EP0674699B1 - Agents d'avivage actifs anioniques sans azote - Google Patents

Agents d'avivage actifs anioniques sans azote Download PDF

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Publication number
EP0674699B1
EP0674699B1 EP94902731A EP94902731A EP0674699B1 EP 0674699 B1 EP0674699 B1 EP 0674699B1 EP 94902731 A EP94902731 A EP 94902731A EP 94902731 A EP94902731 A EP 94902731A EP 0674699 B1 EP0674699 B1 EP 0674699B1
Authority
EP
European Patent Office
Prior art keywords
fatty acid
acid partial
partial glycerides
formula
nitrogen
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 - Lifetime
Application number
EP94902731A
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German (de)
English (en)
Other versions
EP0674699A1 (fr
Inventor
Ansgar Behler
Uwe Ploog
Günther Uphues
Bernd Wahle
Peter Waltenberger
Yvonne Jansen
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Henkel AG and Co KGaA
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Henkel AG and Co KGaA
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Publication date
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Publication of EP0674699A1 publication Critical patent/EP0674699A1/fr
Application granted granted Critical
Publication of EP0674699B1 publication Critical patent/EP0674699B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
    • D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
    • D21H21/22—Agents rendering paper porous, absorbent or bulky
    • D21H21/24—Surfactants
    • 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
    • C11D1/28—Sulfonation products derived from fatty acids or their derivatives, e.g. esters, amides
    • 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
    • C14—SKINS; HIDES; PELTS; LEATHER
    • C14C—CHEMICAL TREATMENT OF HIDES, SKINS OR LEATHER, e.g. TANNING, IMPREGNATING, FINISHING; APPARATUS THEREFOR; COMPOSITIONS FOR TANNING
    • C14C9/00—Impregnating leather for preserving, waterproofing, making resistant to heat or similar purposes
    • C14C9/02—Impregnating leather for preserving, waterproofing, making resistant to heat or similar purposes using fatty or oily materials, e.g. fat liquoring
    • 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
    • D06M13/10—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 oxygen
    • D06M13/224—Esters of carboxylic acids; Esters of carbonic acid
    • D06M13/2243—Mono-, di-, or triglycerides
    • 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
    • D06M7/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made of other substances with subsequent freeing of the treated goods from the treating medium, e.g. swelling, e.g. polyolefins
    • 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
    • D06M2200/40—Reduced friction resistance, lubricant properties; Sizing compositions

Definitions

  • the invention relates to the use of sulfated fatty acid partial glycerides as nitrogen-free anionic softeners.
  • Cationic or pseudo-cationic compounds are predominantly used to soften textiles, yarns and fibers, but also in the field of leather finishing and paper production.
  • Important representatives of this group are e.g. B. distearyldimethylammonium chloride (DSDMAC), quaternized difatty acid alkanolamine ester salts or reaction products of fatty acids with polyamines, e.g. B. aminoethylethanolamine.
  • DMDMAC distearyldimethylammonium chloride
  • quaternized difatty acid alkanolamine ester salts or reaction products of fatty acids with polyamines e.g. B. aminoethylethanolamine.
  • these compounds have excellent reviving properties, the biodegradability and the sensitization potential of a number of products are not completely satisfactory [cf. Soap-oil-fat waxes, 117, 287 and 690 (1991) ].
  • anionic compounds are actually known from the extensive state of the art in the field of softening and fabric softening agents, which also have softening properties and are readily biodegradable.
  • performance of the anionic softening agents known to date is so low that, despite ecotoxicological advantages, they have so far not found their way into commercial products.
  • the object of the invention was to develop new nitrogen-free anionic softening agents which are free from the disadvantages described.
  • the invention relates to the use of sulfated fatty acid partial glycerides of the formula (I) , in the R 1 , R 2 and R 3 independently of one another represent at least one aliphatic, linear or branched acyl radical having 6 to 22 carbon atoms, at least one sulfate group and optionally a hydroxyl group and m, n and p are 0 or numbers from 1 to 10, as nitrogen-free aninoactive conditioning agents.
  • sulfated fatty acid partial glycerides have very good softening properties, are readily biodegradable and thus meet all the requirements for being successfully used in softeners and fabric softeners.
  • the sulfated fatty acid partial glycerides are known substances that can be obtained with the help of relevant methods of preparative organic chemistry.
  • a preferred method is, for example, to sulfate technical partial glyceride mixtures with a high diglyceride content in continuously operated falling film reactors with gaseous sulfur trioxide and then to enter and neutralize the products in sodium hydroxide solution [cf. DE-A1 40 38 477, Henkel].
  • fatty acid partial glyceride is then to be understood as a technical mixture of mono-, di- and triglycerides which can still contain fractions of free glycerol. Mixtures which have a content of 25 to 50, preferably 35 to 40% by weight of diglyceride, based on the mixture, are preferably used.
  • the resulting sulfated fatty acid partial glycerides are also technical mixtures which, in addition to sulfated diglycerides, may contain, above all, monoglyceride sulfates and unsulfated components.
  • the proportion of the sulfated 1,2- or 1,3-diglycerides is preferably 30 to 60% by weight, based on the anionic surfactant content.
  • the sulfated fatty acid partial glycerides can also contain ethylene oxide groups in the molecule. Such compounds are also known in principle and can be produced, for example, by ethoxylation of fatty acid partial esters and subsequent sulfation.
  • the sum of the indices m, n and p represents the degree of ethoxylation, where each individual index can stand for 0 or numbers from 1 to 10, preferably 2 to 7. Accordingly, the preferred sulfated fatty acid glycerides containing ethylene oxide are obtained by sulfating adducts of an average of 6 to 21 and in particular 10 to 15 moles of ethylene oxide with fatty acid partial glycerides.
  • m, n and p do not necessarily have to represent the same values, since in the case of the ethoxylation of fatty acid partial esters there is a competition between the addition of ethylene oxide to free hydroxyl groups and the insertion into the ester bond.
  • the resulting homolog distribution can also be conventional or restricted, depending on the catalyst used.
  • Sulfated fatty acid partial glycerides of the formula (I) are preferably used, in which R 1 and R 3 are acyl radicals and R 2 is a sulfate group or in R 1 and R 2 are acyl radicals and R 3 is a sulfate group and m, n and p are 0.
  • the term “sulfate group” is to be understood as an —SO 3 X group in which X represents ammonium, alkylammonium or an alkali and / or alkaline earth metal, preferably sodium.
  • sulfated fatty acid partial glycerides of the formula (I) are preferably used in which R 1 , R 2 and R 3 independently of one another represent at least one acyl radical having 16 to 18 carbon atoms and m, n and p are 0.
  • the use of nitrogen-free anionic softening agents which contain sulfated diglycerides based on C 16/18 tallow fatty acid has proven to be particularly advantageous with regard to their softening properties.
  • the tallow fatty acid component can be saturated, partially saturated or predominantly unsaturated.
  • the nitrogen-free anionic softening agents according to the invention can usually contain the sulfated fatty acid partial glycerides of the formula (I) in amounts of 1 to 100, preferably 50 to 95% by weight, based on the solids content of the agents.
  • the agents themselves are generally sold as aqueous concentrates with a solids content of 30 to 70% by weight or in the form of flaked goods.
  • they can contain other customary auxiliaries and additives in the customary amounts, for. B. dispersants, perfumes and viscosity regulators.
  • the sulfated fatty acid partial glycerides used as softening agents according to the invention are ecotoxicologically very well tolerated and give textile fabrics, but also leather and paper a pleasant soft feel. They can therefore be used, for example, for the continuous or discontinuous finishing of textiles.
  • Another object of the invention therefore relates to their use for the production of softeners and fabric softeners, in which they can be present in amounts of 1 to 70, preferably 10 to 50 and in particular 15 to 30% by weight, based on the detergent.
  • the agents according to the invention can contain other conventional additives, such as e.g. Contain surfactants, emulsifiers, synthetic resins, catalysts and optical brighteners.
  • the sulfur trioxide was driven off by heating from an appropriate amount of 65% by weight oleum, diluted to a concentration of 5% by volume with nitrogen and brought into contact with the diglyceride film via a nozzle.
  • the anionic surfactant content (WAS) and the unsulfonated content (US) were determined according to the DGF standard methods, Stuttgart 1950-1984, H-III-10 and G-II-6b.
  • agent (A) The softening effect of agent (A) according to the invention was determined in the foulard method by forced application to a cotton fabric.
  • the softness performance was determined by sampling from a panel of test persons (6 persons).
  • a commercial finishing agent based on a fatty acid polyamine condensate (B) was used for comparison.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Textile Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Des glycérides partiels d'acides gras sulphatés ont la formule (I), dans laquelle R?1, R2 et R3¿ désignent indépendamment les uns des autres au moins un résidu acyle aliphatique linéaire ou ramifié ayant 6 à 22 atomes de carbone, au moins un groupe sulphate et le cas échéant un groupe hydroxyle, m, n et p étant égaux à 0 ou des nombres entre 1 et 10. Ces glycérides sont utiles pour produire des agents avivants et adoucissants de rinçage du linge.

Claims (6)

  1. Utilisation de glycérides partiels d'acides gras sulfatés de formule (I),
    Figure imgb0003
     où R1, R2 et R3 représentent indépendamment l'un de l'autre au moins un radical acyle aliphatique, linéaire ou ramifié de 6 à 22 atomes de carbone, au moins un groupe sulfate et le cas échéant un groupe hydroxyle et m, n et p représentent 0 ou les nombres 1 à 10, sont sous forme de produits d'avivage anioniques sans azote.
  2. Utilisation selon la revendication 1,
    caractérisée en ce qu'
    on utilise des glycérides partiels d'acides gras sulfatés de formule (I), où R1 et R3 sont des radicaux acyles, R2 est un groupe sulfate et m, n et p représentent O.
  3. Utilisation selon les revendications 1 et 2,
    caractérisée en ce qu'
    on utilise les glycérides partiels d'acides gras sulfatés de formule (I), où R1 et R2 sont des radicaux acyles, R3 est un groupe sulfate et m, n et p représentent 0.
  4. Utilisation selon les revendications 1 à 3,
    caractérisée en ce qu'
    on utilise des glycérides partiels d'acides gras sulfatés de formule (I), où R1, R2 et R3 représentent indépendamment l'un de l'autre au moins un radical acyle de 16 à 18 atomes de carbone et m, n et p représentent 0.
  5. Utilisation selon les revendications 1 à 4,
    caractérisée en ce qu'
    on utilise des diglycérides sulfates à base d'acide gras de suif C16/18.
  6. Concentrés aqueux de produits d'avivage anioniques sans azote ayant une teneur en solide de 30-70 % en poids,
    caractérisé en ce qu'
    y sont présents comme produits d'avivage des glycérides partiels d'acides gras sulfatés de formule (I) selon la revendication 1 en une quantité de 1-100 % en poids, par rapport à la teneur en solide.
EP94902731A 1992-12-17 1993-12-09 Agents d'avivage actifs anioniques sans azote Expired - Lifetime EP0674699B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE4242689 1992-12-17
DE4242689A DE4242689A1 (de) 1992-12-17 1992-12-17 Stickstofffreie anionaktive Avivagemittel
PCT/EP1993/003469 WO1994013768A1 (fr) 1992-12-17 1993-12-09 Agents d'avivage actifs anioniques sans azote

Publications (2)

Publication Number Publication Date
EP0674699A1 EP0674699A1 (fr) 1995-10-04
EP0674699B1 true EP0674699B1 (fr) 1997-11-05

Family

ID=6475589

Family Applications (1)

Application Number Title Priority Date Filing Date
EP94902731A Expired - Lifetime EP0674699B1 (fr) 1992-12-17 1993-12-09 Agents d'avivage actifs anioniques sans azote

Country Status (6)

Country Link
US (1) US5567340A (fr)
EP (1) EP0674699B1 (fr)
JP (1) JPH08504484A (fr)
CN (1) CN1093765A (fr)
DE (2) DE4242689A1 (fr)
WO (1) WO1994013768A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19651447C1 (de) * 1996-12-11 1997-10-02 Henkel Kgaa Mittel für die Avivage von Textil- und Keratinfasern und Verwendung von Hydroxycarbonsäureestern zur Herstellung von Avivagemitteln
DE19708133C1 (de) * 1997-02-28 1997-12-11 Henkel Kgaa Mittel für die Avivage von Textil- und Keratinfasern sowie die Verwendung von Hydroxycarbonsäureestern zur Herstellung von Avivagemitteln
CN110512425B (zh) * 2019-09-29 2022-04-19 罗莱生活科技股份有限公司 一种功能性纺织品及其制备方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3936001A1 (de) * 1989-10-28 1991-05-02 Henkel Kgaa Verfahren zur sulfierung ungesaettigter fettsaeureglycerinester
US5117032A (en) * 1990-06-06 1992-05-26 Henkel Kommanditgesellschaft Auf Aktien Process for making glycerol ether sulfates
DE4038477A1 (de) * 1990-12-03 1992-06-04 Henkel Kgaa Verfahren zur kontinuierlichen herstellung von partialglyceridsulfaten
DE4038478A1 (de) * 1990-12-03 1992-06-04 Henkel Kgaa Verfahren zur herstellung von partialglyceridsulfaten

Also Published As

Publication number Publication date
US5567340A (en) 1996-10-22
DE59307653D1 (de) 1997-12-11
JPH08504484A (ja) 1996-05-14
CN1093765A (zh) 1994-10-19
WO1994013768A1 (fr) 1994-06-23
DE4242689A1 (de) 1994-06-23
EP0674699A1 (fr) 1995-10-04

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