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WO 2013/148295 A2 3 October 2013 (03.10.2013) P O P CT

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WO 2013/148295 A2 3 October 2013 (03.10.2013) P O P CT (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date WO 2013/148295 A2 3 October 2013 (03.10.2013) P O P CT (51) International Patent Classification: AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, D06M 15/19 (2006.01) BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, (21) International Application Number: HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, PCT/US20 13/03 1830 KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, (22) International Filing Date: ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, 15 March 2013 (15.03.2013) NO, NZ, OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, (25) Filing Language: English TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, (26) Publication Language: English ZM, ZW. (30) Priority Data: (84) Designated States (unless otherwise indicated, for every 61/618,166 30 March 2012 (30.03.2012) US kind of regional protection available): ARIPO (BW, GH, GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, SZ, TZ, (71) Applicant: CELANESE INTERNATIONAL CORPOR¬ UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, TJ, ATION [US/US]; 222 W. Las Colinas Blvd., Irving, Texas TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, 75039 (US). EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, (72) Inventors: LUNSFORD, David; 12 Heritage Drive, Foun TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, tain Inn, South Carolina 29644 (US). FARWAHA, Ra- ML, MR, NE, SN, TD, TG). jeev; 26 Boice Lane, Belle Mead, New Jersey 08502 (US). SCHOOTS, Harrie; 1924 Lauren Lake Drive, League Declarations under Rule 4.17 : City, Texas 77573 (US). — of inventorship (Rule 4.17(iv)) (74) Agent: ROBERTS, Peter; Roberts Mlotkowski Safran & Published: Cole, P.C., Suite 500, 7918 Jones Branch Drive, McLean, Virginia 22102 (US). — without international search report and to be republished upon receipt of that report (Rule 48.2(g)) (81) Designated States (unless otherwise indicated, for every kind of national protection available): AE, AG, AL, AM, < ∞ (54) Title: DISPERSE DYEING OF TEXTILE FIBERS (57) Abstract: In a process for dyeing textile fibers, a plurality of textile fibers are contacted with a polymer dispersed in a non- aqueous carrier liquid so as to deposit the polymer and the carrier on the fibers. The carrier liquid is then removed from the fibers to leave a coating of the polymer on the fibers and thereby form polymer- treated fibers. The polymer-treated fibers are then contacted with a disperse dye material under conditions effective to bond the disperse dye material to the polymer coating, whereby the poly - S mer coating serves to affix the disperse dye material to the textile fibers. DISPERSE DYEING OF TEXTILE FIBERS Field [0001] The present development relates to the dyeing of textile fibers, particularly cellulosic fibers and especially cotton fibers, with disperse dyes. Background [0002] As a matter of past practice, cotton fibers in the form of yarns and fabrics have generally been dyed with reactive, direct, sulfur, vat, indigo or mordant dyes. Currently the industry prefers reactive dyeing for apparel as reactive dyes provide the brightest colored cotton of all the dyes. Water-soluble reactive dyes, which also provide dyeing results with good fastness-to-washing properties, can be used to dye or print hydrophilic cellulose fibers such as cotton fibers. In such procedures, the cellulose fiber -OH groups which are accessible on the fiber surface react with the fiber- reactive groups of the reactive dyes, forming a covalent fiber/dye bond. [0003] Direct or substantive dyes are used in a neutral or slightly alkaline dye bath with the addition of sodium chloride or sodium sulfate. Vat dyes such as indigo are essentially insoluble in water. Reduction in alkaline liquor produces the water soluble alkali metal salt of a vat dye, which salt has an affinity for textile fibers such as cotton. Both direct and vat dyes provide for dull shades which limits their ability to expand into all cotton dyeing applications. [0004] Dyeing of cotton with reactive dyes gives good color fastness. However, reactive dyes are strongly hydrophilic leading to dye wastage and process inefficiencies and high costs due to the necessity of using long dyeing times with salt additions and alkali, thus allowing for the sensitive needs of reactives for high pH and high temperature conditions. Reactive dyes which do not react with cotton cellulose in the dyeing step eventually react with water and hydrolyze. This hydrolyzed dye must be removed from the cotton surface after dyeing with an after-soaping step to improve crockfastness and washfastness properties. Reactive dyes are also currently under scrutiny as possibly being cancer-causing agents. [0005] Another dye class commonly employed for the coloring of textiles comprises disperse dyes. Disperse dyes were originally developed for the dyeing of cellulose acetate and are water-insoluble. Disperse dyes are finely ground in the presence of a dispersing agent. The main use of disperse dyes is for the dyeing of polyester, but they can also be used to dye nylon, cellulose acetate and acrylic fibers. Dyeing of polyester with disperse dyes requires a temperature of 130 °C provided through an exhaust (batch) machine capable of high pressure (such as a jet machine) or a continuous process with a stenter frame (See Thermasol process). [0006] Given their lack of affinity or substantivity for cellulose, disperse dyes cannot be readily used to dye cotton fibers and fabrics. However, some attempts have been made to provide procedures for dyeing modified cotton fibers, e.g., fabrics, with disperse dyes. For example, U.S. Patent Publication No. 2006/0048308 discloses a method of dyeing or printing cellulose-containing fiber materials using disperse dyes. Such a method comprises pre-treating the cellulose fiber material with a water-soluble or dispersible polyester resin and a water-soluble or dispersible acrylic binder. The polyester resin is fixed, for example, to cotton fabric with the acrylic binder and strong cross-linkers (e.g., melamine) via a pretreatment bath. The polyester impregnated fabric is then dyed with an aqueous dye bath containing disperse dye at a temperature of 130 °C under elevated pressure conditions. However, the high levels of resin binder required in this process adversely affects the softness of the dyed fabric. [0007] Notwithstanding the foregoing procedures for dyeing hydrophilic fibers and fabrics using reactive, direct, vat or water-insoluble disperse dyes, it would be advantageous to provide additional techniques for dyeing cotton and other cellulosic fibers and fabrics using disperse dyes under relatively mild dyeing conditions to produce full package dyed cotton fabrics and garments which have especially desirable softness, color fastness and light fastness and which also have a tendency for shorter post dyeing finishing treatment process times. Such finished dyed cotton fibers and fabrics would then be especially useful for preparation of textured, high-end garments such as those produced by further fabric and garment treatment such as stone-washing. Summary [0008] In one aspect, the present development is directed to a process for dyeing textile fibers, the process comprising: A) contacting a plurality of textile fibers with a polymer dispersed in a non aqueous carrier liquid so as to deposit the polymer and the carrier on the fibers; B) removing the carrier liquid from the fibers to leave a coating of the polymer on the fibers and thereby form polymer- treated fibers; and C) contacting the polymer-treated fibers with a disperse dye material under conditions effective to bond the disperse dye material to the polymer coating, whereby the polymer coating serves to affix the disperse dye material to the textile fibers. [0009] Conveniently, the textile fibers comprise natural fibers, preferably cellulosic fibers, more preferably cotton fibers, optionally together with synthetic fibers. [0010] Typically, the polymer is selected from polyurethanes, polyesters, epoxy resins, vinyl ester-based, acrylic-based, styrene/acrylic -based and styrene/butadiene- based polymers. [0011] Typically the carrier liquid is selected from alcohols, aliphatic and aromatic hydrocarbons, and halogenated derivatives thereof. Detailed Description [0012] The present development is directed to the dyeing of textile fibers in the form of a yarn, fabric or garment, using a polymer binder which directly bonds to the fibers and to a disperse dye material so as to affix the dye to the fibers. In this way, even when the fibers are formed mostly or totally of a cellulosic material, such as cotton, a wash fast and light fast dyed product can be produced without sacrificing the softness of the underlying fibers.: Textile Fibers [0013] The term "textile fibers" is used herein to individual staple fibers or filaments (continuous fibers), yarns, fabrics, and articles (e.g., garments). Yarns may include, for instance, multiple staple fibers that are twisted together ("spun yarn"), filaments laid together without twist ("zero-twist yarn"), filaments laid together with a degree of twist, and a single filament with or without twist ("monofilament"). The yarn may or may not be texturized. Suitable fabrics may likewise include, for instance, woven fabrics, knit fabrics, and non-woven fabrics. Garments may be apparel and industrial garments. The terms "fabrics" and "textiles" also include home goods such as linens, drapery, and upholstery (automotive, boating, airline included) made of the cotton fibrous materials described herein.
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