WO2023126286A1 - Hydrotropes amphotères multifonctionnels, formulations de nettoyage les contenant et leur utilisation - Google Patents

Hydrotropes amphotères multifonctionnels, formulations de nettoyage les contenant et leur utilisation Download PDF

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Publication number
WO2023126286A1
WO2023126286A1 PCT/EP2022/087371 EP2022087371W WO2023126286A1 WO 2023126286 A1 WO2023126286 A1 WO 2023126286A1 EP 2022087371 W EP2022087371 W EP 2022087371W WO 2023126286 A1 WO2023126286 A1 WO 2023126286A1
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Prior art keywords
acid
agents
linear
carbon atoms
branched
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PCT/EP2022/087371
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English (en)
Inventor
Hanamanthsa Shankarsa Bevinakatti
Sorel MURESAN
Karen Lee White
Kevin Michael SALMON
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Nouryon Chemicals International B.V.
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Priority to EP22843722.4A priority Critical patent/EP4457208A1/fr
Priority to CN202280081798.XA priority patent/CN118382609A/zh
Publication of WO2023126286A1 publication Critical patent/WO2023126286A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C229/24—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having more than one carboxyl group bound to the carbon skeleton, e.g. aspartic acid
    • 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
    • C11D1/88—Ampholytes; Electroneutral compounds
    • C11D1/90—Betaines
    • 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
    • C11D1/88—Ampholytes; Electroneutral compounds
    • C11D1/94—Mixtures with anionic, cationic or non-ionic compounds

Definitions

  • the present disclosure relates to multifunctional hydrotropes and the use thereof in cleaning applications.
  • amphoteric surfactants known in the prior art include alkylamine dipropionic acids and their salts.
  • Alkylamine dipropionic acid products are commercially available from Nouryon (under the tradename AMPHOLAK®) and other producers. In these products, these amphoteric surfactants serve as good hydrotropes, particularly where the alkyl group is ⁇ Cl 2.
  • these alkylamine dipropionic acids suffer from the drawback that they are prepared using acrylic acid, which is not bio-based. As a result, products containing these amphoteric surfactants have a low renewable carbon index (RCI).
  • amphoteric surfactants in use include ampho acetates made using monochloro acetic acid, preferably its sodium salt. They can be made using mono-, di-, tri-, and tetramines and are commercially available from Nouryon under the tradename AMPHOLAK®.
  • ampho acetates yield undesired NaCl as a byproduct. The presence of NaCl, an electrolyte, lowers the cloud point in the formulations, which is disadvantageous.
  • such products derived from tri- and tetramines are not readily biodegradable.
  • Alkylamine dipropionic acids can be synthesized by reacting a primary fatty amine with acrylic acid via a Michael addition reaction.
  • the product can be made/isolated either in its acid form or as a mono or disodium sodium salt by adding NaOH.
  • Itaconic acid methylenebutanedioic acid, methylenesuccinic acid
  • Ri represents a fatty linear or branched, saturated or unsaturated alkylene group having 8-30 carbon atoms
  • R2 represents a linear or branched, saturated or unsaturated lower alkylene group having 1-8 carbon atoms; n represents 0 or 1 ;
  • Xi, X2, and X3 independently represent a negative charge or a counterion.
  • Compounds wherein one or more of Xi, X2, and X3 represent H are also contemplated, particularly those wherein one of Xi and X2 represents H and the other represents a negative charge or a counterion.
  • the present disclosure relates in another embodiment to a process for preparing a compound according to any one of claims 1-6, said process comprising:
  • the present disclosure relates in another embodiment to an aqueous cleaning composition
  • an aqueous cleaning composition comprising:
  • the present disclosure relates in yet another embodiment to a method of cleaning an object to be cleaned comprising contacting the object with an aqueous cleaning composition as described herein.
  • FIG. 1A is an illustration depicting the cleaning power of ARMEEN® 1M1214D itaconate (C12-14 alkyl methyl amine itaconate) versus the control “A” (BEROL® R648 NG (quaternary C12-14 alkyl methyl amine ethoxylate methyl chloride)) in the absence of NaOH on a plate soiled with engine grease; and
  • FIG. IB is an illustration depicting the cleaning power of ARMEEN® 1M1214D itaconate versus the control “C” (BEROL® R648 NG) in the presence of 2% NaOH on another plate soiled with engine grease.
  • the compound of formula (I) can be derived from any multicarboxylic acid containing a carbon-carbon double bond.
  • the compound of formula (I) is derived from a multicarboxylic acid of the formulae:
  • the multicarboxylic acid is selected from the group consisting of itaconic acid, methylidenemalonic acid, methylideneglutaric acid, maleic acid, fumaric acid, citraconic acid, and mesaconic acid.
  • the carboxylic acid functionality can be partially or completely neutralized in Xi, X2, X3 etc., with any suitable cations, especially, an alkaline (earth) metal ion, such as Mg 2+ , Ca 2+ , NH 4 + , K + or Na + , especially sodium and potassium, most preferably sodium, or an alkanolamine, such as methanolamine, monoethanolamine (MEA), diethanolamine (DEA) triethanolamine (TEA), 2-amino-2-methyl-l -propanol (AMP), tris(hydroxymethyl)aminomethane (TRIS), or 2-(isopropylamino)ethanol (IPAE).
  • an alkaline (earth) metal ion such as Mg 2+ , Ca 2+ , NH 4 + , K + or Na + , especially sodium and potassium, most preferably sodium
  • an alkanolamine such as methanolamine, monoethanolamine (MEA), diethanolamine (DEA) triethanolamine (TEA), 2-
  • Neutralization can be conducted using neutralization methods well known in the art, for example, reaction with sodium hydroxide or other suitable neutralizing agents.
  • the compound of formula (I) is also derived from a secondary amine of the formula: wherein
  • Ri represents a fatty linear or branched, saturated or unsaturated alkylene group having 8-14 carbon atoms
  • R2 represents a linear or branched, saturated or unsaturated lower alkylene group having 1-3 carbon atoms.
  • the secondary amine is selected from the group consisting of octylmethylamine, cocoalkylmethylamine, laurylmethylamine, n- decylmethylamine, tallowalkylmethylamine, soyaalkylmethylamine, oleylalkylamine and C 12/ 14alkylmethy lamine.
  • the compound of formula (I) has the formula: wherein
  • Ri represents a fatty linear or branched, saturated or unsaturated alkylene group having 12 or 14 carbon atoms
  • Xi and X2 independently represent a negative charge or a counterion.
  • At least one of Xi or X2 is a sodium cation.
  • one of Xi and X2 represents H and the other represents a negative charge or a counterion, especially sodium.
  • the compound of the formula (I) is prepared by a process comprising:
  • the secondary amine is added to a reaction mixture containing the multicarboxylic acid.
  • the multicarboxylic acid is added to a reaction mixture containing the secondary amine.
  • the neutralization of the multicarboxylic acid can be carried out either before (preneutralization) the reaction with the secondary amine or afterwards (post- neutralization).
  • the reaction is carried out in the absence of NaOH, leading to acid product characterized by the presence of COOH groups.
  • the reaction is carried out using 1 equivalent of NaOH, giving rise to monosodium salts.
  • the reaction is carried out using 2 equivalents of NaOH, giving rise to disodium salts.
  • the present disclosure seeks to cover any degree of partial neutralization, i.e., from unneutralized, to any extent of partial neutralization, to completely neutralized.
  • the product is a monosodium salt.
  • the reaction mixture will contain water alone or a mixture of water and suitable organic solvent, for example, an alcohol, such as ethanol or methanol, or a glycol such as ethylene glycol, monopropylene glycol (MPG) or glycerol, with MPG being most preferred, followed by glycerol.
  • suitable organic solvent for example, an alcohol, such as ethanol or methanol, or a glycol such as ethylene glycol, monopropylene glycol (MPG) or glycerol, with MPG being most preferred, followed by glycerol.
  • the amount of solvent is preferably 0-80 wt% of the reaction mixture, most preferably 40-60 wt%.
  • the solvent is removed from the product.
  • the solvent is not removed and is, therefore, present in the product.
  • the temperature can range from 25-110°C, or higher, depending on the reactants.
  • itaconic acid and ARMEEN® 1M1214D reactions carried at temperatures greater than 110°C lead to side products and, therefore, the temperature should be kept lower.
  • temperatures lower than 70 °C lead to long reaction times and incomplete reactions.
  • the reaction with itaconic acid and ARMEEN® 1M1214D is carried out at 70-85°C for up to 10 hours.
  • the process of the reaction can be monitored using IR and/or Raman spectroscopy, or HPLC. Purity and composition of the resultant product can be analyzed using Hl and Cl 3 NMR, or LC-MS.
  • the active% of the product is preferably 20-100%, most preferably 40-60%.
  • Cleaning formulations containing the disclosed compounds are useful for a variety of cleaning purposes, for example, they can be formulated for, household cleaning, industrial cleaning, all-purpose cleaning, car washing, acidic and caustic cleaning, deck and floor cleaning, hard surface cleaning, metal cleaning, food & beverage cleaning, automated and manual dishwash, laundry detergents and the like.
  • the cleaning formulations may contain, in addition to the disclosed compounds of formula (I) and water, other conventional ingredients well known in the art of cleansing.
  • the cleaning composition comprises one or more nonionic surfactants.
  • the one or more nonionic surfactants are selected from the group consisting of nonionic alkylene oxide adducts, especially C8-C18-linear and branched alcohol (alcohol alkoxylates) and amine alkoxylates comprising 1-20 ethyleneoxy units and 0-5 propyleneoxy units.
  • nonionic alkyl polyglyceryl ethers made using C8- C18-linear and branched alcohol and 1-10 glycidol units or alkyl polyglycerylamines made using C8-C18-linear and branched alkyl amine and 1-10 glycidol units can also be used.
  • nonionic alkylene oxide adducts are well known conventional products wherein the molecule comprises a hydrophobic moiety and a moiety containing alkyleneoxy units, said latter moiety having a hydrophilic character.
  • the disclosure relates to the use of compounds of formula (I) as hydrotropes for nonionic surfactants in aqueous solutions.
  • the disclosure relates to the improved solubilization of nonionic surfactants to make compositions with a good cleaning performance wherein water, a nonionic surfactant, a compound having the formula (I) as defined above, and other optional ingredients are combined and/or mixed in one or several steps.
  • the amounts of the components are suitably: a) at least 0.05% by weight, preferably at least 0.5% by weight, and at most 20% by weight, preferably at most 15% by weight, and most preferably at most 10% by weight, of alcohol alkoxylate, b) at least 0.02% by weight, preferably at least 0.1% by weight, and at most 20% by weight, preferably at most 15% by weight, and most preferably at most 10% by weight, of compound of formula (I), and c) 0% by weight, preferably at least 0.05% by weight, and at most 30% by weight, preferably at most 20% by weight, more preferably at most 15% by weight, and most preferably at most 10% by weight, of alkali hydroxides, alkaline builders and/or alkaline complexing agents.
  • compositions contain alkali hydroxides, alkaline builders and/or alkaline complexing agents.
  • nonionic surfactants preferably have the formula:
  • the C8-C18-alcohol alkoxylates may also contain up to 5 propyleneoxy units.
  • the number of propyleneoxy units, when present, may be as small as 0.1 mole PO per mole alcohol.
  • the ethyleneoxy units and the propyleneoxy units may be added randomly or in blocks.
  • the blocks may be added to the alcohol in any order.
  • the alkoxy lates may also contain an alkyl group with 1-4 carbon atoms in the end position.
  • the alkoxylates contain 2-8 ethyleneoxy units and 0-2 propyleneoxy units.
  • the alkyl group of the nonionic surfactants may be linear or branched, saturated or unsaturated.
  • Suitable linear nonionic surfactants are C9-C11 alcohol + 4, 5, 6, 7 or 8 moles of EO, C8-C10 alcohol + 3, 4, 5, 6, 7 or 8 moles of EO, C12-C14 alcohol + 3, 4, 5, 6, 7 or 8 moles of EO and C10-C14 alcohol + 8 moles of EO + 2 moles of PO.
  • Suitable branched nonionic surfactants are 2-ethylhexanol + 3, 4 or 5 moles of EO, 2-ethylhexanol + 2 moles of PO + 4, 5 or 6 moles of EO, 2- propylheptanol + 3, 4, 5 or 6 moles of EO and 2-propylheptanol + 1 mole of PO + 4 moles of EO, C9 or Cll alcohol + 4, 5, 6, 7 or 8 moles of EO, tridecyl alcohol + 4, 5, 6, 7 or 8 moles of EO,.
  • Another example is 2-butyloctanol + 5, 6 or 7 moles of EO. Wherever the degree of alkoxylation is discussed, the numbers represent molar average numbers.
  • compositions may be acidic, neutral or alkaline.
  • Alkaline compositions are typically based on alkali hydroxides, alkaline builders and/or complexing agents. The alkaline compositions are especially preferred.
  • the alkali hydroxides preferably are sodium or potassium hydroxide.
  • the alkaline builders may be an alkali carbonate or an alkali hydrogen carbonate, such as sodium carbonate, potassium carbonate, sodium hydrogen carbonate or potassium hydrogen carbonate, an alkali salt of a silicate, such as sodium silicate or sodium metasilicate, or alkali salts of phosphates, such as sodium orthophosphate.
  • Alkaline builders that act through complexation are, e.g., sodium pyrophosphate and sodium tripolyphosphate and the corresponding potassium salts.
  • the builder/complexing agent may also be organic.
  • organic builders/complexing agents are aminocarboxylates, such as Glutamic acid, N,N- diacetate (GLDA), Methylglycine, N,N-diacetate (MGDA), sodium nitrilotriacetate (Na3NTA), sodium ethylenediamine tetraacetate (EDTA), sodium diethylenetriamine pentaacetate, sodium 1,3 -propylenediamine tetraacetate, and sodiumhydroxyethylethylenediamine triacetate; aminopolyphosphonates, such as nitrilotrimethylene phosphonate; organic phosphates; polycarboxylates, such as citrates; and alkali salts of gluconic acid, such as sodium or potassium gluconates.
  • aminocarboxylates such as Glutamic acid, N,N- diacetate (GLDA), Methylglycine, N,N-diacetate (MGDA), sodium nitrilotriacetate (Na3NT
  • complexing and/or pH adjusting agents may also be added, such as citric acid, oxalic acid, acetic acid, sulfamic acid, hydrochloric acid.
  • the cleaning composition comprises one or more chelates.
  • the chelate is at least one aminocarboxylate chelate selected from the group consisting of methylglycinediacetic acid (MGDA), N,N-dicarboxymethyl glutamic acid (GLDA), N-hydroxyethyliminodiacetic acid, nitrilotriacetic acid (NTA), ethylenediaminetetraacetic acid (EDTA), N-hydroxyethyl-ethylenediaminetriacetic acid (HEDTA), diethylenetriaminepentaacetic acid (DTP A), ethylenediaminetetraproprionic acid triethylenetetraaminehexaacetic acid (TTHA), tetracetyl ethylene diamine (TAED), iminodisuccinic acid (IDS), ethanol diglycine (EDG), and the respective alkali metal, ammonium and substituted ammonium salts thereof.
  • the MGDA methylglycinediacetic acid
  • GLDA N
  • the chelate is a non-aminocarboxylate chelate containing carboxylate functionality but not a nitrogen atom.
  • the non- aminocarboxylate chelate is a divalent or higher valency carboxylic acid.
  • the non-aminocarboxylate chelate is at least one member selected from the group consisting of citric acid, isocitric acid, 2,3 hydroxycitric acid, tricarballylic acid, ethanetricarboxylic acid (HETA), aconitic acid, succinic acid, maleic acid, fumaric acid, oxaloacetic acid, ketoglutaric acid, butanetetracarboxylic acid, polycarboxylic acid, and the respective alkali metal, ammonium and substituted ammonium salts thereof.
  • the non-aminocarboxylate chelate is selected from the group consisting of citric acid and salts thereof.
  • one or more chelates are present in the formulation, they are present in a total combined chelate amount of greater than 0% by weight, preferably at least 0.05% by weight, most preferably at least 1% by weight, and at most 30% by weight, preferably at most 20% by weight, more preferably at most 15% by weight, and most preferably at most 10% by weight.
  • adjunct ingredients When one or more adjunct ingredients are present in the formulation, they are present in a total combined adjunct ingredient amount of greater than 0% by weight, preferably at least 0.05% by weight, most preferably at least 1% by weight, and at most 30% by weight, preferably at most 20% by weight, more preferably at most 15% by weight, and most preferably at most 10% by weight.
  • the present disclosure contemplates both diluted and concentrated compositions.
  • Diluted compositions of the present disclosure are clear and stable.
  • the clarity interval suitably is between 0-40°C, preferably between 0-50°C, and most preferably between 0-60 °C. This may be adapted by changing the ratio of hydrotrope to nonionic surfactant.
  • the diluted compositions normally contain at least 80% by weight of water, suitably at least 90% by weight, and normally at most 99.5% by weight of water, suitably at most 98% by weight.
  • Concentrated compositions of the present disclosure are clear and stable.
  • the clarity interval suitably is between 0-40°C, preferably between 0-50°C, and most preferably between 0-60 °C. This may be adapted by changing the ratio of hydrotrope to nonionic surfactant.
  • the concentrate normally contains at least 50% by weight of water, suitably at least 70% by weight, and normally at most 95% by weight of water, suitably at most 90% by weight.
  • Example 1 ARMEEN® 1M1214D Monosodium Itaconate
  • ARMEEN® 1M1214D monosodium itaconate can be prepared according to the following synthesis scheme:
  • ARMEEN® 1M1214D monosodium itaconate can be prepared as follows:
  • IR infrared spectra
  • Step-2 Once the reaction is complete, water is added to the reaction mixture followed by slow addition of 50% NaOH solution from a disposable pipette keeping the reaction mixture temperature ⁇ 80°C. The reaction mixture is well stirred after the addition and the product is transferred to ajar.
  • IR infrared spectra
  • Step-2 Once the reaction shows completion, water and aq. NaOH are added and the reaction mixture is stirred at ⁇ 70°C until the hydrolysis shows completion as monitored by IR for the disappearance of the ester carbonyl, at which time the product is transfer to ajar.
  • Step- 1 Fumaric acid and water were added to a 100 ml 3 -neck RB flask immersed in an oil batch fitted with magnetic stirrer, thermometer, N2 inlet and a reflux condenser, and stirred at room temperature under N2 sparging. NaOH was added to the stirred fumaric acid solution and stirred well (exothermic). Once the reaction mixture became clear, MPG was added to the reaction mixture and the reaction temperature was set to 75 °C and IR taken once the reaction mixture became clear again.
  • amphoteric surfactants can be made from the following combinations of secondary amines and multicarboxylic acids: Example 5
  • BEROL® R648 NG (Nouryon) is a market leading product for cleaning formulations that afford best-in-class cleaning, from a renewable, vegetable source with low or no environmental persistence and ecotoxicity and ideally non-label as-sold.
  • BEROL® R648 NG is readily biodegradable, it has certain drawbacks such as, it is an ethoxylate (not dioxane- free), is a quat, and has low RCI (Renewable Carbon Index) of 29%.
  • RCI Renewable Carbon Index
  • ARMEEN® 1M1214D itaconate meets all the criteria mentioned above with performance as good as the benchmark BEROL® R648 NG. ARMEEN® 1M1214D itaconate is expected to be readily biodegradable with high RCI (-95%), low/no toxicity, and cleaning performance as good as the benchmark BEROL® R648 NG.
  • Test formulations A and B comprised 5% BEROL® 260, 8% DISSOLVINE® GL-47-S, and either 4% BEROL® R648 NG or 2.4% ARMEEN® 1M1214D itaconate, respectively.
  • Test formulations C and D comprised 5% BEROL® 260, 8% DISSOLVINE® GL-47-S, 2% NaOH, and either 4% BEROL® R648 NG or 2.4% ARMEEN® 1M1214D itaconate, respectively.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Detergent Compositions (AREA)

Abstract

La présente divulgation concerne un composé de formule (I) dans laquelle R1 représente un groupe alkylène linéaire ou ramifié, saturé ou insaturé ayant de 8 à 30 atomes de carbone; R2 représente un groupe alkylène inférieur saturé ou insaturé, linéaire ou ramifié, ayant de 1 à 8 atomes de carbone; n représente 0 ou 1; Z et Y représentent indépendamment une liaison ou un groupe alkylène inférieur linéaire ou ramifié ayant de 1 à 8 atomes de carbone éventuellement substitué par un ou plusieurs groupes COOX3; et X1, X2 et X3 représentent indépendamment une charge négative ou un contre-ion. Le composé de formule (I) agit comme hydrotrope et est utile pour des applications de nettoyage. Des procédés de préparation du composé, des compositions de nettoyage contenant le composé et des procédés d'utilisation du composé pour nettoyer un objet sont également divulgués.
PCT/EP2022/087371 2021-12-28 2022-12-21 Hydrotropes amphotères multifonctionnels, formulations de nettoyage les contenant et leur utilisation WO2023126286A1 (fr)

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EP22843722.4A EP4457208A1 (fr) 2021-12-28 2022-12-21 Hydrotropes amphotères multifonctionnels, formulations de nettoyage les contenant et leur utilisation
CN202280081798.XA CN118382609A (zh) 2021-12-28 2022-12-21 多官能两性水溶助剂、含有其的清洁制剂及其用途

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20170313920A1 (en) * 2010-10-06 2017-11-02 Thomas P. Daly Biological Buffers with Wide Buffering Ranges
EP3913041A1 (fr) * 2020-05-20 2021-11-24 Beratherm AG Solution aqueuse de nettoyage permettant d'éliminer des restes de protéines, d'enzymes, d'huile de silicone et de gras ainsi que son utilisation

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20170313920A1 (en) * 2010-10-06 2017-11-02 Thomas P. Daly Biological Buffers with Wide Buffering Ranges
EP3913041A1 (fr) * 2020-05-20 2021-11-24 Beratherm AG Solution aqueuse de nettoyage permettant d'éliminer des restes de protéines, d'enzymes, d'huile de silicone et de gras ainsi que son utilisation

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
PALICKA JADWIGA: "Amphoterics in household detergents", JOURNAL OF CHEMICAL TECHNOLOGY AND BIOTECHNOLOGY, vol. 50, no. 3, 1 January 1991 (1991-01-01), Hoboken, USA, pages 331 - 349, XP093037706, ISSN: 0268-2575, DOI: 10.1002/jctb.280500305 *

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