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WO1998016538A1 - Composition adoucissant les tissus - Google Patents

Composition adoucissant les tissus Download PDF

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Publication number
WO1998016538A1
WO1998016538A1 PCT/EP1997/005762 EP9705762W WO9816538A1 WO 1998016538 A1 WO1998016538 A1 WO 1998016538A1 EP 9705762 W EP9705762 W EP 9705762W WO 9816538 A1 WO9816538 A1 WO 9816538A1
Authority
WO
WIPO (PCT)
Prior art keywords
fabric softening
cpe
softening composition
rse
composition according
Prior art date
Application number
PCT/EP1997/005762
Other languages
English (en)
Inventor
David Stephen Grainger
Abid Nadim Khan-Lodhi
Original Assignee
Unilever Plc
Unilever N.V.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Unilever Plc, Unilever N.V. filed Critical Unilever Plc
Priority to BR9711906A priority Critical patent/BR9711906A/pt
Priority to EP97913161A priority patent/EP0934328A1/fr
Priority to EA199900383A priority patent/EA001695B1/ru
Priority to AU50510/98A priority patent/AU723907B2/en
Publication of WO1998016538A1 publication Critical patent/WO1998016538A1/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
    • 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
    • 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
    • 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
    • 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
    • C11D1/662—Carbohydrates or derivatives
    • 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
    • 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
    • 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
    • C11D3/222—Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin
    • C11D3/227—Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin with nitrogen-containing groups
    • 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
    • C11D3/37—Polymers
    • C11D3/3746—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3769—(Co)polymerised monomers containing nitrogen, e.g. carbonamides, nitriles or amines
    • 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
    • C11D3/37—Polymers
    • C11D3/3746—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3769—(Co)polymerised monomers containing nitrogen, e.g. carbonamides, nitriles or amines
    • C11D3/3773—(Co)polymerised monomers containing nitrogen, e.g. carbonamides, nitriles or amines in liquid compositions

Definitions

  • the present invention relates to fabric softening compositions .
  • the invention relates to fabric softening compositions that soften fabrics without affecting the absorbency of the fabric.
  • Co-pending application GB 9518012.1 discloses liquid fabric conditioning compositions comprising a substantially water insoluble fabric softening compound.
  • the compositions have a phase structure with greater than one-dimensional long range order as defined by x-ray crystallography.
  • the compositions are said to exhibit good softening and hydrophobicity .
  • EP 0 380 406 discloses detergent compositions comprising a saccharide or reduced saccharide ester containing at least one fatty acid chain.
  • Bleaching detergent compositions comprising derivatives of pentoses or hexoses , having a long chain acyl or aroyl group and one or more short chain alkyl groups attached through a glycosidic bond are disclosed in WO 91/10719 (Novo) .
  • US 4 800 038 discloses the use of acylated sugar ethers as a bleach activator in nonionic detergent compositions.
  • WO 9500614 discloses softening compositions comprising polyhydric alcohol esters and cationised cellulose.
  • JP 06264049 discloses viscosity improving sucrose long chain fatty acid esters with an average degree of substitution of 4 to 7 in cosmetics and topical skin compositions .
  • US 5 447 643 discloses acqueous fabric softeners comprising nonionic surfactant and mono,di or tri fatty acid esters of certain polyols .
  • WO 96/15213 discloses textile softening agents containing alkyl, alkenyl and/or acyl group containing sugar derivatives, which are solid after esterification, in combination with nonionic and cationic emulsifiers .
  • the present invention is directed towards alleviating the problems associated with the prior art as referred to hereinabove .
  • the principal advantages of the present invention are that its' compositions when used to soften fabrics do so effectively without detriment to the absorbency of the fabric and that the compositions are easily manufactured.
  • a fabric softening composition comprising:
  • CPE cyclic polyol
  • RSE reduced saccharide
  • the invention also relates to a method of treating fabric comprising the step of treating the fabrics with a composition comprising a CPE or RSE wherein the CPE or RSE is a liquid or soft solid having a solid: liquid ratio between 50:50 and 0:100 at 20°C as determined by T 2 relaxation time NMR.
  • the invention also discloses the use of a CPE or RSE as a fabric softening aid that does not decrease the fabric's absorbency.
  • the invention further relates to a liquid or soft solid fatty acid ester of glucose having a solid: liquid ratio between 50:50 and 0:100 as measured above, the ester groups comprising a mixture of C 2 -C 22 alkyl or alkenyl chains and resulting from a cyclic polyol having 35 to 100% of the hydroxyl groups esterified.
  • a sorbitan mono , di or trioleate as a hydrophilic softener is also provided. It has been found, surprisingly, that the above compositions provide an unexpected combination of simultaneous fabric softening and retention of absorbency.
  • the initials CPE or RSE stand for a cyclic polyol derivative or a reduced saccharide derivative respectively which results from 35 to 100% of the hydroxyl groups of the cyclic polyol or reduced saccharide being esterified and/or etherified and in which at least two or more of ester or ether groups are independently of one another attached to a C 8 to C 22 alkyl or alkenyl chain.
  • the ratio of CPE or RSE to deposition aid is preferably within the range of from 1:10 to 15:1, more preferably within the range from 1:5 to 10:1, most preferably 1:1 to 10:1.
  • the ratio of CPE or RSE to deposition aid is at least 1:1 (especially if the deposition aid is a fabric softening compound) .
  • the ratio of a softening deposition aid to CPE or RSE is at least 2:3, preferably 1:1.
  • the ratio of softening deposition aid to CPE or RSE is from 3:2 to 1:10, more preferably from 2:3 to 1:10.
  • the CPE or RSE The CPE or RSE
  • CPEs or RSEs of the present invention result from 35 to 100% of the hydroxyl groups of the starting cyclic polyol or reduced saccharide being esterified or etherified.
  • CPE's or RSE's typically have 3 or more ester or ether groups or
  • ester or ether groups of the CPE or RSE are independently of one another attached to a C 8 to C 22 alkyl or alkenyl chain.
  • the C 8 to C 22 alkyl or alkenyl groups may be branched or linear carbon chains .
  • CPEs are preferred for use with the present invention.
  • Inositol is a preferred example of a cyclic polyol. Inositol derivatives are especially preferred.
  • cyclic polyol encompasses all forms of saccharides. Indeed saccharides are especially preferred for use with this invention. Examples of preferred saccharides for the CPE's or RSE's to be derived from are monosaccharides and disaccharides .
  • monosaccharides include xylose, arabinose, galactose, fructose, sorbose and glucose. Glucose is especially preferred.
  • An example of a reduced saccharide is sorbitan.
  • disaccharides examples include maltose, lactose, cellobiose and sucrose. Sucrose is especially preferred.
  • liquid or soft solid CPE's or RSE's of the present invention can be prepared by a variety of methods well known
  • the CPE or RSE has 4 or more ester or ether groups although for some compounds 3 ester or ether groups produce excellent results and are preferred.
  • the cyclic CPE is a disaccharide it is preferred if the disaccharide has 4 or more ester or ether groups .
  • Particularly preferred CPE's are esters with a degree of esterification of 4 or more, for example, sucrose esters.
  • the saccharide or reduced saccharide has 3 or more ester groups.
  • each ring of the CPE has one ether group, preferably at the C x position, and the remaining hydroxyl groups are esterified.
  • Suitable examples of such compounds include methyl glucose derivatives .
  • CPEs examples include esters of alkyl (poly) glucosides, in particular alkyl glucoside esters having a degree of polymerisation from 1 to 2.
  • ester or ether groups of the cyclic polyol or reduced saccharide are independently of one another attached to a C 8 to C 22 alkyl or alkenyl chain or a C 2 to C 8 chain and in which the ratio of C 8 to C 22 groups to C 2 to C 8 is from 5:3 to 3:5. This is because these products are in the main oils (liquids) and are thus easy to formulate. It has also been found that excellent results are achieved with oils (liquids) .
  • suitable saccharide esters include fatty acid esters of glucose, the ester groups comprising C 2 -C 18 alkyl or alkenyl chain and the degree of esterification being 5.
  • saccharides having ester groups consisting essentially of a C 2 alkyl chain and a C 8 to C 12 straight alkyl chain, the molar ratio of short chain C 2 alkyl chains to C 8 to C 12 straight alkyl chains being from 2:1 to 1:2, more preferably about 1:1 are suitable. It is further preferred if the degree of esterification is at least 5.
  • the liquid or soft solid CPE's or RSE's of the present invention are characterised as materials having a solid: liquid ratio of between 50:50 and 0:100 at 20°C as determined by T 2 relaxation time NMR, preferably between 43:57 and 0:100, most preferably between 40:60 and 0:100, such as, 20:80 and 0:100.
  • the T 2 NMR relaxation time is commonly used for characterising solid: liquid ratios in soft solid products such as fats and margarines.
  • any component of the NMR signal with a T 2 of less than 100 ⁇ s is considered to be a solid
  • % component and any component with T 2 > 100 ⁇ s is considered to be a liquid component .
  • CPE's and RSE's the tetra, penta etc prefixes only indicate the averge degreees of esterification.
  • the compounds exist as a mixture of materials ranging from the monoester to the fully esterified ester. It is the average degree of esterification which is used herein to define the CPE ' s and RSE ' s .
  • Factors governing the suitability of the CPE's and RSE's are the presence and degree of branched chains, mixed chain lengths and the level of unsaturation.
  • a deposition aid is defined as any material that aids deposition of the selected CPE or RSE onto a fabric during the laundering process .
  • the deposition aid may be selected from a fabric softening compounds, cationic compounds, nonionic surfactants, anionic surfactants, polymeric deposition aids or mixtures thereof.
  • the deposition aid is cationic in nature. If a cationic surfactant or cationic softening aid is not present in the formulation it is preferred if a cationic polymeric deposition aid is present. Most preferably the deposition aid is both cationic in nature and is a fabric softening compound.
  • deposition aids may be used, for example, a mixture of a cationic surfactant and a nonionic surfactant, or a fabric softening compound and a polymeric deposition aid.
  • Suitable cationic deposition aids include water soluble single chain quaternary ammonium compounds such as cetyl trimethyl ammonium chloride, cetyl trimethyl ammonium bromide, or any of those listed in European Patent No. 258 923 (Akzo) .
  • the deposition aid is a fabric softening compound.
  • substantially water insoluble quaternary ammonium materials comprising a single alkyl or alkenyl chain having an average length equal to or greater than C 20 are preferred.
  • Even more preferable are compounds comprising a polar head group and two alkyl or alkenyl chains each having an average chain length equal to or greater than C 14 .
  • the fabric softening deposition aid of the invention has two long alkyl or alkenyl chains with an average chain length equal to or greater than C 14 . More preferably each chain has an average chain length greater than C 16 . Most preferably at least 50% of each long chain alkyl or alkenyl group has a chain length of C 18 .
  • the long chain alkyl or alkenyl groups of the fabric softening deposition aid are predominantly linear.
  • the fabric softening deposition aids used in the compositions of the invention are molecules which provide excellent softening, and are characterised by a chain melting -L ⁇ to L ⁇ - transition temperature greater than 25°C, preferably greater than 35°C, most preferably greater than 45°C.
  • This L ⁇ to L ⁇ transition can be measured by DSC as defined in "Handbook of Lipid Bilayers, D Marsh, CRC Press, Boca Raton Florida, 1990 (Pages 137 and 337) .
  • Substantially insoluble fabric compounds in the context of this invention are defined as fabric compounds having a solubility less than 1 x 10 "3 wt% in demineralised water at 20°C.
  • the fabric softening deposition aids have a solubility less than 1 x 10 "4 .
  • the fabric softening deposition aids have a solubility at 20°C in demineralised water from 1 x 10 "8 to 1 x 10 "6'
  • Preferred fabric softening deposition aids are quaternary ammonium compounds, preferably those with at least one ester link.
  • the fabric softening deposition aid is a water insoluble quaternary ammonium material which comprises a compound having two C 12 . 18 alkyl or alkenyl groups connected to the molecule via at least one ester link. It is more preferred if the quaternary ammonium material has two ester links present.
  • 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 ,-
  • T is -O-C- or -C-O-
  • X " is any suitable anion and n is an integer from 0-5
  • Di (tallowoyloxyethyl) dimethyl ammonium chloride is especially preferred.
  • a second preferred type of quaternary ammonium material can be represented by the formula (II) :
  • the quaternary ammonium material is biologically degradable .
  • Preferred materials of this class such as 1,2 bis [hardened tallowoyloxy] -3- trimethylammonium propane chloride and their method of preparation are, for example, described in US 4 137 180 (Lever Brothers) .
  • these materials comprise small amounts of the corresponding monoester as described in US 4 137 180 for example 1-hardened tallowoyloxy -2 -hydroxy 3 -trimethylammonium propane chloride .
  • the fabric softening deposition aid of the composition may also be compounds having the formula (III) :
  • A is an (m+n) valent radical remaining after the removal of (m+n) hydroxy groups from an aliphatic polyol having p hydroxy groups and an atomic ratio of carbon to oxygen in the range of 1.0 to 3.0 and up to 2 groups per hydroxy group selected from ethylene oxide and propylene oxide
  • m is 0 or an integer from 1 to p-n
  • n is an integer from 1 to p-m
  • p is an integer of at least 2
  • B is an alkylene or alkylidene group containing 1 to 4 carbon atoms
  • R 3 , R 4 , R 5 and R fi are, independently from each other, straight or branched chain C 1 -C 48 alkyl or alkenyl groups, optionally with substitution by one or more functional groups and/or interruption by at most 10 ethylene oxide and/or propylene oxide groups, or by at most two functional groups selected from
  • R 11 and R 12 may form a ring system containing 5 or 6 atoms in the ring, with the proviso that the average compound either has at least one R group having 22-48 carbon atoms, or at least two R groups having 16-20 carbon atoms, or at least three R groups having 10-14 carbon atoms.
  • Preferred compounds of this type are described in EP 638 639 (Akzo) .
  • the deposition aid may also be a nonionic surfactant.
  • Preferred nonionic ethoxylated surfactants have an HLB of from about 10 to about 20. It is advantageous if the surfactant alkyl group contains at least 12 carbon atoms .
  • Suitable polymeric deposition aids for use with the invention include cationic and nonionic polymeric deposition aids.
  • Suitable cationic polymeric deposition aids include cationic guar polymers such as Jaguar (ex Rhone Poulenc) , cationic cellulose derivatives such as Celquats (ex National Starch) , Flocaid (ex National Starch) , cationic potato starch such as SoftGel (ex Aralose) , cationic polyacrylamides such as PCG (ex Allied Colloids) .
  • Cationic polymeric aids are particularly preferred in the absence of any other cationic material in the composition.
  • Suitable nonionic deposition aids include Pluronics (ex
  • dialkyl PEGs cellulose derivatives as described in GB 213 730 (Unilever) , hydroxy ethyl cellulose, starch, and hydrpohobically modified nonionic polyols such as Acusol 880/882 (ex Rohn & Haas) .
  • compositions of the invention preferably have a pH from 1.5 to 7, more preferably from 1.5 to 5.
  • compositions of the present invention can also contain fatty acids, for example C 8 - C 24 alkyl or alkenyl monocarboxylic acids, or, polymeric carboxylic acids.
  • fatty acids for example C 8 - C 24 alkyl or alkenyl monocarboxylic acids, or, polymeric carboxylic acids.
  • saturated fatty acids are used, in particular, hardened tallow C 1S -C 18 fatty acids.
  • the composition can also contain one or more optional ingredients, selected from electrolytes, non-aqueous solvents, pH buffering agents, perfumes, perfume carriers, fluorescers, colorants, hydrotropes, antifoaming agents, antiredeposition agents, polymeric and other thickeners, enzymes, optical brightening agents, opacifiers, anti- shrinking agents, anti-wrinkle agents, anti-spotting agents, germicides, fungicides, anti-oxidants , anti-corrosion agents, drape imparting agents, antistatic agents, sunscreens, colour care agents and ironing aids.
  • optional ingredients selected from electrolytes, non-aqueous solvents, pH buffering agents, perfumes, perfume carriers, fluorescers, colorants, hydrotropes, antifoaming agents, antiredeposition agents, polymeric and other thickeners, enzymes, optical brightening agents, opacifiers, anti- shrinking agents, anti-wrinkle agents, anti-spotting agents, germicides, fungicides, anti-
  • any viscosity control agent used with rinse conditioners is suitable for use with the present invention, for example biological polymers such as Xanthum gum (Kelco ex Kelsan and Rhodopol ex Rhone- Poulenc) , Guar gum (Jaguar ex Rhone-Poulenc) , starches and cellulose ethers.
  • biological polymers such as Xanthum gum (Kelco ex Kelsan and Rhodopol ex Rhone- Poulenc) , Guar gum (Jaguar ex Rhone-Poulenc) , starches and cellulose ethers.
  • Synthetic polymers are useful vicosity control agents such as polyacrylic acid, poly vinyl pyrolidone, polyethylene, carbomers , cross linked polyacrylamides such as Acosol 880/882 polyethylene and polyethylene glycols.
  • viscosity modifires are decoupling polymers and defloccculating polymers.
  • compositions may be in any physical form conventionally used for fabric softening compositions for example, powder,
  • IL paste IL paste, gel or liquid. It is preferred if the product is a liquid and especially preferred if it is an emulsion.
  • ⁇ -D glucose (0-111M) was added to pyridine at rocm temperature.
  • Acetyl chloride (0.254M) and decanoyl chloride (0.278M) were mixed together and the acid chloride mixture added drop-wise to the glucose solution.
  • the acid chlorides were added slowly over a period of about 1.5 hours. As the reaction proceeded, large amounts of a thick white precipitate were formed and ethyl acetate was added to maintain the fluidity of the reacton mixture.
  • reaction mixture was stirred overnight (>16 hours) at room temperature.
  • the reaction mixture was filtered to remove the solid pyridine hydrochloride salt and stripped under vacuum to remove the excess pyridine.
  • the remaining produce was taken back up in ethyl acetate, and combined with water in a separating funnel . The mixture was shaken and allowed to separate.
  • the organic layer was washed with water, dilute hydrochloric acid (to remove residual pyridine) , saturated sodium bicarbonate (to remove the residual carboxylic acids) , water (twice) and saturated sodium chloride.
  • the organic layer was dried over magnesium sulphate (anhydrous) overnight, filtered and stripped under high vacuum with heating to leave a pale brown oily residue.
  • Oleic acid (0.40M) (90% technical grade) was mixed with dichloromethane in a large round bottom flask to which Oxalyl chloride (0..44M) in dichloromethane was added. The residual dichloromethane and the excess oxalyl chloride were stripped off under high vacuum to leave 12Og of oleoyl chloride .
  • sucrose 0.044M was added to a mixture of pyridine, ethyl acetate and dimethyl formamide.
  • the oleoyl chloride prepared above was added dropwise to the
  • reaction solvent comprised a mixture of pyridine and dimethyl formamide only
  • the IR spectrum showed only a single sharp peak at 1755cm "1 in the carbonyl region, confirming that there is no residual fatty acid nor fatty acid chloride remianing in the product .
  • Examples 8 to 21 (Table 2) below were prepared by mixing the listed components together in water. All Examples contain 5% active material.
  • Span 80 and Span 85 are available from ICI surfactants
  • CTAC is availble from Aldrich (25% solution) .
  • the Ryoto products are available from Mitsibushi-Kagku Food Corporation
  • HEQ is 1,2 bis (hardened tallowoyloxy] 3 trimethylammonium propane chloride available from Hoechst
  • Accosoft 460 and Accosoft 550 HC are available from Stepan.
  • Softening performance was evaluated by adding O.lg of fabric softening compound (2ml of a 5% a.d. dispersion for liquids) to 1 litre of tap water, at ambient temperature in a tergotometer. Three pieces of terry towelling (8cm x 8cm, 40g total weight) were added to the tergotometer pot. The cloths were treated for 5 minutes at 65 rpm, spin dried to remove excess liquor and line dried overnight and conditioned at 21°C/65 oC / for 24 hours.
  • Each set of test cloths contained one cloth of each test system under a evaluation. Panel members were asked to assess softness on a 8 point scale. Softness scores were calculated using an "Analysis of Variance" technique. Lower values are indicative of better softening.
  • the absorbency was measured using the textile and paper industry wicking (Klemm) test.
  • a strip of treated fabric is held vertically with a clip whilst the free end is weighed down with a piece of rubber.
  • the strip is lowered into a tray containing a 0.02% diphenyl red dye solution such that the rubber weight is just below the surface.
  • the height to which the liquid rises up the strip in one hour is measured (unless stated otherwise) .
  • Six fabric strips are measured for each treatment. "Active in Table 8 is the deposition aid.
  • Examples 48 and 49 were prepared as 5% total active emulsions/dispersion in water of a 1:4 fabric sof ener : sucrose ester mixture. 0.3% of a perfume was included in the compositions which were then tested for perfume longevity. See Table 11 below.
  • Perfume intensity was measured by a trained panel except for example 48 which was measured separately. A value of 0.5 is given for a cloth immersion in fabric. Five represents a very strong smell and 0 an undetable smell. The perfume intensity is assessed after application (when the cloth is wet), after 5 hours and after 24 hours.
  • Example 50 was prepared as a series of a 5% total active emulsions/dispersions in water of 4.5% sucrose tetraerucate (oily liquid, Ryoto ER 290), 0.5% CTAC and 0.2% of a polymer deposition aid (some of which are cationic) as given below: -
  • Example 5Of Merquat 100 (ex Chemviron)
  • Example 51 was prepared as a series of 5% total active emulsions/dispersions in water of 4.5% sucrose tetraerucate (as in Example 55), 0.5% of a nonionic surfactant deposition aid (Synperonic A7) and 0.2% of the following deflocculating polymers (all of which are cationic) .
  • Example 51d Poly DMDAAC:EHA (ex National Starch) - 10:1 molar ratio copolymer (Mwt 2400 approx)
  • Example 52 was prepared as a 1:4 emulsion/dispersion (5% total active) of DEEDMAC: sucrose pentaoleate (Ryoto 0-170) by mixing at high temperatures .
  • a fully formulated fabric softening composition as according to the present invention was prepared as below:
  • sucrose ester oil was Ryoto ER290 available from Mitsubishi Kagaku Foods Corporation.
  • the deposition aid was Floe Aid 34 available from National Starch & Chemical.
  • Table 9 shows the T 2 NMR solid: liquid ratio of CPE's and RSE's used according to the present invention.
  • a comparative crystalline solid sugar ester is also included. The ratios were measured at 20°C. The degree of esterification letherification is stated.
  • S are Sorbitan monoleate and trioleate oily liquids respectively, available from ICI surfactants.

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Abstract

L'invention concerne une composition adoucissant les tissus, qui adoucit les tissus sans affecter la capacité d'absorption du tissu. Ce produit comprend: 1) un dérivé liquide ou solide mou d'un polyol cyclique (CPE) ou d'un saccharide réduit (RSE) obtenu à partir de 35 à 100 % des groupes hydroxyles du polyol cyclique, ou de saccharide réduit en cours d'estérification ou d'éthérification, ce dérivé (CPE ou RSE) comportant au moins deux ou davantage de groupes ester ou éther fixés indépendamment à une chaîne C8-C22 alkyle ou alkényle ou à des mélanges de celles-ci, et contenant au moins 35 % de triesters ou d'esters supérieurs; 2) un agent favorisant un dépôt. Cette invention concerne également des esters d'acides gras de glucose, liquides ou solides mous, comprenant un mélange de chaînes C2-C22 alkyles ou alkényles, qui sont obtenus à partir d'un polyol cyclique tel que défini plus haut.
PCT/EP1997/005762 1996-10-16 1997-10-13 Composition adoucissant les tissus WO1998016538A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
BR9711906A BR9711906A (pt) 1996-10-16 1997-10-13 Composi-Æo amaciante de tecidos usos de um cpe ou rse e de um mono di ou trioleato de sorbitano e -ster de cido graxo l¡quido ou sÄlido mole de glicose
EP97913161A EP0934328A1 (fr) 1996-10-16 1997-10-13 Composition adoucissant les tissus
EA199900383A EA001695B1 (ru) 1996-10-16 1997-10-13 Композиция для размягчения тканей
AU50510/98A AU723907B2 (en) 1996-10-16 1997-10-13 Fabric softening composition

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP96307507 1996-10-16
EP96307507.2 1996-10-16

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WO1998016538A1 true WO1998016538A1 (fr) 1998-04-23

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CN (1) CN1293086C (fr)
AR (1) AR009117A1 (fr)
AU (1) AU723907B2 (fr)
BR (1) BR9711906A (fr)
EA (1) EA001695B1 (fr)
TR (1) TR199900801T2 (fr)
TW (1) TW577946B (fr)
WO (1) WO1998016538A1 (fr)
ZA (1) ZA979231B (fr)

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US8883700B2 (en) 2011-03-03 2014-11-11 The Procter & Gamble Company Dishwashing method utilizing a cationic polymer/surfactant-formed coacervate
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BR9711906A (pt) 1999-08-24
AU723907B2 (en) 2000-09-07
TR199900801T2 (xx) 1999-07-21
TW577946B (en) 2004-03-01
CN1240452A (zh) 2000-01-05
CN1293086C (zh) 2007-01-03
AR009117A1 (es) 2000-03-08
ZA979231B (en) 1999-04-15
AU5051098A (en) 1998-05-11
EA001695B1 (ru) 2001-06-25
EA199900383A1 (ru) 1999-10-28
EP0934328A1 (fr) 1999-08-11

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