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EP0445196A1 - Agents de surface anioniques concentres coulants et procede de preparation - Google Patents

Agents de surface anioniques concentres coulants et procede de preparation

Info

Publication number
EP0445196A1
EP0445196A1 EP90900102A EP90900102A EP0445196A1 EP 0445196 A1 EP0445196 A1 EP 0445196A1 EP 90900102 A EP90900102 A EP 90900102A EP 90900102 A EP90900102 A EP 90900102A EP 0445196 A1 EP0445196 A1 EP 0445196A1
Authority
EP
European Patent Office
Prior art keywords
sulfonation
fatty acids
triethanolamine
sulfur trioxide
anionic surfactants
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.)
Pending
Application number
EP90900102A
Other languages
German (de)
English (en)
Inventor
Ansgar Behler
Ingo Wegener
Horst Ritterbex
Faize Selen
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
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP0445196A1 publication Critical patent/EP0445196A1/fr
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof

Definitions

  • the invention relates to concentrated, flowable anionic surfactants with a water content of ⁇ 1, in particular ⁇ 0.5% by weight.
  • EP-A 243 685 describes a water-dilutable, concentrated, aqueous surfactant composition which contains a nonionic surfactant, solvent and two anionic surfactants from the group formed by triethanolamine salts of linear alkylbenzenesulfonates, Na ethoxysulfate and Na alkanesulfonate.
  • Anhydrous anionic surfactant concentrates which flow at ambient temperature and contain only one surfactant component have hitherto not been disclosed.
  • GB-C 1 278 421 describes sulfonated fatty acids which are neutralized with aqueous bases, for example aqueous triethanolamine and can be hydrolyzed.
  • aqueous bases for example aqueous triethanolamine and can be hydrolyzed.
  • Corresponding water-containing compounds are known from US Pat. No. 2,743,288.
  • the invention is based on the knowledge that anhydrous pastes of a triethanolammonium salt of sulfonated, unsaturated C 1 -C 22 I ' e ' t ' t acids without further additives in the form of diluents or other additives, for example nonionic surfactants, are flowable anionic surfactant concentrates at ambient temperature.
  • triethanolammonium salts of other anionic surfactants which are structurally related to oleic acid sulfonates, do not form free-flowing concentrates; for example, triethanolammonium salts of alpha-sulfo-cig / ig fatty acids and methyl esters thereof in the water-free state are pastes which are no longer flowable at ambient temperature.
  • the invention is directed to concentrated anionic surfactants which are flowable at ambient temperature and have a water content of ⁇ 1, in particular ⁇ 0.5% by weight, which are obtained by sulfonation of unsaturated fatty acids having 16 to 22 carbon atoms with sulfur trioxide at a molar ratio from sulfur trioxide to olefinic double bonds contained in the fatty acids from 0.8 to 1.2: 1, in particular from 0.9 to 1.0: 1, and neutralization of the sulfonation products with triethanolamine.
  • the unsaturated fatty acids with 16 to 22 carbon atoms which can be used according to the invention include synthetic fatty acids with a corresponding structure, but in particular fatty acids of natural, for example vegetable and / or animal origin, including technical mixtures thereof, as are usually used in surfactant chemistry.
  • Typical examples of such fatty acids are palmitoleic, oleic, elaidic, gadolein, brassidin and erucic acid.
  • technical mixtures of fatty acids are used contain at least 50, in particular at least 60% by weight of monounsaturated fatty acids with 18 carbon atoms.
  • the sulfonation of the fatty acids is expediently carried out using conventional technical equipment, in particular of the falling film reactor type.
  • the sulfonation is generally carried out in the absence of solvents; if special circumstances, e.g. If the reaction mixture is too viscous, it can also be carried out in the presence of customary solvents which are inert under the sulfonation conditions.
  • the sulfonation is preferably carried out at from 15 to 90, in particular from 40 to 70 ° C., using a sulfur trioxide stream diluted with an inert carrier gas and having a sulfur trioxide content of 1 to 10% by volume.
  • the sulfonation products are neutralized with an amount of triethanolamine equivalent to sulfur trioxide converted and the carboxyl groups of the fatty acids, it being further advantageous to add the sulfonation products immediately after the sulfonation to triethanolamine. It is also advantageous to subject the neutralized mixture of sulfonation products and triethanolamine to heat treatment at, for example, several hours at at least 60 ° C., in particular at least 80 ° C., in order to decompose reaction products, for example sultones, formed during the sulfonation.
  • the invention further relates to methods for producing the above-mentioned concentrated, flowable anionic surfactants with the features explained above.
  • the sulfonation was carried out in a falling film reactor made of glass, which essentially consisted of a tube surrounded by a heating and cooling jacket, 1100 mm long and 6 mm inside diameter.
  • the head of the reactor was equipped with a feeder for the technical fatty acid mixture and a gas inlet pipe.
  • Gaseous sulfur trioxide, produced by heating oleum, was used in the form of a mixture with nitrogen (5 vol.% SO3).
  • the fatty acid mixture was applied at a constant speed of 550 g / h.
  • the feed of the sulfur trioxide-nitrogen mixture was adjusted so that the molar ratio of sulfur trioxide to unsaturated double bonds of the fatty acid was 0.92.
  • the reaction temperature was kept at 60 ° C. through the reactor jacket.
  • reaction mixture When leaving the reaction zone, the reaction mixture was collected in a beaker in which anhydrous triethano ⁇ lamin was introduced in an amount which is necessary for neutralizing the sulfonic and carboxylic acid groups. The product was then heated to 90 ° C. for two hours. The anhydrous product was flowable at room temperature and had the following key figures:
  • Triethanolammonium sulfate 4.0%

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Detergent Compositions (AREA)

Abstract

On obtient des agents de surface anioniques concentrés coulants à teneur en eau < 1, en particulier < 0,5, % en poids en sulfonant des acides gras insaturés, comportant entre 16 et 22 atomes de carbone, avec de l'anhydre sulfurique, les rapports molaires entre anhydre sulfurique et liaisons doubles oléfiniques contenues dans les acides gras étant compris entre 0,8 et 1,2 pour 1, en particulier entre 0,9 et 1,0 pour 1, et en neutralisant les produits de sulfonation avec triéthanolamine.
EP90900102A 1988-11-28 1989-11-20 Agents de surface anioniques concentres coulants et procede de preparation Pending EP0445196A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3840092 1988-11-28
DE3840092A DE3840092A1 (de) 1988-11-28 1988-11-28 Konzentrierte, fliessfaehige aniontenside und verfahren zu ihrer herstellung

Publications (1)

Publication Number Publication Date
EP0445196A1 true EP0445196A1 (fr) 1991-09-11

Family

ID=6368023

Family Applications (2)

Application Number Title Priority Date Filing Date
EP90900102A Pending EP0445196A1 (fr) 1988-11-28 1989-11-20 Agents de surface anioniques concentres coulants et procede de preparation
EP89121474A Withdrawn EP0371369A1 (fr) 1988-11-28 1989-11-20 Agents tensio-actifs anioniques, concentrés et liquides et leur procédé de préparation

Family Applications After (1)

Application Number Title Priority Date Filing Date
EP89121474A Withdrawn EP0371369A1 (fr) 1988-11-28 1989-11-20 Agents tensio-actifs anioniques, concentrés et liquides et leur procédé de préparation

Country Status (4)

Country Link
EP (2) EP0445196A1 (fr)
JP (1) JPH04502160A (fr)
DE (1) DE3840092A1 (fr)
WO (1) WO1990006300A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3941365A1 (de) * 1989-12-15 1991-06-20 Henkel Kgaa Verfahren zur herstellung von salzen sulfierter fettsaeureglycerinester
DE4134077A1 (de) * 1991-10-15 1993-04-22 Henkel Kgaa Viskose waessrige tensidzubereitungen
DE4320119A1 (de) * 1993-06-18 1994-12-22 Henkel Kgaa Flüssigkristalline wäßrige Tensidzubereitung

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2743288A (en) * 1953-06-24 1956-04-24 Tennessee Corp Production of monosulfonated carboxylic acids and their esters
GB1278421A (en) * 1969-06-27 1972-06-21 Lankro Chem Ltd The sulphonation of unsaturated carboxylic acids

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9006300A1 *

Also Published As

Publication number Publication date
WO1990006300A1 (fr) 1990-06-14
EP0371369A1 (fr) 1990-06-06
JPH04502160A (ja) 1992-04-16
DE3840092A1 (de) 1990-06-07

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