GB708000A - Improvements relating to liquid synthetic detergent compositions - Google Patents
Improvements relating to liquid synthetic detergent compositionsInfo
- Publication number
- GB708000A GB708000A GB9063/51A GB906351A GB708000A GB 708000 A GB708000 A GB 708000A GB 9063/51 A GB9063/51 A GB 9063/51A GB 906351 A GB906351 A GB 906351A GB 708000 A GB708000 A GB 708000A
- Authority
- GB
- United Kingdom
- Prior art keywords
- bis
- dialkylolamide
- carbon atoms
- detergent
- per cent
- 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
- 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
- C11D1/65—Mixtures of anionic with cationic compounds
- C11D1/655—Mixtures of sulfonated products with alkylolamides of carboxylic acids
-
- 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
- C11D1/65—Mixtures of anionic with cationic compounds
- C11D1/652—Mixtures of anionic compounds with carboxylic amides or alkylol amides
-
- 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
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/43—Solvents
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
- Y10S516/07—Organic amine, amide, or n-base containing
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)
- Detergent Compositions (AREA)
- Cosmetics (AREA)
Abstract
Dialkylolamides of fatty acids which contain 10 to 14 carbon atoms are prepared by condensing fatty acylating compounds such as the acid, its ester, acid anhydride or acyl halide with a dialkylolamine, the latter reactant being preferably in excess. Suitable molar ratios of acylating compound to dialkylolamine lie bebetween 1 : 1 and 1 : 10, preferably about 1 : 2 to about 1 : 3, the reaction being carried out between about 100 DEG C. and about 200 DEG C. A complex mixture of products is formed, and in order to obtain an equilibrium mixture containing an effective proportion of the dialkylolamide the product may be cooled relatively slowly or held at a slightly elevated temperature for a period of time. A typical reaction mixture from lauric acid (90 per cent pure) and diethanolamine may contain 65 per cent diethanolamide, 10 per cent diethanolamine soap and 25 per cent diethanol-piperazine and other substances including water. The fatty acylating substances may be derived from pure, impure or mixtures of capric, lauric, and myristic acids. Mixtures of these acids derived from natural sources and containing acids of higher and lower molecular weight may also be used, such as "topped" coconut oil fatty acids. Suitable dialkylolamines for the reaction include, besides diethanolamine, N,N - bis - (2,3 - dihydroxypropyl) - amine, dipropanolamine, N,N - bis - (2-hydroxylpropyl) - amine and dibutanolamine. Dialkylolamides specified include N,N-bis-(2-hydroxyethyl) - lauramide, N,N - bis - (2-hydroxyethyl) - capramide, N,N - bis - (2-hydroxyethyl) - myristamide, N,N - bis - (2,3-dihydroxypropyl) - lauramide, N,N - bis - (2,3-dihydroxypropyl) - myristamide, N,N - bis - (3-hydroxypropyl) - lauramide, N,N - bis - (3-hydroxypropyl) - capramide, N,N - bis - (2-hydroxypropyl) - myristamide, and N,N - bis-(4-hydroxybutyl)-lauramide. The dialkylolamides may be incorporated in detergent compositions (see Group III).ALSO:A liquid detergent composition comprises a water-soluble anionic sulphated or sulphonated detergent containing an aliphatic chain of at least 8 carbon atoms, a dialkylolamide of a fatty acid which contains 10 to 14 carbon atoms and a solvent for the detergent and the dialkylolamide. Suitable solvents include the low molecular weight hydroxyl containing solvents, particularly water, saturated aliphatic alcohols or aqueous saturated aliphatic alcohols. Specified alcohols include ethyl alcohol, n-propyl alcohol, isopropyl alcohol, n-butyl alcohol, ethylene glycol, propylene glycol, glycerol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, and diethylene glycol monobutyl ether. Dioxan may also be used. It is preferred to use water, mono- or di-hydric alcohols containing 2 to 4 carbon atoms in the molecule, lower (i.e. C1-C5) alkyl ethers of these dihydric alcohols and mixtures of these solvents The dialkylolamide may be of general formula RCO-NR1R11, where RCO represents a fatty acyl radical containing 10 to 14 carbon atoms and R1 and R11 are the same or different hydroxyalkyl groups of 1-5 carbon atoms. These hydroxyalkyl groups may be mono-or polyhydroxy in character. Specific dialkylolamide additives include N,N - bis - (2 - hydroxyethyl) lauramide, H,N-bis-(2-hydroxyethyl) capramide, N1N-bis-(2-hyroxyethyl) myristamide, N,N-bis-(2, 3-dihydroxypropyl) lauramide, N,N-bis-(2, 3-dihydroxypropyl) myristamide, N,N-bis-(3-hydroxypropyl) lauramide, N,N-bis- (3-hydroxypropyl) capramide, N,N-bis-(2-hydroxypropyl) myristamide and N,N - bis - (4-hydroxybutyl) lauramide. Diethanolamide compounds are preferred. (For preparation of these dialkylolamides see Group IV (b)). Impurities such as soap, free alkylolamine and piperazine type derivatives may result as by-products during the manufacture of the dialkylolamides, and provided that these impurities are not present in such amounts as to interfere with the detergent action of the final composition, the dialkylolamide product containing them may be used without further purification. The sulphated or sulphonated detersive compound may be an aliphatic acylcontaining compound containing 8 to 22 carbon atoms in the acyl group such as the sulphated or sulphonated aliphatic carboxylic esters containing 10 to 26 carbon atoms in the molecule. Other specified detergents include the sulphuric acid esters of polyhydric alcohols incompletely esterified with higher (i.e. at least 8 carbon atoms) fatty acids such as coconut oil monoglyceride monosulphate or tallow diglyceride monosulphate; pure or mixed higher alkyl sulphates such as lauryl sulphate, cetyl sulphate and fatty alcohol sulphates derived from reduced coconut oil fatty acids; the hydroxy sulphonated higher fatty acid esters such as the higher fatty acid esters of 2, 3-dihydroxypropane sulphonic acid; the higher fatty acid esters of lower alkylol sulphonic acids such as the oleic acid ester of isethionic acid; the higher fatty acid ethanolamide sulphates; and the higher fatty acid amides of amino alkyl sulphonic acids, e.g. lauric acid tauride. The higher alkyl-aryl sulphonates may also be used. The aromatic nucleus may be mononuclear or polynuclear in structure, and may be derived from benzene, toluene, xylene, phenol, cresols or naphthalene. The alkyl substituent may be straight or branched-chain in structure; specified alkyl groups include decyl, dodecyl, keryl, pentadecyl, hexadecyl and mixed alkyl groups containing at least 8 carbon atoms derived from long-chain fatty materials, cracked paraffin wax olefins or polymers of olefins such as propylene tetramer. The alkyl group may have 8 to 22 carbon atoms, and preferably 12-18. The detergents may be used as their water-soluble amine, alkali-metal or alkaline-earth metal salts, preferably the alkylolamine (especially mono-, di- and triethanolamine) salts. The ratio of dialkylolamide to anionic detergent may be between about 1 : 10 to about 2 : 1 by weight, preferably from about 1 : 7 to about 1 : 1 by weight. Depending on the solvent power of the selected solvent, the amount of total solids in the composition may be from about 30 per cent. to about 90 per cent., preferably at least 40 per cent. The amount of anionic detergent may be 40-60 per cent. and that of dialkylolamide 10-20 per cent. The dialkylolamide may be incorporated in the detergent at any stage of the manufacturing process, but it is preferred to add the molten dialkylolamide to a warm water, aqueous alcohol or alcohol solution of the detergent or to dissolve the dialkylolamide in alcohol or water and add the so formed solution to the detergent. Further dilution to the desired concentration may be necessary. In an example (all parts by weight) 13 parts of lauric diethanolamide, 44.7 parts of the triethanolamine salt of dodecyl benzene sulphonate, 7.5 parts of triethanolamine sulphate, 22.3 parts of water and 12.5 parts of ethyl alcohol are mixed to form a detergent composition.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US159854A US2607740A (en) | 1950-05-03 | 1950-05-03 | Liquid anionic-dialkylolamide detergent composition |
Publications (1)
Publication Number | Publication Date |
---|---|
GB708000A true GB708000A (en) | 1954-04-28 |
Family
ID=22574364
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB9063/51A Expired GB708000A (en) | 1950-05-03 | 1951-04-18 | Improvements relating to liquid synthetic detergent compositions |
Country Status (5)
Country | Link |
---|---|
US (2) | US2607740A (en) |
BE (1) | BE502985A (en) |
CH (1) | CH300865A (en) |
FR (1) | FR1035745A (en) |
GB (1) | GB708000A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4246131A (en) * | 1978-11-20 | 1981-01-20 | Inolex Corporation | Low-irritant surfactant composition |
Families Citing this family (58)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3017363A (en) * | 1962-01-16 | Detergent composition | ||
US2768957A (en) * | 1956-10-30 | Detergent purification | ||
NL80096C (en) * | 1951-04-23 | |||
US2831815A (en) * | 1952-12-17 | 1958-04-22 | Colgate Palmolive Co | Detergent compositions |
US2908651A (en) * | 1954-05-07 | 1959-10-13 | Colgate Palmolive Co | Liquid detergent composition |
NL200262A (en) * | 1954-09-30 | |||
US2978416A (en) * | 1955-07-14 | 1961-04-04 | Allied Chem | Concentrated aqueous detergent composition |
US2870091A (en) * | 1955-09-01 | 1959-01-20 | Stepan Chemical Co | Detergent composition |
US2920045A (en) * | 1955-09-06 | 1960-01-05 | Colgate Palmolive Co | Heavy duty liquid detergent compositions |
US2927081A (en) * | 1956-01-31 | 1960-03-01 | Lever Brothers Ltd | Detergent composition containing n-tris (methylol) methyl amides |
US2969329A (en) * | 1956-04-12 | 1961-01-24 | Monsanto Chemicals | Detergent compositions |
DE1075779B (en) * | 1956-06-29 | 1960-02-18 | The Procter &. Gamble Company, Cincinnati, Ohio (V. St. A.) | High-performance, liquid cleaning agent |
DE1074187B (en) * | 1956-10-03 | 1960-01-28 | The Procter ·&. Gamble Company, Cincinnati, Ohio (V. St. A.) | Thixotropic, liquid cleaning agent |
US2943058A (en) * | 1956-10-15 | 1960-06-28 | Diamond Alkali Co | Liquid detergent compositions |
US2859182A (en) * | 1956-11-02 | 1958-11-04 | Lever Brothers Ltd | Heavy duty liquid detergent composition |
US2947702A (en) * | 1957-01-23 | 1960-08-02 | Procter & Gamble | Liquid detergent compositions |
US2992993A (en) * | 1957-01-23 | 1961-07-18 | Procter & Gamble | Liquid detergent compositions |
US3001949A (en) * | 1957-01-24 | 1961-09-26 | Colgate Palmolive Co | Shampoo composition |
NL226933A (en) * | 1957-04-16 | |||
US3001944A (en) * | 1957-07-12 | 1961-09-26 | Colgate Palmolive Co | Controlling viscosity of synthetic detergent-soap shampoos |
BE569765A (en) * | 1957-07-25 | |||
US3072580A (en) * | 1957-08-07 | 1963-01-08 | Gillette Co | Shampoo composition |
NL235885A (en) * | 1958-02-10 | |||
US3029205A (en) * | 1958-05-05 | 1962-04-10 | Lever Brothers Ltd | Light duty liquid detergent |
US3021284A (en) * | 1958-10-30 | 1962-02-13 | Atlantic Refining Co | Liquid detergent compositions |
US3023168A (en) * | 1958-11-25 | 1962-02-27 | Atlantic Refining Co | Heavy duty liquid detergent |
US2994665A (en) * | 1959-04-15 | 1961-08-01 | Lever Brothers Ltd | Heavy duty liquid detergent compositions containing a pair of cellulosic soil suspending agents |
US2980625A (en) * | 1959-05-11 | 1961-04-18 | Sterling Drug Inc | Dispersions of benzimidazolylstilbene whitening and brightening agents and production thereof |
US3150098A (en) * | 1959-06-01 | 1964-09-22 | Lever Brothers Ltd | Liquid detergent |
BE607967A (en) * | 1960-10-28 | |||
US3101324A (en) * | 1960-12-12 | 1963-08-20 | Colgate Palmolive Co | Liquid detergent composition |
US3052635A (en) * | 1960-12-14 | 1962-09-04 | Colgate Palmolive Co | Liquid laundering compositions |
US3229777A (en) * | 1961-03-22 | 1966-01-18 | Swift & Co | Method of transporting water from a well as a substantially stable foam |
GB1084061A (en) * | 1965-12-09 | |||
CA714018A (en) * | 1961-05-26 | 1965-07-20 | Colgate-Palmolive Company | Hard surface cleaning compositions |
NL280446A (en) * | 1961-07-03 | |||
NL136443C (en) * | 1961-07-03 | |||
CA720078A (en) * | 1961-11-24 | 1965-10-19 | Swift And Company | Liquid detergent |
CA729145A (en) * | 1962-03-20 | 1966-03-01 | The Procter & Gamble Company | Built liquid detergent |
US3223186A (en) * | 1962-05-23 | 1965-12-14 | Pan American Corp | Method of drilling with air or gas |
CA708145A (en) * | 1962-07-03 | 1965-04-20 | C. Taylor Robert | Water-soluble liquid detergent compositions |
US3226331A (en) * | 1962-07-03 | 1965-12-28 | Atlantic Refining Co | Oil-soluble liquid detergent compositions |
CH413776A (en) * | 1963-02-08 | 1966-02-15 | Geigy Ag J R | Process for dyeing or printing textile fibers made of organic material |
US3313735A (en) * | 1963-09-25 | 1967-04-11 | Procter & Gamble | Shampoo composition |
US3325416A (en) * | 1963-10-01 | 1967-06-13 | Colgate Palmolive Co | Synthetic gum dispersions |
GB1143703A (en) * | 1965-03-18 | |||
US3441510A (en) * | 1965-10-12 | 1969-04-29 | Vego Chem Corp | Detergent composition |
US3549544A (en) * | 1966-10-03 | 1970-12-22 | Swift & Co | Liquid synthetic detergent |
US3451957A (en) * | 1967-02-03 | 1969-06-24 | George A Pritchard | Impregnating and coating compositions and articles and products treated therewith |
US3903008A (en) * | 1972-05-01 | 1975-09-02 | Lanvin Charles Of The Ritz Inc | Cleansing bar |
JPS518644B2 (en) * | 1972-07-19 | 1976-03-18 | ||
US3843543A (en) * | 1972-10-13 | 1974-10-22 | Colgate Palmolive Co | Soap curd dispersant |
US4179414A (en) * | 1978-10-23 | 1979-12-18 | Mobil Oil Corporation | Fatty acid diethanol amide-containing general purpose cleaner in paste form |
US4338211A (en) * | 1980-06-30 | 1982-07-06 | The Procter & Gamble Company | Liquid surfactant skin cleanser with lather boosters |
JPS58117292A (en) | 1981-12-30 | 1983-07-12 | ライオン株式会社 | Detergent composition |
US4919838A (en) * | 1988-09-30 | 1990-04-24 | Hubert M. Tibbetts | Bar shampoo and skin soap |
FR2735495B1 (en) * | 1995-06-14 | 2003-03-07 | Rhone Poulenc Chimie | REDUCED IRRITATING COMPOSITION CONTAINING ANIONIC SURFACTANTS |
US8444720B2 (en) | 2006-09-21 | 2013-05-21 | Afton Chemical Corporation | Alkanolamides and their use as fuel additives |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2173448A (en) * | 1937-05-17 | 1939-09-19 | Emulsol Corp | Preparation of alkylolamine derivatives |
US2383737A (en) * | 1942-02-18 | 1945-08-28 | Procter & Gamble | Detergent composition |
-
0
- US US23840D patent/USRE23840E/en not_active Expired
- BE BE502985D patent/BE502985A/xx unknown
-
1950
- 1950-05-03 US US159854A patent/US2607740A/en not_active Expired - Lifetime
-
1951
- 1951-03-03 FR FR1035745D patent/FR1035745A/en not_active Expired
- 1951-04-18 GB GB9063/51A patent/GB708000A/en not_active Expired
- 1951-05-02 CH CH300865D patent/CH300865A/en unknown
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4246131A (en) * | 1978-11-20 | 1981-01-20 | Inolex Corporation | Low-irritant surfactant composition |
Also Published As
Publication number | Publication date |
---|---|
BE502985A (en) | |
CH300865A (en) | 1954-08-31 |
USRE23840E (en) | 1954-06-15 |
US2607740A (en) | 1952-08-19 |
FR1035745A (en) | 1953-08-28 |
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