WO1992015661A1 - Adjuvant organique a proprietes tensio-actives - Google Patents

Adjuvant organique a proprietes tensio-actives Download PDF

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Publication number
WO1992015661A1
WO1992015661A1 PCT/EP1992/000457 EP9200457W WO9215661A1 WO 1992015661 A1 WO1992015661 A1 WO 1992015661A1 EP 9200457 W EP9200457 W EP 9200457W WO 9215661 A1 WO9215661 A1 WO 9215661A1
Authority
WO
WIPO (PCT)
Prior art keywords
sulfonation products
fatty acids
unsaturated fatty
builder
acid
Prior art date
Application number
PCT/EP1992/000457
Other languages
German (de)
English (en)
Inventor
Claus-Peter KURZENDÖRFER
Birgit Burg
Heribert Kaiser
Ulrich Kratzel
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 JP4504964A priority Critical patent/JPH06505048A/ja
Publication of WO1992015661A1 publication Critical patent/WO1992015661A1/fr

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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
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/28—Sulfonation products derived from fatty acids or their derivatives, e.g. esters, amides

Definitions

  • the invention relates to organic builders with surfactant properties which are used in addition to a detergent, in particular if a poor washing result is to be expected at high water hardness.
  • synthetic zeolites for example SA-SIL ( R )
  • the object of the invention was therefore to develop agents which are both builder-active and surfactant-active.
  • the invention relates to organic builders with surfactant properties which can be used as additives with detergents or for washing processes, characterized by a content of sulfonation products of unsaturated fatty acids of the formula (I),
  • Rl represents an aliphatic hydrocarbon radical having 16 to 24 carbon atoms and 1, 2, 3, 4 or 5 double bonds.
  • sulfonation products of unsaturated fatty acids which are known to be surface-active, also have builder properties.
  • the invention is based on the knowledge that sulfonation products are more unsaturated Fatty acids behave in a stoichiometric as well as in a stoichiometric ratio to alkaline earth ions in analogy to threshold-active substances, provided that the poorly soluble alkaline earth metal salts are formed in the presence of the sulfonation products. In this way, a colloidal distribution of alkaline earth metal carbonates and silicates is brought about on the one hand, and on the other hand, calcium growth is inhibited.
  • the sulfonation products of unsaturated fatty acids can be used as surfactant, completely biodegradable builder components in liquid or powder detergents, especially in the energy-saving low-temperature range.
  • the invention also includes the knowledge that the sulfonation products of unsaturated fatty acids, when used in soap-containing detergents, inhibit the deposition of precipitated lime soap on heating elements even in a substoichiometric ratio.
  • the sulfonation products of unsaturated fatty acids are known surfactants which can be obtained by the relevant processes in preparative organic chemistry.
  • German patent application DE 40 19 713 A1 one can start from oleic acid, for example, which is first sulfonated at temperatures around 15 ° C. with gaseous sulfur trioxide and then hydrolyzed and neutralized.
  • Rl represents an aliphatic hydrocarbon radical having 16 to 24 carbon atoms and 1, 2, 3, 4 or 5 double bonds.
  • Typical examples of this are palmitoleic acid, oleic acid, elaidic acid, petroselinic acid, chaulograsic acid, linoleic acid, linolenic acid, gadoleic acid, arachidonic acid, erucic acid or clupanodonic acid.
  • the use of oleic acid is preferred.
  • the sulfonation products of unsaturated fatty acids can also be derived from technical fatty acid cuts, such as those obtained by pressure splitting of natural fats and oils, for example sunflower oil, rapeseed oil, coriander oil, chaulmoogra oil, linseed oil and cottonseed oil , Peanut oil, beef tallow or fish oil.
  • the sulfonation products can also be derived from technical fatty acids which contain a proportion of saturated fatty acids, provided that this is less than 50% by weight, based on the fatty acid.
  • the sulfonation products can be used in the form of the sulfonic acids.
  • the sulfonation products are preferably used in the form of their alkali metal, alkaline earth metal or ammonium salts.
  • the use of oleic acid sulfonate di-sodium salt is preferred.
  • the sulfonation products of unsaturated fatty acids can be used alone or in combination with water softening agents. Accordingly, the water-softening agents can have a content of sulfonation products of unsaturated fatty acids of 10 to 100% by weight, based on the agent. Possible water-softening substances that can be used in combination with the sulfonation products of unsaturated fatty acids are:
  • Fine crystalline, synthetic, bound water-containing zeolites of the NaA type which have a calcium binding capacity in the range from 100 to 200 mg CaO / g and an average particle size in the range from 1 to 10 ⁇ m.
  • zeolites of the NaA type which have a calcium binding capacity in the range from 100 to 200 mg CaO / g and an average particle size in the range from 1 to 10 ⁇ m.
  • Polymeric polycarboxylates derived from acrylic acid and their copolymers with maleic acid in the form of the sodium salts can have, for example, molecular weights of 2,000 to 200,000, preferably 5,000 to 100,000.
  • the copolymers of acrylic acid or methacrylic acid with maleic acid as described, for example, in European patent application EP 0 025 551 A1, have proven particularly suitable. These are copolymers which contain 40 to 90% by weight of acrylic acid. Those copolymers in which 50 to 85% by weight of acrylic acid and 50 to 15% by weight of maleic acid are present are particularly preferred.
  • Alkali salts of monomeric polycarboxylic acid such as, for example, nitrilotriacetate tri sodium salt, ethylenedia intetraacetate tetra sodium salt or citric acid tri sodium salt.
  • the weight ratio between the sulfonation products on the one hand and the sum of the water-softening substances on the other hand is 10: 1 to 1:10, in particular 8: 1 to 1: 8.
  • the sulfonation products of unsaturated fatty acids are suitable as organic builders with surfactant properties and can be used as additives for detergents or in the washing process.
  • Another object of the invention therefore relates to the use of sulfonation products of unsaturated fatty acids of the formula (I),
  • R 1 represents an aliphatic hydrocarbon radical with 11 to 24 carbon atoms and 1, 2, 3, 4 or 5 double bonds, as an organic builder with surfactant properties in detergents or for washing processes.
  • ABS dodecylbenzenesulfonate
  • recipe deposits after 5 washing cycles * mg / 2g tissue
  • a washing process with a temperature program from 25 to 90 ° C. was simulated over a period of 70 min and then after 1, 3 and 6 washes (WG) the amount of lime sulfo soap or lime soap deposited on the heating rod and vessel wall was determined. The results are summarized in Table 5.

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)
  • Detergent Compositions (AREA)

Abstract

Les produits de la sulfonation d'acides gras insaturés répondant à la formule (I): R1-COOH, dans laquelle R1 représente un reste hydrocarbure aliphatique ayant 16 à 24 atomes de carbone et 1, 2, 3, 4, ou 5 liaisons doubles, sont utiles comme adjuvants ayant des propriétés tensio-actives dans des produits ou des processus de lavage.
PCT/EP1992/000457 1991-03-11 1992-03-02 Adjuvant organique a proprietes tensio-actives WO1992015661A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP4504964A JPH06505048A (ja) 1991-03-11 1992-03-02 界面活性を有する有機ビルダー

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19914107731 DE4107731A1 (de) 1991-03-11 1991-03-11 Organische builder mit tensideigenschaften
DEP4107731.8 1991-03-11

Publications (1)

Publication Number Publication Date
WO1992015661A1 true WO1992015661A1 (fr) 1992-09-17

Family

ID=6426967

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1992/000457 WO1992015661A1 (fr) 1991-03-11 1992-03-02 Adjuvant organique a proprietes tensio-actives

Country Status (4)

Country Link
EP (1) EP0575372A1 (fr)
JP (1) JPH06505048A (fr)
DE (1) DE4107731A1 (fr)
WO (1) WO1992015661A1 (fr)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2107437A5 (fr) * 1970-09-09 1972-05-05 Unilever Nv
FR2118670A5 (fr) * 1970-12-16 1972-07-28 Unilever Nv
EP0070191A1 (fr) * 1981-07-15 1983-01-19 Unilever Plc Additifs de détergentes et compositions détergentes les contenant
EP0360392A2 (fr) * 1988-07-26 1990-03-28 Unilever Plc Composition détergente avec des propriétés adoucissantes pour le linge

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2107437A5 (fr) * 1970-09-09 1972-05-05 Unilever Nv
FR2118670A5 (fr) * 1970-12-16 1972-07-28 Unilever Nv
EP0070191A1 (fr) * 1981-07-15 1983-01-19 Unilever Plc Additifs de détergentes et compositions détergentes les contenant
EP0360392A2 (fr) * 1988-07-26 1990-03-28 Unilever Plc Composition détergente avec des propriétés adoucissantes pour le linge

Also Published As

Publication number Publication date
JPH06505048A (ja) 1994-06-09
DE4107731A1 (de) 1992-09-17
EP0575372A1 (fr) 1993-12-29

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