EP0075066B1 - Procédé de préparation de composés d'ammonium quaternaires - Google Patents

Procédé de préparation de composés d'ammonium quaternaires Download PDF

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Publication number
EP0075066B1
EP0075066B1 EP82103157A EP82103157A EP0075066B1 EP 0075066 B1 EP0075066 B1 EP 0075066B1 EP 82103157 A EP82103157 A EP 82103157A EP 82103157 A EP82103157 A EP 82103157A EP 0075066 B1 EP0075066 B1 EP 0075066B1
Authority
EP
European Patent Office
Prior art keywords
tertiary amine
reacted
reaction
halohydrin
quaternary ammonium
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
EP82103157A
Other languages
German (de)
English (en)
Other versions
EP0075066A2 (fr
EP0075066A3 (en
Inventor
Horst Dr. Rutzen
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
Priority to AT82103157T priority Critical patent/ATE24890T1/de
Publication of EP0075066A2 publication Critical patent/EP0075066A2/fr
Publication of EP0075066A3 publication Critical patent/EP0075066A3/de
Application granted granted Critical
Publication of EP0075066B1 publication Critical patent/EP0075066B1/fr
Expired legal-status Critical Current

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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
    • C11D1/38—Cationic compounds
    • C11D1/62—Quaternary ammonium compounds
    • 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
    • D06M13/385—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 containing epoxy groups
    • 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
    • D06M13/46—Compounds containing quaternary nitrogen atoms
    • D06M13/463—Compounds containing quaternary nitrogen atoms derived from monoamines
    • 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
    • D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
    • 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
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • 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
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/50—Modified hand or grip properties; Softening compositions

Definitions

  • quaternary ammonium compounds are usually based on a tertiary amine, which is alkylated at the quaternary stage.
  • the alkylating agent it is customary to allow esters of strong mineral acids, in particular alkyl halides, sulfuric or sulfonic acid esters, to act on tertiary amines; other esters are occasionally used.
  • Another known possibility for the alkylation of tertiary amines is the reaction of alkylene oxides with tertiary amines in the presence of water.
  • Quaternary ammonium compounds with one or more long aliphatic radicals or one long aliphatic and one aromatic radical have antimicrobial or fabric softening and antistatic properties and are widely used.
  • Compounds of this type are obtained by either alkylating tertiary amines with long alphatic radicals and / or aromatic radicals or by carrying out the alkylation with alkylating agents which in turn contain long aliphatic or aromatic radicals, of course also long aliphatic or both in the tertiary amine and in the alkylating agent aromatic residues may be present.
  • quaternary ammonium compounds can be prepared in a simple manner with high yield by reacting a tertiary amine with a vicinal halohydrin.
  • the process is characterized in that a tertiary amine is reacted with a halohydrin having at least 6 carbon atoms in the heat at normal pressure, if appropriate in the presence of water, the reaction mixture being free from organic solvents.
  • halohydrins The quaternization of tertiary amines with halohydrins is known, for example from Japanese patent application 16 523/65 ,; where the reaction of trimethylamine with ethylene chlorohydrin to choline chloride is described.
  • FR-A-999 703 discloses the production of bisquaternary ammonium compounds by reacting tertiary amine with the dihalohydrin of butatiene.
  • halohydrins for quaternization known from the literature is limited to short-chain, readily water-soluble halohydrins, which are mostly used in solvent-containing reaction batches.
  • Halohydrins which are particularly suitable for the process according to the invention are 1,2-halohydrins having 6 to 28 carbon atoms, ie. H. those halohydrins which carry the hydroxyl group and the halogen atom on the two outermost carbon atoms of the carbon chain.
  • the reaction of the halohydrins with tertiary amine is preferably carried out in a molar ratio of 1: 1, but a slight excess of one or the other component is also possible and useful in some cases.
  • 1,2-halohydrins are easily accessible compounds, they can be obtained, for example, by reacting 1,2-epoxyalkanes with hydrogen halide. In this reaction too, the reactants are preferably reacted in a molar ratio of 1: 1.
  • the halohydrins are obtained in a short reaction time if the hydrogen halides are used in commercially available, aqueous, concentrated form, for example HCl: 37%, HBr: 48 or 63%, HJ: 57 or 67%.
  • the reaction temperature is advantageously about 30 to 100 ° C. Such a temperature is generally established without the addition of heat from the outside due to the heat of reaction.
  • the reaction mixture is two-phase when using aqueous hydrogen halide solutions; nevertheless, the reaction proceeds practically completely within about an hour. If aqueous hydrogen halide solutions are used in a lower concentration, the reaction generally takes a little longer.
  • the reaction product obtained in the described halohydrin formation is usually not uniform; It consists of an isomer mixture of 1-halogen-2-hydroxy and 1-hydroxy-2-haloalkane. It is not necessary to separate the isomers when carrying out the process according to the invention.
  • 1,2-Epoxyalkanes suitable for the preparation of 1 2-halohydrins are obtained in a known manner from the corresponding 1,2-monoolefins or olefin mixtures, for example by polymerizing ethylene with organic aluminum compounds as catalysts or by thermal cracking of paraffin hydrocarbons be preserved.
  • preferred epoxyalkanes are the compounds 1,2-epoxyhexane, 1,2-epoxyoctane, 1,2-epoxydecane, 1,2-epoxydodecane, 1,2-epoxytetradecane, 1,2-epoxyhexadecane, 1,2-epoxycctadecane.
  • epoxy mixtures such as C 12/14 -1,2-epoxy with about 70 percent by weight C 12 - and about 30 percent by weight C 14 -epoxyalkane or C 16/18 -1,2-epoxy with about 40 percent by weight C, 6 - and about 60 percent by weight C 18 epoxyalkane.
  • di-epoxyalkanes with 8 to 20 carbon atoms and two terminal epoxy groups such as, for example, 1,2-7,8-diepoxyoctane, 1,2-9,10-diepoxydecane and similar compounds.
  • Mono- or di-glycidyl ethers such as hexadecyl monoglycidyl ether and 1,4-butanediol diglycidyl ether are also preferred epoxy compounds terminal epoxy groups.
  • the preferred epoxy compounds correspond to either general formula 1 in which R 1 is a linear or branched aliphatic hydrocarbon group having 1 to 21 carbon atoms or a group of the general formula 11 with n is 4 to 16, or they correspond to a glycidyl ether of the general formula III in which m has a value of 1 to 10 and R 2 is hydrogen or an aliphatic hydrocarbon group having 1 to 24 carbon atoms or a group of the general formula IV means.
  • 1,2-Halohydrins which are particularly suitable for carrying out the process according to the invention are 1,2-halohydrins having 10 to 20, preferably 12 to 16 carbon atoms, for example 1 (2) -chloro-2 (1) -hydroxy-dodecane, 1 (2nd ) -Brom-2 (1) -hydroxy-hexadecane, 1 (2) -chloro-2 (1) -hy-droxy-hexadecane, 1 (2) -iodine-2 (1) -hydroxy-dodecane, the name being 1 (2) or 2 (1) - is intended to mean both the pure isomers and their mixture.
  • Tertiary amines which are suitable as reactants for the halohydrins are, in particular, more basic amines such as, for example, trimethylamine, dimethylbenzylamine, triethylamine, tributylamine, dimethylhexylamine, dimethyllaurylamine, dimethylethanolamine, dimethylpropanolamine, N- ⁇ -hydroxydecyl-N- ⁇ -hydroxyamine-N-methyl-N-methyl-N N-ß-hydroxyhexadecyl-N-ß-hydroxyethylamine, methyldiethanolamine, dimethylaminopropanediol, tertiary diamines such as tetramethylene diamine or tetramethylpropylenediamine-1,3, also pyridine, picoline, pipecoline, N-methylpiperidine, N-methylpyrrolidine, quinuclidine.
  • more basic amines such as, for example, trimethylamine, dimethylbenzylamine, trieth
  • the process according to the invention is expediently carried out at elevated temperature, that is to say at 40 to 100 ° C., preferably at 65 to 95 ° C.
  • elevated temperature that is to say at 40 to 100 ° C., preferably at 65 to 95 ° C.
  • addition of 0.5 to 10% by weight, based on the end product, of a quaternary ammonium salt accelerates the reaction in many cases.
  • the new process is distinguished from the processes of the prior art in that it is carried out without using excess pressure at relatively low reaction temperatures and in shorter reaction times and delivers end products in high purity with high yields.
  • Reaction products produced according to the invention with only one long-chain aliphatic or one aromatic radical or two alkyl or alkenyl radicals with less than about 10 carbon atoms and the rest of the short-chain alkyl radicals have antimicrobial properties.
  • These compounds are obtained either by reacting halohydrins with, for example, 10 to 20 carbon atoms with tertiary amines with only short alkyl or hydroxylalkyl or aralkyl radicals, or by starting from a halohydrin with about 6 to 10 carbon atoms, which is reacted with a tertiary Amine with a C 10 to C 20 alkyl or alkenyl radical which is derived from fatty acids.
  • the reaction products show increasingly pronounced fabric softening and antistatic properties. Depending on the chemical constitution of the compounds, smooth transitions can be observed.
  • Textile softening compounds with a C 10 to C 20 alkyl, hydroxylalkyl or alkenyl radical and a C 10 to C 20 hydroxyalkyl radical and the rest of the short radicals are correspondingly obtained by using a tertiary amine with a C 10 - up to C 20 alkyl or hydroxyalyl or alkenyl radical with a C 10 - to C 2O halohydrin.
  • antimicrobially active compounds and textile care compounds is therefore a further subject of the invention as is the use of the process products as textile softeners or antistatic agents or as antimicrobials.
  • They are used as textile softeners, for example, in liquid laundry aftertreatment which, in addition to the active substance produced according to the invention, additionally contain at least one further compound from the group consisting of carriers, solvents, diluents, emulsifiers, colorants, fragrances, preservatives, viscosity regulators, opacifiers and possibly other customary additives.
  • the rest are viscosity control agents, opacifiers, optionally acidic compounds and other customary additives.
  • the process products are added to detergents of appropriate composition, which contain at least one detergent-active compound, they can have a softening effect.
  • Such detergents are preferably based on formulations with nonionic surfactants. If the process products are applied together with customary auxiliaries and additives to textile fabrics as carriers, these can also be used as tumbling aids.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biochemistry (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • General Chemical & Material Sciences (AREA)
  • Microbiology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Detergent Compositions (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Cephalosporin Compounds (AREA)

Claims (9)

1. Procedé de fabrication de composés d'ammonium quaternaires à partir d'une amine tertiaire et d'une halohydrine, caractérisé en ce qu'on fait réagir une amine tertiaire avec une halohydrine vicinale ayant au moins 6 atomes de carbone, à chaud et sous la pression normale, éventuellement en présence d'eau, la charge de réaction étant exempte de solvants organiques.
2. Procédé selon la revendication 1, caractérisé en ce qu'on fait réagir des 1,2-halohydrines ayant 6 à 28 atomes de carbone avec une amine tertiaire, de préférence dans le rapport molaire de 1:1.
3. Procédé selon les revendications 1 et 2, caractérisé en ce qu'on fait réagir des halohydrines, obtenues par réaction de 1,2-époxydes avec un hydracide hatogéné, avec une amine tertiaire.
4. Procédé selon les revendications 1 à 3, caractérisé en ce qu'on exécute la réaction avec l'amine tertiaire à 40 -100° C, de préférence à 65 - 95° C.
5. Procédé selon les revendications 1 à 4, caractérisé en ce qu'on fait réagir une 1,2-halohydrine ayant 10 à 20, de préférence 12 à 16 atomes de carbone, avec une amine tertiaire.
6. Procédé selon les revendications 1 à 5, caractérisé en ce qu'on fait réagir une amine tertiaire avec radicaux alcoyle, hydroxyalcoyle à chaine courte ou aryle, avec une halohydrine ayant 10 à 20 atomes de carbone.
7. Procédé selon les revendications 1 à 5, caractérisé en ce qu'on fait réagir une amine tertiaire ayant un radical alcoyle ou alcényle en Clo à C20 avec une halohydrine ayant 6 à 10 atomes de carbone.
8. Procédé selon les revendications 1 à 5, caractérisé en ce qu'on fait réagir une amine tertiaire ayant un radical alcoyle, hydroxyalcoyle ou alcényle en C10 à C20 avec une halohydrine ayant 10 à 20 atomes de carbone.
9. Procédé selon les revendications 1 à 8, caractérisé en ce qu'on exécute la réaction en présence de 0,5 à 10; en poids d'un sel d'ammonium quaternaire.
EP82103157A 1981-09-15 1982-04-15 Procédé de préparation de composés d'ammonium quaternaires Expired EP0075066B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT82103157T ATE24890T1 (de) 1981-09-15 1982-04-15 Verfahren zur herstellung von quartaeren ammoniumverbindungen.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19813136628 DE3136628A1 (de) 1981-09-15 1981-09-15 "verfahren zur herstellung von quartaeren ammoniumverbindungen"
DE3136628 1981-09-15

Publications (3)

Publication Number Publication Date
EP0075066A2 EP0075066A2 (fr) 1983-03-30
EP0075066A3 EP0075066A3 (en) 1984-09-05
EP0075066B1 true EP0075066B1 (fr) 1987-01-14

Family

ID=6141734

Family Applications (1)

Application Number Title Priority Date Filing Date
EP82103157A Expired EP0075066B1 (fr) 1981-09-15 1982-04-15 Procédé de préparation de composés d'ammonium quaternaires

Country Status (7)

Country Link
US (1) US4480126A (fr)
EP (1) EP0075066B1 (fr)
JP (1) JPS5846043A (fr)
AT (1) ATE24890T1 (fr)
BR (1) BR8202351A (fr)
DE (2) DE3136628A1 (fr)
ZA (1) ZA822758B (fr)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3442175A1 (de) * 1984-11-17 1986-05-28 Henkel KGaA, 4000 Düsseldorf Konditionierende haarpflegemittel
US4764306A (en) * 1984-12-03 1988-08-16 Ppg Industries, Inc. Process for the manufacture of bis-quaternary ammonium compounds
US4602110A (en) * 1985-05-15 1986-07-22 The Dow Chemical Company Method of purifying 3-chloro-2-hydroxypropyl trialkylammonium chloride
US4883917A (en) * 1985-10-01 1989-11-28 Ethyl Corporation Quaternary ammonium compounds
US4812263A (en) * 1986-08-22 1989-03-14 Ppg Industries, Inc. Bis-quaternary ammonium compounds
US5082968A (en) * 1990-11-01 1992-01-21 General Electric Company Method of preparing hexaalkylguanidinium salts
EP2054371B1 (fr) * 2006-08-15 2011-03-09 Dow Global Technologies Inc. Procédé de préparation d'halogénures d'alkyle ammonium quaternaire
US7662970B2 (en) * 2006-11-17 2010-02-16 Baker Hughes Incorporated Oxazolidinium compounds and use as hydrate inhibitors
US8575358B2 (en) 2006-11-17 2013-11-05 Baker Hughes Incorporated Oxazolidinium compounds
FR2967897B1 (fr) * 2010-11-25 2013-05-17 Oreal Composition pour traiter les fibres keratiniques comprenant un tensioactif cationique comprenant une chaine grasse hydroxylee
WO2012069639A2 (fr) * 2010-11-25 2012-05-31 L'oreal Composition pour traiter des fibres de kératine comprenant un tensioactif cationique comprenant une chaîne hydroxylée
WO2022038631A1 (fr) * 2020-08-18 2022-02-24 Council Of Scientific And Industrial Research Sels de fluorure d'ammonium quaternaire pour réactions de fluoration

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2142140A (en) * 1932-08-12 1939-01-03 Merck & Co Inc Salts of beta-alkylated-choline-alkyl-ethers and process for their production
US2192925A (en) * 1935-12-04 1940-03-12 Merck & Co Inc beta-alkylcholine salts and their acyl esters
US2655541A (en) * 1948-10-14 1953-10-13 Hopff Heinrich Preparation of choline chloride
FR999703A (fr) * 1949-04-30 1952-02-04 Basf Ag Procédé pour l'obtention de composés d'ammonium bis-quaternaires
NL127406C (fr) * 1964-11-04
DE1619081B2 (de) * 1966-12-21 1977-03-03 Henkel & Cie GmbH, 4000 Düsseldorf Avivagemittel fuer textilien

Also Published As

Publication number Publication date
JPS5846043A (ja) 1983-03-17
US4480126A (en) 1984-10-30
JPH0237341B2 (fr) 1990-08-23
DE3275085D1 (en) 1987-02-19
BR8202351A (pt) 1983-11-16
ZA822758B (en) 1983-04-27
DE3136628A1 (de) 1983-03-31
EP0075066A2 (fr) 1983-03-30
ATE24890T1 (de) 1987-01-15
EP0075066A3 (en) 1984-09-05

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