EP0200263B1 - Compositions détergentes homogènes concentrées et liquides contenant un système tensioactif ternaire - Google Patents

Compositions détergentes homogènes concentrées et liquides contenant un système tensioactif ternaire Download PDF

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Publication number
EP0200263B1
EP0200263B1 EP86200690A EP86200690A EP0200263B1 EP 0200263 B1 EP0200263 B1 EP 0200263B1 EP 86200690 A EP86200690 A EP 86200690A EP 86200690 A EP86200690 A EP 86200690A EP 0200263 B1 EP0200263 B1 EP 0200263B1
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Prior art keywords
composition
weight
accordance
acid
surfactant system
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German (de)
English (en)
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EP0200263A3 (en
EP0200263B2 (fr
EP0200263A2 (fr
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Jean Wevers
Christian Roland Barrat
Jean-Pol Boutique
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Procter and Gamble European Technical Center
Procter and Gamble Co
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Procter and Gamble European Technical Center
Procter and Gamble Co
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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
    • C11D10/00—Compositions of detergents, not provided for by one single preceding group
    • C11D10/04—Compositions of detergents, not provided for by one single preceding group based on mixtures of surface-active non-soap compounds and soap
    • 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
    • C11D1/02—Anionic compounds
    • C11D1/04—Carboxylic acids or salts thereof
    • C11D1/08—Polycarboxylic acids containing no nitrogen or sulfur
    • 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
    • C11D1/83—Mixtures of non-ionic with anionic 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
    • C11D1/02—Anionic 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
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
    • C11D1/143—Sulfonic acid esters
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
    • C11D1/146—Sulfuric acid esters
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/22—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aromatic 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
    • 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

Definitions

  • compositions herein are characterized by the utilization of a ternary surfactant system and contain less than 50% water.
  • the ternary surfactant system contains a majority of an anionic surfactant which is represented by a binary mixture of an alkyl(aryl) sulfonated surface-active agent and an alk(en)yl succinate in a weight ratio of sulfonate to succinate in the range of from 3:1 to 1:4, and a nonionic surfactant component.
  • the inventive compositions exhibit excellent and highly desirable detergency, they can be manufactured easily and furthermore display excellent stability during prolonged periods of storage.
  • Homogeneous concentrated heavy duty liquid detergents are well-known in the art and have found commercial application.
  • the like compositions can comprise a ternary active system, namely: synthetic anionic sulfonates or sulfates in combination with nonionic ethoxylates and soaps.
  • Such prior art compositions are difficultly processable, particularly depending upon alkalinity.
  • the prior art concentrated liquid detergents are in that respect vulnerable to phase separation under neutral to mildly alkaline conditions.
  • U.S. Patent 4.285.841 discloses builder-free concentrated homogeneous liquid compositions containing a combination of anionic synthetic surface-active compounds, nonionic surface-active compounds and fatty acids.
  • the manufacture of the like compositions containing less than 50% water requires the utilization of substantial amounts of solvents and/or compatibilizing agents and even under those circumstances, remain of borderline stability having particularly regard to levels and type of nonionics, fatty acids, particularly saturated species, and optional electrolytes such as low levels of organic builders.
  • the succinate ingredient is well-known in the detergent art and has been disclosed in combination with all kinds of detergent executions, mostly granular compositions. While, the like succinates have been recommended for utilization in liquid compositions, it is well-known that substantial formulation difficulties will originate from their use in such compositions, particularly in presence of low levels of water and substantial amounts of nonionics.
  • German Patent 17 68 851 relates to the utilization of specific succinate derivatives as suds boosters. These compositions contain solely anionic surface-active agents and furthermore substantial levels of water in combination with additional hydrotropes.
  • German Patent 19 56 671 discloses binary liquid preparations containing substantial levels of alk(en)yl succinates in combination with nonionic surface-active agents.
  • German Patent Application 30 13 904 relates to alkaline cleaning agent compositions, solid or liquid, containing a partially neutralized succinic acid derivative which seems to be utilized for its foaming properties.
  • EP-A-0 017 951 relates to the utilization of alk(en)yl succinic acid salts or monoesters thereof with polyvalent alcohols for hydrotroping perfumes in liquid detergent compositions containing high levels of electrolytes.
  • EP-A-0 028 850 relates to the utilization of monoalkyl or alkenyl C 7 - 12 , preferably C 8 and C 9 succinates, as hydrotropes in nonionic-based liquid detergent compositions.
  • GB-A-2 049 723 discloses the use of partially neutralized alkyl succinates in replacement for conventional surfactants, in liquid detergent compositions.
  • compositions herein are characterized by the presence of:
  • the invention herein can be embodied by highly concentrated homogeneous liquid detergent compositions containing a ternary surfactant system and having a pH in the neutral to mildly alkaline range.
  • the anionic surfactant component amounts to from 50% to 90% of the ternary surfactant system and is represented by a binary combination of:
  • the anionic sulfonate surfactant can be represented by all alkyl(aryl) sulfonated surface-active agents which are known to be suitable for use in liquid detergent compositions and have been used in fact, extensively, in commercial detergent executions.
  • anionic synthetic sulfonates can be represented by the general formula R l So 3 M wherein R 1 represents a hydrocarbon moiety selected from the group consisting of straight or branched alkyl radicals containing from 8 to 24 carbon atoms and alkyl phenyl radicals containing from 10 to 18 carbon atoms in the alkyl group.
  • M is a salt forming cation which typically is selected from the group consisting of sodium, potassium, magnesium, ammonium, monoalkanolammonium, dialkanolammonium, trialkanolammonium and mixtures thereof.
  • a preferred synthetic anionic sulfonate surfactant is a water-soluble salt of an alkylbenzene sulfonic acid containing from 10 to 18 carbon atoms in the alkyl group, the most preferred species for use herein having from C12 2 to C16 carbon atoms in the alkyl chain.
  • the alk(en)yl succinate has the formula referred to hereinbefore wherein R 1 is either a saturated or unsaturated radical having from 10 to 20 carbon atoms, preferably an unsaturated derivative having from 12 to 16 carbon atoms in the alkenyl moiety.
  • R 2 can be hydrogen or C 1 -C 4 alkyl, although hydrogen is preferred.
  • succinate and “succinic acid” are used interchangeably.
  • Suitable succinic acid salts include the sodium, potassium, lithium, ammonium, mono-, di- and tri-alkanol amine salts and mixtures thereof.
  • Preferred succinic acid derivatives for use herein include 2-dodecenylsuccinic acid, 2-tetradecenylsuccinic acid, 2-hexadecenylsuccinic acid, decyl succinic acid, dodecyl succinic acid and tetradecyl succinic acid and the water- soluble salts thereof.
  • the alkyl or alkenyl chain attached to succinic acid can be either straight or branched. Preferred are the straight-chain alk(en)yl moieties.
  • the weight ratio of sulfonate to succinate surfactant in the binary mixture is in the range from 3:1 to 1:4, preferably from 2:1 to 1:2.
  • the ternary surfactant system represents usually from 35% to 75% of the composition.
  • the anionic surfactant component is defined in the salt form.
  • the nonionic surfactant component contains a hydrophobic organic radical condensed with an ethylene oxide hydrophilic moiety.
  • All ethoxylated nonionic surfactants which are known to be suitable for use in detergent application can be used in the compositions of this invention.
  • Preferred nonionic species herein are polyethoxylates derived from primary and secondary aliphatic alcohols having from 8 to 24 carbon atoms, and having a HLB (hydrophilic- lipophilic balance) in the range from 8 to 15. These preferred ethoxylates frequently contain from 2 to about 14 moles of ethylene oxide per mole of hydrophobic moiety.
  • the hydrocarbyl chain (hydrophobic moiety) can be represented by linear or branched fatty alcohols.
  • a preferred class of nonionic ethoxylates is represented by the condensation product of a fatty alcohol having from 12 to 15 carbon atoms and from 4 to 10 moles of ethylene oxide per mole of fatty alcohol.
  • Suitable species of this class of ethoxylates include: the condensation product of C 12 -C15 oxo-alcohols and 7 moles of ethylene oxide per mole of alcohol; the condensation product of C 13-15 oxoalcohols and 5 moles of ethylene oxide; the condensation product of narrow cut C14-C15 oxo-alcohols and 7 or 9 moles of ethylene oxide per mole of fatty (oxo)alcohol; the condensation product of a narrow cut C 12 -C 13 fatty (oxo)-alcohol and 6.5 moles of ethylene oxide per mole of fatty alcohol; and the conden- sation products of a Cio-C 1 coconut fatty alcohol with a degree of ethoxylation (moles EO/mole
  • the fatty oxo alcohols while mainly linear can have, depending upon the processing conditions and raw material olefins, a certain degree of branching, particularly short chain such as methyl branching.
  • a degree of branching in the range from 15% to 50% (weight %) is frequently found in commercial oxo-alcohols.
  • Preferred nonionic ethoxylated components can also be represented by a mixture of 2 separately ethoxylated nonionic surfactants having a different degree of ethoxylation.
  • the nonionic ethoxylate can be represented by mixtures of a first ethoxylated surfactant containing from 3 to 7 moles of ethylene oxide per mole of hydrophobic moiety and a second ethoxylated species having from 8 to 14 moles of ethylene oxide per mole of hydrophobic moiety.
  • a preferred nonionic ethoxylated mixture contains a lower ethoxylate which is the condensation product of a C 12 -C15 oxo-alcohol, with up to 50% (wt) branching, and from 3 to 7 moles of ethylene oxide per mole of fatty oxo-alcohol, and a higher ethoxylate which is the condensation product of a C 16 - C1 oxo-alcohol with more than 50% (wt) branching and from 8 to 14 moles of ethylene oxide per mole of branched oxo-alcohol.
  • the nonionic surfactant component represents from 50% to 10%, preferably from 15% to 40% of the ternary surfactant system.
  • compositions herein contain less than 50%, usually from 15% to 40% water.
  • the claimed compositions are further characterized by a pH, measured in 1% aqueous solution at 20 C, in the range from 7 to 9.
  • This pH range implies that the anionic surfactant component, i.e., the binary mixture of sulfonate and succinate, particularly the succinate, is substantially completely (i.e., more than 90%) neutralized in the claimed composition as is.
  • compositions herein frequently contain a series of optional ingredients which are used for their known functionality in conventional quantities.
  • optional ingredients can include fatty acids, saturated and/or unsaturated, and the corresponding soaps, synthetic anionic surfactants which are different from sulfonates (non-sulfonate anionics), water-insoluble solvents, enzymes, enzyme stabilizers, polyacids, suds regulants, brighteners, perfumes, dyes, antioxidants, bactericides, corrosion inhibitors, fabric-softening agents, phase regulants and the like.
  • Suitable fatty acids saturated or unsaturated, have from 10 to 18 carbon atoms in the alkyl chain. Preferred are unsaturated species having from 14 to 18 carbon atoms in the alkyl chain, most preferably oleic acid.
  • the corresponding soaps can equally be used.
  • the optional fatty acid/soaps are used in levels up to 10%, preferably from 1% to 8%, (of the composition).
  • the fatty acids/soaps among others, act as suds modifiers/regulants.
  • Synthetic non-sulfonate anionics can also be used in the composition in relatively minor levels, e.g. in levels not exceeding 25% of the ternary surfactant system.
  • suitable non-sulfonate anionics include the salts of sulfated fatty alcohols having from 12 to 20 carbon atoms in the alcohol chain.
  • Water-insoluble solvents such as terpenes, phthalic acid esters and liquid paraffins can also be used in levels generally below 5%.
  • Detergent enzymes generally aid and augment the removal of specific stains.
  • Suitable enzymes can be represented by proteases, amylases, lipases, glucose-oxidases, cellulase, or mixtures thereof.
  • Proteases and amylases are preferred in the claimed liquid concentrated compositions. They are frequently employed in a level from about 0.01 % to about 1 %.
  • Suitable stabilizing systems include short C 1 - 4 chain carboxylic acid, particularly formic acid in combination with low level of calcium, boric acid and the water-soluble salts thereof possibly in combination with polyols.
  • polyacid or mixture of polyacids in an amount from 0.05% to 2%.
  • Suitable polyacids are those having one pK value of at least 5.
  • Preferred polyacid species for use herein can be represented by organo-phosphonic acids, particularly alkylene-polyamino-polyalkylene phosphonic acids such as ethylene diamine tetramethylenephosphonic acid, and diethylene triaminepentamethylenephosphonic acid or the salts thereof.
  • Suitable polyamino-polyalkylene ethoxylate polymers are disclosed in European Patent Application number 0 112 593.
  • Non-fatty acid detergent suds regulants can also be used.
  • Preferred species include alkylated polysiloxanes such as dimethylpolysiloxane also frequently termed silicone.
  • the silicones are frequently used in a level not exceeding 0.5%, most preferably between 0.01 % to 0.2%.
  • compositions herein can also contain known antioxidants for their known utility, frequently radical scavengers, in the art established levels i.e. 0.01% to 0.25% (by reference to total composition). These antioxidants are frequently introduced in conjunction with unsaturated organic acids. While many suitable antioxidants are readily known and available for that purpose, especially preferred for use in the compositions herein are: 2,6 ditertiary butyl-p-cresol, more commonly known as butylated hydroxytoluene, BHT, and 2-tertiarybutyl-4-hydroxyanisole. Other suitable antioxidants are: 4,4'thiobis(6-ter-butyl-m-cresol) and 2-methyl-4,6-dinonyl phenol.
  • Soil release polymers can also be incorporated in the compositions herein. Suitable species of such release polymers are described in U.S. Patent Application Serial Number 684.511, filed December 21, 1984, incorporated herein by reference.
  • phase regulant is a further optional ingredient in the compositions herein.
  • This component together with water can constitute the solvent matrix for the claimed concentrated liquid compositions.
  • Suitable ingredient classes include lower aliphatic alcohols having from 2 to 6 carbon atoms and from 1 to 3 hydroxyl groups, ethers of diethyleneglycol and lower aliphatic monoalcohols having from 1 to 4 carbon atoms.
  • Specific examples of phase regulants are: ethanol; n-propanol; isopropanol; butanol; 1,2-propanediol; 1,3-propanediol; monomethyl-, ethyl-, propyl-, and monobutyl ethers of di-ethylene glycol.
  • a liquid detergent composition in accordance with the invention is prepared by mixing the listed ingredients in the stated proportions.
  • the preceeding composition is, from a detergency performance standpoint, compared to ARIEL, R a granular tripolyphos- phate built detergent containing oxygen bleach.
  • the tests are carried out in a horizontal drum washing machine in an up-to-60 ° C cycle. Comparative performances are measured on cotton strips, stained with various types of artificial soils inclusive of bleach-builder sensitive soils, enzyme- sensitive soils, particulate soils and greasy-oily soils. It is found that the composition in accordance with this invention provides textile cleaning performance on all types of soils comparable to what is obtained from ARIEL.
  • Example I It was also found that the liquid composition of Example I remained homogeneous and stable after at least 2 weeks storage at temperatures varying from 4 ° C to 50 ° C and also following exposure to several freeze-thaw cycles.

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  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
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Claims (9)

1. Composition détergente aqueuse homogène, concentrée et liquide , contenant moins de 50 % en poids d'eau , un système tensio-actif ternaire anionique/non ionique,et,si on le désire , des additifs traditionnels , caractérisée en ce que :
(a) le système tensio-actif ternaire représente de 35 % à 75 % en poids ( de la composition) ;
(b) le composant tensio-actif anionique représente de 50 % à 90 % en poids du système tensio-actif ternaireet il est représenté par un mélange binaire de :
(1) un agent tensio-actif alkyl(aryl)sulfonaté ; et
(2) un alkyl- ou alcényl succinate de formule:
Figure imgb0007
dans laquelle R1 est un radical alkyle ou alcényle ,ayant de 10 à 20 atomes de carbone , et R2 représente un atome d'hydrogène ou un groupe al kyle en Ci à C4 ;le rapport pondéral entre le sulfonate et le succinate se situant dans la gamme de 3:1 à 1:4 ; et
(c) le composant tensio-actif non ionique représente de 50 % à 10 % en poids du système tensio-actif ternaire ; ladite composition ayant un pH , mesuré dans le cas d'une solution à 1 % à 20 ° C , de 7 à 9.
2. Composition selon la revendication 1 , dans laquelle l'alkyl (aryl) sulfonate est un sel (d'acide) alkylbenzènesulfonique ayant de 10 à 18 atomes de carbone dans le groupe alkyle , le cation formateur du sel étant un cation sodium , potassium , magnésium , ammonium, monoalcanolammonium , dialcanolammonium , trialcanolammonium,ou un de leurs mélanges .
3. Composition selon la revendication 1 , dans laquelle l'alkyl- ou alcényl succinate est choisi dans le groupe formé par l'acide 2-dodécénylsuccinique , l'acide 2-tétradécénylsuccinique , l'acide 2-hexadécé- nylsuccinique , l'acide décyl succinique , l'acide dodécyl-succinique et l'acide tétradécyl succinique,et leurs sels hydrosolubles.
4. Composition selon la revendication 3 , dans laquelle le groupe alkyle ou alcényle est un fragment linéaire et dans laquelle le rapport pondéral entre le sulfonate tensio-actif et le succinate tensio-actif se situe dans la gamme de 2:1 à 1:2 .
5. Composition selon la revendication 3 , dans laquelle le composant tensio-actif non ionique représente de 15 % à 40 % en poids du système tensio-actif ternaire .
6. Composition selon la revendication 1 , qui contient de 15 % à 40 % en poids d'eau .
7. Composition selon la revendication 1 ,qui, en outre , contient de 1 % à 8 % en poids d'un acide gras en Ci o- C1 8 .
8. Composition selon la revendication 7 ,qui contient en outre de 0,01 % à 0,25 % en poids d'un antioxydant .
9. Composition selon la revendication 8 , dans laquelle l'acide gras est l'acide oléïque .
EP86200690A 1985-05-03 1986-04-23 Compositions détergentes homogènes concentrées et liquides contenant un système tensioactif ternaire Expired - Lifetime EP0200263B2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT86200690T ATE73840T1 (de) 1985-05-03 1986-04-23 Ein ternaeres oberflaechenaktives system enthaltende homogene konzentrierte fluessige reinigungsmittel.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB858511303A GB8511303D0 (en) 1985-05-03 1985-05-03 Liquid detergent compositions
GB8511303 1985-05-03

Publications (4)

Publication Number Publication Date
EP0200263A2 EP0200263A2 (fr) 1986-11-05
EP0200263A3 EP0200263A3 (en) 1989-05-10
EP0200263B1 true EP0200263B1 (fr) 1992-03-18
EP0200263B2 EP0200263B2 (fr) 1995-10-04

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EP (1) EP0200263B2 (fr)
JP (1) JPH0735517B2 (fr)
AT (1) ATE73840T1 (fr)
CA (1) CA1284446C (fr)
DE (1) DE3684355D1 (fr)
DK (1) DK167155B1 (fr)
FI (1) FI85380C (fr)
GB (1) GB8511303D0 (fr)
GR (1) GR861143B (fr)
IE (1) IE58673B1 (fr)

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US8361946B2 (en) 2004-04-08 2013-01-29 Akzo Nobel N.V. Detergent composition

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JP4955053B2 (ja) 2006-03-22 2012-06-20 ザ プロクター アンド ギャンブル カンパニー 液体処理組成物
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CN114644961A (zh) * 2014-08-01 2022-06-21 宝洁公司 包含高脂肪酸的清洁组合物

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Also Published As

Publication number Publication date
FI85380C (fi) 1992-04-10
EP0200263A3 (en) 1989-05-10
DE3684355D1 (de) 1992-04-23
EP0200263B2 (fr) 1995-10-04
DK167155B1 (da) 1993-09-06
DK203586D0 (da) 1986-05-02
IE861179L (en) 1986-11-03
CA1284446C (fr) 1991-05-28
DK203586A (da) 1986-11-04
JPH0735517B2 (ja) 1995-04-19
IE58673B1 (en) 1993-11-03
FI861846A0 (fi) 1986-05-02
JPS6225196A (ja) 1987-02-03
GR861143B (en) 1986-08-11
FI85380B (fi) 1991-12-31
GB8511303D0 (en) 1985-06-12
ATE73840T1 (de) 1992-04-15
EP0200263A2 (fr) 1986-11-05
FI861846A (fi) 1986-11-04

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