US3597147A

US3597147A - Modification of cellulosic textile materials with pyrimidones

Info

Publication number: US3597147A
Application number: US868221A
Authority: US
Inventors: Heinz Bille; Harro Petersen; Martin W Schwemmer; Hans Bors
Original assignee: BASF SE
Current assignee: BASF SE
Priority date: 1968-10-24
Filing date: 1969-10-21
Publication date: 1971-08-03
Anticipated expiration: 1988-08-03
Also published as: FR2021447A7; DE1804806A1; GB1278614A; US3609916A; NL6916099A; CH1537569D; BE740743A

Abstract

THE USE OF N1-MONOHYDROXYMETHYL AND N-1-MONOALKOXYMETHYL DERIVATIVES OF 5,5-DIALKYLHEXAHYDROPYRIMIDONES WHICH BEAR AN ALKYL GROUP IN THE N3-POSITION AND A HYDROXYL OR ALKOXYL GROUP IN THE 4-POSITION AS FINISHING AGENTS FOR TEXTILE MATERIAL CONSISTING OF OR CONTAINING NATURAL OR REGENERATED CELLULOSE.

Description

United States Patent 3,597,147 MODIFICATION OF CELLULOSIC TEXTILE MATERIALS WITH PYRIMIDONES Heinz Bille, Limburgerhof, and Harro Petersen, Frankenthal, Germany, and Martin W. Schwemmer, Urdorf, and Hans Bors, Fallanden, Switzerland, assignors to Badische Anilin- & Soda-Fabrik Aktiengesellschaft, Ludwigshafen (Rhine), Germany No Drawing. Filed Oct. 21, 1969, Ser. No. 868,221 Claims priority, application Germany, Oct. 24, 1968, P 18 04 806.1 Int. Cl. C07d 51/18; D06m 13/40, 13/52 U.S. Cl. 8116.3 4 Claims ABSTRACT OF THE DISCLOSURE The use of N -monohydroxymethyl and N -monoalkoxymethyl derivatives of 5,5 dialkylhexahydropyrimidones which bear an alkyl group in the N -position and a hydroxyl or alkoxyl group in the 4-position as finishing agents for textile material consisting of or containing natural or regenerated cellulose.

The present invention relates to the use of unetherified or etherified N -monomethylol compounds of N -alkyl-4- hydroxyor N -alkyl-4-alkoxy-5,5-dialkylpropylenureas (N -alkyl-4-hydroxyor N -alkyl-4-alkoxy 5,5 dialkylhexahydropyrimidones-(2)) as finishing agents for textile material consisting of or containing natural or regenerated cellulose.

It is known that substances having the general formula:

where R to R denote hydrogen atoms or low molecular Weight alkyl radicals can be used as finishing agents for textile material consisting of or containing natural or regenerated cellulose. Those of these prior art finishes have proved very suitable in practice in which R and R denote alkyl radicals because in the dry condition they are particularly resistant to acid and potentially acid catalysts conventionally used in textile finishing and because the effects obtainable therewith do not impair the light fastness of dyeings and have good resistance to washing, fastness to chlorine and abrasion resistance and good resistance to hydrolysis in an acid medium. Prior art finishing agents having the Formula I have the disadvantage however that they harden the handle of the goods finished therewith in some cases.

Moreover they tend to develop a troublesome odor of formaldehyde during processing.

It is an object of the invention to finish textiles in such a way that they have a high crease resistance and at the same time a soft handle.

Another object of the invention is to avoid the odor of formaldehyde which usually occurs in the conventional textile finishing methods.

Moreover it is an object of the invention to provide textiles, without any troublesome odor of formaldehyde, with a finish which improves crease resistance, which has good resistance to washing, good fastness to chlorine and abrasion, good resistance to hydrolysis in an acid medium, which does not impair the light fastness of dyeings, which moreover is not impaired by catalyst residues and which imparts a pleasant soft handle to the material finished therewith.

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These are other objects and advantages are achieved in accordance with this invention by using as a finishing agent for textile material consisting of or containing natural or regenerated cellulose, a substance having the general formula:

R R (II) where R denotes a hydrogen atom or a low molecular weight alkyl radical, R denotes an alkyl radical having one to eighteen carbon atoms, R denotes a hydrogen atom or a radical having the formula R and R denote low molecular weight alkyl radicals and R denotes a hydrogen atom or a low molecular weight alkyl radical.

Examples of low molecular weight alkyl radicals are particularly those having up to six carbon atoms; those alkyl radicals R and R to R which have one to four, preferably one to three, carbon atoms are especially suitable. R preferably denotes a hydrogen atom.

The following may be given as example of substances having the Formula II:

The N -methylol, N -methoxymethyl, N -ethoxymethyl, N -propoxymethyl, N -butoxymethyl and N -hexyloxymethyl compounds of N -methyl-4-hydroxy-5,S-dimethylpropylenurea, N -methyl-4-methoxy-5,S-dimethylpropylenurea, N -ethyl-4-hydroxy-5,S-dimethylpropylenurea, N -butyl-4-methoxy-S-methyl-S-ethylpropylenurea, N -octyl-4-hydroxy-5,5-diethylpropylenurea, N -dodecyl-4-butoxy-5,S-dimethyl-S-isopropylpropylenurea, N -octadecyl-4-ethoxy-5-methyl-5-ethyl-6 (l-methylpropyl)-propylenurea and N -decyl-4-hydroxy-5,5-dimethylpropylenurea.

Owing to the ready accessibility of N -methylol-N -methyl-4-hydroxy-5,S-dimethylpropylenurea, N -rnethylol-N -rnethyl-4-methoxy-5,5-dimethylpropylenurea, and N -methoxymethy1-N -methyl-4-methoxy- 5,S-dimethylpropylenurea,

these are preferred. The substances having the Formula II are obtainable for example by reacting substances having the formula:

(III) where R to R have the meanings given above in an aqueous medium at a pH of more than 9 and at a temperature of from 0 to C. with an equimolar amount of formaldehyde and if desired reacting the products obtained with low molecular weight alkanols in the presence of acid-reacting catalysts and in the presence or absence of solvents and/or diluents.

Substances having the Formula III may be prepared for example by reaction of an alkylurea having the formula H NCONHR with an aldehyde having the formula:

R CHCH0 and an aldehyde having the formula R -CHO in the molar ratio 1:1:1 in aqueous solution or in an alcohol having the formula R OH and in the presence of a non oxidizin-g mineral acid at temperatures of from 30 to 120 C., R to R having the meanings given above. The substances having the Formula III are reacted with formaldehyde at a pH or more than 9, preferably within the range up to 12. The best results are achieved in the pH range from 9.0 to 11.

The pH required for the reaction may be set up in known manner with any substances or buffer mixtures having adequate alkalinity. For reasons of economy, alkali metal hydroxides, particularly sodium hydroxide and potassium hydroxide, are preferred for the purpose.

The substances having the Formula III are preferably reacted at from 20 to 80 C.; reaction temperatures of from 40 to 70 C. have proved to be particularly suitable.

The formaldehyde may be used in free form, for example as commercial aqueous formaldehyde solution, or in the form of its readily dissociable polymers such as paraformalde'hyde.

If desired the N-methylol groups formed by reaction with formaldehyde and if desired a hydroxyl group in the 4-position may be etherified with alkanols of the kind specified above. Examples of these alkanols are: methanol, ethanol, n-propanol, isopropanol, n-butanol, sec-butanol, branched amyl alcohols and octanols. Etherification is carried out in the presence of acid catalysts, preferably in the presence of medium strength or strong acids which have a dissociation constant K or K or or more such as hydrochloric acid, sulfuric acid or oxalic acid. It is particularly recommended that the amount of Water present should be as small as possible. The alcohol provided for the etherification may be used in excess so that at the same time it is used as solvent for the reactants, but other solvents and/or diluents which do not disturb the etherification may be used. The etherification reaction is preferably carried out at a moderately elevated temperature of from 40 to 60 C.

It is particularly advantageous to carry out the production of the substances having the Formula III and their reaction with formaldehyde in the same solution without isolating the substances having the Formula III. The finishing agents having the Formula II may be used for all methods used for applying N-methylol compounds to textile material: these are methods in which the material to be finished 'is impregnated with a solution or dispersion of the finishing agent and an acid or potentially acid catalyst and reacted with the finishing agent with the formation of acetal bonds between the cellulose molecules of the textile material and the finishing agent; this reaction may be carried out in the Wet condition of the textile material, or between the impregnation and the chemical reaction the textile material may be partially or completely dried and if desired stored for a prolonged period and/or made into garments in the impregnated but not yet reacted or not yet fully reacted condition.

The new finishing agents may be used in the conventional ways and preferably in the form of an aqueous impregnating liquor. The concentration of the finishing agent depends in the usual way on the desired effect. It is generally from 50 to 200 g./l. The material to be treated is impregnated with the liquor in the usual way, preferably by padding. The impregnated material may be freed by the conventional method of squeezing from excess liquor. The concentration of the liquor and the squeezing pressure are advantageously correlated so that from 1 to by weight of agent having the Formula II (calculated as pure active ingredient and with reference to the weight of the dry textile material) remains on the textile material.

The impregnated fibrous material may be dried and then heated in the presence of an acid or potentially acid catalyst to a temperature of up to 180 C., preferably to from to 160 C. The reaction is generally over Within one to six minutes under these conditions. The fibrous material may be mechanically shaped during or after drying, for example by compression, crimping, ironing, calendering, embossing or pleating. The fibrous material has a great dry crease recovery angle after reaction of the N- hydroxymethyl and/or N-alkoxymethyl groups; moreover the shape imparted to the fibrous material is washproof. When substances having the Formula II have been used whose radical R contains from ten to eighteen carbon atoms, the fibrous material is not only creaseproof but at the same time finished with a wash-resistant softener. By joint use of two substances having the Formula II of which one has a radical R with ten to eighteen carbon atoms and the other a smaller radical R the softening effect can be exactly adapted to requirements.

The treated material may be washed, rinsed and dried in the conventional manner.

There is also the very advantageous possibility of leaving the impregnated and squeezed material in the wet condition or of drying it to a moisture content of 10 to 35% (with reference to the weight of the amorphous region contained in the cellulose), i.e. in the case of natural cellulose to a moisture content of from 3 to 10.5%, in the case of regenerated cellulose to a moisture content of from 6 to 21%, in each case with reference to the weight of the entire cellulose component, and then storing it at room or elevated temperature, preferably at a temperature not higher than 50 C., without appreciable loss of water in the presence of an acid and/or potentially acid catalyst. Instead of drying the wet material to the said moisture content, it may first be completely dried and then remoistened to the said content. In a very useful method for which the substances having the Formula II have proved to be of excellent suitability, the controlled moistening is carried out by impregnating the dry textile material with an inert non-aqueous liquid which contains the small amount of water required and also the catalyst or catalysts. Reaction with the cellulose generally takes from five to twenty hours under these conditions and less at temperatures above 50 C. This embodiment of the invention makes it possible to finish fibrous material consisting of or containing cellulose in a simple and reliable manner so that it has a great to very great wet crease recovery angle of or more and a dry crease recovery angle of medium height of 110 C. or more. It is possible by varying the process conditions to adapt the size and difference between the wet and dry crease recovery angles to requirements. In this process the substances having the Formula II give finishes having improved resistance to chlorine as compared with prior art finishing agents having the Formula I.

Substances having the Formula II are also outstandingly suitable for the method of deferred or delayed curing. This is known to consist of impregnating the textile material to be finished with an aqueous solution of one or more finishing agents and one or more acid or potentially acid catalysts, drying it carefully so that the finishing agent or at least one of the finishing agents does not react or does not react to an appreciable extent, and only after a long interval, which may amount to several months, and heating to a temperature at which the finishing agent or agents react under the influence of the catalyst, so that more than one reaction may be involved which for convenience are usually referred to simply as condensation, fixing or curmg.

Deferred curing is usually employed to make use of the possibility of shaping the material to be finished in the interval between drying and curing, but particularly to make up and shape it. It may be used therefore particularly for the production of permanent press garments. Textile material in sheet form, particularly woven or knitted fabric consisting of or containing cellulose with other fibrous material, such as polyethylene terephthalate or other linear polyesters, polyamides or polyacrylonitrile is impregnated with a liquor containing the finishing agent and catalyst, with or without agents for improving handle and other additives, and carefully dried; the dry material, containing substantially unreacted finishing agent and catalyst is cut out, sewn into garments and brought into the desired shape for example by ironing, pressing or by means of shaping dummies. Then the garments, if desired while on the shaping means, are heated with saturated or superheated steam, hot air or contact heat to such an extent that the finishing agent is cured. Although subsequent washing is possible, manufacturers are anxious to avoid this operation.

The finishing agent having the Formula II may be applied to the textile material in the amounts generally used in the method of deferred curing. Amounts of from 1 to calculated on pure active ingredients and with reference to the Weight of the dry textile material have proved to be very suitable; it is preferred to apply the finishing agent in amounts of from 3 to 6%. Application of the finishing agent to the textile material is carried out in the usual way, for example by impregnating the material to be treated with an aqueous liquor in a padding machine. The material is then carefully dried so that the finishing agent is not cured prematurely; this is safely prevented by not allowing the drying temperature to rise above 100 C. The material is generally dried to a water content of from 2 to 15% by weight. The textile material may then be kept for many months and made up for example into articles of clothing.

To cure the finishing agent, the textile material is heated (if desired after fabrication and during or after shaping) to a temperature of from 120 to 200 C., preferably from 150 to 170 C. Curing under these conditions is over after from twenty to thirty minutes.

Acid and potentially acid catalysts are generally known and conventional for the purpose of crease resist finishing. Examples of these are inorganic and organic acids, such as sulfuric acid, hydrochloric acid, phosphoric acid, boric acid, formic acid, acetic acid, oxalic acid, tartaric acid, maleic acid and salts which have an acid reaction or which form acids upon the action of heat and/or by hydrolysis, for example ammonium salts and amine salts of strong acids, magnesium chloride, zinc chloride and zinc nitrate. Mixtures of more than one catalyst may also be used. It is preferred to use magnesium chloride, zinc nitrate and zinc chloride as catalysts for the method of deferred curing. The reaction of the finishing agents to be used according to this invention is carried out in the presence of these catalysts, as already described. This may be effected by applying the catalysts, preferably in the form of aqueous solutions, to the material to be finished before or after the impregnation of the same. It is preferable however to add the catalyst to the impregnating liquor containing the finishing agent. The concentration of the catalysts is chosen within the usual range for the particular finishing method used. Catalyst concentrations of from 1 to 40 g./l. and (with reference to the weight of finishing agent) amounts of catalyst of from 4 to 60%, preferably from to 40%, have generally proved to be suitable for finishing at elevated temperature and deferred curing, whereas for finishing in the swollen condition of the fiber, i.e. in the presence of considerable amounts of water, and at a low reaction temperature it may be necessary to use strongly acid catalysts in a concentration of up to 20 N.

Conventional nitrogenous and nitrogen-free hydroxymethyl or alkoxymethyl compounds, for example those of urea, thiourea, cyclic ureas, such as ethylenurea, pro pylenurea, glyoxalmonoureine, triazinones, urones, melamine and other aminotriazines, monocarbamic esters, dicarbamic esters polyethylene glycol formals and compounds containing epoxy groups, as for example glycol diglycidyl ethers, may be used together with the new finishing agents and preferably the catalysts. In deferred curing care should be taken to ensure that only those prior art finishing agents are used which during storage do not react prematurely with the cellulose. Moreover, it is possible to use conventional water-repellent, softening, level ing, wetting, and finishing agents and polymer solutions or dispersions. Water-repellents are for example paraflin Wax emulsions containing aluminum or zirconium, preparations containing silicon and perfiuorinated aliphatic compounds. Examples of softeners are oxyethylation products of high molecular weight fatty acids, fatty alcohols or fatty amides, high molecular Weight polyglycol ethers and esters of the same, high molecular weight fatty acids, fatty alcohol sulfonates, stearyl-N,N-ethyleneurea and stearyl-amide-methylpyridinium chloride. Examples of leveling agents are water-soluble salts of acid esters of polybasic acids with ethylene oxide or propylene oxide adducts of long chain oxyalkylatable substances. Examples of wetting agents are salts of alkylnaphthalenesulfonic acids, alkali metal salts of sulfonated dioctyl succinate and the adducts of alkylene oxides to fatty alcohols, alkylphenols, fatty amines and the like. Examples of finishing agents are cellulose ethers or esters and alginates, and also solutions or dispersions of synthetic polymers and polycondensates, for example polyethylene, polyamides, oxyethylated polyamides, polyvinyl ethers, polyvinyl alcohols, polyacrylic acid or esters and amides thereof and corresponding polymethacrylic compounds, polyvinyl propionate, polyvinylpyrrolidone, copolymers, for example copolymers of vinyl chloride and acrylic esters, butadiene and styrene or acrylonitrile, or a-dichloroethylene, B-chloroalkylacrylic esters or vinyl-B-ethyl ether and acrylamide or the amides of crotonic acid or maleic acid or N-methylolmethacrylamide and other polymerizable compounds. These additional assistants are generally used in amounts of from 0.3 to 4, preferably from 1 to 2.5%, with reference to the weight of dry textile material; these amounts may however be exceeded in special cases.

Finishing agents to be used according to this invention are distinguished as compared with the most nearly comparable agents by less odor of formaldehyde during processing. They give finishes which have a very high resistance to hydrolysis. Textile material thus treated is therefore extremely insensitive to acid hygienic treatments. Moreover the new agents prevent damage to the textile material by large amounts of catalyst and do not lessen the light fastness of dyeings. What is more, they give in any application a finish having excellent fastness to chlo rine and impart to the finished material a pleasant soft handle. This is particularly significant in finishing textile material made from mixtures of fibers which contain synthetic fibers; when treated with prior art agents having the Formula I these tend in particular to undergo hardening of the handle. This undesirable effect is effectively counteracted by the agents having the Formula II.

The invention is illustrated by the following examples. The parts and percentages given in the examples are by weight. The following remarks contain detailed explanations for carrying out the tests.

(1) Evaluation of samples 40 cm. x 40 cm. dried on the line according to AATCC Specification 88 Al964 T; the average of the evaluation of three samples in each case by three persons appraising independently of each other;

(2) After three minutes unloading; mean value in the warp and weft directions;

(3) According to German Standard Specification DIN 53,890: sixty minutes, mean value in warp and weft directions;

(4) According to German Standard Specification DIN 53,857: samples having the size mm. x 200 mm.;

(5) According to AATCC Specification 92l967;

(6) Washing at the boil in an automatic household washing machine (drum type) with 3 g./l. of a commercial detergent, rinsing and spin drying; (7) According to ASTM Specification D 1250-60 T:

mean value in warp and weft directions; (8) According to German Standard Specification DIN EXAMPLE 1 Shirting of 100% cotton in warp and weft yarn (imitation poplin, fineness No. 68/1, warp and wait; 51 ends, 26 picks/cm., weight 122 g./sq. m.) is singed, boiled, mercerized and bleached in the conventional manner. The fabric pretreated in this way is crosslinked dry to produce non-iron and crease resist properties by first impregnating it with the following finishing liquor on a padding machine and squeezing it to about 65% of the dry Weight:

150 g./l. of N methylol-N -methyl-4-methoxy-5,5-di

methylpropylenurea, 50% aqueous solution;

20 g./l. of a 40% aqueous dispersion of a copolymer of 89 parts of n-butyl acrylate, 5 parts of butanediol diacrylate, 3 parts of N-methylolacrylamide and 3 parts of acrylamide;

2 g./l. of a reaction product of isooctylphenol with seven times the molar amount of ethylene oxide and 30 g./l. of magnesium chloride hexahydrate.

The fabric padded with this solution is dried in a tenter at 110 C. to about 4% residual moisture and then cured in a condensation plant for five minutes at 155 C.

Tests give the following data:

F PWF Wash-Wear behavior after one wash at the boil (Monsanto rating (1)) 4.0 2.0 Wet crease recovery angle according to Total Unwashed 133 90 After three Washes at the boil- 137 1 Dry crease recovery angle (3) Unwashed 131 63 After three washes at the boil 108 65 Tensile strength in weft direction, DIN strip method (4) (kg), unwashed 22.4 40.5 Resistance to chorine (scorch test) Loss of strength (percent) 18 Yellowing None Non NorE.-F=finished; PWF=pretreatcd, Without finish.

The same result is achieved by using the same amount of N -methylol-N -propyl 4 methoxy 5,5 dimethylolpropylenurea instead of N -methylol-N -methyl-4-rnethoxy-5,5-dimethylpropylenurea in an otherwise unchanged method.

EXAMPLE 2 (A) A trouser material having warp and weft yarns 36/ l/38/2 of 50/50% polyester staple fiber and cotton, 62 ends, 26 picks/cm., weight 192 g./ sq. m., is given a conventional preptreatment, dyed and given a permanent press finish after having been made up. For this purpose, the material is impregnated with a liquor having the follow composition and squeezed to a Wet pickup of about 75%:

300 g./l. of N -methylol-N -methyl 4 methoxy-5,5-dimethylpropylenurea in 50% aqueous solution;

2 g./l. of the reaction product of isooctylphenol with seven times the molar amount of ethylene oxide;

80 g./l. of a aqueous dispersion of a copolymer of 56 parts of ethyl acrylate, 34 parts of methacrylic acid and 10 parts of acrylic acid;

g./l. of a aqueous emulsion of the o-silicic ester of a long chain alcohol; and

30 g./l. of zinc nitrate hexahydrate.

The material is dried in a tenter at 100 C. to a residual moisture content of about 7%.

(B) For comparison, the same material is finished in the same way with a liquor which contains the same amount of a aqueous solution of N N -dimethylol- 4-methoxy-5,S-dirnethylpropylenurea instead of the monomethylol compound.

Samples of the materials thus treated are kept for thirty days in a closed desiccator at 25 C. in a drying cabinet. In a smelling test, material (A) has a weak and material (B) has a strong odor of formaldehyde.

The two materials are made up into mens trousers and after having been made ready are steamed for shaping in the conventional manner on a hothead press; then for six seconds they are pressed (temperature of the pressure plate 195 C.), sucked off and the shape is fixed in an oven for twelve minutes at 175 C. These heat treatments cause a considerable formaldehyde odor only in the case of trousers finished in accordance with method (B). After Washing in a domestic washing machine (drum type, maximum temperature about 60 C., with rinsing and spin-drying) and drying on a. line, the trousers have a smooth appearance and hold the creases well. The trousers obtained by method (A) have however a much softer handle than those obtained according to method (B).

EXAMPLE 3 (A) The shirting described in Example 1 is pretreated and then (to impart non-iron properties by the moist crosslinking principle) impregnated with the following liquor and squeezed to a wet pickup of 70% on a padding machine:

300 g./l. of N -methylol-N -methyl-4-rnethoxy 5,5 dimcthylpropylenurea as a 50% aqueous solution;

30 g./l. of a 40% aqueous dispersion of a copolymer of 89 parts of n-butyl acrylate, 5 parts of butanediol diacrylate, 3 parts of N-methylolacrylamide and 3 parts of acrylamide;

2 g./l. of the reaction product of isooctylphenol with seven times the molar amount of ethylene oxide; and

20 g./l. of 48% sulfuric acid.

The material padded in this way is dried at C. in a tenter to a residual moisture of about 6% and then .stored for sixteen hours in a rolled-up condition, packed in polyethylene sheeting. It is then neutralized and rinsed in an open width washing machine.

(B) For comparison, the same fabric is finished under the same conditions but with the monomethylol compound replaced by 300 g./l. of a 50% aqueous solution of N ,N -dimethylol-4-methoxy 5,5 dimethylpropylenurea. During application, and particularly during drying, this product develops a much stronger formaldehyde odor.

Testing gives the following data:

EXAMPLE 4 The test fabric from Example 1 is first padded with the following liquor and squeezed to a wet pickup of about 65%:

200 g./l. of N -methylol-N -methyl 4 methoxy 5 ,5 dimethylpropylenurea as a 50% aqueous solution; and

2 g./l. of the reaction product of isooctylphenol with seven times the molar amount of ethylene oxide and then dried at C. to a residual moisture of about 3%. Then a mixture of:

460 ml. of isopropanol (99%);

460 mi. of formic acid (84% and 80 ml. of hydrochloric acid (34%) is applied at the rate of about 30% of the weight of the fabric by means of a padding machine at room temperature.

The fabric treated in this way is rolled up without folds, packed in polyethylene sheeting and left for twenty hours at room temperature while being continuously turned. The finished fabric is then neutralized and rinsed on an open width washing machine.

Testing gives the following results:

NoTE.F=fi.n ished; PWF=pretreated Without finishing.

Replacement of N -methylol-N -methyl-4-methoxy-5,5- propylenurea by the same amount of N -methoxymethyl- N -methyl-4-methoxy 5,5 dimethylpropylenurea or N methylol-N -methyl-4-hydroxy-5-methyl 5 ethylpropylenurea with the other conditions unchanged produces the same result.

EXAMPLE 5 The fabric described in Example 1 is crosslinked by the following method by machine padding (wet pickup about 70%) with the following solution at 18 C.:

300 g./l. of N -methylol N methyl-4-methoxy-5,5-dimethyl-propylenurea as a 50% aqueous solution;

g./l. of aqueous dispersion of a copolymer of 89 parts of n-butyl acrylate, 5 parts of butanediol diacrylate, 3 parts of N-methylolacrylamide and 3 parts of acrylamide;

100 ml./l. of technical concentrated hydrochloric acid;

and

2 g./l. of the reaction product of isooctylphenol with seven times the molar amount of ethylene oxide.

The fabric treated in this way is rolled up without folds, packed in polyethylene sheeting and stored for twenty hours at room temperature while being turned.

The fabric is then neutralized and rinsed on an open width washing machine.

Testing gives the following results:

Wash/wear behavior (2) Monsanto:

After one wash at the boil 3.2 Wet crease recovery angle (Tootal) (8) Unwashed 135 After One wash at the boil 130 Dry crease recovery angle (6) Unwashed 85 After one wash at the boil 76 Tensile strength (kg) (7) (weft):

DIN strip method 32.8 Resistance to chlorine (5) (scorch test) Loss of strength (percent) 7 Yellowing None Similar results are obtained when N methylol N rnethyl-4-methoxy-5,S-dimethylpropylenurea is replaced by the same amount of N -methylol-N -ethyl-4-hydroxy- 5,S-dimethylpropylenurea with the method otherwise unchanged.

EXCHANGE 6 The fabric specified in Example 1 is impregnated on a padding machine with the following finishing liquor and squeezed to 70% wet pickup:

100 g./l. of N -methylol N methyl-4-methoxy-5,5-dimethylpropylenurea as a aqueous solution; 100 g./l. of a 40% aqueous dispersion of N -methoxy- 10 methyl-N -stearyl-4-methoxy 5,5 dimethylpropylenurea;

20 g./1. of a 40% aqueous dispersion of a copolymer of 89 parts of n-butyl acrylate, 5 parts of butanediol diacrylate, 3 parts of N-methylolacrylamide and 3 parts of acrylamide;

2 g./l. of a reaction product of isooctylphenol with seven times the molar amount of ethylene oxide; and

30 g./l. of magnesium chloride hexahydrate.

The fabric padded with this mixture is dried on a tenter at C. to a residual mOisture of about 4% and then cured in a condensation plant during five minutes at C.

Tests give the following data:

F PWF Wash/wear behavior after one wash at the boil (Monsanto) (l) 4 2 Wet crease recovery angle Tootal (2):

UnWashed 134 90 After three washes at the boil 137 104 Dry crease recovery angle (3):

Unwashed. 133 63 After three Washes at the boil 128 65 Tensile strength in weft direction, DIN strip method (kg) (4), unwashed 23 40.5 Resistance to chlorine (scorch test) (5):

Loss of strength (percent) 17 4 Yellowing None None NOTE.F =finished; PWF =pretreated, without finishing.

The fabric which has been finished and washed at the boil has a particularly soft handle.

Replacement of N -methoxymethyl-N -stearyl-4-methoxy-5,5-dimethylpropylenurea by the same amount of N methoxymethyl-N -n-decyl 4 methoxy 5,5 dimethylpropylenurea with the method otherwise unchanged results in the same physical data but a handle which is somewhat less soft.

We claim:

1. In a process for finishing textile material which consists of or contains natural or regenerated cellulose by impregnating said textile material with a solution or dispersion of a finishing agent and an acid catalyst and reacting the impregnated material, if desired after drying and making up into articles of clothing, cellulose molecules being linked to the finishing agent by acetal linkages under the influence of said acid catalyst, the improvement of using as the finishing agent at least one compound of the formula where R and R denote hydrogen atoms or low molecular weight alkyl radicals, R denotes an alkyl radical with 1 to 18 carbon atoms, R denotes a hydrogen atom or a radical of the formula and R and R denote low molecular weight alkyl radicals. 2. In a process as claimed in claim 1 the improvement of using as the finishing agent at least one compound of the formula 1 l 1 2 R and R denote hydrogen atoms or alkyl radicals with References Cited 1 to 3 carbon atoms, R denotes an alkyl radical with 1 to 18 carbon atoms and R and R denote alkyl radicals UNITED STATES PATENTS with 1 to 3 carbon atoms 3,488,701 1/1970 Herbes et al. 8116.3 3. In a process as claimed in claim 1 the improvement 5 3,502,672 3/1970 Petersen et of using as the finishing agent N -methylol-N -methyl-4- methoxy 5,5 dimethy1pr0pylenurea GEORGE F LESMES, Prlmary Examiner 4. In a process as claimed in claim 1 the improvement J. CANNON, Assistant Examiner of using as the finishing agent a mixture of two compounds of the said formula, one of them having an alkyl 10 US. Cl. X.R. radical R with 10 to 18 carbon atoms and the other hav- 1 11 2 ing an alkyl radical R with less than 10 carbon atoms. 1 38 6 251