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WO1999032432A1 - Aminoamides d'acide gras a dispersibilite amelioree - Google Patents

Aminoamides d'acide gras a dispersibilite amelioree Download PDF

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Publication number
WO1999032432A1
WO1999032432A1 PCT/EP1998/008046 EP9808046W WO9932432A1 WO 1999032432 A1 WO1999032432 A1 WO 1999032432A1 EP 9808046 W EP9808046 W EP 9808046W WO 9932432 A1 WO9932432 A1 WO 9932432A1
Authority
WO
WIPO (PCT)
Prior art keywords
fatty acid
acid
formula
carbon atoms
aminoamides
Prior art date
Application number
PCT/EP1998/008046
Other languages
German (de)
English (en)
Inventor
Günter Uphues
Ansgar Behler
Marion Elsner
Bernd Wahle
Yvonne Reichert
Original Assignee
Cognis Deutschland Gmbh
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 Cognis Deutschland Gmbh filed Critical Cognis Deutschland Gmbh
Publication of WO1999032432A1 publication Critical patent/WO1999032432A1/fr

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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/402—Amides imides, sulfamic acids
    • D06M13/419—Amides having nitrogen atoms of amide groups substituted by hydroxyalkyl or by etherified or esterified hydroxyalkyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
    • C07C233/35—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/36—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton

Definitions

  • the invention relates to a process for the preparation of fatty acid aminoamides with improved cold water dispersibility, obtainable by condensation of fatty acid triglycerides with polyvalent amines, partial neutralization and addition of selected dispersion accelerators, and the use of the fatty acid aminoamides mentioned as textile treatment agents.
  • US Pat. No. 2,340,881 describes aqueous dispersions of condensation products, made from a hydroxyalkyl polyamine and a fatty acid glyceride, which improve the lubricity and the softness of the textiles treated with them.
  • US 3,454,494 relates to fatty acid condensation products with an addition of dispersing polyglycol ethers.
  • German patent DE-PS 19 22 046 describes detergents containing fatty acid condensation products which contain fatty acid glycerides with a dispersing action; in the German patent DE-PS 19 22 047 these are Fabrics also as textile softeners for especially liquid ones
  • Laundry treatment agent described. These and similar agents can be dispersed in water by placing them in hot water and usually applying high shear forces, or by dispersing the condensation product, which has still been melted, in water. Because of the effort required, the manufacturer usually carries out the dispersion and supplies the user with the dispersions, which is associated with the storage and transport of considerable amounts of water and is therefore not economically viable.
  • the dispersibility of such substances can be increased by adding suitable dispersion accelerators, for example glucose , Sorbitol, mannitol, pentaerythritol, alkyl polyglucosides, sorbitan esters, gelatin and unsaturated fatty alcohols and fatty acids.
  • suitable dispersion accelerators for example glucose , Sorbitol, mannitol, pentaerythritol, alkyl polyglucosides, sorbitan esters, gelatin and unsaturated fatty alcohols and fatty acids.
  • suitable dispersion accelerators for example glucose , Sorbitol, mannitol, pentaerythritol, alkyl polyglucosides, sorbitan esters, gelatin and unsaturated fatty alcohols and fatty acids.
  • Products are also established on the market that contain mixtures of highly ethoxylated tallow alcohols and 1,2-propylene glycol as dispersion accelerators.
  • the object of the invention was therefore to provide fatty acid aminoamides which are free from the disadvantages described.
  • the invention relates to fatty acid aminoamides with improved cold water dispersibility, which are obtained by triglycerides of fatty acids having 8 to 22 carbon atoms and 0 or 1 to 3 double bonds with polyamines of the general formula (I)
  • R 1 is hydrogen, a methyl, ethyl, hydroxyethyl or a - (CH 2 ) n -NH-R 2 - group
  • R 2 is hydrogen, a methyl, ethyl or hydroxyethyl group
  • n is a number of 2 to 4 and m stands for numbers from 1 to 4, condensed and then partially neutralized unreacted amino groups with acids, characterized in that compounds of the formula (II) are added after the neutralization
  • R 3 is an alkyl or alkenyl radical with 12 to 22 carbon atoms and R 4 is an alkyl radical with 7 to 21 carbon atoms and p is 0 or numbers from 1 to 5 and q is a number between 1 and 5.
  • Natural or synthetic glycerides are suitable as starting materials.
  • fatty acid components are caproic acid, capric acid, caprylic acid, Lauric acid, myristic acid, palmitic acid, palmoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid, elaeostearic acid, arachidic acid, gadoleic acid, behenic acid and erucic acid as well as their technical mixtures as they occur, for example, in the pressure splitting of fats and oils .
  • palm oil or tallow is used in hydrogenated form; in these natural triglycerides the fatty acid part has 16 to 18 carbon atoms and 0 and / or 1 double bond.
  • the polyamines are preferably derived from optionally hydroxyethyl-substituted ethylenediamine or diethylenetriamine. Typical examples are dihydroxyethylene diamine, hydroxyethyldiethylene diamine, hydroxypropyldiethylene triamine and in particular aminoethylethanolamine. N, N-Dimethy 1-1,3-diaminopropane, triethylene tetramine or tetraethylene pentamine are also suitable.
  • the fatty acid glycerides and the polyamines can be used in a molar ratio of 0.5: 2.0 to 2.0: 1, preferably 0.7: 1 to 1.5: 1.
  • the components are heated over a period of 0.5 to 5, preferably 1 to 2 hours to a temperature of 80 to 180, preferably 100 to 120 ° C. until the fatty acid esters have been completely or partially reacted.
  • the mixtures should still contain 0.3 to 2.0%, preferably 0.6 to 1.5% basic nitrogen. If the production of particularly light-colored products is desired, it is advisable to condense in the absence of atmospheric oxygen and, if appropriate, in the presence of a reducing agent, e.g. B. hypophosphorous acid to perform.
  • a reducing agent e.g. B. hypophosphorous acid
  • the unreacted amino groups are neutralized with low molecular weight organic carboxylic acids, hydroxycarboxylic acids or inorganic acids, such as.
  • organic carboxylic acids such as acetic acid, glycolic acid, lactic acid or phosphoric acid
  • the acid used for salt formation can be used in amounts such as are required for 20 to 80, preferably 30 to 60, mol% neutralization.
  • Comparatively hydrophobic, nonionic surfactants which follow the formula (II) are suitable as dispersion accelerators.
  • Typical examples are addition products of an average of 1 mol of ethylene oxide and 2 mol of propylene oxide, 2 mol of ethylene oxide and 4 mol of propylene oxide, 5 mol of ethylene oxide and 1 mol of propylene oxide and 2 to 3 mol of propylene oxide with C 12/18 coconut oil alcohol, C16 / 18 tallow fatty alcohol, C16 / 18- Palm fat alcohol or oleyl alcohol.
  • These addition products are then esterified with fatty acids using known methods.
  • the fatty acids are selected from the group of fatty acids with a total of 8 to 22 carbon atoms. Unbranched, saturated acids are preferably used, for example caproic, capric, lauric, myristic or stearic acid.
  • dispersion accelerators which follow the formula (II) in which R 3 represents an alkyl radical having 12 to 18 carbon atoms and in which the ratio of p: q in the range of 1: 2 have proven useful to 5: 1.
  • R 4 is preferably selected from alkyl radicals having 11 to 17 carbon atoms. Preference is furthermore given to those compounds of the formula (II) in whose synthesis only addition products of propylene oxide are used.
  • the compounds of formula (II) are added to the condensation products after neutralization.
  • the amount used can be 0.5 to 15, preferably 1 to 10,% by weight, based in each case on the condensation products.
  • other known dispersion accelerators such as Monosaccharides of the aldose and ketose type, which are also used from hydrogenation derived polyhydroxy compounds, pentaerythritol, trimethylolpropane, alkylglucosides, sorbitan esters, polysorbates and hydrophilic polymers based on carbohydrates or unsaturated alcohols or carboxylic acids.
  • the fatty acid aminoamides produced according to the invention can be made up, for example, in the form of powders, flakes or pellets and can easily be processed into stable dispersions in water, in particular also in cold water. All you need to do is mix with water and then stir gently.
  • the dispersions obtained are extremely stable and do not tend to separate. They can be used in the textile sector in a variety of ways to treat fibers, yarns or fabrics using the exhaust, immersion centrifugal, padding or spraying methods.
  • Another object of the invention therefore relates to the use of the fatty acid aminoamides which can be prepared according to the invention as a constituent of textile treatment agents.
  • the fatty acid aminoamides can be present in amounts between 10 and 100% by weight, preferably 50 to 95% by weight.
  • the fatty acid aminoamides produced according to the invention When used in detergents, they bring about an improved cleaning action and / or an improvement in the laundry washed therewith.
  • the fatty acid aminoamides produced according to the invention can also be used as constituents of aftertreatment agents for washed textiles, as a result of which the textiles become soft and antistatic.
  • the aftertreatment of the washed textiles can usually be carried out in the last rinsing bath but also during drying in an automatic tumble dryer, either by spraying the laundry with a dispersion of the detergent during drying or by using a flexible, textile fabric that supports the substrate serves.
  • the fatty acid aminoamides produced according to the invention can be used for finishing fibers, yarns or fabrics and for washing textiles and for aftertreatment of washed laundry. Examples
  • the resulting condensation product was mixed with different amounts of an ester, which can be obtained by reacting 0.5 mol of cetyl / oleyl alcohol with 1 mol of propylene oxide (Dehypon OCP 502, Henkel) and then reacting this propylene oxide adduct with 125.0 g of technical stearic acid ( 0.45 mol) at 80 ° C in the presence of 1.2 g of toluenesulfonic acid. The product was then flaked on a chill roll.
  • an ester which can be obtained by reacting 0.5 mol of cetyl / oleyl alcohol with 1 mol of propylene oxide (Dehypon OCP 502, Henkel) and then reacting this propylene oxide adduct with 125.0 g of technical stearic acid ( 0.45 mol) at 80 ° C in the presence of 1.2 g of toluenesulfonic acid.
  • the product was then flaked on a chill roll.
  • the fatty acid aminoamides produced according to the invention are significantly superior to those without a dispersion accelerator in terms of their dispersibility. But also the addition of propoxylated fatty alcohols does not lead to the excellent results that are achieved when using the fatty acid aminoamides produced according to the invention.

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

Abstract

Aminoamides d'acide gras pouvant être obtenus par condensation d'acides gras ou de leurs esters avec des amines polyvalentes, neutralisation partielle des groupes amino n'ayant pas réagi, avec des acides, et addition d'un accélérateur de dispersion de formule (II), dans laquelle R<3> représente un radical alkyle ou alcényle comportant 12 à 22 atomes de carbone et R<4> représente un radical alkyle comportant 7 à 21 atomes de carbone, p vaut 0 ou est compris entre 1 et 5, et q est compris entre 1 et 5.
PCT/EP1998/008046 1997-12-19 1998-12-10 Aminoamides d'acide gras a dispersibilite amelioree WO1999032432A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19756680.4 1997-12-19
DE1997156680 DE19756680A1 (de) 1997-12-19 1997-12-19 Fettsäureamidoamide

Publications (1)

Publication Number Publication Date
WO1999032432A1 true WO1999032432A1 (fr) 1999-07-01

Family

ID=7852615

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1998/008046 WO1999032432A1 (fr) 1997-12-19 1998-12-10 Aminoamides d'acide gras a dispersibilite amelioree

Country Status (2)

Country Link
DE (1) DE19756680A1 (fr)
WO (1) WO1999032432A1 (fr)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0038862A1 (fr) * 1979-08-03 1981-11-04 Albright &amp; Wilson Limited Compositions contenant les sels d'amidoamines et leur utilisation comme agents adoucissants pour matières textiles
EP0164072A2 (fr) * 1984-06-06 1985-12-11 Henkel Kommanditgesellschaft auf Aktien Agent de lavage ayant une force de lavage augmentée
DE4312008A1 (de) * 1993-04-13 1994-10-20 Henkel Kgaa Fettsäureamide

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0038862A1 (fr) * 1979-08-03 1981-11-04 Albright &amp; Wilson Limited Compositions contenant les sels d'amidoamines et leur utilisation comme agents adoucissants pour matières textiles
EP0164072A2 (fr) * 1984-06-06 1985-12-11 Henkel Kommanditgesellschaft auf Aktien Agent de lavage ayant une force de lavage augmentée
DE4312008A1 (de) * 1993-04-13 1994-10-20 Henkel Kgaa Fettsäureamide

Also Published As

Publication number Publication date
DE19756680A1 (de) 1999-06-24

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