EP0586323B2 - Composition détergente et méthode pour sa fabrication - Google Patents

Composition détergente et méthode pour sa fabrication Download PDF

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Publication number
EP0586323B2
EP0586323B2 EP93500108A EP93500108A EP0586323B2 EP 0586323 B2 EP0586323 B2 EP 0586323B2 EP 93500108 A EP93500108 A EP 93500108A EP 93500108 A EP93500108 A EP 93500108A EP 0586323 B2 EP0586323 B2 EP 0586323B2
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EP
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Prior art keywords
detergent composition
formula
nonionic
ester
preferebly
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.)
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EP93500108A
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German (de)
English (en)
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EP0586323A1 (fr
EP0586323B1 (fr
Inventor
Enrique Pujol
Francisco Pujadas
Antonio Prat
Kazuhiko Okabe
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Kao Corp SA
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Kao Corp SA
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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
    • C11D1/66—Non-ionic compounds
    • C11D1/74—Carboxylates or sulfonates esters of polyoxyalkylene glycols

Definitions

  • the present invention relates to novel liquid detergent compositions which are biodegradable, non-toxic, and non-irritant, while improves its detergency, foam stability and colour protection in case of heavy and light duty detergent.
  • These detergent compositions are particulary useful to formulate shampoos, body shampoos, washing up, all purpose cleaners, heavy and light duty detergents.
  • the present invention relates to cleaning formulations comprising a specific nonionic compound.
  • the present invention relates to a method for preparing the above mentioned nonionic.
  • detergent compositions involve a combination of anionic, amphoteric and/or nonionic surfactants, in order to get better properties according to final product in terms of irritation, detergency and foam profile.
  • the nonionics employed in the detergent compositions were conventionally ethoxylated nonylphenols, C 12-18 alcohols ethoxylated with approximately 12 moles of ethylene oxides, lately C 12-15 alcohols ethoxylated with 2 to 9 moles of ethylene oxides and EO/OP derivatives.
  • US Patent 4247425 discloses the use of alkoxylated partial glycerol esters of a detergent grade fatty acid in light duty detergent compositions.
  • EP Patent 0007120 discloses an emulsifying system, to be used in a handwashing composition, mainly consisting of mono and diglycerides of higher natural fatty acids and ethoxylated glycerine esterified by fatty acids.
  • US Patent 4897214 discloses the use of monoesters of fatty acids with polyoxyethylene hexitan derivatives in skin cleaning preparations.
  • WO Patent 92/00945 discloses the use of octadienyl glycerin ethers with polyoxyethylene.
  • UK Patent 21973308 discloses the use of polyoxyalkylene alkyl- or alkenyl ethers and polyoxyalkylene glycerol fatty acid esters in detergent compositions.
  • the present inventors have carried out research on the developement of a detergent composition, which will exhibit the outstanding biodegradable, non-toxic, non-irritant performance, foam stability and better dye inhibition transfer maintaining and even improving detergency.
  • the present invention relates to a detergent compositions comprising the mono-, di- and tri-ester compounds represented by the formula (I), where the mono-di-tri-ester proportion is 46-90/9-30/1-15 wherein:
  • Ratio (I)/(II) has a value between 3 to 0.33 preferebly 1.3 to 0.75.
  • the compound mixture of the formula (I) + (II) in the present invention can be obtained by conventional method for preparating it.
  • the compound can be obtained by following the reaction processes.
  • Triglyceride which can be used in process (A) includes natural fat and oil as well as a synthetic triglyceride.
  • the fat and oil include vegetable oil such as coconut oil, palm oil, soybean oil; and animal fat and oil such as beef tallow, bone oil; aquatic animal fat and oil; hardened oils and semihardened oil thereof.
  • the compound mixture of the formula (I)+(II) can be incorporated in an amount of from 0.2% to 40%, preferebly from 3% to 20% by weight based on the whole of the detergent composition.
  • Detergency evaluation test Washing machine: Temperature: 30°C and 60°C. Dosage: 6 gr/l. Water hardness: 2 mmol/L Ca 2+ and 4 mmol/L Ca 2+ (20°HF and 40°HF). Washing load: 2kg of not soiled cotton-polyester cloth and EMPA 101,104,117 + particulated soil. No pre-washing program.
  • compositions containing the nonionic of the present invention provide a more superior colour care than usual ethoxylated alcohol.
  • Dye transfer was evaluated measuring delta E values (L 2 + a 2 + b 2 ) 1/2 by Hunter-Lab.
  • the resulting discolouration of fabrics is shown in table below: Compositions Blue Green Red 1 8.0 14.0 6.0 2 5.7 10.3 5.0 3 6.0 8.0 4.5 4 5.0 6.5 4.0 5 1.3 0.9 0.5 6 1.2 1.0 0.5
  • the nonionic from the present invention performs better than alcohol ethoxylated preventing dye transfer.
  • polyvinylpirrolidone typically dye-tranfer inhibitor.
  • the especific amount to be saved will depend on the effect of other components, that means, on formulation design. It seems to the applicant that a synergistic effect exists between the nonionic of present invention and PVP.
  • Dye transfer was evaluated measuring delta E values (L 2 + a 2 + b 2 ) 1/2 by Hunter-Lab.
  • the resulting dicoloration of fabrics is shown in table below: Compositions Blue Green Yellow 1 2.0 2.5 4.0 2 1.3 1.7 3.0 3 1.6 8.0 3.2 4 0.9 6.5 2.0 5 1.3 0.9 0.7 6 1.2 1.0 0.7
  • test 1 and 2 were corroborated using a 5 people panel, who evaluate the results according to a scale.
  • compositions containing the nonionic of the present invention prevent better the colour transfer even in HDL where the ph is neutral and no optical brighters are used. (Note that HDL were used as colour save detergents before appearing the new segment of colour saving H.D.P.D..
  • compositions containing Levenol® shows a better detergency and fat dispersion, allowing the supresion of nitrogen derivatives (alkanol amide and amine oxide) and also the complete substitution of ethoxylated alcohol. Other key point is the partial substitution of betaine.
  • the nonionic of the present invention gives also a creamy foam compared to other compositions.

Landscapes

  • 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)
  • Detergent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Claims (4)

  1. Composition détergente contenant des monoesters, diesters ét triésters, dans laquelle les proportions pondérales des monoesters, diesters et triesters valent 46-90/9-30/1-15, ces composés étant représentés par la formule (I) :
    Figure 00150001
    où B représente un atome d'hydrogène ou un groupe représenté par
    Figure 00150002
    R représentant un groupe alkyle ou alcényle en C6-22, R' représente un atome d'hydrogène ou un groupe méthyle, et chacun des indices m, n et l est, indépendamment des autres, un nombre entier valant de 0 à 40, sous réserve que m+n+1 vaille de 2 à 100, et de préférence de 9 à 19 ; et des composés représentés par la formule (II) :
    Figure 00150003
    où R' représente un atome d'hydrogène ou un groupe méthyle, et chacun des indices m, n et l est, indépendamment des autres, un nombre entier valant de 0 à 40, sous réserve que m+n+l vaille de 2 à 100, et de préférence de 9 à 19 ;
    et dans laquelle composition le rapport pondéral (I)/(II) vaut entre 3 et 0,33.
  2. Composition détergente conforme à la revendication 1, dans laquelle le rapport pondéral (I)/(II) vaut entre 1,3 et 0,75.
  3. Procédé de préparation d'une composition détergente telle que définie dans la revendication 1, par recours aux étapes suivantes (a) et (b) :
    a) on soumet un mélange de triglycérides et de glycérol à une réaction d'inter-estérification ;
    b) on soumet le mélange réactionnel issu de l'étape (a) à une réaction d'alcoxylation, en employant les oxydes d'alkylène en C2-3, en présence d'un catalyseur alcalin, pour obtenir des composés représentés par les formules générales (I) et (II).
  4. Procédé de préparation d'une composition détergente telle que définie dans la revendication 1, par recours aux étapes suivantes (c) et (d) :
    c) on fait réagir un mélange de glycérol et d'oxydes d'alkylène en C2-3, en présence d'un catalyseur alcalin ;
    d) on fait réagir le mélange réactionnel issu de l'étape (c) avec des acides gras ou des esters méthyliques d'acide gras.
EP93500108A 1992-07-20 1993-07-20 Composition détergente et méthode pour sa fabrication Expired - Lifetime EP0586323B2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP93500108A EP0586323B2 (fr) 1992-07-20 1993-07-20 Composition détergente et méthode pour sa fabrication

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP92500092 1992-07-20
EP92500092 1992-07-20
EP93500108A EP0586323B2 (fr) 1992-07-20 1993-07-20 Composition détergente et méthode pour sa fabrication

Publications (3)

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EP0586323A1 EP0586323A1 (fr) 1994-03-09
EP0586323B1 EP0586323B1 (fr) 1996-04-10
EP0586323B2 true EP0586323B2 (fr) 2005-11-02

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AT (1) ATE136579T1 (fr)
DE (1) DE69302151T3 (fr)
ES (1) ES2088254T5 (fr)

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US10045529B2 (en) 2012-06-29 2018-08-14 Ecolab Usa Inc. Quat cleaner with glycerin ether ethoxylates

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US5599785A (en) * 1993-08-04 1997-02-04 Colgate-Palmolive Co. Cleaning composition in microemulsion or liquid crystal form comprising mixture of partially esterified, fully esterified and non-esterified polyhydric alchohols
US6017868A (en) * 1993-08-04 2000-01-25 Colgate Palmolive Company Microemulsion all purpose liquid cleaning composition based on EO-PO nonionic surfactant
US5759983A (en) * 1993-08-04 1998-06-02 Colgate-Palmolive Co. Aqueous cleaning composition which may be in microemulsion form comprising polyalkylene oxide -polydimethyl siloxane and ethoxylated secondary alcohol
US5716925A (en) * 1993-08-04 1998-02-10 Colgate Palmolive Co. Microemulsion all purpose liquid cleaning compositions comprising partially esterified, fully esterified and non-esterified polyhydric alcohol and grease release agent
US5731281A (en) * 1993-08-04 1998-03-24 Colgate-Palmolive Company Microemulsion liquid crystal cleaning compositions comprising esterified and non-esterfied ethoxylated glycerol mixture and sulfoxy anionic surfactant
US5776880A (en) * 1993-08-04 1998-07-07 Colgate-Palmolive Co. Aqueous cleaning compositions which may be in microemulsion form comprising ethoxylated secondary alcohol cosurfactant
US5549840A (en) * 1993-08-04 1996-08-27 Colgate-Palmolive Co. Cleaning composition in microemulsion, liquid crystal or aqueous solution form comprising mixture of partially esterified, full esterified and non-esterified ethoxylated polyhydric alcohols
US5854193A (en) * 1993-08-04 1998-12-29 Colgate Palmolive Company Microemulsion/all purpose liquid cleaning composition based on EO-PO nonionic surfactant
US5861367A (en) * 1993-08-04 1999-01-19 Colgate Palmolive Company Cleaning and disinfecting composition in microemulsion/liquid crystal form comprising aldehyde and mixture of partially esterified, fully esterified and non-esterified polyhydric alcohols
NZ264113A (en) * 1993-08-04 1996-06-25 Colgate Palmolive Co Liquid crystal or microemulsion liquid cleaners containing esterified polyethoxyether nonionic surfactant, anionic surfactant, cosurfactant, optionally a fatty acid, and water-insoluble hydrocarbon or perfume
US5593958A (en) * 1995-02-06 1997-01-14 Colgate-Palmolive Co. Cleaning composition in microemulsion, crystal or aqueous solution form based on ethoxylated polyhydric alcohols and option esters's thereof
US5741760A (en) * 1993-08-04 1998-04-21 Colgate-Palmolive Company Aqueous cleaning composition which may be in microemulsion form comprising polyalkylene oxide-polydimethyl siloxane
WO1995014765A1 (fr) * 1993-11-22 1995-06-01 Colgate-Palmolive Company Compositions nettoyantes liquides polyvalentes en microemulsion
US5571459A (en) * 1994-02-07 1996-11-05 Colgate-Palmolive Co. Microemulsion all purpose liquid cleaning compositions
AU1925795A (en) * 1994-02-28 1995-09-11 Colgate-Palmolive Company, The Liquid detergent
ES2141862T3 (es) * 1994-05-28 2000-04-01 Goldschmidt Ag Th Concentrados acuosos fluidos de lustre perlado.
JP3266421B2 (ja) * 1994-09-13 2002-03-18 花王株式会社 低刺激性身体洗浄剤組成物
DE69533466T2 (de) * 1994-10-14 2005-09-22 Kao Corp. Flüssige Weichspülerzusammensetzung
US5767050A (en) * 1995-01-17 1998-06-16 Colgate-Palmolive Co. Light duty liquid cleaning compositions comprising partially esterified polyhydric alcohol solubilizing agent
US5476614A (en) * 1995-01-17 1995-12-19 Colgate Palmolive Co. High foaming nonionic surfactant based liquid detergent
EP0815194A1 (fr) * 1995-02-23 1998-01-07 Colgate-Palmolive Company Composition liquide pour nettoyage courant comprenant une micro-emulsion
DE19509752A1 (de) * 1995-03-17 1996-09-19 Henkel Kgaa Verfahren zur Herstellung eines pulverförmigen Waschmittels
CA2274567A1 (fr) * 1996-12-12 1998-06-18 Colgate-Palmolive Company Compositions a bras de liaison chimique
WO1998059031A1 (fr) * 1997-06-23 1998-12-30 Colgate-Palmolive Company Compositions nettoyantes liquides universelles et en microemulsion
US5866527A (en) * 1997-08-01 1999-02-02 Colgate Palmolive Company All purpose liquid cleaning compositions comprising anionic EO nonionic and EO-BO nonionic surfactants
US5858956A (en) * 1997-12-03 1999-01-12 Colgate-Palmolive Company All purpose liquid cleaning compositions comprising anionic, EO nonionic and EO-BO nonionic surfactants
PT1045021E (pt) * 1999-04-13 2004-05-31 Kao Corp Sa Composicao que inclui uma mistura de mono- di- e trigliceridos alcoxilados e glicerina
ES2185497B1 (es) * 2001-07-30 2004-03-16 Kao Corp Sa Composiciones nacarantes acuosas concentradas.
US6544938B1 (en) 2001-10-02 2003-04-08 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Soap bar comprising high levels of specific alkoxylated triglycerides which provide enhanced sensory properties and process well
ATE364741T1 (de) * 2004-05-26 2007-07-15 Boehme Chem Fab Kg Hydrophilierung von polyolefin und/oder polyester enthaltenden materialien
ES2293825B1 (es) * 2006-06-07 2008-12-16 Kao Corporation, S.A. Composicion que contiene una mezcla de mono-di, y trigliceridos y glicerina.
EP2202219A1 (fr) 2008-12-24 2010-06-30 Kao Corporation, S.A. Mélange d'amides et compositions cosmétiques comportant ce mélange
EP2497844A1 (fr) 2011-03-10 2012-09-12 Kao Corporation, S.A. Composition comprenant des esters quaternaire d'ammonium (esterquats) pour inhiber la corrosion des surfaces métalliques
CN103764611B (zh) * 2011-08-17 2016-01-20 陶氏环球技术有限责任公司 生物可再生及生物可降解表面活性剂
DK2666848T3 (en) 2012-05-22 2017-10-23 Kao Corp Sa Diluent surfactant composition
ES2701741T3 (es) 2012-06-29 2019-02-25 Ecolab Usa Inc Solfactantes de éter de glicerina etoxilada
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EP4442327A1 (fr) 2023-04-05 2024-10-09 Kao Corporation, S.A. Composition contenant un mélange de mono-, di- et triglycérides et de glycérine

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Publication number Priority date Publication date Assignee Title
US10045529B2 (en) 2012-06-29 2018-08-14 Ecolab Usa Inc. Quat cleaner with glycerin ether ethoxylates

Also Published As

Publication number Publication date
ES2088254T3 (es) 1996-08-01
ES2088254T5 (es) 2006-04-16
DE69302151T2 (de) 1996-12-05
ATE136579T1 (de) 1996-04-15
DE69302151T3 (de) 2006-06-14
EP0586323A1 (fr) 1994-03-09
DE69302151D1 (de) 1996-05-15
EP0586323B1 (fr) 1996-04-10

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