JPS6112654A - Sulfomethylated amino ester - Google Patents

Abstract

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

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to sulfomethylated amino-esters and their preparation useful as finishing agents for fiber supports, in particular as softeners. R4-NHR11 where R1 is hydrogen, cl-4furkyl, -R5-OH or +
CH2 story NR2R3, I (2 and R3 are independently hydrogen, -R, s -oH
i is C4-, alkyl, R4 and R5 are independently ■, 2-ethylene or (r
J-t 12-llopyrene, where n is 2 or 3, or an alkanolamine of the formula or a mixture thereof; IJ'r'i 1ujG, f: fc is the reaction product of the amino ester with its functional sieve 4y form. Alkyl as R1, R2 or R3 is preferably methyl or ethyl, especially methyl. Preferred meanings for R4 or R5 are independently 1.2-
Ethylene, -R4-OH di, or -R4-OH
is preferably β-hydroxyethyl.

R7 is preferably hydrogen or -R5-OH,
Preferred is hydrogen or β-hydroxyethyl.

Preferred alkanolamines of formula I are monoethanolamines and jetanolamines, especially jetanolamines.

The alkyl or alkenyl moiety of R can be branched or straight. Preferably, R is unsubstituted alkyl, alkenyl or a mixture of alkyl and alkenyl, more preferably "15-21alk2.013-217'" or a mixture thereof, and <KCl5-21 Alkyl, C15-21 alkenyl or mixtures thereof, especially those derived from technical mixtures of fatty acids.

Suitable fatty acids R-COOH include lauric acid, myristic acid, palmitic acid, impalmitic acid, stearic acid,
those derived from technical mixtures of instearic acid, hydroxystearic acid, oleic acid, arachidic acid, behenic acid or mixtures thereof, special fatty acids such as tallow fatty acids, coconutae'id , isopalmitic acid, isostearic acid and mixtures of stearic acid and isostearic acid.

Iso-7, lumitic acid or isostearic acid are described, for example, in U.S. Pat. No. 2,812,342 or Kirk-Othmer's Encyclopedia of Chemical Technology.
@m1cal Teehnology month.

It means a technical mixture of isomers as disclosed in 3rd Edition, Vol. 4 + No. 862.

More preferably R-COOH is a saturated aliphatic fatty acid or a mixture of saturated aliphatic fatty acids, especially stearic acid or stearic acid/isostearic acid. Preferred amino-esters are the above acids and monoethano-esters.
Preferably, esterification products with jetanolamine, especially jetanolamine and stearic acid or mixtures of stearic acid/isostearic acid, the latter being preferred.

is a stearic acid/isostearic acid weight ratio ranging from 65/35 to 35/65).

Suitable functional derivatives of fatty acids of the formula (1) are, for example, acid halides such as acid chlorides or bromides, anhydrides and methyl or ethyl esters.

In general, the amino-ester a formed from the reaction of an alkanolamine of formula (1) with a fatty acid of formula (2) or a functional derivative thereof is 2) R-CO-0-R-NHR,ol, where Rlo is hydrogen, - R5-OH1-R5-0-CO-R or ÷CH2 story NR2oR3o, where R2o is hydrogen, C1-4 alkyl, -CO-R1-R5
-OH or -R5-0-CO-R, or R
is hydrogen, C alkyl, -R5-OH or 50
l-4-R5-0-CO-R, and R*%*Rs and n have the meanings given above.

Depending on the compounds of formulas I and H and their molar ratios, the resulting amino-esters can be obtained as single compounds or as mixtures.

The corresponding sulfomethylated compound has the formula ■R-CO-0-
R4-N(R41)-CH2-so3My In the formula, R11 is C1-4 furkyl, -R5-OH, -R5-0
-CO-R.

-CH2-SO3M, 10cH2-NHR21, +CJ(
2qN(R22)-CH2-8o3Mt *U+0H2
YaNR22R23-c available・R21 is hydrogen, -R5-OH1c1-4 alkyl, -C
OR, --CH2-8o3 or -R5-0-CO-
RT 6 p, R22 is C1,7A'ki Jv, -R5
-OH, -R520-CO-R or -CCH2-8o
3 rashi, R23-C1-4 alkyl, -R5-OHt taha-R
5-0-CO-R, M is hydrogen or a cation equivalent, and R, R4
, R5 and n have the meanings given above.

When M is an equivalent of a cation, it is preferably an alkali metal cation, such as sodium, potassium or lithium, with sodium being preferred.

Preferred sulfomethylated products of the invention are a combination of a fatty acid of formula (1) or a functional derivative thereof, preferably stearic acid or a mixture of stearic acid and instearic acid, with monoethanolamine or jetanolamine, especially jetanolamine. It is obtained by sulfomethylation of amino-esters, which are reaction products.

Particularly preferred sulfomethylated compounds of the invention are of formula I
Va R'-CO-0-CH2-CH2-N(R,2)-CH
2-8o3M Iva where M is as defined above, ml is a linear or branched -c17-19 alkyl or a mixture of such alkyls, and R42 is hydrogen, -CH2CH2-OH, -CH2-CH
2-0-CO-R' or -CH2-8o, M, or a mixture thereof.

The most preferred sulfomethylated compounds of the present invention are those obtained by sulfomethylation of the esterification product of jetanolamine and a mixture of stearic acid/instearic acid, in which stearic acid/instearic acid is present. The weight ratio of is 65/35 to 35/65.

The ulfomethylated amino-esters of the present invention are prepared by reacting an alkanolamine of formula I with a fatty acid of formula II or a functional derivative thereof, preferably in the free acid form, and then reacting with the acyl present in the resulting amino-ester. 1. It is produced by sulfomethylation of the primary amino group of carbon dioxide with formaldehyde or a formaldehyde-generating compound and nitrite or s02.

The reaction between an alkanolamine of formula I and a compound of formula] is an esterification, and the conditions of the reaction are therefore chosen such that the compound of formula I occupies the predominant proportion. This reaction can be carried out in the presence of an inert solvent; preferably it is carried out in the absence of a solvent and at a temperature such that the secondary condensation products, especially the esterification products, can be evaporated or distilled off. do. This reaction is conveniently 100 to 250
It is carried out at a temperature of 0.degree. C., preferably under reduced pressure.

In order to obtain as high a degree of esterification as possible and to reduce amidation to a minimum, it is preferable to use the compound of formula (1) in the form of the free acid and to reduce the molar dead amount of the compound of formula (1) to as low as possible. It is recommended that you select Preferably 1 of the alkanolamines of formula 1
It is used in an amount of at least 0.5 mole per mole. In the compounds of formula I, when R1 is a primary amino group,
This amino group can react with an acid of the formula...+g: comparable to that of a hydroxy group. -N-( of formula I
aminoalkyl)-alkanolamine from 1:05 to 2
, preferably a molar ratio of '1:0.2-2.

It is preferable to use 1/It. When the alkanolamine of formula ■ is jetanolamine, it is used in the molar ratio 1/II of 1:0.5-2, preferably 1:0.6-2; When the alkanolamine is monoethanolamine, the molar ratio is 1/I
I is preferably 1:0.5-1.

The progress of the esterification can be followed by known methods, for example by periodically measuring the volume of distillate or the acid number of the reaction mixture. Esterification is generally sufficient if the compound of formula (1) used as starting material is an acid in free form, for example when the acid number of the reaction mixture is less than 10.

As will be appreciated, the resulting reaction mixture consists primarily of an amino-ester or a mixture of amino-esters, in particular an amino-ester of formula m, optionally with an insignificant amount of secondary products, such as unreacted Alkanolamines can be used/or mixed with the corresponding alkanolamides.
contains. If desired, the amino-ester or mixture of amino-esters can be separated from the resulting reaction mixture according to known methods. Preferably, the reaction mixture is used directly for subsequent sulfomethyl without any purification steps.

The sulfomethylation of the resulting amino-esters is carried out using formaldehyde p, e.g. formaldehyde in the form of an aqueous solution, or formaldehyde-generating compounds, e.g. metaformaldehyde or U/e formaldehyde, and sulfites, e.g. alkali metal sulfites or S
It is carried out by reacting with O2 in the presence of an alkali metal base. Preferably, the sulfite is an alkali metal pyrosulfite or bisulfite. Generally, in the process of sulfonation, cations of alkaline, potassium, and all-polarity bases are introduced into the resulting molecule along with the sulfite or SO2 used. The alkali metal is preferably lithium, sodium or potassium. A preferred cation is sodium.

The reaction with formaldehyde is conveniently carried out in an aqueous medium at 50%
It is carried out at a temperature of 0.degree. C. to reflux, preferably 80.degree. C. to 100.degree. The subsequent sulfonation is preferably carried out in the same medium and at the same temperature as the reaction with formaldehyde.

Alternatively, formaldehyde can be first reacted with bisulfite or pyrosulfite to obtain the formula VHO-CH2-803.
A compound of M y can be produced. The reaction is suitably carried out simply by mixing the starting materials according to known methods, for example by stirring in an aqueous medium and
For example, it is carried out by heating to a temperature of 30 to 70°C, preferably 50°C. The compound of formula (1) is then reacted with the amino-ester under the same conditions as described above for the sulfomethylation.

The amount of formaldehyde, sulfite SO2 or compound of formula (1) required for sulfomethylation depends primarily on the desired degree of sulfomethylation. Before carrying out the sulfomethylation, it is recommended to titrate the reactive hydrogen atoms bound to the nitrogen atoms present in the reaction mixture resulting from the esterification. This titration can be carried out according to known methods, for example using perchloric acid in glacial acetic acid; it gives equivalents of amino-ester per gram equivalent of amino group which can be sulfomethylated, and in this specification Advantageously, it is called amine val J.
Formaldehyde, a formaldehyde-generating compound or a compound of formula ■ is used in an amount of at least 0.2 mol/amine value, with an upper limit as high as required to sulfomethylate all of the reactive amine groups present in the molecule. It's the amount.

Preferably, the formaldehyde, formaldehyde-generating compound or compound of formula (1) has a concentration of 0.2 to 2.0. More preferably, it is used in an amount of 0.8 to 1.6 mol/amine value.

The sulfite or SO2 used in the sulfonation is advantageously used in a molar ratio equal to or preferably lower than that of formaldehyde or formaldehyde-generating compounds. The molar ratio of sulfite or SO□ to amine number is within the same range as above for formaldehyde, and the molar ratio of sulfite or SO2 to formaldehyde (or formaldehyde-generating compound) is conveniently between 1 and 1.
．． The ratio is 1:1.

The resulting sulfomethylated compounds can be isolated and purified using conventional methods. Preferably, the reaction mixture is used without being subjected to any purification steps. It may contain secondary products, such as unreacted starting materials, sulfomethylated amino-alcohols, non-sulfomethylated esters, non-sulfomethylated amides and/or sulfomethylated hydroxyalkylaminoalkylamides.

The sulfomethylated amino-esters of the present invention can be used as finishing agents for textile and non-fibrous Hamura supports.
It is particularly useful as a flexible material. They impart flexible properties to the support and are particularly suitable for finishing optically brightened supports, the optical brightness and hydrophilicity of the optically brightened support being not significantly impaired. Depending on the conditions and materials used1, the degree of fluorescence brightening can be maintained or even improved. The compounds of the invention can be used in the a↓ form or in the form of the final reaction mixture; one should be aware that any secondary products that may be present do not adversely affect the properties of the sulfomethylated amino-esters. , is preferable from an economic point of view. Compounds which are obtained with a highly selective ester ratio of the starting alkylamine and in which the highest proportion of the amino groups that can be sulfomethylated are sulfomethylated are preferred; and does not adversely affect the optical brightening properties when applied to optically brightened supports.

Suitable supports include hydrophilic fibrous materials consisting of natural, synthetic or semi-synthetic fibers, and paper; preferred supports include paper and fibrous materials containing natural or regenerated cellulose, such as cotton, cotton, jute or hemp, said fibrous material may be blended with composite fibers such as polyester or polyamide. It can be in the form of non-rubbed fabric, paper, felt, velpet, carpet or tufted products.

Finishing of the support using the softener of the invention can be carried out according to known methods. The sulfomethylated amino-esters can be depleted from aqueous solutions by conventional finishing techniques, for example by inclusions such as padding, spraying or foam methods, or by the ratio of long or short numbers to fiber material. By exhaustion (eg, also by dye-jet machine), it can be conveniently applied at a temperature of 15 to 40°C. They range from alkaline to hostile, for example about 3.5 to 9
It is possible to apply a wide range of P in the range of P1, and neutral to slightly acidic conditions, particularly P1 of 17 to 4.5, are preferred.

The softeners of the present invention are preferably applied to cellulose supports that have been optically brightened with optical brighteners such as those commonly used for cellulosic materials. Such optical brighteners are known and disclosed, for example, in the following patents: U.S. Pat.
, No. 018,287, British Patent No. 1. ．． 313,469
No. 896,533, No. 1,243,276 and No. 967.110, Canadian Patent No. 921,
658, German Patent No. 731,558, German Patent No. 1,
No. 793,982 and No. 1,795,047, German Published Patent Application No. 1,811,715, Rule 5, No. 1,
No. 963,065, No. 2,056,195, No. 2
, 233,429, 2,601,749 and 2,715,864 and Swiss Patent No. 318
, No. 190 and No. 321.109. Optical brighteners of the bis-(trianonylamino)-stilpenedisulfonic acid series are particularly preferred.

Alternatively, the finishing treatment with the sulfomethylated compounds according to the invention can be carried out simultaneously with the fluorescent whitening of the support.
The softener can also be applied to the support which has been optically whitened sequentially and then dyed or printed according to known methods, in which case the softening is preferably carried out simultaneously with the final rinsing step.

When the softening treatment is completed, the support may be dried, e.g. at room temperature or preferably at 80-140°C.
Can be dried at a temperature of

The concentration of sulfomethylated amino-esters on the support can be varied within wide limits depending on the desired effect and application technique. Preferably, the temperature is from 0.3 to 10 inches, more preferably from 0.3 to 10 degrees, based on the dry temperature of the support.
．． It is 5-5%.

The sulfomethylated amino-esters of the invention are obtained in the final reaction mixture as an aqueous composition, which mixture can be further diluted with water before use. Preferred concentrated aqueous compositions contain from 3 to 50%, particularly from 8 to 30%, of the sulfomethylated compound.

Conveniently, the sulfomethylated amino-esters of the invention are used in admixture with a nonionic surfactant, preferably a nonionic oil-in-water emulsifier. Finishing compositions containing a sulfomethylation product according to the invention together with a nonionic surfactant or a mixture of nonionic surfactants are also suitable.

Forms part of the present invention. Nonionic surfactants are
It is conveniently added directly to the final reaction mixture, preferably in an amount kept as low as possible in order to obtain a stable preparation. Advantageously, the amount of nonionic surfactant is between 3 and 50% by weight of the sulfomethylated product, preferably between 10 and 2%.
It is 5% by weight.

Furthermore, auxiliary substances, such as fungicides, can be added to the finishing preparations according to the invention.

Preferred nonionic surfactants are those having an HLB value of 6 to 19, more preferably 8 to 19, especially those that are water-soluble.

Nonionic surfactants generally have at least one lipophilic hydrocarbon residue of at least 9, preferably 9 to 24 carbon atoms and at least one nonionic hydrophilic residue. species or two or more compounds;
Said hydrophilic residues are preferably mono- or polyethylene glycol groups, which may contain polypropylene glycol units, or are residues of polyols such as glycerol, mannitol, pentaerythritol and sorbitol. Other suitable types include hydrophobic Pluronics and Tetronics whose high zolopyrene oxide content can be considered a lipophilic residue.

Particular types of nonionic surfactants include: ethylene oxide (FJo) and/or propylene oxide (PO) (preferably KO alone) in saturated and/or unsaturated linear and/or or branched aliphatic alcohols, alkylphenols, fatty acids, fatty acid alkanolamides, partial fatty acid esters of polyols, and products obtainable by addition to vegetable or animal fats or oils; polyols partial fatty acid Nisdel; EO/P with high EO content
O copolymers (fluronic type); EO/PO addition products to ethylenediamine (tetronic type) with high IO content.

In the addition products of IO to aliphatic alcohols, alkylphenols or fatty acids, the number of EO units is an average value and does not necessarily have to be an integer number.

The fatty acid residues can be saturated or unsaturated (in the case of unsaturation, they are preferably monoethylenically unsaturated) and contain from 9 to 24 carbon atoms, preferably 12
Preference is given to acyl groups having up to 20 carbon atoms, especially the residues of lauric acid, myristic acid, stearic acid and oleic acid. When the alkyl group is the only lipophilic group, it preferably has from 9 to 24 carbon atoms, more preferably from 9 to 18 carbon atoms, and is preferably linear or branched. Something can happen. In alkylaryl groups, the alkyl group preferably has 4 to 12 carbon atoms and can also be straight-chain or branched.

Preferred partial fatty acid esters of polyols are mono-, tri-esters, more preferably mono- or di-esters of aliphatic polyols having three or more hydroxyl groups, preferably glycerol, mannitol, pentaerythritol or sorbitol. - Aesthetics, especially seven-no-ester.

Particularly preferable surfactants have the formula (■) or ■R6→0C
H2CH2soHVl (R, -CO), -X In the formula, R6 is C9-24 alkyl, C9-24 alkenyl or a group of formula (a), and each R7 is independently C11-19 alkyl or C11
-19 alkenyl or a mixture thereof, R8 is C4-1□alkyl, X is a monovalent or divalent residue of sorbitol, glycerol, pentaerythritol or polyethylene glycol of the formula %, and p is 5 to 100, q is 1 or 2, r is 1 or 2, and S is 3 to 60, and a polyethoxylation product of the compound of formula The number and length of the lipophilic residues and the number of ethyleneoxy units are such that the compound or mixture of compounds has an average HLB value of 6 to 19, preferably 8 to 19.

HLB values for nonionic surfactants can be calculated using standard formulas.

The finishing of the sulfomethylated amino-esters of this invention is a non-permanent treatment. It has a softening effect and improves the hand of the textile material. It is intended in particular for the finishing of textile materials used in the manufacture of textiles.

The following examples illustrate the invention. In these examples, all percentages are by weight and temperatures are in degrees Celsius.

Example 1 285 g (1 mol) of stearic acid and 105 g (1 mol) of stearic acid
mol) of jetanolamine are reacted at 160 DEG -170 DEG C. under reduced pressure until no water distills out, at which point the condensation product reaches an acid number of 2.5. Titration of this product with perchloric acid in the presence of glacial acetic acid yields 47132
Give the amine val of the condensation product of g.

Then 125 g (1.5 mol) of aqueous formamide of the 36th grade are added to the amine number 1 (=762 p of condensation product) and the mixture is heated to 85 DEG -100 DEG C. 390 g (1.5 mol) of 40% aqueous sodium bisulfite are then added dropwise at 85.gamma.100.degree. C. and the reaction mixture is subsequently kept at this temperature for 6 hours with stirring.

Based on the dry weight content of the above reaction mixture, add 20φ of the addition product of 1 mole of oleyl alcohol and 25 moles of ethylene oxide to this mixture, and then add to this mixture such that the resulting preparation has a dry weight content of 13. , 80-9
Add water at 0°C.

Example 2 92.70 g equivalent of 309 isostearic acid, 81.
0 (L9) of stearic acid and 63.00 g of jetanolamine are added under reduced pressure at 150-160° C. until no more water distills out, at which point the condensation product reaches an acid number of 4.5. Titration of the oxidizable amine groups gives a condensation product with a amine number of 1236.6 g/a.

36% aqueous formaldehyde of 22.84.9, 50g
of water and 28.0.1' of sodium pyrosulfite (N
IL 2 S 20 s ) is reacted at 50° C. for 30 minutes to obtain the addition product of formula V. This addition product is added to the above mixture and the reaction mixture is subsequently heated to 85-95° C. with stirring. Hold for 5.5 hours.

14.1% based on the dry weight of the sulfomethylated product
The addition product of 1 mole of nonylphenol and 50 moles of ethylene oxide is added to this mixture, and the mixture is then emulsified with water at 80-90°C such that the resulting preparation has a dry weight content of 20%. do.

The procedure of Example 1 or 2 is followed, but as shown in the table below.

Using the starting materials, finished preparations as disclosed can further be obtained.

□ Margin below Application example A Soda-treated cotton tricot with an aqueous liquid containing an optical brightener of the formula O,6 i/l and a finishing formulation of Example 1 of 309/13, based on its dry weight. Pad to an impregnation rate of 85g6. This impregnated support was then heated to 140°C for 9
Dry for 0 seconds.

The resulting cotton sample is further processed at 150° C. for 10 minutes.

Application example B The procedure of application example A is repeated, but in two steps. 1st
In the process, the tricot is heated to 85% of its dry volume with an aqueous liquid containing 0.6 fl/11 of the optical brightener.
% and then dried at 140° C. for 90 seconds. In the second step, the obtained support was
Pad with an aqueous liquid containing the finish formulation of Example 1 of g//j to a pick-up of 85% of its dry weight. The support is then dried at 140° C. for 90 seconds.

Application example C Aqueous containing 1&/l sodium acetate, 0.75 ml acetic acid and 0.5% (based on the weight of the support) of the finishing preparation of example 1 (calculated as dry weight content) A cotton thread which has been optically brightened with the optical brightener of application example A is introduced into the bath. The ratio of liquid to fibrous material is 10:
It is 1. 30. Keep this bath at 30°C with constant stirring.
Hold for 30 minutes and at 30°C for an additional 30 minutes.

The yarn is then taken out and dried.

Repeat the procedure of application example A, B or C, but with Examples 2-
A preparation according to 12 is used.

In the above application example, the finished support is applied in application example A
Even for the further heat-treated cotton tricot, it exhibits a soft and pleasant texture without significantly compromising its optical whiteness and hydrophilicity.

Claims (1)

[Claims] 1. Formula I HO-R_4-NHR_1 I where R_1 is hydrogen, C_1_-_4 alkyl, -R_5-O
H or -(CH_2)-_nNR_2R_3,
R_2 and R_3 are independently hydrogen, -R_5-OH
or C_1_-_4 alkyl, R_4 and R_5 are independently 1,2-ethylene or 1,2-propylene, and n is 2 or 3
and an alkanolamine of the formula R-
COOH II where R is C_1_1_-_2_1 alkyl, C_1_1_-
_2_1 alkenyl, hydroxy substituted C_1_1_-_
A sulfomethylated amino-ester which is a 2_1 alkyl or a C_1_1_-_2_1 alkenyl or a mixture of such alkyl and alkenyl and is the sulfomethylation product of the reaction product of with a fatty acid or a functional derivative thereof. 2. The sulfomethylated amino-ester of claim 1, wherein R_4 or R_5 is 1,2-ethylene. 3, R is C_1_3_-_2_1 alkyl, C_1_3
3. The sulfomethylated amino-ester of claim 1 or 2 which is a ____2_1 alkenyl or a mixture thereof. 4. Amino ester has the formula III R-CO-O-R_4-NHR_1_0 III where R_1_0 is hydrogen, -R_5-OH, -R_5-O-C
OR or -(CH_2)-_nNR_2_0R_3
_0, and R_2_0 is hydrogen, C_1_-_4 alkyl, -CO-R, -R_5-OH or -R_5-O-
CO-R, or R_3_0 is hydrogen, C_1_
-_4 alkyl, -R_5-OH or -R_5-O-
Sulfomethylated amino- ester. 5, Formula IV R-CO-O-R_4-N(R_1_1)-CH_2-
SO_3M IV In the formula, R_1_1 is C_1_-_4 alkyl, -R_5-OH
, -R_5-O-CO-R, -CH_2-SO_3M,
-(CH_2) -_nNHR_2_1, -(CH_2)
-_nN(R_2_2)-CH_2-SO_3M or -(CH_2)-_nNR_2_2R_2_3,
R_2_1 is hydrogen, -R_5-OH, C_1_-_4 alkyl, -CO-R, -CH_2-SO_3M or -
R_5-O-CO-R, and R_2_2 is C_1_-
_4 alkyl, -R_5-OH, -R_5-O-CO-
R or -CH_2-SO_3M, R_2_3 is C_1_-_4 alkyl, -R_5-OH
or -R_5-O-CO-R, M is hydrogen or a cation equivalent, and R, R_
4, R_5 and n are as defined in claim 1. A sulfomethylated amino-ester according to any one of claims 1 to 4. 6, Formula IVa R′-CO-O-CH_2-CH_2-N(R_1_2
)-CH_2-SO_3M IVa In the formula, M is hydrogen or an equivalent of a cation, and R' is a linear or branched primary C_1_7-_1
_9 alkyl or a mixture of such alkyls and R_1_2 is hydrogen, -CH_2CH_2-OH, -CH
_2-CH_2-O-CO-R' or -CH_2-S
The sulfomethylated amino-
Esters or mixtures thereof. 7. A sulfomethylated amino-ester according to any of claims 1 to 6, wherein the amino-ester is a reaction product of diethanolamine and a mixture of stearic acid/isostearic acid. 8. The sulfomethylated amino-ester according to claim 7, wherein the weight ratio of the stearic acid/isostearic acid mixture is from 65/35 to 35/65. 9. An alkanolamine of the formula I HO-R_4-NHR_1 I where R_1 and R_2 are as defined in claim 1, or a mixture thereof, of the formula II R-COOH II where R is as defined in claim 1, and reacts the unacylated primary and/or secondary amino groups of the resulting amino-ester with formaldehyde or formaldehyde. Claims 1 to 8 characterized in that the product compound and the sulfite are sulfomethylated with SO_2 or a compound of the formula V HO-CH_2-SO_3M V where M is hydrogen or an equivalent of a cation.
A method for producing a sulfomethylated amino-ester according to any of the preceding paragraphs. 10. A fatty acid of formula II is converted into an alkanolamine of formula I.
10. A process according to claim 9, wherein the reaction is carried out in an amount of at least 0.5 mol per mol. 11. The method of claim 10, wherein the alkanolamine of formula I is diethanolamine and the molar ratio of diethanolamine to fatty acid of formula II is from 1:0.5 to 2. 12. A process according to any of claims 9 to 11, wherein formaldehyde, a formaldehyde-generating compound or a compound of formula V is used in an amount of at least 0.2 mol/amine value. 13. The process according to claim 12, wherein formaldehyde, formaldehyde-generating compounds or compounds of formula V are used in an amount of 0.2 to 2.0 mol/amine value. 14. The molar ratio of sulfite or SO_2 to formaldehyde or formaldehyde-generating compounds is 1 to 1.1:
1. The method according to any one of claims 9 to 13. 15, a sulfomethylated amino-ester substantially as described below with reference to Examples 1-12. 16. A method for finishing a fiber support, characterized in that it comprises applying a sulfomethylated amino-ester according to any one of claims 1 to 8 and 15 to the fiber support. 17. The method according to claim 16, wherein the support is a paper or fibrous support made of natural or regenerated cellulose. 18. A method according to claim 16 or 17, wherein said finishing is carried out simultaneously with or after optical whitening of said support. 19. The concentration of sulfomethylated amino-ester on the support is between 0.3 and 10, based on the dry weight of the support.
19. The method according to any one of claims 16 to 18, wherein 20. A method substantially as hereinafter described with reference to any one of Examples AC. 21. An aqueous composition characterized in that it contains from 3 to 50% by weight of the sulfomethylated amino-ester according to any one of claims 1 to 8 and 15. 22. The aqueous composition according to claim 21, further comprising a nonionic surfactant. 23. Nonionic surfactants have an average HLB of 6 to 19.
23. The aqueous composition of claim 22 having the value. 24. The nonionic surfactant is ethylene oxide (E
O) and/or propylene oxide (PO) in saturated and/or unsaturated linear and/or branched fatty alcohols, alkylphenols, fatty acids, fatty acid alkanolamides, partial fatty acid esters of polyols, and plants. products obtainable by addition to natural or animal fats or oils; partial fatty acid esters of polyols; EO/P with high EO content;
24. Aqueous composition according to claim 22 or 23, selected from O copolymers (fluronic type); EO/PO addition products to ethylenediamine with high EO content (tetronic type) or mixtures thereof. 25. The nonionic surfactant is of formula VI or VIIR_6
-(OCH_2CH_2)-_pOH VI(R_7-C
O)_q-X VII In the formula, R_6 is C_9_-_2_4 alkyl, C_9_-_2
_4 alkenyl or a group of formula (a) ▲There are mathematical formulas, chemical formulas, tables, etc. ▼ (a) Each R_7 is independently C_1_1_-_1_9 alkyl or C_1_1_-_1_9 alkenyl or a mixture thereof, and R_8 is C_4_-_1_2 alkyl; is 1 or 2, r is 1 or 2, and s is 3 to 60, polyethoxylation products of compounds of formula VII,
or a mixture thereof, the aqueous composition according to claim 24. 26. Based on the weight of the sulfomethylated amino ester,
26. Aqueous composition according to any of claims 22 to 25, comprising 3 to 50% by weight of nonionic surfactant. 27, an aqueous composition substantially as hereinafter described with reference to Examples 1-12. 28. Fibers from an aqueous finishing fluid according to any of claims 16 to 19 using said sulfomethylated amino-ester in the form of a composition according to any of claims 21 to 27. How to finish the material.