DE3345879A1 - DOUBLE SALTS OF AMINE AND ALKALINE METAL OF AZYLAMIDOALKYLENE- (OR AZYLAMIDO-N-HYDROXYALKYL-N-ALKYLENE) - SULFERNETRICONIC ACID, METHOD FOR THE PRODUCTION AND USE THEREOF - Google Patents

Description

_ 5 -

DOUBLE SALTS OF AMINE AND ALKALIMETAL OF AZYLAMIDOALKYL] (OR - AZYLAMIDO-N-HYDROXYALKYL-N-ALKYLENE) -STJLFOBERNSTEIn-ACID, METHOD OF MANUFACTURING AND USING THEREOF

The present invention relates to interface active Substances, in particular, it relates to new compounds, double salts of amine and alkali metal Azylamidoalkylene (or azylamido-U-hydroxyalkyl-N-alkylene) sulf © succinic acid, a process for their manufacture and use as a detergent.

The compounds mentioned are used as anionic surface-active substances for the Manufacture of household chemistry products, in particular for the manufacture of cosmetic products,. for example shampoos for washing hair,

Foam detergents for tubs, toilet bars, Stabilizers in the manufacture of cosmetic products and in compositions for cleaning carpets, for y / ashing of wool products, especially in cold water, ■ also used in the cinema and photo industry as a wetting agent when applying photo emulsions to film will.

Ή The modern cosmetic surfactants

should have a high foaming capacity and high foam stability of the aqueous solutions, good solubility in hard cold water, mild dermatological and moderate degreasing effect, as well as easy biodegradability exhibit· . -.

. Surface-active substances of the type are known Disodium salts of azylamidoethylene sulfosuccinic acid, obtained from the Kottonsoapstock of the Ö! extraction companies (Uzbek Chemical Journal of the Academy 3> 0 of Sciences of the Uzbek SSE, No., J, pages

1975). Their formula is 0 as follows

- 0 - NH - CHo - CH ₀ -OC-CH - CH ₀ - COONa,

Il \

O SO ₃ Na

where R stands for a (Cr ₇ -C ^ r ₇ ) -hydrocarbon radical · These substances "have, however, an insufficiently soluble

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ability in cold water _n with only paste-like detergents being obtained on their basis, which are not very suitable for cold washing.

Surface-active substances are also known, obtained on the basis of coconut, palm and other vegetable oils (IE-PS Rr. 2408895) and on the basis of synthetic fatty acids (Uzbek chemical journal of the Academy of Sciences of the Uzbek SSR ₉ No. 3, pages 52-54, 1975).

When using some vegetable oils, synthetic ones Fatty acids or animal fats that are a saturated Carbon chain longer than 13 carbon atoms contain, as a raw material you get surface-active e Substances that are sparingly soluble in cold water and have low surface-active properties. The surface-active substances based on this raw material are not very suitable for cosmetic purposes. The surface-active substances are of the type Made on the basis of fatty acids with a maximum number of carbon atoms of 14, an excessive degreasing Effect*

The invention is based on the object of new surface-active To develop substances that have a high foaming capacity and high foam stability, good solubility in cold water exhibit a mild effect on the skin and through the recovery of in the Companies in the fish processing industry Soapstocks are preserved "

The substances according to the invention are new.

The new substances according to the invention, the double salts of amine and alkali metal of the azylamidoalkylene (or azylamido- ^ T-hydroxyalkyl-lT-alkylene) sulfo-succinic acid have the following general formula:

CNR ₀ -O Pl ³ -

0 R ^

I ^c

C - CH ₀ - CH
Il ² I.

SO

. _; :. '.. ^; . . ::. "■ ' 3345379

where R- stands for a (Cq - ^c ? 1 ^ hydrocarbon radical of linear structure,

JR

₂ H, -CH ,, -CH ₂ -CH ,, -CH ₂ -CH ₂ -OH, -CH ₂ -CH -OH

or ■ -. ^CH 5

-CH- CH - CH-, means

l ι 3

GH, OH P-

B, for -CH ₀ - CH ₀ -, -CH ₀ -CH - or -CH - CH-, ·

3. 2 2 »2 - \ Ll ⁱ

CH, CH-. CH,

: ■ · · P ^YY

E ^, Hc, -Eg H and / or -CH ₂ - CH ₂ -OH, ■ · Me is Na or K. · - '

The new compounds according to the invention are dough-like substances which are completely soluble in cold water (the 40% solution is transparent, flows well at a temperature of 20 ^° C., does not become cloudy on storage). The compounds have good heat resistance · They also have mild dermatological properties and are readily biodegradable ·

The structure of the compounds according to the invention was confirmed by the data from ΙΕ spectroscopy. In the 20 'spectra one observes characteristic bands of the following functional groups:. . .

Alkyl radical 725-720 cm " ¹ ,

CH ₅ -J-CH ₂ groups 2960, 2940-2910, 2870 cnT ¹

-CO-OT group. 3350-3300.3050-3010 cm """ ¹ ,

Ü _,

-σ-0 group · 1750-1735 cm ',

-CO ₂ "" -Ion I6IO-155O, i450r-1300cm ~ ¹ ,

-OH group 3500-3 250, 10 50-1030

-SO ₂ -O-GrUpPe 1420-1330, 1

-Ϊ? Η ~ -Ιοη 33ΟΟ-3Ο3Ο cm "" ¹ .

The presence of the dual charge of the anion in the inventive Compounds were made using the cation exchange method confirmed in alcoholic aqueous solution.

The density of the aqueous solutions of said compounds at the same concentration ei.ner to percent by weight and a temperature of 2O ⁰ C in 24 in- a

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Range from 1.062 to 1.1020 kg / m, the dynamic viscosity of these solutions at a temperature of 20 ° C. is in a range of 20 to ^{4 MPa »s.}

The new compounds according to the invention have the properties of surface-active substances.

The foaming capacity of these substances, determined according to Ross-Miles at a ^ temperature of 40 ⁰ C and a concentration thereof of 0.25 percent by mass, is distilled by an initial height of the foam column. Water from 180 to 196 mm and a foam tab i Ii 1; at Hcj / H ,. from 0.9 ^ to · 0.98 · In hard water with a concentration of calcium and magnesium salts of 5 »55 meq / l, the initial height of the foam column is 185 to 205 mm and the foam stability is 0.95 to 0.97 · The washing power of the new compounds was determined by standard methodology (FW Newolin "Chemistry and Technology of Synthetic Detergents", Pischevaya Promysbleanost Verlag, Moscow 1971 »pages 405-415). At a concentration of these compounds of 0.25 percent by weight, their washing power is 90 to 96 ·

The surface tension of the aqueous solutions of the novel compounds was determined according to the method at a stalagmometrischen! Temperature of 20 ⁰ C and a concentration thereof in aqueous solution of 0.1 percent by mass. It is from 28.1 to 31.6 x 10 "" ^ Ή / m.

The inventive method for the preparation of the new compounds according to the invention consists in that fat-containing waste from the waste water produced in the fish processing industry, the fatty acid ¹ UNCL glycerides with an acid number of at most 50 mg KOH / g _{s and} a saponification number of 181 to 192 mg-KOH / g and a bromine number of 60 to 70 mg Br / 100 g, treated with methanol in the presence of sulfuric acid under boiling and a reaction mixture is obtained from which the fat layer consisting of the glycerides and methyl esters of the fatty acids is separated, this treated in the presence of sulfuric acid at a temperature of 50 to 6O ⁰ C with methanol and a reaction mass is obtained from the

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an anhydrous fat layer is separated off and treated in the presence of alkali with methanol at the boiling point of methanol and a. The reaction mixture contains the methyl esters of the fatty acids, which are separated off and mixed with alkylolamine, which is taken in an amount of 25 to 55 percent by weight, based on the amount of the methyl esters of the fatty acids, in the presence of a catalyst selected from an alkali metal or its amide or alcoholate, treated at a ^ temperature of 70 to 90 ⁰ C and Al-

IÖ kylolamide the fatty acids obtained with maleic anhydride Treated at a temperature of 60 to 90 ° 0 and obtained alkylolamide maleates of the fatty acids and then this with sodium or potassium pyrosulphite and ethanolamine or ammonia at a temperature of 60 to 90 ° C treated in an aqueous medium and the end product separated. ■. . '-'

For the purpose of improving the quality of the end product, the methyl esters of the fatty acids are used der. mentioned treatment of the same with alkylolamine in Presence of the mentioned catalyst with alkylolamine in an amount of 5 to 10 percent by weight, based on the weight of the methyl esters of the fatty acids, taken, is pretreated at a temperature of 70 to 80 ° C, after which the consumed alkylolamine is removed · The alkylolamine is expediently used Monoethanolamine, diethanolamine, diisopropanolamine, N- -Methylethanolamine, H-A. ethylethanolamine or dibutanolamine.

For the purpose of simplifying the technology of the Process in the stage of amidation of the methyl ester

^ O fatty acids are expediently used as a catalyst ator II atrium-2-amine ethoxylate.

The ethanolamine is expediently used Mono-, di- and / or Q5? Iä than olamine.

The method according to the invention is carried out as follows

Fat waste containing fatty acids and glycerides from the fish processing industry Wastewater with an acid number of at most

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50 mg ΚΌΗ / ε, a saponification number from 181 to 192 mg KOH / g, a bromine number from 60 to ? 0 mg Br / 100 g is treated with methanol in the presence of sulfuric acid as a catalyst Fatty acids contained in the fat waste in sewage. The esterification reaction is carried out with stirring of the reaction mixture at the boiling point of the methanol within 1.5 to 2.5 hours. After the reaction has ended, the mixture is left to stand, the upper layer (methanol) is separated off and passed on for regeneration, while the lower layer treats the fat mixture ₉ with methanol at a temperature of 50 to 60 ° C. in the presence of sulfuric acid When the separation is done, the upper layer (extraction methanoi) is separated and the process goes back to the beginning of the technological cycle for acid esterification of the free fatty acids of the fatty waste from the wastewater. The lower layer, the cleaned fat mixture, is sent to the alkaline transesterification of the glycerides * To do this, the cleaned fat mixture is treated with methanol in the presence of alkali. The mixture is stirred at the boiling point of methanol within 0.25 hours, then cooled to room temperature, left to stand for 1.5 to 2.0 hours to separate, and the layers are separated off. The lower layer, glycerine and methanol, is used to regenerate the methanol. The upper layer of the methyl esters of the fatty acids is washed with hot water, acidified hydrochloric acid and dried. The methanol is regenerated from the washing water. The dried methyl esters are subjected to fractional vacuum distillation at a temperature of 155 to 215 ° C. and a residual pressure of 10 to 20 torr. The yield of the desired fraction is 78 to 8%, based on the starting fats of the fat waste in the wastewater. The purified methyl esters of the fatty acids are treated with the alkylolamine in an amount of 25 to 55 percent by weight, based on the amount of the methyl esters of the fatty acids, taken at a temperature of 70 to 90 ^° C. in the presence of a

Catalyst, the catalyst is an alkali metal or its amides or alcoholates in suitable: · One obtains alkylolamides of fatty acids · For the purpose of simplification of the technology of ^l j process the catalyst used is sodium 2-aminoäthoxylat.

The alkylolamine used is monoethanolamine, diethanolamine, diisopropanolamine, N-methylethanolamine and others
For the purpose of improving the quality of the end product, the methyl esters of the fatty acids are prior to said treatment of the same with alkylolamine in the presence of the mentioned catalyst with alkylolamine, which is taken in an amount of 5 to 10 percent by weight, based on the weight of the methyl esters of the fatty acids, at a temperature of 70 to 80 ⁰ C of the spent pretreated Alkylolamins under subsequent Abstehenlassen and removal.

The yield of alkylolamides of the fatty acids is depending on the degree of conversion of the alkylolamines 93 to 98% the OSieorie

The alkylolamides obtained is stirred with 30 to 37 weight percent maleic anhydride (based on the alkylolamide) at a temperature of 60 to 90 ⁰ C within 1.5 to 3.5 hours, the yield after the degree of conversion of the acids anhydrides times in s. Is equal to theory.

The maleate obtained the alkylolamides is treated with sodium pyrosulfite and potassium pyrosulfite or ethanolamine or ammonia at a temperature of 60 to 90 ⁰ C in an aqueous medium ·

The end product is obtained

The yield of the end product is 70 to 82%, based on the alkylolamide used · The inventive method allows the to recycle the soapstocks that are produced in the fish processing industry and are therefore expensive Edible fats and oils and synthetic petroleum products

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to replace those currently used for the manufacture of surfactants are used. Besides that environmental pollution is reduced. The procedure is simple in its technological design and requires no special equipment. The soapstocks used in the process according to the invention were. which up to now has not been used for fine organic synthesis due to excessive contamination. The inventive Mass procedure allows it thanks to the above technological operations, from the said Produce high-quality end products based on raw materials based on detergents without the use of special additives have been developed to improve their dermatological and washing effect

Another invention is the use of the invention new substances as the basis for detergents. l. The use of the double salt of Έτιethanolamine and is preferred Sodium der Azylami do athyle η sulfobernstein acid ...

The detergent, which includes a surfactant, an odor control agent and water, contains according to the invention as a surface-active substance a double salt of iEt? iäthanolamine and sodium of azylemidoethylene sulfosuccinic acid the formula

II 'II ■

E - G - NE- CH ₂ -CH ₂ -O- .. C - CH ₂ - CH - COONHCC ₂ H ₄ OH) ₃ ,

SO ₃ Na

where E is a (C,., - - C.q) hydrocarbon radical, with the following ratio of the named components:

Double salt of triethanolamine and sodium the azylami-. doä thy Ie η sulf upper s te in acid 5.0 to 32.0 percent by weight Odor improver 0.1 to 1.5 percent by weight water * ..., everything else.

A preferred variant of the detergent is an agent which additionally contains diethanolamide of the (Cq - C ^ r ₇ ) fatty acids, sodium chloride and ethyl alcohol with the following ratio of components

The double salt of triethanolamine and sodium Acylamidoethylene sulphinic acid 12.0 to 20.0 percent by mass

Diethanolamide of (Cq - CL7) fatty acids 0.5 to 3.5 Mass process .. "· - '■.

Sodium chloride 1.0 to 3 »5. Mass percent Ethyl alcohol 0.3 to 1.5 percent by mass. Odor improver 0.1 to 1.5 percent by mass Water ■ everything else

The detergent according to the invention requires in comparison with known agents no use of additives that reduce the degreasing effect. It owns 1.0 good solubility in cold hard water, high foaming capacity and is easy to wash off

In addition, the detergent is mildly dermatological Properties and is easily biodegradable. ■ ·.

For a better understanding of the present invention, the following examples are given:

Example "| .

In a flask with a capacity of 500 ml, equipped with a reflux condenser and a thermometer, place 250 g of fatty waste from the wastewater produced in the fish processing industry (acid number 24 mg KOH / g, saponification number 187 mg KOH / g, bromine number 66.2 mg Br / g 100 density d | ° 0.914 kg / m ^, pour point 13.8 ⁰ C) and 63 g of methanol, acidified with 1 »S 3 (0.0125 gram moles) of concentrated sulfuric acid, a · The mixture is boiled.. within 1.5 hours, during which the fatty acids are esterified. The reaction mixture is allowed to protrude within 0.25 hours separates the upper (methanol) layer and the lower layer consisting of glycerides and Methylestern of the fatty acids decreases, at a temperature from 58 to 6O ⁰ C and 47.5 S Methanol acidified with 0.09g (0.00086 Graamol) concentrated sulfuric acid · After allowing to stand within 0.25 hours, the layers are separated · The upper layer (extraction amethanol) is returned to the original stage of the esterification of the fatty acids.

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The lower layer (245 g) is placed in a flask of 500 ml capacity, equipped with a reflux condenser, a stirrer and a thermometer, and 1.66 g (0.0415 Graranol) of caustic soda in 35 | 6 g (1.113 Gramol) of methanol. The mixture is stirred at the boiling point of the methanol within 0.25 hours, whereby it comes to an alkaline transesterification of glycerides, and then cooled to a temperature of 20 ⁰ C. The reaction mixture is allowed to stand for 0.5 hours, then the glycerol / ethanol layer (the lower layer) is separated. The upper layer Methylester of fatty acids, is washed with water, acidified with hydrochloric acid (0 _r 43'Masseprozent), and distilled at a temperature of 155 "to 215 ° C (15 Torr) under withdrawal of three fractions.

1st fraction of boiling range 155-193 ° O (acid number 2.51 mg KOH / g, saponification value 192 mg KOH / g, Bromine number 52 mg Br / 100g, density d ^ 0.878 kg / m- ^5, pour point '30 ⁰ C , average molecular weight 290.0);

2nd fraction from the boiling range I93 - 202 ° C (acid number 1.5 mg KOH / g, saponification number 189 g KOH / g, bromine number 71 m ^ Br / 100 g, density df ° 0.870 kg / m ^, pour point 9.3 ⁰ C ₁ mean molecular weight 295 »O); 3rd fraction from the boiling range 202-215 ° C (acid number

1.32 mg KOH / g, saponification ungszahl 186 mg KOH / g, 68 mg bromine number g Br / 100, density d | ° 0.867 kg / m ^5, pour point 15.2 ⁰ C, average molecular weight 299.0).

In a flask with a capacity of 500 ml, fitted with a. With a stirrer, a distillation attachment and a thermometer, 295 g (l »00 gramol) of distilled diethyl esters of fatty acids (2nd fraction) and. 30 g (0.491 gramol) of konoethanolamine. At a temperature of 70 to 72 ° C, the mixture is stirred for 0.25 to 0.3 hours, then the stirrer is switched off and, after allowing it to stand, after 0.25 to 0.3 hours, the lower one is removed with a pipette. -darken k.onoäthanolaminschicht. 80 g ( ^{1.3 "r} 0 ol) Lonoäthanolamin add to the flask and stir the egg isch

GQPY
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.for a temperature of 80 ⁰ C, then 6.6 g 37 outputs | 8% solution of the catalyst, the Natoium-2-aminoätho: xylates in monoethanolamine, too. The reaction time is 1.2 hours. The system was vacuumed to a Bestdruck of 200 Torr, the mixture was heated to a temperature of 90 ⁰ C and

the methanol is distilled off. The excess monoethanol is distilled in vacuo at a residual pressure of 20. up to 25 Torr and a temperature of the mixture to be distilled of at most 125 ⁰ C .ab. This gives 528 g Monoäthanoiamid of fatty acids having an average molecular weight of 224. After · Umvvandlungsgrad of monoethanolamine, the yield is 96% ^ ^e ^ theory. '■.

In a flask of 1000 ml capacity, equipped with a thermometer and a stirrer, 324 g of the obtained bringing Mono'athanolamids of fatty acids heated to a temperature of 70 ⁰ C and stirring is .Among within 0.25 to 0 Add 108 grams (1.10 gram mol) of maleic anhydride for 5 hours. Under these conditions the mixture is stirred for 1.5 hours. 432 g of acid maleate of monoethanolamide (azylamidoethylene maleate) are obtained.

A solution of 956 ml of water, 122 g (0.64-2 gramol) of sodium pyrosulfite and 163 g (1.284 gramol) of a mixture of Di. - and triethanolamine of equivalent weight 127 · the solution is heated to a temperature of 60 ⁰ C and poured at this temperature within 0.3 to 0.5 hour via the metering device into that of the acid maleate obtained Monoäthanolamids to sulfonation and neutralization of the latter a. Stirring is continued within 0.3 to 0.5 hours. 1670 g of aqueous solution of the end product, of the double salt of triethanolamine and sodium, are obtained

Azylamidoäthylensulf © succinic acid of the following formula 0 0

RC-NH- CH ^> - CH _p - 0 - C - CH ₅ - CH - COONH (C ₉ H ^ OH).,

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where R. stands for a (C , - - C ^ g) hydrocarbon residue, with an end product content of J1.2 mass percent

Average molecular weight of the final product amounts to 650, the dry subs tan zgehalt _40.2%% of the degree of conversion (the end product / off gangs amide) 82.0%, the solubility in CCL ·, 4.5%, the viscosity at 20 ⁰ C 52, 0 MPa-s, the density d ,, 1.098 kg / nr · the pH value (10% solution) 6.85. . Example 2

The synthesis of the methyl esters of the fatty acids is analogous carried out for example 1. . .

295 g (1.00 gram o.l) of distilled methyl esters of fatty acids (2nd fraction), 30 g (0.285 gramol ) Diethanolamine and carries out the treatment analogously to Example 1 through. Then the Methylestern Priority of fatty acids 110 g (1.05 gram moles) of diethanolamine and 7j3 g 57.8% solution of ITatrium-2-aminoäthoxylat in Monoäthanol- 'to amine, the mixture is stirred at a temperature of 70 ⁰ C to obtain a homogeneous solution. The reaction time is 2 hours. The system was vacuumed to a Bestdruck of 200 Torr, the mixture was heated to a temperature of 90 ⁰ C and distilling off the methanol. 383 g of bioethanol amide of fatty acids with an average molecular weight of 369 times the degree of conversion of diethanolamine are obtained. the yield is 87 % of theory

In a flask of 5OO ml of capacity equipped with a thermometer and a stirrer, bringing 583 g of the obtained Diäthanoiami de one, the mixture is heated to a temperature of 60 ⁰ C and added in portions over 0.5 hours with stirring 142 g ( 1 ^ 5 Gramsiol) maleic anhydride too. The solution is stirred at a temperature of 65 ^° C. for 3 »5 hours and left to stand at room temperature for 12 hours * 525 g of acidic maleate of diethanoiamide are obtained.

(Azylamido-N-hydroxyethyl-Iir-ethylene maleate) '..' '.

A solution of 918 ml of water, 158.5 S (0.854 gramol) of sodium pyrosulfite and 199 * 2 g (1.66 gramol) of a mixture is prepared in a flask with a capacity of 2000 ml, equipped with a thermometer, a stirrer and a metering device di- and triethanolamine by the equivalent weight of 120, heated to a temperature of 80 ^ ⁰ C and poured into it through the metering device with stirring within 0.5 to 0.5 hour, the acid obtained is a Diäthanolamid'maleat.

Stirring is continued within 0.3 to 0.5 hours. 1800 g of aqueous solution of the end product, the double salt of triethanolamine and sodium, are obtained Äzylamido-N-hydroxyäthyl-Ii-ethylensulfosuccinic acid of

following formula ·.

0 0.

Il Il

RGN _{- OH 2} - Oi ^ - 0 - C - GH ₂ -CH - COOi-IH (C ₂ H ₄ OH) ₃

CH ₂ CH ₂ OH 'SO ₃ Na

where R stands for a (0y, c - C ,, q) -coal water to ff remainder with an end product content of 27 percent by mass. The mean molecular weight of the end product is 695 »the dry matter content 46.5%» a degree of conversion (end product / starting amide) 70.0%, the solubility in GGl ^ 6.5%, the viscosity at 20 ⁰ C 28.0 MPa ° s, the density ^d 4 1.088 kg / m ^ the pH value (10% solution) 6.90 · example ?>,.

The synthesis of the methyl esters of the fatty acids is analogous carried out for example 1

153 g (1.00 gramol) of diisopropanolamine, 7i5 S 57-8% solution of sodium 2-aminoethoxylate in monoethanolamine are placed in a flask with a capacity of 500 ml, equipped with a stirrer, a still and a thermometer. 295 S (1.00 gram mol) of distilled methyl esters of the fatty acids (2 * fraction) pretreated with diisopropanolamine are added to the flask and the mixture is stirred at a temperature of 80 to 82 ^° C. within 2 hours. The system is vacuumed to a residual pressure of 200 gtorr, the mixture is heated to a [temperature of

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90 ⁰ C and the methanol is distilled off. 400 g of diisopropanolamide of the fatty acids in the middle are obtained. Molecular weight 396. According to the degree of conversion of the diisopropanolamine, the yield is 92 % of theory.

To 3> 96 g of the obtained Diisopropanolamids are added at a temperature of 60 ⁰ C, 127 g (1.3 Graminol) maleic. acid anhydride is added and the thermostat is at this temperature within 2.5 hours. 523 g of acidic diisopropanolamide maleate (azylamido - ^ - 2-hydroxypropyl-ii- -propylene maleate) are obtained. The sulphonation and neutralization of the acidic diisopropanolamide maleate is carried out analogously to Example 1 by metering it into a solution containing 1440 ml of water, -140 g (0.736 gramol) of sodium pyrosulfite and 219 g (1.47 gramol) of triethanolamine at a temperature of 78 to 80 ⁰ C through. 2290 g of aqueous solution of the double salt of triethanolamine and sodium of azylamido-N-2-hydroxypropyl-N-propylene- 'sulfosuccinic acid of the following formula are obtained

Il ■ I ³ Il

RG-Jf- GH ₂ - CH - 0 - C -GH ₃ - CH-GOONH (G ₂ H ₄ OH) ₃

GH ₂ -CH-OH SO.Na.

CH ^

where R = C ^ c - ^ C ^ q, with a content of end product ". of 24.6 mass percent. The average molecular weight of the end product is 747, the dry matter content 34.7%, the degree of conversion (end product / starting amide ) 75.6, ^, the solubility in CCl. 6.8 %, the viscosity at 20 ^° C.

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26.0 MPa ° s, the density d ^ 1.082 kg / m ^p , the pH-'Pfert (iO% solution) 6.82 "
Example 4

The synthesis of the methyl esters of the fatty acids is analogous carried out for example 1 · '. ·. ·

In a flask of. 5OO ^ffl l capacity., The with-. a stirrer, a distillation head and a thermometer is provided, bringing 110 g (1.465 gram moles) / f methylethanolamine, '7 "0 g 37> 8 / SiGe solution of sodium 2-aminoäthpxylat in monoethanolamine and 265 g (0.898 gram moles) distilled pretreated with N-1'.Ie thy la than olaoiin

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- 19 -: '.. ■■■' ■■

Methylee-ter of the fatty acids (2nd fraction) and stirred at a 'temperature of 50 to 83 ⁰ C within .von 1.5 hours. Then the methanol is distilled off from the reaction mixture as' a vacuum of 200 Torr at a Teaperetur of 90 ⁰ C. The excess N- -L'ethylethanolamine is distilled off at a pressure of 10 to Ϊ5 Torr uri at a temperature of 120 to 123 ⁰ C, 307 g of N-methylethanolamide of the fatty acids with an average molecular weight of 333. Mach .dem degree of conversion of the N ~ Methylethanolamine, the yield is 95% of theory. To 306gdes obtained N-Methyläthanol- ■ amide of fatty acids are added at a temperature of 65 ⁰ C, 110 g (1.122 gram moles) of maleic anhydride ", and it is stirred at this temperature within. 2 hours.

■ 416 g of acidic N-methylethanolamide maleate are obtained (isylamido-N-iaethyl 1-N-ethylene maleate).

The sulphonation and neutralization of the acidic 'N-methylethanolamide maleate is carried out analogously to Example 1 by metering it into a solution which contains 1356 ml of water, 107 g (0.563 gramol) of sodium pyrosulfite and 168 g (1.126 gramol) of triethanolamine at a temperature of 70 ⁰ C through.

2045 g of aqueous solution of the double salt of triethanolamine and sodium of the azylamido-N-ynethyl-lsr- ethylene sulfosuccinic acid of the formula 0 0

H Il.

R - C - N - CHp - CH ₉ - 0 - C - CH ₉ - CH - COOMi (C ₀ H CH ₃ SO ₃ Na

where E stands for a (C15 - C ^ o) - hydrocarbon radical, with an end product content of 27.6 percent by mass. The average molecular weight of the final product amounts to 689 the dry matter content _f 31.5%, the degree of conversion (the end product / starting amide) 82.0% _t solubility in CCl /, 5.7%, the viscosity at 20 ⁰ C 34.0 mPa.s , the density d ^ 1.094 kg / ϊη, the pH value (IO ^ ige solution) 6 _f 96.

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Example 5

The synthesis of the methyl esters of the fatty acids is carried out analogously to Example 1.

In a 500 ml flask with a a stirrer, a still and a thermometer, one brings 290 g (1.00 gramol) -distilled Methyl esters of fatty acids (1st fraction), 29 g (0.475 gramsol) of monoethanolamine and introduces the Treatment analogous to Example 1.

Are then added to the fatty acids Methylestern 72.5 -g '(1.137 gram moles) Mono äthano lain in and 4,8 g of 37% _f Sige solution of Ifatrium-2-aminoäthoxylat in Monoäthano lamin to .. The temperature is raised to 90 ⁰ G and stir at this temperature for 1.2 hours.

The methanol and the excess monoethanolamine are removed analogously to Example 1. 322 g are obtained Monoethanolamide of fatty acids of medium molecular weight 319. According to the degree of conversion of the monoethanoamine the yield is 96% of theory.

To 319 g of the obtained Monoäthanolamids of the fatty acids are added at a temperature of 80 ⁰ G 102 g (1.04 gram moles) of maleic anhydride are added and stirring at this temperature over 1.5 hours. 421 g of acidic monoethanolamide maleate (Azylämidoäthylenüaleai) are obtained.

The sulphonation and neutralization of the acidic monoethenolanide maleate is carried out analogously to Example 1. by metering it into a solution which contains 63O ml of water, 114 g (0.6 gramol) of sodium pyrosulphite and 168 g of a 25% solution of ammonium hydroxide, at a temperature of . 70 ⁰ G

• 30 through. 1330 g of aqueous solution of the double skin are obtained of sodium and ammonium.der Azylamidoäthylenensulfobernst one acid of the following formula

Il. II

EG-NH- GH ₂ -GH ₂ - 0 - C - CH ₂ - GH - GOOmI ₄ ,

SO ₃ Na

where R stands for a (Oq - G ^ <-?) - Koh.lenwasser £ toffrest, with a content of end product of 32 Masfieprοζent.

• .- ■ :. : "- ' ^: - · - ^: - ·" ^: 3345873

The average molecular weight of the end product is 537, the dry matter content 40.8 % , the degree of conversion (end product / starting amide) 81.0%, the solubility in CCl ₄ 4.9 % _t the viscosity at 20 ⁰ C 22.0 MPa.s, the Density d | ° 1.102 kg / m ^, the pH value (10% solution) 6.95.

Example 6 ■

The synthesis of the methyl esters of fatty acids is carried out analogously to Example 1.

299 g (1.00 gramol) of distilled methyl esters of the fatty acids (fraction 0), 20 g (0.327 gramol) of monoethanolamine are placed in a flask with a capacity of 600 ml, which is equipped with a stirrer, a still and a hiermometer and the treatment is carried out analogously to Example 1. 90 g (1.4-73 gramol) of monoethanolamine and 8.2 g of 37.8% solution of i-sodium 2- * aminoethoxylate in monoethanolamine are then added to the methyl esters of the fatty acids is added and stirred at a temperature of 9O ⁰ C within 1.5 hours. the methanol and übeschüssige monoethanolamine is removed analogous to example 1.

330 g of monoethanolamide of the fatty acids with an average molecular weight of 328 are obtained. The yield is 95.5% of the conversion rate of the monoethanolamine. r 25 theory. In a! Temperature 83-85 ⁰ G of Monoäthanolamids obtained are added to 328 g of the fatty acids 121.4 g (1.2 ^ 8 gram moles) of maleic anhydride are added and stirring at this temperature for 2 hours. 44-9 g of acidic monoethanolamide maleate (.fizylamidoethylene maleate) are obtained. Sulphation and neutralization of the acidic monoethanol amide maleate are carried out analogously to Example 1 by metering the same into a solution containing 970 ml of water. 158.3 g (0.712 gramol) potassium pyrosulfite and 149.5 g (1.424 gramol) diethanolamine, at a temperature of 90 ° C. 1720 g of aqueous solution of the double salt of diethanolamine and potassium of .Azylamidoäthylensulf © succinic acid of the formula are obtained

33 * 5879

O O

Il Il

RCM- CH ₂ - CH ₂ - O - C - CH ₂ - CH -

where E is a (P ^ n - C ^ p ^ hydrocarbon radical 1 with a content of end product of 30.3 percent by mass.

The average molecular weight of the end product is 649, the dry matter content 41.4%, the degree of conversion (end product / starting amide) 80.5%, the solubility in CCl ₄ . 4.2% _t the viscosity at 20 ⁰ C 20.0 mPa.s, density djjjT 1.089 kg / m, the pH value.

(IO% solution) 7 »O5. .

Example 7

The synthesis of the methyl esters of the fatty acids is carried out analogously to Example 1.

In a flask of 1000 ml capacity, equipped with a stirrer, a distillation head and a thermometer, bringing 161 g (1 gram-mole _O?) Dibutanolamine, 8.0 g 37i8; £ solution of Ifatrium-2- -aminoäthoxylat in Moiioethanolamine a. 295 g (0.00 gramol) of distilled methyl esters of fatty acids pretreated with dibutanolamine are placed in the flask

(2. Iraq ion), and stirred at a temperature of 80 ⁰ C within 2 hours · The system was vacuumed to a residual pressure of 200 Torr, the mixture was heated to a temperature of 90 ⁰ C and distilling off the methanol.

This gives 428 g of Dibutanolamid! Fatty acids from the 'average molecular weight 424. iTach the degree of conversion of Dibutänolamins the yield is 88 _<0 y theory.

127.5 g are added to 424 g of the resulting dibutanolamide of the fatty acids at a temperature of 75.degree

^ O (1 | 50 gramsol) maleic anhydride and stir at this temperature within 3 hours. This gives 551 g of acidic Dibutanolamidmaleat / izylamido-LF (1-methyl "l-2-hydroxy) propyl-I ⁱ i '- (1,2-dimethyl) äthylenmaleat /. The suIfierung and neutralization of the acidic dibutylamide maleate is carried out analogously to Example 1 by metering it into

a solution containing 1500 ml of water, 142 g (0.747 gram mol) of sodium pyrosulfite and 222 g (1.49 gram mol.) of triethanolamine., at a temperature of 70. ⁰ C through. 2412 g of aqueous solution of the double salt of triethanolamine and sodium of azylamido-IT ~ (1-methyl, 2-hydroxy) propy 1-N- (1,2-dimethy l) ethylenesulf obernsteinäu-

re the following foriael ο
0 GHo GHa _{i

Il. I 3, 5 j |

RCN-GH-GH-OC-, GH ₂ - CH - COOKH (C ₂ H ₄ OH) ₃ CH-CH- CH ₃ SO ₃ Na

CH ₃ OH

where R is a (C ^ cj - C ^) - hydrocarbon radical stands, with an end product content of 24.1 percent by mass

The average molecular weight of the end product is 774.

The dry matter content is 36.2 · ^, the Umv; andlungsgrad (final product / Ausgängsamid) 74.8 f _Oi solubility in CCI ₄ 7.2%, the viscosity at 20 ⁰ C ■ 28.0 mPa.s, the density d ² ° 1.062 kg / m ⁵ , the pH value (IO% solution) 6.95.
3example 8

The synthesis of the methyl esters of the fatty acids is made carried out analogously to Example 1.

116 g (1.30 grams) of F- -thylethanolamine, 7.2 g of 37% sodium solution 2- aminoetho: xylate in monoethanolamine and 295 g (1.00 Grainmol) pretreated with ir-2thyla * thanolamiii, distilled methyl esters of the fatty acids (2nd Braktion) and stirred at a temperature of 80. ⁰ C, within 1, 5 hours. Is then distilled from the reaction mixture from under a vacuum of 200 Torr and a temperature of 90 ⁰ C methanol. The excess ST-Sthyläthanolamin is distilled in a vacuum of IO to 15 Torr at a temperature of 120-125 ⁰ C from. 355 g of li-ethylethanolamide are obtained

BATH ORIGINAL

of fatty acids with an average molecular weight of 552 the degree of conversion of the N-ethylethanoamine is .Yield 95% of theory.

To 352. N-iSthyläthanolamid g of the fatty acids are added at a temperature of 90 ⁰ C 108 g (1,1.0 gram moles) of maleic anhydride and stirring "at this temperature within 2 hours. This gives 450 g of acidic IT Äthyläthanolamidmaleat. The sulfonation and neutralization dessauren N-Xthyläthanolamidmaleates leads one analogously to example 1 by metering it at, a temperature of 70 ⁰ g in a solution containing 1400 ml of water, 120 g '(0.65 gram moles) of sodium pyrosulfite and 77 g (1.26 Granmol). Monoethanolamine contains through.

-N-ethylene sulfosuccinic acid of the following formula 0 0

Il Il

RCN-CH ₂ -CH ₂ -OC-CH ₂ -CH--

CH ₂ -CH ₃ - SO ₃ Na

where E stands for a (C ^ c - G ^ o) -hydrocarbon radical, with an end product content of 24.5 percent by mass.

The average molecular weight of the end product is 614. . ■ - ·. ■

ANZG the dry st sub ehalt is 5 ^, 2% _t the degree of conversion (the end product / starting amide) 81.6.%, The solubility in CCl ₄ 5.9%, the viscosity at 20 ⁰ C.

52.0 MPa. s, the density d | ° 1.086 kg / m ⁵ the pH value (IO ^ ige solution) 7.02. ·

Example 9

The synthesis of the methyl esters of the fatty acids is carried out analogously to Example 1. ·

In a flask of 500 ml capacity, 'the one with' a stirrer, a still and a thermometer is provided, add 295 g. (1.00 gramol) of distilled Methyl esters of fatty acids (2nd fraction), 15 g (0.246 gramol) of monoethanolamine and carries out the treatment log through to example 1. ·

BATH ORIGINAL

- 23 - ... The methyl esters of the fatty acids are given 80 g

Stirred gram moles) of monoethanolamine to the mixture and bed a temperature of 80 ⁰ C, then added 5.6 g of 29 ^ strength sodium methoxide in methanol as a catalyst to · The reaction time is 1.2 hours. The methanol and the excess monoethanolamine are removed analogously to Example 1.

325 g of monoethanolamide of fatty acids with an average molecular weight of 324 are obtained. According to the degree of conversion of the monoethanolamine, the yield is 95.6 % of theory. The process is then carried out analogously to Example 1. An end product which is analogous to that described in Example 1 is obtained. .

The quality characteristics of the connections ^ which according to Examples 1-9 are shown in Tables 1-3 • listed.

Example IO

A bubble bath consisting of the following

Components
Double salt of triethanolamine and sodium of azylamidoethylene sulfosuccinic acid 32 percent by weight

Odor improver 1.5 mass percent ■ ■ water. everything else.

The quality characteristics of the foam bath are shown in Table 4.
Example 11

A children's shampoo consisting of. following components .

Double salt of triethanolamine and sodium of acylamidoethylene sulfosuccinic acid 5 percent by mass

Odor improver 0.1 mass percent

Water everything else.

The quality characteristics of the children's shampoo are shown in Table 4.
Example 12

A hair shampoo consisting of the following components Double salt of · triethanolamine and sodium of acylamidoethylene sulfosuccinic acid 20 mass percent

■ BADORiGINAL

- 26 Diethanolscid of (Cq - Cxjy) -fatty acids 3,5 Kcssepro "

. "-.:. ■ ■ cent

Ethyl alcohol 1.5 percent by mass

Sodium chloride 2.0 cash percent

Odor improver 1.0 percent by mass

Water . everything else.

The quality characteristic of the Haarsiiampoos is in Table 4 listed.

Example 13>

A hair shampoo consisting of the following components: ■. '· "'

Double salt of triethanolamine and sodium of the acylamido-ethylene sulfosuccinic acid ■ 12 IvIa ss epr ο zent ■

Dietethanolamide of (C gC ^ r ₇ ) -fat -

acids '' 3.0 I cash percent

Ethyl alcohol 0.75 percent

liatrium chloride 3.5 percent

Odor improver 0.75 t'a ε ε epr ο ζ drainage everything else.

The quality characteristics of the hair shampoo is listed in Table 4 »

OQPY
BATH ORIGINAL

. ■ Table 1.

Look; abildungsvermögen according Eoss-Miles at a temperature of 40 ⁰ C and a concentration of the inventive compound of 0.25 percent by mass

No, Double Salts of Amine and Alkalime-Be i- tall of the acylamido game alkylene (or acyl-

amido-N-hydroxy-. alkyl-iT-arkylenes} - -sulfosuccinic acid

Cations Distilled water

Height of foam

Foam column, stabi mm Iitat,

TT TJ TJ

H ₀ H ₁ H ₅

Os 60 s 300 s

4 5 6

·

= WaS sers to ff = —CH ₀ -CH _o -

R ₂ =
R ₃ =

· H ₁ =

E _O = -CH _O -CH - OH C

-CH ₀ -GH-2 ι

R ₂ = · hydrogen

E _x = -CH ₀ -CH ₀ -5 2 2

R ₂ = hydrogen

Ε-, = -CH _o -CH _o - 5 2 2

E _O = -CH - ^ CH -CH-2 ι ι

CH, OH

H ₇ = -CH - CH-CH-, CH-, 50% TAA +

. 195 180 175 0.97

N / A/

66% DAA

Na / TÄA

Na / TAA

185 170 166

187 175 168 0.97

196 183 177 0.97

183 170 166 0.98

180 167 160 0.96

182 167 163 0.98

COPY

Table 1 (! Cont.)

R ₁ = C ₁₅ -C ₁₉ Na / I & A 192 180 172 0.96

- CH _x

-CH ₂ - CH ₂ - '

Note «TAA - triethanolamine, dXa - diethan ο lamin, ΜαΆ - monoathanolamine

Table 1 (cont.)

Hard Water (5.55 mVal / 1). Foam stabilizer
did. High . the Foam column, mm ■■ ' Xl f - β Xl j. ^E o
0 s H, H ₅
60 s 500 S. 11 1 8th 9 10

1 205 186 180 0.97

2 190 175 168. . 0.96

5 195 177 170 0.96

202 186 180 0.97

5 190 177 172 0.97

6 185 170 165. 0.97

7 188 175 165. 0.95-

Table 1 (cont.)

J 8 9 10 11

8th · . . 200 185 180 0.97.

■ Table 2.

'^ vision according to the standard wool fabric in one Concentration of the invention masses; Connections from 0.25 mass per cent. '■

Mr. of

Poppel salts of amine and alkali metal cations the azylamidoalkylene (or azylamido- _ ^ _ hydroxyalkyl-li-alirylene) - sulf succinic acid

^E 1 ⁼ ° 15 " ^C CH ₂ - E ₂ = Hydrogen, OH -CH ₂ - E ₁ = O ₁₅ - c CH ₂ H ₂ = -C ₂ H ₄ OH, ^E 5 ⁼ -CH ₂ - - ^E 1 ⁼ CH-
I. = -CH ₀ -CH- 5 -CH ₂ -

CH,

J ₅ = - CH ₂ -CH ₂ -

" ⁰ 21 ' ^E 2 ^{= hydrogen} »

CH, OH

B ₁ = .- CH-CH-CH, CH,

-C

₁ cj

N / A/

Na / ^ AA

K / DAA

atrium dodecyl sulfate

N / A

Annotation; "Q? AA - triethanolamine; DÄA - diethanolamine, MAA - monoethanolamine

- ^: - ■■ '- ^: · - ^: - "- ■■ · -' 3345873 - 30 -

:. ■ Table 1 (cont.)

j 8 2 IQ H

8 x 200 'x 185 180 0.97

COPY

_31- '

⁵ Table 2.

Washing power according to the 'standard wool fabric with a Concentration of the masses of the invention; Connections from 0.25 mass percent. "· ■

ITr; of the double salts of amine and alkali metal cations the azylamidoalkylene (or azylamido- -N-hydroxyalky1-N-alkylene) sulfosuccinic aure

, E ₂ = hydrogen,

E ₃ = -CH ₂ - CH ₂ - S, • OH ^E 1 =
Ej = C ₁₃ -C ₁₉ , R ₂ '■ = -C ₂ H ₄ O
-CH ₂ -CH ₂ - • CH -
t
CH, -
3 V
^E 3 ⁼ C ₁₅ - C ₁₉ , R ₂ = -CH ₂ -
-CH ₀ - CH-
^ I
CH,
3 - ^E 1 =
^E 5 ⁼
E ₁ = Cc C ₁₅ - C ₁₉ , E ₂ = -CH ₃ ,
-CH ₂ - CH ₂ -
JC ₁ P ₇ , E ₂ = hydrogen, *>
ν-
X) - C ■ CH ₂ -CH ₂ - ^E 5 = Ί7? 1 'P "~" assersTjOi
-CH ₂ - CH ₂ -. j ^E 1 ^{= 0} 1
E ₃ = - 5 "C ₁ 9» R ₂ = -CH-CH-CH ^,
CH, OH
- CH-CH-
CH, CH,
3 3

jcc ITa / TÄA

lia / TÄA

Sodium dodecyl sulfate · Na

Notes; . TÄl - triethanolamine; DÄA - diethanolamine, MÄA - mono'athanolamine

COPY
BATH ORIGINAL. - ..

-52 -

Table 2 (cont.)

Detergency preservation of the

Whites

5 90 6th 92 7th 95 8th • 96

95 98

96 .98 96. 98

98

98 98

97 98

96; 98

-33-

Table 5

Surface tension of the aqueous? Solution, determined stalagmometrisch (in N / m "OK" ~ -0 ^ at a temperature of 20 ⁰ C and a concentration of the compounds of 0.1 percent by mass

■■ (■ -

The double salts of amine and alia-

In limetall, the azylamidoalkylene

f_ · "" ·, _ (or azylamido-N-hydroxyälkyl-

spiexs ^^ _a lkylen) -sulf © succinic acid

^R 2 ⁼ hydrogen,

- CHp * "

^ r-C ^ jη,

, R ₂ = -CH ₂ -CH - OH,

-CH ₀ - CH-ι

CH,

R ₂ = = -CH ₂ - CH ₂ -

^{= σ} 9 "" ^σ ΐ7 * ⁵ 2 ^{= water fcoff} »
= -CH ₂ - CH ₂ -

C ₁₇ -

, R ₂ = hydrogen,

-CH ₂ - CH ₂ -

R ₂ =

-CH
CH

R, = -CH -

CH - CH

OH

CH-

C ¹ H, 5

Cations

3 ^ 66 ^ DAA

Na / a & A

Na / TÄA

, R ₂ = -CH ₂ - CH ^.,.

, ⁼ —CHp - CHp—

Note above A - triethanolamine, PAA -diethanolamine, MAA - monoethanolamine

1 30.0 2 .28.4 3 28.1

Table 5 (cont.)

Distilled hard water

Water '(5.55 mVal / l)

. 31.3 29.2

28.5

4 x 30.2. 30.8

5 30.4. 31.6

6 30.6 30.8

7 28.2 29.0

8 29.8 30.9 ■ '

COPY

_ 35-

Table 4

Serial
No. · Characteristic values the laundry detergent ■ 10 number
play of At- \ $ 3 11 12th 6th 1 2 4th

Foaming of the

0.25% solution of the compounds according to the invention. _H ■ fertilize at 4O ⁰ C after ^

Ross-Miles, mm 205
186

180

201

184

198 174

196 176

178 171 173

Foam off i Ii t "at

.. cloud point ', ⁰ C

Degreasing effect on sodium lauryl sulfate, %

Viscosity at 20 ^° C., MPa »ß

0.97 0.97 0.98 0.9S -2-5 1 -r 2 2 -3 -1 ■ *

56.3. -51.5 5 ^, 2

32.0 3, o 1200p 430,

6 Density at 20 ⁰ C, kg / m ⁵ 1.098 1.008 1.072 1.0;

pH of the 10% aqueous solution of the ■ compounds according to the invention

6.80 6.85 6.75 6.8

COPY

Double salts, of arain and alkali metal of the acylamidoalkylene ( or Azylaraido-N-hydroxyalkyl - N-alkylene) sulfosuccinic acid, Process for their production and use

Claims (8)

FON-ER EBBINGHAUS FINCf PATENT LAWYERS EUROPEAN PATENT ATTORNEYS MARIAHILFPLATZ 2 & 3.MÖNCHEN 9O POST ADDRESS: POSTFACH 95 O1 6O, D-8OOO MUNICH 95 Institute Chimii Akademii Nauk Estonskoj SSR Oporno-pokazatelnyj ryboloveckij kolchoz imeni S.M. Kirova DEAA-31547.9 December 19, 1983 DOUBLE SALTS OF AMEN AND ALKALIMETAL OF THE ALKYLENE (ODEr AZYLAiJIDO-N-HYDROXYALKYL-N-ALKYIEN) -Sü LFOBEHNSOEIHSSUHB, PROCEDURE FOR THEIR Hh / RS ELLUNG AND USE Claims Double salts of amine and alkali metal of the azylamidoalkylene (or Azylamido-N-hydroxyalkyl-N-alkylene) sulfosernsteinsatire the general formula I C - N - R _Q - O - C - CH ₀ - CH ¹ HI ³ Il \ 0 R MeK ■ in what for a (Baus stands, ) - & ohlenwasserst: oifrest linear , -CH ,, -CH ₂ - CH ,, -CH ₂ -CH ₂ -OH, -CH ₂ -CH -OH d or CH -CH - CH - CH ^ means, OH OH R, represents -CH ₂ - CH ₂ -, -CH ₂ -CH - or -CH - CH -, OH? OH-j · CH ^, R ₄ , Rc, R _{6 represent} H and / or -CH ₂ -CH ₂ - OH, Me is Na or K. BATH 2. A process for the preparation of the double salts of amine and alkali metal of the azylamidoalkylene (or azylamido-N-hydroixyalkyl-IT-alkylene) sulfosuccinic acid according to claim 1, characterized in that I η et that fatty acids and glycerides containing fatty acids and glycerides in the plants Waste water from the fish processing industry with an acid number of at most 50 mg KOB / g, a saponification number of 181 to 192 mg KOH / g and a bromine number of 60 to 70 mg Br / 100 g, treated with boiling methanol in the presence of sulfuric acid and a reaction mixture obtained from the one which consists of the GIyzeriden and Methylestern the! fatty fat layer is separated off, this is in the presence of sulfuric acid at a temperature of 50 to 60 ⁰ C with methanol laundry and a reaction mass is obtained from which it is an anhydrous fat layer is separated and this is treated in the presence of alkali .with methanol at the boiling point of methanol ... and a reaction is obtained, the methyl contains ster of fatty acids, which are separated off "and with alkylolamine, which in an amount of 25 to 55 percent by weight, based on! the amount of the methyl ester of the fatty acids is taken in the presence of a catalyst selected from alkali metal or its amide or alcoholate, ^{treated at a temperature of 70 to 90 0} C and alkylolamides of the fatty acids obtained, which are obtained with maleic anhydride at a temperature of 60 to 90 ⁰ C treated and receives alkylolamide maleates of the fatty acids and then treated them with sodium or potassium pyrosulfite and 'ethariolamine or ammonia at a temperature of 60 to 90 ⁰ C in an aqueous medium » 3 · The method according to claim 2, d u r c h marked that one for the purpose of an improvement the quality of the end product, the methyl esters of the fatty acids before said treatment of the same with alkylolamine in the presence of the mentioned catalyst with alkylolamine, which in an amount of 5 to 10 percent by weight, based on the weight of the methyl ester ~ BATHROOM Fatty acids, taken, pretreated at a temperature of 70 to 80 ⁰ C and then removed the consumed alkylolamine · ■ 4- · Method according to one of claims · 2-3, characterized marked as Alkylolamine monoethanolamine, diethanolamine, diisopropanolamine, N-methylethanolamine, N-ethylethanolamine or Dibutanolamine used. 5 «method according to one of claims 2-4,. through this marked that one for the purpose of simplifying the technology of the process sodium-2-aminoethoxylate used as catalyst 6 · The method according to any one of claims 2-5, characterized marked as jlthanolamine mono-, di- and / or eriethanolamine is used. 7 · Detergent, -which has a surfactant Contains a substance, an odor improver and water, characterized in that it a double salt of thiethanolamine as a surface-active substance and sodium of acylamidoethylene sulfosuccinic acid the following formula 0 0 RC-NH- CH ₂ - CH ₂ - 0 - C - CH ₂ - CH - SO ₃ Na wherein R is a (C ^ ₁ - - ^C 2 "P -hydrocarbon radical according to claim 1, with the following ratio of the named- th components contains; The double salt of iriethanolamine and sodium Acylamidoethylsulfinic acid 5-0 to 52% by mass. . Odor improvers ... 0.1 to 1.5 percent by weight . Water everything else. . 8. Detergent according to claim 7 »characterized in that it additionally contains diethanolamide of the (Cq- C ^ ₁ -,) - fatty acids, sodium chloride and ethyl alcohol with the following ratio of the components: Double salt of triethanolamine and sodium of azylamidoethylene sulfosuccinic acid ... 12.0 to 20.0 mass percent " Diethanolamide of the (Cg- C ^ » ) -fatty acids 0.5 to 5.5 percent by weight Sodium chloride 1.0. up to 3 * 5 percent by mass Ethyl alcohol 0.5 to 1.5 percent by mass odor improver 0.1 to 1.5 percent by mass ■ Water everything else.