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
  • C11D1/02—Anionic compounds
  • C11D1/04—Carboxylic acids or salts thereof
  • C11D1/08—Polycarboxylic acids containing no nitrogen or sulfur

Definitions

• the present invention relates to non-toxic and biodegradable surfactants derived from succinic acid.
• an object of the present invention is to provide esters of succinic acid having the general formula: R-A n -OOC-CH2-CH2-COOR1 (I) wherein: R1 is a hydrogen atom, a metal ion, an ammonium group, the cation of an organic amine base or a group having the formula: -A n -R (II) wherein A is an oxyethylene group -CH2-CH2O-, n is a number from 1 to 20 and R is a C8-C20 alkyl group.
• the metal ion is preferably selected from sodium, potassium and magnesium.
• the cation of an organic amine base is, for instance, derived from an alkanolamine such as monoethanolamine or triethanol­ amine.
• the radical R is preferably selected from linear or branched alkyl groups containing 10 to 16 carbon atoms, n ranging preferably from 4 to 10.
• a further object of the present invention is to provide a process for preparing the esters having formula I, which process comprises the esterification of succinic acid with an aliphatic polyoxyethylated alcohol of formula III: R-A n -OH (III) wherein R, A and n have the above-mentioned meaning, at a temperature of from 150 to 190°C under continuous distilla­tion of water formed during the reaction and, optional subse­quent conversion of the obtained product into a salt with metal bases, ammonia or amines.
• either the mono- or the diester may be prepared as preferred.
• the acid and the polyoxyethylated alcohol are reacted in substantially equimolar ratios, whereas they are reacted in molar ratios of about 1:2 in order to produce the diester having formula (V).
• reaction may be represented by the following equation:
• polyoxyethylated alcohols of formula (III) are known, commercially available products which may be prepared by reacting the alcohol with ethylene oxide, using an alkaline base as a catalyst.
• Preferred alcohols are the ethoxylated alcohols having the formula: R-(OCH2CH2) n -OH, wherein R is a linear or branched alkyl group containing 10 to 16 carbon atoms and n ranges from 4 to 8, as well as mixtures thereof.
• esters according to the present invention and, in par­ticular, the monoesters of the aliphatic ethoxylated alcohols and their salts are very efficient surfactants which, even when used at very low percentages, result in a remarkable lowering of the surface tension and, therefore, can be used as emulsifying agents, dispersants and as detergents in general.
• esters according to the invention proved to be compatible with most known surfactants and, therefore, they can be for­mulated in combination with them. Owing to their spectrum of characteristics, the esters according to the invention are very flexible in their use in the different applications of surfactants. An account of their high detergent power combined with the lack of toxic effects on the skin, hair, and eyes, they are particularly suitable for beauty care applications such as, for instance, the preparation of liquid or creamy detergents for the skin, of shampoos and bath foams.
• the solution thus obtained can be used either as such or in a diluted form in the different fields of use of deter­gents.
• a product ha­ving a creamy consistency and predominantly consisting of the sodium salt of succinic monoester, having an acid number of 4.4, a saponification number of 81.2, an ester number of 76.8 and a pH at 1% of 7.2 was obtained.
• the salified product dissolves in water at any ratio.
• the surface tension measured at 20°C according to the Du Nuoy method was 34.6 dynes/cm at a concentration of 0.25 g/l and 34.2 dynes/cm at a concentration of 1 g/l.
• the wetting power, determined on the product at a concentra­tion of 2 g/l in distilled water was 90 seconds.
• the salified product was highly biodegradable, non-toxic, non-irritating and endowed with a very good detergency power.

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)
• Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Detergent Compositions (AREA)
• Cosmetics (AREA)

Applications Claiming Priority (2)

Publications (2)

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Family Applications (1)

Country Status (4)

Cited By (5)

Citations (3)

• 1985
  • 1985-07-30 IT IT21765/85A patent/IT1187719B/it active
• 1986
  • 1986-07-24 JP JP61172914A patent/JPS6270340A/ja active Pending
  • 1986-07-29 EP EP86110434A patent/EP0210642A3/de not_active Withdrawn
  • 1986-07-29 ES ES8600669A patent/ES2003738A6/es not_active Expired

Patent Citations (3)

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