DD225990A1 - PROCESS FOR THE PREPARATION OF NEW 2,3-DISULFOPROPYLAMMONIUM BEVERES - Google Patents

Abstract

The invention relates to a process for the vicinal difunctionalization of allylammonium salts of the general formula II to the hitherto unknown 2,3-disulfopropyl-ammonium betaines of the general formula I, which can be used as valuable surfactants, when R3 is a longer-chain alkyl radical. To prepare the new 2,3-disulfopropyl-ammoniumbetaine trialkylallylammonium be reacted with two molar equivalents of a bisulfite and one molar equivalent of a peroxodisulfate in the p H range 2 to 4 to implement. Instead of peroxodisulfate alone, combinations of peroxodisulfates with customary oxidizing agents, eg. As hydrogen peroxide or chlorine-emitting substances are used. In reaction times of a few minutes, the new compounds I can be displayed in quantitative yield. Formulas I and II

Description

Title of the invention

Process for the preparation of novel 2,3-disulfopropylammonium betaines

-Ause of the invention

The invention relates to a process for the preparation of novel 2,3-disulfopropyl-ammonium betaines of the general formula I, _1st

R ³ - N ⁺ - CH ₂ - CH - GH ₂ - SO ₃ "I

^f 2 ^} -

^R SO ₃

in which

1 2 R and R independently of one another can be hydrogen, alkyl radicals having 1 to 3 C atoms , hydroxyalkyl radicals, oxyalky radicals having up to 10 ethylene oxide units or ring-closed substituents, and

3 R is hydrogen or an alkyl radical having 1 to 22 carbon atoms, which groups may -h'H-CO- or -CO-NH-contained in aer chain,

means.

Products having the structure I can be used as surfactants effective in a broad pH range,

Characteristic of the known technical solutions

Sulfobetaine sulfonates having nonvicinic sulfonic acid groups can be obtained in two ways by reacting either hydroxyethyl amino compounds with two moles of propane sultone (F. D, Smith and WM Linfield, 3. Ainer / Oil Chemists Soc. 55 (1978), 741), or triallyl or Tetraallylammoniumsaize in the pH range 5 to 8 simultaneously with salts of sulfurous acid and an oxidizing agent, for example, atmospheric oxygen »are reacted (DD-WP 200 733).

The disadvantages of these known processes are that in the first case the extremely carcinogenic propane sultone must be used and handled with great care, in the second case the use of allyl ammonium compounds with more than two allyl substituents is required. that forcibly with the SO group and a further hydrocarbon radical must be introduced.

Reaction products of unsaturated aliphatic compounds with hydrogen sulfites have been described very different structures. Be simple olefins is carried out, a radical Difunctionalization _t when reacted to 9 hydrogensulfites under the influence of organic peroxides or air in the pH range 4 * In long reaction times of one to several hours, in the heat products having a terminal sulfonic acid group and adjacent sulfinate group as probable, but unproven structure obtained (DE-PS 11 17 565). Under similar conditions, isosulfonates were obtained from Ally! Ammonium salts after very long reaction times (3rd. Am. Oil Chemists Soc. 53 (1976), SO). From US-PS 4,267,123 (Examples 1 and 5) discloses that in the case of oxygen-induced Allylheteroverbindungen propanesulfonate Hydrogensulfitaddition (-CH CH CH-SQ ~) adjacent Propylsulfiten (-CH ₂ CH ₂ CH ₂ -O-SO ₂ " In contrast, DD-PS 154 443 quantitatively dissolves hydrogen sulfites to allylaramoic acid, with the propylsulfites being the main product of the reaction.

niura salts to form uniform 3-sulfopropyl-arginium betaines (sulfobetaines) when the oxygen-induced reaction is catalyzed by transition metal ions *

Object of the invention

It is the object of the invention to functionalize the double bond in allylic ammonia salts in a simple reaction with 2 sulfonate groups. «

Explanation of the essence of the invention

The object of the invention is to make a _# Difunctionalization the Allylammoniumgruppe ^ arise formula purely in the new sulfobetaines with an additional vicinal sulfonic acid in good yield.

The object is achieved in that, according to the invention, solutions of allyl ammonium salts of the general formula II,

R ¹

3 U

RN ⁺ - CH ₂ - CH a CH ₂ X II

in the

12 3 R, R and R have the abovementioned meanings and

X represents an anion, preferably chloride or broride ,

in the pH range 2 to 4 with hydrogen sulfite and peroxodisulfate in the molar ratio 1: 2: 1 to 2-sulfonato-3-sulfopropyl

1 ' 2. ammonium betaines of the general formula I, in which R, R

3 and R have the meanings given above,

R ¹

- CH ₂ - CH ₂ CH ₂ + 2 HSO ₃

pH 2 ο ^f ₊

L , ψ R ^J - N - CH_ - CH - CH_ - SO »

^R SO ₃

H-X + 2 HSO, 4

The reaction initiated by this procedure differs fundamentally in the course and end product from all hydrogen sulfite additions carried out so far on Ally! Compounds: In the short reaction time of a few minutes, complete conversion yields exclusively 2,3-disulfopropyl-ammoniumbetaine I by difunctionalization of the double bond; In the absence of allylic compounds, peroxodisulfates react with bisulfites to form sulfates in a well-known rapid redox reaction, so that allyl double bonds could not be expected to undergo quantitative vicinal difunctionalization with high selectivity and yield were subject. It is also a surprising finding that the reaction is specifically bound to the presence of peroxodisulfates. "Other per compounds, for example, hydrogen peroxide or alkali perborates, do not induce a comparable reaction but only oxidize sulfite to sulfate. However, it is possible in certain cases to use peroxodisulfates and other peroxygenating compounds or even other oxidizing agents, in such a way that less than the molar amount of perfluoroacetate per mole of allyl compound is required. z, B, hydrogen peroxide, chlorine, chlorates, brorate and a # m # are suitable for this purpose.

The process according to the invention is preferably carried out in such a way that roan in aqueous solution mixes the allylammonium salts with the two molar amount of bisulphite, sets the pH to 2 to a maximum of 4, and adds the peroxodisulphate in a monolar amount with stirring, the progressing reaction being long-chain substituted allylammonium salts give sulfobetaine sulfonates with surfactant properties which precipitate out of the reaction mixture in the procedure described and can be easily isolated and recovered in pure Fora the work-up neutralized the resulting sulfuric acid and the suifobetainsulfonate separated if necessary from the inorganic salt content.

A continuous implementation of the method according to the invention is possible in a suitable apparatus if the components are metered in the stated molar ratio at the beginning of a residence time zone,

embodiments

13 The C-NMR spectra listed in the following examples were measured in D ^ O, TMS was used as the external standard. The numbers on the C atom symbols of the structural formulas correspond to the chemical shifts in ppm,

example 1

Sodium dimethy1-2,3-cisulfopropyl-araraoniumbetain

12 3

(R = R = CH ₃ ; R = H in the general formula I) from dimethyl ethylamine hydrochloride

310 g (1 mol) of 39.2 % aqueous Diraethylallylaminhydrochloridchlorid, 533.6 g (2 mol) of 39 % ge technical sodium hydrogen sulfite solution with an iron content of 9 mg / mol. In a equipped with stirrer, reflux condenser, dropping funnel and thermometer Solution as well as 30 g of 37 % xge, hydrochloric acid together to form a homogeneous

Solution whose pH was 2.15 (glass electrode). A pale yellow starting solution prepared in this way was rapidly added to a 40% strength aqueous sodium peroxodisulfate solution which had been prepared from 238.1 g (1 folole) of sodium peroxodisulfate (Na ₂ SO 3) and 357.15 g of water. After 2 hours, approximately 6 p % of these were present Solution was added and the red-colored solution had warmed from 21 to 94 ^° C. The addition of the oxidizing agent continued, the reaction solution becoming increasingly brighter and finally becoming colorless after about 50 % of the peroxodisulfate solution had been added boiling solution could easily be removed by evaporative cooling, so that after 4 minutes, the metered addition of Peroxodisulfatlösxing was completed *

The following overview shows the time course of the exothermic reaction during the metered addition phase of the oxidizing agent:

Time (min) 0 0.5 1 2 3 4 5

Temp, ( ⁰ C) 21 60 75 94 103 103 101

1 An H-NMR spectrum prepared by the solution at that time confirmed the quantitative and selective conversion of the allyl ammonium salt into the sulfofetate sulfonate. After neutralization of the strongly acidic reaction solution with 33 % sodium hydroxide solution, the iron salt contained therein by the use of technical grade bisulfite solution flocced as iron -III-hydroxide and could be filtered off together with most of the crystallized sodium sulfate,

13 The colorless filtrate showed the following C-NMR spectrum:

(the N-CH ₃ groups are not equivalent) 47.0 / 44.7 59.6 53.3 50.6

(H ₃ C) ₂ N ⁺ - CH - CH - CH H _f ,

SO ₃ "SO ₃ " Na ⁺

If the SuIfobetainsulfonat completely separated from its inorganic accompanying salts and the free dimethyl- (2-sulphonic acid) -3-sulfopropyl-ammonium betaine are isolated, one may proceed as follows: After concentration Oer obtained above reaction solution to dryness, the residue obtained is mixed with sufficient Concentrated hydrochloric acid and worked through him, filtered from the undissolved sodium salts and the hydrochloric acid solution of sulfonated sulfonic acid under reduced pressure to dryness .. Soon after, the sulfonic acid begins to crystallize as a white substance. The sulphonic acid, which begins to decompose slowly from 120 ^° C., can easily be recrystallised from water. "

13

The C-NMR spectrum of this acid is identical to that of the corresponding sodium salt *

By neutralization of the sulfonic acid with any bases, the particular salts (sulfobetainesulfonates or disulfonates) formelrain can be obtained in case of need. With 2 molar equivalents of sodium hydroxide, for example, disodium 3-dimethylaminopropan-l, 2-disulfonate with the following

C NMR spectrum available:

46.7 51.1 (H ₃ C) ₂ N - CH ₂

Example 2

Sodium trimethyi- _2f 3-disulfopropyl ammonium betaine

12 3 (R = R = R = CH in the general formula I) from Triaethylallylammoηiumchlorid

The procedure was as described in detail in Example 1, 341.6 g (1 mol) of 39.7 % xge Trimethylallylammoniumchloridlösung, 533 _f S g (2 mol) of 39 % ± ge sodium bisulfite solution and 33 g of 37 % ± hydrochloric acid ge to a homogeneous solution whose pH was 2.0. To this solution

56 7 52 ί 2 - CH CH 2 f 1 ^S0 3 N / A SO 3 N / A

595.25 g of 40% sodium peroxodisulfate solution were added dropwise over the course of 5 minutes. "The following overview should clarify the time course of the exothermic reaction during the metered addition phase of the oxidizing agent:

Time (min) 0 0,5 1,5 4 5 Temp «( ⁰ C) 22 40 60 85 90

The conversion to sulfobutanesulfonate was quantitative and selective at this time, as determined by H-NMR spectroscopy. "

C-NMR spectrum of the neutralized reaction solution:

56.1 67.5 53.5 52.7 (H "C)" N ⁺ - CH ₀ - CH - ₀ .CH

SO "S0 ₃ ~ Na ⁺

However, if the pH of the homogeneous reaction solution initially set to values > 2, the selectivity of the ongoing reaction decreases, which is in increasing iMaSe in addition to triraethyl ^ s-disulfopropyl-ammoniumbstain also trimethyl-3-sulfopropyl-ammoniufflbetain formed eventually become the main product of the implementation.

This fact should be demonstrated by the following example:

Example 3

The procedure of Example 2 was followed by mixing 1 mole of trimethylallyl ammonium chloride solution with 2 moles of sodium bisulfite solution. As described above, 1 mol of a 40% strength sodium peroxodisulfate solution was added to the homogeneous solution of pH 4.0. The quantitative composition of the neutralized reaction solution was determined by

Comparison of the intensities of suitable signals determined by H-NMR spectroscopy and revealed that in addition to 59 % of trimethyl-2,3-disulfopropyl-ammonium betaine, 41 % of trimethyl-3-sulfopropyl-ammoniurabaine are obtained (see DD-WP 154 443),

Example 4

This and the following example are intended to illustrate the suitability of oxidizer combinations.

The procedure was as in Examples 1 and 2, and a homogeneous solution of pH 2.0 was prepared from 1 mol of trimethylaluminum ammonium chloride solution, 2 mol of sodium bisulfite solution and hydrochloric acid and first 15 mol% of a 50% vimmonium peroxo was added in about 1.5 minutes 'Sulfate solution and then added 85 mol-> 30% hydrogen peroxide at such a rate that the exothermic reaction could be controlled by boiling cooling, which took about 4 minutes.

 '' H NMR spectroscopy showed that the illylammonium salt had been quantitatively converted to the sulfo betaine sulfonate.

The repetition of this experiment exclusively with hydrogen peroxide as the oxidant resulted in addition to unchanged starting material only to an oxidation of sulfite to sulfate.

Example 5

The procedure was as in Example 4 and instead of 85 MoI? Hydrogen peroxide as oxidant chlorine,

Only sulfobetainesulfonate could be detected by H NMR spectroscopy, but no sulfobetainesulfonate could be obtained by repeating the experiment exclusively with chlorine as the oxidant. Only the oxidation of sulfite to sulfate took place.

Example 6

Sodium diethy1-2 , 3-disulfop ropy1-amraonium betaine

(R ¹ = R ² = -CH; R = Hin of general formula I) from diethylallylaraine hydrochloride

A homogeneous solution was prepared from 1 mol of diethyiallylamine hydrochloride, 1 mol of sodium metabisulfite (Na S OJ

tL £ - O

and 37 % hydrochloric acid according to the method of the above Examples.

When the starting pH value was set to 2.0, the amount of sulfobutylene suifonate was quantitatively maintained »

13 -

C NMR spectrum (the N-butyl groups are not equivalent):

10.2 / 9.3 51.0 / 49.7 53.5 53.1 50.7

(CH "- CH-UN * - CH. - CH - CH"

SO ₃ "SO ₃ Na ⁺

The isolation of the diethyl (2-sulfonic acid) -3-sulfopropylammoniumbetains can be carried out according to the procedure described in Example 1. Sulfonic acid was first obtained as a highly viscous, 'colorless ul, which crystallized after several days of standing, but more quickly after inoculation.'

13

The 13 C NMR spectrum is virtually identical to that of the sodium salt. "

By neutralization of sulfobetainesulfonic acid or sulfobetainesulfonate with sodium hydroxide solution, the disodium-3-

13 diethylaminopropane-1,2-disulptonate with the following C-NMR spectra available:

11,6 48,2 57 54,9 52 _t 4 - CH ₂ ) ₂ N - CH ₂ - CH - CH ₂

SO ^ Na SO ^ Na

Example 7

Nat rium-t riethy 1-2,3-disulfopropyl-arnmoniumbetain (R- ¹ · = R = R = C * _O H "in the general formula I) from Triethylallylammoπiumbromid

Han prepared a homogeneous solution of pH 2.0 from 1 mole of triethylallylammonium tribromide, 2 moles of sodium bisulfite, and hydrochloric acid and proceeded to one of the preceding examples. "The sulfofatty acid sulfonate was quantified.

13 and showed the following C-NMR spectrum;

8.8 55.4 59.5 53.3 53

(CH - CH ") N ⁺ - CH ^ - CH - CH, 3 * 3. ^ yy -

SO ₃ "SO ₃ " Na ⁺

Example 8 ·

Nat rium-2,3-disulfop ropy1-ammoηiumbetain

12 3 (R = R = R = H in the general formula I) from allylamine hydrochloride

A homogeneous solution of pH 2.0 was prepared from 1 mol of allylamine, 2 mol of sodium hydrogensulfite and hydrochloric acid and was subjected to Example 4 *.

After neutralization and filtration of the insoluble iron (III) hydroxide present in traces, the sulfobatainsulfonate immediately began to crystallize from the cooled, colorless reaction solution. By adding ethanol, a quantitative crystallization can be achieved. The product can be easily recrystallised from water. " ¹³ C-NMR spectrum:

40.5 55.1 50 _f 4

C 5

HN ⁺ - CH - CH - CH ^{3 ά}

SO ₃ SO ₃ "Na ^T

The free (2-sulfonic acid) -3-sulfopropyl-ammonium betaine can be isolated by the procedure described in Example 1. It is obtained a colorless crystalline substance, which is also slightly water with the addition of ethanol

13 can be recrystallised »The C-NMR spectrum of the free sulfonic acid is virtually identical to that of the sulfobetaine sulfonate *

By neutralization of the sulfobetaine sulfonic acid or the sulfobetaine sulfonate with sodium hydroxide solution, the disodium 3-

13 aroinopropane-1 _f 2-disulfonate with the following C-NMR spectrum available:

42.3 60.0 50.3

HN - CH - CH - CH ₂

I-!

SO ₃ Na SO ₃ Na

Examples 9 to 13

Sodium alkyl-dimethyl-2,3-disulfophenyl aminobium betaines (R ¹ = R ² = CH ₃ ; R ³ = alkyl in the general formula I) from alkyl dimethylallyl ammonium salts

Alkyl -N ⁺ - CH - CH- CH

CH ₃ - SO ₃ - SO ₃ "

The procedure of one of the examples described above was followed, producing a homogeneous solution of pH 2.0 from 1 mole of alkyl dimethylallyl ammonium salts, 2 moles of hydrogen sulphite, hydrochloric acid and water. In the case of longer-chain alkyl dimethyl-aliy! Ammonium salts (alkyl "C ^ ₄₎ the initial suspension had to be heated to about 40 ⁰ C so that a homogeneous starting solution.

After the reaction with 1 mol of a peroxodisulfate or a peroxodisulfate / Oxydationsmittel-Korabination fal

In particular, the longer-chain reaction products (alkyl &. G ^) are precipitated from the cooling solution. Depending on whether the reaction mixture was previously neutralized, either the free sulfobetainesulfonic acids or the corresponding sulfobetainesulfonates could be separated off.

In the case of the shorter-chain sulfobetaine sulfonates, these were separated from the inorganic accompanying salts by extraction of the residue of their evaporated solutions with an ethanol / water mixture (1: Λ or 2: 1) «

Tab. 1: Sodium-alkyl-dimethyl-2,3-disulfopropyl-ammoniumbetaine

Decomposition point (C)

> 196

> 204

  > 226

example R (n-vinyl) 9 ^G 10 ^H 21 10 ^C 12 ^H 25 11 ^C 14 ^H 29 12 ^C 1S ^H 33 ^{/ C} 18 ^H 37 13 ^C 13 ^H 37

> 165

+) The free acid melts with decomposition at 162 ⁰ C

Example 14

Sodium aminocarbonylmethyl-di-ethyl-2,3-disulfopropyl

amraoniumbetain

(R ¹ = R ² = CH ₃ ; R ³ = CH ₂ - CO - NH ₂ in the general

Formula 1)

The procedure of Example 4 was repeated and the homogeneous solution of pH 2.0 from 1 mol of aminocarbonylmethyldimethylallylammonium chloride prepared from dimethylallylamine and chloroacetamide, 2 moles of sodium hydrogensulfite and hydrochloric acid was reacted with ammonium peroxodisulfate / hydrogen peroxide using external cooling an operating temperature of 60 C was not exceeded. After the reaction was immediately neutralized with sodium hydroxide solution.

to avoid hydrolysis of the acid amide function.

However, if you want to implement analogously to Example 1 only with peroxodisulfate, after about 10 MoI-Jb the peroxodisulfate have been added to the allyl ammonium, at least the two-molar amount of sodium hydroxide while maintaining a temperature around 60 C added simultaneously with the remaining peroxodisulfate (90 mol%) become.

The obtained sulfobetaine could be separated from the inorganic accompanying salts by extracting the residue of the evaporated reaction solution with an ethanol / water mixture (1: 1).

The Sulfobetainsulfonat obtained in almost quantitative yield with a decomposition point of > 275 ⁰ C showed the

13 following C-NMR spectrum:

158.3 55.3 54.2 / 54.7 66.5 53.3 52.6 HN - CO - CH "- N ⁺ (CH) - CH, - CH - CH

i J

SO ₃ "SO ₃ " Na ⁺

Example delete

Natriurododecyl / tetradecylaminocarbonylmethyi-dimethyl-2,3-disulfopropyl-aflifflonium betaine

(R ¹ = R ² = CH ₃ , R ³ = CH ₂ -CO-NH- ^C ₁₂ ^H 25 ^{/ C} 14 ^H 29 ^{in the} general formula I)

^G 12 ^ 25 ^{/ C} 14 ^H 29 " ^HN " ^C0 " ^CH 2" ^{N +} ( ^CH ₃ ) ₂ " ^CH 2" ^CH " ^CH ₂

I t

SO ₃ "SO ₃ ^- Na ⁺

Repeating 3eispiel 14 and sat dodecyl / tetradecylafninocarbonylmethyl-dimethyl-allylammonium chloride which one of Dirnethylally lam in, Chloressigsäuremethylester and dodecyl / tetradscylamin mixture (cocoamine, Koraponentenverhältnis about 1: 1) produced quantitatively to SuIfobetainsulfonat a melting point of 158 ⁰ C (dec *) Ura. The extraction

of the sulfofetamine sulfonate was carried out from the residue of the evaporated solution by aqueous ethanol (70%),

Example 16

Natriura-di (dodecyl / tetradecylaminocarbonyl) methyl-diniethyl-2,3-disulfopropyl-aramoniumbetain

(R ¹ = R ² = CH ₃ ; R ³ = CH (CO-NH- ^C i ₂ ^H ₂ 5 ^{/ C} 14 ^H 29 ⁾ 2 ^{in deP} general formula I)

^G 12 ^H 2 ₅ / ^C 14 ^H 29 - ^NH * ^C °) ₂ ^CH - ^N < ^CH 3> 2 ' ^CH 2 "f ~ f2

SO J "SO" Na ⁺

Han proceeded as described in Example 14 and prepared di (dodecyl / tetradecylaminocarbonyl) me thyl-dimethy1-allylaramonium bromide prepared from dimethylallylamine, diethyl bromomalonate and dodecyl / tetra-decylamine mixture (cocosarain, component ratio about 1: 1) at a reaction temperature of 40 C quantitatively to the sulfofetamine sulfonate. Upon cooling of the reaction mixture, the sulfonate thus produced precipitates; it was separated and recrystallized from ethanol. It has a melting point of 155 ⁰ C (Zers.).

Example 17

Sodium octanoylamidoethyl-diraethyl ^ .S-disulfopropyl-

ammonium betaine 1 2

general formula 1)

= R ² = CH ,,; R ³ = CH - CH. - NH - CO - 0 - H ^ in the

C ₇ H ₁₅ - CO - NH - CH ₂ --CH ₂ - N ⁺ (CH ₃ ) - Cn - CH - CH ₃

SO ₃ "SO ₃ " Na ⁺

The procedure of Example 14 was repeated and the amount of octanoyl-alaidoethyldimethyl-allylamonium chloride prepared from methyl octanoate, dimethylethylenediamine and allyl chloride was quantitatively converted to the corresponding sulfofetate sulfonate of the 2-mer.

> 186 C (recrystallized from 70% strength aqueous ethanol) »

Example 18

Sodium pentadecafluorooetanoylamidoethy1-diraethy1-2,3-disulfopropyl-ammoniurobetain

(R ¹ = R ² = CH ₃ ; R ³ = CH ₂ --CH ₂ --NH - CO - C ₇ F ₁₅ in the

general formula I)

C ₇ F ₁₅ -CO-NH-CH ₂ -CH ₂ -N ⁺ (CH ₃ J ₂ -CH ₃ -CH-CH ₃

SO ₃ "SO ₃ " Na

The procedure of Example 14 was repeated and Pentadecafluorooctanoylamidoethyl-dimethyl-allylammoniumchlorid, which was prepared from Pentadecafluorooctansäurechlorid, dimethylethylenediamine and allyl chloride produced "quantitatively to 'crystalline Suifobetainsulfonat of melting point 243 C (Zers #), uracurristisiert from 70% aqueous ethanol.

Claims (4)

invention claim 1 2
R and R independently of one another are hydrogen, alkyl radicals having 1 to 3 C atoms, hydroxyalkyl radicals, oxyalkylene radicals or substituents closed to the ring, R is hydrogen or alkyl radicals having 1 to 22 carbon atoms, whose chain may also contain the groups -NH-CO- or -CO-NH-, and M a cation mean, characterized in that allyl ammonium salts of the general formula II having the abovementioned meaning of the substituents and in which X is an anion, preferably chloride or bromide, in the presence of twice the molar amount of a hydrogen sulfite with peroxodisulfate alone or a combination of peroxodisulfate and others Oxidizing agents are reacted at pH values of 2 to 4, in such a way that per mole of allyl ammonium salt 1 mol peroxodisulfate or - in the presence of other oxidants - a total of 2 Oxydationsäquivalente are available. 1. A process for the preparation of novel 2,3-disulfopropylammonium betaines of the general formula I, R ³ - N ⁺ - CH - - CH - CH - SO - M ⁺ ι ² ι ³ R ² SO ₃ - R ¹
R ³ _N ⁺ - CH - CH, = CH X " II in which 2, process according to item 1, characterized in that the oxidizing agents used in the mixture with peroxodisulfates are chlorine or chlorine-releasing substances, chlorate, bromine, bromates or hydrogen peroxide * 3, method according to item 1, characterized in that the cation is M ⁺ Na ⁺ , K ⁺ , NH ₄ ⁺ or H ^., 4 * Method according to item 1, characterized in that are used as AHylammoniümsalze Chloride _t bromides, iiethosulfate or sulfates.