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Soane et al,(10) Pub. No.: US 2002/0120988 Al(43) Pub. Date: Sep. 5, 2002

(54) ABRASION-AND WRINKLE-RESISTANTFINISH FOR TEXTILES Publication Classification

(75) Inventors: David S. Soane, Piedmont, CA (US);William Ware JR., Portola Valley, CA(US); David A. Offord, Castro Valley,CA(US)

(51) Int. CI? D06M 10/00(52) U.S. CI. 8/1l5.51(57) ABSTRACT

(73)(21)(22)

Appl. No.: 10/084,031

This invention is directed to treatment preparations usefulfor the permanent or substantially permanent treatment oftextiles and other webs to provide tear and abrasion strengthand softness to durable-press garments. The preparationscomprise a softener (a "resin-reactive modifier") durable torepeated laundering used in conjunction with a durable-pressresin, to increase the comfort and lifetime of durable-pressgarments. The resulting durable-press/softener preparationis substantially permanently attached to the web and pro-vides improved softness and tear/abrasion strength retentionwithin and/or on the textile or web fiber structure whileretaining the durable-press properties of the resin. Thisinvention is further directed to the yarns, fibers, fabrics,textiles, finished goods, or nonwovens (encompassed hereinunder the terms "textiles" and "webs") treated with thetextile-reactive durable-press/softener preparation. Suchtextiles and webs exhibit a greatly improved, durable soft-ness and tear/abrasion strength.

Correspondence Address:JACQUELINE S LARSONPO BOX 2426SANTA CLARA, CA 95055-2426 (US)Assignee: Nano-Tex, LLC

Filed: F e b . 2 7 , 2 0 0 2Related U.S. Application Data

(63) Continuation of application No. PCT/USOO/24581,filed on Sep. 8, 2000.

(60) Provisional application No. 60/153,375, filed on Sep.10, 1999.

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ABRASION-AND WRINKLE-RESISTANT FINISHFOR TEXTILES[0001] The present invention is a continuation applicationof co-pending International Patent Appln. No. PCT/USOO/24581, filed Sep. 8, 2000 and designating the United Statesof America, which application claims the benefit of Provi-sional U.S. application Ser. No. 60/153,375, filed Sep. 10,1999; the entire disclosures of which are incorporated hereinby reference.

FIELD OF THE INVENTION[0002] The present invention relates to textile treatmentcompositions for imparting permanent abrasion- andwrinkle-resistance to textiles.

BACKGROUND OF THE INVENTION[0003] Cotton consists of cellulose, a polysaccharide. Thecellulose molecules in a cotton fiber are arranged linearlyand pass in and out of crystalline and amorphous regions andare held in place by hydrogen bonds between the molecules.Slippage between the cellulose chains or between largerstructural units of the fiber occurs when a force of sufficientmagnitude is placed on the fiber. The hydrogen bonds tendto resist or prevent the slippage, but once slippage occurs thebonds reform in new locations and tend to maintain the fiberin the bent or wrinkled state. In addition, cotton fiber ishydrophilic and absorbs water, which can break hydrogenbonds and allow the fiber or fabric to shrink. Thus, 100%cotton wrinkles easily and has the potential to shrink uponlaundering.[0004] Cellulose is made up of repeating anhydroglucoseunits. Each unit contains two secondary and one primaryalcohol groups. To achieve wrinkle resistance, alcoholgroups on adj acent cellulose chains are partially crosslinkedto keep the chains fixed relative to each other. Over theyears, a number of crosslinking agents (resins) have beenexplored to achieve durable-press properties. Some includeisocyanates, epoxides, divinylsulfones, aldehydes, chloro-hydrins, N-methylol compounds, and polycarboxylic acids.Of these, N-methylol compounds have been used the most.Examples include dimethylol urea, dimethylol ethyleneurea, trimethylol trazine, dimethylol methyl carbamate,uron, triazone, and dimethylol dihydroxy ethylene urea.Dimethylol dihydroxy ethylene urea (DMDHEU) is themost common durable-press finish used today.[0005] Resins improve wrinkle recovery, fabric smooth-ness, dimensional stability, washfastness of some dyes,pilling resistance, ease of ironing, durability of finishes(repellents, hand modifiers, embossing, etc.), and generalappearance. However, crosslinking has its disadvantages,including loss in tear and tensile strength, loss in abrasionresistance, reduced moisture regain, possible damage due tochlorine retention, potential odors, potential discoloration,and sewing problems. Durable-press fabrics also often havestiff, harsh, uncomfortable fabric tactile (hand) properties.Therefore, fabric softeners/lubricants are commonly addedto these fabrics to mitigate some of these deficiencies.Softeners improve the hand of the fabric as well as increaseabrasion resistance and tear strength. The softener alsofunctions as a sewing lubricant. There are four basic types ofsofteners-anionic, cationic, nonionic, and blended systems.

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[0006] The anionic softeners are generally sulfated orsulfonated compounds used primarily to lubricate yarnsthrough processing. Examples of these compounds includesulfonated tallow, glycerides, and esters. Sulfonated or sul-fated castor oil, propyl oleate, butyl oleate, and tallow areused in various steps in dying fabrics. Anionics tend toprovide inferior softness compared to the cationics andnonionics. Furthermore, they have limited durability tolaundering or dry-cleaning. Their major limitation comesfrom their negative charge, which causes incompatibility inresin finishing baths and makes them most sensitive to waterhardness and electrolytes.[0007] The cationic softeners are nitrogen-containingcompounds including fatty amino amides, imidazolines,amino polysiloxanes, and quaternaries. As a result of theirpositive charge, they are attracted to cotton or syntheticfabrics through electrostatic interactions. They tend to becompatible with most resin finishes and are somewhatdurable to laundering. The most significant disadvantage ofcationic softeners is their tendency to change the shade oraffect the fastness of certain dyestuffs. Discoloration onwhite fabrics may also be a concern. The development of afishy odor on the fabric can be a problem with certainsystems.[0008] Nonionics are the most widely used softeners. Thisclass includes polyethylenes, glycerides such as glycerolmonostearate, ethoxylates such as ethoxylated castor wax,coconut oil, corn oil, etc., and ethoxylated fatty alcohol andacids. The nonionic softeners offer excellent compatibility inresin baths due to their uncharged state. Since nonionicshave no charge, they have no specific affinity for fabrics andtherefore have relatively low durability to washing.[0009] To optimize softening and lubricating properties,many manufacturers tend to formulate a softener containingboth nonionic and cationic types. Typically, an aminosili-cone or an imidazoline for a silky soft slick hand will beblended with a cationic or a nonionic polyethylene lubricantfor sewability and tear- and abrasion-strength properties.Increased customer demand for improved durability anduseful life of a garment has led to the use of high-densitypolyethylenes as softeners. Polyethylenes have decreasedsolubil ity in detergent solutions,which results in increasedsoftener durability. However, the disadvantages of the soft-eners (such as, for example, lack of durability to repeatedlaunderings) remain.

SUMMARY OF THE INVENTION[0010] This invention is directed to treatment preparationsuseful for the permanent or substantially permanent treat-ment of textiles and other webs to provide tear and abrasionstrength and softness to durable-press garments. The prepa-rations comprise a softener (referred to herein as a "resin-reactive modifier") durable to repeated laundering used inconjunction with a durable-press resin, to increase the com-fort and lifetime of durable-press garments. More particu-larly, the preparations of the invention comprise a "rubbery"resin-reactive modifier capable of reacting with a durable-press resin during textile treatment. By "reacting" is meantthat the polymer will form a covalent bond with the durable-press resin and the resin will form a covalent bond to thefiber, textile, or web to be treated. The resulting durable-press/softener preparation is substantially permanently

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attached to the web and provides improved softness andtear/abrasion strength retention within and/or on the textileor web fiber structure while retaining the durable-pressproperties of the resin through repeated launderings.[0011] This invention is further directed to the yarns,fibers, fabrics, textiles, finished goods, or nonwovens(encompassed herein under the terms "textiles" and "webs")treated with the textile-reactive durable-press/softenerpreparation. Such textiles and webs exhibit a greatlyimproved, durable softness and tear/abrasion strength. By"durable softness and tear/abrasion strength" and "durablewrinkle resistance, a soft hand, and tear/abrasion resistance"are meant that the textile or web will exhibit improvedsoftness and resistance to tear and/or abrasion, even aftermultiple launderings, while retaining its durable press orresistance to wrinkling.[0012] Methods are provided for treating fabrics to impartpermanent wrinkle resistance as well as permanent softnessand tear/abrasion resistance by combining a "rubbery" resin-reactive modifier with durable-press resins.

DETAILED DESCRIPTION OF IREINVENTION

[0013] The textile-reactive preparations of the inventioncomprise a combination of i) a durable-press resin capableof imparting wrinkle resistance and ii) a resin-reactivemodifier capable of imparting a soft hand and tear/abrasionresistance to textiles.[0014] The resin-reactive modifier useful in the presentinvention comprises particular monomers, oligomers, orpolymers having hydroxyl-c-or other reactive group-con-taining monomers, or mixtures thereof (referred to hereinand in the appended claims as "reactive building blocks"),copolymerized with soft, rubbery or elastomeric monomersor polymers (referred to herein and in the appended claimsas "rubbery building blocks"). The resin-reactive modifiermay also comprise rubbery building blocks that are pro-cessed post-polymerization to include hydroxyl-c-or otherreactive groups. The resin-reactive modifier is capable ofreacting with a durable-press resin during textile treatment.By "reacting" is meant that the resin-reactive polymer willform a covalent bond with the durable-press resin. The resinin turn will form a covalent bond to the fiber, textile, or webto be treated. The resin-reactive modifier will impart a softhand to the resin-treated textile and also provide tear and/orabrasion resistance to the textile. This resin-reactive modi-fier, because of its covalent bonding to the textile through thewrinkle-resistant resin, is durable to laundering and is per-manent, and it significantly increases the comfort and life-time of durable-press garments.[0015] The rubbery groups of the resin-reactive modifierare selected from those groups that will provide the neces-sary softness and tear/abrasion resistance. Examples includepolymers of isoprene, chloroprene, butadiene, ethylene, iso-propylene, ethyleneoxide, isobutylene, propylene, chlori-nated ethylene, and polymers such as polydimethylsiloxane,polyisobutylene, poly-alt-styrene-co-butadiene, poly-ran-dom-styrene-co-butadiene, etc., and copolymers of all ofthese. The rubbery group is copolymerized in such a pro-portion as to take about 60% to about 99.8% by weight,preferably about 80% to about 95% by weight, of theresin-reactive modifier copolymer of this invention.

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[0016] The reactive groups on the resin-reactive modifierare selected from those groups that will bind chemicallywith a particular durable-press resin. For example, groupsmay consist of hydroxyls, amines, amides, or thiols. In apresently preferred embodiment, the resin modifier isselected from polymers containing at least one hydroxylgroup per molecule.[0017] The durable-press resin is chosen from those thatwill bind chemically with a particular fiber, yarn, fabric, orfinished good. For example, cellulosic-based webs such aspaper, cotton, rayon, linen, and jute contain hydroxyls.Wool, which is a proteinaceous animal fiber, containshydroxy Is, amines, carboxylates, and thiols.[0018] Specific amine-reactive groups (for reaction withwool, for example) include isothiocyanates, isocyanates,acyl azides, N-hydroxysuccinimide esters, sulfonyl chlo-rides, aldehydes and glyoxals, epoxides and oxiranes, car-bonates, arylating agents, imidoesters, carbodiimides, anhy-drides (such as maleic anhydride), and halohydrins.Carboxylate-reactive groups (for reaction with wool, e.g.)include diazo alkanes and diazo acetyl compounds, carbonyldiimidazole, and carbodiimides. Hydroxyl-reactive chemi-cal reactions (for, e.g., wool and cotton) include couplingswith epoxides and oxiranes, carbonyl diimidazole, N,N'-disuccinimidyl carbonate or N-hydroxysuccinimidyl chlo-roformate, alkyl halogens, isocyanates, and halohydrins,oxidation with periodate, and enzymatic oxidization.Examples of thiol-reactive chemical reactions (for wool, forexample) include couplings with halo acetyl and alkyl halidederivatives, maleimides, aziridines, acryloyl derivatives,arylating agents, and disulfide-forming reactions mediatedby exchange reagents (such as pyridyl disulfides, disulfidereductants, and 5-thio-2-nitrobenzoic acid, for example).[0019] Durable-press resins useful in the present inventioninclude isocyanates, epoxides, divinylsulfones, aldehydes,chlorohydrins, N-methylol compounds, and polycarboxylicacids, which compounds are known to those of skill in theart. N-methylol compounds have been used the most.Examples include dimethylol urea, dimethylol ethyleneurea, trimethylol trazine, dimethylol methyl carbamate,uron, triazone, and dimethylol dihydroxy ethylene urea(DMDHEU. Additionally, in the case of cotton, any com-pound capable of forming a crosslink between two hydroxylgroups may be used as the resin component.[0020] In a presently preferred embodiment, the durable-press/softener preparation comprises i) a resin modifierselected from polymers consisting of butadiene or hydroge-nated butadiene containing at least one hydroxyl group permolecule, and ii) the resin DMDHEU or cyanuric chloride.[0021] In forming the durably soft, tear/abrasion-resistanttextile, additional crosslinkers or complementary reactivefunctionalities may also be added to the solution of thedurable-press/softener preparation to help create bridgesbetween crosslinkable groups, to alter the crosslink density,and/or to add additional properties to the textile (for examplewater and stain resistance).[0022] The present invention is further directed to theyarns, fibers, fabrics, textiles, or finished goods (encom-passed herein under the terms "textiles" and "webs") treatedwith the durable-press/softener preparation. These noveltextiles or webs will display comparable durable-press per-

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formance without the harsh hand or the low tear and lowabrasion resistance of traditional durable-press textiles.[0023] These textiles, which exhibit wrinkle resistance asoft hand, and improved tear/abrasion resistance, can beused in a variety of ways including, but not limited to:clothing, especially those for, but not limited to easilywrinkled clothing, such as formal garments coats hatsshirts, pants, gloves, and the like; other textiles subject t~wear or tearing, such as awnings, draperies, upholstery foroutdoor furniture, protective covers for barbecues and out-door furniture, automotive upholstery, sails for boats, andthe like; and industrial uses, such as those listed in AdanurS., Wellington Sears Handbook of Industrial Textiles, p. 8-11'(Technomic Publishing Co., Lancaster, Pa., 1995).[0024] The novel webs of the present invention areintended to include fabrics and textiles, and may be asheet-like structure (woven, knitted, tufted, stitch-bonded, ornon-woven) comprised of fibers or structural elements. Thefibers may include non-fibrous elements, such as particulatefillers, binders, sizes and the like. The textiles or websinclude fibers, woven and non-woven fabrics derived fromnatural or synthetic fibers or blends of such fibers, as well ascellulose-based papers, and the like. They can comprisefibers in the form of continuous or discontinuous monofila-ments, multifilaments, staple fibers, and yarns containingsuch filaments and/or fibers, which fibers can be of anydesired composition. The fibers can be of natural, man-made, or synthetic origin. Mixtures of natural fibers, man-made fibers, and/or synthetic fibers can also be used.Examples of natural fibers include cotton, wool, silk, jute,linen, and the like. Examples of man-made fibers includeregenerated cellulose rayon, cellulose acetate and regener-ated proteins. Examples of synthetic fibers include polyes-ters (including polyethyleneglycolterephthalate), polya-mides (including nylon), acrylics, olefins, aramids, azlons,modacrylics, novoloids, nytrils, aramids, spandex, vinylpolymers and copolymers, vinal, vinyon, and the like.[0025] To prepare the permanent durable-press, soft, andtear/abrasion-resistant webs, the fiber, the yarn, the fabric, orthe finished good (the "textile" or "web") is exposed to theresin-reactive modifier suspended in an aqueous solution inthe presence of a suitable durable-press resin and suitablecatalyst for activating the resin (such as, for example, MgCl2or any Lewis acid), by methods known in the art such as bysoaking, spraying, dipping, fluid-flow, padding, and the like.The resin-reactive modifier and the durable-press resin maybe added together to the solution with the web or they maybe added sequentially. The textile-reactive functional groupsof the durable-press resin react with the web, by covalentbonding, to permanently attach to the web. The resin-reactive functional groups on the permanent softener-tear/abrasion resistant polymer react with the durable-press resin,by covalent bonding. The durable-press resin serves tocrosslink the cellulose chains, in the case of cotton forexample, while at the same time reacting with the reactivegroup-containing resin-reactive modifier, thus serving as acovalent bridge between the cellulose and the resin-reactivemodifier. The modifier may be linked by one or multiplehydroxyls to the cellulose through the resin. The treated webis then removed from the solution, dried, and cured.[0026] The concentration of the resin-reactive modifier insolution can be from about 0.1 wt % to about 10 wt %preferably from about 2 wt % to about 8 wt % mor~preferably about 8 wt %; depending, however, ~n thecharacteristics of the particular resin-reactive modifier

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selected (such as molecular weight or material) and on theamount of softening and tear/abrasion resistance desired.[0027] The concentration of the durable press resin mayvary, depending on the particular resin used and the finalcharacteristics of the product desired. For example, in thecase of DMDHEU, the manufacturer of the resin recom-mends 8 wt % DMDHEU to obtain permanently pressedtextiles, whereas a lower amount may be used when abrasionresistance without permanent press is desired.[0028] The process temperature can vary widely, depend-ing on the affinity of the durable press resin for the websubstrate and for the resin-reactive modifier. However, thetemperature should not be so high as to decompose thereactants or so low as to cause inhibition of the reaction orfreezing of the solvent. Unless specified to the contrary, theprocesses described herein take place at atmospheric pres-sure over a temperature range from about 120 C. to about180 c., more preferably from about 140 C. to about 160c., and most preferably at about 150 C. The time requiredfor the processes herein will depend to a large extent on thetemperature being used and the relative reactivities of thestarting materials. Therefore, the time of exposure of thetextile to the polymer in solution can vary greatly, forexample from about one minute to about two hours. Nor-mally, the exposure time will be from about one to about fiveminutes. Following exposure, the treated yarn or fabric isdried at ambient temperature or at a temperature aboveambient, up to about 90 c., possibly higher. The pH of thesolution will be dependent on the requirements of the resin,the resin-reactive modifier, and the textile. Typically, resin-crosslinking is optimized at low pH, but cotton, for example,degrades in acid, so a balance must be reached. Furthermore,the deposition of resin-reactive modifiers with chargedgroups (e.g., amines, carboxylates, and the like) is expectedto be dependent on solution pH. Salts (such as, for example,NaCI) may optionally be added to increase the rate ofadsorption of anionic and cationic polymers onto the fibers.Unless otherwise specified, the process times and conditionsare intended to be approximate.

EXAMPLESExample 1

Preparation of Resin-Reactive Modifier Solution[0029] Four percent (4%) by weight of hydroxy-termi-nated polybutadiene (PBD-OH, 1200 MW, [hydroxylj-L?meq/g, C!,:S# 69102-90-5, Aldrich, Milwaukee, Wis.) and4% by weight of Tween-40 (polyoxyethylene sorbitan ester,ICI Surfactants, Wilmington, Del.) were added to water withstirring to give an aqueous solution of hydroxy-terminatedresin-reactive modifier.

Example 2Application of Durable-Press/Softener Preparation

to 100% Cotton, and Physical Characterization[0030] Cotton fabric samples (400 series, Test Fabrics,West Pittston, Pa.) were treated in stirred aqueous solutionscontaining various percentages of hydroxy-terminatedpolybutadiene and Tween-40, prepared as described inExample 1 above. The samples were removed and dried at85 C. for 10 minutes. The samples were then treated witha commercial preparation of durable press resin (Freerez901, 38% buffered DMDHEU, BF Goodrich, Greenville,

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S.c.) and catalyst (Freecat LF, MgCl2 and citric acid, BFGoodrich, Greenville, S.c.) according to the manufacturer'sspecifications at 8% and 2% on bath weight, respectively.Fabric samples were dipped in 200% of fabric weight resinand catalyst solution and padded to 100% pick-up. Sampleswere dried at 85 C. for 10 minutes, followed by curing at160 C. for 4 min. Samples were tested for flex abrasion(measured using an ASTM 03885-92, at 4 lb tension and 1lb pressure) and wrinkle recovery (following the AATCCtest method #66-1998). Additionally, samples were washedin an accelerated laundering machine to simulate five homelaunderings. All sample treatments were done to mimic adip, pad, squeeze application method with approximately100% wet pick-up. The results are shown in Table I.

TABLE I

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imparting a soft hand and tear/abrasion resistance tosaid textile, said resin-reactive modifier comprisingreactive groups capable of forming a covalent bondwith said durable-press resin, and optionally, iii) acatalyst;

removing said treated textile from the aqueous solution;drying said treated textile; andcuring said treated textile;to give a treated textile that exhibits durable wrinkle

resistance, soft hand, and tear/abrasion resistance.7. A method according to claim 6 wherein said resin-

reactive modifier comprises reactive building blocks andrubbery building blocks.

Wrinkle recovery angle and flex abrasion cycles of various samples.# Home Wrinkle Flex Abrasion

Sample % PBD-OH % DMDHEU Launderings Recovery Angle CyclesPure Cotton 0 0 0 72 329 129o HLPure Cotton 0 0 5 70 455 955 HLDMDHEU Treated 0 8 0 135 168 91Cotton - 0 HLDMDHEU Treated 0 8 5 120 138 100Cotton - 5 HLPBD-OHjDMDHEU 4 8 0 128 585 120Treated Cotton - 0 HLPBD-OHjDMDHEU 4 8 5 127 737 291Treated Cotton - 5 HL

What is claimed is:1. A textile-reactive preparation comprising:a durable-press resin capable of forming a covalent bond

with a textile and capable of imparting wrinkle-resis-tance to said textile, and

a resin-reactive modifier capable of imparting a soft handand tear/abrasion resistance to said textile, said resin-reactive modifier comprising reactive groups capableof forming a covalent bond with said durable-pressresin.

2. A textile-reactive preparation according to claim 1wherein said resin-reactive modifier comprises reactivebuilding blocks and rubbery building blocks.

3. A textile-reactive preparation according to claim 2wherein said resin-reactive modifier comprises at least onehydroxyl reactive group per molecule.

4. A textile-reactive preparation according to claim 2wherein said resin-reactive modifier is selected from thegroup consisting of butadiene polymer and hydrogenatedbutadiene polymer comprising at least one hydroxyl reactivegroup per molecule.

5. A textile-reactive preparation according to claim 2wherein said durable-press resin is DMDHEU.

6. A method for treating a textile comprising:exposing a textile to an aqueous solution or suspension of

a textile-reactive preparation comprising i) a durable-press resin capable of forming a covalent bond withsaid textile and capable of imparting wrinkle-resistanceto said textile, ii) a resin-reactive modifier capable of

8. A method according to claim 7 wherein said resin-reactive modifier comprises at least one hydroxyl reactivegroup per molecule.

9. A method according to claim 7 wherein said resin-reactive modifier is selected from the group consisting ofbutadiene polymer and hydrogenated butadiene polymercomprising at least one hydroxyl reactive group per mol-ecule.

10. A method according to claim 7 wherein said durable-press resin is DMDHEU.

11. A treated textile prepared by the method comprising:exposing a textile to an aqueous solution or suspension ofa textile-reactive preparation comprising i) a durable-

press resin capable of forming a covalent bond withsaid textile and capable of imparting wrinkle-resistanceto said textile, ii) a resin-reactive modifier capable ofimparting a soft hand and tear/abrasion resistance tosaid textile, said resin-reactive modifier comprisingreactive groups capable of forming a covalent bondwith said durable-press resin, and optionally, iii) acatalyst;

removing said treated textile from the aqueous solution;drying said treated textile; andcuring said treated textile;said treated textile having the characteristic of exhibitingdurable wrinkle resistance, soft hand, and tear/abrasion

resistance.12. A treated textile according to claim 11 wherein said

resin-reactive modifier comprises reactive building blocksand rubbery building blocks.

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13. A treated textile according to claim 12 wherein saidresin-reactive modifier comprises at least one hydroxylreactive group per molecule.

14. A treated textile according to claim 12 wherein saidresin-reactive modifier is selected from the group consistingof butadiene polymer and hydrogenated butadiene polymercomprising at least one hydroxyl reactive group per mol-ecule.

15. A treated textile according to claim 12 wherein saiddurable-press resin is DMDHEU.

16. A resin-reactive modifier which comprises reactivegroups capable of forming a covalent bond with a durable-

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press resin and which is capable of imparting a soft hand andtear/abrasion resistance to a textile.

17. A resin-reactive modifier according to claim 16 whichcomprises reactive building blocks and rubbery buildingblocks.

18. A resin-reactive modifier according to claim 17 whichcomprises at least one hydroxyl reactive group per molecule.

19. A resin-reactive modifier according to claim 17 whichis selected from the group consisting of butadiene polymerand hydrogenated butadiene polymer comprising at least onehydroxyl reactive group per molecule.

* * * * *