GB613835A - Fatty acid esters having amphoteric properties - Google Patents
Fatty acid esters having amphoteric propertiesInfo
- Publication number
- GB613835A GB613835A GB23653/45A GB2365345A GB613835A GB 613835 A GB613835 A GB 613835A GB 23653/45 A GB23653/45 A GB 23653/45A GB 2365345 A GB2365345 A GB 2365345A GB 613835 A GB613835 A GB 613835A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amino
- acid
- methyl
- propanediol
- esters
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/003—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with alcohols
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/02—Water
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/26—Amines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
- C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
- C10M2227/06—Organic compounds derived from inorganic acids or metal salts
- C10M2227/061—Esters derived from boron
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/46—Textile oils
Landscapes
- Chemical & Material Sciences (AREA)
- General 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)
- Cosmetics (AREA)
Abstract
Mono-esters obtained by heating a fatty acid containing at least six carbon atoms with an aliphatic amino alcohol having the formula H2N.C(R1)(R2)CH(R3)(OH) in which R1, R2 and R3 may be H, alkyl or alkylol and the sum of the carbon atoms in R1 and R2 is at least one (see Group IV) may be used as self-emulsifying oils and waxes and for emulsification of oils and waxes or as synthetic waxes to replace natural waxes in polishes, creams or cosmetics. A solution of the mono-ester obtained from palmitic acid and 2-amino 1-butanol in a low-viscosity mineral oil sets to a thick vaseline-like grease. When the ester products contain a free hydroxyl group or a double bond they may be sulphated, preferably by treatment with concentrated sulphuric acid to yield sulphated esters which may be used in insecticide emulsions, paints and cosmetics. Reference has been directed by the Comptroller to Specifications 414,403 and 538,859.ALSO:Mono-esters containing an unsubstituted primary amino group are prepared by heating a fatty acid containing at least six carbon atoms with an aliphatic amino alcohol having the formula H2N.C(R1)R2).CH(R3)(OH) in which R1, R2 and R3 may be H, alkyl or alkylol and the sum of the carbon atoms in R1 and R2 is at least one, at dehydrating temperatures until substantially one molecular proportion of water is removed. Specified fatty acids are caproic, caprylic, capric, lauric, myristic, palmitic, oleic, stearic, ricinoleic, linoleic, arachidic, behenic, lignoceric, palmitoleic, linolenic, elaeostearic and clupandonic acids or mixtures thereof, coconut fatty acids and the acids obtained from cotton seed, corn, peanut and sunflower. Specified amino alcohols are 2-amino-2-methyl (or 2-ethyl) 1,3-propanediol and the propyl and isopropyl compounds, tris-(hydroxy-methyl)-amino methane, 2-amino-2-methyl-1-propanol and the ethyl, propyl and isopropyl substituted compounds, 2-amino-1-propanol, -isopropanol and -1-butanol, 2-amino-1,3-propanediol, 3-amino-3-methyl-2-butanol, 4-amino-5-methyl-3-hexanol and 5-amino-4-octanol. Catalysts such as acids, acid salts, e.g. sodium bisulphate, or powdered metals such as tin and copper may be used. The composition of the reaction mixture is gauged by the reduction of its acid number. When the ester products contain a free hydroxyl group or a double bond derived from an unsaturated fatty acid radical, they may be sulphated, preferably by treatment with concentrated sulphuric acid under mild sulphation conditions to yield a sulphated ester. Boric acid may be added to the sulphation mass to yield boro-sulphates or acetic acid to produce sulphoacetic compounds. The sulphated esters are amphoteric and have combined cation and anion activity. Examples describe the production of mono-esters from coconut fatty acids, stearic acid, oleic acid, ricinoleic acid, palmitic acid, myristic acid, caproic acid and lauric acid and 2-amino-2-methyl-1,3-propanediol, 2-amino-2-ethyl-1,3-propanediol, 2-amino-2-methyl - 1 - propanol, 2 - amino - 1 - butanol and tris-(hydroxy-methyl)-amino methane. The products are variously light coloured oils and waxes. The mono-ester of coconut fatty acid with 2 - amino - 2 - methyl - 1,3 - propanediol, of stearic acid with tris-(hydroxy-methyl)-amino methane, and of oleic acid with 2-amino-2-ethyl-1,3-propanediol are added, respectively, to 100 per cent sulphuric acid at about 35 DEG C., and after cooling a solution of sodium hydroxide is added until neutral. The products are useful as dispersing and wetting agents, for softening textiles, for level dyeing with basic dyes and to increase the fastness of direct dyeing. The mono-esters may also be used for flocculating acidic compounds, emulsification of oils and waxes or as synthetic waxes in polishes and creams, and the sulphated esters may also be used in insecticide emulsions, paints and cosmetics. The amino alcohols used as starting materials may be prepared by condensing a nitro-paraffin with an aldehyde to form a nitrohydroxy compound and then reducing the latter, thus 2-amino-2-methyl-1-propanol may be obtained by reacting 2-nitropropane with formaldehyde to give 2-nitro-2-methyl-1-propanol and reducing the latter. Reference has been directed by the Comptroller to Specifications 414,403 and 538,859.ALSO:Mono-esters containing an unsubstituted primary amino group are prepated by heating a fatty acid containing at least six carbon atoms with an aliphatic amino alcohol having the formula: H2N.C.(R1)(R2).CH(R3)(OH) in which R1, R2 and R3 may be H, alkyl or alkylol and the sum of the carbon atoms in R1 and R2 is at least one, at dehydrating temperatures until substantially one molecular proportion of water is removed. Specified fatty acids are caproic, caprylic, capric, lauric, myristic, palmitic, oleic, stearic, ricinoleic, linoleic, arachidic, behenic, lignoceric, palmitoleic, linolenic, elaeostearic and clupandonic acids or mixtures thereof, cocoanut fatty acids and the acids obtained from cotton seed, corn, peanut and sun flower. Specified amino alcohols are 2 - amino - 2 - methyl (or 2-ethyl) 1,3-propanediol and the propyl and isopropyl compounds, Tris(hydroxy-methyl) amino methane, 2-amino 2-methyl 1-propanol and the ethyl, propyl and isopropyl substituted compounds, 2-amino-1-propanol, -isopropanol and -1-butanol, 2-amino-1-3-propanediol, 3-amino 3-methyl 2-butanol, 4-amino 5-methyl 3-hexanol and 5-amino-4-octanol. Catalysts such as acids, acid salts, e.g. sodium bisulphate, or powdered metals such as tin and copper may be used. The composition of the reaction mixture is gauged by the reduction of its acid number. When the ester products contain a free hydroxyl group or a double bond derived from an unsaturated fatty acid radical they may be sulphated, preferably by treatment with concentrated sulphuric acid under mild sulphation conditions to yield a sulphated ester. Boric acid may be added to the sulphation mass to yield boro sulphates or acetic acid to produce sulphoacetic compounds. The sulphated esters are amphoteric and have combined cation and anion activity. Examples describe the production of mono-esters from cocoanut fatty acids, stearic acid, oleic acid ricinoleic acid, palmitic acid, myristic acid, caproic acid and lauric acid and 2-amino 2-methyl 1-3-propanediol, 2-amino 2-ethyl 1-3-propanediol, 2-amino 2-methyl 1-propanol, 2-amino 1-butanol and Tris (hydroxy-methyl) amino methane. The products are variously light coloured oils and waxes. The mono-ester of cocoanut fatty acid with 2-amino 2-methyl 1,3-propanediol, of stearic acid with Tris (hydroxy methyl) amino methane, and of oleic acid with 2-amino 2-ethyl 1-3-propanediol are added, respectively, to 100 per cent sulphuric acid at about 35 DEG C. and after cooling a solution of sodium hydroxide is added until neutral. The products are useful as dispersing and wetting agents, for softening textiles, for level dying with basic dyes and to increase the fastness of direct dyeing. The mono esters may also be used for flocculating acidic compounds, emulsification of oils and waxes or as synthetic waxes in polishes and creams, and the sulphated esters may also be used in insecticide emulsions, paints and cosmetics. The amino alcohols used as starting materials may be prepared by condensing a nitro paraffin with an aldehyde to form a nitro hydroxy compound and then reducing the latter, thus 2-amino, 2-methyl 1-propanol may be obtained by reacting 2-nitro propane with formaldehyde to give 2-nitro-2-methyl-1-propanol and reducing the latter. Reference has been directed by the Comptroller to Specifications 414,403 and 538,859.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB23653/45A GB613835A (en) | 1945-09-13 | 1945-09-13 | Fatty acid esters having amphoteric properties |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB23653/45A GB613835A (en) | 1945-09-13 | 1945-09-13 | Fatty acid esters having amphoteric properties |
Publications (1)
Publication Number | Publication Date |
---|---|
GB613835A true GB613835A (en) | 1948-12-03 |
Family
ID=10199119
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB23653/45A Expired GB613835A (en) | 1945-09-13 | 1945-09-13 | Fatty acid esters having amphoteric properties |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB613835A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2425424A1 (en) * | 1978-05-12 | 1979-12-07 | Nattermann A & Cie | SYNTHETIC COMPOUNDS WITH ANALOGUE STRUCTURE TO THAT OF NATURAL GLYCERIDES, THEIR PREPARATION AND THEIR THERAPEUTIC USES |
US10098098B2 (en) | 2010-11-30 | 2018-10-09 | Ecolab Usa Inc. | Mixed fatty acid soap/fatty acid insecticidal, cleaning, and antimicrobial compositions |
-
1945
- 1945-09-13 GB GB23653/45A patent/GB613835A/en not_active Expired
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2425424A1 (en) * | 1978-05-12 | 1979-12-07 | Nattermann A & Cie | SYNTHETIC COMPOUNDS WITH ANALOGUE STRUCTURE TO THAT OF NATURAL GLYCERIDES, THEIR PREPARATION AND THEIR THERAPEUTIC USES |
US10098098B2 (en) | 2010-11-30 | 2018-10-09 | Ecolab Usa Inc. | Mixed fatty acid soap/fatty acid insecticidal, cleaning, and antimicrobial compositions |
US11533911B2 (en) | 2010-11-30 | 2022-12-27 | Ecolab Usa Inc. | Mixed fatty acid soap/fatty acid based insecticidal, cleaning, and antimicrobial compositions |
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