WO1991004963A1 - Sels d'esters sulfones d'acides dicarboxyliques avec des alcools ou alcoxylats gras insatures, leur procede de fabrication et leur utilisation comme agents tensio-actifs - Google Patents

Sels d'esters sulfones d'acides dicarboxyliques avec des alcools ou alcoxylats gras insatures, leur procede de fabrication et leur utilisation comme agents tensio-actifs Download PDF

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Publication number
WO1991004963A1
WO1991004963A1 PCT/EP1990/001590 EP9001590W WO9104963A1 WO 1991004963 A1 WO1991004963 A1 WO 1991004963A1 EP 9001590 W EP9001590 W EP 9001590W WO 9104963 A1 WO9104963 A1 WO 9104963A1
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WIPO (PCT)
Prior art keywords
sulfonation
esters
general formula
salts
fatty alcohols
Prior art date
Application number
PCT/EP1990/001590
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German (de)
English (en)
Inventor
Ansgar Behler
Original Assignee
Henkel Kommanditgesellschaft Auf Aktien
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Publication date
Application filed by Henkel Kommanditgesellschaft Auf Aktien filed Critical Henkel Kommanditgesellschaft Auf Aktien
Publication of WO1991004963A1 publication Critical patent/WO1991004963A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
    • C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C309/07—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton
    • C07C309/12—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton containing esterified hydroxy groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
    • C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C309/07—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton
    • C07C309/09—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton containing etherified hydroxy groups bound to the carbon skeleton
    • C07C309/10—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton containing etherified hydroxy groups bound to the carbon skeleton with the oxygen atom of at least one of the etherified hydroxy groups further bound to an acyclic carbon atom

Definitions

  • Salts of sulfonated esters of dicarboxylic acids with unsaturated fatty alcohols or alkoxylates processes for their preparation and their use as surface-active agents.
  • the invention relates to salts of sulfonated esters of dicarboxylic acids with unsaturated fatty alcohols or with addition products of ethylene oxide and / or propylene oxide onto unsaturated fatty alcohols, obtainable by sulfonation of dicarboxylic acid esters of the general formula I
  • A is a vinylene or an ethylene group
  • R 1 is a straight-chain alkenyl group with 16 to 22 carbon atoms
  • R 2 is hydrogen, an alkyl group with 1 to 22 carbon atoms or a straight-chain alkenyl group with 16 to 22 carbon atoms,
  • n and q each have numbers in the range from 0 to 20 and and p each the numbers 2 and / or 3
  • sulfur trioxide in the molar ratio of sulfur trioxide to double bonds present in the alkenyl groups from 0.5 to 1.8: 1, in particular 0.6 to 1.5: 1, and neutralization of the sulfonation products with bases.
  • dicarboxylic acid ester sulfonates have interesting surface-active properties and their properties as surface-active agents can be adapted to the respective requirements by varying the number of ethyleneoxy and / or propyleneoxy units contained in them.
  • Typical examples of such monounsaturated fatty alcohols are palmitoleyl alcohol, oleyl alcohol, elaidyl alcohol, gadoleyl alcohol, arachidone alcohol, eruca alcohol and brassidyl alcohol, which, as is common in fat chemistry, are often used in the form of their technical mixtures with other, saturated and / or unsaturated fatty alcohols; the technical mixtures of these fatty alcohols are in turn accessible from natural renewable raw materials, in particular animal or vegetable fats and oils.
  • the technical fatty alcohol mixtures used to produce the starting compounds of the general formula I can also additionally contain small amounts of polyunsaturated fatty alcohols such as linoleyl alcohol or linolenyl alcohol, the residues of which then appear in the starting compounds do not interfere with the preparation of the dicarboxylic acid ester sulfonates of the invention.
  • the corresponding addition products of ethylene oxide and / or propylene oxide (in the case of a random or block distribution of the propyleneoxy units in the case of mixed addition products) can also be used for esterification with the aforementioned dicarboxylic acids; the aforementioned adducts can contain up to 20 ethyleneoxy and / or propyleneoxy units.
  • the first step is to obtain those for the preparation of the dicarboxylic acid ester sulfonates
  • the free carboxyl function of these half-esters can also be esterified with alcohols of the formula R 2 -0H, specifically with monoalkanols having 1 to 22 carbon atoms, for example methanol, ethanol, propanol, butanol, pentanol, hexanol, octanol, decanol, dodecanol, tetradecanol , Hexadecanol, Octadecanol, Eicosanol and Docosanol, which are also of natural or synthetic origin and can be used in the form of their technical mixtures.
  • alcohols of the formula R 2 -0H specifically with monoalkanols having 1 to 22 carbon atoms, for example methanol, ethanol, propanol, butanol, pentanol, hexanol, octanol, decanol, dodecanol, tetradecanol , Hexadecano
  • esterification of the free carboxyl group of the half esters can also be carried out with the abovementioned unsaturated fatty alcohols R1_0H, so that ultimately full esters of maleic or succinic acid are obtained which each have two unsaturated fatty alcohol residues and are also suitable for the preparation of the dicarboxylic acid ester sulfonates of the invention .
  • addition products of ethylene oxide and / or propylene oxide onto the monoalkanols or fatty alcohols can also be converted here the free carboxyl function of the half esters can be used in an ester function.
  • the dicarboxylic acid ester sulfonates are obtainable from dicarboxylic acid esters of the general formula I which are derived from maleic or fumaric acid, ie in the general formula I A is a vinylene group and R-, R 2 , m, n , p and q are as defined above.
  • dicarboxylic acid ester sulfonates obtainable by sulfonating dicarboxylic acid esters of the general formula I in which m and p each have the number 2 and n and q each have numbers in the range from 0 to 10, in particular from
  • fatty alcohol ethoxylates 1 residues of fatty alcohols or fatty alcohol ethoxylates, it being possible for the fatty alcohol ethoxylates to contain 1 to 10, in particular 1 to 5, ethylene oxide units.
  • radical R- of the dicarboxylic acid esters of the general formula I and optionally also the radical R 2 are derived from oleyl alcohol.
  • the sulfonated dicarboxylic esters of the general formula I are used with aqueous bases, for example with LiOH, sodium hydroxide solution, potassium hydroxide solution, ammonia, mono-C 1 -C 4 -alkylamines, di-C 1 -C 4 -alkylamines , Tri-C4-C4-alkylamines, mono- C ⁇ -C4-hydroxyalkylamines, di-C ⁇ -C4-hydroxyalkylamines, tri- C ⁇ -C4-hydroxyalkylamines, Mg (OH) 2 / Ca (OH) 2 / Sr (0H) 2nd and Ba (OH) 2 neutralized; the use of aqueous sodium hydroxide solution is preferred.
  • the neutralization should be carried out gently, ie with short reaction times and not too high reaction temperatures and while maintaining a pH in the range from about 6 to 8, if necessary with constant addition of the bases, so that the ester bonds are not cleaved at the same time as the neutralization.
  • R3 is a group of the formula purple or Illb
  • M is a cation equivalent, the sum of x + y + z giving a number in the range from 14 to 18,
  • Cation equivalent is to be understood as the cationic remainder of the bases used for neutralization, for example according to the list above.
  • R 3 is the residue of a fatty alcohol with 18 carbon atoms of the formula lilac or Illb and
  • n is a number in the range from 0 to 10, in particular from 0 to 5,
  • the group R 3 and optionally the group R 4 are preferably derived from a sulfonated oleyl radical.
  • the invention further relates to a process for the preparation of salts of sulfonated esters of dicarboxylic acids with unsaturated fatty alcohols or with addition products of ethylene oxide and / or propylene oxide onto unsaturated fatty alcohols, characterized by those described above Process features.
  • the dicarboxylic acid ester sulfonates of the invention can be prepared largely analogously to a process for the production of monocarboxylic acid ester sulfonates known from DE-A 37 25 030.
  • the invention relates to the use of the salts of sulfonated esters of dicarboxylic acids with unsaturated fatty alcohols or with addition products of ethylene oxide and / or propylene oxide onto unsaturated fatty alcohols of the type explained above as surface-active agents.
  • Example 1 was repeated, working with a molar ratio of sulfur trioxide to olefinic double bonds present in the starting material of 1.2: 1.
  • Example 4 Analogous to the procedure described in Example 1, 154.8 g (0.25 mol) of a half ester of maleic acid with an adduct of 5 mol of ethylene oxide with an industrial oleyl alcohol of the composition given in Example 1 were mixed with 24.0 g (0.3 mol ) SO3 sulfonated at 45 ° C. Example 4.
  • Example 2 Analogously to the manner described in Example 1, 138.9 g (0.13 mol) of a diester of maleic acid with an adduct of 5 mol of ethylene oxide with an industrial oleyl alcohol of the composition given in Example 1 were mixed with 22.0 g (0.275 mol) of sulfur trioxide implemented. The sulfonation product was neutralized as indicated in Example 1.

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

Abstract

Des sels d'esters sulfonés d'acides dicarboxyliques avec des alcools gras insaturés ou avec des produits d'addition d'oxyde d'éthylène et/ou d'oxyde de propylène à des alcools gras insaturés, s'obtenant par sulfonation d'esters d'acides dicarboxyliques de formule générale (I): R1O-(CmH2mO)n-CO-A-CO-(OCpH2p)q-OR2, où A est un groupe vinylène ou éthylène, R1 un groupe alkényle à chaîne droite avec 16 à 22 atomes de carbone, R2 est hydrogène, un groupe alkyle avec 1 à 22 atomes de carbone ou un groupe alkényle à chaîne droite avec 16 à 22 atomes de carbone, n et q sont respectivement des nombres compris entre 0 et 20 et m et p respectivement les nombres 2 et/ou 3, avec du trioxyde de soufre dans un rapport molaire du trioxyde de soufre aux doubles liaisons présentes dans les groupes alkényle de 0,5 à 1,8:1, notamment 0,6 à 1,5:1, et par neutralisation des produits de sulfonation avec des bases, sont des composés avec d'intéressantes propriétés tensio-actives.
PCT/EP1990/001590 1989-09-28 1990-09-19 Sels d'esters sulfones d'acides dicarboxyliques avec des alcools ou alcoxylats gras insatures, leur procede de fabrication et leur utilisation comme agents tensio-actifs WO1991004963A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3932492A DE3932492A1 (de) 1989-09-28 1989-09-28 Salze von sulfonierten estern von dicarbonsaeuren mit ungesaettigten fettalkoholen bzw. -alkoxylaten, verfahren zu ihrer herstellung und ihre verwendung als oberflaechenaktive mittel
DEP3932492.3 1989-09-28

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WO1991004963A1 true WO1991004963A1 (fr) 1991-04-18

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WO (1) WO1991004963A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992002595A1 (fr) * 1990-08-06 1992-02-20 Henkel Kommanditgesellschaft Auf Aktien Utilisation de sels tensio-actifs de sulfonate d'ester dans des solutions de curage et dans d'autres agents de traitement de puits de forage a base d'eau et d'huile
WO1997009304A1 (fr) * 1995-09-01 1997-03-13 HÜLS Aktiengesellschaft Composes amphiphiles anioniques comportant plusieurs groupes hydrophiles et hydrophobes a base de derives d'acetylene

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19505367A1 (de) * 1995-02-17 1996-10-24 Huels Chemische Werke Ag Amphiphile Verbindungen mit mindestens zwei hydrophilen und mindestens zwei hydrophoben Gruppen auf der Basis von Dicarbonsäurediestern
DE19633497A1 (de) 1996-08-20 1998-02-26 Huels Chemische Werke Ag Amphiphile Verbindungen mit mindestens zwei hydrophilen und mindestens zwei hydrophoben Gruppen auf der Basis von Dicarbonsäurediestern

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2402823A (en) * 1943-04-09 1946-06-25 Monsanto Chemicals Surface-active agents
DE2046049A1 (de) * 1969-09-18 1971-04-29 Castrol Ltd Neue Sulfonsäuren und ihre Metallsalze, Verfahren zu ihrer Herstellung sowie ihre Verwendung in Schmiermittelzusammensetzungen
FR2259149A1 (fr) * 1974-01-28 1975-08-22 Texaco Development Corp
US3903138A (en) * 1974-04-08 1975-09-02 Chevron Res Alkyl succinic acid esters of hydroxyalkyl sulfonic acids

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2402823A (en) * 1943-04-09 1946-06-25 Monsanto Chemicals Surface-active agents
DE2046049A1 (de) * 1969-09-18 1971-04-29 Castrol Ltd Neue Sulfonsäuren und ihre Metallsalze, Verfahren zu ihrer Herstellung sowie ihre Verwendung in Schmiermittelzusammensetzungen
FR2259149A1 (fr) * 1974-01-28 1975-08-22 Texaco Development Corp
US3903138A (en) * 1974-04-08 1975-09-02 Chevron Res Alkyl succinic acid esters of hydroxyalkyl sulfonic acids

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992002595A1 (fr) * 1990-08-06 1992-02-20 Henkel Kommanditgesellschaft Auf Aktien Utilisation de sels tensio-actifs de sulfonate d'ester dans des solutions de curage et dans d'autres agents de traitement de puits de forage a base d'eau et d'huile
WO1997009304A1 (fr) * 1995-09-01 1997-03-13 HÜLS Aktiengesellschaft Composes amphiphiles anioniques comportant plusieurs groupes hydrophiles et hydrophobes a base de derives d'acetylene

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