EP1330569B1 - Textilbehandlungsmittel - Google Patents

Textilbehandlungsmittel Download PDF

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Publication number
EP1330569B1
EP1330569B1 EP01992810A EP01992810A EP1330569B1 EP 1330569 B1 EP1330569 B1 EP 1330569B1 EP 01992810 A EP01992810 A EP 01992810A EP 01992810 A EP01992810 A EP 01992810A EP 1330569 B1 EP1330569 B1 EP 1330569B1
Authority
EP
European Patent Office
Prior art keywords
carbon atoms
alkyl
preparations
esterquats
contain
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
EP01992810A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP1330569A2 (de
Inventor
Marta Domingo
Joaquim Dr. Bigorra Llosas
Nuria Dr. Bonastre Gilabert
Rafael Dr. 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.)
Cognis IP Management GmbH
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Cognis IP Management GmbH
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 Cognis IP Management GmbH filed Critical Cognis IP Management GmbH
Publication of EP1330569A2 publication Critical patent/EP1330569A2/de
Application granted granted Critical
Publication of EP1330569B1 publication Critical patent/EP1330569B1/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/227Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of hydrocarbons, or reaction products thereof, e.g. afterhalogenated or sulfochlorinated
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38Cationic compounds
    • C11D1/62Quaternary ammonium compounds
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005Other compounding ingredients characterised by their effect
    • C11D3/001Softening compositions
    • C11D3/0015Softening compositions liquid
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/18Hydrocarbons
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/02Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with hydrocarbons
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322Treating 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
    • D06M13/46Compounds containing quaternary nitrogen atoms
    • D06M13/463Compounds containing quaternary nitrogen atoms derived from monoamines
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322Treating 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
    • D06M13/46Compounds containing quaternary nitrogen atoms
    • D06M13/467Compounds containing quaternary nitrogen atoms derived from polyamines
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M7/00Treating 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
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00Functionality of the treatment composition and/or properties imparted to the textile material
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/20Treatment influencing the crease behaviour, the wrinkle resistance, the crease recovery or the ironing ease
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/40Reduced friction resistance, lubricant properties; Sizing compositions
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/50Modified hand or grip properties; Softening compositions

Definitions

  • the invention is in the field of textile treatment agents and relates to novel preparations for finishing textiles consisting of combinations of cationic surfactants and waxes and their use.
  • Esterquats because of their property of giving textiles and fibers a pleasant softness, are also used as softening agents. In this case, the ability of the cationic surfactants to be applied to the fibers and, among other things, to reduce the static charge, ie to provide an antistatic finish.
  • esterquats with polyolefin waxes, as described in European Patent EP 0784666 B1 (Cognis), the softness can even be improved, but in particular the friction is reduced and the ironing of the textiles treated in this way is significantly facilitated.
  • Corresponding products are already commercially available, for example, under the name "Vernell Easy". Since the performance properties of the products are not always satisfactory, the object of the present invention was to provide new textile treatment agents which are more effective in antistatic finish and friction reduction than the prior art products or with the same performance is achieved at a reduced rate.
  • the new textile treatment agents are significantly superior in terms of antistatic finish, reduction of friction and thus improved ironability compared to known mixtures of esterquats and polyolefin waxes.
  • esters is generally understood to mean quaternized fatty acid triethanolamine ester salts. These are known substances that can be obtained by the relevant methods of preparative organic chemistry. In this connection, reference is made to International Patent Application WO 91/01295 (Henkel), according to which triethanolamine is partially esterified with fatty acids in the presence of hypophosphorous acid, air is passed through and then quaternized with dimethyl sulfate or ethylene oxide.
  • German Patent DE 4308794 C1 moreover discloses a process for preparing solid ester quats , in which the quaternization of triethanolamine esters is carried out in the presence of suitable dispersants, preferably fatty alcohols.
  • the quaternized fatty acid triethanolamine ester salts preferably follow the formula (I) in the R 1 CO for an acyl radical having 6 to 22 carbon atoms, R 2 and R 3 are independently hydrogen or R 1 CO, R 4 is an alkyl radical having 1 to 4 carbon atoms or a (CH 2 CH 2 O) q H Group, m, n and p in total are 0 or numbers from 1 to 12, q is numbers from 1 to 12 and X is halide, alkyl sulfate or alkyl phosphate.
  • esterquats which can be used in the context of the invention are products based on caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, isostearic acid, stearic acid, oleic acid, elaidic acid, Arachic acid, behenic acid and erucic acid and their technical mixtures, as obtained for example in the pressure splitting of natural fats and oils.
  • the fatty acids and the triethanolamine in a molar ratio of 1.1: 1 to 3: 1 can be used.
  • an employment ratio of 1.2: 1 to 2.2: 1, preferably 1.5: 1 to 1.9: 1 has proven to be particularly advantageous.
  • the preferred esterquats are technical mixtures of mono-, di- and triesters with an average degree of esterification of 1.5 to 1.9 and are derived from technical C 16/18 tallow or palm oil fatty acid (iodine value 0 to 40).
  • quaternized fatty acid triethanolamine ester salts of the formula (I) have proven to be particularly advantageous in which R 1 CO is an acyl radical having 16 to 18 carbon atoms, R 2 is R 1 CO, R 3 is hydrogen, R 4 is a methyl group, m , n and p are 0 and X is methylsulfate.
  • R 1 CO is an acyl radical having 16 to 18 carbon atoms
  • R 2 is R 1 CO
  • R 3 is hydrogen
  • R 4 is a methyl group
  • m , n and p are 0
  • X is methylsulfate.
  • Corresponding products are commercially available under the brand Dehyquart® AU (Cognis Deutschland GmbH).
  • suitable esterquats are, in addition, quaternized ester salts of fatty acids with diethanolalkylamines of the formula (II) , in the R 1 CO for an acyl radical having 6 to 22 carbon atoms, R 2 is hydrogen or R 1 CO, R 4 and R 5 are independently alkyl radicals having 1 to 4 carbon atoms, m and n in total for 0 or numbers from 1 to 12 and X is halide, alkyl sulfate or alkyl phosphate.
  • R 1 CO for an acyl radical having 6 to 22 carbon atoms
  • R 2 is hydrogen or R 1 CO
  • R 4 , R 6 and R 7 are independently alkyl radicals having 1 to 4 carbon atoms, m and n in total for 0 or numbers from 1 to 12 and
  • X is halide, alkyl sulfate or alkyl phosphate.
  • esterquats are substances in which the ester is replaced by an amide bond and which preferably follow the formula (IV) based on diethylenetriamine, in which R 1 CO is an acyl radical having 6 to 22 carbon atoms, R 2 is hydrogen or R 1 CO, R 6 and R 7 are independently alkyl radicals having 1 to 4 carbon atoms and X is halide, alkyl sulfate or alkyl phosphate.
  • R 1 CO is an acyl radical having 6 to 22 carbon atoms
  • R 2 is hydrogen or R 1 CO
  • R 6 and R 7 are independently alkyl radicals having 1 to 4 carbon atoms
  • X is halide, alkyl sulfate or alkyl phosphate.
  • Amidesterquats are available for example under the brand Incroquat® (Croda) in the market.
  • esterquats are also substances which are obtainable on the basis of ethoxylated castor oil or its hardening products and which preferably follow the formula (V) , in the R 8 CO for a saturated and / or unsaturated ethoxylated hydroxyacyl radical having 16 to 22, preferably 18 carbon atoms and 1 to 50 oxyethylene units,
  • A is a linear or branched alkylene radical having 1 to 6 carbon atoms
  • R 9 , R 10 and R 11 is independently hydrogen or an alkyl group of 1 to 4 carbon atoms
  • R 12 is an alkyl radical of 1 to 4 carbon atoms or a benzyl radical
  • X is halogen, alkyl sulfate or alkyl phosphate.
  • Both the fatty acids and the corresponding triglycerides can be used to prepare the esterquats of the formulas (I) to (V).
  • Such a method which is to be mentioned as representative of the corresponding prior art, is proposed in the European patent EP 0750606 B1 (Cognis). It is also possible to carry out the condensation of the alkanolamines with the fatty acids in the presence of defined amounts of dicarboxylic acids such as oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid, glutaric acid, adipic acid, sorbic acid, pimelic acid, azelaic acid, sebacic acid and / or dodecanedioic acid.
  • dicarboxylic acids such as oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid, glutaric acid, adipic acid, sorbic acid, pimelic acid, azelaic acid, sebacic acid and / or
  • esterquats in the form of 50 to 90 wt .-% iger alcoholic solutions in the trade, which can be easily diluted with water if necessary.
  • Paraffin waxes produce commercial substances which are obtained, for example, during the workup of petroleum distillates and are available, for example, from BASF. Typically, these waxes have molecular weights in the range of 100 to 1000 daltons. As a rule, they are commercially available in the form of aqueous dispersions which have solids contents in the range from 25 to 50% by weight.
  • the final formulations may contain components (a) and (b) in a weight ratio of from 90:10 to 10:90, preferably from 75:25 to 25:75 and most preferably from 60:40 to 40:60.
  • the total content of components (a) and (b) may contain 5 to 80, preferably 10 to 30 or 50 to 75,% by weight, depending on whether concentrates or application dilutions are used.
  • the agents according to the invention are far superior to those of the prior art based on polyolefin waxes.
  • the friction resistance is halved and the static charge reduced to one third.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Textile Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
EP01992810A 2000-11-01 2001-10-23 Textilbehandlungsmittel Expired - Lifetime EP1330569B1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10054020 2000-11-01
DE2000154020 DE10054020B4 (de) 2000-11-01 2000-11-01 Verwendung von Mischungen als Textilbehandlungsmittel
PCT/EP2001/012224 WO2002036873A2 (de) 2000-11-01 2001-10-23 Textilbehandlungsmittel

Publications (2)

Publication Number Publication Date
EP1330569A2 EP1330569A2 (de) 2003-07-30
EP1330569B1 true EP1330569B1 (de) 2006-04-26

Family

ID=7661713

Family Applications (1)

Application Number Title Priority Date Filing Date
EP01992810A Expired - Lifetime EP1330569B1 (de) 2000-11-01 2001-10-23 Textilbehandlungsmittel

Country Status (4)

Country Link
EP (1) EP1330569B1 (es)
DE (2) DE10054020B4 (es)
ES (1) ES2262701T3 (es)
WO (1) WO2002036873A2 (es)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10227872A1 (de) 2002-06-22 2004-01-08 Ecolab Gmbh & Co. Ohg Wässriges Konzentrat zur Desinfektion von Oberflächen
US20110243874A1 (en) 2010-04-01 2011-10-06 Rajan Keshav Panandiker Care polymers
EP2841639A1 (en) 2012-04-24 2015-03-04 3M Innovative Properties Company Surfactant-containing fluorochemical compositions, articles, and methods

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB602109A (en) * 1944-06-14 1948-05-20 E F Houghton And Co Wax emulsions and method of preparing the same
JP2669559B2 (ja) * 1989-09-07 1997-10-29 花王株式会社 アクリル繊維用紡績油剤
DE4243550C1 (de) * 1992-12-22 1994-06-01 Henkel Kgaa Faserhilfsmittel und deren Verwendung
EP0680314B1 (de) * 1993-01-23 1997-05-07 Henkel Kommanditgesellschaft auf Aktien Detergensgemische mit verbesserten avivageeigenschaften
DE4435386A1 (de) * 1994-10-04 1996-04-11 Henkel Kgaa Wäßrige Weichspülerdispersionen
DE19829788A1 (de) * 1998-07-03 2000-01-05 Henkel Kgaa Verwendung von Esterquats als Antistatika
DE19846538C2 (de) * 1998-10-09 2003-08-14 Cognis Deutschland Gmbh Quartäre Ammoniumverbindungen

Also Published As

Publication number Publication date
EP1330569A2 (de) 2003-07-30
DE10054020A1 (de) 2002-05-16
DE50109641D1 (de) 2006-06-01
WO2002036873A3 (de) 2002-12-12
DE10054020B4 (de) 2007-04-26
ES2262701T3 (es) 2006-12-01
WO2002036873A2 (de) 2002-05-10

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