EP0722435A1 - Sels quaternaires d'esters de triethanolamine d'acide gras presentant une hydrosolubilite amelioree - Google Patents

Sels quaternaires d'esters de triethanolamine d'acide gras presentant une hydrosolubilite amelioree

Info

Publication number
EP0722435A1
EP0722435A1 EP94928843A EP94928843A EP0722435A1 EP 0722435 A1 EP0722435 A1 EP 0722435A1 EP 94928843 A EP94928843 A EP 94928843A EP 94928843 A EP94928843 A EP 94928843A EP 0722435 A1 EP0722435 A1 EP 0722435A1
Authority
EP
European Patent Office
Prior art keywords
fatty acid
acid
carbon atoms
alkyl
triethanolamine
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.)
Withdrawn
Application number
EP94928843A
Other languages
German (de)
English (en)
Inventor
Nuria Bonastre
Joaquim Bigorra Llosas
Rafael Pi Subirana
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.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
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 Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP0722435A1 publication Critical patent/EP0722435A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/12—Preparations containing hair conditioners
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/45—Derivatives containing from 2 to 10 oxyalkylene groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
    • C07C217/08—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C219/02—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C219/04—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C219/06—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having the hydroxy groups esterified by carboxylic acids having the esterifying carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C219/02—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C219/04—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C219/08—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the hydroxy groups esterified by a carboxylic acid having the esterifying carboxyl group bound to an acyclic carbon atom of an acyclic unsaturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/18—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
    • 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
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/001—Softening compositions
    • C11D3/0015—Softening compositions liquid
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/46—Compounds containing quaternary nitrogen atoms
    • D06M13/463—Compounds containing quaternary nitrogen atoms derived from monoamines
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material

Definitions

  • the invention relates to quaternized fatty acid triethanolamine ester salts (“esterquats”) with improved water solubility, which are obtained by esterifying selected mixtures of linear and branched fatty acids with a triethanolamine component and then quaternizing them in a manner known per se to process their production, the use of the new ester quats for the production of surface-active agents and the use of the fatty acid mixtures for the production of water-soluble ester quats.
  • esterquats quaternized fatty acid triethanolamine ester salts
  • Quaternized fatty acid triethanolamine ester salts are cationic surfactants which, due to their excellent softening performance and their high ecotoxicological compatibility, are becoming increasingly important.
  • esterquats are cationic surfactants which, due to their excellent softening performance and their high ecotoxicological compatibility, are becoming increasingly important.
  • the esterquats are usually prepared in a two-stage process, in which triethanolamine is first partially esterified with fatty acids and the reaction product is then quaternized in isopropyl alcohol with methyl chloride or preferably diethyl sulfate.
  • low-viscosity concentrates of the ester quats in isopropyl alcohol can be produced which have a solids content of up to 85% by weight.
  • odorlessly flawless, i.e. H. non-alcoholic products required.
  • commercially available ester quats are solid, a fact which is detrimental to their processability.
  • Another disadvantage is that the known anhydrous ester quats from the market are difficult to disperse in water and, in particular, the preparation of concentrates is not possible without the addition of auxiliaries.
  • the object of the invention was to provide novel ester quats which are low-viscosity in anhydrous form, can be easily processed into aqueous concentrates and have advantageous performance properties. Description of the invention
  • the invention relates to quaternized fatty acid triethanolamine ester salts with improved water solubility of the formula (I),
  • R2 and R3 independently of one another for hydrogen or R -'- CO
  • R ⁇ for an alkyl radical with 1 to 4 carbon atoms or a (CH2CH2 ⁇ ) gH group, m, n and p in total for 0 or numbers from 1 to 12, q for numbers from 1 to 12 and
  • esterquats based on branched fatty acids prove to be low-viscosity, but do not show a soft grip.
  • esterquats based on linear fatty acids are characterized by good softening properties, but are simultaneously however, they are solid in the anhydrous state and are not readily dispersible.
  • starting materials for the production of esterquats are available within a narrowly limited mixing ratio between linear and branched fatty acids, which are free-flowing in a water-free state and highly water-soluble.
  • the new ester quats have advantageous application properties and can be used e.g. B. Process to fabric softener multiple concentrates low viscosity.
  • Another object of the invention relates to a process for the preparation of quaternized fatty acid triethanolamine ester salts with improved water solubility, in which fatty acid mixtures containing
  • Component a) includes, for example, caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmoleic acid, stearic acid, oleic acid, elaidic acid, petroselic acid, linoleic acid, linolenic acid, elaeostearic acid, ricinoleic acid, 12-hydroxystearic acid, arachinic acid, arachinic acid, acid, behenic acid and erucic acid and their technical mixtures, such as those used in the pressure splitting of fats and oils, for example palm oil, palm kernel oil, coconut oil, sunflower and rapeseed oil from old and new varieties, olive oil, cottonseed oil, peanut oil and meadowfoam oil , Castor oil, lard oil and beef tallow.
  • fats and oils for example palm oil, palm kernel oil, coconut oil, sunflower and rapeseed oil from old and new varieties, olive oil, cottonseed oil, peanut oil
  • component a in a special embodiment of the invention, mixtures a of new sunflower fatty acid and palm fatty acid in a weight ratio of 40:60 to 60:40, preferably 50:50, are therefore used as component a).
  • Component b) includes branched fatty acids such as 2-ethylhexanoic acid, isotridecanoic acid, isopalmitic acid and / or isostearic acid.
  • branched fatty acids such as 2-ethylhexanoic acid, isotridecanoic acid, isopalmitic acid and / or isostearic acid.
  • the preferred ratio between linear and branched fatty acids is in the range from 50:50, in particular 45:50 to 55: 45 parts by weight.
  • the esterification of the fatty acids with the triethanolamine or the ethylene oxide adduct with triethanolamine can be carried out in a manner known per se.
  • the fatty acids and the triethanolamine component can usually be used in a molar ratio of 1.2: 1 to 1.9: 1, preferably 1.4: 1 to 1.8: 1.
  • Particularly suitable esterification catalysts are hypophosphorous acid or its alkali metal salts.
  • the quaternization is preferably carried out in a manner known per se using alkyl halides, alkyl sulfates, alkyl phosphates or alkylene oxides.
  • alkyl halides alkyl sulfates, alkyl phosphates or alkylene oxides.
  • methyl chloride, dimethyl sulfate or ethylene oxide is preferred.
  • isopropyl alcohol can be used, which is removed after the reaction is complete.
  • the ester quats can be bleached with hydrogen peroxide and stabilized by adding antioxidants.
  • esterquats according to the invention are flowable in the anhydrous state and can be processed into aqueous concentrates with an active substance content of up to 50, preferably 20 to 35% by weight. They show good anti-aging and anti-static properties.
  • Another object of the invention therefore relates to their use for the production of surface-active agents, for example washing, rinsing, cleaning and conditioning agents, and products for hair and body care, in which they are present in amounts of 1 to 50, preferably 5 to 30,% by weight .-% - based on the funds - may be included.
  • a final object of the invention finally relates to the use of fatty acid mixtures containing
  • the fatty acid mixtures A to D are according to the invention, the fatty acids E to H are used for comparison. II. Manufacturing Examples
  • Solubility and viscosity of the ester quats were assessed in the water-free state and in a 32% by weight dilution.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Dermatology (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Textile Engineering (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Materials Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

L'invention concerne des sels quaternaires d'esters de triéthanolamine d'acide gras de la formule (I), dans laquelle R1CO représente, dans une proportion de 40 à 60 % en poids, un reste acyle linéaire ayant 6 à 22 atomes de carbone, et, dans une proportion de 60 à 40 % en poids, un reste acyle ramifié ayant 6 à 22 atomes de carbone; R2 représente un groupe alkyle ayant 1 à 4 atomes de carbone ou bien un groupe (CH¿2?CH2O)qH; m, n et p valent au total 0 ou bien représentent un nombre compris entre 1 et 12; q représente un nombre compris entre 1 et 12; et X représente halogénure, sulfate d'alkyle ou phosphate d'alkyle. Ces sels sont coulants lorsqu'ils sont exempts d'eau et on peut les traiter pour obtenir des concentrés solubles donnant des solutions claires, concentrées, dont la teneur en solides peut atteindre 50 % en poids. De tels sels conviennent parfaitement à la production d'agents tensioactifs.
EP94928843A 1993-10-08 1994-09-29 Sels quaternaires d'esters de triethanolamine d'acide gras presentant une hydrosolubilite amelioree Withdrawn EP0722435A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE4334365 1993-10-08
DE4334365A DE4334365A1 (de) 1993-10-08 1993-10-08 Quaternierte Fettsäuretriethanolaminester-Salze mit verbesserter Wasserlöslichkeit
PCT/EP1994/003253 WO1995010500A1 (fr) 1993-10-08 1994-09-29 Sels quaternaires d'esters de triethanolamine d'acide gras presentant une hydrosolubilite amelioree

Publications (1)

Publication Number Publication Date
EP0722435A1 true EP0722435A1 (fr) 1996-07-24

Family

ID=6499728

Family Applications (1)

Application Number Title Priority Date Filing Date
EP94928843A Withdrawn EP0722435A1 (fr) 1993-10-08 1994-09-29 Sels quaternaires d'esters de triethanolamine d'acide gras presentant une hydrosolubilite amelioree

Country Status (5)

Country Link
US (1) US5886201A (fr)
EP (1) EP0722435A1 (fr)
JP (1) JPH09503513A (fr)
DE (1) DE4334365A1 (fr)
WO (1) WO1995010500A1 (fr)

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WO1995033379A2 (fr) * 1994-06-02 1995-12-14 Kao Corporation Renforçateurs d'efficacite pour produits chimiques agricoles et leur procede d'utilisation
GB2310851A (en) * 1996-03-05 1997-09-10 Procter & Gamble Cationic detergent compounds
DE19611623C2 (de) * 1996-03-25 1998-05-28 Henkel Kgaa Verfahren zur Herstellung von Esterquats
US5939059A (en) * 1997-08-13 1999-08-17 Akzo Nobel Nv Hair conditioner and 2 in 1 conditioning shampoo
DE19753792A1 (de) * 1997-12-04 1999-06-10 Henkel Kgaa Verfahren zum Entschäumen von Treibstoffen
AU2105999A (en) * 1998-01-09 1999-07-26 Witco Corporation Novel quaternary ammonium compounds, compositions containing them, and uses thereof
DE19856003A1 (de) * 1998-12-04 2000-06-08 Cognis Deutschland Gmbh Verfahren zur Herstellung von hochviskosen Esterquatzubereitungen
ES2168913B1 (es) * 1999-10-06 2003-10-01 Union Derivan S A Esterquats que no requieren aditivos modificadores de la viscosidad y su procedimiento de obtencion.
US6271185B1 (en) 1999-10-29 2001-08-07 Cargill, Incorporated Water soluble vegetable oil esters for industrial applications
DE19962874A1 (de) * 1999-12-24 2001-06-28 Cognis Deutschland Gmbh Transparente Avivagemittel
EP1181003B1 (fr) 2000-03-29 2007-03-14 Croda, Inc. Acides gras quaternaires a base de composes ante-iso
DE10028453B4 (de) * 2000-06-08 2013-06-27 Cognis Ip Management Gmbh Esterquatmischungen
US6800716B2 (en) * 2001-08-20 2004-10-05 Alzo International Polymeric urethane ester quats and their use in personal care compositions
US6946567B2 (en) * 2002-04-02 2005-09-20 Akzo Nobel N.V. Skeletal isomerization of alkyl esters and derivatives prepared therefrom
US20050176609A1 (en) * 2002-05-13 2005-08-11 Ferdinand Naef Branched fatty acid derivatives as anti-gelling or viscosity-control ingredients
US20040087473A1 (en) * 2002-11-05 2004-05-06 Colgate-Palmolive Company Aqueous composition comprising oligomeric esterquats
US6881716B2 (en) * 2002-11-01 2005-04-19 Colgate-Palmolive Company Aqueous composition comprising oligomeric esterquats
EP1491617B1 (fr) * 2003-06-24 2006-09-27 Cognis IP Management GmbH Compositions aqueuses nacrées
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EP1964833B1 (fr) * 2007-03-02 2012-08-08 Cognis IP Management GmbH Tensioactifs cationiques asymétriques
RU2495022C2 (ru) * 2008-11-26 2013-10-10 Колгейт-Палмолив Компани Композиции и способы для смягчения тканей
GB0907886D0 (en) * 2009-05-07 2009-06-24 M I Drilling Fluids Uk Ltd Corrosion inhibitor
JP6530019B2 (ja) * 2017-08-08 2019-06-12 田中貴金属工業株式会社 金属インク
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ES2939182T3 (es) 2017-09-25 2023-04-19 Evonik Operations Gmbh Concentrados estables al almacenamiento que contienen polisiloxanos y su empleo, preferentemente en composiciones de mantenimiento textil
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Also Published As

Publication number Publication date
DE4334365A1 (de) 1995-04-13
JPH09503513A (ja) 1997-04-08
US5886201A (en) 1999-03-23
WO1995010500A1 (fr) 1995-04-20

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