EP0011130A1 - Composés aminoéthers aliphatiques, procédé pour leur préparation et leur utilisation pour l'adoucissement de tissus - Google Patents

Composés aminoéthers aliphatiques, procédé pour leur préparation et leur utilisation pour l'adoucissement de tissus Download PDF

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Publication number
EP0011130A1
EP0011130A1 EP79103847A EP79103847A EP0011130A1 EP 0011130 A1 EP0011130 A1 EP 0011130A1 EP 79103847 A EP79103847 A EP 79103847A EP 79103847 A EP79103847 A EP 79103847A EP 0011130 A1 EP0011130 A1 EP 0011130A1
Authority
EP
European Patent Office
Prior art keywords
formula
compounds
carbon atoms
methyl
group
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.)
Ceased
Application number
EP79103847A
Other languages
German (de)
English (en)
Inventor
Horst Dr. Rutzen
Jochen Dr. Heidrich
Martin Dr. Bischoff
Udo Dr. Kloubert
Peter Waltenberger
Ingo Wegener
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
Priority claimed from DE19782844463 external-priority patent/DE2844463A1/de
Priority claimed from DE19782844451 external-priority patent/DE2844451A1/de
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP0011130A1 publication Critical patent/EP0011130A1/fr
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • D06M13/372—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 containing etherified or esterified hydroxy groups ; Polyethers of low molecular weight
    • 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
    • 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
    • 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
    • D06M2200/20—Treatment influencing the crease behaviour, the wrinkle resistance, the crease recovery or the ironing ease
    • 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
    • D06M2200/25—Resistance to light or sun, i.e. protection of the textile itself as well as UV shielding materials or treatment compositions therefor; Anti-yellowing treatments
    • 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
    • D06M2200/50—Modified hand or grip properties; Softening compositions

Definitions

  • finishing agents are applied which give the textiles softness and suppleness or redefine the character of the goods from a fashion point of view.
  • technical requirements such as antistatic, crease recovery, yellowing, surface smoothness, etc. play a role.
  • the most commonly used fabric softener in this class of compounds is ditallow alkyl or distearyl dimethyl ammonium chloride.
  • this textile softener has excellent softening properties as well as productivity, substantivity and applicability under all customary conditions, both in textile finishing and in textile care, they also have disadvantages.
  • the usual cationic softeners turn yellow, a property that cannot be accepted with white goods or pastel-colored articles.
  • Another disadvantage of cationic finishing agents is the fact that the textiles finished with them acquire a hydrophobic character. In particular with cellulose fibers, which are precisely because of their excellent absorbency in hygiene articles, e.g. If cotton, diapers, bandages, tampons or for terry and tricot goods are used, this water-repellent property is not desirable.
  • the present invention was therefore based on the object to provide new quaternary ammonium compounds which can be obtained in a simple manner from readily available cheap raw materials, the textiles treated therewith in a finishing process or in laundry care with good softening effect, maintain the absorbency and remain without residue in the process Have the laundry of the textiles removed.
  • Another task was to provide new tertiary amines as precursors from which the quaternary ammonium compounds can be produced by quaternization.
  • the invention therefore relates to new quaternary ammonium compounds of the formula I.
  • R 3 is an alkyl group or hydroxyalkyl group having 1 to 4 carbon atoms or a radical of the formula
  • R 4 is an alkyl group having 1 to 4 carbon atoms
  • X and Y are hydrogen or the methyl group, but X and Y in the same ethoxy group are not both methyl
  • m, n and p are integers between 1 and 20 and
  • a ⁇ is An anion is present, is easily accessible from a preparative point of view and at the same time has excellent laundry finishing properties.
  • a ⁇ means an anion split off from the quaternizing agent, e.g. B. a chloride or methyl sulfate anion.
  • the anion can also be another anion common in quaternary ammonium compounds, e.g. B. be the bromide or ethyl sulfate anion.
  • the compounds of the formula I can be prepared in a simple manner from inexpensive starting materials in high yield via the tertiary amine of the formula II, in which R 1 , R 2 , R 3 , X, Y, m and n have the abovementioned meaning.
  • the invention therefore also relates to the provision of the compounds of the formula II as valuable intermediates.
  • the invention therefore furthermore relates to a process for the preparation of the new quaternary ammonium compounds and the new tertiary amines of the formula II on which they are based
  • the internal epoxyalkanes are obtained, for example, by epoxidizing olefins or olefin mixtures which are prepared by catalytic dehydrogenation or by chlorination / dehydrogenation of linear paraffin hydrocarbons. Monoolefins with an internal double bond can also be prepared by isomerization of ⁇ -olefins.
  • Internal epoxyalkanes of a C 11/14 olefin fraction which were preferably used contained approx. 22% by weight of C 11 -, approx. 30% by weight of C 12 -, approx. 26% by weight of C 13 -, approx. 22% by weight. % C 14 epoxyalkane.
  • the measured integration ratio 2: 10: 4: 3: 6 also agrees with the theoretical integration ratio for this connection.
  • the items of laundry treated with these formulations had good grip and good absorbency.
  • the climbing height method checks the speed at which textile fabrics absorb water.
  • the values specified under warp and weft are in ; mm climbing height.
  • the fabric accordingly has no hydrophilic properties, while the handle roughly corresponds to the fabric equipped according to the invention.
  • a fabric made of diol loft is padded in the usual way with a liquor containing 3 g / l of a preparation of 14 parts of the compound prepared according to Example 2 and 6 parts of the fatty alcohol polyglycol ether mentioned in Example 5 and then dried at 110 ° C. for 2 minutes .
  • the result is a soft fabric with a surface electrical resistance of 2 x 1 0 0 8 ohms and a field decay half-life of 0, as measured under standard conditions.
  • a bleached and optically brightened shirt poplin made of polyester / cotton (50/50) is padded in the usual manner with a liquor containing 4 g / l of the compound prepared according to Example 2 and dried at 110 ° C. for 2 minutes. If this fabric is then exposed to a temperature of 120 ° C for two minutes, no yellowing occurs.
  • a fabric is treated with a condensation product of 1 mole of a C 16-18 fatty acid and 1 mole of a hydroxylpolyethylene polyamine, the fabric exhibits a marked yellowing with the same hydrophilicity.

Landscapes

  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Textile Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP79103847A 1978-10-12 1979-10-08 Composés aminoéthers aliphatiques, procédé pour leur préparation et leur utilisation pour l'adoucissement de tissus Ceased EP0011130A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE19782844463 DE2844463A1 (de) 1978-10-12 1978-10-12 Verfahren zur avivage von textilmaterial waehrend des veredlungsprozesses
DE2844451 1978-10-12
DE2844463 1978-10-12
DE19782844451 DE2844451A1 (de) 1978-10-12 1978-10-12 Neue quartaere ammoniumverbindungen, ein verfahren zu ihrer herstellung und ihre verwendung als textilweichmacher

Publications (1)

Publication Number Publication Date
EP0011130A1 true EP0011130A1 (fr) 1980-05-28

Family

ID=25776069

Family Applications (1)

Application Number Title Priority Date Filing Date
EP79103847A Ceased EP0011130A1 (fr) 1978-10-12 1979-10-08 Composés aminoéthers aliphatiques, procédé pour leur préparation et leur utilisation pour l'adoucissement de tissus

Country Status (6)

Country Link
US (1) US4281196A (fr)
EP (1) EP0011130A1 (fr)
BR (1) BR7906611A (fr)
DK (1) DK394779A (fr)
ES (1) ES484962A1 (fr)
TR (1) TR20618A (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0218247A2 (fr) * 1985-10-08 1987-04-15 Bayer Ag Composition de nettoyage
EP0354993A2 (fr) * 1988-07-18 1990-02-21 Henkel Kommanditgesellschaft auf Aktien Procédé pour la préparation de produits d'addition de l'oxyde d'éthylène et/ou de l'oxyde de propylène à des amines resp. amides
WO1993008157A1 (fr) * 1991-10-23 1993-04-29 Ppg Industries (France) S.A. Produits de reaction d'amine-diol et de substance polyfonctionnelle et leur application dans les compositions de peintures cationiques electrodeposables

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE443138B (sv) * 1979-12-10 1986-02-17 Berol Kemi Ab Ytaktiv kvarter ammoniumforening samt anvendning av denna vid behandling av textil- och cellulosamaterial
FR2489315A1 (fr) 1980-08-27 1982-03-05 Rhone Poulenc Ind Nouveaux aminoalcools polyoxaalkyles, leur procede de preparation et leur application comme agents de complexation de cations
DE3135014A1 (de) * 1981-09-04 1983-03-24 Hoechst Ag, 6000 Frankfurt Waescheweichspuelmittel
US4485048A (en) * 1982-08-09 1984-11-27 Akzona Incorporated Ethoxylated quaternary benzyl compounds
US4694104A (en) * 1982-08-09 1987-09-15 Gaf Corporation Phase transfer catalysts
US4827038A (en) * 1987-08-03 1989-05-02 Texaco Inc. Bis(diaminopolyalkoxy)-N-alkylamines by amination of hydroxyl-containing tertiary amines
JP3007391B2 (ja) * 1990-08-13 2000-02-07 花王株式会社 新規第４級アンモニウム化合物
US5282983A (en) * 1990-08-22 1994-02-01 Kao Corporation Fabric softener composition and ammonium salt
US5463094A (en) * 1994-05-23 1995-10-31 Hoechst Celanese Corporation Solvent free quaternization of tertiary amines with dimethylsulfate
CA2329335A1 (fr) * 1998-04-24 1999-11-04 The Procter & Gamble Company Procede de nettoyage de textile
CN117363432B (zh) * 2023-11-27 2024-06-04 广州兰洁宝日用品科技有限公司 一种柔软去污型洗衣组合物及制备方法和洗衣片

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2256234A1 (de) * 1971-11-19 1973-05-24 Mo Och Domsjoe Ab Kationische oberflaechenaktive verbindungen, verfahren zu ihrer herstellung und ihre verwendung fuer die behandlung von textilmaterialien
DE2332277A1 (de) * 1972-06-27 1974-01-10 Daicel Ltd Antistatikum
DE2651898A1 (de) * 1976-11-13 1978-05-18 Hoechst Ag Waescheweichspuelmittel
US4139477A (en) * 1978-03-16 1979-02-13 E. I. Du Pont De Nemours And Company Fabric conditioning compositions

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3141905A (en) * 1963-04-29 1964-07-21 Witco Chemical Corp Cation-active surface active quaternary ammonium compounds
US3445440A (en) * 1965-10-15 1969-05-20 American Cyanamid Co Hydroxyalkyl quaternary ammonium ethers as antistatic agents
US3454646A (en) * 1966-01-04 1969-07-08 Wyandotte Chemicals Corp Polyether amine oxide surfaceactive agents
US4009255A (en) * 1966-07-26 1977-02-22 Societe Anonyme Dite: L'oreal Hair treating compositions containing cationic surface active agents
US3972855A (en) * 1971-11-19 1976-08-03 Modokemi Aktiebolag Quaternary ammonium compounds and treatment of plastic and other materials therewith
US4093663A (en) * 1973-11-15 1978-06-06 The Dow Chemical Company Novel onium surfactants
DE2628157C2 (de) * 1976-06-23 1986-10-30 Hoechst Ag, 6230 Frankfurt Quartäre Ammoniumverbindungen, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Haarpflegemittel
US4074970A (en) * 1976-11-15 1978-02-21 Sybron Corporation Dyeing of synthetic fibers with cationic dyes in the presence of cationic assistants containing hydroxyl and cyclic moieties

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2256234A1 (de) * 1971-11-19 1973-05-24 Mo Och Domsjoe Ab Kationische oberflaechenaktive verbindungen, verfahren zu ihrer herstellung und ihre verwendung fuer die behandlung von textilmaterialien
DE2332277A1 (de) * 1972-06-27 1974-01-10 Daicel Ltd Antistatikum
DE2651898A1 (de) * 1976-11-13 1978-05-18 Hoechst Ag Waescheweichspuelmittel
US4139477A (en) * 1978-03-16 1979-02-13 E. I. Du Pont De Nemours And Company Fabric conditioning compositions

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0218247A2 (fr) * 1985-10-08 1987-04-15 Bayer Ag Composition de nettoyage
EP0218247A3 (fr) * 1985-10-08 1988-09-07 Bayer Ag Composition de nettoyage
EP0354993A2 (fr) * 1988-07-18 1990-02-21 Henkel Kommanditgesellschaft auf Aktien Procédé pour la préparation de produits d'addition de l'oxyde d'éthylène et/ou de l'oxyde de propylène à des amines resp. amides
EP0354993A3 (fr) * 1988-07-18 1991-08-21 Henkel Kommanditgesellschaft auf Aktien Procédé pour la préparation de produits d'addition de l'oxyde d'éthylène et/ou de l'oxyde de propylène à des amines resp. amides
WO1993008157A1 (fr) * 1991-10-23 1993-04-29 Ppg Industries (France) S.A. Produits de reaction d'amine-diol et de substance polyfonctionnelle et leur application dans les compositions de peintures cationiques electrodeposables
FR2682951A1 (fr) * 1991-10-23 1993-04-30 Ppg Ind France Sa Amine-diol, son obtention et son application dans les additifs pour peintures cationiques electrodeposables.

Also Published As

Publication number Publication date
TR20618A (tr) 1982-02-19
US4281196A (en) 1981-07-28
ES484962A1 (es) 1980-06-16
DK394779A (da) 1980-04-13
BR7906611A (pt) 1980-06-03

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PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

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RIN1 Information on inventor provided before grant (corrected)

Inventor name: RUTZEN, HORST, DR.

Inventor name: BISCHOFF, MARTIN, DR.

Inventor name: KLOUBERT, UDO, DR.

Inventor name: WEGENER, INGO

Inventor name: HEIDRICH, JOCHEN, DR.

Inventor name: WALTENBERGER, PETER