GB670326A - Improvements relating to cationic surface active agents - Google Patents

Improvements relating to cationic surface active agents

Info

Publication number
GB670326A
GB670326A GB23521/48A GB2352148A GB670326A GB 670326 A GB670326 A GB 670326A GB 23521/48 A GB23521/48 A GB 23521/48A GB 2352148 A GB2352148 A GB 2352148A GB 670326 A GB670326 A GB 670326A
Authority
GB
United Kingdom
Prior art keywords
acids
mixture
carbon dioxide
acid
dissolved
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
GB23521/48A
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.)
Colgate Palmolive Co
Original Assignee
Colgate Palmolive Co
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 Colgate Palmolive Co filed Critical Colgate Palmolive Co
Publication of GB670326A publication Critical patent/GB670326A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38Cationic compounds
    • C11D1/52Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/528Carboxylic amides (R1-CO-NR2R3), where at least one of the chains R1, R2 or R3 is interrupted by a functional group, e.g. a -NH-, -NR-, -CO-, or -CON- group

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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fats And Perfumes (AREA)

Abstract

Cationic surface-active agents of the aminoalkylene monoamide type are obtained by a process which includes the step of contacting with carbon dioxide a liquid medium containing an amino alkylene monoamide and an alkylene diamide or an amine polyalkylene polyamide so as to precipitate a carbon dioxide addition compound of the said monoamide and separating this addition compound from the residual liquid. The mixture may be dissolved in an organic solvent prior to the CO2 treatment and any unreacted alkylene polyamine which has been used in the production of the amide mixture to be treated may be separated prior to the CO2 treatment. The addition compound can be split into the desired amino alkylene monoamide and carbon dioxide by treating it with a mineral acid such as hydrochloric acid, or by heating. The treated amide mixture may be obtained by reacting an organic acid or its esters with short-chain alcohols of 1 to 3 carbon atoms with an alkylene polyamine. Specified alkylene polyamines are ethylene diamine, diethylene triamine, triethylene tetramine, tetraethylene pentamine, di-(hexamethylene) triamine, propylene diamine, dipropylene triamine, and butylene diamine. The organic acids which may be employed include aliphatic acids and acids containing carbocyclic or heterocyclic ring systems such as benzoic acid, naphthenic acid and pyridine 2-carboxylic acid. The acids may be saturated or unsaturated and both the acids and the alcohols used to form the esters that may be used instead of the acids may contain substituents such as halogen atoms or hydroxyl groups. It is preferred to use fatty acids of 6 to 24 carbon atoms. Specified aliphatic acids are caprylic, isocaprylic, nonylic, capric, caproic, undecylenic, lauric, myristic, palmitic, stearic, hydroxystearic, oleic, ricinoleic, alpha amino capric, undecylenic, linoleic, linolenic, and erucic acids and various mixtures of these acids. Coconut oil fatty acids containing from 12 to 16 carbon atoms and mixed tallow fatty acids are also suitable. Instead of the acids the glycol (or polyglycol) mono- or diesters, the glycerol mono-, di- or tri-esters and the methyl, ethyl or propyl esters may be used. In the production of the amide mixture it is preferred to use an excess of the alkylene polyamine and temperatures of 100 DEG to 250 DEG C. may be employed, the reaction temperature being preferably at or approaching the boiling-point of the lowest boiling component of the reaction mixture under the prevailing pressure which may be atmospheric, subatmospheric or superatmospheric pressure. The treatment with CO2 to form the addition compound may also be carried out over a wide range of pressure and the CO2 should be used in substantial stoichiometric excess. The CO2 in gaseous form may be bubbled through the mixture dissolved in a suitable solvent, or the mixture dissolved in a solvent with or without agitation may be contacted with CO2 in liquid or solid form. Specified solvents are methanol, acetone, dioxane, ethanol, diethyl ether, benzene and butanol. Mixtures of solvents may be employed, e.g. a 1 : 1 mixture of methanol with benzene or ether may be used. If desired, a portion of the diamide may first be separated from the mixture to be treated by taking up the residue after distillation in warm or hot solvent and then cooling to precipitate the diamide and separating the latter by filtration. In examples: (1) to (4) the amide mixture obtained by reacting diethylene triamine with (1) the methyl esters of coconut oil fatty acids; (2) glacial acetic acid; (3) the mixed methyl esters of tallow fatty acid; and (4) coconut fatty acids, is dissolved in methanol (examples 1, 3 and 4) or chloroform (example 2) and the solution then saturated with carbon dioxide to form the addition compound. In (1) the addition product is dissolved in dilute hydrochloric acid to pH 7 and the resulting solution is stated to have excellent deterging and foaming properties, also on heating the addition product in air the product loses CO2 to form a material which dissolves in dilute hydrochloric acid to pH 7 to give a solution with good deterging and foaming properties; (5) triethylene tetramine is heated with methyl stearate and the excess amine removed by vacuum evaporation. The residual mixture is dissolved in warm methanol and cooled to deposit some of the diamide which is filtered off. The filtrate is then saturated with carbon dioxide to form the addition which yields the free monoamide on heating; (6) to (8) ethylene diamine is heated with the mixed methyl esters of coconut fatty acids, coconut oil, and methyl laurate, respectively, and the mixture formed is treated with carbon dioxide as in (5). In (8) the free amide is obtained by heating to remove the carbon dioxide. U.S.A. Specifications 1,947,951 and 2,387,201 are referred to.
GB23521/48A 1947-09-08 1948-09-07 Improvements relating to cationic surface active agents Expired GB670326A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US670326XA 1947-09-08 1947-09-08

Publications (1)

Publication Number Publication Date
GB670326A true GB670326A (en) 1952-04-16

Family

ID=22073288

Family Applications (1)

Application Number Title Priority Date Filing Date
GB23521/48A Expired GB670326A (en) 1947-09-08 1948-09-07 Improvements relating to cationic surface active agents

Country Status (1)

Country Link
GB (1) GB670326A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116397232A (en) * 2023-04-19 2023-07-07 江苏太湖新材料控股有限公司 Water-soluble corrosion inhibitor and synthesis method thereof

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116397232A (en) * 2023-04-19 2023-07-07 江苏太湖新材料控股有限公司 Water-soluble corrosion inhibitor and synthesis method thereof
CN116397232B (en) * 2023-04-19 2023-10-27 江苏太湖新材料控股有限公司 Water-soluble corrosion inhibitor and synthesis method thereof

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