 1 à 8, de préférence 4 ; R' est une chaîne grasse et est linéaire ou ramifié, cyclique ou acyclique, saturé ou insaturé ; substitué ou non substitué et est indépendamment choisi entre (C8-C18) et (C20-C22) à la condition que, lorsque R' est en C8-C18, l'indice d'iode des chaînes grasses soit de 0 à 25, de préférence de 0 à 20, de manière davantage préférée de 1 à 5 ; et que lorsque R' est en C20-C22, l'indice d'iode des chaînes grasses soit de 0 à 120, de préférence, de 20 à 100, de manière préférée entre toutes, de 25 à 80.
  2. Utilisation selon la revendication 1, dans laquelle R' est en C8-C18 et l'indice d'iode des chaînes grasses est de 0 à 15.
  3. Utilisation selon la revendication 1 ou la revendication 2, dans laquelle l'ester de saccharose est solide et a un indice d'iode allant de 0 à 10, de préférence, de 0 à 5.
  4. Utilisation selon l'une quelconque des revendications précédentes, dans laquelle le composé d'ammonium quaternaire est dérivé de matières premières d'alimentation grasses ayant un indice d'iode de 20 à 140, de préférence de 20 à 60, de manière davantage préférée, de 20 à 50, de manière préférée entre toutes, de 25 à 45.
  5. Utilisation selon l'une quelconque des revendications précédentes, dans laquelle l'ester de saccharose est présent à un niveau de 0,1 à 5, de préférence, de 0,2 à 4,5, de manière davantage préférée, de 0,2 à 4 % en poids de la composition totale.
  6. Utilisation selon l'une quelconque des revendications précédentes, dans laquelle l'ester de saccharose est dérivé d'une source choisie dans le groupe constitué par la suif, les plantes et les légumes.
  7. Utilisation selon l'une quelconque des revendications précédentes, dans laquelle le composé d'ammonium quaternaire est un composé d'ammonium quaternaire à liaison ester à base de triéthanolammonium (TEA).
  8. Utilisation selon l'une quelconque des revendications précédentes, dans laquelle le composé d'ammonium quaternaire est présent à un niveau de 3 à 50 %, de préférence, de 4 à 40 %, de manière davantage préférée, de 5 à 25 % en poids de la composition totale.
  9. Utilisation selon l'une quelconque des revendications précédentes, dans laquelle la composition comprend en outre un agent complexant gras.
  10. Utilisation selon l'une quelconque des revendications précédentes, dans laquelle la composition comprend en outre au moins un parfum.
  11. Utilisation selon la revendication 10, dans laquelle le parfum est présent à un niveau allant de 0,01 à 10 % en poids de la composition totale.
EP09757364A 2008-06-05 2009-04-24 Améliorations associées aux adoucissants textiles Not-in-force EP2294168B1 (fr)

Priority Applications (2)

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PL09757364T PL2294168T3 (pl) 2008-06-05 2009-04-24 Ulepszenia dotyczące kompozycji do kondycjonowania tkanin
EP09757364A EP2294168B1 (fr) 2008-06-05 2009-04-24 Améliorations associées aux adoucissants textiles

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP08157635 2008-06-05
PCT/EP2009/054956 WO2009146981A1 (fr) 2008-06-05 2009-04-24 Améliorations se rapportant à des produits assouplissants pour tissus
EP09757364A EP2294168B1 (fr) 2008-06-05 2009-04-24 Améliorations associées aux adoucissants textiles

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AR (1) AR071932A1 (fr)
BR (1) BRPI0914903A2 (fr)
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BR112014013945A2 (pt) * 2011-12-16 2017-06-13 Unilever Nv composiçãos detergente para lavar roupa e processo para tratar tecido
JP2024517798A (ja) 2021-05-04 2024-04-23 ニュートリション・アンド・バイオサイエンシーズ・ユーエスエー・フォー，インコーポレイテッド 不溶性アルファ－グルカンを含む組成物
EP4370560A1 (fr) 2021-07-13 2024-05-22 Nutrition & Biosciences USA 4, Inc. Dérivés d'ester de glucane cationique
WO2023081341A1 (fr) 2021-11-05 2023-05-11 Nutrition & Biosciences USA 4, Inc. Compositions comprenant un dérivé d'alpha-1,6-glucane cationique et un alpha-1,3-glucane
WO2023114942A1 (fr) 2021-12-16 2023-06-22 Nutrition & Biosciences USA 4, Inc. Compositions comprenant des éthers d'alpha-glucane cationiques dans des solvants organiques polaires aqueux
WO2024015769A1 (fr) 2022-07-11 2024-01-18 Nutrition & Biosciences USA 4, Inc. Dérivés amphiphiles d'ester de glucane
WO2024081773A1 (fr) 2022-10-14 2024-04-18 Nutrition & Biosciences USA 4, Inc. Compositions comprenant de l'eau, un éther d'alpha-1,6-glucane cationique et un solvant organique

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Publication number Priority date Publication date Assignee Title
GB9114540D0 (en) 1991-07-05 1991-08-21 Unilever Plc Fabric softening composition
GB9521667D0 (en) 1995-10-23 1996-01-03 Unilever Plc Fabric softening composition
GB9930435D0 (en) 1999-12-22 2000-02-16 Unilever Plc Fabric softening compositions
GB0012958D0 (en) 2000-05-26 2000-07-19 Unilever Plc Fabric conditioning composition
WO2002004587A1 (fr) 2000-07-07 2002-01-17 Givaudan S.A. Procede conçu pour conferer une perception de conditionnement et de parfum agreable aux tissus humides et secs
US20020055452A1 (en) 2000-07-07 2002-05-09 Givaudan Sa Process for imparting a fragrance to a product and fragrance and conditioning to a dry fabric
GB0208695D0 (en) 2002-04-16 2002-05-29 Unilever Plc Fabric treatment composition
EP1661977A1 (fr) 2004-11-29 2006-05-31 The Procter & Gamble Company Compositions de lavage
US7015179B1 (en) 2004-12-22 2006-03-21 Unilever Home & Personal Care Usa Reduced odor toilet bar composition
WO2007078782A1 (fr) 2005-12-15 2007-07-12 The Procter & Gamble Company Compositions pour l'entretien des textiles ayant un effet adoucissant, antistatique et parfume
DE102006040276A1 (de) 2006-08-17 2008-02-21 Technische Universität Dresden Verwendung von Mono- oder Disacchariden zur Maskierung von Gerüchen sowie Verfahren und Zusammensetzung zur Maskierung von Gerüchen
EP2059265B1 (fr) 2006-08-28 2018-10-17 Firmenich S.A. Compositions réduisant les mauvaises odeurs et procédé de leur utilisation

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CN102057027B (zh) 2013-04-10
CN102057027A (zh) 2011-05-11
EP2294168A1 (fr) 2011-03-16
AR071932A1 (es) 2010-07-28
ES2398622T3 (es) 2013-03-20
WO2009146981A1 (fr) 2009-12-10
PL2294168T3 (pl) 2013-05-31
ZA201007840B (en) 2012-02-29
BRPI0914903A2 (pt) 2015-10-20

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