US2723924A - Treatment of wool-containing textile materials and products thereof - Google Patents

Description

United States Patent *Ofiice 2,723,924 Patented Nov. 15, 1955 TREATMENT OF WOOL-CONTAINING TEXTILE MATERIALS AND PRODUCTS THEREOF Herbert W. Mackinney, Pines Lake, N. 1., assignor to Union Carbide and Carbon Corporation, a corporation of New York No Drawing. Application February 3, 1953, Serial No. 334381 6 Claims. (11. 117-141 This invention relates to the treatment of wool and wool-containing textile materials for shrink-proofing the wool and for rendering the same resistant to felting; and more especially it concerns a novel process whereby wool or wool-containing textile articles are stabilized against undue shrinkage and felting during the service life of textiles made therefrom. The invention includes the wool-containing textile article thus stabilized.

The strong tendency of wool and wool-containing textile articles to shrink and to felt upon washing thereof during their service life has long beenknown. Numerous attempts have been made to overcome in some degree these objectionable characteristics of wool and wool-containing textiles. While some treatments of wool have provided some improvement in such-properties of the wool none have been entirely satisfactory, often because of the sacrifice of some other desired property of the textile, or due to lack of permanence of, the shrinkproofing.

The invention isbased in important part upon the discovery that when wool or a, wool-containing textile is treated with a mildly acidic solution of certain hereindescribed novel resins, the resin is adsorbed on the sur faces of the wool, and upon being converted thereon to the infusible insoluble form, adheres tenaciously to the wool and confers thereon the property of resisting felting and shrinking during laundering. The invention has the further advantages that .it is applicable to wool in any form, such as fibers, yarns, or woven or knitted textiles, as well as to mixtures of wool with other textile materials such as cotton, nylonQdynel, fOrlon, etc. No squeeze roll treatment or the equivalent is necessary to remove excess of the resin composition and hence the hand of the wool is not deleteriously affected and interfiber bonding does not occur. The complete treatment is conducted at moderate temperatures in very dilute aqueous solutions, hence the wool is not exposed to high temperatures. during this anti-felting treatment. The process readily can be conducted in simple apparatus such as that used for dyeing. The resin treatment preferably is applied to the wool or wool-containing textile after dyeing and fulling.

In the practice of the invention the wool or woolcontaining textile article is wetted with water containing suflicient of a hydrogen halide or a lower fatty acid having one to five carbon atoms to adjust the bath to a pH within the range from 3 to 6. The wetted wool is then heated within therange C. to 100 C. and preferably around 50 C. to 70 C. in a mildly acidic aqueous solution containing a salt of a novel polyamino polyhydroxy resin until the adsorption of the resin is complete. This solution essentially comprises enough water acidified with a hydrogen halide or a lower fatty acid ofone to five carbon atoms to provide a pH between 3 and 6 to cover the article being treated, together with a suitable quantity of an acid soluble resin of the type hereinafter described. Preferably the solution also contains suflicient of an in- Relaxation shrinkage can be eliminated solubilizing agent such as formaldehyde, glyoxal or a water soluble aliphatic diepoxy compound such as diglycidyl ether and ethylene glycol diglycidyl ether to promote adherence of the resin upon the article. A small amount of non-ionic wetting agent preferably also is present. The quantity of resin used increases with the fineness of the wool fibers being treated, and with the extent of surface damage in the case of reprocessed wool. An amount of resin between 3% and 12% of the dry Weight of the wool or wool-containing article generally is sufiicient. When used, the amount of insolubilizing agent can vary considerably. Excellent results are secured when it is about one-third of the weight of the resin used. After the resin solution has been suitably adsorbed by the fibers, which commonly is effected in one to two hours, the treated article is removed from the solution and excess treating liquid is drained off. When an excess of the resin over that adsorbed by the fibers is present, the heated article is then thoroughly rinsed with water to remove excess treating agent.

The final conversion of the resin to the insoluble, infusible form after its adsorption by the wool fiber preferably is effected at ambient temperatures, using a cold dilute alkaline aqueous solution containing sulficient of an alkaline compound, such as an hydroxide, carbonate or bicarbonate of an alkali metal, a tertiary amine and the like, to adjust the pH of the solution to at least 8.

The solution also contains an insolubilizing agent of the class consisting of formaldehyde, glyoxal and the water soluble diglycidyl compounds recited hereinbefore. This conversion solution contains from about 1% to' about 5% of each of the said alkaline compound and the insolubilizheating the resin-treated article to temperatures of 200 F. to 300 F. or somewhat higher in the presence of a' small amount; e. g. 1%, of one of the. insolubilizing agents. I

The treated article then is rinsed with'water and dried, preferably untensioned. i

If desired, the solution of resin and insolubilizing agent can be applied to the wool containing article by the well known padding technique, in which case the padding is done at or about room temperature, and the padding solution preferably contains a non-ionic wetting agent. The paddedarticle is dried at temperatures commonly around 220 F. to 3-00 F. to convert the resin to the insoluble form, after which the article is scoured with. a detergent and dried in the untensioued state. In this procedure the solution remaining in the cloth deposits some resin on the fiber in massive form which then bonds one fiber to another and causes stiffening. This padding method is therefore used only when such stiffening is desirable. 1

The novel resinsemployed in this invention are the chemically reactive resinous products soluble in acidic aqueous solution which are prepared by reacting aryl polyepoxides at elevated temperatures with the salts resulting from the neutralization of aliphatic polyamines with fatty acids having from 2 to 5 carbon atoms, preferably acetic acid. The said reaction is conducted in a volatile solvent such as a lower alkanol, preferably near its boiling point. tions are secured by reacting with the alkylene polyamine salt of a monocarboxylic acid of the kind described an amount of an aryl diepoxide sufiicient to substitute not If desired, the re- Useful resins soluble in dilute acid solumore than one epoxy group for each of the primary and secondary amino hydrogen atoms of the polyamine.

Aryl polyepoxy compounds useful in the production of the dilute-acid soluble resins include compounds of the formula x X x 2 [1g Z1 1g 2 I Lt H3 1t wherein R and R respectively represent hydrogen or an alkyl or phenyl radical; X represents hydrogen or a halogen; Z represents a group; and n is or an integer of 1 to 2. Other aryl diepoxy compounds useful are those of the formula:

wherein Z has the aforesaid meaning. Examples of such aryl polyepoxy compounds are the diglycidyl ethers of the various dihydroxydiphenylmethylphenylmethanes, and corresponding ethers of the dihydroxydiphenyldimethylmethanes, dihydroxydiphenylmethylethylmethanes, dihydroxydiphenylmethylpropylmethanes, dihydroxydiphenyl methanes, dihydroxydiphenylbutylphenylmethanes, dihydroxydi(chlorophenyl)methanes and dihydroxydi-(chlorophenyl)-dimethylmethanes; and the diglycidyl ethers of the O-, mand p-dioxybenzenes, such as hydroquinone diepoxypropyl ether. Commercial grades or mixtures of the foregoing can be used.

' The alkylene polyamine salts useful in the production of the dilute acid-soluble resins effective for shrink-proofing wool include the salts formed by reacting, while cooling to prevent vaporization of the solvent, a solution of 1,2-diaminopropane, l,3-diaminopropane, or a member of the homologous series H2N(CH2CH2NH)11H wherein n is an integer from 1 to about 50, in a volatile solvent such as a lower alkanol, with a saturated monocarboxylic aliphatic acid having from 2 to 5 carbon atoms, such as acetic, propionic, butyric or isovaleric acid, in a molar ratio such that all amino groups of the polyamine are converted to amino salts. Complete neutralization of the amino groups is required in order to secure acid-soluble resins by reacting stoichiometric proportions of the amino and epoxy groups.

The following examples serve to illustrate the invention:

Example 1 A resin soluble in dilute acids was made by reacting 180 grams of di(1,2-epoxypropoxyphenyl)-dirnethylmethane, with 74 grams of diethylene triamine triacetate in 300 grams of boiling ethanol for 24 hours. The solution was concentrated by evaporation of the solvent under vacuum, the concentrate containing about 58% of the resin, 38% of ethanol and 4% of water.

A wool-treating solution was made by mixing 170 grams of the said concentrated resin solution, 770 grams of water, grams of a non-ionic wetting agent being marketed under the trade name of Triton NE and 50 grams of a 37% aqueous formaldehyde solution. This treating solution was used to pad a quantity of wool flannel to a retention thereon of 75% of its weight of the said solution. The flannel then was dried at 220 F., heated 3 minutes at 300 F. to cure the resin, scoured with an aqueous solution of a detergent, and dried untensioned. The weight of the flannel was increased 6% by this treatment.

The treated flannel and a piece of the untreated flannel previously soaked in water and dried, untensioned, was washed five cycles in a vertical shaft type washing machine having a basket 13 inches in diameter oscillating 60 cycles per minute. Each cycle consisted of a 15 minutes washing ess essentially comprises the following steps.

in a 0.5% aqueous solution of neutral soap at 120 F., and two subsequent washings with 120 F. water during 15 minutes with the machine running.

Following five of such laundering cycles the treated flannel shrunk only 1.5% in the warp direction and 1.2% in the filling direction, with no evidence of felting. The untreated flannel similarly laundered had felting shrinkage of 22% in the warp direction and 13% in the filling direction, and showed very severe felting.

Example 2 Following the procedure and using the materials described in Example 1, with the exception that 40 grams of di-(2,3-epoxypropyl) ether was substituted for the formaldehyde, wool flannel was padded with an aqueous solution containing 6% of the acid-soluble resin and 4% of the di-(2,3-epoxypropyl) ether.

The wool retained of its weight of the solution. The wool then was dried and the resin insolubilizedby heating at 220 F. during 15 minutes. The thus treated wool and a piece of the untreated wool were subjected to three laundering cycles as described in Example 1. The laundered treated wool had shrunk 1.7% in the warp direction and 0.1% in the filling direction, whereas the shrinkage of the untreated wool was 14.6% (warp) and 9.5% (filling) in the laundering.

The acid-soluble polyamino polyhydroxy resins of the invention possess the unexpected and unique property and important advantage that the resins can be exhausted from dilute aqueous solutions thereof upon wool immersed in such solutions. The amount deposited can thus be closely controlled and objectionable excesses avoided. It has been found that if wool or a Wool-containing textile article is warmed while immersed in a mildly acidic solution of these resins, the resin is adsorbed on the wool surface and, when insolubilized thereon, either by heating or by treatment with an aqueous solution containing a small amount, e. g., about 1% to 5%, based upon the Weight of the dry article, of an alkaline compound of the type hereinbeforedescribed, and of a small amount, e. g. 1% to 5% of formaldehyde, glyoxal or a Water-soluble diglycidyl ether, based upon the dry weight of the article, the resin is converted in situ to the insoluble state and confers upon the wool or article the property of resisting felting in laundering. This method has the important advantages over prior methods that it is applicable to wool in any desired form, e. g., fibers, yarns, woven and knitted articles, etc. The hand of the wool is not affected since inter-fiber bonding, the major cause of the stiffening which occurs in squeeze roll treatments, is absent. The entire deposition upon the wool surface occurs from very dilute aqueous solutions of the resin at moderate temperatures. The wool is not subjected to high temperatures, and relaxation shrinkage can be eliminated by controlling tension during drying.

Conveniently this immersion method of treatment of the wool or wool-containing article is conducted in simple apparatus of the type used in dyeing the article, and preferably is applied thereto after fulling and dyeing, and while the article is wet.

in this preferred modification of the invention the proc- The textile article'is wetted with water using a wetting agent of the nonionic type, with the Wetting liquid adjusted to a pH:

within the range between 3 and 6. The wetted article then is immersed in a mildly acidic aqueous solution of the acid soluble polyarnino, polyhydroxy resin until adsorption by the article is complete. Preferably this solution comprises water containing sufficient acid to give it a pH of 4 to 6, from about 2% to 12% of the said polyamino polyhydroxy resin and from about 1% to about 5% of an insolubilizing agent which may be formaldehyde, glyoxal, or a simple water soluble diepoxy compound such as diglycidyl ether, the percentages being based upon the dry weight of the article. The acids used in the solution are such as form water soluble salts with the resins, suitable acids being the hydrogen halides and the saturated fatty acids having up to carbon atoms. The resin gradually is adsorbed by the article up to a maximum required to coat the fiber surfaces of the article after which no more resin is taken up. Any excess resin is removed by immersing in water before proceeding to the final step.

In a final step the thus treated wool or wool-containing article is treated, preferably at ambient temperatures, with a dilute aqueous solution containing sufficient of an alkaline compound of the type hereinbefore described to give the solution a pH of at least '8. The solution also contains a small amount of an insolubilizing agent such as formaldehyde, glyoxal, or a water-soluble diepoxy compound such as di'glycidyl ether. The alkaline compound and the insolubilizing agent, respectively, are present in an amount of around 1% to 5%, based upon the dry weight of the article. This step of the treatment generally requires about 5 to 15 minutes.

The article then is rinsed with water until free from alkaline compounds and excess insolubilizer, and is dried untensioned. After the final rinsing the article is resistant to felting without further treatment. The usual finishing steps of softening, steaming, napping, decating, and the like can follow, as desired.

,If desired, the wool article containing the absorbed and partially insolubilized resin can be heated as a final step to cure the resin and impart felt-resistant properties to the article, in the manner described in Example 1.

The following examples illustrate this modification of the invention:

Example 3 A polyphenylolmethane mixture was made by reacting 590 grams (6 mols) of phenol at 30'35 C. with 81 grams of 37% formalin (1 mol of HCHO) in the=presence of sufiicient concentrated hydrochloric acid to reduce the pH of the mixture below zero until all of the formaldehyde had reacted. Excess phenol was distilled off under 50 mm. of mercury pressure at below 165 C. The residue of about 180 grams consisted of approximately two-thirds by Weight of a mixture of isomeric diphenylolmethanes and about one-third of higher molecular analogous structures containing three and four phenyl rings. The aforesaid distillation residue of mixed polyphenylolmethanes (about 180 grams) was reacted with 550 grams (6 mols) of epichlorohydrin and 180 grams of a 50% aqueous solution of caustic soda at 5060 C. during about 2 hours. Excess epichlorohydrin then was distilled off under vacuum at temperatures below 60 C., the mixed polyepoxypropyl ethers of polyphenylolmethanes separated as a viscous liquid having an equivalent weight of 171 grams per epoxy group. This product comprised about two-thirds by weight of diepoxypropyl ethers of mixed diphenylohnethanes (mostly 2,4fand 4,4'--isomers) and about one-third of the triepoxypropyl and polyepoxypropyl ethers ofmixed polyphenylolmethanes containing three or more benzene nuclei, all phenolic hydroxyl groups being reacted to form epoxypropyl groups.

A water-soluble polyamino polyepoxy resin was produced by adding 760 grams (4.4 equivalents) of the aforesaid mixed polyepoxypropyl ether of diphenylolmethane, diluted with 76 grams of methanol, during 2 to 3 hours to a boiling solution of 283 grams (1 mol) of diethylene triamine triacetate in 700 parts of methanol. The boiling was then continued until, upon testing, the resin formed a clear solution with ten times its volume of water. It was cooled and 120 grams of glacial acetic acid were added thereto to stabilize the resin solution and increase its useful storage life. The solution now contained about 50% of the resin. The addition to the resin of a quantity of an aliphatic saturated monocarboxylic acid having 2 to 5 carbon atoms, in excess of that required to form salts with all of the amino groups present, is effective as stabilizer for the resin. Commercially adequate storage life is obtained by the addition of one or two mols of such organic acid 'per mol of the polyamine used in making the acid-soluble resin.

All-wool socks grams), were wetted with a dilute aqueous solution of acetic acid having a pH of approximately 5. The wetted socks then were immersed in an aqueous solution at pH 5, containing 5000 grams of Water, 5 grams of the said polyepoxy resin, 0.6 gram of acetic acid, 2 grams of formaldehyde (as HCHO) and 4.6 grams of methanol. The solution and socks were maintained at 70 C. until no further resin was adsorbed by the socks. This was determined by taking aliquot samples of the solution at intervals, precipitating the resin therein with caustic alkali, and determining gravimetrically the resin present in the sample. The socks were rinsed with water, then immersed for 5 minutes in cold water containing 1 gram of sodium carbonate and 1 gram of formaldehyde, and finally rinsed and dried untensioned.

The treatment rendered the wool less sensitive to alkalies, as shown by a reduction in the percentage of matter soluble in alkalies from 11.4% on untreated socks to 8.0% on the treated socks, according to the test described in Federal Catalog CCC-T-l91a, Supplement, 1945, section VII, paragraph 3 (Supt. of Documents).

The thus treated socks, and a quantity of the untreated socks, soaked in water and dried untensioned, were washed ten cycles using the procedure described in Example 1.

The treated socks had a shrinkage of 2.5% measured on the foot length, with no evidence of felting. 1 The untreated socks after similar washing and drying untensioned showed 15% shrinkage and very serious felting. The hand of the sockswas not noticeably affected by the treatment.

Example 4 All wool shirting cloth about 10 ounces per yard unit weight (900 grams) was wet out with an aqueous solution containing a non-ionic wetting agent marketed as Triton NE and adjusted to pH 5. The cloth was then heated to the boil in one hour in 8,000 grams of an aqueous solution containing 13 grams of the polyamino polyhydroxy resin solution described in Example 3, two grams formaldehyde and 8 grams Triton NE. After complete adsorption of the resin by the cloth in 80 minutes the cloth was rinsed thoroughly and treated .for 10 minutes with a cold aqueous alkaline solution containing 10 grams sodium carbonate and 10 grams formal dehyde. The cloth then was rinsed with water and dried at F. untensioned. The finished cloth had a soft pliable hand similar to that of the untreated cloth. It had shrinkages of 3.4% and 1.7%, respectivelyv in the warp and the filling directions after a laundering test according to Federal Specification CCC-T-1'91b Textile Test Methods, Method 5554, Supt. of Documents, May 15, 1951.

The cloth increased 4% in weight as the result of the resin treatment.

Example 5 Ten grams of polyethyleneamine of the formula H(NHC2H4)nNH2 having an average molecular weight of 1800 was dissolved in 60 grams of methanol and was carefully neutralized (to bromophenol blue) with 30 grams of butyric acid. This solution then was boiled with 60 grams of 1,1-bis-(1,2-epoxy-3-propoxyphenyl) butane (mixed paraand ortho-isomers) having an equivalent weight of 230 grams per epoxy group until the solution was miscible with ten times its weight of water. After the further addition of 15 grams of butyric acid to serve as a stabilizer, the solution contained 44% of the resultant resin.

Wool flannel (70 grams) previously wet with water and adjusted to pH 5.2 with dilute butyric acid was heated to boiling 2 hours in an aqueous solution containing 9.8 grams of the aforesaid resin solution, 1 gram of formaldehyde and about 1990 grams of water, and adjusted to pH 5. The wool then was rinsed with water, and was immersed in water containing 1% of sodium carbonate and 1% formaldehyde, based on the dry weight of the flannel, and then was rinsed and dried untensioned.

Following a severe laundering for 1 hour at 140 F. using the apparatus and method described in Example 1, the treated flannel had shrunk 2%, whereas the untreated flannel had shrunk 15 as a result of the same laundering.

Example 6 Para-bis 1,2-epoxy-3 -propoxy-ortho-chlorophenyl methane (99 grams) was boiled with 70 grams of diethylene triamine triacetate in 100 grams of methanol until miscible with 10 times its weight of water. Then 30 grams of glacial acetic acid were added as a stabilizer. A mixture of 8.3 grams of this polyamino polyepoxy resin solution and 3 grams of a 37% formaldehyde solution was diluted to 2000 grams with water.

Wool flannel (100 parts), wetted and adjusted to pH 5 with acetic acid, was immersed in this solution and heated 2 hours at 70 C., the resin being substantially completely adsorbed. The cloth was rinsed and then treated with a cold aqueous alkaline formaldehyde solution containing 1% of sodium carbonate and 1% formaldehyde, based upon the weight of the dry flannel.

After drying the treated flannel untensioned, and laun dering the same for 2 hours at 140 C. in the general manner described in Exampe 1, the flannel shrank 3%, whereas the untreated flannel shrank 15% after the same laundering.

Example 7 A length of a 16 ounce shirting approximately 4.75 yards long, of mixed fiber content 90% wool and nylon, weighing 5.1 pounds, was rinsed with 300 pounds of water containing 0.4 ounce of a non-ionic Wetting agent of the substituted polyethylene glycol type. The cloth then was heated at 70 C. for 6 hours in 300 pounds of an aqueous solution containing 10.6 ounces of the 50% resin solution described in Example 3, 3.3 ounces of a 37% aqueous formaldehyde solution and 0.4 ounce of the said non-ionic wetting agent, corresponding to 6.8% of the resin and 1.9% of formaldehyde, based upon the weight of the cloth. After cooling and rinsing off any excess resin solution the cloth was treated with a cold aqueous solution containing 0.65 ounce of sodium carbonate and 1.6 ounces of 3% formalin, rinsed, and then treated with a cold aqueous solution containing 0.1 ounce sodium stearate, again rinsed, the pH adjusted to 6, and the treated shirting dried.

In a laundering cycle described in Federal Specification CCC-T-l9lb, Supt. of Documents, May 15, 1951, as method'5554, after relaxation as per method 5558, applied to samples of the treated and untreated shirting, the following results were secured:

Felting Shrinkage, Percent Warp Filling Untreated cloth 12. 1 8. 2 Treated cloth 3. 0 '0. 3

Example 8 Shrinkage, Percent Warp Untreated flannel Treated flannel Filling The invention is susceptible of modification within the scope of the appended claims.

I claim:

1. Process for improving the properties of wool-containing textile materials and rendering the same resistant to felting and shrinkage in laundering, which comprises heating said material in a dilute aqueous solution having a pH within the range from 3 to 6 and containing (A) a water-soluble resinous product of the reaction of (1) a neutral salt of an alkylene polyamine with a saturated aliphatic monocarboxylic acid having from 2 to 5 carbon atoms and (2) an aryl polyepoxy compound of the class consisting of those having the formula X is selected from the class consisting of hydrogen and the halogens; Z designates a group; and n is zero or an integer of 1 to 2; and curing the resin in situ on the textile material, and at some stage prior to the completion of the curing step, treating the textile material containing said resinous product with an insolubilizing agent selected from the class consisting of formaldehyde, glyoxal and the water-soluble aliphatic digiycidyl ethers.

2. Process for improving the properties of wool-containing textile materials and rendering the same resistant to felting and shrinkage in laundering, which comprises heating said material in a dilute aqueous solution having a pH within the range from 3 to 6 and containing (A) a water-soluble resinous product of the reaction of (1) a neutral salt of an alkylene polyamine with a saturated aliphatic monocarboxylic acid having from 2 to 5 carbon atoms and (2) an aryl polyepoxy compound of the class consisting of those having the formula cals; X is selected from the class consisting of hydrogen and the halogens; Z designates a group; and n is zero or an integer of 1 to 2; and (B) an insolubilizing agent selected from the class consisting of formaldehyde, glyoxal and the water-soluble aliphatic diglycidyl ethers, and thereafter curing the resin in situ on the textile material.

3. Process for improving the properties of wool-containing textile materials and rendering the same resistant to felting and shrinkage in laundering, which comprises heating said material in a dilute aqueous solution having a pH within the range from 3 to 6 and containing (A) a water-soluble resinous product of the reaction of (1) a neutral salt of an aliphatic alkylene polyamine with a saturated aliphatic monocarboxylic acid having 2 to 5 carbon atoms, and (2) an aryl polyepoxy compound having a structure corresponding to the formula X is selected from the class consisting of hydrogen and the halogens; Z designates a radical; and n is zero or an integer of 1 to 2; said aqueous solution also containing an insolubilizing agent for (A) selected from the class consisting of formaldehyde, glyoxal and the water-soluble aliphatic diglycidyl ethers; and thereafter treating the thus impregnated textile material with a dilute aqueous solution containing an alkaline watersoluble compound in amount at least sufiicient to give the solution a pH of at least 8.

4. Process for improving the properties of wool-containing textile materials and rendering the same resistant to felting and shrinkage in laundering, which comprises heating said material in a dilute aqueous solution having a pH within the range from 3 to 6 and containing (A) a water-soluble resinous product of the reaction of (l) a neutral salt of an alkylene polyamine with a saturated aliphatic monocarboxylic acid having from 2 to carbon atoms and (2) an aryl polyepoxy compound of the class consisting of those having the formula the halogens; Z designates a CH2CHCH20 group; and n is zero or an integer of 1 to 2; and (B) an insolubilizing agent selected from the class consisting of formaldehyde, glyoxal and the water-soluble aliphatic diglycidyl ethers, and thereafter treating the thus impregnated textile material with a dilute aqueous solution containing at least around 1% of an alkaline alkali metal 10 compound and at least around 1% of formaldehyde, both based upon the dry weight of the material.

5. Process for improving the properties of wool-containingtextile materials and rendering the same resistant to felting and shrinkage in laundering, which comprises heating said material in a dilute aqueous solution having a pH Within the range from 3 to 6 and containing (A) a water-soluble resinous product of the reaction of (1) a neutral salt of an aliphatic alkylene polyamine with a saturated aliphatic monocarboxylic acid having 2 to 5 carbon atoms, and (2) a polyglycidyl polyether of a dihydric phenol having a 1,2-epoxy equivalency greater than 1.0; said aqueous solution also containing an insolubilizing agent for (A) selected from the class consisting of formaldehyde, glyoxal and the water-soluble aliphatic diglycidyl ethers; and thereafter treating the thus impregnated textile material with a dilute aqueous solution containing at least around 1% of an alkaline water-soluble compound and at least around 1% of formaldehyde, both based upon the dry weight of the textile material.

6. Wool-containing textile material resistant to felting and shrinkage in laundering, the fibers forming said material having on their surfaces a water-insoluble composition comprising the insolubilized water-soluble resinous product of the reaction of (1) a neutral salt of an alkylene polyamine with a saturated aliphatic monocarboxylic acid having 2 to 5 carbon atoms, and (2) an aryl polyepoxy compound of the formula radicals; X is selected from the class consisting of hydrogen and the halogens; Z designates a OHzCHCHzO- group; and n is zero or an integer of not more than 2.

References Cited in the file of this patent UNITED STATES PATENTS 2,537,064 Kropa et al. Jan. 9, 1951 2,539,958 Maaskant Ian. 30, 1951 2,632,717 Landolt Mar. 24, 1953

Claims (1)

1. PROCESS FOR IMPROVING THE PROPERTIES OF WOOL-CON TAINING TEXTILE MATERIALS AND RENDERING THE SAME RESISTANT TO FELTING AND SHRINKAGE IN LAUNDERING, WHICH COMPRISES HEATING SAID MATERIAL IN A DILUTE AQUEOUS SOLUTION HAVING A PH WITHIN THE RANGE FROM 3 TO 6 AND CONTAINING (A) A WATER-SOLUBLE RESINOUS PRODUCT OF THE REACTION OF (1) A NEUTRAL SALT OF AN ALKYLENE POLYAMINE WITH A SATURATED ALIPHATIC MONOCARBOXYLIC ACID HAVING FROM 2 TO 5 CARBON ATOMS AND (2) AN ARYL POLYEPOXY COMPOUND OF THE CLASS CONSISTING OF THOSE HAVING THE FORMULA