EP0069948B1 - Esters quaternaires d'un N-alkyl N,N',N'-polyoxyalkyl alpha oméga-diaminoalkylène avec des acides gras, leur procédé de préparation et leur utilisation - Google Patents

Esters quaternaires d'un N-alkyl N,N',N'-polyoxyalkyl alpha oméga-diaminoalkylène avec des acides gras, leur procédé de préparation et leur utilisation Download PDF

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Publication number
EP0069948B1
EP0069948B1 EP82105949A EP82105949A EP0069948B1 EP 0069948 B1 EP0069948 B1 EP 0069948B1 EP 82105949 A EP82105949 A EP 82105949A EP 82105949 A EP82105949 A EP 82105949A EP 0069948 B1 EP0069948 B1 EP 0069948B1
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EP
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Prior art keywords
alkyl
formula
quaternary
compounds
fatty
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EP82105949A
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German (de)
English (en)
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EP0069948A1 (fr
Inventor
Siegfried Dr. Billenstein
Herbert Dr. Hartung
Adolf Dr. May
Hans-Walter Dr. Bücking
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Hoechst AG
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Hoechst AG
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Classifications

    • 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

Definitions

  • EP-A-2 031 114 describes quaternary polyammonium salts as plasticizers for textile material, whereby compounds of the N-alkyl-tri (polyoxyalkylene) diaminoalkylene salt type are also included. From EP-A-22 562 it is known that quaternary ammonium salts can carry one or two polyoxyalkylene groups and that these polyoxyalkylene groups can be esterified by a fatty acid.
  • the compounds of formula (1) are obtained by using a compound of formula (2) in which R 1 , x, y, m, n and p have the meanings given in formula (1), with a fatty acid of the formula 3 wherein R 3 has the meaning given in formula (1), esterified and the reaction product obtained quaternized with an alkylating reagent with the addition of the radical R 2 .
  • the preparation of the compounds of formula (1) starts from the compounds of formula (2). They are obtained by known methods by oxalkylation of fatty alkyl alkylene diamines such as. B. tallow fat propylene diamine (Schönfeldt, Surface active Ethylene Oxide Adducts 1969 p. 97).
  • the esterification of these compounds is carried out according to known methods with a fatty acid in higher-boiling inert solvents such as toluene or xylene or preferably without solvent in the melt and covered with a protective gas.
  • the reflux temperature of the reaction mixture is expediently chosen as the reaction temperature and the water of reaction formed is removed azeotropically.
  • the water of reaction is distilled off directly from the reaction mixture.
  • the reaction temperatures here are 140 to 220 ° C, preferably 150 to 180 ° C.
  • an acid catalyst such as e.g. B. p-toluenesulfonic acid. The completeness of the reaction is checked by determining the acid number.
  • the molar ratio of fatty acid to the compound of the formula (2) is 1 to 3, preferably 1 to 1.9 mol, of fatty acid to 1 mol of the compound of the formula 2.
  • the mixture of fatty acid esters thus obtained is then dissolved in an alcohol or dispersed in water and reacted with an alkylating agent at temperatures below 100 ° C., preferably at 40 to 80 ° C., to give the quaternary products according to the invention.
  • This reaction can also be carried out without any solvent.
  • the alkylation of the reaction mixture is adjusted to a pH of 6 to 7 by adding alkali and this solution is used directly as a fabric softener, if appropriate after appropriate dilution with water to the desired concentration and confection.
  • Preferred diamines on which the starting compounds of formula (2) are based are the industrially available products tallow fat propylene diamine or stearyl propylene diamine. However, it is equally possible according to the invention to use other diamines with a more or less broad alkyl chain distribution. Such diamines are prepared in a known manner by adding acrylonitrile to primary fatty amines and then catalytically hydrogenating the propionitriles.
  • Fatty acids suitable for esterification are products on a natural or synthetic basis, such as. As palmitic acid, stearic acid, behenic acid or branched chain compounds from oxo synthesis, such as. B. isostearic acid or mixtures of those, such as z. B. incurred from natural cuts derived from coconut oil or tallow.
  • the alkylating agent used is preferably methyl chloride or dimethyl sulfate.
  • the compounds of the formula (1) according to the invention are suitable as fabric softeners and are in the form of aqueous dispersions with an active substance content of 1 to 15% by weight, usually 4 to 10% by weight, of the compounds of the formula (1) following the washing of the textile material placed in the last rinsing bath. The textile material is then dried.
  • These fabric softeners can also contain other substances and auxiliaries that are commonly used in fabric softeners. These include e.g. B. cationic or nonionic surface-active substances, electrolytes, acidifying agents, organic complexing agents, optical brighteners or solubilizers, and colorants and fragrances.
  • the products are used to additionally influence the handle of the goods or other properties of the textiles to be treated or to adjust the viscosity, to regulate the pH or to increase the cold stability of the solutions.
  • the compounds according to the invention give any textile materials, especially those made of natural or regenerated cellulose, wool, cellulose acetate, triacetate, polyamide, polyacrylonitrile, polyester, polypropylene, a pleasant and soft feel.
  • Use as a laundry treatment agent for terry towels and underwear is particularly advantageous.
  • coconut fatty acid, oleic acid or tallow fatty acid derivatives can be obtained in an analogous manner.
  • 177 g of distearic acid ester prepared according to 1. is mixed in a stirred flask with 180 g of isopropanol and heated to 40 to 50 ° C. At this temperature, 48 g of dimethyl sulfate are added dropwise within about 30 minutes. After 3 hours, 12 g of sodium methylate solution (35% in methanol) and 9 g of dimethyl sulfate are added and the mixture is stirred at about 50 ° C. for a further 2 hours. After adding a further 9 g of sodium methylate solution, which brought the pH to 6.6 and cooling to room temperature, the product can be used in fabric softener formulations.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (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)
  • Detergent Compositions (AREA)

Claims (4)

1. Esters d'acides gras de N-alkyl-N,N',N'-polyoxyalkyl-diamino-alpha,oméga alkylènes quaternaires, de formule (1):
Figure imgb0010
dans laquelle:
R1 représente un groupe alkyle en C8 a C30 ou alcényle en C8 a C30,
R2 représente un groupe alkyle en C1 a' C4,
R3 représente un groupe alkyle en C7 à C29 ou alcényle en C7 a C29,
x et y représentent de l'hydrogène ou un groupe méthyle, mais x et y ne représentent pas simultanément chacun un groupe méthyle,
a vaut 0, 1 ou 2,
n est un nombre valant 1 à 11,
m vaut 1 ou 2,
p est un nombre valant 1 à 5, et
A est un anion.
2. Composés de formule (1) selon la revendication 1, dans laquelle R1 représente un groupe alkyle en C16 à C18 ou alcényle en C16 à C18, R2 est un groupe méthyle, x et y sont chacun un atome d'hydrogène, n vaut 1, m vaut 1, p vaut 3 et A est un ion halogénure, méthosulfate ou méthophosphate.
3. Procédé de préparation de composés de formule (1) selon la revendication 1, caractérisé en ce qu'on estérifie un composé de formule (2):
Figure imgb0011
(dans laquelle R1, x, y, m, n et p ont les sens indiqués pour la formule (1)) avec un acide gras de formule (3):
Figure imgb0012
(dans laquelle R3 a le sens indiqué pour la formule (1)) et l'on soumet le produit de réaction obtenu à une quaternisation à l'aide d'un réactif d'alkylation qui introduit le radical R2.
4. Utilisation des composés de formule ( 1 ) selon la revendication 1 comme produits pour l'assouplissement du linge lors de son rinçage.
EP82105949A 1981-07-10 1982-07-03 Esters quaternaires d'un N-alkyl N,N',N'-polyoxyalkyl alpha oméga-diaminoalkylène avec des acides gras, leur procédé de préparation et leur utilisation Expired EP0069948B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3127239 1981-07-10
DE19813127239 DE3127239A1 (de) 1981-07-10 1981-07-10 Quartaere n-alkyl-n,n',n'-polyoxyalkyl-(alpha),(omega)-diaminoalkylenfettsaeureester, verfahren zu deren herstellung und deren verwendung

Publications (2)

Publication Number Publication Date
EP0069948A1 EP0069948A1 (fr) 1983-01-19
EP0069948B1 true EP0069948B1 (fr) 1985-01-02

Family

ID=6136568

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Application Number Title Priority Date Filing Date
EP82105949A Expired EP0069948B1 (fr) 1981-07-10 1982-07-03 Esters quaternaires d'un N-alkyl N,N',N'-polyoxyalkyl alpha oméga-diaminoalkylène avec des acides gras, leur procédé de préparation et leur utilisation

Country Status (8)

Country Link
US (1) US4515723A (fr)
EP (1) EP0069948B1 (fr)
JP (1) JPS5818341A (fr)
AU (1) AU548545B2 (fr)
BR (1) BR8203996A (fr)
CA (1) CA1195338A (fr)
DE (2) DE3127239A1 (fr)
ES (1) ES513706A0 (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2508902B1 (fr) * 1981-07-02 1985-09-06 Commissariat Energie Atomique Procede de preparation extemporanee d'un acide gras injectable, marque a l'iode radioactif et preparation de derives iodes utilisables pour la mise en oeuvre de ce procede
DE3325228A1 (de) * 1983-07-13 1985-01-24 Hoechst Ag, 6230 Frankfurt Veresterte, oxalkylierte quaternaere ammoniumverbindungen, verfahren zu deren herstellung und deren verwendung als faserpraeparationsmittel
ES2021900A6 (es) * 1989-07-17 1991-11-16 Pulcra Sa Procedimiento de obtencion de tensioactivos cationicos derivados de amonio cuaternario con funcion amino-ester.
EP0648835A1 (fr) * 1993-10-14 1995-04-19 The Procter & Gamble Company Utilisation de sels alcalins de polyammonium pour augmenter la densité cationique des adoussinants textiles
US5670472A (en) * 1994-04-19 1997-09-23 Witco Corporation Biodegradable ester diquaternary compounds and compositions containing them
US5463094A (en) * 1994-05-23 1995-10-31 Hoechst Celanese Corporation Solvent free quaternization of tertiary amines with dimethylsulfate
US5491240A (en) * 1994-09-29 1996-02-13 Witco Corporation Quaternary compound of a tertiary amine and methyl chloride
US6211139B1 (en) 1996-04-26 2001-04-03 Goldschmidt Chemical Corporation Polyester polyquaternary compounds, compositions containing them, and use thereof

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2596985A (en) * 1949-12-20 1952-05-20 Arkansas Company Inc Fatty acid polyglycol-aliphatic amine combinations useful as textile softeners and process for producing the same
US2884459A (en) * 1955-12-15 1959-04-28 Visco Products Co Diamine derivatives containing hydroxyalkyl groups
US2944030A (en) * 1957-05-31 1960-07-05 Wyandotte Chemicals Corp Binary emulsifiers
US3509049A (en) * 1965-11-01 1970-04-28 Geigy Chem Corp Fabric softening and brightening compositions
US3983061A (en) * 1971-02-16 1976-09-28 Ciba-Geigy Corporation Process for the permanent finishing of fiber materials
LU75088A1 (fr) * 1976-06-04 1978-01-18
DE2631114C3 (de) * 1975-07-14 1981-11-26 The Procter & Gamble Co., 45202 Cincinnati, Ohio Weichmachungsmittel für Gewebe
DE2539310A1 (de) * 1975-09-04 1977-03-17 Hoechst Ag Textilweichmacher
FR2407260A1 (fr) * 1977-10-31 1979-05-25 Unilever Nv Compositions tensio-actives cationiques
DE2928603A1 (de) * 1979-07-14 1981-02-05 Hoechst Ag Quaternaere ammoniumverbindungen, deren herstellung und deren verwendung als waescheweichspuelmittel

Also Published As

Publication number Publication date
DE3127239A1 (de) 1983-01-20
ES8304917A1 (es) 1983-03-16
EP0069948A1 (fr) 1983-01-19
JPS5818341A (ja) 1983-02-02
AU548545B2 (en) 1985-12-19
AU8577982A (en) 1983-01-13
BR8203996A (pt) 1983-07-05
DE3261758D1 (en) 1985-02-14
ES513706A0 (es) 1983-03-16
US4515723A (en) 1985-05-07
CA1195338A (fr) 1985-10-15

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