EP0040346B1 - Verfahren zur Raffination des rohen Kondensationsproduktes aus Aminoalkylalkanolaminen und Fettsäuren sowie gewünschtenfalls zur anschliessenden Gewinnung von Amphotensiden mit erhöhter Lagerstabilität - Google Patents

Verfahren zur Raffination des rohen Kondensationsproduktes aus Aminoalkylalkanolaminen und Fettsäuren sowie gewünschtenfalls zur anschliessenden Gewinnung von Amphotensiden mit erhöhter Lagerstabilität Download PDF

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Publication number
EP0040346B1
EP0040346B1 EP81103328A EP81103328A EP0040346B1 EP 0040346 B1 EP0040346 B1 EP 0040346B1 EP 81103328 A EP81103328 A EP 81103328A EP 81103328 A EP81103328 A EP 81103328A EP 0040346 B1 EP0040346 B1 EP 0040346B1
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EP
European Patent Office
Prior art keywords
condensation product
fatty acids
mol
product
crude
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.)
Expired
Application number
EP81103328A
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German (de)
English (en)
French (fr)
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EP0040346A1 (de
Inventor
Uwe Dr. Ploog
Günter Uphues
Manfred Petzold
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
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Henkel AG and Co KGaA
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Publication date
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Priority to AT81103328T priority Critical patent/ATE5815T1/de
Publication of EP0040346A1 publication Critical patent/EP0040346A1/de
Application granted granted Critical
Publication of EP0040346B1 publication Critical patent/EP0040346B1/de
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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
    • C11D1/88—Ampholytes; Electroneutral compounds

Definitions

  • amphoteric surfactants An important process for the production of amphoteric surfactants is based on condensation products of N-monosubstituted alkylenediamines, which are alkylated in a further reaction with alkylating agents, for example sodium chloroacetate. Products based on N-aminoethylethanolamine and fatty acids play a major role as skin-friendly surfactants.
  • the quality of the ampotensides obtained and in particular their storage stability is crucially determined by the purity of the imidazoline derivative obtained in the first condensation step.
  • the reaction between fatty acids and aminoalkylalkanolamines not only proceeds in the direction of the formation of the desired imidazoline derivative, multiple side reactions complicate the course of the reaction.
  • the importance of this aspect has only recently been emphasized again, see EG Lomax "New and improved balanced amphoterics", Manufacturing Chemist and Aerosol News, Volume 50 No. 8, August 1979, pages 39 and 41.
  • EG Lomax New and improved balanced amphoterics
  • the undesirable side reactions in the stage of imidazoline formation can be suppressed by an excess of aminoethylethanolamine, but this excess must be removed at the end of the reaction by distillation.
  • the invention is based on the object of creating improvements in the production of the class of amphoteric surfactants described here, which are characterized in particular by increased storage stability of the amphoteric surfactants.
  • the invention aims to eliminate the troublesome by-products present here by switching on a simple cleaning step on the condensate of aminoalkylalkanolamine and fatty acid obtained in the first place.
  • the aim of the invention is to make the previously expensive detours for obtaining the purest possible condensation product of this first process stage superfluous.
  • the teaching of the invention is based on the surprising finding that the crude condensation product of fatty acids and aminoalkylalkanolamines can be converted by simple alkaline hydrolysis to a refined product which, in the subsequent alkylation and optionally quaternization, provides improved amphoteric surfactants with, in particular, increased storage stability.
  • the invention accordingly relates to a process for refining the crude condensation product from aminoalkylalkanolamines of the general formula in which n is the number 2 or 3, and fatty acids having 6 to 22 carbon atoms and, if desired, for subsequent alkylation and, if appropriate, quaternization of the purified condensation product to amphoteric surfactants with increased storage stability, this process being characterized in that the crude condensation product is obtained from fatty acids and subjecting aminoalkylalkanolamines to alkaline hydrolysis at 70 to 100 ° C.
  • the amount of alkali used in this alkaline hydrolysis is preferably based on the amount of the diamide of the general amount present in the crude condensate formula Voted.
  • the amount of alkali in particular is such that it is preferably present in the crude condensation product in at least an approximately equimolar amount to the diamide.
  • the invention is based on the finding that the content of disruptive by-products in the finished surfactant can be drastically reduced if the fatty acid / amine condensation product is subjected to an alkaline pretreatment in an aqueous medium before a further reaction with alkylating agents.
  • diamide formed in particular in the course of the reaction by aqueous alkali on the tert.
  • Amide group quantitatively split into the monoamide of the primary amino group and fatty acid.
  • the fatty acid forms soap which can remain in the reaction mixture.
  • the alkaline pretreatment according to the invention gives products which remain clear even after dilution for longer than 6 months. Costly cleaning steps such as recovery of the excess amine or distillation of the imidazoline are no longer necessary.
  • the alkaline hydrolytic treatment according to the invention is preferably carried out in the temperature range from 80 to 90 ° C.
  • Alkali hydroxides, especially sodium hydroxide, are particularly suitable as alkalis.
  • the amount of alkali is preferably in the range of about 1 to 3 times the equimolar amount of alkali, based on the diamide present in the crude condensation product. In particular, alkali amounts in the range of 1 to 2 equivalents, based on diamide, are used.
  • the crude condensation product is expediently suspended in an amount of water which corresponds to 0.5 to 10 times, in particular 1 to 5 times, the crude condensation product.
  • the aqueous alkaline hydrolysis is carried out until the diamide present as a by-product is virtually completely eliminated.
  • the diamide content of the crude product and its decrease in the treatment according to the invention can in a known manner, for. B. can be determined by working with ion exchangers.
  • n has the value of 2 or 3; the preferred meaning for n is 2.
  • the most important starting amine in practice of the type concerned here is aminoethylethanolamine.
  • the fatty acids related to the condensation have carbon numbers in the range from 6 to 22, the range from 8 to 18 carbon atoms being particularly important.
  • the carboxylic acids can be present as pure components or as mixtures. They can be of natural and / or synthetic origin.
  • the condensation product pretreated by the alkaline hydrolysis in the sense of the invention is then converted to the finished amphoteric surfactant in a manner known per se.
  • the pretreatment according to the invention proves to be valuable not only for the production of the so-called imidazolinium surfactants, but rather it can be used in many different ways.
  • amphoteric surfactants can have alkylated and optionally quaternized nitrogen in the second reaction stage.
  • the invention comprises the production of such amphoteric surfactants using a condensation precursor which has been treated according to the alkaline hydrolytic process of the invention described.
  • the percentages relate to% by weight.
  • the diamide content is determined as follows: The condensation product is sent as an alcoholic solution through a strongly acidic ion exchanger. The eluate is evaporated and the remaining residue is related to the weight. The amount of diamide can be calculated by determining the S.Z. and the total nitrogen.
  • the finished product is clear and fluid, but shows deposits after 2 days.
  • the end product is clear, but becomes cloudy after 3 days.
  • the reaction was carried out analogously to 3.1, but before adding the chlorohydroxypropanesulfonic acid (sodium salt), stirring was carried out at 80-90 ° C. for 1 hour after the addition of 4.8 g (0.06 mol) of 50% sodium hydroxide solution.
  • the product is still clear after more than 6 months.

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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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Detergent Compositions (AREA)
  • Photovoltaic Devices (AREA)
  • Fats And Perfumes (AREA)
EP81103328A 1980-05-13 1981-05-02 Verfahren zur Raffination des rohen Kondensationsproduktes aus Aminoalkylalkanolaminen und Fettsäuren sowie gewünschtenfalls zur anschliessenden Gewinnung von Amphotensiden mit erhöhter Lagerstabilität Expired EP0040346B1 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT81103328T ATE5815T1 (de) 1980-05-13 1981-05-02 Verfahren zur raffination des rohen kondensationsproduktes aus aminoalkylalkanolaminen und fettsaeuren sowie gewuenschtenfalls zur anschliessenden gewinnung von amphotensiden mit erhoehter lagerstabilitaet.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3018201 1980-05-13
DE19803018201 DE3018201A1 (de) 1980-05-13 1980-05-13 Verfahren zur raffination des rohen kondensationsproduktes aus aminoalkylalkanolaminen und fettsaeuren sowie gewuenschtenfalls zur anschliessenden gewinnung von amphotensiden mit erhoehter lagerstabilitaet

Publications (2)

Publication Number Publication Date
EP0040346A1 EP0040346A1 (de) 1981-11-25
EP0040346B1 true EP0040346B1 (de) 1984-01-11

Family

ID=6102253

Family Applications (1)

Application Number Title Priority Date Filing Date
EP81103328A Expired EP0040346B1 (de) 1980-05-13 1981-05-02 Verfahren zur Raffination des rohen Kondensationsproduktes aus Aminoalkylalkanolaminen und Fettsäuren sowie gewünschtenfalls zur anschliessenden Gewinnung von Amphotensiden mit erhöhter Lagerstabilität

Country Status (9)

Country Link
EP (1) EP0040346B1 (enrdf_load_stackoverflow)
JP (1) JPS5716846A (enrdf_load_stackoverflow)
AT (1) ATE5815T1 (enrdf_load_stackoverflow)
AU (1) AU541532B2 (enrdf_load_stackoverflow)
BR (1) BR8102948A (enrdf_load_stackoverflow)
CA (1) CA1214778A (enrdf_load_stackoverflow)
DE (2) DE3018201A1 (enrdf_load_stackoverflow)
ES (1) ES502137A0 (enrdf_load_stackoverflow)
MX (1) MX156685A (enrdf_load_stackoverflow)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3444864A1 (de) * 1984-12-08 1986-06-12 Henkel KGaA, 4000 Düsseldorf Verfahren zur fettung von leder und pelzen
DE3641871A1 (de) * 1986-12-08 1988-06-09 Henkel Kgaa Verfahren zur herstellung duennfluessiger amphotenside
DE4038983A1 (de) * 1990-12-06 1992-06-11 Henkel Kgaa Verfahren zur herstellung duennfluessiger imidazoliniumtenside durch quaternierung von 1-hydroxyethyl-2-alkylimidazolinen
DE4240154A1 (de) * 1992-11-30 1994-06-01 Henkel Kgaa Verfahren zur Herstellung dünnflüssiger, lagerstabiler Amphotenside
CA2132289A1 (en) * 1993-10-12 1995-04-13 Bharat Desai Higher purity imidazoline based amphoacetate surfactants and processes for the preparation thereof
DE19715383A1 (de) * 1997-04-14 1998-10-15 Clariant Gmbh Amphoglycinate als Korrosionsschutzmittel für Eisen- und Nichteisenmetalle

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5938221B2 (ja) * 1976-01-20 1984-09-14 ライオン株式会社 第四級アンモニウム塩の製造方法
JPS5951532B2 (ja) * 1976-09-03 1984-12-14 川研フアインケミカル株式会社 新規なアミンアミド化合物，その製造方法および前記アミンアミド化合物を含有する界面活性剤
JPS5368721A (en) * 1976-12-01 1978-06-19 Lion Corp Disubstd. aliphatic carboxylic acid amide amines, and detergents and cosmeticcompositions containing the same
NO150275C (no) * 1977-08-18 1984-09-19 Albright & Wilson Organiske nitrogenholdige forbindelser og fremgangsmaate til deres fremsilling, samt anvendelse av forbindelsene i sjampo

Also Published As

Publication number Publication date
ATE5815T1 (de) 1984-01-15
ES8203830A1 (es) 1982-04-01
BR8102948A (pt) 1982-02-02
AU7051181A (en) 1981-11-19
EP0040346A1 (de) 1981-11-25
CA1214778A (en) 1986-12-02
DE3018201A1 (de) 1981-11-19
ES502137A0 (es) 1982-04-01
DE3161875D1 (en) 1984-02-16
MX156685A (es) 1988-09-26
JPH0249299B2 (enrdf_load_stackoverflow) 1990-10-29
AU541532B2 (en) 1985-01-10
JPS5716846A (en) 1982-01-28

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