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Publication numberUS3215488 A
Publication typeGrant
Publication dateNov 2, 1965
Filing dateOct 18, 1962
Priority dateOct 18, 1962
Publication numberUS 3215488 A, US 3215488A, US-A-3215488, US3215488 A, US3215488A
InventorsSuiter Roger N
Original AssigneeDan River Mills Inc
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Novel treatments of textiles and textiles treated accordingly
US 3215488 A
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Description  (OCR text may contain errors)

Unitcd States Patent 3,215,488 NOVEL TREATMENTS 0F TEXTILES AND TEXTILES TREATED ACCGRDINGLY Roger N. Suiter, Danville, Va, assignor to Dan River Miils, Incorporated, Danville, Va., a corporation of Virginia No Drawing. Filed Oct. 18, 1962, Ser. No. 231,562 13 Claims. (Cl. 8116.4)

This invention relates to new methods of treating textiles and textiles treated accordingly. More particularly, this invention is directed to methods for creaseproofing textile fabrics and crease resistant fabrics obtained thereby.

It is well known that textiles can be provided with crease resistance by treatments with a large variety of nitrogen-containing compounds such as urea-formaldehyde, triazone-formaldehyde condensates and mixtures thereof. Many of these creaseproofing agents made from nitrogen-containing compounds are defective in that they retain chlorine brought into contact with them by bleaching operations. Such retained chlorine, in many instances, is released in the form of acidic materials during subsequent pressing to deteriorate and objectionably discolor the fabric. The retention of chlorine is attributed to the nitrogen content of the creaseproofing agent and various attempts have been made to provide creaseproofing agents which do not contain nitrogen in amounts which are likely to cause teuderizing and/or discoloration of fabrics to which they are applied. These attempts have not been entirely successful in that While this problem may have been solved, other equally serious problems have arisen.

Other creaseproofing agents containing no nitrogen have been prepared and employed on textiles with a large degree of success. However, certain of such agents are of low reactivity and require special techniques for maintaining the creaseproofing agent in intimate contact with the textile for a sufficient period and at a sufliciently high temperature to enable cross-linking to take place. In addition, certain of these creaseproofing agents are noxious or irritational and thus are unacceptable for plant use. Still others of these creaseproofing agents cause discoloration which is diflicult to remove by ordinary bleaching techniques without loss of crease resistance.

A principal object of this invention is to provide a novel creaseproofing treatment for textiles which does not require special techniques or equipment and which will provide a novel treated textile having high crease resistance and substantially no chlorine retention capabilities.

Another object is the provision of a novel textile treatment which does not entail the use of noxious or irrita ing agents and which is readily adaptable for general plant use in existing facilities.

A further object is the provision of novel textile treatments for producing treated textiles which can be readily bleached in existing bleaching facilities without danger of discoloration or loss of crease resistance.

Another object of this invention is the provision of methods for treating textiles to impart crease resistance thereto without causing discoloration.

Another object is the provision of novel textile treatments for producing treated textiles which are characterized by a high crease resistance and a high tear strength.

Further objects and advantages of this invention are readily apparent in the following description.

Crease resistance is imparted to cellulosic fabrics in accordance with this invention by reacting the fabric with a creaseproofing amount of a cross-linking compound selected from the class consisting of glycidaldehyde and lower alkanol reaction products thereof. The invention is advantageously carried out by impregnating the fabric with a treating solution of the above-mentioned cross-linking compound in a suitable solvent, and heat curing the resulting impregnated fabric in the presence of catalytic amounts of an acidic or basic catalyst. It is preferable to employ an aqueous treating solution of glycidaldehyde or its lower alkanol derivatives, although, if desired or necessary, solutions thereof in any solvent capable of penetrating the cellulosic fabric can be employed. The catalyst is conveniently applied to the fabric as a component of the treating solution of glycidaldehyde or its lower alkanol derivatives or can be applied prior to impregnation with the treating solution.

The amount of cross-linking compound applied to the fabric being treated is not narrowly critical and can vary, for example, from 0.4 to 8.0 gram-moles or more per 1000 grams of fabric on a dry basis. It is advantageous to employ thecross-liuking compound in aqueous solution with a catalytic amount of the acidic or basic catalyst. The concentration of the cross-linking compound in the treating solution will depend upon the most convenient wet pick-up of the solution on the fabric with regard to the equipment being used and the desired production schedules. In general a 50 to 100 percent wet pick-up based on the dry weight of fabric is advantageous and a wet pick-up in the vicinity of 70 percent is preferred. A 5 weight percent to weight percent aqueous solution of the cross-linking compound is conveniently employed as the treating solution. The amount of catalyst is not narrowly critical and, for example, can vary from about 1 weight percent to about 20 weight percent based on the dry weight of fabric. Advantageous concentrations of the catalyst in the treating solution range from about 2 weight percent to about 30 weight percent based on the weight of the treating solution.

While glycidaldehyde is the preferred cross-linking compound employed herein, the lower alkanol reaction products of glycidaldehyde under acid conditions also provide the advantageous results obtained by the use of glycidaldehyde in treating fabrics. By the term lower alkanol as employed herein is meant an alkanol having from 1 to 4 carbon atoms, such as methanol, ethanol, propanol, butanol, and the like. The lower alkanol reaction products include those wherein from 1 to 3 moles of a lower alkanol are reacted with one mole of glycidaldehyde. Such reaction products include the dimethyl acetal of 2-1ydroxy-3-methoxypropionaldehyde, diethyl acetal of 2-hydroxy-3-ethoxypropionaldehyde, the dipropyl acetal of 2-hydroxy-3-propoxypropionaldehyde, the dibutyl acetal of 2-hydroxy-3-butoxypropionaldehyde, and the like.

Suitable acidic and basic catalysts include ammonium sulfate, sodium bicarbonate, sodium carbonate, sodium hydroxide, Zinc nitrate, sodium silicate, Zinc silicofluoride, zinc chloride, monoethanolamine hydrocholride, magnesium chloride, and the like. Preferred catalysts are the acidic metal fluoborates including zinc fiuoborate, nickel fluoborate, copper fluoborate, selenium fluoborate, magnesium fiu'oborate, tin fluoborate, strontium fluoborate, and the like.

The treating solution can also contain other materials for providing special or desired effects, such materials including suitable wetting agents, lubricants, whiteners, and the like.

After impregnating the fabric with the treating solution, the impregnated fabric is either dried and cured in one operation or is first dried and then cured. It is preferable to dry the impregnated fabric under such conditions that the moisture content thereof is suitably reduced prior to curing. For best results, the drying conditions should not be so severe that the curing of the impregnated fabric is begun. It is preferable to dry the fabric at ambient temperatures in the air or to add vaporization suppressors, such as high molecular weight polyethylene glycols, e.g., those having an average molecular weight of about 20,000, and then to dry at elevated temperatures. In general, drying should be sulficient to provide a relatively low moisture content, for example, of about 3 weight percent, prior to commencement of the curing.

Curing of the dried impregnated fabric is conducted under conditions which will react the cross-linking compound with the cellulosic fabric sufiiciently to provide the desired crease resistance. The exact curing conditions to be employed will depend upon the specific fabric being treated, the particular equipment being used, and other factors. Curing conditions which are too severe may give rise to excessive yellowing of the fabric and, of course, severe conditions which will burn or heat-decompose the fabric to weaken or destroy it should not be used. Curing conditions which are so mild as to excessively volatilize the cross-linking compound without causing a reaction between it and the fabric are also to be avoided. In general, the fabric is best cured at 80 to 160 C. for 30 seconds to minutes.

After curing, the fabric can then be subjected to the usual after-treatments, such as bleaching, bluing top softening compressive shrinking, and the like.

The following examples are presented. In these examples all percentages are based on weight. The crease resistance values were determined by the Monsanto Crease Recovery Test (A.A.T.C.C. Tentative Test Method 66- 1959T) and the filling tear values were determined by the trapezoid method.

EXAMPLE 1 A treating solution was prepared containing percent glycidaldehyde, 6 percent of a 40 percent aqueous solution of zinc fiuoborate, and the remainder of water. The treating solution was padded onto untreated, mercerized cotton cloth (40/ 1, 80 x 80) to a 70 percent wet pick-up. Thereafter, the impregnated cloth was air dried and then cured for 1 /2 minutes at 120 C. It was then given a warm rinse in a 2 percent aqueous solution of a percent solids emulsion of polyethylene for 5 minutes followed by drying by pressing. The cloth treated in this manner had a wet crease resistance of 248 (warp plus filling), a dry crease resistance of 293 (warp plus filling), and a filling tear strength of 2.1 pounds.

EXAMPLE 2 A solution of 100 grams of 5 percent aqueous hydrochloric acid and 96 grams of methanol was prepared and slowly added with stirring to 72 grams of glycidaldehyde. The resulting mixture was covered and allowed to stand overnight. A treating solution containing percent of the resulting mixture, 6 percent of a percent solution of zinc fiuoborate, and the remainder of water was prepared. This treating solution was padded onto untreated, mercerized cotton cloth (40/1, 80 x 80) to a 70 percent wet pick-up. The impregnated cloth was allowed to air dry and thereafter was cured for 1 /2 minutes at 120 C. After curing, the cloth was given a warm rinse for 5 minutes in a 2 percent solution of a 25 percent solids aqueous emulsion of polyethylyene and then given a 15 minute soak in an 0.6 percent aqueous soda ash solution. The cloth then was pressed dry. The cloth treated in this manner had a wet crease resistance of 250 (warp plus filling), a dry crease resistance of 284 (warp plus filling), and a filling tear strength of 1.8 pounds.

EXAMPLES 39 Improved crease resistance was obtained in each of the following examples wherein each treating solution contained 15 grams of glycidaldehyde, 2 grams of a 25 percent solids aqueous emulsion of polyethylene as softener, 77 grams of water and 6 grams of the type of catalyst set forth in Table I below:

cerized cotton cloths (40/1, 80 x 80) to a 70 percent wet pick-up. The impregnated cloths were allowed to air dry and thereafter were cured for 1 /2 minutes at C. After curing, the cloths were given a warm water rinse for 5 minutes followed by pressing and drying.

EXAMPLES 10-12 Improved crease resistance was obtained in each of the following examples wherein each treating solution contained 15 grams of glycidaldehyde, 75 grams of water and 10 grams of the type of catalyst set forth in Table II below:

Table II Example: Catalyst 10 50 percent aqueous magnesium chloride. 11 20 percent aqueous zinc chloride. 12 23 percent aqueous monoethanolamine hydrochloride. The treating solutions were padded onto untreated, mercerized cotton cloths (40/ 1, 80 x 80) to a 70 percent wet pick-up. The impregnated cloths were allowed to air dry and thereafter were cured for 70 seconds at C. After curing, the cloths were given a warm rinse for 5 minutes in an aqueous solution of 0.005 percent soda ash and 5 percent Clorox bleach. The cloths were then dried by pressing.

What is claimed is:

1. A process for creaseproofing cellulosic fabric, comprising heating said fabric with a cross-linking compound from the class consisting of glycidaldehyde and lower alkanol reaction products thereof in the presence of a catalytic amount of a catalytic salt from the class consisting of acidic and basic catalysts, at a temperature of at least 80 C. until crease resistance is obtained.

2. A process for creaseproofing cellulosic fabric, comprising heating said fabric with a cross-linking compound from the class consisting of glycidaldehyde and lower alkanol reaction products thereof in the presence of a catalytic amount of an acidic metal fiuoborate catalyst, at a temperature of at least 80 C. until crease resistance is obtained.

3. A process for creaseproofing cellulosic fabric, comprising heating said fabric with glycidaldehyde in the presence of a catalytic amount of zinc fiuoborate, at a temperature of at least 80 C. until crease resistance is obtained.

4. A cellulosic fabric treated by the process claimed in claim 1.

5. A cellulosic fabric treated by the process claimed in claim 2.

6. A- cellulosic fabric treated by the process claimed in claim 3.

7. A process for creaseproofing cellulosic fabric, comprising heating said fabric with the reaction product of glycidaldehyde and methanol in the presence of a catalytic amount of zinc fiuoborate, at a temperature of at least 80 C. until crease resistance is obtained.

8. A cellulosic fabric treated by the process claimed in claim 7.

9. The process as claimed in claim 1 wherein the catalyst is selected from the group consisting of ammonium sulfate, sodium bicarbonate, sodium carbonate, sodium hydroxide, zinc nitrate, sodium silicate, Zinc silicofluoride, zinc chloride, monoethanolamine hydrochloride, magnesium chloride and metal fluoborates.

10. A process for creaseproofing cellulosic fabric, comprising heating said fabric with a cross-linking compound from the class consisting of glycidaldehyde and lower alkanol reaction products thereof in the presence of a catalytic amount of an acidic metal fluoborate catalyst, and thereafter curing the heated fabric at a temperature of at least 80 C. until crease resistance is obtained.

11. A process for creaseproofing cellulosic fabric, comprising heating said fabric With an aqueous solution of a cross-linking compound from the class consisting of glycidaldehyde and lower alkanol reaction products thereof in the presence of a catalytic amount of an acidic metal fluoborate catalyst, at a temperature of at least 80 C. until crease resistance is obtained.

12. The method as claimed in claim 11, wherein the aqueous solution contains from 5 weight percent to 80 weight percent of the cross-linking compound.

13. The method as claimed in claim 2, wherein the catalyst is from about 1 to 20 Weight percent based on the dry weight of the fabric.

References Cited by the Examiner UNITED STATES PATENTS 2,833,787 5/58 Carlson.

2,938,040 5/60 Skinner et al. 260348 2,947,761 8/60 Payne.

3,067,175 12/62 Sullivan et al 260-3485 NORMAN G. TORCHIN, Primary Examiner.

Patent Citations
Cited PatentFiling datePublication dateApplicantTitle
US2833787 *Mar 15, 1955May 6, 1958Shell DevEpoxidation process using hydrogen peroxide and an acid salt of a heavy metal peracid
US2938040 *Sep 9, 1957May 24, 1960Shell Oil CoEpoxidation of unsaturated aldehydes
US2947761 *Jun 2, 1958Aug 2, 1960 Epoxtoation of aldehydes
US3067175 *Mar 7, 1960Dec 4, 1962Shell Oil CoPolyglycidaldehyde
Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US3337488 *Jan 22, 1965Aug 22, 1967Gulf Oil CorpProcess for hydrolyzing ethylenealkyl acrylate copolymers with aqueous ammonia
US3880830 *Sep 21, 1972Apr 29, 1975Us AgricultureProcess for acylating functional groups bearing active hydrogen with isopropenyl esters of long-chain fatty acids
US4135969 *Feb 25, 1974Jan 23, 1979Nalco Chemical CompanyGlycidaldehyde modified cationic polyacrylamide polymers used in paper
US4152115 *Feb 15, 1978May 1, 1979The United States Of America As Represented By The Secretary Of AgricultureProcess for imparting water repellancy to fibrous cellulosic textile materials by acylating with isopropenyl esters
US6841198Oct 9, 2002Jan 11, 2005Strike Investments, LlcDurable press treatment of fabric
US6989035Oct 9, 2002Jan 24, 2006The Procter & Gamble CompanyTextile finishing composition and methods for using same
US7008457Oct 9, 2002Mar 7, 2006Mark Robert SivikTextile finishing composition and methods for using same
US7018422Oct 9, 2002Mar 28, 2006Robb Richard GardnerShrink resistant and wrinkle free textiles
US7144431Oct 9, 2002Dec 5, 2006The Procter & Gamble CompanyTextile finishing composition and methods for using same
US7169742Oct 9, 2002Jan 30, 2007The Procter & Gamble CompanyForming a textile finishing agent with superior clarity; discoloration inhibition
US7247172Dec 12, 2005Jul 24, 2007The Procter & Gamble CompanyFormaldehyde-free fabric finishes comprising a cross-linked polymaleic acid with phosphinate or phosphonates, or a compound of phosphonated maleic acid; wash and wear
Classifications
U.S. Classification8/116.4, 8/120, 536/99, 442/107, 536/56, 8/116.1, 427/394
International ClassificationD06M13/127, D06M13/00
Cooperative ClassificationD06M13/127
European ClassificationD06M13/127