US3026216A

US3026216A - Treatment of textile fabrics with methylglycidyl ethers

Info

Publication number: US3026216A
Application number: US844171A
Authority: US
Inventors: Arnold M Sookne; Howard R Guest; Joe T Adams
Original assignee: Union Carbide Corp
Current assignee: Union Carbide Corp
Priority date: 1959-10-05
Filing date: 1959-10-05
Publication date: 1962-03-20
Anticipated expiration: 1979-03-20

Description

United States Patent race 3,025,215 Patented Mar. 20, 1962 3,926,216 TREATP/ENI F TEXTILE FABRICS WiTH METHYLGLYKITDYL ETHERS Arnold M. Scoltne, Silver Spring, Md., and Howard R. Guest, Charieston, and Joe T. Adams, St. Albans, W. Va, assignors to Union Carbide Corporation, a corporation of New York No Drawing. Fiied Oct. 5, 1959, Ser. No. 844,171 12 Claims. (Cl. 1171? 9.4)

This invention relates, in general, to a process for the treatment of cellulosic textile materials. In one aspect, this invention relates to the treatment of cellulosic and cellulosic-containing textile fabrics with methyiglycidyl ethers.

This application is a continuation-in-part of application Serial No. 833,688, filed August 14, 1959, by H. R. Guest, J. T. Adams and A. M. Sookne, entitled Stabilized Textile Treating Solutions and Process for Their Use, and assigned to the same assignee as the instant invention.

With the increased use of synthetic fibers, textile materials have been produced which can be washed, dried and worn with little or no ironing. These wash-andwear properties of the synthetic fibers have stimulated a corresponding technological advancement in the field of the cellulosic fibers so that today, crease and shrink resistant properties can be imparted to cotton, rayon and linen fabrics by the use of appropriate chemical finishes. The most commonly used finishes are the formaldehyde reaction products of nitrogen-containing chemicals such as ureaformaldehyde, melamine-formaldehyde, dimethylol ethylene urea and the like. While the treatment of cellulosic fabrics with the aforementioned finishes imparts to the fabric the desired shape-holding properties, the use of nitrogen-containing finishes is subject to several disadvantages. For example, the effectiveness of these treatments diminishes after repeated commercial launderings and such finishes tend to retain chlorine from bleaching solutions which results both in a yellowing of the fabric and a measurable loss of strength after ironing.

The more recent developments of new finishes have been directed to the polyepoxides which can be applied to the textile fabric in the form of an aqueous emulsion or dissolved in a solvent miscible with water and then cured within the fibers by means of an epoxy curing agent. Since the polyepoxides usually contain no nitrogen, they are of particular interest for they do not exhibit the chlorine retentive characteristics of the earlier chemical finishes. Several polyepoxides, particularly the polymers of the glycidyl ethers of aliphatic alcohols or polyols have been utilized either alone or in combination with polyaldehydes, polymethylol-substituted phenolic compounds and other components to give crease and shrink resistant properties to textile materials. The polyepoxides, while an improvement in many respects over the nitrogen-containing finishes are still subject to certain deficiencies. The use of a softener is required in many cases to overcome the harsh feel of the fabric imparted by the polyepoxide finish while the yellowing of the softener itself during curing may necessitate the use of a bleach. While a few of the polyepoxides are slightly soluble in water, their solubility is such that it is not advantageous to prepare treating baths of such low concentrations since it would necessitate repeated padding to obtain the desired add-on of polyepoxide. For this reason, the polyepoxide usually requires an emulsifying agent or non-aqueous solvent to prepare a bath of suitable concentration. This is particularly true when the polymers or copolymers of the epoxy-containing monomers, or monomers of high molecular weight are used. Additionally, when used in combination with other components, the solubility can be even less. In many instances, the presence of an emulsifying agent makes the curing of the polyepoxide more difificult to catalyze and even yellows the fabric to a greater degree than do the nitrogen-containing finishes. The use of non-aqueous solvents to circumvent the low Water solubility of the polyepoxide finishes also creates plant operating problems which detract from their other advantages.

A further disadvantage which has also been observed is that many of the polyepoxides tend to undergo hydrolysis with water with the net result that the amount of the polyepoxide in the treating solution available for cross-linking decreases as the hydrolysis reaction proceeds. Due to the acidic nature of many of the catalytic agents employed, this occurrence is greatly aggravated where the epoxy-curing agent is present in the treating solution. It has been observed that textile treating solutions containing polyepoxides and having hydrogen ion concentrations within the range of a pH value of from about 5.5 to 7.5 are fairly stable with relatively little hydrolysis, while, on the other hand, at a pH of approximately 3, or lower, the polyepoxide undergoes rather rapid hydrolysis with the net result that there are fewer epoxy grounds available for reaction with the cellulosic fabirc.

Accordingly, one or more of the following objects will be achieved by the practice of the instant invention. It is an object of the present invention to provide a process for the treatment of cellulosic and cellulosic-containing textile materials wherein the disadvantages previously indicated are substantially eliminated. It is also an object of the present invention to provide a process for impregnating cellulosic textile materials with monomeric polyepoxide compounds whereby the materials are rendered both shrink and crease resistant, while imparting to the material after laundering, a soft, smooth finish without ironing. It is a further object to provide a process for treating textile fabrics which will not exhibit un desirable chlorine retention properties and which are durable to laundering. Another object of the present invention is to provide a process for treating textile materials which does not require the used of emulsifying agents or non-aqueous solvents. A further object is to provide textile treating solutions containing polyepoxides which when applied to a textile fabric can be cured quickly and at temperatures lower than heretofore possible. A still further object of the present invention is to provide textile treating solutions containing polyepoxides which are stable for extended periods of time. These and other objects will readily become apparent to those skilled in the art in the light of the teachings herein set forth.

A broad aspect of this invention is directed to a process for treating cellulosic and cellulosic-containing textile materials with a textile treating solution containing one or more polyepoxides whereby a soft smooth finish is imparted to the fabric after laundering without the need for ironing. Specifically, this aspect of the present invention is directed to a process for treating cellulosic and cellulosic-containing textile materials whereby the material is rendered both shrink and crease resistant while imparting to the material after laundering a soft, smooth finish without ironing which comprises impregnating the textile material with a textile treating solution comprising a monomeric polyepoxide having at least one CH2CCHr-O group, an epoxy curing catalyst and then heating the textile material to cure the polyepoxide.

The polyepoxide compounds employed in the practice of this invention are preferably aliphatic and free of el e 3. merits other than carbon, hydrogen and oxygen. Preferred compounds are the bis(2,3-epoxy-2-methylpropyl) ethers of glycols. Particularly preferred compounds are those containing from 8 to 14 carbons atoms. Examples of the polyepoxides include, among others, the methylglycidyl ethers such as bis(2,3-epoxy-2-m'ethylpropyl)- ether, ethylene glycol bis(2,3-epoxy-2-methylpropyl) ether, diethylene glycol bis(2,3-epoxy-2-methylpropyl)ether, propylene glycol bis(2,3-epoXy-2-methylpropyl)ether, trimethylene glycol bis(2,3-epoxy-2-methylpropyl)ether, 1,4- butanediol bis(2,3-epoxy-2-methylpropyl)ether, 1,3-butanediol bis(2,3-epoxy-2-rnethylpropyl)ether, 2,3-butanediol bis(2,3-epoxy-2-methylpropyl)ether, 1,5-pentanediol bis(2,3-epoxy-2-methylpropyl)ether, 1,6-hexanediol bis- 2,3-epoxy-2-methylpropyl) ether, and the like.

The preparation of ethylene glycol bis( 2,3-epoXy-2- methylpropyl)ether and diethylene glycol bis(2,3-epoxy-2- methylpropyl)ether is disclosed in a copending application entitled Methylglycidyl Ethers, filed the same day as the present invention by B. Phillips and F. C. Frostick, Jr. 7

Although other methylglycidyl ethers are equally adaptable for use in the process of this invention, it should be noted that the above compounds are monomeric polyepoxides in contrast to the water-insoluble polymeric-type polyepoxides heretofore known. The polymeric polyepoxides possess many of the disadvantages previously indicated, particularly the necessity for using volatile solvents or aqueous emulsions to prepare the treating bath. The methyl-substituted glycidyl ethers are preferred over the unsubstituted glycidyl ethers in that they can be cured quickly and at temperatures lower than heretofore possible. The polyepoxide compounds employed herein can be cured on the fabric at a temperature of 120 C. in contrast to temperatures of from 130 C. to 190 C. recommended for the unsubstituted glycidyl polyethers. A low curing temperature is a decided advantage in cornmercial cotton finishing since it results in less damaging effect on the color and the fabric itself. At the higher temperatures fabrics treated with polyepoxides have been known to sufier degradation and strength loss from the action of the epoxy curing catalyst. Fabrics treated with methylglycidyl ethers by the process of this invention therefore show a lower strength loss at a particular level of crease recovery than do other commercial polyepoxides.

The term cellulosic and cellulosic-containing textile materials as used throughout the specification and claims is intended to include cellulose or cellulose-containing fibers, whether in the finished state or at some intermediate stage in processing; cellulose and cellulose-containing fabrics whether wovenor knitted; and garments or other articles made from such fabrics. Thus, materials containing cellulose, regenerated cellulose, and mixtures of the two are intended to be within the scope of the present invention.

By applying the polyepoXides of this invention in the form of a stable aqueous solution, the disadvantages inherent in the past have been overcome to give a fabric which is soft, white and has a high degree of crease recovery, shrink resistance and Wash-and -wear characteristics. The cellulosic textile fabrics treated by the process of this invention retain these properties well after repeated laundering and are not'subjected to chlorine retention. Both whiteness and the original strength of the fabric are retained to a surprisingly high degree. Treatment by the method of this invention represents an improvement over other highly durable, non-chlorine retentive finishes heretofore available.

While the polyepoxide finishes generally in use are not easily dispersed in a treating bath to give a homogeneous solution because of the presence of water insoluble polymers, the methylglycidyl ethers employed in the process of this invention have a distinct advantage of having a high solubility in water so that solvents or emulsifying agents are not necessary in preparing the treating bath.

- 4 For example, both ethylene glycol bis(2,3-epoxy-2-methyl- 'pro'pyDether and diethylene glycol bis(2,3-epoxy-2- methylpropyDether have a solubility in water of greater than 29 percent at 25 C.

Another aspect of the present invention is directed to stabilized textile treating solutions containing one or more of the aforesaid polyepoxides. It has been observed that the polyepoxides tend to undergo hydrolysis with water with the net result that the amount of polyepoxide in the treating solution decreases as the hydrolysis reaction proceeds. Due to the acidic nature of many of the catalytic agents employed, this occurrence is greatly aggravated where the epoxy curing agent is present in the treating solution.

In practice, it has been found that a textile treating solution containing from about 1.0 to about 20 percent by weight of polyepoxide and higher, and from about 0.01 to about 10 percent by weight of solution of an epoxy curing catalyst may be conveniently stabilized against hydrolysis by the addition of a stabilizing amount of one or more of the compounds hereinafter mentioned. Although the need for stabilizing the textile treating solutions will largely be determined by the ingredients present and the particular plant operating procedures, it has been found desirable to stabilize solutions wherein the hydrolysis of the polyepoxide exceeds 10 percent in 8 hours at 30 C.

The buffering agents or stabilizers of the present invention. can be any compound which will maintain the hydrogen ion concentration of the textile treating solution at a pH value within the range of from about 5.5 to about 7.5 and thereby stabilize the polyepoxide from hydrolysis. Certain precautions must be taken in the choice of bufiering agents in that they should be substantially unreactive with the epoxy curing catalyst, the polyepoxide, or other components present in the solution. In practice it has been found that good wash-and-wear properties are imparted to textile materials when they are impregnated with textile treating solutions which contain one or more bufiering agents which are members selected from the class consisting of ammonium hydroxide and the oxides, hydroxides, and salts of the metals designated as group II of the periodic classification of the elements, F. Daniels,

' Outline of Physical Chemistry, John Wiley and Sons,

New York, 1952, page 665. Preferred compounds suitable for use in the practice of this invention are those compounds which are members selected from the class consisting of ammonium hydroxide and the oxides, hydroxides, carbonates, and lower organic acid salts of magnesium, calcium, strontium, barium, zinc and cadmium. Particularly preferred compounds which can be employed as stabilizers in the instant invention include, among others, calcium oxide, calcium hydroxide, calcium carbonate, calcium acetate, barium oxide, barium hydroxide, barium carbonate, barium acetate, zinc oxide, zinc hydroxide, zinc carbonate, zinc acetate, cadmium oxide, cadmium hydroxide, cadmium carbonate, cadmium acetate, and the like. a

The amount of stabilizer or buffering agent which can be added is not necessarily critical and all that is needed is a stabilizing amount sufficient to stabilize the polyepoxide from hydrolysis. This amount will vary from about 0.01 percent to about 5 percent by weight of textile treating solution or higher. Preferably, however, from about 0.1 percent to about 2 percent by weight is sufiicient. Concentrations above and below these amounts can equally as well be employed but are less preferred. It has been observed that an aqueous solution containing 15 percent by weight of solution of the methylglycidyl ethers end 1.5 percent by weight of zinc fluoborate may be conveniently stabilized at 25 C. by the addition of approrimately 0.4 percent by weight ofthe solution of zinc 0x1 e.

In still another aspect of the present invention, the stabilized textile treating solutions can include mixtures of one of more polyepoxides and one or more known textile finishes, particularly the nitrogen-containing finishes, either alone or in the presence of an epoxy curing catalyst. The undesirable yellowing efiect of the nitrogenous textfle resins after chlorine bleaching when such resins are used as the sole finish for white goods,is eliminated or greatly reduced when employed in conjunction with polyepoxides. Additionally, the combined finishes have a synergistic effect with enhanced wash-and-wear properties. Thus, excellent results are obtained, for example, by the use of the methylglycidyl ethers in conjunction with the melamine-formaldehyde resins, 1,3-dimethylol-5-ethyltetra-hydro-5-triazin-2(1H)-one; monoand dimethylol ureas, monoand dimethylol ethylene ureas, methylated methylol ureas, and the like.

The textile treating solutions employed for imparting the wash-and-wear characteristics to the cellulosic or cellulosic-containing materials can also contain, in addition to the aforementioned polyepoxides and nitrogenous textile resins, plasticizers, natural resins, textile softening agents and the like.

While the curing step can be accomplished by heating, it can be accelerated by the use of a suitable epoxy curing catalyst. A variety of catalysts are useful in the process of this invention with the boron trifluoride complexes being preferred. Other acids, acidic salts, and Lewis acids are also suitable for this purpose. Examples of epoxy curing catalysts are the fluoborates of magnesium, tin, cadmium and sodium as well as zinc; boron trifluoride etherate, stannic chloride, boric acid, the alkane sulfonic acids, aluminum chloride, hydrochloric acid, phosphoric acid, oxflic acid, magnesium chloride, sodium sulfate, zinc sulfate, aluminum sulfate, and the like. The amount of catalyst employed is not necessarily critical and can vary in amount from about 0.01 percent to about percent by weight, with a preferred range of from about 0.1 percent to about 5 percent.

The amount of polyepoxide to be applied to the textile material is an amount sufiicient to give a desired washand-wear rating of 4 or 5 as hereinafter indicated. A preferred method is to immerse the fabric in an aqueous solution containing from about 1 to about 30 percent by weight of the epoxy, preferably 3 to 20 percent, and from 0.01 to 10 percent of the epoxide curing catalyst and then pass it through a squeeze roller. A second immersion and squeezing can be efiected if necessary, leaving the fabric impregnated with approximately 60-120 percent of its own weight of solution. After this padding procedure, the fabric is mounted on a pin frame and dried at relatively low temperatures to remove water. While drying may be accomplished by allowing the fabric to remain in contact with the air, a temperature range of from about 35 C. to about 80 C. for 5 to 1 minutes is preferred. Since the drying time is not critical, a wider range of drying temperature can be employed equally as well.

Upon drying, the fabric is cured at a temperature sufiicient to promote the reaction of the polyepoxide with the fibrous material being treated. Temperatures from about 200 C. to about 120 C. and more preferably 160 C. to 120 C. can be employed for periods ranging from about seconds to about 15 minutes, with the higher temperatures using the shorter curing period. Although the methylglycidyl ethers can be cured over the broad temperature range noted above, they are particularly unique in that they can be cured at low temperatures with consequently less damaging effect on the fabric.

After the curing step, the fabric is scoured to remove unreacted polyepoxide or epoxy curing catalyst. Scouring is effected by washing in hot water (5080 C.) containing a small quantity of detergent. The scouring conditions themselves are not critical as long as unreacted material is removed from the fabric. After scouring, the fabric is dried and evaluated.

The cellulosic textile fabrics used to illustrate the process of this invention were x 80 cotton print cloth and 80 x 80 staple rayon fabric. The fabric was white, had been scoured and bleached, and was in suitable condition for application of resin treatment.

In the evaluation of the properties of the treated fabric, the following tests were conducted:

(a) Breaking strength; measured by the raveled strip method (American Society for Testing Materials D39- 49).

(b) Crease recovery; measured with the Monsanto tester (American Society for Testing Materials D1295- 531). By this test the ability of a fabric to recover from a crushing fold is measured.

(0) Dimensional stability; American Association of Textile Chemists and Colorists, tentative test method 40- 52.

(d) Wash and Wear evaluation; by means of the following scale, the wash-and-wear" properties of the treated material were evaluated.

Scale: Evaluation 5 As ironed.

4 Wearable. 3 Needs ironing. 2 Not acceptable. 1 Very wrinkled.

Ref: Textile Research Journal, 26, 974 (1956) American Dyestufi Reporter, 43, 37 (1959).

(2) Color; the yellowness of the treated fabric was determined by comparison with the original bleached fabric. The yellowness index was determined using a Hunter multi-purpose refiectometer. This abridged spectrophotometer employs three filters in measuring the 45, 0 reflectance of a fabric with respect to amber, green and blue light. A simple yellowness index is provided by Yellowness= Example I A treating solution was prepared which contained 20 percent by weight of diethylene glycol bis(2,3epoxy-2- methylpropyl)ether and 0.5 percent by weight of zinc fluoborate, the remainder being water. A sample of 80 x 80 cotton print cloth was immersed in this solution, padded to a wet pick-up of 98 percent of the fabric weight and dried for five minutes at 40 C. The fabric was cured for 3 minutes at C. and then laundered with a 0.1 percent solution of a built anionic detergent to remove residual reagents. After drying and conditioning to 65 percent relative humidity, the dry add-on was found to be 14.3 percent. The crease recovery of the treated sample was 78 percent, the breaking strength retained was 66 percent of the original fabric, and the sample had a wash-and-wear index of 3.

The original untreated fabric was immersed in water, dried and found to have a crease recovery of only 44 percent.

Example I] A sample of 80 x 80 cotton print cloth was treated in a manner similar to that described in Example 1, except that the concentration of zinc fiuoborate catalyst was 1.0 percent by weight of the treating solution and the fabric was cured for 3 mintues-at 160 C. The treated fabric had a dry add-on of 14.3 percent, a crease recovery of 79 percent, a' breaking strength retention of 64 percent and a wash-and-wear index of 4.

Example III A sample of 80 x 80 cotton print cloth was treated in a manner similar to that described in Example 11, except that the concentration of zinc fiuoborate catalyst was 4.0 percent by weight of the treating solution. The treated sample had a dry add-onof 12.0 percent, a crease recovery of 75 percent, a breaking strength retention of 63 pereentand a wash-and-wear index of 4.

Example IV A sample of 80 x 80 cotton print cloth was immersed in a treating solution which contained 20 percent by Weight of'ethylene glycol bis(2,3-epoxy-2-methylpropyl)- ether and 1.6 percent by weight of zinc fluoborate, the remainder being water. The sample was dried for minutes at 38 C., cured for 2 minutes at 191 C., and laundered to remove residual reactants. The treated fabric had a dry add-on of 7.4 percent, a crease recovery of 52 percent, a breaking strength retention of 67 percent, and a wash-and-Wear index of '3.

Example V A sample 80 x 80 cotton print cloth was immersed in a treating solution which contained 21.5 percent by weight of ethylene glycol bis(2,3-epoxy2-methylpropyl)ether, 1.4 percent by weight of zinc fiuoborate, and 0.4 percent of zinc oxide, the remainder being water. The sample was padded to a wet pick-up of 74 percent of the fabric weight and dried for 2.5 minutes at 77 C. The fabric was cured for 3 minutes at 120 C. and then laundered to remove residual reactants. The treated sample was found to have a dry add-on of 8.3 percent, a crease recovery of 71 percent, a breaking strength retention of 60 percent and a wash-and-wear index of 4.

Example VI A sample of 80 x 80 cotton print cloth was treated in a manner similar to that described in Example V, except that the zinc oxide buffering agent'was omitted and the solution was allowed to stand for 3 hours prior to padding. The sample waspadded to a wet pick-up of 82 percent by weight of the fabric. The sample was found to have a dry add-on of 8.6 percent, a crease recovery of 61 percent, a breaking strength retention of 70 percent and a wash-and-wear index of 2.

The stabilizing effect of the zinc oxide buffering agent on the hydrolysis of the polyepoxide is evident from the foregoing data.

Example VII A treating solution was prepared which contained 6.7 percent by weight of ethylene glycol bis(2,3-epoxy-2- methylpropyl)ether, 3.4 percent of dimethylol ethylene urea, 0.7 percent of zinc fluoborate, 0.5 percent zinc oxide and 88.7 percent water. A sample of 80 x 80 cotton print cloth was immersed in this solution and padded to a wet pick-up of 74 percent of the fabric Weight and dried for 3 minutes at 75 C. The fabric was cured for 3 minutes at 120 C. and then laundered to remove residual reactants. After drying the sample was found to have a dry add-on of 4.3 percent, a crease recovery of 69 percent, a breaking strength retention of 62 percent and a washand-wear index of 4.

Example Vlll A treating solution was prepared which contained 6.7 percent by weight of ethylene glycol bis((2,3-epoxy-2- methy1propyl)ether, 3.4 percent of 1,3-dimethylol-5- -ethyl-tetrahydro5-triazin(2H)-one, 1.4 percent of Zinc fluoroborate, 0.5 percent zinc oxide and 88 percent Water. A sample of 80 x 80 cotton print cloth was immersedin this solution and padded to ,a wet pick-up of 83 percent of the fabric weight and dried for 3 minutes at C. The fabric was'cured for 3 minutes at 160 C. and then laundered to remove residual reactants. After drying the sample was found to have a dry add-on of 4.9 percent, a crease recovery of '69 percent, a breaking strength retention of 62 percent and a wash-and-wear index'of 5.

. Example IX A treating solution was prepared which contained 6.7 percent by 'weight of ethylene glycol bis(2,3-epox-2- methy1propyl)ether, 3.4 percent of a modified melamineformal dehyde resin produced by American Cyanamid Co. and sold under the name Aerotex Resin MW, 0.7 percent zinc fluoborate, 0.5 percent Zinc oxide and 88.7 percent water. A sample of x 80 cotton print cloth was immersed in this solution and padded to a wet pickup of 82 percent of the fabric weight and dried for 3 minutes at 75 C. The fabric was cured for 3 minutes at C. and then laundered to remove residual reactants. After drying the sample was found to have a dry add-on of 4.4 percent, a crease recovery of 67 percent, a breaking strength retention of 65 percent and a Wash-and-wear index of 3.

Example X A treating solution was prepared which contained 20 percent by weight of bis(2,3-epoxy-2-methylpropyl)- ether, 1.6 percent by weight of zinc fiuoborate, 2 percent of poly(vinyl alcohol), the remainder being water. A sample of 80 x 80 cotton print cloth was padded to a wetpick-up of 95 percent of the fabric weight and dried for five minutes at 38 C. The fabric was cured for 2 minutes at C. and then laundered with a 0.1 percent solution of a built detergent to remove residual reagents. The treated fabric had a dry add-on of 8.5 percent, a crease recovery of 66 percent, a breaking strength retention of 59 percent and a wash-and-wear index of 3.

Although the invention has been illustrated by the preceding examples, the invention is not to be construed as limited to the materials employed in the above examples, but rather, the invention encompasses the generic area as hereinbefore disclosed. Various modifications and embodiments of this invention can be made without departing from the spirit and scope thereof.

What is claimed is:

1. A process for treating cellulosic and cellulosic-containing textile material whereby said material is rendered both shrink and crease resistant while imparting to said material after laundering a soft smooth finish without ironing which comprises impregnating said textile material with a textile treating solution comprising a monomeric polyepoxide having at least one group, an epoxy curing catalyst and then heating the textile material to cure the polyepoxide.

2. A process as claimed in claim 1 wherein the textile material is cotton.

3. A process as claimed in claim 1 wherein the textile material is rayon.

4. A process as claimed in claim 1 wherein the textile material is linen.

5. A process as claimed in claim 4 wherein the polyepoxide is bis(2,3-epoxy-2-methylpropy1)ether.

6. A process as claimed in claim 4 wherein the polyepoxide is ethylene glycol bis(2,3-epoxy-2.-rnethylpropyl)- ether.

7. A process as claimed in claim 4 wherein the polyepoxide is diethylene glycol bis(2,3-epoxy-2-methylpropyl)ether.

8. A process as claimed in claim 6 wherein the epoxide curing catalyst is zinc fluoborate.

9. A process as claimed in claim 4 wherein the fabric is heated within the temperature range of from about 200 C. to about 120 C. for a period of from about 15 seconds to about 15 minutes.

10. A process for treating cellulosic and cellulosic-containing textile material whereby said material is rendered both shrink and crease resistant while imparting to said material after laundering, a soft, smooth finish without ironing which comprises impregnating said textile material with a textile treating solution comprising a monomeric polyepoxde having at least one CH3 CH7-CH7O- group, an epoxy curing catalyst, a buffering agent and then heating the textile material to cure the polyepoxide.

11. A process for treating cellulosic and cellulosiccontaining textile material whereby said material is rendered both shrink and crease resistant while imparting to said material after laundering, a soft, smooth finish without ironing which comprises impregnating said textile material with a textile treating solution comprising a monomeric polyepoxide having at least one group, and from about 0.01 to about 10 percent by weight of an epoxy curing catalyst and heating the textile material to cure the polyepoxide.

References Cited in the file of this patent UNITED STATES PATENTS Condo et al June 26, 1956 Thomas Apr. 1, 1958

Claims

1. A PROCESS FOR TREATING CELLULOSIC AND CELLULOSIC-CONTAINING TEXTILE MATERIAL WHEREBY SAID MATERIAL IS RENDERED BOTH SHRINK AND CREASE RESISTANT WHILE IMPARTING TO SAID MATERIAL AFTER LAUNDERING A SOFT SMOOTH FINISH WITHOUT IRONING WHICH COMPRISES IMPREGNATING SAID TEXTILE MATERIAL WITH A TEXTILE TREATING SOLUTION COMPRISING A MONOMERIC POLYEPOXIDE HAVING AT LEAST ONE