CH676183B5 - - Google Patents

Abstract

Sulphomethylated amino-esters which are the reaction products of an alcanolamine of formula I HO-R4-NHR1 I where R1 is hydrogen, C1-4alkyl, -R5-OH or &lparstr& CH2 &rparstr& n NR2R3 R2 and R3 are, independently, hydrogen, -R5-OH or C1-4alkyl R4 and R5 are, independently, 1,2-ethylene or 1,2-propylene and n is 2 or 3 or a mixture thereof, with a fatty acid of formula II R-COOH II where R is optionally hydroxy substituted C11-21alkyl and/or alkenyl, the product amino-esters being sulphomethylated with, e.g., formaldehyde or a formaldehyde-yielding compound and a sulphite, SO2 or a compound of formula V HO-CH2-SO3M V where M is H or a cation, are useful as non permanent finishing agents for fibrous materials, particularly as softening agents for cellulosic materials.

Description

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description

The invention relates to sulfomethylation products of certain amino esters, their production and their use for the treatment of fiber material, in particular textile material, and the corresponding preparations which contain these sulfomethylation products.

A first subject of the invention is therefore sulfomethylation products of amino esters from alkanolamines of the formula

HO-alkylem-NHRi (l),

wherein Ri is hydrogen, Ci_4-alkyl, -alkylene2-OH or -4CH2 * | i-NR2R3>

FÌ2 is hydrogen, alkylenez-OH or Ci - ^ - alkyl,

FÌ3 is hydrogen, alkylene2-OH or Ci_4-alkyl,

Aikylem and alkylene2 each 1,2-ethylene or 1,2-propylene,

and n 2 or 3

mean, and fatty acids of the formula R-COOH (II),

wherein R is optionally Cn-21 alkyl or alkenyl containing hydroxyl groups, or functional derivatives thereof.

The alkyl radicals R 1, R 2 and R 3 preferably contain 1 or 2 carbon atoms, methyl being particularly preferred. Alkyleni and Alkylen2 each preferably represent ethylene-1,2. Ri is advantageously hydrogen or -alkylene2-OH, preferably hydrogen or β-hydroxyethyl.

The alkyl or alkenyl radical R can be unsubstituted or optionally carry a hydroxyl group (such as in hydroxystearic acid or in ricinoleic acid) and can be linear or branched; the radical R is preferably free of hydroxyl groups. Preferred acids of the formula (II) are conventional fatty acids with 14-22 carbon atoms, in particular with 16-22 carbon atoms. Individual representatives of this group of acids that are worth mentioning are: lauric acid, myristic acid, palmitic acid, iso-palmitic acid, stearic acid, isostearic acid, hydroxystearic acid, oleic acid, arachic acid and behenic acid, and corresponding mixtures, in particular technical mixtures, e.g. Tallow fatty acid, coconut fatty acid, isostearic acid and mixtures of n-stearic acid and isostearic acid. The saturated, aliphatic fatty acids, in particular stearic acid and isostearic acid, are particularly preferred. Isostearic acid is understood here to mean a technical mixture of isomers, e.g. in US Pat. No. 2,812,342 or in Kirk-Othmer “Encyklopedia of Chemical Technology”, 3rd edition, vol. 4, page 862. A similar mixture is isopalmitic acid.

Particularly preferred amino esters are the esterification products of the preferred fatty acids mentioned above with monoethanolamine and / or in particular with diethanolamine; especially the esterification products from diethanolamine and stearic acid or mixtures of stearic acid / isostearic acid (the latter advantageously in the weight ratio of stearic acid to isostearic acid in the range from 65/35 to 35/65).

Depending on the compounds of formula (I) and (II) used and their molar ratio, the corresponding amino esters can be uniform compounds or mixtures of amino esters; they correspond to the following general formula

R-CO-O-alkylem-NHRi0 (III),

where R10 is hydrogen, -alkylene2-OH, -alkylene2-0-C0-R or - (CH2MR20R30 »

R20 is hydrogen, Ci_4-alkyl, -CO-R, -alkylene2-OH or -alkylene2-0-C0-R and R30 is hydrogen, Ci-4-alkyl, -alkylene2-OH or -alkylene2-0-C0-R. The sulfomethylation products of the amino esters correspond to the formula

R-C0-0-alkyleni-N (Rn) -CH2-S03M (I '),

wherein R11 is hydrogen, Ci-4-alkyl, -alkylene2-OH, -alkylene2-CO-R,

-CH2-SO3M, NHRgl, - (CH2) 7f-N (R22) "CH2-S03M or

"^ CH2 ^ Ti — Nr22r23>

R21 is hydrogen, -alkylene2-OH, Ci_4-alkyl, -CO-R, -CH2-SO3M or alkylene2-0-C0-R,

R22 Ci-4-alkyl, -alkylene2-OH, -alkylene2-0-CO-R or -CH2-SO3M,

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CH 676 183G A3

R23 Ci-4-AlkyI, -Alkyleri2-OH or -Alkyleri2-0-C0-R and

M is hydrogen or a cation.

The particularly preferred derivatives of monoethanolamine and diethanolamine correspond to the formula

R'_C0_0-CH2-CH2-N (Ri2) -CH2-S03M (I ")

wherein R12 is hydrogen, —CH2 — CH2 — OH, —CH2 — CH? .— O — CO — R 'or —CH2 — SO3M and

R 'each mean linear or branched, primary C 1-7 alkyl and can be uniform compounds or, preferably, mixtures.

The process for the preparation of the sulfomethylation products defined above is characterized in that an alkanolamine of the formula (I) is acylated with an acid of the formula (II) or a functional derivative thereof to give the ester of the formula (III) and non-acylated primary and / or secondary amino groups sulfomethylated with formaldehyde and a sulfite.

As functional acid derivatives, e.g. the corresponding halides (chlorides and bromides), the anhydrides and the Ci-2-alkyl esters are mentioned. Free acids of the formula (II) are preferably reacted with the compounds of the formula (I).

The esterification takes place under conditions which are usual per se, e.g. in the presence of an inert solvent or, preferably, in the absence of any solvent, and using reaction temperatures such that the condensation by-product resulting from the condensation, in particular water, can be evaporated or distilled off, advantageously in the temperature range between 100 and 250 ° C., preferably under reduced pressure .

The reaction conditions are primarily chosen so that the degree of esterification is as high as possible with the lowest possible degree of amidation. This is conveniently e.g. achieved in that the free acid of formula (II) is used for the reaction with compounds of formula (I) or / and in that the molar ratio (II) / (I) is chosen as low as possible. Preferably at least 0.5 mol of acid of the formula (II) are used per mole of compound of the formula (I). If the compound of formula (I) contains a primary amino group as radical -NR2R3, then this can be regarded as being equivalent to the hydroxyl group in terms of reactivity with the acid. 0.5-2 mol, preferably 1-2 mol, of acid of the formula (II) are advantageously used per mol of primary N- (aminoalkyl) alkanolamine; 0.5-2, preferably 0.6-2, mol of acid of the formula (II) are advantageously used per mol of dialkanolamine, and 0.5-1 mol of acid of the formula (II) are preferably used per mol of monoalkanolamine.

The progress of the esterification can be followed by determining the distillate or the acid number of the reaction mixture; the implementation can be considered practically complete if e.g. starting from the free acid of formula (II), the acid number has fallen below 10.

The reaction mixture now contains the corresponding esters of the formula (III) as the main product, optionally in addition to unreacted alkanolamines of the formula (I) and / or corresponding alkanolamides as by-products.

If desired, the reaction product can be separated into the individual components. However, the reaction product is preferably used as it is; for the further reaction with the formaldehyde and the sulfite, it is expedient to titrate the reactive nitrogen-bound hydrogen atoms, which e.g. can easily be done with perchloric acid in glacial acetic acid (in a manner known per se); the corresponding titration can then be given in grams of product, which correspond to a Val convertible (= sulfomethylatable) amine.

For the reaction with formaldehyde and sulfite, the formaldehyde can be added in any conventional form, e.g. as formaldehyde (in particular as an aqueous formaldehyde solution) or in the form of a formaldehyde-donating compound, such as e.g. Metaformaldehyde or paraformaldehyde; for the introduction of the sulfo group, e.g. an alkali metal sulfite, bisulfite or pyrosulfite can be added or SO2, preferably in the presence of alkali metal bases, can be introduced into the reaction mixture. The cations M occurring in the molecule generally suitably correspond to those which occur in the sulfonation with the sulfite (or with SO2 and base), and are preferably alkali metal cations, in particular lithium, sodium or potassium, of which sodium is preferred as the most economical. The reaction with the formaldehyde is advantageously carried out in an aqueous medium at temperatures between 50 ° C. and reflux temperature, preferably between 80 and 100 ° C. The sulfonation is most easily carried out at the same temperature at which the formaldehyde is reacted and in the same reaction medium But it can also formaldehyde, for example with a corresponding bisulfite or pyrosulfite to the compound of the formula

HO-CH2SO3M (IV)

are first reacted (e.g. by stirring the reaction components in an aqueous medium under heat, e.g. at 30-70 ° C, preferably at 50 ° C) and these for sulfomethylation of the amino esters,

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CH 676 183G A3

ter the sulfomethylation conditions described above, are further implemented. Depending on the desired degree of sulfomethylation, formaldehyde and sulfite or compound (IV) can be used in the corresponding molar ratio per val sulfomethylatable amine; the molar ratio of formaldehyde / val amine is advantageously at least 0.2; the upper limit of the molar ratio of formaldehyde / val amine can be as large as is sufficient to achieve an exhaustive sulfomethylation; 0.2-2.0 mol of formaldehyde [or the corresponding amount of a formaldehyde-donating compound or the compound of the formula (IV)] is used, preferably 0.8-1.6 mol. The molar ratio of sulfite (SO2 or preferably pyrosulfite or bisulfite) is expediently equivalent to that of formaldehyde, in particular not lower than that of formaldehyde; the molar ratio of sulfite to val amine is advantageously 0.2-2.0 and preferably 0.8-1.6, the molar ratio of sulfite / formaldehyde advantageously being at least 1: 1 and preferably not exceeding a 10% excess.

If desired, the sulfomethylation products can be isolated from the reaction mixture or worked up. However, the products are preferably neither isolated nor worked up.

The sulfomethylation products according to the invention are used for finishing fiber material, whereupon they have softening properties, and a further aspect of the invention is the use of the sulfomethylated amino esters according to the invention for finishing fiber material, in particular for softening textile or non-textile fiber material.

The sulfomethylated compounds according to the invention have an excellent softening effect, with the deterioration of the optical brightening (a reduction in the degree of whiteness) being avoided as far as possible when softening optically brightened material and the hydrophilicity of the substrate being retained as far as possible.

The softening active substance essential to the invention are the sulfomethylated amino esters, and the reaction by-products (essentially unreacted starting products, sulfomethylated amino alcohols, non-sulfomethylated esters, non-sulfomethylated amides and / or sulfomethylated hydroxyalkylaminoalkylamides) have no particularly disadvantageous effect according to the invention on the sulfomethylated aminoamides exercise (some of them are also plasticizers), but the sulfomethylated esters essential to the invention have an improving effect on the by-products mentioned; i.e. the higher and more selective the degree of esterification of the amino alcohols and the higher the degree of sulfomethylation of the sulfomethylatable amino groups, the gentler the effect on the optical brightening and the higher the hydrophilicity with an optimal softening effect.

In principle, the substrate can be any hydrophilic substrate and is preferably cellulose-containing; cellulose fibers (cotton, linen, jute, hemp, paper) and cellulosic fiber mixtures (polyester / cotton, polyamide / cotton) are particularly suitable, of which cotton is particularly preferred. The substrate can generally be used in any form of processing commonly used for the appropriate equipment, e.g. as loose fibers, threads, fabrics, knitted fabrics, nonwovens, paper, felts, velvet, tufted goods and carpets, in particular cellulose ware that is optically brightened with conventional optical brighteners for cellulose. Such optical brighteners are well known and described in the literature and in the art, e.g. in DE-OSes 1 811 715, 1 963 065, 2 056 195, 2 145 384, 2 233 429, 2 403 455.2 406 883.2 430 624.2 601 749 and 2 715 864, in DE-PSs 731 558.1 106 334.1 170 765, 1 793 982.1 795 047 and 1 939 521, in CH-PS 318190 and 321 109, in BE-PS 754 466 and in GB-PS 967 110; among these, the compounds of the bis- (triazinylamino) -stilbene disulfonic acid series are particularly noteworthy. The softening finish according to the invention, which is a non-permanent finish and, in the case of textile material, is used in particular for improving the grip of the goods before assembly, can take place simultaneously with the optical brightening or after the optical brightening; if desired, after the optical brightening and before the finishing according to the invention, the optically brightened substrate can be printed in color or after the optical brightening and before the finishing according to the invention or at the same time also colored with it.

The equipment is carried out under conditions which are conventional per se and are generally suitable for the corresponding substrate, essentially from an aqueous medium, e.g. by impregnation processes (padding, spraying or foam processes) or pull-out processes from long or short liquors (e.g. also in jet dyeing equipment) e.g. at 15 to 40 ° C, whereby the pH of the liquor can vary within a very wide range from clearly basic to clearly acidic, e.g. between pH 3.5 and pH 9, the neutral to weakly acidic conditions being preferred, in particular pH 7 to 4.5. The treated substrate can then be dried under conventional conditions, e.g. at room temperature or higher temperature, mainly at 80-140 ° C.

The sulfomethylation products according to the invention are advantageously used in the presence of non-ionic surfactants, preferably O / W emulsifiers. Particular preference is given to adding the nonionic surfactants and, if appropriate, water to the resulting reaction mixture immediately after the production of the products, so that a highly concentrated liquid preparation can be produced, and a special subject of the invention are the finishing preparations for fiber material which are produced by a Content of the sulfomethylation products defined above and preferably also non-ionic surfactants. Concentrated, aqueous preparations of the sulfomethylation products according to the invention advantageously contain 3-50, preferably 8-30,% by weight.

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Sulfomethylation product, optionally in addition to non-ionic surfactant. The relative amount of non-ionic surfactant to the sulfomethylation product is expediently kept as low as possible, specifically as it is sufficient so that a sufficiently stable preparation (dispersion or solution) can result; the amount of nonionic surfactant is advantageously 3-50% by weight, preferably 10-25% by weight, of the sulfomethylation product. Before application, the preparations (which may also contain other usual additives such as a fungicide) can, if desired, be diluted to stock solutions and added to the treatment liquor in the usual way.

The concentration of the sulfomethylation products according to the invention, based on the substrate, can vary within wide limits, depending on the desired effect and application method, and is advantageously 0.3-10%, preferably 0.5-5%, based on the substrate.

The non-ionic surfactant can generally be a conventional surfactant, as is generally known in the literature and technology as a non-ionic oil-in-water emulsifier, in particular those with HLB values of 6-19, preferably 8-19, in particular water-soluble surfactants come into consideration.

Suitable, non-ionic surfactants are generally customary compounds, essentially those which contain at least one lipophilic hydrocarbon radical, advantageously having at least 9, preferably 9-24, carbon atoms and at least one non-ionogenic hydrophilic radical, which advantageously contains an optionally propylene glycol unit containing polyethylene glycol residue and / or the residue of a higher polyol (eg glycerin, mannitol, pentaerithritol or sorbitol); Among the hydrophilic surfactants, the hydrophilic Pluronic types and Tetronics can also be mentioned. The following categories of non-ionic surfactants can be mentioned:

Polyoxyethylation and optionally oxypropylation products of saturated and / or unsaturated, linear and / or branched aliphatic alcohols, of alkylphenols, of fatty acids, of fatty acid alkanolamides, of fatty acid polyol partial esters and of vegetable or animal fats or oils;

Fatty acid polyol partial esters;

Non-ionic ethylene oxide / propylene oxide copolymers with a high proportion of ethyleneoxy units (Pluronic types) and ethylene oxide / propylene oxide addition products of ethylene diamine, with a high proportion of ethyleneoxy units (Tetronic types), which are considered non-ionogenic surfactants due to the high degree of oxyalkylation.

The polyol partial esters mentioned are primarily tri- to mono-, advantageously di- or preferably monoesters of aliphatic polyols with 3 or more hydroxyl groups, preferably of glycerol, mannitol, pentaerythritol or sorbitol.

Preferred nonionic surfactants are generally polyoxyethylation products of aliphatic alcohols, of alkylphenols, of aliphatic fatty acids and of polyol partial esters of aliphatic fatty acids.

The fatty acid residues occurring in the non-ionic surfactant can generally be acyl residues of conventional alkyl carboxylic acids or alkenyl carboxylic acids, mono-ethylenically unsaturated acids being advantageous as alkenyl carboxylic acids. The alkyl radicals as the only iipophilic radicals [(as for example in the formula (V) below] advantageously contain at least 9 carbon atoms, preferably 9-24 carbon atoms, in particular 9-18 carbon atoms and can be linear or branched. In the aikylaryl radicals, for example in the rest of the formula (a) below, the alkyl radicals advantageously contain 4-12 carbon atoms and can also be linear or branched .. If the ipophile radical is the acyl radical of a carboxylic acid, then it is advantageously the radical of a fatty acid, essentially an alkyl or alkenyl carboxylic acid which advantageously contains 9-24, preferably 12-20, carbon atoms, with lauric acid, myristic acid, stearic acid and oleic acid being particularly preferred The polyethylene glycol derivatives, in particular also the formulas below, are generally average formulas, ie those in which the specified number of ethyleneoxy units an average number i st. In the lipophilic remainder of the surfactants, the number of carbon atoms can also be an average number.

Among the nonionic surfactants mentioned, those of the following formulas are particularly preferred:

R6- {0-CH2-CH2} pOH

(V)

and

(RyCO ^ qX

(VI),

wherein R6 is C9-24 alkyl or alkenyl or a radical of the formula

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CH 676 183G A3

(R,

(a),

R7-CO-each the acyl radical of an alkyl or alkenyl carboxylic acid with 12-20 carbon atoms, R8 C4-12 alkyl,

X is the q-valent radical of glycerol, pentaerithritol or sorbitol or a polyethylene glycol of the formula p 5 to 100,

q 1 or 2,

r 1 or 2 and s 3 to 60

mean and polyoxyethylation products of compounds of the formula (VI), the number and length of the lipophilic radicals and number of -CH2-CH2-0 groups being appropriately selected so that the HLB value of the nonionic emulsifier or emulsifier mixture is between 6 and 19 , preferably between 8 and 19.

The HLB value of the non-ionic surfactants can be calculated using a simple known formula, knowing the lipophilic radical and the number of ethyleneoxy or propyleneoxy units.

In the following examples, the percentages are by weight and the temperatures are given in degrees Celsius; Products that are used in the form of preparations are, unless otherwise stated, aqueous preparations.

285 g of stearic acid (= 1 mol) and 105 g of diethanolamine (= 1 mol) are condensed at 160-170 ° under vacuum until no more water is distilled off; the acid number measured subsequently is 2.5. The condensate is titrated in glacial acetic acid with perchloric acid and gives a value of 762 g for the sulfomethylatable amino groups (762 g condensation product = 1 val amine).

125 g of 36% formaldehyde (= 1.5 mol) are added to a val amine (= 762 g of product) and the mixture is heated to 85-100 °. At this temperature, 390 g of 40% sodium bisulfite (= 1.5 mol) are added dropwise over the course of 30 minutes. Allow to react for 6 hours at this temperature.

The sulfomethylation product obtained is mixed with 20% (based on the dry weight of the reaction mixture) of the adduct of 25 moles of ethylene oxide and 1 mole of oleyl alcohol and emulsified with 80-90 ° C. hot water to a 13% dry weight content.

92.70 g of an isostearic acid with an equivalent weight of 309, 81.00 g of stearic acid and 63.00 g of diethanolamine are condensed under vacuum at 150-160 ° until no more water is distilled off; the titrated acid number is 4.50. The Val value for the sulfomethylatable amino group gives 1236.6 g of condensate per Val amine.

An adduct formaldehyde / bisulfite is prepared by stirring 22.84 g 36% formaldehyde, 50 g water and 28.03 g sodium pyrosulfite (NazSaOs) at 50 ° for 30 minutes.

The adduct is added to the condensate and stirred for 51/2 hours at 85-95 ° to complete the sulfomethylation.

The product obtained is mixed with 14.1% (based on anhydrous sulfomethylation product) of the adduct of 50 mol of ethylene oxide and 1 mol of nonylphenol and emulsified to 80% dry weight with 80-90 ° C. hot water.

The following table lists further products (Examples 3 to 12) which can be prepared analogously to that described in Examples 1 or 2.

H0-4CH2-CH2-0fr-H

(VII),

example 1

Example 2

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CH 676 183G A3

At

Alkanol

Acidity of

Mol of suction / val

Mol form non-ionic

% Surfactant,

Dry play aimin the

Formula (II)

re pro

Amine aldehyde

Surfactant related

No.

Formula (!)

MolAI-

kanol

amine

and moles of bisulfite per val amine

stop on sulfomethylated product

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Diethanolamine

Coconut fatty acid

2nd

3720

1.5 / 1.5

as in example 2

25%

25%

4th

Diethanolamine

Stearic acid

0.6

439

1.5 / 1.5

Oleyl poly {25) -

ethylene glycol

ether

20%

18%

5

'Diethanolamine

Stearic acid

0.6

443

1.75 / 1.75

Oleyl-poly (25) -

ethylene glycol

ether

20%

18%

6

Diethanolamine

Stearic acid

0.6

445

0.85 / 0.85

Oleyl poly (25) -

ethylene glycol

ether

20%

18%

7

Diethanolamine

Stearic acid

0.6

435

0.21 / 0.21

OIeyl-poly (25) -

ethylene glycol

ether

20%

18%

8th

Diethanolamine

Oleic acid

2nd

5058

1.5 / 1.5

Oleyl poly (25) -

ethylene glycol

ether

22%

15%

9

Diethanolamine

12-hy

droxystea

rinic acid

1.5

1503

1.5 / 1.5

as in example 2

22%

20%

10th

Diisopro

Behen

1

1077

1.5 / 1.5

like in the example

17%

18%

panolamine acid

4th

11

Monoethanolamine

Lauric acid

1

4807

1.5 / 1.5

Oleic acid monoester of poly ethylene glycol 300

16%

13%

12

N- (2Hy-

Coconut fat

2nd

1703

1.5 / 1.5

Oleic acid mono-

16%

13%

droxyethyl) acid

ester des poly-

ethylene

ethylene glycol

diamine

300

Application example A

Jersey made of leached cotton is made under neutral pH conditions with a liquor containing 0.69 / 1 of the optical brightener of the formula

S03 Well

SO yeah

^ C-CHOH-CHg-N-CHgCHgCN

J2

and 30g / l of the emulsified product according to Example 1, padded to a dry weight gain of 85% and then dried at 140 ° for 90 seconds. A sample of the cotton finished in this way is heated to 150 ° for a further 10 minutes after drying. The softness, the degree of whiteness and the hydrophobic effect are measured from both cotton samples.

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Application example B

The procedure is analogous to that described in Example A, but in two stages, i.e. in a first process, the cotton is padded to a 85% dry weight gain with a padding liquor containing 0.6 g / l of the optical brightener mentioned, after which the cotton jersey is dried at 140 ° for 90 seconds; This jersey material is then padded with a liquor containing up to 85% dry weight, which contains 30 g / l of the product according to Example 1, after which the cotton jersey is dried again at 140 ° for 90 seconds.

Application example C

A cotton yarn brightened with the optical brightener specified in Example A is added in a liquor ratio of 1:10 to a liquor which, in addition to 1 g / l sodium acetate and 0.75 ml / l acetic acid, 0.5% (based on the substrate) of the product according to Example 1 (calculated as the dry content of the emulsion). The liquor is warmed to 30 ° in the course of 30 minutes with constant movement of the substrate and held at this temperature for 1/2 hour, after which the yarn is removed from the liquor and dried.

Analogously to that described in Examples A, B and C, the products of Examples 2-12 (same concentration of product as for the product of Example 1) are also used.

The fabric finished according to the above examples has a very pleasant soft feel, the degree of whiteness of the fabric being retained to a high degree and the hydrophobization being minimal.

Claims (1)

Claims 1. sulfomethylation products of amino esters from alkanolamines of the formula HO-alkylem-NHRi (I), where Ri is hydrogen, C 1-4 alkyl, alkylene2-OH or - (CH2} ypNR2R3, R2 is hydrogen, alkylene2-OH or Ci ^ alkyl, R3 is hydrogen, -alkylene2-OH or C-i - ^ - alkyl, Alkyleni and Alkylen2 each have 1,2-ethylene or 1,2-propylene and n 2 or 3 mean, and fatty acids of the formula R-COOH (II), where R is optionally Cn-21 alkyl or alkenyl containing hydroxyl groups, or functional derivatives thereof. 2. Sulfomethylation products according to claim 1 of the formula R_C0-0-alkyleni-N (Rn) -CH2-S03M (I ') wherein R11 is hydrogen, -Ci-4-alkyl, -alkylene2-OH, alkylene2-0-C0-R, -CH2-SO3M, -fCH2) 7rNHR21, —CCH2- ^ TrN (R22} -CH2-S03M or ~ {cH2) frNR22R23 ' R21 is hydrogen, -alkylene2-OH, Ci_4-alkyl, -CO-R, -CH2-SO3M or -alkylene2-0-C0-R, R22 Ci-4-alkyl, -alkylene2-OH, -alkylene2-0-C0-R or -CH2-S03M, R23 Ci-4-alkyl, alkylene2-OH or alkylene2-0-CO-R and M is hydrogen or a cation. 3. A process for the preparation of the products according to claim 1, characterized in that an alkanolamine of the formula (I) with an acid of the formula (II) or a functional derivative thereof, acylated and non-acylated primary and / or secondary present in the product Amino groups with formaldehyde and a sulfite suifomethyliert. 4. Aqueous preparations, characterized by a content of sulfomethylated amino esters according to claim 1 or 2. 5. Aqueous preparations according to claim 4, characterized by a content of sulfomethylated amino esters according to claim 1 or 2 in addition to non-ionic surfactants. 9 5 10th 15 20th 25th 30th 35 40 45 50 55 60 65 CH 676183G A3 6. Finishing agent for fiber material, characterized in that it contains at least one sulfomethylated amino ester as claimed in claim 1 or 2 as the softening active substance. 7. finishing agent according to claim 6, characterized in that it additionally contains a non-ionic gene surfactant. 8. Use of the sulfomethylated amino esters according to claim 1 or the preparations according to one of claims 4-7 for finishing fiber material. 9. Use according to claim 8 for the non-permanent, softening finish of cellulose fiber material. 10. Use according to claim 9 for the non-permanent, softening finish of textile material made of cellulose brightened with anionic brighteners. 10th