EP2094889A2 - Verfahren zur herstellung von fasern - Google Patents

Verfahren zur herstellung von fasern

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Publication number
EP2094889A2
EP2094889A2 EP07822669A EP07822669A EP2094889A2 EP 2094889 A2 EP2094889 A2 EP 2094889A2 EP 07822669 A EP07822669 A EP 07822669A EP 07822669 A EP07822669 A EP 07822669A EP 2094889 A2 EP2094889 A2 EP 2094889A2
Authority
EP
European Patent Office
Prior art keywords
methyl
polyurethane
ethyl
solution
fiber
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Withdrawn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
EP07822669A
Other languages
German (de)
English (en)
French (fr)
Inventor
Markus SCHÜTTE
Hauke Malz
Laszlo Szarvas
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.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Priority to EP07822669A priority Critical patent/EP2094889A2/de
Publication of EP2094889A2 publication Critical patent/EP2094889A2/de
Withdrawn legal-status Critical Current

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Classifications

    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
    • D01F6/58—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products
    • D01F6/70—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polyurethanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
    • C08J3/09—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids
    • C08J3/091—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids characterised by the chemical constitution of the organic liquid
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
    • C08J2375/04—Polyurethanes

Definitions

  • the present invention relates to processes for the production of fibers, preferably spandex fibers, preferably by the wet-spinning process, wherein a solution (I) containing polyurethane is spun into a coagulation bath, wherein as solution (I) polyurethane dissolved in ionic liquid starts. Furthermore, the invention relates to fibers obtainable in this way, preferably spandex fibers. In addition, the invention relates to methods for dissolving polyurethane and mixtures containing ionic liquid and polyurethane dissolved therein. Furthermore, the invention relates to the recycling of spandex fibers and antistatic spandex fibers containing ionic liquid.
  • Elastic fibers made of polyurethane have been known for more than 20 years under the name Spandex. These fibers are made from a polyol, most often a polytetrahydrofuran, MDI and a chain extender, e.g. As ethylenediamine, propylenediamine or mixtures thereof. Spandex fibers are mainly produced by the wet-spinning process or the dry-spinning process. Both production methods are generally known to the person skilled in the art and variously described. Usually, elastic fibers are produced in a titer range from 10 dtex to 3000 dtex.
  • a polyurethane prepolymer of polyol and MDI is usually reacted with the chain extender in solution.
  • the solution is then spun into a liquid coagulation bath.
  • the solidification then takes place by coagulation due to phase separation.
  • the non-solvent and the solvent should be chosen so that they are miscible with each other over the entire concentration range.
  • Currently used in the art z. B. the liquid pair DMF / water, d. H. that a polyurethane-containing DMF solution is spun into a water bath.
  • the product of this process is commonly referred to as wet-spun spandex.
  • a polyurethane prepolymer of polyol and MDI is reacted with the chain extender in solution.
  • a solvent used z. DMF or DMAC.
  • the solution is spun into a hot gas. The gas temperature is higher than the boiling point of the solvent. During the spinning process, the solvent evaporates and the fiber solidifies.
  • the object of the present invention was therefore to develop a process for the production of fibers in which toxicologically harmless as possible, easy and economically manageable starting materials, in particular solvents can be used.
  • the process should enable the recycling of non-specification fibers.
  • the process should be as simple and economical as possible.
  • the preparation of the solution (I) according to the invention can preferably be carried out in such a way that the polyurethane is prepared in the ionic liquid.
  • the polyurethane is prepared in the ionic liquid.
  • This prepolymer may then preferably be reacted, preferably spun, with amines generally known for this purpose, preferably aliphatic diamines, in particular ethylenediamine and / or propylenediamine, to give the spandex fibers.
  • the prepolymer can then preferably with generally known for this purpose amines, preferably aliphatic Diamines, especially ethylenediamine and / or propylenediamine are converted to spandex fibers, preferably spun.
  • amines preferably aliphatic Diamines, especially ethylenediamine and / or propylenediamine are converted to spandex fibers, preferably spun.
  • spandex preferably spandex fibers in the ionic liquid.
  • solution (I) can be produced by dissolving polyurethane, preferably thermoplastic polyurethane, in ionic liquids.
  • the polyurethane that is dissolved in the ionic liquid can thus be any polyurethane that is dissolved in the ionic liquid.
  • chain extenders preferably with amines, more preferably aliphatic diamines, in particular ethylenediamine and / or propylenediamine,
  • spandex preferably spandex fibers or else
  • thermoplastic polyurethane thermoplastic polyurethane
  • auxiliaries (e) can be added to the mixture of prepolymer and ionic liquid.
  • polyurethane is therefore understood to mean in particular a polymer which is prepared from an (a) isocyanate, (b) isocyanate-reactive compounds and chain extender (c).
  • the weight ratio of polyurethane and ionic liquid in the solution (I) can be selected in a wide range, and is determined mainly by processing properties such as viscosity.
  • the ratio of ionic liquid to polyurethane is usually between 20: 1 and 1:10, preferably between 10: 1 and 1: 1, particularly preferably between 4: 1 and 2: 1.
  • polyurethane by reacting (a) isocyanates with (b) isocyanate-reactive compounds, preferably having a number average molecular weight of 500 to 10,000 g / mol, (c) chain extenders having a molecular weight of 50 to 499 g / mol, optionally in The presence of (d) catalysts and / or (e) adjuvants is well known and widely described to one skilled in the art.
  • wet spun spandex is characterized in that the solution (I) is spun in a coagulation bath.
  • organic isocyanates it is possible to use generally known aliphatic, cycloaliphatic, araliphatic and / or aromatic isocyanates, preferably diisocyanates, for example tri-, tetra-, penta-, hexa-, hepta- and / or octamethylene diisocyanate, 2 -Methyl-pentamethylene-diisocyanate-1, 5, 2-ethyl-butylene-diisocyanate-1, 4, pentamethylene-diisocyanate-1, 5, butylene-diisocyanate-1, 4, 1-isocyanato-3,3,5 trimethyl-5-isocyanatomethylcyclohexane (isophorone diisocyanate, IPDI), 1,4- and / or 1,3-bis (isocyanatomethyl) cyclohexane (HXDI), 1,4-cyclohexane diisocyanate, 1-methyl-2, 4-
  • isocyanate-reactive compounds (b) it is possible to use the generally known isocyanate-reactive compounds, for example polyesterols, polyetherols and / or polycarbonatediols, which are also commonly grouped under the term "polyols", with molecular weights between 500 and 4000 g / mol, preferably between 1000 and 3000 g / mol, in particular between 1500 and 2000 g / mol and preferably an average functionality between 1, 8 and 2.3, preferably 1, 9 to 2.2, in particular 2.
  • polyesterols polyetherols and / or polycarbonatediols
  • polyols polyols
  • polytetrahydrofurans having a molecular weight between 1000 g / mol and 3000 g / mol, preferably between 1700 g / mol and 2200 g / mol.
  • chain extenders (c) it is possible to use generally known aliphatic, araliphatic, aromatic and / or cycloaliphatic compounds having a molecular weight of 50 to 499, preferably 2-functional compounds, for example diamines and / or alkanediols having 2 to 10 carbon atoms in the alkylene radical, in particular especially butanediol-1, 4, hexanediol-1, 6 and / or di-, tri-, tetra-, penta-, hexa-, hepta-, octa-, nona- and / or decaalkylene with 3 to 8 carbon atoms, preferably corresponding Oligo- and / or polypropylene glycols, wherein mixtures of the Ketten tenvermiller can be used.
  • Particularly preferred chain extenders are aliphatic diamines, in particular ethylenediamine or propylenediamine, or mixtures comprising ethylenediamine and prop
  • Suitable catalysts (d) which in particular accelerate the reaction between the NCO groups of the diisocyanates (a) and the hydroxyl and / or amino groups of the constituent components (b) and (c) are known from the prior art customary tertiary amines, such as.
  • triethylamine dimethylcyclohexylamine, N-methylmorpholine, N, N'-dimethylpiperazine, 2- (dimethylaminoethoxy) ethanol, diazabicyclo- (2,2,2) octane and the like and in particular organic metal compounds such as titanic acid esters, iron compounds such , For example, iron (I M) - acetylacetonate, Zinnver- compounds, z.
  • tin diacetate As tin diacetate, tin dioctoate, tin dilaurate or Zinndialkylsalze aliphatic carboxylic acids such as dibutyltin diacetate, dibutyltin dilaurate or the like.
  • the catalysts are usually used in amounts of 0.0001 to 0.1 parts by weight per 100 parts by weight of polyhydroxyl compound (b).
  • Additives and / or additives (s) are added. Examples include blowing agents, surface-active substances, fillers, flame retardants, nucleating agents, oxidation stabilizers, lubricants and mold release agents, dyes and pigments, optionally in addition to the Stabilisatorengemi- invention further stabilizers, eg. As against hydrolysis, light, heat or discoloration, inorganic and / or organic fillers, reinforcing agents and plasticizers.
  • component (e) also includes hydrolysis protectants such as, for example, polymeric and low molecular weight carbodiimides.
  • the polyurethane may contain a phosphorus compound.
  • organophosphorus compounds of the trivalent phosphorus such as phosphites and phosphonites
  • suitable phosphorus compounds are triphenylphosphite, diphenylalkylphosphite, phenyldialkylphosphite, tris (nonylphenyl) phosphite, trilaurylphosphite, trioctadecylphosphite, di-stearyl-pentaerythritol diphosphite, tris (2,4-di-tert-butylphenyl) phosphite, diisodecylpentaerythritol diphosphite, di- (2,4-di-tert-butylphenyl) pentaerythritol diphosphite, tristearyl sorbitol triphosphite, tetrakis (2,4-d
  • chain regulators usually having a molecular weight of from 31 to 499.
  • Such chain regulators are compounds which only have a counterpart have isocyanate-reactive functional group, such as.
  • monofunctional alcohols monofunctional amines and / or monofunctional polyols.
  • chain regulators can generally be used in an amount of 0 to 5, preferably 0.1 to 1, parts by weight, based on 100 parts by weight of component b), and fall by definition under component (c).
  • the polyurethane is preferably based on the reaction of (a) isocyanate, preferably 4,4'-MDI, with (b) isocyanate-reactive compounds having a molecular weight between 500 g / mol and 10,000 g / mol, and (c) chain extenders are preferably preferred a molecular weight between 50 and 499 g / mol, preferably aliphatic diamines, more preferably ethylenediamine and / or propylenediamine, if appropriate in the presence of (d) catalysts and / or (e) auxiliaries.
  • the structural components (b) and (c) can be varied in relatively wide molar ratios.
  • Molar ratios of component (b) to total chain extenders (c) to be used have proven to be from 10: 1 to 1:10, in particular from 1: 1 to 1: 4, the hardness of the polyurethanes increasing with increasing content of (c) increases.
  • the reaction can be carried out under customary ratios, preferably from 900 to 1100, more preferably from 950 to 1050.
  • the ratio is defined by the ratio of the total of the isocyanate groups used in the reaction of component (a) to the opposite Isocyanate-reactive groups, d. H. the active hydrogens, components (b) and (c).
  • an isocyanate group of component (a) has an active hydrogen atom, i. H. an isocyanate-reactive function, the components (b) and (c).
  • more isocyanate groups exist than OH groups.
  • Ionic liquids are well known and widely described.
  • the term "ionic liquids" preferably means compounds, preferably organic compounds, which contain at least one cation and at least one anion, and where at least one cation and / or at least one anion contains an organic radical.
  • the ionic liquids have a melting point of less than 180 0 C.
  • the melting point in a range of -50 0 C to 150 0 C, in particular in the range of - 20 0 C to 120 0 C, particularly preferably below 100 0 C.
  • Ionic liquids in the context of the present invention are preferably salts of the general formula
  • n 1, 2, 3 or 4
  • [A] + is a quaternary ammonium cation, an oxonium cation, a sulfonium cation or a phosphonium cation
  • [Y] n 'is a is a bi-, tri- or tetravalent anion, or
  • Compounds suitable for forming the cation [A] + of ionic liquids are e.g. B. from DE 102 02 838 A1.
  • such compounds can be erstoff-, phosphorus, sulfur or in particular nitrogen atoms, for example at least one nitrogen atom, preferably 1-10 nitrogen atoms, more preferably 1-5, most preferably 1-3 and especially 1-2 nitrogen atoms.
  • further heteroatoms such as oxygen, sulfur or phosphorus atoms may be included.
  • the nitrogen atom is a suitable carrier of the positive charge in the cation of the ionic liquid from which, in equilibrium, a proton or an alkyl radical can then be transferred to the anion to produce an electrically neutral molecule.
  • a cation can first be generated by quaternization on the nitrogen atom of, for example, an amine or nitrogen heterocycle.
  • the quaternization can be carried out by alkylation of the nitrogen atom.
  • salts with different anions are obtained.
  • this can be done in a further synthesis step.
  • the halide can be reacted with a Lewis acid to form a complex anion from halide and Lewis acid.
  • replacement of a halide ion with the desired anion is possible. This can be done by adding a metal salt to precipitate the metal halide formed, via an ion exchanger, or by displacing the halide ion with a strong acid (to release the hydrohalic acid). Suitable methods are, for example, in Angew. Chem. 2000, 112, p. 3926-3945 and the literature cited therein.
  • Suitable alkyl radicals with which the nitrogen atom in the amines or nitrogen heterocycles can be quaternized are C 1 -C 6 -alkyl, preferably C 1 -C 10 -alkyl, particularly preferably C 1 -C 6 -alkyl and very particularly preferably methyl.
  • the alkyl group may be unsubstituted or have one or more identical or different substituents.
  • those compounds which contain at least one five- to six-membered heterocycle in particular a five-membered heterocycle, which has at least one nitrogen atom and optionally an oxygen or sulfur atom; particularly preferred are those compounds which contain at least one five- to six-membered heterocycle containing one, two or three nitrogen atoms and a sulfur or an oxygen atom, most preferably those having two nitrogen atoms.
  • aromatic heterocycles are particularly preferred.
  • Particularly preferred compounds are those which have a molecular weight below 1000 g / mol, very particularly preferably below 500 g / mol. Furthermore, preference is given to those cations which are selected from the compounds of the formulas (IVa) to (IVw)
  • R is hydrogen, a carbon-containing organic, saturated or unsaturated, acyclic or cyclic, aliphatic, aromatic or araliphatic, unsubstituted or interrupted by 1 to 5 heteroatoms or suitable functional groups radical or 1 to 20 carbon atoms;
  • radicals R 1 to R 9 independently of one another are hydrogen, a sulfo group or a carbon-containing organic, saturated or unsaturated, acyclic or cyclic, aliphatic, aromatic or araliphatic, unsubstituted or interrupted by 1 to 5 heteroatoms or suitable functional groups Radical having 1 to 20 carbon atoms, where the radicals R 1 to R 9 , which in the abovementioned formulas (IV) are bonded to a carbon atom (and not to a heteroatom), may additionally be halogen or a functional group; or
  • the carbon-containing group contains heteroatoms, oxygen, nitrogen, sulfur, phosphorus and silicon are preferable.
  • the radicals R 1 to R 9 are, in the cases in which those in the above formulas (IV) to a carbon atom (and not to a heteroatom) bound also be bound directly via the heteroatom.
  • Suitable functional groups are in principle all functional groups which may be bonded to a carbon atom or a heteroatom. Suitable examples include -NR 2 ', and -CN (cyano). Functional groups and heteroatoms may also be directly adjacent, so that combinations of several adjacent atoms, such as -O- (ether), -S- (thioether), -COO- (ester), or -CONR'- ( tertiary amide), are included, for example, di- (Ci-C4-alkyl) amino, d- C4-alkyloxycarbonyl or Ci-C4-alkyloxy.
  • the radicals R ' are the remaining part of the carbon-containing radical.
  • Halogens are fluorine, chlorine, bromine and iodine.
  • the radical R preferably stands for
  • Ci-Cis-alkyl having a total of 1 to 20 carbon atoms, such as methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2- Butyl, 2-methyl-1-propyl (isobutyl), 2-methyl-2-propyl (tert-butyl), 1-pentyl, 2-pentyl, 3-pentyl, 2-methyl-1-butyl, 3-methyl 1-butyl, 2-methyl-2-butyl, 3-methyl-2-butyl, 2,2-dimethyl-1-propyl, 1-hexyl, 2-hexyl, 3-hexyl, 2-methyl-1-pentyl , 3-
  • Glycols, butylene glycols and their oligomers having from 1 to 100 units and a terminal C 1 -C 6 -alkyl, such as, for example, R A O- (CHR B -CH 2 -O) n -CHR B -CH 2 - or R A O- ( CH 2 CH 2 CH 2 CH 2 O) n -CH 2 CH 2 CH 2 CH 2 O- with R A and R B preferably methyl or ethyl and n preferably 0 to 3, in particular 3-oxabutyl, 3-oxapentyl, 3, 6-dioxaheptyl, 3,6-dioxaoctyl, 3,6,9-trioxadecyl, 3,6,9-trioxaundecyl, 3,6,9,12-tetraoxatridecyl and 3,6,9,12-tetraoxatetradecyl;
  • N-di-C 1 -C 6 -alkyl-amino such as N, N-dimethylamino and N, N-diethylamino.
  • the radical R particularly preferably represents unbranched and unsubstituted C 1 -C 18 -alkyl, such as, for example, methyl, ethyl, 1-propyl, 1-butyl, 1-pentyl, 1-hexyl, 1-heptyl, 1-octyl, 1-decyl, 1-dodecyl, 1-tetradecyl, 1-hexadecyl, 1-octadecyl, especially for methyl, ethyl, 1-butyl and 1-octyl and for CH 3 O- (CH 2 CH 2 O) n -CH 2 CH 2 - and CH 3 CH 2 O- (CH 2 CH 2 O) n -CH 2 CH 2 - where n is 0 to 3.
  • C 1 -C 18 -alkyl such as, for example, methyl, ethyl, 1-propyl, 1-butyl, 1-pentyl, 1-hexyl, 1-heptyl, 1-
  • radicals R 1 to R 9 are preferably each independently
  • C6-Ci2-aryl substituted by suitable functional groups, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatoms and / or heterocycles;
  • an unsaturated, saturated or aromatic optionally substituted by suitable functional groups, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatoms and / or heterocycles and optionally substituted by one or more oxygen and / or sulfur atoms and / or one or more substituted or unsubstituted imino groups interrupted ring.
  • Ci-cis-alkyl is preferably methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2 Butyl, 2-methyl-1-propyl (isobutyl), 2-methyl-2-propyl (tert-butyl), 1-pentyl, 2-pentyl, 3-pentyl, 2-methyl-1-butyl, 3 Methyl-1-butyl, 2-methyl-2-butyl, 3-methyl-2-butyl, 2,2-dimethyl-1-propyl, 1-hexyl, 2-hexyl, 3-hexyl, 2-methyl-1 pentyl, 3-methyl-1-pentyl, 4-methyl-1-pentyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl, 4-methyl-2-pentyl, 2-methyl-3-pentyl, 3-
  • aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatoms and / or heterocycles C6-Ci2-aryl is preferably phenyl, ToIyI, XyIyI, ⁇ -naphthyl, ß-naphthyl, 4th -Diphenylyl, chlorophenyl, dichlorophenyl, trichlorophenyl, difluorophenyl, methylphenyl, dimethylphenyl, trimethylphenyl, ethylphenyl, diethylphenyl, isopropylphenyl, tert-butylphenyl, dodecylphenyl, methoxyphenyl, dimethoxyphenyl, ethoxyphenyl, hexyloxyphenyl, methylnaphthyl, isopropylnaphthyl, Chloron
  • C 5 -C 12 -cycloalkyl which is optionally substituted by suitable functional groups, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatoms and / or heterocycles is preferably cyclopentyl, cyclohexyl, cyclooctyl, cyclododecyl, methylcyclopentyl, dimethylcyclopentyl, methylcyclohexyl , Dimethylcyclohexyl, diethylcyclohexyl, butylcyclohexyl, methoxycyclohexyl, dimethoxycyclohexyl, diethoxycyclohexyl, butylthiocyclohexyl, chlorocyclohexyl, dichlorocyclohexyl, dichlorocyclopentyl, Cn F2 ( n ) - (ib) H2a-b with n ⁇ 30, 0 ⁇ a ⁇
  • C5-Ci2-cycloalkenyl is preferably 3-cyclopentenyl, 2-cyclohexenyl, 3-cyclohexenyl, 2.5 - cyclohexadienyl or C n F2 (n-a) -3 (ib) H2a-3b where n ⁇ n 30, 0 ⁇ a ⁇ b and 0 or 1st
  • An optionally substituted by suitable functional groups, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatoms and / or heterocycles substituted five- to six-membered, oxygen, nitrogen and / or sulfur-containing heterocycle is preferably furyl, thiophenyl , Pyrryl, pyridyl, indolyl, benzoxazolyl, dioxolyl, dioxyl, benzimidazolyl, benzthiazolyl, dimethyl pyridyl, methylquinolyl, dimethylpyrryl, methoxyfuryl, dimethoxypyridyl or difluoropyridyl.
  • Two adjacent radicals together form an unsaturated, saturated or aromatic, optionally substituted by suitable functional groups, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatoms and / or heterocycles and optionally by one or more oxygen and / or sulfur atoms and / or or a plurality of substituted or unsubstituted imino groups interrupted ring, it is preferably 1, 3-propylene, 1, 4-butylene, 1, 5-pentylene, 2-oxa-1, 3-propylene, 1-oxa-1, 3 -propylene, 2-oxa-1, 3-propylene, 1-oxa-1,3-propenylene, 3-oxa-1, 5-pentylene, 1-aza-1, 3-propenylene, 1-Ci-C4-alkyl 1-aza-1, 3-propenylene, 1, 4-buta-1, 3-dienylene, 1-aza-1, 4-buta-1, 3-dienylene or 2-aza-1, 4-buta-1 3-dienylene.
  • radicals contain oxygen and / or sulfur atoms and / or substituted or unsubstituted imino groups
  • the number of oxygen and / or sulfur atoms and / or imino groups is not restricted. As a rule, it is not more than 5 in the radical, preferably not more than 4, and very particularly preferably not more than 3.
  • radicals R 1 to R 9 are each independently
  • Ci-Cis-alkyl having a total of 1 to 20 carbon atoms, such as methyl, ethyl, 1-propyl, 2- Propyl, 1-butyl, 2-butyl, 2-methyl-1-propyl (isobutyl), 2-methyl-2-propyl (tert-butyl), 1-pentyl, 2-pentyl, 3-pentyl, 2-methyl 1-butyl, 3-methyl-1-butyl, 2-methyl-2-butyl, 3-methyl-2-butyl, 2,2-dimethyl-1-propyl, 1-hexyl, 2-hexyl, 3
  • Glycols, butylene glycols and their oligomers having 1 to 100 units and a terminal Cr to Cs-alkyl such as R A O- (CH R B -CH 2 -O) n-CH R B -CH 2 - or R A O - (CH 2 CH 2 CH 2 CH 2 O) n -CH 2 CH 2 CH 2 CH 2 O-
  • R A and R B are preferably methyl or ethyl and n is preferably 0 to 3, in particular 3-oxabutyl, 3-oxapentyl, 3,6-
  • N, N-di-C 1 -C 6 -alkylamino such as, for example, N, N-dimethylamino and N, N-diethylamino,
  • the radicals R 1 to R 9 are each independently hydrogen or Ci-Cis-alkyl, such as methyl, ethyl, 1-butyl, 1-pentyl, 1-hexyl, 1-heptyl, 1-octyl, phenyl , for 2-cyanoethyl, for 2- (methoxycarbonyl) ethyl, for 2- (ethoxycarbonyl) ethyl, for 2- (n-butoxycarbonyl) ethyl, for N, N-dimethylamino, for N, N- Diethylamino, for chlorine and for CH 3 O- (CH 2 CH 2 O) n -CH 2 CH 2 - and CH 3 CH 2 O- (CH 2 CH 2 O) n -CH 2 CH 2 - with n equal to O to 3,
  • R 1 to R 5 is methyl, ethyl or chlorine and the remaining R 1 to R 5 are hydrogen;
  • R 3 is dimethylamino and the remaining radicals R 1 , R 2 , R 4 and R 5 are hydrogen;
  • R 1 and R 2 or R 2 and R 3 is 1, 4-buta-1, 3-dienylene and the remaining R 1 , R 2 , R 4 and R 5 are hydrogen;
  • R 1 to R 5 are hydrogen;
  • one of the radicals R 1 to R 5 is methyl or ethyl and the remaining radicals R 1 to R 5 are hydrogen.
  • Very particularly preferred pyridinium ions (IVa) include 1-methylpyridinium, 1-ethylpyridinium, 1- (1-butyl) pyridinium, 1- (1-hexyl) pyridinium, 1- (1-octyl) pyridinium, 1 - (1-Hexyl) -pyridinium, 1- (1-octyl) -pyridinium, 1- (1-dodecyl) -pyridinium, 1- (1-tetradecyl) -pyridinium, 1- (1-hexadecyl) -pyridinium, 1 , 2-Dimethylpyridinium, 1-ethyl-2-methylpyridinium, 1- (1-butyl) -2-methylpyridinium, 1- (1-hexyl) -2-methylpyridinium, 1- (1-octyl) -2-methylpyridinium, 1 - (1-Dodecyl) -2-methylpyridinium
  • Very particularly preferred pyridazinium ions (IVb) are those in which R 1 to R 4 are hydrogen; or
  • one of the radicals R 1 to R 4 is methyl or ethyl and the remaining radicals R 1 to R 4 are hydrogen.
  • R 1 is hydrogen, methyl or ethyl and R 2 to R 4 are independently hydrogen or methyl; or
  • R 1 is hydrogen, methyl or ethyl
  • R 2 and R 4 are methyl and R 3 is hydrogen.
  • R 1 is hydrogen, methyl or ethyl and R 2 to R 4 are independently hydrogen or methyl;
  • R 1 is hydrogen, methyl or ethyl, R 2 and R 4 are methyl and R 3 is hydrogen;
  • R 1 to R 4 are methyl
  • R 1 to R 4 are hydrogen.
  • R 1 is hydrogen, methyl, ethyl, 1-propyl, 1-butyl, 1-pentyl, 1-hexyl, 1-octyl or 2-cyanoethyl and R 2 to R 4 are independently hydrogen, methyl or ethyl.
  • imidazolium ions which may be mentioned are 1-methylimidazolium, 1-ethylimidazolium, 1- (1-butyl) -imidazolium, 1- (1-octyl) -imidazolium, 1- (1-dodecyl) - imidazolium, 1- (1-tetradecyl) -imidazolium, 1- (1-hexadecyl) -imidazolium, 1,3-dimethylimidazolium, 1-ethyl-3-methylimidazolium, 1- (1-butyl) -3-methylimidazolium, 1 - (1-Butyl) -3-ethylimidazolium, 1- (1-hexyl) -3-methylimidazolium, 1- (1-hexyl) -3-ethylimidazolium, 1- (1-hexyl) -3-ethylimidazolium, 1- (1-hexyl) -3-
  • R 1 is hydrogen, methyl or ethyl and R 2 to R 4 are independently hydrogen or methyl.
  • R 1 to R 4 are independently hydrogen or methyl.
  • R 1 to R 6 are hydrogen or methyl.
  • R 1 is hydrogen, methyl, ethyl or phenyl and R 2 to R 6 are independently hydrogen or methyl.
  • R 1 and R 2 are independently hydrogen, methyl, ethyl or phenyl and R 3 to R 6 are independently hydrogen or methyl.
  • Very particularly preferred imidazolinium ions are those in which R 1 and R 2 are independently hydrogen, methyl, ethyl, 1-butyl or phenyl, R 3 and R 4 are independently hydrogen, methyl or ethyl and R 5 and R 6 are independently hydrogen or methyl.
  • R 1 and R 2 are independently hydrogen, methyl or ethyl and R 3 to R 6 are independently hydrogen or methyl.
  • Imidazoliniumionen (IVn) or
  • R 1 to R 3 are independently hydrogen, methyl or ethyl and R 4 to R 6 are independently hydrogen or methyl.
  • R 1 is hydrogen, methyl, ethyl or phenyl and R 2 and R 3 are independently hydrogen or methyl.
  • R 1 and R 2 are independently hydrogen, methyl, ethyl or phenyl and R 3 is hydrogen, methyl or phenyl.
  • R 1 is hydrogen, methyl or ethyl and R 2 and R 3 are independently hydrogen or methyl, or R 2 and R 3 together are 1, 4-buta-1,3-dienylene.
  • R 1 is hydrogen, methyl, ethyl or phenyl and R 2 to R 9 are independently of one another hydrogen or methyl.
  • IVt imidazolidinium ions
  • R 1 and R 4 are independently hydrogen, methyl, ethyl or phenyl and R 2 and R 3 and R 5 to R 8 are independently hydrogen or methyl.
  • R 1 to R 3 are independently d- to cis-alkyl
  • R 1 and R 2 together are 1, 5-pentylene or 3-oxa-1, 5-pentylene and R 3 is C 1 -C 18 alkyl or 2-cyanoethyl.
  • ammonium ions may be mentioned methyl tri (1-butyl) -ammonium, N, N-dimethylpiperidinium and N, N-dimethylmorpholinium.
  • Examples of the tertiary amines of which the quaternary ammonium ions of the general formula (IVu) are derived by quaternization with the abovementioned radicals R are diethyl-n-butylamine, diethyl-tert-butylamine, diethyl-n-pentylamine, diethyl-hexyl amine, diethyloctylamine, diethyl (2-ethylhexyl) amine, di-n-propylbutylamine, di-n-propyl-n-pentylamine, di-n-propylhexylamine, di-n-propyloctylamine, di-n-propyl (2 ethylhexyl) amine, di-isopropylethylamine, di-isopropyl-n-propylamine, di-isopropyl-butylamine, diisopropylpentylamine, di
  • Preferred quaternary ammonium salts of the general formula (IVu) are those which can be derived from the following tertiary amines by quaternization with the abovementioned radicals R, such as diisopropylethylamine, diethyl-tert-butylamine, di-iso-propylbutylamine, di -n-butyl-n-pentylamine, N, N-di-n-butylcyclohexylamine and tertiary amines of pentyl isomers.
  • Particularly preferred tertiary amines are di-n-butyl-n-pentylamine and tertiary amines of pentyl isomers.
  • Another preferred tertiary amine having three identical residues is triallylamine.
  • R 1 to R 5 are methyl.
  • guanidinium ion may be mentioned N, N, N ', N', N ", N" - hexamethylguanidinium.
  • R 1 and R 2 are independently methyl, ethyl, 1-butyl or 1-octyl and R 3 is methyl or ethyl, 2 ;
  • R 1 is methyl, ethyl, 1-butyl or 1-octyl
  • R 2 is a -CH 2 -CH 2 -OR 4 group and R 3 and R 4 are independently methyl or ethyl; or
  • R 1 is a -CH 2 -CH 2 -OR 4 group
  • R 2 is a -CH 2 -CH 2 -OR 5 group
  • R 3 to R 5 are independently methyl or ethyl.
  • Particularly preferred cholinium ions are those in which R 3 is selected from methyl, ethyl, 5-methoxy-3-oxa-pentyl, 8-methoxy-3,6-dioxa-octyl, 1 1-methoxy-3,6 , 9-trioxa-undecyl, 7-methoxy-4-oxa-heptyl, 1-methoxy-4,8-dioxa-undecyl, 15-methoxy-4,8,12-trioxa-pentadecyl, 9-methoxy-5- oxa-nonyl, 14-methoxy-5,10-oxotetradecyl, 5-ethoxy-3-oxa-pentyl, 8-ethoxy-3,6-dioxa-octyl, 1-ethoxy-3,6,9-trioxa - undecyl, 7-ethoxy-4-oxa-hepty
  • R 1 to R 3 independently of one another are C 1 -C 6 -alkyl, in particular butyl, isobutyl, 1-hexyl or 1-octyl.
  • the pyridinium ions, pyrazolinium, pyrazolium ions and imidazolinium and imidazolium ions are preferable. Furthermore, ammonium ions are preferred.
  • the anion [Y] n "of the ionic liquid is for example selected from
  • silicates and silicic acid esters of the general formula: SiO 4 4 -, HSiO 4 3 -, H 2 SiO 4 2 -, H 3 SiO 4 -, R 3 SiO 4 3 " , R 3 R b Si0 4 2" , R 3 R b R c Si0 4 -, HR 3 SiO 4 2 " ,
  • R 3 , R b , R c and R d are each independently hydrogen, C 3 -C 30 -alkyl, optionally interrupted by one or more non-adjacent oxygen and / or sulfur atoms and / or one or more substituted imino groups 2 -Ci8-alkyl, C6-C 4 aryl, C5-Ci2-cycloalkyl or a five- to six-membered, oxygen-, nitrogen- and / or sulfur-comprising heterocycle, where two of them together form an unsaturated, saturated or aromatic, optionally interrupted by one or more oxygen and / or sulfur atoms and / or one or more unsubstituted or substituted imino groups interrupted ring, said radicals each additionally by suitable functional groups, aryl, alkyl, aryloxy, alkoxy, halogen, heteroatoms and / or heterocycles may be substituted.
  • radicals can be used together, for example, as fused building block 1, 3-propylene, 1,4-butylene, 2-oxa-1,3-propylene, 1-oxa-1,3-propylene, 2 -Oxa-1, 3-propenylene, 1-aza-1, 3-propenylene, 1-Ci-C4-alkyl-1-aza-1, 3-propenylene, 1, 4-buta-1, 3-dienylene, 1 -Aza-1, 4-buta-1, 3-dienylene or 2-aza-1, 4-buta-1, 3-dienylene mean.
  • the number of non-adjacent oxygen and / or sulfur atoms and / or imino groups is basically not limited, or is automatically limited by the size of the remainder or the ring building block. As a rule, it is not more than 5 in the respective radical, preferably not more than 4 or very particularly preferably not more than 3. Furthermore, at least one, preferably at least two, carbon atoms (e) are generally present between two heteroatoms.
  • Substituted and unsubstituted imino groups may be, for example, imino, methylimino, iso-propylimino, n-butylimino or tert-butylimino.
  • the term "functional groups" is to be understood as meaning, for example, the following: di (C 1 -C 4 -alkyl) amino, C 1 -C 4 -alkyloxycarbonyl, cyano or C 1 -C 4 -alkoxy, where C 1 to C 4 -alkyl is methyl, ethyl , Propyl, isopropyl, n-butyl, sec-butyl or tert-butyl.
  • C6-C4-aryl substituted by suitable functional groups are, for example, phenyl, ToIyI, XyIyI, ⁇ -naphthyl, ⁇ -naphthyl, 4-diphenylyl, chlorophenyl, dichloro phenyl, trichlorophenyl, difluorophenyl, methylphenyl, dimethylphenyl, trimethylphenyl, ethylphenyl, diethylphenyl, isopropylphenyl, tert-butylphenyl, dodecylphenyl, methoxyphenyl, dimethoxyphenyl, ethoxyphenyl, hexyloxyphenyl, methylnaphthyl, isopropylphenyl, chloronaphthyl
  • C5-C12-cycloalkyl which is substituted by suitable functional groups, aryl, alkyl, aryloxy, halogen, heteroatoms and / or heterocycles are, for example, cyclopentyl, cyclohexyl, cyclooctyl, cyclododecyl, methylcyclopentyl, dimethylcyclopentyl, methylcyclohexyl, dimethylcyclohexyl, diethylcyclohexyl, butylcyclohexyl, methoxycyclohexyl , Dimethoxycyclohexyl, diethoxycyclohexyl, butylthiocyclohexyl, chlorocyclohexyl, dichlorocyclohexyl, dichlorocyclopentyl and a saturated or unsaturated bicyclic system such as norbornyl or norbornenyl.
  • a five- to six-membered, oxygen, nitrogen and / or sulfur-containing heterocycle is, for example, furyl, thiophenyl, pyryl, pyridyl, indolyl, benzoxazolyl, dioxolyl, dioxyl, benzimidazolyl, benzthiazolyl, dimethylpyridyl, methylquinol, dimethylpyryl , Methoxyfuryl, dimethoxypyridyl, difluoropyridyl, methylthiophenyl, isopropylthiophenyl or tert-butylthiophenyl.
  • the ionic liquids used are preferably 1-ethyl-3-methylimidazolium chloride, 1-ethyl-3-methylimidazolium methanesulfonate, 1-butyl-3-methylimidazolium chloride, 1-butyl-3-methylimidazolium methanesulfonate, methyltri-n- butylammonium methylsulfate, 1, 2,4-trimethylpyrazolium methylsulfate, 1-ethyl-2,3-dimethylimidazolium ethylsulfate, 1,2,3-trimethylimidazolium methylsulfate, methylimidazolium chlorides, methylimidazolium bisulfate, 1-ethyl-3 methylimidazolium hydrogen sulfate, 1-ethyl-3-methylimidazolium tetrachloroaluminate, 1-butyl-3-methylimidazolium hydrogensulfate, 1-butyl
  • 1-ethyl-3-methylimidazolium methanesulfonate 1-ethyl-2,3-di-methylimidazolium ethylsulfate, 1-ethyl-3-methylimidazolium diethylphosphat and / or 1-ethyl-3-methylimidazolium chloride.
  • the spinning of the solution (I) containing the polyurethane dissolved in ionic liquid can be carried out by generally customary and known processes, in particular the wet-spun process.
  • the solution (I) is passed through a nozzle, stretched and passed into a coagulation bath, in which the fiber is formed by coagulation. By stretching, the fiber receives the desired titer.
  • the solution (I) at temperatures between 40 0 C and 140 0 C, preferably between 60 0 C and 100 0 C, in particular between 70 0 C and 90 0 C spun.
  • the solution (I) has a viscosity (spinning viscosity) of between 0.1 Pa * s and 1000 Pa * s, preferably between 1 Pa * s and 100 Pa * s.
  • the fiber By spinning the solution (I) into a coagulation bath, the fiber is obtained.
  • the coagulation bath contains a non-solvent which coagulates the polyurethane in solution (I), preferably water.
  • a non-solvent which coagulates the polyurethane in solution (I)
  • water preferably water
  • a mixture (II) of various non-solvents it is also possible to use a mixture (II) of various non-solvents.
  • the mixture (II) preferably contains water.
  • the mixture contains an ionic liquid.
  • the weight ratio of water to ionic liquid in the mixture (II) can be set in a wide range. The ratio is determined by the coagulation properties of water in the mixture and the ability to separate from the ionic liquid after exiting the coagulation bath.
  • the maximum concentration of ionic liquid in water in the mixture (II) depends on the coagulation properties of water in the ionic liquid.
  • the minimum concentration of ionic liquid in water depends on the separation possibilities of water and ionic liquid. The minimum possible concentration of ionic liquid in water is 0% by weight.
  • the preferred spinning speed is between 1 and 1000 m / min, more preferably between 3 and 200 m / min, in particular between 3 and 100 m / min.
  • spin finishes prevent z. B. the bonding of the fibers on the coil.
  • spin finishes are silicone oils.
  • the present invention also relates to the available fibers, preferably spandex fibers.
  • the fibers preferably the spandex fibers
  • the fibers usually still contain a residual content of ionic liquids.
  • residual contents of ionic liquids in the fiber of less than 10 wt .-%, preferably less than 5 wt .-%, particularly preferably less than 3 wt .-%, each based on the total weight of the fiber containing the ionic liquid .
  • no adverse properties can be detected for the fibers.
  • the fibers often have antistatic properties. This prevents the fibers from charging during further processing.
  • the present invention thus also antistatic spandex fibers containing ionic liquid.
  • fibers containing ionic liquid wherein the content of ionic liquid in the fiber is preferably less than 10 wt .-%, based on the total weight of the fiber containing the ionic liquid.
  • the fibers preferably have a hardness between 60 Shore A and 95 Shore A. Also preferred are spandex fibers having a hardness of 60 Shore A to 95 Shore A, preferably 65 Shore A to 90 Shore A, in particular 70 Shore A to 80 Shore A.
  • the fibers are preferably produced in a titer range between 10 dtex to 3000 dtex, more preferably 80 dtex to 2000 dtex, in particular 160 dtex to 1500 dtex.
  • Dtex is a measure of the weight of a fiber 10 km long. At a titer of 1 dtex, a fiber 10 km in length weighs 1 g.
  • the solution (I) can also be prepared by dissolving a spandex fiber in an ionic liquid.
  • the procedure is to give the spandex fibers in the ionic liquid and at a temperature between 50 and 150 0 C, preferably 70 and 130 0 C dissolves. It has proved to be advantageous that due to the ionic nature of the ionic liquid spin finishes such as silicone oils are washed off the spandex fiber and can be easily separated from the solution (I).
  • the mixture of substances produced in this way can be spun as described above.
  • the present invention thus also provides processes for dissolving polyurethane, preferably spandex fibers, by dissolving polyurethane, preferably spandex fibers, in ionic liquids.
  • the invention therefore also relates to mixtures comprising ionic liquid and polyurethane dissolved therein, preferably spandex fibers.
  • a prepolymer is prepared by reaction of PTHF 2000 (BASF Aktiengesellschaft) (2000 g), 4,4 'MDI (722.4 g) and 1, 4-butanediol (40 g) with continuous stirring at 75 0 C in 15650 g of 1- Ethyl 3-methylimidazolium methanesulfonate produced. Subsequently, will the prepolymer cooled to 30 0 C. To the solution is now slowly added a mixture of 79.82 g of ethylenediamine and 4.92 g of diethyleneamine in 5000 g of 1-ethyl-3-methylimidazolium methanesulfonate. Subsequently, the mixture is allowed to react until the viscosity of the solution is 5000-5500 mPa s. Thereafter, the solution is spun in water.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Dispersion Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Artificial Filaments (AREA)
  • Spinning Methods And Devices For Manufacturing Artificial Fibers (AREA)
EP07822669A 2006-11-23 2007-11-16 Verfahren zur herstellung von fasern Withdrawn EP2094889A2 (de)

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EP07822669A EP2094889A2 (de) 2006-11-23 2007-11-16 Verfahren zur herstellung von fasern
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EP2242794B1 (de) * 2008-02-11 2014-04-30 Basf Se Verfahren zur herstellung poröser strukturen aus synthetischen polymeren
DE102010028583B4 (de) * 2009-05-11 2015-04-23 Frank Prissok Abbau von Polyurethanen in Gegenwart spezieller ionischer Flüssigkeiten und einem geringen Wasseranteil
US8754184B2 (en) * 2009-11-16 2014-06-17 Chemtura Corporation Accelerated cure of isocyanate terminated prepolymers
US8383026B1 (en) * 2010-10-21 2013-02-26 U.S Department Of Energy Fabrication of fiber supported ionic liquids and methods of use
CN102329408B (zh) * 2011-08-19 2012-10-03 沈阳航空航天大学 一种利用离子液体作为阻燃剂的阻燃硬质聚氨酯泡沫
DE102012216180A1 (de) * 2012-09-12 2014-03-13 Falke Kgaa Beinbekleidungsstück
CN104073912B (zh) * 2014-06-25 2016-08-24 杭州师范大学 含硫离子液体在聚氨酯复合纤维中的应用
US10697112B2 (en) 2016-04-04 2020-06-30 Supreme Corporation Flame retardant composition, flame retardant fiber and fabric formed using the same, and method for their production
JP7094966B2 (ja) * 2017-02-10 2022-07-04 ビーエーエスエフ ソシエタス・ヨーロピア 弾性繊維の製造方法、弾性繊維物品の製造方法、弾性繊維および弾性繊維物品
CN111304770B (zh) * 2020-02-17 2022-07-22 复旦大学 一种透明导电纤维及其制备方法和在织物显示器中的应用
CN114000209B (zh) * 2021-11-19 2023-08-22 郑州中科新兴产业技术研究院 基于离子液体的三聚氰胺纺丝溶液的制备方法及其应用
CN115772717B (zh) * 2022-12-19 2024-08-09 东南大学 一种皮芯结构的电致变色长丝纤维及其制备方法和织物

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DE19805130A1 (de) * 1998-02-09 1999-08-12 Bayer Ag Antistatisch ausgerüstete Polyurethane und Elastan-Fasern
DE19907830A1 (de) * 1999-02-24 2000-08-31 Bayer Ag Verfahren und Vorrichtung zur Herstellung von Elastanfäden aus Recyclingmaterial
JP2005532440A (ja) * 2002-07-05 2005-10-27 デグサ アクチエンゲゼルシャフト ポリマーとイオン性液体とからなるポリマー組成物
US7888412B2 (en) * 2004-03-26 2011-02-15 Board Of Trustees Of The University Of Alabama Polymer dissolution and blend formation in ionic liquids
PT1984438E (pt) * 2006-02-07 2010-05-17 Basf Se Poliuretano antiestático
US8044120B2 (en) * 2006-10-13 2011-10-25 Basf Aktiengesellschaft Ionic liquids for solubilizing polymers

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CN101578402A (zh) 2009-11-11

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