JPS6270340A - Surfactant derived from succinic acid - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to non-toxic, biodegradable surfactants derived from succinic acid.

Among the many types of surfactants known, a single surfactant is particularly versatile as such, with various properties such as biodegradability, non-toxicity, non-irritation to the skin, and high water solubility. For example, make-up (
It is rare that they also have excellent cleaning properties that make them equally applicable in various fields such as toilets, beauty products, food industry, textile industry, and emulsion polymerization.

The present inventors have therefore developed novel surfactants derived from succinic acid, in particular monoesters of succinic acid and polyoxyethylated aliphatic alcohols, which combine these properties and are therefore useful for a wide range of applications. and/or surfactants consisting of diesters and their salts with inorganic or organic bases.

Therefore, the object of the present invention is to obtain the general formula % () [wherein R1 is a hydrogen atom, a metal ion, an ammonium group,
An organic base cation of ammonium or a group of the formula %() (where A is a -CH2CH20-oxyethylene group, n is a number from 1 to 2D, and R is a C8-C2° alkyl group). An object of the present invention is to provide an ester of succinic acid having the following properties.

The metal ion is preferably selected from the group consisting of sodium, potassium and magnesium.

Ammonium organic base cations can arise from alkanolamines such as, for example, monoethanolamine and triethanolamine.

The radical R is preferably selected from the group consisting of linear or branched alkyl groups having 10 to 16 carbon atoms, and n preferably ranges from 4 to 10.

Another object of the invention is to provide a process for the preparation of esters having the formula CI), in which succinic acid is converted to 150-19 by polyoxyethylated aliphatic alcohol
The object of the present invention is to provide a method comprising esterifying at a heating temperature of 0° C., constantly distilling off the reaction water formed during the process, and optionally salting the obtained esterified product with a metal base, ammonia or an amine.

By this method, mono- to diesters are obtained, each having the following formula: Monoester of succinic acid: RAnOOC-CH2-CH2-C00T-I
(■) Diester of succinic acid: RAnOOC-CH2-C'H2C0OAnR (V) Depending on the reaction conditions used, in particular the molar ratio of succinic acid and polyoxyethylated alcohol, either the monoester or the diester is desired. can be manufactured.

Thus, to selectively prepare a monoester having the formula (I), an acid and a polyoxyethylated alcohol are reacted in approximately equimolar ratios, and to prepare a diester having a human, the above compound is reacted in approximately equimolar ratios. React at a ratio of =2.

When producing a monoester of succinic acid and polyoxyethylated alcohol, the reaction is expressed by the following formula:
(-OCR+ CH2-) ----00C-CH2-
Polyoxyethylenated alcohols having the formula (III) -C0OH are commercially available compounds, but can also be prepared by reaction of alcohols with ethylene oxide catalyzed by alkali bases.

Thus, among the alcohols, those with the formula R-(0CH2CH2) n-OH, where R is a linear or branched alkyl of 10 to 16 carbon atoms,
Ethoxylated alcohols with n=4 to 8) and mixtures thereof are preferred.

The esters according to the invention, in particular the monoesters of ethoxylated fatty alcohols and thereafter, are very efficient surfactants which, although used in very small proportions, can significantly lower the surface tension and therefore Generally emulsifier,
It can be used as a dispersant and detergent.

In addition to their excellent cleaning properties, the surfactants of the invention do not have any toxic or irritating effects on the skin or eyes and are not acutely toxic when taken by the oral route.

It is highly biodegradable, exceeding 90%.

Furthermore, it is stable over a wide temperature range up to 100°C.

Furthermore, they have very good wetting and foaming power and may have moderate or excellent water solubility.

In particular, the solubility increases as the number of moles of ethylene oxide contained in the alkyl ether increases.

It has been found that the esters according to the invention are compatible with most of the known surfactants and may thus be processed together.

Owing to their overall properties, the esters according to the invention are very versatile in different fields of use of surfactants.

Due to its high detergency and lack of toxic effects on the skin, hair and eyes, it is particularly suitable in the cosmetics field, for example in the production of liquid or cream skin cleansers, shampoos and baths. There is.

The following examples illustrate the invention and do not limit it in any way.

Example 1 Monoesterification of succinic acid A reactor equipped with a heating system, a stirrer, a thermometer, and a reactant supply system and connected to a condenser with a manifold for collecting reaction water was charged with 165.3 ml (14 moles) of succinic acid and LIAT. ,
Mixture of ethoxylated alcohol (average molecular weight = 505) with 123 7 ETO (formula % formula % and n = 7)] 71α5 (1407 mol)
was introduced under nitrogen flow.

The mixture was heated to a temperature of 188-190"C within about 90 minutes, at which point the reaction water began to distill, with continued stirring under nitrogen flow, and then to 198-2 (lo"C).

65% of the theoretical value of esterification reaction water (25,2L; I)
When distilled, the acid value was measured.

When the acid value reaches 95-96 (theoretical value 9'2.7),
The esterification reaction was completed.

Thereafter, the reaction mixture was cooled to 80"C and the contents of the reactor were discharged. Water content α<1%, acid value 95
．． A liquid product 8489 was obtained with a saponification number IRQ of 0 and a saponification number of 7. Analysis showed that the product consisted primarily of succinic acid monoester.

In a vessel equipped with a salt-forming stirrer, a thermometer, an addition funnel and a water cooling system, add 254.4 ml of the succinate ester prepared as described above.
g and deionized water 71409 were introduced.

The whole was stirred until a homogeneous emulsion was obtained, and then 51.6 g of a 30% NaOH solution were slowly introduced over a period of about 1 hour through a stirring addition funnel, keeping the temperature below 24.degree.

Nl! 1000 liters of a clear aqueous solution containing chlorosuccinic acid monoester/L/25% by weight was obtained.

The solution thus obtained can be used as it is in various cleaning applications, or can be used in a pre-diluted state.

By removing water from the solution, the acid value is 44 and the saponification value is 8.
12, ester value 76.8 and pH 7 at 1%,
A product with a cream-like consistency consisting mainly of succinic acid monoester sodium salt was obtained.

This chloride was soluble in water at any ratio.

The surface tension of the chloride was measured at 20°C according to the surface tension Genoulli method, which was 12
The wetting power measured for the product at a concentration of 29/L in distilled water was 90 seconds. .

Foaming power was measured using a 50-stroke plunger thread with a poated disc on a 200-degree aqueous solution of product 29/17a and gave the following results.

After the following time (min): Foam, - In addition, the chloride of this example was highly biodegradable, non-toxic and non-irritating, and had very high detergency.

Procedural amendment (method) % formula % Display of the case 1985 Patent Application No. 172914 Title of the invention Relationship with the case of the person making the amendment to the surfactant derived from succinic acid Patent applicant name Title
Latufineria ori 4. Lupurifuikantei Erle O Erle Socheta Bel Azzioni Column of patent applicant of application subject to amendment Power of attorney and its translation Contents of each amendment (one copy each) As shown in the attached sheet

Claims (8)

[Claims] (1) General formula RAnOOC-CH_2-CH_2-COOR^1(
I) [In the formula, R^1 is a hydrogen atom, a metal ion, an ammonium group, an organic base cation of ammonium, or the formula -An-R (II) (where A is -CH_2CH_2O-oxyethylene group, and n is 1 to 20, R is C_8 to C_2
An ester of succinic acid having _0 alkyl group). (2) Ester according to claim 1, wherein in the group of formula -AnR (II), n is a number from 4 to 10 and R is alkyl having 10 to 16 carbon atoms. (3) The ester according to claim 1, wherein R^1 is a metal ion, ammonium or amine group. (4) The ester according to claim 1, wherein R^1 is -AnR. (5) General formula RAnOOC-CH_2-CH_2-COOR^1(
I) [In the formula, R^1 is a hydrogen atom, a metal ion, an ammonium group, an organic base cation of ammonium, or the formula -An-R (II) (where A is -CH_2CH_2O-oxyethylene group, and n is 1 to 20, R is C_8 to C_2
A method for producing an ester of succinic acid having the formula R-An-OH (III) where R, A and n are as previously described. 150-19 by the polyoxyethylated aliphatic alcohol (having a meaning)
A process consisting of constantly removing the water of reaction during esterification at a temperature of 0° C. and optionally salting the esterified product obtained with a metal base, ammonium or amine. (6) the base is selected from the group consisting of sodium, potassium, magnesium or ammonium hydroxide, sodium or potassium carbonate or bicarbonate, triethanolamine and monoethanolamine;
A method according to claim 5. (7) A cosmetic or cleaning composition containing one or more succinic acid esters having the formula (I) according to any one of claims 1 to 4. (8) A surfactant comprising an ester having the formula (I) according to any one of claims 1 to 4.