EP0071993A1 - Esters d'acides alkylsulfonamidoalcanecarboxyliques, leur procédé de préparation et leur utilisation - Google Patents

Esters d'acides alkylsulfonamidoalcanecarboxyliques, leur procédé de préparation et leur utilisation Download PDF

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Publication number
EP0071993A1
EP0071993A1 EP82107116A EP82107116A EP0071993A1 EP 0071993 A1 EP0071993 A1 EP 0071993A1 EP 82107116 A EP82107116 A EP 82107116A EP 82107116 A EP82107116 A EP 82107116A EP 0071993 A1 EP0071993 A1 EP 0071993A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
formula
mol
carbon atoms
acid esters
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.)
Withdrawn
Application number
EP82107116A
Other languages
German (de)
English (en)
Inventor
Werner Dr. Ritschel
Adolf Dr. May
Hans-Walter Dr. Bücking
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.)
Hoechst AG
Original Assignee
Hoechst AG
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 Hoechst AG filed Critical Hoechst AG
Publication of EP0071993A1 publication Critical patent/EP0071993A1/fr
Withdrawn legal-status Critical Current

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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

  • the invention relates to quaternary alkyl sulfonamidoalkyl carboxylic acid esters of the formula 1 in which R 1 is alkyl with 8 to 22 C atoms, - (Z) n - an oxalkyl or polyoxalkyl radical with n oxethyl and / or oxypropyl units, R 2 , R 3 and R 4 alkyl with 1 to 4 C atoms, one Radical - (Z) n - or R 2 is also hydrogen, R 5 is alkyl or alkenyl having 8 to 24 carbon atoms, m is a number from 2 to 6, n O or a number from 1 to 10, y is a number from 1 to 4 and A are chloride or bromide.
  • the quaternary compounds according to the invention are prepared by firstly using an alkanesulfonyl chloride of the formula 2 with an amine of formula 3 converted to alkanesulfonamido-amines of the formula 4.
  • the alkanesulfonamido-amines of the formula 4 can also be obtained by an alkanesulfonyl chloride of the formula 2 first with an unsubstituted amine of the formula 6 to a compound of formula 7 implemented and then converted into the compound of formula 4 by reaction with ethylene oxide and / or propylene oxide or with an alkylating agent such as dimethyl sulfate or methyl chloride.
  • the alkanesulfonamido-amines of the formula 4 are at elevated temperature with a haloacetic acid ester of the formula 5 where X means halogen, further implemented.
  • the compound of formula 1 is obtained
  • amines of the formula 3 are N.N-dimethylethylenediamine, trihydroxyethylethylenediamine, N.N-dihydroxyethylenediamine, as well as the corresponding propylenediamines, tetra- and hexamethylenediamines. Also suitable are alkylated or oxyethylated or oxypropylated triamines and tetramines, such as diethylenetriamines or triethylenetetramines, which have at least one hydrogen on a nitrogen atom.
  • Suitable amines of the formula 6 are in particular ethylene or propylene diamine, tetramethylene or hexamethylene diamine as well as diethylene triamine and triethylene tetramine.
  • the reaction of the alkanesulfochloride with the unsubstituted amine of the formula 6 takes place in the same way.
  • the compound of formula 7 obtained here is known in a known manner by reaction with ethylene oxide and / or propylene oxide or by reaction with an alkylating agent in the presence of NaOH or KOH at elevated temperature, e.g. at about 50 to 80 ° C, converted into the compound of formula 4.
  • 1 mol of a compound of formula 4 is heated without solvent with 1 mol of a haloacetic acid ester of formula 5 with stirring to about 70 to 140 ° C, preferably 90 to 110 ° C, whereby the quaternary compound of formula 1 is formed.
  • the quaternary reaction product can be immediately adjusted to the desired concentration with water.
  • the compounds of 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 about 1 to 15% by weight, usually 4 to 10% by weight of the compounds of formula 1 following the washing of the textile material in the given last rinse bath.
  • These fabric softener dispersions can also contain other substances and auxiliaries that are commonly used in fabric softeners. These include, for example, cationic or nonionic surface-active substances, electrolytes, acidifying agents, organic complexing agents, optical brighteners agents or solubilizers as well as colors 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, regulate the pH or increase the cold stability of the solutions.
  • the compounds according to the invention give any textile materials, especially those made from 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.

Landscapes

  • 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
EP82107116A 1981-08-11 1982-08-06 Esters d'acides alkylsulfonamidoalcanecarboxyliques, leur procédé de préparation et leur utilisation Withdrawn EP0071993A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3131683 1981-08-11
DE19813131683 DE3131683A1 (de) 1981-08-11 1981-08-11 "alkyl-sulfonamido-alkylcarbonsaeure-ester, verfahren zu deren herstellung und deren verwendung"

Publications (1)

Publication Number Publication Date
EP0071993A1 true EP0071993A1 (fr) 1983-02-16

Family

ID=6139058

Family Applications (1)

Application Number Title Priority Date Filing Date
EP82107116A Withdrawn EP0071993A1 (fr) 1981-08-11 1982-08-06 Esters d'acides alkylsulfonamidoalcanecarboxyliques, leur procédé de préparation et leur utilisation

Country Status (3)

Country Link
EP (1) EP0071993A1 (fr)
JP (1) JPS5841859A (fr)
DE (1) DE3131683A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0468856A1 (fr) * 1990-07-25 1992-01-29 L'oreal Composés solubilisants et/ou dispersants, procédé de préparation et compositions les contenant

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2238740A1 (de) * 1972-08-05 1974-02-07 Bayer Ag Perfluoralkylgruppenhaltige polyaether und verfahren zu deren herstellung
GB1583363A (en) * 1977-05-12 1981-01-28 Ugine Kuhlmann Amphoteric fluorinated sulphonamides

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2238740A1 (de) * 1972-08-05 1974-02-07 Bayer Ag Perfluoralkylgruppenhaltige polyaether und verfahren zu deren herstellung
GB1583363A (en) * 1977-05-12 1981-01-28 Ugine Kuhlmann Amphoteric fluorinated sulphonamides

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0468856A1 (fr) * 1990-07-25 1992-01-29 L'oreal Composés solubilisants et/ou dispersants, procédé de préparation et compositions les contenant
FR2665157A1 (fr) * 1990-07-25 1992-01-31 Oreal Composes solubilisants et/ou dispersants du type tensio-actif quaternaire, procede de preparation, utilisation comme additif dans des compositions et compositions cosmetiques ou dermopharmaceutiques en comportant.
US5182407A (en) * 1990-07-25 1993-01-26 L'oreal Solubilizing and/or dispersant compounds, preparation process and compositions containing them

Also Published As

Publication number Publication date
DE3131683A1 (de) 1983-02-24
JPS5841859A (ja) 1983-03-11

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Legal Events

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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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AK Designated contracting states

Designated state(s): DE FR GB IT SE

STAA Information on the status of an ep patent application or granted ep patent

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17P Request for examination filed

Effective date: 19830420

18W Application withdrawn

Withdrawal date: 19830426

RIN1 Information on inventor provided before grant (corrected)

Inventor name: MAY, ADOLF, DR.

Inventor name: RITSCHEL, WERNER, DR.

Inventor name: BUECKING, HANS-WALTER, DR.