EP1807565A2 - Modification de textiles au moyen de liquides ioniques - Google Patents

Modification de textiles au moyen de liquides ioniques

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Publication number
EP1807565A2
EP1807565A2 EP05815299A EP05815299A EP1807565A2 EP 1807565 A2 EP1807565 A2 EP 1807565A2 EP 05815299 A EP05815299 A EP 05815299A EP 05815299 A EP05815299 A EP 05815299A EP 1807565 A2 EP1807565 A2 EP 1807565A2
Authority
EP
European Patent Office
Prior art keywords
textile
alkyl
process according
fibers
agents
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP05815299A
Other languages
German (de)
English (en)
Inventor
Kenneth Nathan Price
Jiping Wang
Nodie Monroe Washington
Stacie Ellen Hecht
Gregory Scot Miracle
Jeffrey John Scheibel
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Procter and Gamble Co
Original Assignee
Procter and Gamble Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Procter and Gamble Co filed Critical Procter and Gamble Co
Publication of EP1807565A2 publication Critical patent/EP1807565A2/fr
Withdrawn legal-status Critical Current

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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M23/00—Treatment of fibres, threads, yarns, fabrics or fibrous goods made from such materials, characterised by the process
    • D06M23/10—Processes in which the treating agent is dissolved or dispersed in organic solvents; Processes for the recovery of organic solvents thereof
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/445—Use of auxiliary substances before, during or after dyeing or printing
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/90—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dyes dissolved in organic solvents or aqueous emulsions thereof
    • D06P1/92—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dyes dissolved in organic solvents or aqueous emulsions thereof in organic solvents
    • D06P1/928—Solvents other than hydrocarbons
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/20—Treatment influencing the crease behaviour, the wrinkle resistance, the crease recovery or the ironing ease
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/45—Shrinking resistance, anti-felting properties
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/50—Modified hand or grip properties; Softening compositions

Definitions

  • the present invention is directed to processes for modify ing textiles which comprise fibers. More particularly, the invention is directed to such processes which employ ionic liquid-containing compositions.
  • Ionic liquids have been extensively evaluated as environmental- friendly or “green” alternatives to conventional organic solvents for a broad range of organic synthetic applications.
  • Ionic liquids offer some unique characteristics that distinguish them from conventional organic solvents, such as no effective vapor pressure, a broad liquid range, high polarity and charge density, can be either hydrophobic or hydrophilic, and unique solvating properties.
  • ionic liquids include imidazolinium salts, such as butylmethylimidazolinium hexafluorophosphate, also known as B3MXM/PF6.
  • imidazolinium salts such as butylmethylimidazolinium hexafluorophosphate
  • B3MXM/PF6 also known as B3MXM/PF6.
  • Other well known ionic liquids include N-I -ethyl 3-methylimidazolinum chloride aluminum (III) chloride, which is usually referred to as [emim]Cl-AlC13; and N-butyl pyridinium chloride aluminum (III) chloride, which is usually referred to as [Nbupy]Cl-AlC13.
  • ionic liquids have also been used as microbiocides/plant growth regulators, as described in FR 2434156; as antistatic agents, as described in JP10-265674 and U.S. Patent No. 3,282,728; and. as fruit and vegetable produce treating agents, as described in WO 01/19200.
  • Other uses of ionic liquids are disclosed in U.S. Patent No. 6,048,388 as a component of an ink composition; and in J. Am. Chem. Soc, Vol. 124, pp. 4974-4975 (2002), as an agent to dissolve cellulose.
  • the treating process provides improvements to textiles which comprise fibers, and to provide such improvements through the use of ionic liquid-containing compositions. These processes are advantageous in that they allow provision of improved properties to textiles while employing materials recognized as environmentally friendly.
  • the present invention is directed to processes for modifying a textile to improve its performance which comprise the steps of a) contacting a textile comprising fibers with a treating composition comprising an ionic liquid under conditions sufficient to modify at least a portion of the surface of the fibers, thereby providing a performance improvement to treated textile; b) optionally, contacting a textile comprising fibers with a composition comprising a benefit agent; and c) at least partially removing the treating composition from the textile.
  • the surface modification comprises a partial dissolution of at least one outer layer of the fibers and/or crystal structure change in at least surfaces of the fibers.
  • the surface modification can impart improvements to the textile or allow embedding or attachment of a benefit agent in the fibers.
  • a textile which comprises fibers refers to any fiber-containing textile material or product and includes, but is not limited to, loose or free fibers, yarns (including threads), woven textiles, nonwoven textiles, knitted textiles, fabric articles, and the like.
  • Fabric articles include, but are not limited to, garments, components used in the manufacture of garments, carpets, upholstery, and the like.
  • the textile fibers may be formed of any natural (e.g., cellulose), regenerated (e.g., rayon), or synthetic material, or a combination thereof.
  • the textile fibers comprise a cellulosic material.
  • the fibers comprise a synthetic material, for example comprising polyester.
  • the ionic liquid as used herein refers to a salt that has a melting temperature of about 100°C or less, or, in an alternative embodiment, has a melting temperature of about 60 0 C or less, or, in yet another alternative embodiment, has a melting temperature of about 40 0 C or less.
  • the ionic liquids exhibit no discernible melting point (based on DSC analysis) but are "flowable” at a temperature of about 100 0 C or below, or, in another embodiment, are "flowable” at a temperature of from about 20 to about 8O 0 C, i.e., the typical fabric or dish washing temperatures.
  • the term "flowable” means that the ionic liquid exhibits a viscosity of less than about 10,000 mPa-s at the temperatures as specified above.
  • ionic liquid refers to ionic liquids, ionic liquid composites, and mixtures (or cocktails) of ionic liquids.
  • the ionic liquid can comprise an anionic IL component and a cationic IL component. When the ionic liquid is in its liquid form, these components may freely associate with one another (i.e., in a scramble).
  • the term “cocktail of ionic liquids” refers to a mixture of two or more, preferably at least three, different and charged IL components, wherein at least one IL component is cationic and at least one IL component is anionic.
  • ionic liquid composite refers to a mixture of a salt (which can be solid at room temperature) with a proton donor Z (which can be a liquid or a solid) as described in the references immediately above. Upon mixing, these components turn into a liquid at about 100°C or less, and the mixture behaves like an ionic liquid.
  • ionic liquids possess and make them attractive alternatives to conventional solvents include: a) ionic liquids have a broad liquid range; some ionic liquids can be in the liquid form at a temperature as low as -96°C and others can be thermally stable at temperatures up to 200 0 C; this permits effective kinetic control in many organic reactions and processes; b) ionic liquids have no effective vapor pressure, thus, they are easy to handle and they reduce safety concerns where volatility could be an issue; c) ionic liquids are effective solvents for a broad range of organic and inorganic materials due to their high polarity; d) ionic liquids are effective Bronsted/Lewis acids; and e) ionic liquids can be tuned to the specific application/chemistry desired, for example, they can be selectively made to have properties ranging from hydrophilic to hydrophobic. By virtue of their high polarity and charge density, ionic liquids have unique solvating properties, and may be used in a variety of processing environments and conditions
  • Anions suitable for use in the ionic liquids of the present invention include, but are not limited to, the following materials:
  • Alkyl sulfates (AS), alkoxy sulfates and alkyl alkoxy sulfates, wherein the alkyl or alkoxy is linear, branched or mixtures thereof; furthermore, the attachment of the sulfate group to the alkyl chain can be terminal on the alkyl chain (AS), internal on the alkyl chain (SAS) or mixtures thereof: non-limiting examples include linear Cio- C 2 o alkyl sulfates having formula:
  • x + y is an integer of at least 7, preferably at least about 9; x or y can be O, M + is a cation selected from the cations of the ionic liquids as described in detail herein; non-limiting examples of alkoxy sulfate include sulfated derivatives of commercially available alkoxy copolymers, such as Pluronics® (from BASF);
  • Mono- and di- esters of sulfosuccinates include saturated and unsaturated Ci 2-I8 monoester sulfosuccinates, such as lauryl sulfosuccinate available as Mackanate LO- 100® (from The Mclntyre Group); saturated and unsaturated C 6 - Cj 2 diester sulfosuccinates, such as dioctyl ester sulfosuccinate available as Aerosol OT® (from Cytec Industries, Inc.);
  • Alkyl aryl sulfonates non-limiting examples include tosylate, alkyl aryl sulfonates having linear or branched, saturated or unsaturated C 8 -Ci 4 alkyls; alkyl benzene sulfonates (LAS) such as Cn-Ci 8 alkyl benzene sulfonates; sulfonates of benzene, cumene, toluene, xylene, t-butyl benzene, di-isopropyl benzene, or isopropyl benzene; naphthalene sulfonates and C 6-I4 alkyl naphthalene sulfonates, such as Petro® (from Akzo Nobel Surface Chemistry); sulfonates of petroleum, such as Monalube 605® (from Uniqema);
  • Diphenyl ether (bis-phenyl) derivatives Non-limiting examples include Triclosan (2,4,4'-trichloro-2'-hydroxydiphenyl ether) and Diclosan (4,4'-dichloro-2- hydroxydiphenyl ether), both are available as Irgasan® from Ciba Specialty Chemicals;
  • Linear or cyclic carboxylates non-limiting examples include citrate, lactate, tartarate, succinate, alkylene succinate, maleate, gluconate, formate, cinnamate, benzoate, acetate, salicylate, phthalate, aspartate, adipatej, acetyl salicylate, 3 -methyl salicylate, 4-hydroxy isophthalate, dihydroxyfumarate, 1 ,2,4-benzene tricarboxylate, pentanoate and mixtures thereof;
  • Alkyl oxyalkylene carboxylates non-limiting examples include Ci O -Ci 8 alkyl alkoxy carboxylates preferably comprising 1-5 ethoxy units;
  • Alkyl diphenyl oxide monosulfonate non-limiting examples include alkyl diphenyl oxide monosulfonate of the general formula:
  • R 1 is Ci O -C] 8 linear or branched alkyl
  • R 2 and R 3 are independently SO 3 " or H, provided at least one of R 2 or R 3 is not hydrogen
  • R 4 is R 1 or H
  • suitable alkyl diphenyl oxide monosulfonates are available as DOWF AX® from Dow Chemical and as POLY-TERGENT® from OHn Corp.;
  • HSAS Mid-chain branched alkyl sulfates
  • MLAS mid-chain branched alkyl aryl sulfonates
  • MLAS mid-chain branched alkyl polyoxyalkylene sulfates
  • Alpha olefin sulfonates (AOS) and paraffin sulfonates non-limiting examples include Ci 0-22 alpha-olefm sulfonates, available as Bio Terge AS-40® from Stepan Company;
  • Alkyl phosphate esters include C 8-22 alkyl phosphates, available as Emphos CS® and Emphos TS-230® from Alczo Nobel Surface Chemistry LLC;
  • Sarcosinates having the general formula RCON(CH 3 )CH 2 CO 2 " , wherein R is an alkyl from about C 8-20 ; non-limiting examples include ammonium lauroyl sarcosinate, available as Hamposyl AL-30® from Dow Chemicals and sodium oleoyl sarcosinate, available as Hamposyl O® from Dow Chemical;
  • Taurates such as C 8-22 alkyl taurates, available as sodium coco methyl tauride or Geropon TC® from Rhodia, Inc.;
  • Sulfated and sulfonated oils and fatty acids linear or branched, such as those sulfates or sulfonates derived from potassium coconut oil soap available as Norfox 1101® from Norman, Fox & Co. and Potassium oleate from Chemron Corp.;
  • Alkyl phenol ethoxy sulfates and sulfonates such as C 8-I4 alkyl phenol ethoxy sulfates and sulfonates; non-limiting examples include sulfated nonylphenol ethoxylate available as Triton XN-45S® from Dow Chemical;
  • m is an integer from 0 to 4; a is 0 or 1 ; b is 0 or 1 ; g is 0 or 1 ; when b is 0, one of a and g must be 0; Z is selected from O and S; X and X', wtien present, are selected from O, S, and NR 1 ; when either a, b or g is 1 for a radical R-(X) a -(T)b-(X') g - , R for that radical is independently selected from the group consisting of H, C 1 -C 16 linear or branched, substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, alkaryl, aralkyl, and aryl; when a, b and g are all 0 for a radical, R for that radical may be further selected from the group consisting of F, Cl, Br, I, CN, R
  • X and X' may not be S
  • Y is a radical comprising at least 1 but no more than 20 carbon atoms and containing a substituent -X" -H, where XL" is selected from O, S, and N ⁇ (T') b ,-(X"') a ,-R 2 , where a 1 is 0 or 1, b 1 is 0 or 1, and X" 1 , when present, is selected from O, S, and NR 2
  • R 2 is independently selected from the group consisting of H, C]-Ci 6 linear or branched, substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, alkaryl, aralkyl, and aryl
  • T' is SO 2
  • X"' may not be S
  • R 3 is independently selected from the group consisting of
  • Polyamino polycarboxylates non-limiting examples include ethylene ethylene- diamine tetraacetate (EDTA), diamine tetracetates, N-hydroxy ethyl ethylene diamine triacetates, nitrilo-tri-acetates, ethylenediamine tetraproprionates, triethylene tetraamine hexacetates, diethylene triamine pentaacetates, and ethanol diglycines;
  • EDTA ethylene ethylene- diamine tetraacetate
  • diamine tetracetates N-hydroxy ethyl ethylene diamine triacetates
  • nitrilo-tri-acetates ethylenediamine tetraproprionates
  • triethylene tetraamine hexacetates diethylene triamine pentaacetates
  • ethanol diglycines ethanol diglycines
  • Aminopolyphosphonates such as ethylenediamine tetramethylene phosphonate and diethylene triamine pentamethylene-phosphonate;
  • M+ is a cation selected from the cations of the ionic liquids as described herein;
  • Ethoxylated amide sulfates sodium tripolyphosphate (STPP); dihydrogen. phosphate; fluroalkyl sulfonate; bis-(alkylsulfonyl) amine; bis- (fluoroalkylsulfonyl)amide; (fluroalkylsulfonyl)(fluoroalkylcarbonyl)amide; bis(arylsulfonyl)amide; carbonate; tetrafluorborate (BF 4 " ); hexaflurophospliate (PF 6 " );
  • R 1 - CO - O - C 6 H 4 -R 2 wherein R 1 is C 8 -Ci 8 alkyl, C 8 -Ci 8 amino alkyl, or mixtures thereof, and R 2 is sulfonate or carbonate; non-limiting examples such as:
  • Cations suitable for use in the ionic liquids of the present invention include, but are not limited to, the following materials:
  • Non-limiting examples include amine oxide cations containing one C 8-I8 alkyl moiety and 2 moieties selected from the group consisting of Ci -3 alkyl groups and Ci -3 hydroxyalkyl groups; phosphine oxide cations containing one Cio-is alkyl moiety and 2 moieties selected from the group consisting of C L3 alkyl groups and C 1-3 hydroxyalkyl groups; and sulfoxide cations containing one C 1 O -1S alkyl moiety and a moiety selected from the group consisting of C 1-3 alkyl and Ci -3 hydroxyalkyl moieties; in some embodiments, the amine oxide cations have the following formula:
  • R 3 is an C 8-22 alkyl, C 8-22 hydroxyalkyl, C 8-22 alkyl phenyl group, and mixtures thereof;
  • R 4 is an C 2-3 alkylene or C 2-3 hydroxyalkylene group or mixtures thereof;
  • x is from 0 to about 3; and each R 5 is independently an Ci -3 alkyl or Ci -3 hydroxyalkyl group or a polyethylene oxide group containing an average of from about 1 to about 3 ethylene oxide groups; the R 5 groups may be attached to each other, e.g., through an oxygen or nitrogen atom, to form a ring structure;
  • other exemplary amine oxide cations include Ci 0 -Ci 8 , Cio, Ci 0 -Ci 2 , and C I 2 -C H alkyl dimethyl amine oxide cations, and C 8 -Ci 2 alkoxy ethyl dihydroxy ethyl amine oxide cations;
  • R is selected from the group consisting of alkyl groups containing from about 10 to about 22 carbon atoms, preferably from about 12 to about 18 carbon atoms, alkyl aryl and aryl alkyl groups containing a similar number of carbon atoms with a benzene ring treated as equivalent to about 2 carbon atoms, and similar structures interrupted by amido or ether linkages; each R 1 is an alley 1 group containing from 1 to about 3 carbon atoms; and R 2 is an alkylene group containing from 1 to about 6 carbon atoms; non-limiting examples of betaines include dodecyl dimethyl betaine, acetyl dimethyl betaine, dodecyl amidopropyl dimethyl betaine, tetradecyl dimethyl betaine, tetradecyl amidopropyl dimethyl betaine, dodecyl dimethyl ammonium hexanoate; and amidoalkylbetaines which are disclosed in U.S.
  • the cation may be a sulfobetaine, which are disclosed in US Patent 4,687,602;
  • Amphodiacetates such as disodium cocodiacetate, available as Mackam 2C® from Mclntyre;
  • each R substituent is selected from hydrogen; Ci-C 6 alkyl or hydroxyalkyl, preferably methyl, ethyl, propyl, or hydroxyethyl, and more preferably methyl; poly(Ci-C 3 alkoxy), preferably polyethoxy; benzyl; or a mixture thereof; m is 2 or 3; each n is from 1 to about 4; each Y is -0-(O)C-, -C(O)-O-, -NR-C(O)-, or -C(O)- NR-; with the proviso that when Y is -0-(O)C- or -NR-C(O) -, the sum of carbons in each R 1 plus one is Ci 2 -C 22 , preferably Ci 4 -C 2O , with each R 1 being a hydrocarbyl, or substituted hydrocarbyl group
  • each R is independently an alkyl or hydroxyalkyl Ci-C 6 moiety, preferably methyl, ethyl, propyl or hydroxyethyl, and more preferably methyl; each R 1 is independently a linear or branched, saturated or unsaturated C 6 -C 22 alkyl or alkoxy moiety, preferably Ci 4 -C 2 O moiety, but no more than one R 1 being less than about Ci 2 and then the other R 1 is at least about Ci 6 ; or hydrocarbyl or substituted hydrocarbyl moiety, preferably Ci 0 -C 2O alkyl or alkenyl, most preferably C] 2 -Ci 8 alkyl or alkenyl; in one embodiment, the cation is dialkylenedimethyl ammonium, such as dioleyldimethyl ammonium available from Witco Corporation under the tradename Adogen® 472; in another
  • R 1 C(O)- NR- R 2 — N(R) 2 - R 3 — NR- C(O)-R 1 J + wherein R and R are as defined in cation (e) above, R and R are Ci-C 6 alkylene moieties; for example, difatty amido quats are commercially available from Witco under the Varisoft® tradename;
  • C 8-22 quaternary surfactants such as isostearyl ethyl imidonium available in its ethosulfate salt form as Schercoquat IIS® from Scher Chemicals, Inc., quaternium-52 obtainable as Dehyquart SP® from Cognis Corporation, and dicoco dimethyl ammonium available in its chloride salt form as Arquad 2C-75® from Akzo Nobel Surface Chemistry LLC;
  • Alkoxylate quaternary ammoniums as discussed in US 6,136,769;
  • each R and R 1 are as defined in cation (e) above; each R 2 is a Ci-C 6 alkylene group, preferably an ethylene group; and G is an oxygen atom or an -NR- group; for example, the cation 1 -methyl- l-oleylamidoethyl-2-oleylimidazolinium is available commercially from the Witco Corporation under the trade name Varisoft® 3690; in another embodiment, the cation is alkylpyridinium cation having the formula:
  • R 1 is an acyclic aliphatic C 8 -C 22 hydrocarbon group; in another embodiment, the cation is an alkanamide alkylene pyridinium cation having the formula: wherein R 1 is a linear or branched, saturated or unsaturated C 6 -C 22 alkyl or alkoxy moiety, or a hydrocarbyl or substituted hydrocarbyl moiety, and R 2 is a Ci-C 6 alkylene moiety;
  • Cationic anti-microbial agents such as cetyl pyridinium, chlorohexidine and domiphen.
  • Alkylated caffeine cations such as
  • Ri and R 2 are Cl to C12 alkyl or alkylene groups, (q) Alkyl poly amino carboxylates, such as
  • R is C 8 to C 22 alkyl or alkylene groups or is coco, tallow or oleyl; non- limiting examples include Ampholak® 7CX/C, Ampholak® 7TX/C, and Ampholak® XO7/C from Akzo Nobel.
  • the ionic liquids suitable for use herein may have various anionic and cationic combinations.
  • the ionic species can be adjusted and mixed such that properties of the ionic liquids can be customized for specific applications, so as to provide the desired solvating properties, viscosity, melting point, and other properties, as desired.
  • These customized ionic liquids have been referred to as "designer solvents”.
  • the ionic liquids can be present in various compositions suitable for use in the processes disclosed herein in any desired effective amount. Typically, the ionic liquids are present in an amount ranging from about 0.1% to about 100%, preferably from about 1% to about 85%, and more preferably from about 5% to about 75%, by weight of the textile treating composition. In some embodiments, the ionic liquids comprise at least about 50% by weight of the textile treating composition. In further embodiments, the ionic liquids comprise at least about 80% by weight of the textile treating composition, and in yet further embodiments, the ionic liquids comprise at least about 90% by weight of the textile treating composition.
  • ionic liquids are hygroscopic, thus, may contain appreciable amounts of water (referred to herein as the "innate” or “bound” water) ranging from about 0.01% to less than about 50% by weight of the ionic liquid. It should be noted that “free water” may be added in making the treating composition of the present invention.
  • innate water and free water may be added in making the treating composition of the present invention.
  • the textile treating compositions of the present invention may comprise water, regardless of its origin, ranging from about 0.01% to about 50%, preferably from about 1% to about 40%, more preferably from about 5% to about 30% by weight of the composition.
  • the treating compositions may optionally include a co-solvent.
  • co-solvents include, but are not limited to, linear or branched Cl-ClO alcohols, diols, and mixtures thereof.
  • co-solvents such as ethanol, isopropanol, propylene glycol are used in some of the compositions of the present invention.
  • the ionic liquid textile treating composition is substantially free of free water and/or other organic solvents. These compositions will contain less than about 10 weight percent, more specifically less than about 5 weight percent, even more specifically less than about 1 weight percent, free water and/or other organic solvents.
  • the textile treating compositions containing ionic liquids or cocktails of ionic liquids (undiluted with adjuncts, co-solvents or free water) employed herein have viscosities of less than about 2000 mPa-s, preferably less than about 750 mPa-s, as measured at 2O 0 C.
  • the viscosity of undiluted ionic liquids are in the range from about 0.1 to about 500 mPa-s, preferably from about 0.5 to about 400 mPa-s, and more preferably from about 1 to about 300 mPa-s at 20 0 C.
  • the viscosity of textile treating composition containing ILs lowers to less than about 2000 mPa-s, preferably less than about 500 mPa-s, and more preferably less than about 300 mPa-s, when heated to a temperature in the range of about 40 0 C to 60 0 C.
  • the viscosities of the ionic fluids and compositions containing them can be measured on a Brookfield viscometer model number LVD VII+ at 20 0 C, with spindle no. S31 at the appropriate speed to measure materials of different viscosities. Typically, the measurement is done at a speed of 12 rpm to measure products of viscosity greater than about 1000 mPa-s; 30 rpm to measure products with viscosities between about 500 mPa-s to about 1000 mPa-s; and 60 rpm to measure products with viscosities less than about 500 mPa-s.
  • the undiluted state is prepared by storing the ionic liquids or cocktails in a desiccator containing a desiccant (e.g. calcium chloride) at room temperature for at least about 48 hours prior to the viscosity measurement. This equilibration period unifies the amount of innate water in the undiluted samples.
  • a desiccant e.g. calcium chloride
  • the textile comprising fibers is contacted with the composition containing an ionic liquid (which, as noted above, may comprise a mixture or cocktail of ionic liquids) under conditions sufficient to modify surfaces of the fibers and provide, or facilitate provision of, a performance improvement thereto.
  • a performance improvement is any physical property which is improved by the ionic liquid treatment.
  • the textile fibers are in contact with the ionic liquid-containing composition for a sufficient time such that the polarity and/or ionic charges, attributable to presence of IL, may interrupt hydrogen bondings between fibers, thereby crystal structure changes in at least the surfaces of the fibers may result.
  • the textile fibers are contacted by the ionic liquid-containing composition for a sufficient time such that partial dissolution of at least one outer layer of the surfaces of the fibers may result.
  • Dissolution of the surface layer(s) and/or changes in crystal structure can provide various improvements in physical properties of the fibers, including, but not limited to, improvements in one or more of the textile's wrinkle resistance, smoothness, softness, shape retention properties, and the like.
  • modifications obtained according to the present processes can enable embedding and/or attachment of at least one benefit agent in the surfaces of the fibers, for example, by further contacting the textile with a composition comprising a benefit agent, either simultaneously with or subsequent to the contact with the ionic liquid-containing composition.
  • the benefit agent may be present, either as an adjunct or as an ionic liquid active, in the IL-containing composition.
  • the embedded or attached benefit agent is released from the fibers in a controlled manner (e.g., a slow and sustained release over time).
  • the benefit agent can be protected or stabilized by the ionic liquids such that the benefit agent is delivered in a controlled manner (e.g., by triggering factors, such as copious amount of water, pH change, heat).
  • Suitable benefit agents include, but are not limited to, perfumes, dyes, dye fixative agents, sizings, skin conditioning actives, vitamins, enzymes, surfactants, anti-abrasion agents, wrinkle resistant agents, stain resistant agents, water resistant agents, flame retardants, antimicrobial agents, metal bleach catalysts, bleaching agents, fabric softeners, anti-pilling agents, water repellant agents, ultraviolet protection agents, brighteners, mixtures thereof (i.e., of two or more of these types of benefit agents). Additional examples of suitable benefit agents are disclosed in U.S. Patent No. 6,488,943, Beerse et al; U.S. Patent No. 6,548,470, Buzzaccarini et al.; U.S. Patent No.
  • the benefit agents may be included in a textile treating composition in any desired amount.
  • Typical textile treating compositions may contain from about 0.001 to about 20 percent by weight of the benefit agent(s). In more specific embodiments, such compositions may comprise from about 0.01 to about 10 percent by weight, and more specifically, from about 0.1 to about 5 percent by weight, of the benefit agent(s).
  • One skilled in the art will recognize in view of the foregoing therefore that the modification may be conducted to any desired depth in the textile fibers and is not limited to surface modifications.
  • the processes according to the invention may be conducted in any one or combination of continuous, semi-continuous or batch processing techniques.
  • the contacting step may be achieved in a manner known in the art, for example, including, but not limited to, by immersion techniques, or by non-immersion techniques such as spraying, misting, foaming, padding, or the like.
  • the composition is provided in the form of droplets and the textile fibers are contacted using a non- immersion technique.
  • the process may be conducted during textile mill manufacture or processing, for example in a separate treatment step or during a conventional processing step, for example during a treatment such as sizing, desizing, bleaching, scouring, mercerization, dyeing, printing, finishing, coating, combinations thereof, or the like.
  • a treatment such as sizing, desizing, bleaching, scouring, mercerization, dyeing, printing, finishing, coating, combinations thereof, or the like.
  • Exemplary textile mill processes which may be employed are disclosed, for examp Ie, in U.S. Patent Application Publication No. US 2003/0226213; and in "Textile Processing and Properties: Preparation, Dyeing, Finishing and Performance", by Vigo, Elsevier, 1994.
  • the process may be conducted by a consumer on a garme ⁇ t, for example during home laundering or drying, or other in-home textile/garment treating processes.
  • the specific physical conditions under which the contacting is conducted may be varied based on the particular textile fiber to be treated, the treating composition
  • energy may be applied to the textile fibers, either prior to, simultaneous with and/or subsequent to the contact with the ionic liquid-containing composition, in order to facilitate achievement and/or durability of the desired improvement.
  • Energy may be applied in the form of heat and/or radiation, including, but not limited to microwave, infrared, ultrasonic, or combinations thereof, and the like.
  • the contacting step may be conducted under increased pressure, at an ⁇ bient pressure, or under a reduced pressure vacuum.
  • the contact time is at least about one minute. In an alternate embodiment, the contact time is at least about five minutes.
  • the composition is at least partially removed from the textile. In one embodiment, the composition is substantially fully removed, whereby the textile comprises less than about 5 weight percent, more specifically less than about 1 weight percent, and more specifically less than about 0.1 weight percent of the ionic liquid after the removal step.
  • the composition may be removed from the textile by any technique known in the art, including, but not limited to, rinsing with water, pressing, squeezing, padding, centrifugation, vacuum extraction, combinations thereof, and the like.
  • the composition is collected after it is removed from the textile, for example for recycle and reuse in the process.

Landscapes

  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Detergent Compositions (AREA)
  • Chemical Or Physical Treatment Of Fibers (AREA)

Abstract

Procédés permettant de modifier les caractéristiques d'un textile, qui consiste: a) à mettre un textile contenant des fibres en contact avec une composition de traitement contenant un liquide ionique dans des conditions suffisantes pour modifier au moins les surfaces des fibres et améliorer par là même les caractéristiques du textile traité; b) éventuellement à mettre en contact un textile contenant des fibres avec un agent bénéfique; et c) à extraire au moins partiellement la composition de traitement du textile. Dans des modes de réalisation particuliers, la modification de surface consiste en une dissolution partielle d'au moins une couche extérieure des fibres et/ou en un changement de la structure cristalline au moins dans des surfaces des fibres. La modification de surface permet d'apporter des améliorations au textile et d'incruster ou de fixer un agent bénéfique dans les fibres.
EP05815299A 2004-11-01 2005-11-01 Modification de textiles au moyen de liquides ioniques Withdrawn EP1807565A2 (fr)

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US62405304P 2004-11-01 2004-11-01
PCT/US2005/039346 WO2006050300A2 (fr) 2004-11-01 2005-11-01 Modification de textiles au moyen de liquides ioniques

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EP (1) EP1807565A2 (fr)
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WO (1) WO2006050300A2 (fr)

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JP2008516106A (ja) 2008-05-15
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US20060090271A1 (en) 2006-05-04

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