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WO2001002522A2 - Formulation adoucissantes limpides renfermant des additifs alcoxyles - Google Patents

Formulation adoucissantes limpides renfermant des additifs alcoxyles Download PDF

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Publication number
WO2001002522A2
WO2001002522A2 PCT/US2000/017913 US0017913W WO0102522A2 WO 2001002522 A2 WO2001002522 A2 WO 2001002522A2 US 0017913 W US0017913 W US 0017913W WO 0102522 A2 WO0102522 A2 WO 0102522A2
Authority
WO
WIPO (PCT)
Prior art keywords
formulation
fabric softening
alkyl
active fabric
solvent
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/US2000/017913
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English (en)
Other versions
WO2001002522A3 (fr
Inventor
Pierre Marie Lenoir
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dow Chemical Co
Original Assignee
Dow Chemical Co
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 Dow Chemical Co filed Critical Dow Chemical Co
Priority to EP00943283A priority Critical patent/EP1198548A2/fr
Priority to AU57778/00A priority patent/AU5777800A/en
Priority to US10/009,194 priority patent/US6680290B1/en
Priority to JP2001508296A priority patent/JP2003519293A/ja
Publication of WO2001002522A2 publication Critical patent/WO2001002522A2/fr
Anticipated expiration legal-status Critical
Publication of WO2001002522A3 publication Critical patent/WO2001002522A3/fr
Ceased legal-status Critical Current

Links

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
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2003—Alcohols; Phenols
    • 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
    • C11D1/72—Ethers of polyoxyalkylene glycols
    • C11D1/721—End blocked ethers
    • 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
    • C11D1/722—Ethers of polyoxyalkylene glycols having mixed oxyalkylene groups; Polyalkoxylated fatty alcohols or polyalkoxylated alkylaryl alcohols with mixed oxyalkylele 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
    • C11D11/00—Special methods for preparing compositions containing mixtures of detergents
    • C11D11/0094—Process for making liquid detergent compositions, e.g. slurries, pastes or gels
    • 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
    • C11D3/2068—Ethers
    • 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
    • C11D3/2093—Esters; Carbonates
    • 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
    • C11D3/26—Organic compounds containing nitrogen
    • C11D3/30—Amines; Substituted amines ; Quaternized 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
    • C11D3/43—Solvents

Definitions

  • the present invention relates to softening formulations, and especially fabric softening formulations, which remain clear at relatively low temperatures and at relatively low concentrations of the active fabric softening ingredient. More particularly the invention relates to a formulation comprising an active fabric softening ingredient, water, and an alkoxylated species having a mono function H, such as alcohols, fatty acids and amines.
  • the formulations may optionally contain solvents, and other additives generally used in fabric softening or detergent compositions.
  • Fabric softening formulations have long been used to render washed clothing or other articles, softer to the touch. It is believed, however, that many consumers avoid the use of fabric softeners due in part to the typical fabric softener's cloudy appearance. Some consumers perceive that the cloudiness will leave a residue on the laundered articles, dulling the colors, and perhaps irritating skin which may come into contact with it. Thus, there is a need for fabric softening compositions having a water-like clear appearance. Many attempts at clear fabric softening formulations have been reported in the literature. For example, U.S. Patent No. 5,490,944, teaches a clear fabric softening composition containing an amido imidazolinium compound.
  • R 1 -Q-(AO) n -R 3 where R, is C 1 18 alkyl, cylcloalkyl or aryl; Q is O, C(0)0, or NR A is CH 2 CHR 2 ; R 2 and R 3 are independently at each occurrence H or C, 4 alkyl; and n is 2 to 13; with the proviso that in at least one AO group R 2 is H and in at least one AO group R 2 is not H.
  • additives can be combined with known detergent or fabric softening active ingredients as well as lower aliphatic solvents, water, and other ingredients typically used in fabric softening formulations.
  • compositions of the present invention comprise: (A) an active fabric softening composition
  • R,-Q-(AO) -R 3 where R, is C 1 18 alkyl, cylcloalkyl or aryl; Q is O, C(O)O, or NR,; A is CH 2 CHR 2 ; R 2 and R 3 are independently at each occurrence H or C 1 4 alkyl; and n is 2 to 13; with the proviso that in at least one AO group R 2 is H and in at least one AO group R 2 is not H; and preferably
  • the formulations may also include a lower aliphatic solvent, and other additives typically found in detergent or fabric softening compositions.
  • the active fabric softening ingredient used in the formulations of the ingredient can be selected from any of those known in the art, such as those described in the review article "Rinse-Added Fabric Softener Technology at the Close of the Twentieth Century", Matthew I. Levinson, Journal of Surfactants and Detergents, Vol 2, No.2, pages 223-235 (April, 1999).
  • the active ingredient will be a quaternary ammonium compound, especially an ester quaternary ammonium compound ("ester quats”), diamido amines and diamido ammonium compounds, and amido imidazolinium compounds.
  • Non ester quaternary ammonium compounds are characterized by having a quaternized ammonium where at least one of the branches attached to the nitrogen contains a long (C ⁇ -C 22 ) alkyl chain. Preferably there are two such long alkyl chains.
  • Suitable non ester quaternary ammonium compounds are described for example in WO 99/09122.
  • the esterquat class of compounds is characterized by having a central nitrogen being joined to four organic groups, at least one of which contains an organic acid moiety, that is, a C(0)OR group, where R is the remaining portion of the fatty acid used to make the ester. It is preferred that two of the organic groups joined to the nitrogen contain esters.
  • diesterquats are: methyl bis(oleoyl-oxy-ethyl)-(2- hydroxyethyl) ammonium methyl sulfate (TEA diesterquat); N,N-di(oleoyl-oxy-ethyl)-N,N- dimethyl ammonium chloride (MDEA diesterquat); and 1 ,2-dioleoyloxy-3-N,N,N- trimethylammoniopropane chloride (DMAPD diesterquat).
  • TAA diesterquat methyl bis(oleoyl-oxy-ethyl)-(2- hydroxyethyl) ammonium methyl sulfate
  • MDEA diesterquat N,N-di(oleoyl-oxy-ethyl)-N,N- dimethyl ammonium chloride
  • DMAPD diesterquat 1 ,2-dioleoyloxy-3-N,N,N- trimethylammoniopropane
  • diamido ammonium compounds Suitable, but non limiting, examples of diamido ammonium compounds are described, in U.S. Patent Nos. 5,525,245, 5,656,585, and WO 99/09122. Some specific examples include diamido (oleic type) alkoxylated or not (EO, PO, and or BO) amines and their quaternary ammonium salts (DETA based) of the formula:
  • R 4 -(CO)-NR 6 -(CH 2 CH 2 )-N(R 5 )(R 8 )-(CH 2 CH 2 )-NR 6 -(CO)-R A " wherein R” together with (CO) is an oleoyl group; R 5 is H, C 1 -C 4 alkyl or (CH 2 - CR 7 HO),-H, with t being from 1 to 7; R 6 is H, or CH 2 -CR 7 HOH; and R 7 is H or C,-C alkyl; R ⁇ is not present or C x H 2x+1 , where x is 0 to 4 and A ' is an inorganic or organic acid anion (such as methyl sulfate, or a chloride anion) or not present when R 8 is not present. It will be readily understood by those in the art that if R ⁇ and A " are not present then, the "+" designation in the formula will also disappear.
  • Suitable amido imidazolinium compounds are described, for example in WO 99/09122, WO 98/23808, and U.S. Patent No. 5,490,944.
  • Other materials which may be used as the fabric softening active ingredient in the formulations of this invention include the amido esterquats of U.S. Patent 5,580,481 and their respective amido esteramines.
  • a fatty acid or derivative that is, a material containing a moiety corresponding to the formula RC(O)O-
  • the fatty acid has an iodine value of between 20 and 140, especially for fatty acids having a predominant chain length in the range of C 16 -C 1 ⁇ .
  • iodine values 0 to 100 are preferred.
  • Preferred fatty acids are described in WO 97/03169, see for example, pages 18 to 21 .
  • fatty acid used is typically derived from a triglyceride source.
  • triglyceride sources are those derived from tallow, partially hardened tallow, lard, partially hardened lard, vegetable oils and/or partially hydrogenated vegetable oils, such as, canola oil, safflower oil, peanut oil, sunflower oil, corn oil, sunbean oil, tall oil, rice bran oil, coconut oil, palm oil, cotton seed oil, olive oil, cod liver oil, and mixtures of these oils.
  • the fabric softening active ingredient may be present in the formulation in an amount of from 1 to 85 percent based on the weight of the total formulation. Preferably it is added in a range of from 5 to 70 and more preferably from 10 to 65.
  • the additive to be used in the formulations of the present invention correspond to the formula:
  • R 1 -Q-(AO) -R 3 where R, is C 1 18 alkyl, cycloalkyl or aryl; Q is preferably O, but can also be C(O)0, or NR,; A is CH.CHR 2 ; R 2 and R 3 are independently at each occurrence H or C, 4 alkyl; and n is 2 to 13; with the proviso that at least one R 2 is H and at least one R 2 is not H.
  • the alkoxylated additives to be used in the formulations of the present invention will contain at least one mole of ethylene oxide (“EO”) and one mole of a higher oxide such as propylene oxide (“PO”) or butylene oxide (“BO”).
  • R is an alkyl group and the alkyl group may be branched or linear, saturated or unsaturated. It is preferred that R, contain from 2 to 17 carbon atoms, and more preferably from 3 to 15.
  • R 3 be H.
  • the preferred AO units are those derived from EO, PO, and BO.
  • the alkylene oxide portion of the additive may be added by random or block addition or a mixture thereof. Due to the relative reactivities of EO versus higher oxides, if the addition is random, the EO will tend to be added first. It is also possible to add the oxide units in a mixed block/random fashion, for example, by adding a few moles of PO or BO first and then by adding a mixed feed of EO with PO or BO. Similarly, it is possible to add the mixed feed first and then cap the additive with higher AO units by the addition of pure higher alkylene oxide.
  • One preferred class of additives has 1 to 8 moles of EO followed by 1 to 5 moles of BO and/or PO.
  • Another preferred class has 1 to 5 moles of PO and/or BO followed by 1 to 3 moles of EO.
  • Still another preferred class has 1 to 3 moles of PO and/or BO followed by a random or block addition of 1 to 8 moles of EO with an additional 1 to 3 moles of PO and/or BO.
  • Still another preferred class of additives results from the completely random addition of 1 to 8 moles of EO with 1 to 5 moles of BO and/or PO.
  • Yet another class of additives has a block of 1 to 8 EO units followed by the random addition of 2 to 7 moles of EO with PO and/or BO.
  • the additives can be added in an amount of from 1 to 60 percent by weight based on the total formulation. Preferably it is added in an amount of from 3 to 50, more preferably from 5 to 35.
  • the additives of the present invention can be prepared by alkoxylating a starting material having the formula R ⁇ Q-H where R, and Q are as defined before. Any method of alkoxylation may be used.
  • the alkoxylation reaction may be carried out in the presence of an alkaline catalyst, such as sodium, potassium, calcium, barium and strontium hydroxide, in an amount of from 0.01 to 5, preferably 0.1 to 0.5, percent by weight based on the total weight of the mixture at the completion of the reaction.
  • Temperature and pressures are not critical, but conveniently the alkoxylation reaction is carried out at an elevated temperature, preferably at a temperature from 50°C to 200°C, more preferably from 80°C to 140°C and a pressure of from 1 to 80 bars.
  • the alkaline catalysts suitable for use in this reaction are well known to a person skilled in the art. After completion of the reaction, that is, for example, when the pressure does not change anymore, the catalyst is removed by a suitable method, such as by filtration over an absorbing clay, for example, magnesium silicate, or neutralized with an inorganic acid such as, for example, hydrochloric acid, or an organic acid such as, for example, acetic acid.
  • a suitable method such as by filtration over an absorbing clay, for example, magnesium silicate, or neutralized with an inorganic acid such as, for example, hydrochloric acid, or an organic acid such as, for example, acetic acid.
  • the additives of the present invention offer many other advantages. As these additives are not traditional solvents, they avoid many of the problems associated with the traditional solvents. Thus, by using the additives of the present invention instead of some or all of the solvents specified in the prior art, odor and flammability issues are reduced. Furthermore, the additives of the present invention are surfactants and thus may offer additional cleaning properties. It is also believed that the formulations including the additives may facilitate or even eliminate the need for ironing the clothes after the wash.
  • the formulation of the present invention can also include up to 25 percent by weight of a solvent selected from aliphatic alcohols, aryl alkyl alcohols, aliphatic polyalcohols and their alkoxylates, aliphatic ethers, alkylene carbonates, and aliphatic esters.
  • a solvent selected from aliphatic alcohols, aryl alkyl alcohols, aliphatic polyalcohols and their alkoxylates, aliphatic ethers, alkylene carbonates, and aliphatic esters.
  • solvents can help reduce the viscosity of the formulations and help clarity, especially at lower temperatures. In general, the lower the concentration of these solvents present in the formulation the better, so long as the formulation remains clear.
  • these solvents are present in an amount from 0.1 to 15 percent by weight of the formulation, but can comprise less than 10 or even less than 6 percent of the formulation.
  • Suitable solvents are generally known in the art, and are listed for example in U.S. Pat. No. 5,525,245 or WO 99/09122.
  • Other solvents which may be used include the "principal solvents" (for example, those solvents with a Clog P value of from 0.15 to 1 .0) listed in WO 97/03169 and WO 99/09122.
  • Preferred solvents include propanol, isopropyl alcohol, ethanol, butanol, ethylene glycol, 1 ,3-propane diol, propylene glycol, propylene carbonate, glycol ethers such as DOWANOLTM (trademark of The Dow Chemical Company) P and E series including dipropylene glycolpropyi ether (DPnP) and dipropylene glycolbutyl ether (DPnB), diethylene glycol butyl ether (DB), 1 ,4-cyclohexandimethanol and glycerol.
  • DOWANOLTM dipropylene glycolpropyi ether
  • DPnB dipropylene glycolbutyl ether
  • DB diethylene glycol butyl ether
  • 1 ,4-cyclohexandimethanol and glycerol.
  • ingredients typically used in fabric softeners and detergents may also be used in the formulations of the present invention. These are known in the art (see for example WO 99/09122, U.S. Patent No. 5,656,585, WO-97/31889, WO 98/35002, WO-A- 95/19951 , WO-A-93/25648, WO-A-93/23510, WO-A-96/21715, WO-A-96/09436, WO-A- 94/29521 , GB 2 197 66 A, EP 0 413 249 A1 , WO 98/41604, WO 97/03169, WO 98/18890, WO 96/33800 and EP-A-0580245) and include things such as brighteners; dispersibility aids such as cationic surfactants (for example, monoalkyl quaternary ammonium compounds), nonionic surfactants (such as C 4 -C 20 fatty alcohols or fatty acids e
  • the formulations of the present invention may advantageously contain water or be anhydrous. If water is present, it may comprise more than 10 percent of the formulation, more preferably more than 20 percent, and most preferably more than 30 percent by weight of the formulation. It should be understood that the formulations of the present invention are typically microemulsions and/or liquid crystals and as such will turn turbid at very high concentrations of water such as when diluted in the rinse cycle.
  • the formulations of the present invention can be made in several ways, as should be readily understood in the art.
  • the individual components that is, fabric softening active ingredient, the additive, water and any optional ingredients
  • the individual components can be simply blended together (at elevated temperatures if required) in any order.
  • the fabric softener active ingredient is based on the fatty acid
  • the additive could be added after the esterification and either before, during or after the quaternization step, enabling the reduction or even the elimination of the traditional solvents used in such process.
  • ACROPOL 35 is a trademark from BASF and designates C 13 -C 15 oxo-alcohol.
  • Fabric softener 1 (“FS 1") is a triethanolamine esterquat based on oleic acid
  • fabric softener 2 ("FS 2") is a methyldiethanolamine esterquat based on oleic acid.
  • IPA is isopropyl alcohol
  • PG is propylene glycol
  • DB is diethylene glycol butyl ether.

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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)
  • Emergency Medicine (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

Cette invention a trait à des formulations adoucissantes et, notamment, à des adoucisseurs de tissus, demeurant limpides à des températures relativement basses et sous des concentrations relativement faibles des ingrédients actifs entrant dans la composition de l'adoucisseur. Ces formulations renferment une composition active pour adoucisseur de tissus et un additif correspondant à la formule R1-Q-(AO)n-R3, formule dans laquelle R1 représente un alkyle en C1-18, Q représente O, C(O)0, or NR1, A représente CH2CHR2, R2 et R3 représentent, de manière indépendante, à chaque occurrence, H ou un alkyle en C1-4, la valeur de n étant comprise entre 2 et 13, et ce, à la condition qu'au moins un R2 représente H et qu'au moins un R2 ne représente pas H. Ces formulations contiennent également, de préférence, de l'eau et un solvant, lequel solvant peut être constitué par des alcools aliphatiques porteurs de 1 à 6 atomes de carbone, des alcools aryl-alkyl, des polyols aliphatiques et leurs alcoxylates, des éthers aliphatiques, des esters aliphatiques ou des carbonates l'alcylène et leurs mélanges.
PCT/US2000/017913 1999-07-02 2000-06-29 Formulation adoucissantes limpides renfermant des additifs alcoxyles Ceased WO2001002522A2 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP00943283A EP1198548A2 (fr) 1999-07-02 2000-06-29 Formulation adoucissantes limpides renfermant des additifs alcoxyles
AU57778/00A AU5777800A (en) 1999-07-02 2000-06-29 Clear softening formulations including alkoxylated additives
US10/009,194 US6680290B1 (en) 1999-07-02 2000-06-29 Clear softening formulations including alkoxylated additives
JP2001508296A JP2003519293A (ja) 1999-07-02 2000-06-29 アルコキシレート化添加剤を含有する透明な軟化用調合物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US14221099P 1999-07-02 1999-07-02
US60/142,210 1999-07-02

Publications (2)

Publication Number Publication Date
WO2001002522A2 true WO2001002522A2 (fr) 2001-01-11
WO2001002522A3 WO2001002522A3 (fr) 2002-09-26

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Application Number Title Priority Date Filing Date
PCT/US2000/017913 Ceased WO2001002522A2 (fr) 1999-07-02 2000-06-29 Formulation adoucissantes limpides renfermant des additifs alcoxyles

Country Status (4)

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EP (1) EP1198548A2 (fr)
JP (1) JP2003519293A (fr)
AU (1) AU5777800A (fr)
WO (1) WO2001002522A2 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003022977A1 (fr) * 2001-09-10 2003-03-20 The Procter & Gamble Company Procede de lavage
WO2009065823A3 (fr) * 2007-11-23 2009-09-24 Henkel Ag & Co. Kgaa Agent de traitement de textiles biocide

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB0907003D0 (en) * 2009-04-23 2009-06-03 Syngenta Ltd Formulation

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2459354C2 (de) * 1974-12-16 1986-03-27 Hoechst Ag, 6230 Frankfurt Waescheweichspuelmittelkonzentrat mit desinfizierenden eigenschaften
DE3150178A1 (de) * 1981-12-18 1983-06-30 Hoechst Ag, 6230 Frankfurt "konzentrierte waescheweichspuelmittel"
GB8410320D0 (en) * 1984-04-19 1984-05-31 Unilever Plc Aqueous fabric softening composition
US5656585A (en) * 1994-12-21 1997-08-12 Colgate-Palmolive Company Clear, concentrated liquid fabric softener compositions
ES2174913T3 (es) * 1995-09-18 2002-11-16 Procter & Gamble Composiciones estabilizadas suavizantes de tejidos.
KR100259266B1 (ko) * 1996-11-28 2000-06-15 손경식 액체 섬유유연제 조성물
JP4049996B2 (ja) * 1997-08-18 2008-02-20 ザ プロクター アンド ギャンブル カンパニー 透明液体布地柔軟化組成物
AU2769299A (en) * 1998-02-19 1999-09-06 Colgate-Palmolive Company, The Stable rinse cycle fabric softener composition with glycerol monostearate co-softener

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003022977A1 (fr) * 2001-09-10 2003-03-20 The Procter & Gamble Company Procede de lavage
WO2009065823A3 (fr) * 2007-11-23 2009-09-24 Henkel Ag & Co. Kgaa Agent de traitement de textiles biocide
US8143207B2 (en) 2007-11-23 2012-03-27 Henkel Ag & Co. Kgaa Biocidal textile treatment agent

Also Published As

Publication number Publication date
AU5777800A (en) 2001-01-22
WO2001002522A3 (fr) 2002-09-26
EP1198548A2 (fr) 2002-04-24
JP2003519293A (ja) 2003-06-17

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