WO1994015011A1 - Adjuvants pour fibres - Google Patents

Adjuvants pour fibres

Info

Publication number
WO1994015011A1
WO1994015011A1 PCT/EP1993/003518 EP9303518W WO9415011A1 WO 1994015011 A1 WO1994015011 A1 WO 1994015011A1 EP 9303518 W EP9303518 W EP 9303518W WO 9415011 A1 WO9415011 A1 WO 9415011A1
Authority
WO
WIPO (PCT)
Prior art keywords
carbon atoms
methyl
hydrogen
fatty acid
acyl radical
Prior art date
Application number
PCT/EP1993/003518
Other languages
German (de)
English (en)
Inventor
Joaquim Bigorra Llosas
Maria Dolors LÓPEZ GÓMEZ
Antoni Soler Codina
Original Assignee
Henkel Kommanditgesellschaft Auf Aktien
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 Kommanditgesellschaft Auf Aktien filed Critical Henkel Kommanditgesellschaft Auf Aktien
Priority to EP94903762A priority Critical patent/EP0675979A1/fr
Publication of WO1994015011A1 publication Critical patent/WO1994015011A1/fr

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
    • D06M13/46—Compounds containing quaternary nitrogen atoms
    • D06M13/463—Compounds containing quaternary nitrogen atoms derived from monoamines
    • 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
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/16—Anti-static materials
    • 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
    • D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
    • D06M2101/16—Synthetic fibres, other than mineral fibres
    • 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
    • D06M2200/40—Reduced friction resistance, lubricant properties; Sizing compositions

Definitions

  • the invention relates to auxiliaries for synthetic fibers which contain quaternized fatty acid triethanolamine ester salts and to the use of these salts for the preparation of the agents mentioned.
  • spin finishes In addition to the smoothness and the thread closure, the fiber manufacturers generally place further requirements on spin finishes, of which the reduction in friction, the softening of the fiber filaments and the compatibility with Dyes are the main ones. In addition to the requirements mentioned, spin finishes must be temperature-resistant and non-corrosive, easy to remove from the fiber and physiologically harmless. Cationic surfactants, in particular of the quaternized fatty amine type, are usually used for this purpose. However, these show the disadvantage of a biodegradability which is not satisfactory in all cases.
  • the object of the invention was to provide new auxiliaries for the production of synthetic fibers which have improved biodegradability.
  • the invention relates to fiber auxiliaries which contain quaternized fatty acid triethanolamine ester salts of the formula (I) as active component,
  • R --- CO is an acyl radical having 6 to 22 carbon atoms
  • R and R 2 independently of one another are hydrogen or R --- CO
  • R 1 is an alkyl radical having 1 to 10 carbon atoms
  • x, y and z are 1 or numbers from 2 to 30
  • X is a halide or alkyl sulfate.
  • the salts according to the invention reduce the electrostatic charge on synthetic fibers. They also have fiber-enhancing properties, are stable at high temperatures, readily biodegradable and physiologically harmless.
  • the quaternized fatty acid triethanolamine ester salts are known substances which can be obtained by the relevant methods of preparative organic chemistry.
  • a process for their preparation as described in international patent application WO 91/1295 (Henkel), consists in esterifying fatty acids with triethanolamine in the presence of hypophosphorous acid and the technical fatty acid ester mixture, the mono-, di- and tri - contains ester, then quaternize with methyl chloride or diethyl sulfate.
  • polyglycol ether group-containing, ie ethoxylated, quaternized fatty acid triethanolamine ester salts are the subject of a previously unpublished application by the applicant.
  • ethoxylated triethanolamine which in turn is esterified and quaternized in a known manner. In this case, you usually add an average of 2 to 30, preferably 2 to 10 moles of ethylene oxide of triethanolamine in the esterification.
  • quaternized fatty acid triethanolamine ester salts are used for the preparation of the antistatic agents, fatty acid and triethanolamine or triethanolamine ethoxylate in a molar ratio of 1.2: 1 to 2.1: 1, preferably 1.64: 1 to 1.92: 1 have been used.
  • Fiber auxiliaries with particularly advantageous technical properties are obtained if quaternized fatty acid triethanola ester salts of the formula (I) are used in which
  • R ⁇ O is an acyl radical having 16 to 18 carbon atoms
  • R2 and R3 is hydrogen
  • R 4 is methyl
  • x, y and z are each 1
  • X is chloride or methyl sulfate
  • R - CO is an acyl radical with 16 to 18 carbon atoms
  • R2 and R3 are hydrogen
  • R 4 is methyl
  • x, y and z are numbers from 2 to 30
  • X is chloride or methyl sulfate
  • Quaternized fatty acid triethanolamine ester salts reduce the electrostatic charge on fibers and reduce the friction between the filaments. They have revitalizing properties, are temperature-stable and easily biodegradable.
  • Another object of the invention therefore relates to the use of the quaternized fatty acid triethanolamine ester salts for the production of spin finishes and finishing agents for synthetic fibers, in particular acrylic and polyester fibers.
  • the spin finishes or finishing agents are applied in the form of aqueous dispersions to the synthetic fibers immediately after they emerge from the spinneret.
  • the agents which have a temperature between 18 and 60 ° C, z. B. applied by application rollers or dosing pumps via suitable applicators.
  • the agents are preferably used in the form of their aqueous dispersions, which have a solids content of 3 to 40, preferably 5 to 30,% by weight and, in addition to the quaternized fatty acid triethanolamine ester salts, also other customary ingredients, such as, for example, synthetic ester oils , Sorbitan esters, silicones, polyethers, phosphoric acid esters, fatty acid alkanolamines, ethoxylated fatty acids and block polymers of ethylene and propylene oxide ("Pluronic types”) and the like.
  • the proportion of quaternized fatty acid triethanolamine ester salts in the compositions can be 1 to 100, preferably 30 to 70% by weight, based on the solids content.
  • the application amount of the spin finishes or finishing agents in the form of their aqueous dispersions is in the range customary for the fiber industry between 0.1 and 30, preferably 1 to 20% by weight, based on the weight of the fibers.
  • Base tallow acid unhardened
  • Base coconut fatty acid unhardened
  • Base tallow acid hardened
  • Base tallow acid 50% hardened
  • Dye bleeding (dye: cationic black) visual assessment:

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (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 désigne un reste acyle ayant 6 à 22 atomes de carbone, R¿2? et R3 désigent indépendamment l'un de l'autre hydrogène ou R?1CO, R4¿ désigne un reste alkyle ayant 1 à 10 atomes de carbone, x, y et z valent 1 ou des nombres compris entre 2 et 30 et X représente un haloïde ou un sulfate d'alkyle. Ces sels quaternaires d'esters de triéthanolamine d'acide gras sont appropriés pour être utilisés dans la fabrication d'adjuvants pour fibres synthétiques.
PCT/EP1993/003518 1992-12-22 1993-12-13 Adjuvants pour fibres WO1994015011A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP94903762A EP0675979A1 (fr) 1992-12-22 1993-12-13 Adjuvants pour fibres

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19924243550 DE4243550C1 (de) 1992-12-22 1992-12-22 Faserhilfsmittel und deren Verwendung
DEP4243550.1 1992-12-22

Publications (1)

Publication Number Publication Date
WO1994015011A1 true WO1994015011A1 (fr) 1994-07-07

Family

ID=6476170

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1993/003518 WO1994015011A1 (fr) 1992-12-22 1993-12-13 Adjuvants pour fibres

Country Status (3)

Country Link
EP (1) EP0675979A1 (fr)
DE (1) DE4243550C1 (fr)
WO (1) WO1994015011A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000001763A1 (fr) * 1998-07-03 2000-01-13 Cognis Deutschland Gmbh Utilisation de composes quaternaires d'ester comme antistatiques
WO2000044824A1 (fr) * 1999-01-30 2000-08-03 Cognis Deutschland Gmbh Utilisation d'esters d'alcanolamine d'acide gras
WO2002036873A2 (fr) * 2000-11-01 2002-05-10 Cognis Iberia S.L. Agents servant a traiter des textiles

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19714044C1 (de) * 1997-04-05 1998-04-16 Henkel Kgaa Hydrophile Avivagemittel sowie Verwendung von Mischungen, enthaltend Esterquats und Siliconverbindungen zur Herstellung derselben

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1485159A (fr) * 1965-07-01 1967-06-16 Henkel & Cie Gmbh Agents assouplissants pour textiles
CH496138A (de) * 1967-12-01 1970-09-15 Hoechst Ag Verfahren zur Veredlung von Textilien
DE1935499A1 (de) * 1969-07-12 1971-01-14 Basf Ag Avivagemittel
FR2314288A1 (fr) * 1975-06-09 1977-01-07 Henkel & Cie Gmbh Agents d'avivage cationiques ayant une solubilite amelioree a l'eau froide
EP0525271A1 (fr) * 1991-07-29 1993-02-03 Kao Corporation, S.A. Procédé pour la préparation de composés quaternaires
DE4135115A1 (de) * 1991-10-24 1993-04-29 Trigon Chemie Gmbh Kationaktive tenside
WO1993016157A1 (fr) * 1992-02-07 1993-08-19 Henkel Kommanditgeselschaft Auf Aktien Procede de fabrication de concentres aqueux, de faible viscosite, d'esters quaternises

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1485159A (fr) * 1965-07-01 1967-06-16 Henkel & Cie Gmbh Agents assouplissants pour textiles
CH496138A (de) * 1967-12-01 1970-09-15 Hoechst Ag Verfahren zur Veredlung von Textilien
DE1935499A1 (de) * 1969-07-12 1971-01-14 Basf Ag Avivagemittel
FR2314288A1 (fr) * 1975-06-09 1977-01-07 Henkel & Cie Gmbh Agents d'avivage cationiques ayant une solubilite amelioree a l'eau froide
EP0525271A1 (fr) * 1991-07-29 1993-02-03 Kao Corporation, S.A. Procédé pour la préparation de composés quaternaires
DE4135115A1 (de) * 1991-10-24 1993-04-29 Trigon Chemie Gmbh Kationaktive tenside
WO1993016157A1 (fr) * 1992-02-07 1993-08-19 Henkel Kommanditgeselschaft Auf Aktien Procede de fabrication de concentres aqueux, de faible viscosite, d'esters quaternises

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000001763A1 (fr) * 1998-07-03 2000-01-13 Cognis Deutschland Gmbh Utilisation de composes quaternaires d'ester comme antistatiques
WO2000044824A1 (fr) * 1999-01-30 2000-08-03 Cognis Deutschland Gmbh Utilisation d'esters d'alcanolamine d'acide gras
US6835765B1 (en) 1999-01-30 2004-12-28 Cognis Deutschland Gmbh & Co..Kg Use of fatty acid alkanolamine esters as antistatics
WO2002036873A2 (fr) * 2000-11-01 2002-05-10 Cognis Iberia S.L. Agents servant a traiter des textiles
WO2002036873A3 (fr) * 2000-11-01 2002-12-12 Cognis Iberia Sl Agents servant a traiter des textiles

Also Published As

Publication number Publication date
DE4243550C1 (de) 1994-06-01
EP0675979A1 (fr) 1995-10-11

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