EP1806392B1 - Composés quaternaires d'esters aqueuses stables - Google Patents

Composés quaternaires d'esters aqueuses stables Download PDF

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Publication number
EP1806392B1
EP1806392B1 EP20060013688 EP06013688A EP1806392B1 EP 1806392 B1 EP1806392 B1 EP 1806392B1 EP 20060013688 EP20060013688 EP 20060013688 EP 06013688 A EP06013688 A EP 06013688A EP 1806392 B1 EP1806392 B1 EP 1806392B1
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EP
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Prior art keywords
composition
formula
weight
metal salt
esterquat
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.)
Expired - Fee Related
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EP20060013688
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German (de)
English (en)
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EP1806392A1 (fr
Inventor
Alexander Dr. Lerch
Hans Juergen Dr. Scholz
Manlio Gallotti
George Italo Pitombeira Nunes
Gustavo Kume
Claudia Barge
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Clariant Brazil SA
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Clariant Brazil 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
    • 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
    • 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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/02—Inorganic compounds ; Elemental compounds
    • C11D3/04—Water-soluble compounds
    • C11D3/046—Salts

Definitions

  • Quaternized fatty acid triethanolamine (TEA) esters and quaternized fatty acid methyldiethanolamine (MDEA) esters which are commonly called “esterquats", are widely known in detergent industry. They provide a softening effect to textile materials, especially for cotton. These compounds are made by esterification of triethanolamine (TEA) or methyldiethanolamine (MDEA) with a fatty acid and subsequent quaternisation by reacting with a short chain alkyl sulfate or alkyl chloride.
  • esterification of TEA esterquats one, two or three hydroxyl groups may react with the fatty acid and accordingly commercially available esterquat compositions contain quaternized mono-, di- and tri-esterquats. For the case of MDEA esterquats, only mono and di-esterquats are present.
  • a problem of aqueous compositions containing these Esterquats is that the Esterquats are not stable over prolonged storage since they undergo hydrolysis. In order to prevent hydrolysis it is known to add alkali metal salts ( JP 10-251 972 ).
  • the invention accordingly provides aqueous compositions consisting of an esterquat or mixtures thereof of the formula I wherein R is C 1 -C 4 -alkyl, preferably methyl, X has the same meaning as R or X is a group of the formula -C 2 H 4 OR 2 , R 1 and R 2 are independently hydrogen or a group -COR 3 , R 3 is C 7 -C 21 -alkyl or C 7 -C 21 -alkenyl and A is an anion, preferably chloride or methosulfate, and a metal salt, and optionally one or more auxiliary as defined in claim 1, which composition is free of alkali or alkaline earth metal salt, phthalocyanine metal complexes or phthalocyanine metal salts.
  • X in the formula (I) may be either an alkyl group R or a further hydroxyethyl group which may be esterified
  • the claimed compositions contain either TEA esterquats or MDEA esterquats of the following formulas II and III:
  • the group -COR 3 is preferably derived from natural occurring fatty acids such as capronic acid, caprylic acid, caprinic acid, lauric acid, myristiric acid, palmic acid, isostearic acid, stearic, oleic acid, eluidinic acid, arachinic acid, behenic acid and eruca acid.
  • Preferred acids containing the group -COR 3 are C 12 /C 18 coco fatty acids, tallow fatty acid, fully or partially hydrogenated tallow fatty acid, palm fatty acid, partially or fully hydrogenated palm fatty acid or stearic acid.
  • ester quats of formula II are present in the form of mixtures of the mono-, di- or triester of triethanolamine.
  • Preferred mixtures are those which have 10 to 38 % by weight of the monoester (R 1 and R 2 being hydrogen), 46 to 63 % by weight of the diester (R 1 being hydrogen and R 2 -COR 3 ) and 7 to 25 % by weight of the triester (R 1 and R 2 being -COR 3 ).
  • Especially preferred are also the following mixtures (all percentages are by weight):
  • esterquats of formula III are present in the form of mixtures of mono and di-ester of methyldiethanolamine.
  • Preferred mixtures are those which have from 1 to 70% by weight of monoester (R 1 being hydrogen), and from 30 to 99% by weight of the diester (R 1 being -COR 3 ).
  • Particular preferred are also the following mixtures (all percentages by weight): Monoester 2-60%; diester 35-98%, Monoester 2-40%; diester 60-98%.
  • the ester quat compositions accordingly to the present invention contain in general 0.5 to 30, preferable 2 to 24 and especially 4 to 22 % by weight of the ester quats of the formula II.
  • a salt is added which is not an alkali or alkaline earth metal salt.
  • the claimed compositions are free of such salts.
  • Preferred salts are transition metal salts, more preferably are zinc and aluminium salts such as ZnSO 4 , ZnCl 2 AlCl 3 or Al 2 (SO 4 ) 3 . These salts are present in an amount preferably from 0.002 to 10.0, preferably 0.03 to 5.0, and preferably 0.04 to 3.0 % by weight.
  • compositions according to the invention are also free of rare earth metal salts, metal salts of fatty acids or chelating agents.
  • compositions according to the present invention can be made by mixing the aqueous solution of the ester quats of formulas II and III final softener formulations with the salt.
  • the salt can be added at any moment during the softeners process preparation and either in solid form or an aqueous solution. Heating and stirring is recommended for making the claimed compositions.
  • a concentrated pre-mix containing the same molar and/or mass ratio between the ester quats and the additives can be prepared in order to be diluted up to 45 times.
  • Other ingredients such as solvent, water or any ingredient that could be part of the final formulation may be added.
  • compositions according to the invention comprise, in addition to the mentioned compounds additives and auxiliaries which are customary and specific in each case selected from electrolytes, perfumes, perfume carriers, colorants, hydrotropes, antifoaming agents, other thickening agents, opacifiers, preservatives, , anti corrosion agents, co-surfactants and solvents.
  • additives and auxiliaries which are customary and specific in each case selected from electrolytes, perfumes, perfume carriers, colorants, hydrotropes, antifoaming agents, other thickening agents, opacifiers, preservatives, , anti corrosion agents, co-surfactants and solvents.
  • the composition may be composed only of water, one or more esterquat of formula (I) and a metal salt, which composition is free of an alkali or alkali earth metal salt or phthalocyanine metal salts.
  • the metal salt preferably is ZnSO 4 , ZnCl 2 , AlCl 3 or Al 2 (SO 4 ) 3 .
  • compositions according to the invention are notable for a good storage stability and can be used as such as fabric softener or can be further diluted with water either at around room temperature or under heating .
  • ester quat used in all examples was a mixture of the following compounds:
  • ester quat ZnCl 2 crossing point (days) 1 5 % active matter - 53 2 5 % active matter 0.13 63 3 5% active matter 0.61 79 ester quat AlCl 3 crossing point (days) 4 5 % active matter 0.08 65 5 5 % active matter 0.40 69
  • compositions based on MDEA esterquats (formula III):
  • the stability profile of the formulations was monitored through storage at 45°C.
  • the hydrolysis stability profile was analysed according to the amount of mono, di and triester analysed time to time.
  • MDEA esterquats it was analysed only the amount of mono and diesterquats.
  • As hydrolysis happens the amount of monoester increases while the amount of diester decreases for both, TEA and MDEA estequarts.
  • TEA esterquats there is also a decrease on the triester amount.
  • the amount of monoester is higher than the amount of diester for TEA and MDEA esterquats and for TEA esterquats the triester is presented in low levels.
  • the crossing point of the di and monoester curves was defined as the reference for comparison between the formulations. The later the crossing point, the lower the hydrolysis rate and, consequently, the more stable the formulation.

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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)
  • Inorganic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Claims (11)

  1. Compositions aqueuses constituées d'un composé quaternaire d'ester ou de mélanges de celui-ci de la formule 1
    Figure imgb0012
     dans laquelle R représente un groupe alkyle en C1 à C4, de préférence un groupe méthyle, X a la même signification que R ou X représente un groupe de la formule -C2H4OR2, R1 et R2 représentent indépendamment un atome d'hydrogène ou un groupe -COR3, R3 représente un groupe alkyle en C7 à C21 ou un groupe alcényle en C7 à C21 et A représente un anion, de préférence un chlorure ou un méthosulfate, d' un sel métallique, et éventuellement d' un ou plusieurs auxiliaires choisis parmi le groupe constitué d'électrolytes, de parfums, d'excipients pour parfum, de colorants, d'hydrotropes, d'agents antimousses, d'épaississants, d'opacifiants, d'agents de conservation, d'agents anticorrosion, d'agents cotensioactifs et de solvants, ladite composition étant exempte de sels de métaux alcalins ou alcalino-terreux, de complexes métalliques de phtalocyanine ou de sels métalliques de phtalocyanine.
  2. Compositions aqueuses selon la revendication 1, dans laquelle le composé quaternaire d'ester est de la formule
    Figure imgb0013
     dans laquelle R, R1, R2, R3 et A sont tels que définis dans la revendication 1.
  3. Compositions aqueuses selon la revendication 1, dans laquelle le composé quaternaire d'ester est de la formule
    Figure imgb0014
     dans laquelle R, R1, R3 et A sont tels que définis dans la revendication 1.
  4. Composition selon la revendication 2, dans laquelle le composé quaternaire d'ester est de la formule II et est constitué de 10 à 38 % en poids de monoester, de 46 à 63 % en poids de diester et de 7 à 25 % en poids de triester.
  5. Composition selon la revendication 3, dans laquelle le composé quaternaire d'ester est de la formule III et est constitué de 1 à 70 % en poids de monoester et de 30 à 99 % en poids de diester.
  6. Composition selon la revendication 1, dans laquelle la quantité totale du composé quaternaire d'ester de la formule II ou de la formule III varie de 0,5 à 30 % en poids.
  7. Composition selon la revendication 1, qui contient du ZnCl2, du AlCl3, du ZnSO4 ou du Al2(SO4)3 comme sel métallique.
  8. Composition selon la revendication 1, qui contient de 0,002 à 10 % en poids du sel métallique.
  9. Composition selon la revendication 1, qui contient un ou plusieurs additifs ou auxiliaires.
  10. Composition comprenant de l'eau, un ou plusieurs composés quaternaires d'ester de la formule I telle que définie dans la revendication 1 et un sel métallique, ladite composition étant exempte de sels de métaux alcalins ou alcalino-terreux ou de sels métalliques de phtalocyanine.
  11. Composition selon la revendication 1, laquelle est un prémélange concentré du composé quaternaire d'ester et du sel métallique.
EP20060013688 2005-09-06 2006-07-01 Composés quaternaires d'esters aqueuses stables Expired - Fee Related EP1806392B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP20060013688 EP1806392B1 (fr) 2005-09-06 2006-07-01 Composés quaternaires d'esters aqueuses stables

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP05019277 2005-09-06
EP20060013688 EP1806392B1 (fr) 2005-09-06 2006-07-01 Composés quaternaires d'esters aqueuses stables

Publications (2)

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EP1806392A1 EP1806392A1 (fr) 2007-07-11
EP1806392B1 true EP1806392B1 (fr) 2008-12-24

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Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011134835A1 (fr) 2010-04-28 2011-11-03 Evonik Degussa Gmbh Composition d'adoucissant pour textile
GB201018916D0 (en) 2010-11-09 2010-12-22 Champion Technologies Ltd Corrosion inhibition
WO2013113453A1 (fr) * 2012-01-30 2013-08-08 Evonik Industries Ag Composition active d'assouplissant pour textile
US9441187B2 (en) 2012-05-07 2016-09-13 Evonik Degussa Gmbh Fabric softener active composition and method for making it
BR102014025172B1 (pt) 2013-11-05 2020-03-03 Evonik Degussa Gmbh Método para fabricação de um éster de ácido graxo de metisulfato de tris-(2-hidroxietil)-metilamônio, e composição ativa de amaciante de roupa
UA119182C2 (uk) 2014-10-08 2019-05-10 Евонік Дегусса Гмбх Активна композиція для пом'якшувача тканини
EP3208315A1 (fr) 2016-02-16 2017-08-23 Omya International AG Procédé de fabrication de produits contenant un pigment blanc
EP3208314B1 (fr) 2016-02-16 2018-08-15 Omya International AG Procédé de fabrication de produits contenant un pigment blanc
CN109208328B (zh) * 2017-07-07 2021-10-22 广州蓝月亮实业有限公司 含水织物柔软组合物
EP3444036A1 (fr) 2017-08-16 2019-02-20 Omya International AG Procédé de flotation pour la fabrication de produits contenant un pigment blanc
BR112020025643A2 (pt) 2018-07-11 2021-03-23 Clariant International Ltd. preparação e uso de esterquats de alta qualidade a partir de ácidos graxos de farelo de arroz
EP4274881A1 (fr) 2021-01-11 2023-11-15 Clariant International Ltd Esterquats hydrogénés à partir d'acides gras de son de riz et leur préparation

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Publication number Priority date Publication date Assignee Title
JPH10251972A (ja) 1997-03-11 1998-09-22 Lion Corp カチオン界面活性剤の加水分解抑制剤、及びカチオン界面活性剤組成物
NZ331196A (en) * 1997-08-15 2000-01-28 Ciba Sc Holding Ag Water soluble fabric softener compositions comprising phthalocyanine, a quaternary ammonium compound and a photobleaching agent
DE19756679A1 (de) * 1997-12-19 1999-07-01 Henkel Ecolab Gmbh & Co Ohg Textilbehandlungsmittel zur Hydrophobierung von textilen Oberflächen
DE19904513A1 (de) * 1999-02-04 2000-08-10 Cognis Deutschland Gmbh Detergensgemische

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EP1806392A1 (fr) 2007-07-11
ES2317370T3 (es) 2009-04-16

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