US3776767A

US3776767A - Process for improving the crease resistance and the abrasion resistance of a textile material

Info

Publication number: US3776767A
Application number: US00104142A
Authority: US
Inventors: A Buehler; H Schuetz; D Maeusezahl; M Harris; C Guth
Original assignee: Ciba AG
Current assignee: BASF Schweiz AG
Priority date: 1967-10-24
Filing date: 1971-01-05
Publication date: 1973-12-04
Anticipated expiration: 1990-12-04
Also published as: CH480488A; IL30837A; GB1235307A; CH469043A; BE722763A; DE1803087B2; IL30837A0; DE1803087A1; SE340888B; CS151484B2; NL6815153A; CH1482667A4; FR1595640A

Abstract

This invention provides new condensation products which are obtained by reacting a monocyclic or dicyclic heterocyclic compound having 5 to 7 ring members, at least two members being nitrogen and at least two halogen atoms being linked directly with the carbon atoms of the hetero ring, with a thiourea compound, an alkali metal or ammonium hydrogensulfide and a monoor dialkanolamine. These condensation products are useful in combination with aminoplast precondensates for improving the crease resistance and the abrasion resistance of a textile material.

Description

United States Patent [1 1 Buehler et a1.

[ PROCESS FOR IMPROVING THE CREASE RESISTANCE AND THE ABRASION RESISTANCE OF A TEXTILE MATERIAL [75] Inventors: Arthur Buehler, Rheinfelden; Hans Ulrich Schuetz, Basel; Dieter Maeusezahl, Allschwil; Melvin Harris, Arlesheim; Christian Guth, Basel, all of Switzerland [7 3] Assignee: Ciba Limited, Basel, Switzerland [22] Filed: Jan. 5, 1971 [21] Appl. No.: 104,142

Related US. Application Data [63] Continuation of Ser. No. 768,495, Oct. 17, 1968,

abandoned. I

[30] Foreign Application Priority Data Oct. 24, 1967 Switzerland 14826/67 52 us. (:1. 117/139.4, 117/138.8 F, 117/1395 A, 117/143 A 51 Int. Cl D06m 13/00 [58] Field of Search 117/1394, 139.5 A, 117 143 A, 138.8 F; 260/2498, 249.5, 249.6

[56] References Cited UNITED STATES PATENTS 2,561,973 7/1951 Cohen 117/139.4X

[4 1 Dec.'4, 1973 2,573,525 10/1951 West 260/2498 X 2,684,346 7/1954 Nickerson 117/1394 X 2,990,298 7/1961 Moyse et al. 117/1395 A 3,028,264 4/1962 Frick l17/139.4 3,054,792 9/1962 Howard et al. 260/2498 X Primary Examiner-Murray Katz Assistant ExaminerTheod0re G. Davis Attorney-Harry Goldsmith, Joseph G. Kolodny, Bryant W. Brennan and Edward .1. Sites [57] ABSTRACT 6 Claims, No Drawings I PROCESS FOR IMPROVING THE CREASE RESISTANCE AND THE ABRASION RESISTANCE OF A TEXTILE MATERIAL This application is a continuation of Ser. No. 768,49- 5, filed Oct. 17, 1968, and now abandoned.

It has been found that valuable new condensates are obtained that are capable of substantially counteracting the impairment of the mechanical properties occurring when finishing cellulosic textile materials with aminoplasts, when in an aqueous medium at a temperature from l to +30 C, in each case at a molecular ratio ofl :2 to 1 10.5, preferably from 1 1.5 to 1 10.5, a colourless heterocyclic compound that contains at least 2 nitrogen atoms in the hetero ring and at least 2 halogen atoms linked with carbon atoms of the hetero ring, is reacted with A. a thiourea compound that contains at least one hydrogen' atom linked with nitrogen, preferably thiourea itself, or with an alkali metal or ammonium hydrogensulphide and B. a monoor di-alkanolamine containing 1 to 4 carbon atoms, preferably with monoor diethanolamine, the reaction is then finalized at a temperature from 30 to 100 C, preferably from 45 to 70 C and, if desired, water is distilled out of the mixture formed.

The heterocyclic compound used as starting material in the present process must be practically colourless and contain at least one, preferably only one, heterocycle which may be altogether the only ring of the compound or, for example, may also contain a fused-on aromatic six-membered' ring. Specially useful are compound with six-membered hetero rings, especially those whose ring contains 2 or 3 nitrogen atoms and 4 or 3 carbon atoms, such as pyridazine, pyrimidine, quinazoline and especially 1,3,5-triazine compounds. These compounds contain at least 2 halogen atoms linked with carbon atoms of the hetero ring, for example bromine or preferably chlorine atoms. As relevant examples there may be mentioned trichlorpyrimidine, tetrachloropyrimidine, 2,4-dichloroquinazoline, 2,4,6-tribromo-l,3,5-triazine and in the first place 2,4,6-trichloro-l,3,5-triazine (cyanuric chloride).

As further starting materials there are required a thiourea compound containing at least one hydrogen atom linked with nitrogen, or preferably thiourea itself or an alkali metal or ammonium hydrogensulphide, as well as a monoalkanolamine or dialkanolamine containing l to 4 carbon atoms, preferably monoor diethanolamine.

The reaction is performed in an aqueous medium that may contain apart from water organic solvents, especially those which are water-miscible. There may be mentioned lower alcohols and acetone.

No specific sequence of the reaction stages is prescribed, that is to say the heterocyclic compound may be reacted first with the sulphur-containing compound or first with the alkanolamine.

Forthe reaction'of every mol of component (A) or (B) with the heterocyclic compound 1 mol of alkali or a slight excess in form of an aqueous alkali metal hydroxide'or carbonate solution is added to the reaction mixture, either in one lot or portionwise.

The reactions are performed within the temperature range from --l0 to +30 C; in the presence of an organic solvent the reaction temperature may be below 0 C, whereas when purely aqueous reaction media are used it is advantageous to react at 0 C or slightly higher.

It is advantageous to start with the second reaction step in each case only after the first reaction is substantially complete; this is approximately the case when after addition of the alkali, or of its last portion, the reaction medium reveals a pH value of about 7. The reaction is then finalized at a temperature from 30 to 100 C, preferably from 40 to 70 C, and may be terminated after 2 to 3 hours. The pH value of the reaction mixture during this time should be within the neutral or slightly alkaline region. A dropin pH value impairs the solubility of the reaction product substantially and can be prevented by adding more alkali. The condensates are also obtained, when in an aqueous medium at a temperature from 10 to +25? C at a pH value from 6 to 9 and at a molecular ratio from I 1.5 to l 0.5, a colourless heterocyclic compound that contains at least 2 nitrogen atoms in the hetero ring and at least 2 halogen atoms linked with carbon atoms of the hetero ring, is reacted with a thiourea compound and on completion of this first reaction stage, without intermediate separation, for every mol of heterocyclic halogen compound used 0.5 to 1.5 mols ofa monoalkanolamine'are added, while maintaining a pH value from 6 to 10 and keeping the temperature of the reaction medium first for at least 8 hours at 30 to C and then for at least 5 hours at to C and, if desired, the water is distilled out of the mixture formed.

When the starting material used is cyanuric chloride, then, in general, for 1 mol each of this halogen compound a total of about 4 mols of monoacidic base, thus for instance 3 mols of alkali metal hydroxide and lmol of alkanolamine, is consumed. The amount of water used as reaction medium may be freely chosen within a wide range, advantageously so that, on one hand, the reaction mixtureis easy to stir from the start and the risk of heating beyond the prescribed temperature range is obviated and that, on the other hand, excessive dilution does not make the practical performance problematic. Since as a rule the heterocyclic halogen compounds are sparingly soluble in the water serving as reaction medium, it is advantageous first to convert them into a finely distributed state, which can be done in known manner by dissolution in an organic watermiscible solvent such as acetone and pouring the solution out over ice, As mentioned above, the molecular ratio heterocyclic halogen compound sulphurcontaining compound should range from 1 2 to l 0.5, preferably from 1 11.5 to l 0.5, and the molecular ratio of heterocyclic halogen compound alkanolamine should likewise be within the range from 1 2 to 1 0.5, preferably from 1 l.5 to l 0.5. Especially with cyanuric chloride particularly good results are obtained by using equimolecular proportions or amounts of the three reactants differing only little therefrom.

On completion ofthe reactionthe resulting product can be used as it is for thepurpose indicated above. In view of the concentration of the mixture, which is not very high at the end of the reaction, it is, however, advisable to remove the water completely or partially by distillation under vacuum. In this manner generally stable products are obtained which are at most only slightly tinted and are readily and completely soluble in water.

The products obtained by the process described above are suitable, as has already been said, for use in combination with aminoplasts in textile finishing, especially for improving the shape retention. Particularly suitable for such a treatment is textile material of cellulose, if desired in combination with other fibres, for example polyester fibres. Therefore, according to a preferred use of the products of this invention textile materials are impregnated with an aqueous preparation containing a curable aminoplast precondensate, a curing catalyst and a condensate of the composition defined above, whereupon the textile material is dried and hardened by treatment at an elevated temperature.

Aminoplast precondensates are adducts of formaldehyde with methylolable nitrogen compounds. In this connection there may be mentioned amino-1,3,5- triazines such as N-substituted melamines, for example ammeline, guanamines, for example benzoguanamine or acetoguanamine. Further suitable are symmetric alkyltriazones, biuret, thiourea, alkylcarbamates, guanidine, alkylor aryl-ureas and -thioureas, alkylene ureas or diureas, for example ethyelne urea, propylene urea or acetylene diurea; 4,5-dihydroxy-imidazolidone-2 and its derivatives, for example the 4,5-dihydroxyimidazolidone-Z substituted in 4-position on the hydroxyl group by the residue CH CH CON- H-CH -OH. The methylol compounds of urea and of melamine are preferred and in the case of melamine compounds those ofa low or high degree of methylolation may be used. It is also possible to use compounds whose methylol groups are more or less completely etherified, for example, with methyl groups.

As curing catalysts the conventional acid or potentially acid compounds may be used, such as ammonium chloride, magnesium chloride or zinc fluoroborate.

Particularly valuable results are also obtained when the preparation used for finishing the textile materials contains in addition to the aminoplast precondensate, the curing agent and the condensate of this invention also an emulsion polymer prepared from an N- methylolamide of an a,B-ethylenically unsaturated carboxylic acid or an ether of such a methylolamide and an alkaline earth metal salt of an a,,B-ethylenically unsaturated monocarboxylic acid, especially the copolymers, obtained in an aqueous emulsion, from a. 0.25 to percent by weight of an alkaline earth metal salt of an a,,B-ethylenically unsaturated monocarboxylic acid (for example calcium acrylate),

b. 0.25 to 30 percent by weight of an N- methylolamide or N-methylolamide ether of an a,B-unsaturated monoor dicarboxylic acid (for example acrylic acid methylolamide, methacrylic acid methylolamide or the methyl ethers of these methylolamides),

c. 99.5 to 60 percent by Weight of at least one further copolymerizable compound, for example an ester of acrylic or methacrylic acid and an alkanol such as methanol, ethanol, n-butanol, acrylic acid tertiary butylamide, vinylidenechloride, vinylacetate, acrylonitrile, styrene.

Depending on the purpose to be served by the finish the aqueous preparations may contain further ingredients, for example hydrophobizing agents, suitable optical brighteners, wetting agents, dispersants or flameproofing agents, especially phosphorus compounds such as dialkylphosphono-propionic acid methylolamides. In very many cases it is also advisable to add, for example, a nonionic agent that produces a soft handle,

for example an aqueous emulsion of a methylolmelamine alkyl ether modified by stearic acid alkylolamide residues.

The proportions of the ingredients of the aqueous preparations may vary within wide limits and may be adapted to the purpose in hand. In general it is indicated to use for 10 parts of aminoplast precondensate 1 to 4 parts of condensate from heterocyclic halogen compound, thiourea and alkanolamine. Otherwise, the textile material may be treated in the usual manner. For example, undyed or dyed fabric or tricot may be impregnated on a padder with the preparation and, advantageously after an intermediate drying operation at a temperature of up to 100 C, subjected to a treatment with dry heat of l-l80 C for 2 to 20 minutes, the temperature and the duration of the treatment being adapted to the purpose of the treatment which may be, for example, an improvement of the wet fastness properties for direct dyeing dyestuffs, an anti-crease finish or permanent shaping (permanent press). The finishing operation may also be combined with a dyeing operation, for example so that the impregnating solution further contains a dyestuff which, by virtue of special substituents, is reactive towards the fibre or more especially towards the aminoplast precondensate and, by virtue of this property, is fixed on the substrate during the heat treatment or even before it.

As is known an aminoplast resin finish impairs the mechanical properties of cellulosic fibrous materials, especially their tensile strength and abrasion resistance; in general the loss in strength is the greater the higher the content of aminoplast and the more energetic the hardening is. As mentioned above, these serious drawbacks can be substantially prevented with the aid of the new condensates or at least they can be reduced to an acceptable degree. In addition it has been observed that these condensates improve the soil release from the fibre.

Example 1 A solution of 190 g (1 mol) of cyanuric chloride in 1 litre of acetone is poured over a mixture of 1 litre of water and 1 kg of ice and the precipitated cyanuric chloride is filtered off. The paste is introduced into a solution which has been prepared at C from 76 g (1 mol) of thiourea and one-half litre of water and has then been cooled by adding one-half kg of ice. By dropping in a 5N-sodium hydroxide solution the pH value is maintained at 6.7 to 6.9 during this first condensation stage and the temperature is maintained at 8 to 10 C by indirect cooling. After about 5 hours and a consumption of about 3.5 mols of sodium hydroxide the pH value remains constant, and practically everything is dissolved in the reaction mixture. Then one lot of 61 g (1 mol) of monoethanolamine is added and the solution, which is now clear, is heated in a second condensation stage for 15 hours at 35 to 40 C and in a third stage for 8 hours at to C. During this time further sodium hydroxide solution is added as and when required so that the pH value remains constant at 7.0, for which about 0.5 mol of sodium hydroxide is needed. Finally, the solution is evaporated to dryness at to C under vacuum and the residue is ground in a ball mill, to furnish 410 g of a faintly yellowish, readily water-soluble hygroscopic powder condensate A.

. 5 Apart from product A the following Table lists further condensates obtained in this manner, together with the appropriate data for their manufacture:

g (0.05 mol) of anhydrous sodium carbonate in 15 ml of water during 1 hour the pH value of the reaction mixture is maintained at about 7.

TABLE I Quantity in mols 1st stage 2nd stage 3rd stage Working up E= Cyan- Ethevaphrate uric ThlanolpH- pH- pH- in a uo chloride ourea amine Temp. Hours value Temp Hours value Temp. Hours value at C.

A 1 1 1 8-10 5 6. 76.0 35-40 15 7 55-60 8 7 E -100 B. 1 1 1 0-10 8 6.0-6. .35-40 14 7 55-60 J 7 E 00-100 C 1 1 1 0-12 2 8-9 35-40 15 7 55-60 8 7 E 90-100 D 1 1 1 0-10 4% 7 35-40 15 7 55-60 8 7 E 90-100 E 1 1 1 0-8 5 7 35-40 14 7 55-60 0 7 E 00-100 F 1 1.5 0.5 0-10 8 7 35-40 13 7 55-60 7 7 E 00-100 G 1 0. 5 1. 5 0-10 22 7 35-40 22 7 55-60 8 7 H 2 2 2 0-12 14 7 35-40 18 7 55-60 8 7 E 90-100 1 Filter off insol. residue then E 90-100.

E l 2 Then 7.6 g (0.1 mol) of thiourea and 20 ml (0.1 mol) A solution of 18.5 g (0.1 mol) of cyanuric chloride in 100 cc of acetone is poured out over a mixture of 0.1 litre of water and 0.1 kg of ice, and the precipitated cyanuric chloride filtered off. The paste is introduced into a solution which has been prepared at 45 C from 7.6 g (0.1 mol) of thiourea and 50 ml of water and then cooled by adding 50 g of ice'thereto. in this first condensation stage the pH value is maintained at 6.7 to 6.9 by dropping in a SN-sodium hydroxide solution and the temperature is kept at 8 to C by indirect cooling.

After about 5 hours and a consumption of about 3.5 mols of sodium hydroxide the pH value remains constant and practically all has dissolved in the reaction mixture. One lot of 10.5 g (0.1 mol) of diethanolamine is then added and the reaction mixture heated to 55 to 60 C while adding another 10 ml of 5N-sodium hydroxide solution (0.05 mol) and then heated at this temperature with stirring for 5 hours. i

The solution is then evaporated to dryness at 60 C under vacuum, to yield 46 g of a pale yellowish, readily water-soluble powder: condensate J.

Example 3 A suspension of 18.5 g (0.1 mol) of cyanuric chloride in 100 ml of alcohol is cooled to 5 to 10 C. One lot of 6.1 g (0.1 mol) of monoethanolamine is added; dur ing minutes m1 of SN-sodium hydroxide solution (0.1 mol) are dropped in and the reaction mixture is stirred for about 1 hour at the same temperature until a constant pH value of about 2.7 has been established.

On addition of 7.6 g (0.1 mol) of thiourea and 30 ml of 5N-sodium hydroxide solution (0.15 mol), in each case in one lot, the pH value of the reaction mixture temporarily reaches 1 l which'drops again to 7 after another 30 minutes reaction, during which the temperature is raised to 30 to 40 C. Then another 20 ml of SN-sodium hydroxide solution are added and the reaction terminated after stirring for 2 /2 hours.

The resulting colourless suspension is evaporated to dryness at 40 C under vacuum, to leave 40 g of a pale yellow, readily water-soluble product: condensate K.

Example 4 v 18.5 Grams (0.1 mol) of cyanuric chloride are suspended in 200 ml of a mixture of 100 ml of water and 100 ml of acetone and at 0 C 6.1 g (0.1 mol) of monoethanolamine are added in one lot. By dropping in 5.3

of SN-sodium hydroxide solution are added. When the pH value has dropped to 7, the temperature is raised to 50 C and the reaction finalized by stirring for minutes, during which another 40 ml (0.2 mol) of 5N- sodium hydroxide solution are gradually added. The resulting reaction mixture is evaporated to dryness under vacuum, to yield 40 g of a readily water-soluble condensate: condensate L.

Example 5 A suspension of 18.5 g (0.1 mol) of cyanuric chloride in ml of water is mixed within 60 minutes at 0 C with 14.35 ml (0.1 mol) of a 39.1 percent solution of sodium hydrosulphide.

The resulting yellow suspension is mixed' at room temperature with 6.1 g (0.1 mol) of monoethanolamine and then with one lot of 20 ml (0.1 mol) of 5N-sodium hydroxide solution. The batch is then heated to 50 C and heated and stirred at this temperature for about 2 hours. After this time the reaction mixture reveals a pH value of about 7.

Another 20 ml (0.1 mol) of 5N-sodium hydroxide are added and the reaction continued for 3 hours at the same temperature, whereupon it is terminated, and the pH value adjusts itself at 10. The reaction mixture is first filtered to remove the insoluble components (5.5 g of a yellowish substance) and the filtrate is then evaporated to dryness at 60 C under vacuum, to yield 26.5 g of a white powder: condensate M.

Example 6 Aqueous padding liquors are prepared with the use of the substances listed below:

a. Aminoplast precondensate 50 percent aqueous solution of a mixture of dimethylolethylene urea and methyl ether of a highly methylolated melamine.

b. Softening agent 30 percent aqueous dispersion of a methyl ether (modified with stearic acid alkanolamides) of a highly methylolated melamine.

c. Copolymer 27 percent aqueous emulsion of a copolymer from 80 parts of acrylic acid n-butyl ester, 13 parts of vinylidenechloride, 6 parts of acrylic acid methylolamide and 1 part of calcium acrylate.

d. Condensate prepared as described in Example 1 from cyanuric chloride, thiourea and monoethanolamine: condensate A.

Mercerised and bleached cotton popelin is then impregnated with padding liquors, whose composition is TABLE II (a) Aminoplast precondens e,g. (b) Softening agent, gJl (c) Copolymer emulsion,

(d) Condensate A, g./l M 'Cl2-6lI20, tl./l C 'I;CO01'I,40% g. pH of padding liquor Tens. strength, percent Abrasion res, percent Crease resist. in Crease angle, wet in HN-CHz-CIhS O aNa number of abrasive rotations (n) are counted that are needed to hole the tested material, after having ascertained this number with untreated material (in). From the results obtainedthe abrasion resistance values (A) of the treated fabric specimens are calculated: A lOOn/m. (3), (4) To determine the crease angle dry and evenly moistened rectangular pieces of fabric, cut diagonally across the fibres, measuring 16 mm X 44 mm are folded parallel to the short side, placed in between glass plates and loaded with 2 kg-weights. After 5 minutes loading and l hours recovery the test specimens are introduced into an angle measuring instrument of conventional design and the crease angle is measured.

Example 7 Mercerized cotton popelin is impregnated with the liquors of this composition, then dried at 60 to 80 C and heated for 13 minutes at 170 C. The fabric is then washed for 5 minutes in a boiling 0.2 percent sodium carbonate solution, rinsed in cold water and dried.

TABLE III.

(a) Aminoplast precondensate, g./l 140 140 140 30 nil-value of padding liqu0r. 5.1 Tensile strength, percent 52 Abrasion resistance, percent 48 Crease angle, dry, in degrees 132 Crease angle, wet, in degrees 4 11!) NOTE.Concerning 1, 2, 3 and 4: The measuring of these vulues has been explained following upon Table 11.

Example 8 Aqueous padding liquors are prepared with the use of the under-mentioned substances:

a. Aminoplast precondensate 50 percent aqueous solution ofa mixture of dimethylol-ethylene urea and methyl ether of a highly methylolated melamine.

d. Wetting agent 25 percent aqueous solution of an adduct of p-nonylphenol with 9 mols of ethylene oxide.

e. Brightening agent of the formula S OaNa (LCM f. One of the following condensates:

l. Condensate from cyanuric chloride, thiourea and monoethanolamine, prepared according to Example I: condensate A.

2. Condensate from cyanuric chloride, monoethanolamine and thiourea, prepared according to Example 3: condensate K.

3. Condensate from cyanuric chloride, sodium hydrogensulphide and monoethanolamine, prepared according to Example 5: condensate M.

g. Magnesium chloride hexahydrate (MgCl '6H O).

Mercerized and bleached cotton popelin is impregnated with padding liquors composed as shown in Tables IV, V and V1 to a weight increase of 60 percent referred to the original weight of the fabric. After having been dried at 60 to 80 C the fabric is heat-treated for 4% minutes at C, then washed for 5 minutes in a boiling 0.2 percent sodium carbonate solution, rinsed in cold water and dried.

TABLE IV TABLE IV I Continued (g) MgClz-fiHzO, g./l 15 15 15 pH-value of the padding liquor 5. 9 5.9 5. 9 5. 9 Tensile strength, percent .100 63 69 Abrasion resistance, percent 2 100 19 59 39 103 Crease angle in degrees:

Dry 3 53 133 122 130 127 (b) Wei; 4 65 116 121 124 126 Nornto These values are measured as described following Table TABLE V (a) Aminoplast precondensate, g./l 150 15 (b) Softening agent, g./l 1 30 30 30 39 (e) Copolymer emulsion, g.ll 40 40 (d) Wetting agent, g./l t t. 3 3 3 3 (e) Brightening agent, g./l. 3 3 3 3 (i) Condensate K, g./l a a 5 (g) MgClz-fiHzO, g./l 15 15 15 15 pH-value of the padding liquor 5. 9 5. 9 5. 9 5.9 Tensile strength, percent 100 63 69 63 72 Abrasion resistance, percent 2 100 19 55 39 8B Crease angle in degrees- Dry 3 53 133 123 130 120 (b) Wet 65 116 120 124 117 Norato These values are measured as described following Table 11.

TABLE VI (a) Aminoplast precondensate, g./l 150 150 150 150 (b) Softening agent, g./l 30 30 30 30 (c) Copolymer emulsion, g./l 40 40 (d) Wetting agent, g./l 3 3 3 3 (e) Brightening agent, g./l-. 3 3 3 3 (f) Condensate M, g./l 10 (g) MgClzJiHzO, g-ll 15 -15 15 pH-velue of the padding liquor. 5. 9 5. 9 5.9 5. 9 Tensile strength, percent 1 100 63 59 63 71 Abrasion resistance, percent 2 100 19 48 39 94 Crease angle in degrees:

Dry 5 53 133 119 130 127 (1)) Wet 65 116 119 124 126 IINo'rE. to These values are measured as described following Table We claim: 1. In the process for improving the crease resistance and the abrasion resistance of a textile material by impregnation with an aqueous preparation containing a thiourea, sodium-, potassiumand ammonium hy- I drogensulfide, and

C. a member selected from the group consisting of a monoalkanolaminc and a dialkanolamine with l to 4 carbon atoms in an aqueous medium at a temperature from about 10 to 30 C at a molecular ratio for (B) as well as for (C) from l:2 to 1:05, then finalizing the reaction at temperatures from 30 to C and removing water from the resulting mixture by distillation.

2. Process according to claim 1, wherein the initial alkanolamine used to obtain the condensation product is monoethanolamine or diethanolamine.

3. Process according to claim 1, wherein to obtain the condensation product the molecular ratio of cyanuric chloride to component (B) and (C) is from 1:15 to 1:05.

4. Process according to claim 1, wherein the aminoplast precondensate is a methylol compound of urea or melamine.

5. Process according to claim 1, wherein the impregnating the textile material condensation product is obtained by reacting cyanuric chloride with A. thiourea in an aqueous medium at a temperature from about- 10 to 25 C and at a-pH- value from 6 to 9 at a molecular ratio of 121.5 to 1:0.5 and, without intermediate separation with (B) 0.5 to 1.5 mols of a monoalkanolamine with l to 4 carbon atoms for every mol of cyanuric chloride, maintaining a pH-value from 6 to 10, keeping the temperature of the reaction for at least 8 hours at 30 to 50 C and then for at least 5 hours at 60 to 65 C, and removing water from the resulting mixture by distillation.

6. Process according to claim 1, wherein the aminoplast precondensate comprises an adduct of formaldehyde with a nitrogen compound reactable therewith to form an N-methylol group, the curing catalyst is an acid or potentially acid compound, drying is effected at a temperature up to 100 C and heating is effected with dry heat at a temperature from to C for 20

Claims

2. Process according to claim 1, wherein the initial alkanolamine used to obtain the condensation product is monoethanolamine or diethanolamine.
3. Process according to claim 1, wherein to obtain the condensation product the molecular ratio of cyanuric chloride to component (B) and (C) is from 1:1.5 to 1:0.5.
4. Process according to claim 1, wherein the aminoplast precondensate is a methylol compound of urea or melamine.
5. Process according to claim 1, wherein the impregnating the textile material condensation product is obtained by reacting cyanuric chloride with A. thiourea in an aqueous medium at a temperature from about-10* to 25* C and at a pH- value from 6 to 9 at a molecular ratio of 1:1.5 to 1:0.5 and, without intermediate separation with (B) 0.5 to 1.5 mols of a monoalkanolamine with 1 to 4 carBon atoms for every mol of cyanuric chloride, maintaining a pH-value from 6 to 10, keeping the temperature of the reaction for at least 8 hours at 30* to 50* C and then for at least 5 hours at 60* to 65* C, and removing water from the resulting mixture by distillation.
6. Process according to claim 1, wherein the amino-plast precondensate comprises an adduct of formaldehyde with a nitrogen compound reactable therewith to form an N-methylol group, the curing catalyst is an acid or potentially acid compound, drying is effected at a temperature up to 100* C and heating is effected with dry heat at a temperature from 140* to 180* C for 20 to 2 minutes.