Indian Patents. 260689:SOLUBILITY OF CELLULOSE IN IONIC LIQUIDS WITH ADDITION OF AMINE BASE

Title of Invention	SOLUBILITY OF CELLULOSE IN IONIC LIQUIDS WITH ADDITION OF AMINE BASE
Abstract	The present invention relates to a solution comprising cellulose, an ionic liquid comprising anions and cations as solvent and 6-30% by weight of a nitrogen-comprising base, based on the total weight of the solution, its preparation and also its use for the physical or chemical treatment of cellulose.

Full Text	"as originally filed 99 Solubility of cellulose in ionic liquids with addition of amine base Description The present invention relates to a solution comprising cellulose and an ionic liquid as solvent, a process for preparing it and its use. Cellulose is a very versatile raw material. In the textile industry, cellulose is, for example, the most important constituent of fiber raw materials, in particular of cotton. Cellulose can be used unchanged or after physical or chemical treatment. In the latter two cases, it is advantageous for cellulose to be in preferably completely dissolved form in a solvent. However, cellulose is insoluble in most solvents. Cellulose is soluble as a copper chelate complex in some copper solutions. Regenerated cellulose can be obtained by precipitation of the cellulose. However, such copper solutions are not very suitable as solvents for cellulose in the case of physical or chemical treatment of the cellulose. For this reason, the systems known, inter alia, as ionic liquids in the literature were proposed very early on as solvents for cellulose. Thus, US-A 1,943,176 describes the dissolution of cellulose in benzylpyridinium chloride. As an example of an ionic liquid, benzylpyridinium chloride is a salt which is present in molten form and thus as a liquid at comparatively low temperatures. Ionic liquids are becoming increasingly important as solvents, e.g. for carrying out chemical reactions. Peter Wasserscheidt, Angew. Chem. 2000, 112, 3926-3945, for example, gives an overview of the use of ionic liquids in transition metal catalysis. Ionic liquids which are present in the liquid state even at room temperature are described, for example, by K.N. Marsh et al.. Fluid Phase Equilibria 219 (2004), 93-98, and J.G. Huddleston et al., Green Chemistry 2001, 3, 156-164. DE-A 102 02 838 describes the use of ionic liquids for separating acids from chemical mixtures. Owing to the good solvent capabilities of ionic liquids, their use for the dissolution of cellulose is also proposed in the more recent international patent application WO-A 03/029329. However, it is emphasized there that such a solution comprises cellulose and an ionic liquid as solvent must comprise essentially no nitrogen-comprising bases. Although the characteristics of the cellulose-comprising solution and its preparation described in WO-A 03/029329 have good results, there is a need to provide improved solutions. It is therefore an object of the present invention to provide a solution of dissolved cellulose which displays improved properties. The object is achieved by a solution comprising cellulose, an ionic liquid comprising anions and cations as solvent and from 6 to 30% by weight of a nitrogen-comprising base, based on the total weight of the solution. It has been found that when a nitrogen-comprising base is added in the concentration range indicated, an improvement in the properties of the solution, for example in respect of the dissolution rate of the cellulose, a lower viscosity and a reduction in the melting point of the ionic liquid can be achieved at least partly. The cellulose to be dissolved can originate from, for example, regenerated cellulose, fibrous cellulose, wood fibers, lint, cotton or paper. It is preferred that, in the solution of the present invention, more than 1% by weight of cellulose, based on the total weight of the solution, are completely dissolved. More preferably, more than 3% by weight, particularly preferably more than 5% by weight and in particular at least 7% by weight, based on the total weight of the solution, are completely dissolved. Advantageously, up to 35% by weight of cellulose, based on the total weight of the solution, can be completely dissolved. Furthermore, up to 25% by weight of cellulose, based on the total weight of the solution, can be completely dissolved. Solutions in which up to 15% by weight of cellulose are completely dissolved are especially suitable for particular applications. For the purposes of the present invention, ionic liquids are preferably salts of the general formula where n is 1, 2, 3 or 4, [A]+is a quaternary ammonium cation, an oxonium cation, a sulfonium cation or a phosphonium cation and [Y]+ is a monovalent, divalent, trivalent or tetravalent anion; (B) mixed salts of the general formulae (II) mentioned for [A]+, and [Y]+ is as defined under (A); or (C) mixed salts of the general formulae (III) The ionic liquids preferably have a melting point of less than 180°C. The melting point is more preferably in the range from -50°C to 150°C, still more preferably In the range from -20°C to 120oC and most preferably below 100°C. Compounds which are suitable for forming the cations [A]+ of Ionic liquids are, for example, known from DE 102 02 838 A1. Thus, such compounds can comprise oxygen, phosphorus, sulfur or In particular nitrogen atoms, for example at least one nitrogen atom, preferably 1-10 nitrogen atoms, particularly preferably 1-5 nitrogen atoms, very particularly preferably 1-3 nitrogen atoms and in particular 1-2 nitrogen atoms. If appropriate, further heteroatoms such as oxygen, sulfur or phosphorus atoms can also be comprised. The nitrogen atom Is a suitable carrier of the positive charge In the cation of the ionic liquid, from which a proton or an alkyl radical can then be transferred in equilibrium to the anion so as to produce an electrically neutral molecule. If the nitrogen atom is the carrier of the positive charge in the cation of the Ionic liquid, a cation can firstly be produced by quaternization of the nitrogen atom of, for example, an amine or nitrogen heterocycle in the synthesis of the ionic liquids. The quaternization can be effected by alkylation of the nitrogen atom. Depending on the alkylatlon reagent used, salts having different anions are obtained. In cases in which it Is not possible to form the desired anion directly in the quaternization, this can be effected in a further step of the synthesis. For example, starting from an ammonium hallde, the halide can be reacted with a Lewis acid to form a complex anion from the halide and Lewis acid. As an alternative, it is possible to replace a halide Ion by the desired anion. This can be achieved by addition of a metal salt with precipitation of the metal halide formed, by means of an ion exchanger or by displacement of the halide ion by a strong acid (with liberation of the hydrogen halide). Suitable methods are described, for example, in Angew. Chem. 2000, 112, pp. 3926 - 3945, and the references cited therein. Suitable alkyl radicals by which the nitrogen atom in the amines or nitrogen heterocycles can, for example, be quaternized are C1 - C18-alkyl, preferably C1 - C10-alkyl, particularly preferably C1- C6-alkyI and very particularly preferably methyl. The alkyl group can be unsubstituted or bear one or more identical or different substituents. Preference is given to compounds which comprise at least one five- or six-membered heterocycle, in particular a five-membered heterocycle, which has at least one nitrogen atom and, if appropriate, an oxygen or sulfur atom; particular preference is given to compounds which comprise at least one five- or six-membered heterocycle which has one, two or three nitrogen atoms and a sulfur or oxygen atom, very particularly preferably those having two nitrogen atoms. Preference is also given to aromatic heterocycles. Particularly preferred compounds are ones which have a molecular weight of less than 1000 g/mol, very particularly preferably less than 500 g/mol and in particular less than 250 g/mol. Furthermore, preference is given to cations which are selected from among the compounds of the formulae (IVa) to (IVw), and oligomers comprising these structures. Further suitable cations are compounds of the general formulae (IVx) and (IVy) and oligomers comprising this structure. In the abovementioned formulae (IVa) to (IVy), • the radical R is hydrogen, a carbon-comprising organic, saturated or unsaturated, acyclic or cyclic, aliphatic, aromatic or araliphatic radical which has from 1 to 20 carbon atoms and is unsubstituted or interrupted by from 1 to 5 heteroatoms or functional groups or substituted; and • the radicals R1 to R9 are each, independently of one another, hydrogen, a sulfo group or a carbon-comprising organic, saturated or unsaturated, acyclic or cyclic, aliphatic, aromatic or araliphatic radical which has from 1 to 20 carbon atoms and is unsubstituted or interrupted by from 1 to 5 heteroatoms or functional groups or substituted, with the radicals R1 to R9 which are bound to a carbon atom (and not to a heteroatom) in the abovementioned formulae (IV) also being able to be halogen or a functional group; or two adjacent radicals from the group consisting of R1 to R9 can together also be a divalent, carbon-comprising organic, saturated or unsaturated, acyclic or cyclic, aliphatic, aromatic or araliphatic radical which has from 1 to 30 carbon atoms and is unsubstituted or interrupted by from 1 to 5 heteroatoms or functional groups or substituted. Preferred are cations of formulae (IVb) to (IVy). Halogens may be fluorine, chlorine, bromine and iodine. The radical R is preferably • Ci-Cia-alkyl which may be unbranched or branched and unsubstituted or substituted by one or more hydroxy, halogen, phenyl, cyano, CrCe-alkoxycarbonyl and/or sulfonic acid substituents and has a total of from 1 to 20 carbon atoms, for example 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-l-pentyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl, 4-methyl-2-pentyl, 2-methyl-3-pentyl, 3-methyl-3-pentyl, 2,2-climethyl-1-butyl, 2,3-dimethyl-1-butyl, 3,3-dimethyl-1-butyl, 2-ethyl-1-butyl, 2,3-dimethyl-2-butyl, 3,3-dimethyl-2-butyl, 1-heptyl, 1-octyl, 1-nonyl, 1-decyl, 1-undecyl, 1-dodecyl, 1-tetradecyl, 1-hexadecyl, 1-octadecyl, 2-hydroxyethyl, benzyl, 3-phenylpropyl, 2-cyanoethyl, 2-(methoxycarbonyl)ethyl, 2-(ethoxycarbonyl)ethyl, 2-(n-butoxycarbonyl)ethyl, trifluoromethyl, difluoromethyl, fluoromethyl, pentafluoroethyl, heptafluoropropyl, heptafluoroisopropyl, nonafluorobutyl, nonafluoroisobutyl, undecylfluoropentyl, undecylfluoroisopentyl, 6-hydroxyhexyl and propylsulfonic acid; • glycols, butylene glycols and oligomers thereof having from 1 to 100 units and a preferably from 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; • vinyl; and • N,N-di-C1-C6-alkylamino, for example N,N-dimethylamino and N,N-diethyl- amino. In case the cation is a pyridinium ion of formula (Iva) it is preferred, that R is other than benzyl, allyl, ethyl or ethoxycarbonylmethyl, wherein R1 to R5 is H. The radical R is particularly preferably unbranched and unsubstituted C1-C18-alkyl, for example methyl, ethyl, 1-propyl. 1-butyl, 1-pentyl, 1-hexyl, 1-heptyl, 1-octyl, 1-decyl, The radicals R1 to R9 are preferably, independently of one another, • hydrogen; • halogen; • a functional group; • C1-C18-alkyI which is optionally substituted by functional groups, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatoms and/or heterocycles and/or interrupted by one or more oxygen and/or sulfur atoms and/or one or more substituted or unsubstituted imino groups; • C2-C18-alkenyl which is optionally substituted by functional groups, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatoms and/or heterocycles and/or interrupted by one or more oxygen and/or sulfur atoms and/or one or more substituted or unsubstituted imino groups; • C6-C12-aryl which is optionally substituted by functional groups, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatoms and/or heterocycles; • C5-C12-cycloalkyl which is optionally substituted by functional groups, aryl, alkyl, aryloxy. alkyloxy, halogen, heteroatoms and/or heterocycles; • C5-Ci2-cycloalkenyl which is optionally substituted by functional groups, aryl. alkyl, aryloxy, alkyloxy, halogen, heteroatoms and/or heterocycles; or • a five- or six-membered, oxygen-, nitrogen- and/or sulfur-comprising heterocycle which is optionally substituted by functional groups, aryl, alkyl, aryloxy, alkyloxy. halogen, heteroatoms and/or heterocycles; or two adjacent radicals together form • an unsaturated, saturated or aromatic ring which is optionally substituted by functional groups, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatoms and/or heterocycles and optionally interrupted by one or more oxygen and/or sulfur atoms and/or one or more substituted or unsubstituted imino groups. Ci-Ci8-alkyl which is optionally substituted by functional groups, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatoms and/or heterocycles 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, i 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-methyl-3-pentyl, 2,2-dimethyl-1-butyl, 2,3-dimethyl-1-butyl, 3,3-dimethyl-1-butyl, 2-ethyl-1-butyl, 2,3"dimethyl-2-butyl, 3,3-dimethyl-2-butyl, heptyl, octyl, 2-etylhexyl, 2,4,4-tri- methylpentyl, 1,1,3,3-tetramethylbutyl, 1 -nonyl, 1 -decyl, 1 -undecyl, 1 -dodecyl, 1 -tridecyl, 1 -tetradecyl, 1 -pentadecyl, 1 -hexadecyl, 1 -heptadecyl, 1 -octadecyl, cyclopentylmethyl, 2-cyclopentyiethyl, 3-cyclopenty)propyl, cyclohexylmethyl, 2-cyclohexylethyl, 3-cyclohexylpropyl, benzyl (phenylmethyl), diphenylmethyl (benzhydryl), triphenylmethyl, 1-phenylethyl, 2-phenylethyl, 3-phenylpropyl, a,a-dimethylbenzyl, p-tolylmethyl, 1-(p-butylphenyl)ethyl, p-chlorobenzyl, 2,4- dichlorobenzyl, p-methoxybenzyl, m-ethoxybenzyl, 2-cyanoethyl, 2-cyanopropyl, 2- methoxycarbonylethyl, 2-ethoxycarbonylethyl, 2-butoxycarbonylpropyl, 1,2- di(metho)cycarbonyl)ethyl, methoxy, ethoxy, formyl, 1,3-dioxolan-2-yl, 1,3-dioxan-2-yl, 2-methyl-1,3-dioxolan-2-yl, 4-methyl-1,3-dioxolan-2-yl, 2-hydroxyethyl, 2- hydroxypropyl, 3-hydroxypropyl, 4-hydroxybutyl, 6-hydroxyhexyl, 2aminoethyl, 2- aminopropyl, 3-aminopropyl, 4-aminobutyl, 6-aminohexyl, 2-methylaminoethyl, 2- methylaminopropyl, 3-methylaminopropyl, 4-methylaminobutyl, 6-methylaminohexyl, 2- dimethylaminoethyl, 2-dimethylaminopropyl, 3-dimethylaminopropyl, 4- dimethylaminobutyl, 6-dimethylaminohexyl, 2-hydroxy-2,2-dimethylethyl, 2-phenoxyethyl, 2-phenoxypropyl, 3-phenoxypropyl, 4-phenoxybutyl, 6-phenoxyhexyl, 2-methoxyethyl, 2-methoxypropyl, 3-methoxypropyl, 4-methoxybutyl, 6-methoxyhexyl, 2-ethoxyethyl, 2-ethoxypropyl, 3-ethoxypropyl, 4-ethoxybutyl, 6-ethoxyhexyl, acetyl, CnF2(n-a)+(i-b)H2a+b where n is from 1 to 30, 0 C2-C18-Alkenyl which is optionally substituted by functional groups, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatoms and/or heterocycles and/or interrupted by one or more oxygen and/or sulfur atoms and/or one or more substituted or unsubstituted imino groups is preferably vinyl, 2-propenyl, 3-butenyl, cis-2-butenyl, trans-2-butenyl or CnF2(n-a)-(i-b)H2a-b whsre n S 30, 0 Ce-Cia-Aryl which is optionally substituted by functional groups, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatoms and/or heterocycles is preferably phenyl, tolyl, xylyl, a-naphthyl, 3-naphthyl, 4-diphenylyl, chlorophenyl, dichlorophenyl, trichlorophenyl, difluorophenyl. methylphenyl, dimethylphenyl, trimethylphenyl, ethylphenyl, diethylphenyl, isopropylphenyi, tert-butylphenyl, dodecylphenyl, methoxyphenyl, dimethoxyphenyl, ethoxyphenyl, hexyloxyphenyl, methylnaphthyl, isopropylnaphthyl, chloronaphthyl, ethoxynaphthyl, 2,6-dimethylphenyl, 2,4,6-trlmethylphenyl, 2,6-dimethoxyphenyl, 2,6-dichlorphenyl, 4-bromophenyl, 2-nitrophenyl, 4-nitrophenyl, 2,4-dinitrophenyl, 2,6-dinitrophenyl, 4-dJmethylaminophenyl, 4-acetylphenyl, ethoxyethylphenyl, ethoxymethylphenyl, methylthlophenyl, isopropylthiophenyl or tert-butylthiophenyl or C6F(5.a)Ha where 0 C5-Ci2-Cycloalkyl which is optionally substituted by functional groups, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatoms and/or heterocycles is preferably cyclopentyl, cyclohexyl, cyclooctyl, cyclododecyl, methylcyclopentyl, dimethylcyclopentyl, methylcyclohexyl, dimethylcyclohexyl, diethylcyclohexyl, butylcyclohexyl, methoxycyclohexl, dimethoxycyclohexyl, diethoxycyclohexyl, butylthiocyclohexyl, chlorocyclohexyl, dichlorocyclohexyl, dichlorocyclopentyl, CnF2(n-a)-(i-b)H2aH3 where n C5-C12-Cycloalkenyl which is optionally substituted by functional groups, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatoms and/or heterocycles is preferably 3-cyclopentenyl, 2-cyclohexenyl, 3-cyclohexenyl, 2,5-cycioh6xadienyl or CnF2(n-a)-3(i-b)H2a-3b where n A five- or six-membered, oxygen-, nitrogen- and/or sulfur-comprising heterocycle which is optionally substituted by functional groups, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatoms and/or heterocycles is preferably furyl, thiophenyl, pyrryl, pyridyl, indolyl, benzoxazolyl, dioxolyl, dioxyl, benzimidazolyl, benzthiazolyl, dimethylpyridyl, methylquinolyl, dimethylpyrryl, methoxyfuryl, dimethoxypyridyl or difluoropyridyl. If two adjacent radicals together form an unsaturated, saturated or aromatic ring which Is optionally substituted by functional groups, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatoms and/or heterocycles and optionally interrupted by one or more oxygen and/or sulfur atoms and/or one or more substituted or unsubstltuted imino groups, the two radicals together are 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 -C1-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. If the abovementioned radicals comprise oxygen and/or sulfur atoms and/or substituted or unsubstltuted imino groups, the number of oxygen and/or sulfur atoms and/or imino groups is not subject to any restrictions. In general, there will be no more than 5 in the radical, preferably no more than 4 and very particularly preferably no more than 3. If the abovementioned radicals comprise heteroatoms, there is generally at least one carbon atom, preferably at least two carbon atoms, between any two heteroatoms. The radicals R1 to R9 are particularly preferably, independently of one another, • hydrogen; • unbranched or branched C1-C16-alkyl which is unsubstltuted or substituted by one or more hydroxy, halogen, phenyl, cyano, C1-C6-alkoxycarbonyl and/or sulfonic acid substituents and has a total of from 1 to 20 carbon atoms, for example 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-methyl-3-pentyl, 2,2-dimethyl-1 -butyl, 2,3-dimethyl-1 -butyl, 3,3-dimethyl-1-butyl, 2-ethyl-1-butyl, 2,3-dimethyl-2-butyl, 3,3-dimethyl-2-butyl, 1-heptyl, 1-octyl, 1-nonyl, 1-decyl, 1-undecyl, 1-dodecyl, 1-tetradecyl, 1-hexa-decyl, 1-octadecyl, 2-hydroxyethyl, benzyl, 3-phenylpropyl, 2-cyanoethyl, 2-(methoxycarbonyl)ethyl, 2-(ethoxycarbonyl)ethyl, 2-(n-butoxycarbonyl)ethyl, trifluoromethyl, difluoromethyl, fluoromethyl, pentafluoroethyl, heptafluoropropyl, heptafluoroisopropyl, nonafluorobutyl, nonafluoroisobutyl, undecylfluoropentyl, undecylfiuoroisopentyl, 6-hydroxyhexyl and propylsulfonic acid; • glycols, butylene glycols and oligomers thereof having from 1 to 100 units and a hydrogen atom or a C1-Cs8alkyI group as end group, for example hydrogen, methyl or ethyl and n is preferably from 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; • vinyl; and • N,N-di-Ci-C6-alkylamino, for example N,N-dimethylamino and N,N-diethylamino. The radicals R1 to R9 are very particularly preferably, independently of one another, hydrogen or C1-C19-alkyl, for example methyl, ethyl, 1-butyl, 1-pentyl, 1-hexyl, 1-heptyl, 1-octyl, phenyl, 2-hydroxyethyl, 2-cyanoethyl, 2-(methoxycarbonyl)ethyl, 2"(ethoxycarbonyl)ethyl, 2-(n-butoxycarbonyl)ethyl, N,N-dimethylamino, N,N-diethylamino, chlorine or CH3O-(CH2CH2O)n-CH2CH2- and CH3CH2O-(CH2CH2O)n-CH2CH2- where n is from 0 to 3. Very particularly preferred pyridinium ions (IVa) are those in which • one of the radicals R1 to R5 is methyl, ethyl or chlorine and the remaining radicals R1 to R5 are hydrogen; • R3 is dimethylamino and the remaining radicals R1, R2, R'4 and R5 are hydrogen; • all radicals R1 to R5 are hydrogen; • R2 is carboxy or carboxamide and the remaining radicals R1,R2, R4 and R5 are hydrogen; or • R1 and R2 or R2 and R3 are together 1,4-buta-1,3-dienylene and the remaining radicals R1, R2, R4 and R5 are hydrogen; and, in particular, those in which Very particularly preferred pyridinium ions (IVa) are 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 -tetra- decyl)pyridinium, 1-(1-hexadecyl)pyridinium, 1,2-dimethylpyridinium, 1-ethyl-2-methyl- pyridinium, 1-(1-butyl)-2-methylpyridinium, 1-(1-hexyl)-2-methylpyridinium, 1 -(1 -octyl)-2-methylpyridinium, 1 -(1 -dodecyl)-2-methylpyridinium, 1 -(1 -tetradecyl)-2-methylpyridinium, 1-(1-hexadecyl)-2"methylpyridinium, 1-methyl-2-ethylpyridinium, 1,2-diethylpyridinium, 1 -(1 -butyl)-2"ethylpyridinium, 1 -(1 -hexyl)-2-ethylpyridinium, 1 -(1 -octyl)-2-ethylpyridinium, 1 -(1 "dodecyl)-2-ethylpyridinium, 1 -(1 -tetradecyl)-2-ethyl-pyridinium, 1 -(1 -hexadecyl)"2-ethylpyridinium, 1,2-dimethyl-5-ethylpyridinium, 1,5-di-ethyl-2-methylpyridinium, 1 -(1 -butyl)-2-methyl-3-ethylpyridinium, 1 -(1 -hexyl)-2-methyl-3-ethylpyridinium and 1-(1-octyl)-2-methyl-3-ethylpyridinium, 1-(1-dodecyl)-2-methyl-3-ethylpyridinium, 1-(1-tetradecyl)-2-methyl-3-ethylpyridinium and 1-(1-hexadecyl)-2-methyl"3-ethylpyridinium. Very particularly preferred pyrazinium ions (IVd) are those in which Very particularly preferred imidazolium ions (IVe) are 1 -methylimidazolium, 1 -ethylimidazolium, 1 -(1 -butyl)imidazolium, 1 -(1 -octyl)imidazolium, 1 -(1 -dode-cyl)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-ethyl-imidazolium, 1 -(1 -hexyl)-3-butylimidazolium, 1 -(1 -octyl)-3-methylimidazolium, 1 -(1 -octyl)-3-ethylimidazolium, 1-(1-octyl)"3-butylimidazolium, 1-(1-dodecyl)-3-methyl-imidazolium, 1-(1-dodecyl)-3-ethylimidazolium, 1-(1-dodecyl)-3-butylimidazolium, 1-(1-dodecyl)-3-octylimidazolium, 1 -(1 -tetradecyl)-3-methylimidazolium, 1 -(1 -tetradecyl)-3-ethylimidazolium, 1 -(1 -tetradecyl)-3-butylimidazolium, 1 -(1 -tetradecyl)-3-octylimi-dazolium, 1-(1-hexadecyl)-3-methylimidazolium, 1-(1-hexadecyl)-3-ethylimidazolium, 1-(1 -hexadecyl)-3-butylimidazolium, 1 -(1 -h6xadecyl)-3-octylimidazolium, 1,2-dimethyl-imidazolium, 1,2,3-trimethylimidazolium, 1 -ethyl-2,3-dimethylimidazolium, 1 -(1 -butyl)-2,3-dimethylimidazolium, 1 -(1 -hexyl)-2,3-dlmethylimidazolium, 1 -(1 -octyl)-2,3-di-methyllmidazolium, 1,4-dimethylimidazolium, 1,3,4-trlmethylimidazolium, 1,4-dimethyl-3-ethylimidazolium, 3-butylimidazolium, 1,4-dimethyl-3-octylimidazolium, 1,4,5-tri-methylimidazolium, 1,3,4,5-tetramethylimidazolium, 1,4,5-trimethyl-3-ethylimidazolium, 1,4,5-trimethyl-3-butylimidazolium and 1,4,5-trimethyl"3-octylimidazolium. Very particularly preferred pyrazolium ions (IVf), (IVg) or (IVg') are those in which • R1 is hydrogen, methyl or ethyl and R1 to R4 are each, independently of one another, hydrogen or methyl. Very particularly preferred pyrazolium ions (IVh) are those in which Very particularly preferred 1-pyrazolinium ions (IVi) are those in which Very particularly preferred 2-pyrazolinium ions (IVj) or (IVj') are those in which Very particularly preferred thiazolium Ions (IVo) or (IVo') and oxazolium ions (IVp) are those in which • R1 is hydrogen, methyl, ethyl or phenyl and R2 and R3 are each, independently of one another, hydrogen or methyl. Very particularly preferred 1,2,4-triazolium ions (IVq), (IVq') or (IVq") are those in which • R1 and R2 are each, independently of one another, hydrogen, methyl, ethyl or phenyl and R^ is hydrogen, methyl or phenyl. Very particularly preferred 1,2,3-triazolium ions (IVr), (IVr') or (IVr") are those in which • R1 is hydrogen, methyl or ethyl and R2 and R3 are each, independently of one another, hydrogen or methyl, or R2 and R3 are together 1,4-buta-l ,3-dienylene. Very particularly preferred pyrrolidinium ions (IVs) are those in which • R1 is hydrogen, methyl, ethyl or phenyl and R2 to R9 are each, independently of one another, hydrogen or methyl. Very particularly preferred imidazolidinium ions (IVt) are those in which • R1 and R4 are each, independently of one another, hydrogen, methyl, ethyl or phenyl and R2 and R3 and also R5 to R8 are each, independently of one another, hydrogen or methyl. Very particularly preferred ammonium ions (IVu) are those in which • R1 to R3 are each, independently of one another, C1-C18-alkyI; or • R1 and R2 are together 1,5-pentylene or 3-oxa-1,5-pentylene and R3 is C1-C18-alkyl, 2-hydroxyethyl or 2-cyanoethyL Very particularly preferred ammonium ions (IVu) are methyltri(1-butyl)ammonium, N,N-dimethylpiperidinium and N,N-dimethylmorpholinium. Examples of tertiary amines from which the quaternary ammonium ions of the general formula (IVu) are derived from quaternation by the abovementioned radicals R are diethyl-n-butylamine, diethyi-tert-butylamine, diethyl-n-pentylamine, diethylhexylamine, diethyloctylamine, diethyl(2-ethylhexyl)amine, di-n-propylbutylamine, di-n-propyl-n- pentylamine, di-n-propylhexylamine, di-n-propyloctylamine, di-n-propyl(2-ethyl- hexyl)amine, diisopropylethylamine, diisopropyl-n-propylamine, diisopropylbutylamine, diisopropylpentylamine, diisopropylhexylamine, diisopropyloctylamine, diisopropyl(2- ethylhexyl)amine, di-n-butylethylamine, di-n-butyl-n-propylamine, di-n-butyl-n- pentylamine, di-n-butylhexylamine, di-n-butyloctylamine, di-n-butyl(2-ethylhexyl)amine, N-n-butylpyrrolidine, N-sec-butylpyrrolidine, N-tert-butylpyrrolidine, N-n- pentylpyrrolidine, N,N-dimethylcyclohexylamine, N.N-diethylcyclohexylamine, N,N-di-n-butylcyclohexylamine. N-n-propylpiperidine, N-isopropylpiperidine, N-n-butylpiperidine, N-sec-butylpiperidine, N-tert-butylpiperidine, N-n-pentylpiperidine, N-n-butylmorpholine, N-sec-butylmorpholine, N-tert-butylmorpholine, N-n-pentylmorpholine, N-benzyl-N-ethylaniline, N-benzyl-N-n-propylaniline, N-benzyl-N-isopropylaniline, N-benzyl-N-n-butylaniline, N,N-dimethyl-p-toluidene, N,N-diethyl-p-toluidene, N,N-di-n-butyl-p-toluidene, diethylbenzylamine, dl-n-propylbenzylamine, di-n-butylbenzylamine, diethylphenylamine, di-n-propylphenylamine and di-n-butylphenylamine. Preferred tertiary amines (IVu) are diisopropylethylamine, diethyl-tert-butylamine, diisopropylbutylamine, di-n-butyl-n-pentylamine, N,N-di-n-butylcyclohexylamine and tertiary amines derived from pentyl isomers. Particularly preferred tertiary amines are di-n-butyl-n-pentylamine and tertiary amines derived from pentyl isomers. A further preferred tertiary amine which has three identical radicals is triallylamine. Very particularly preferred guanidinium ions (IVv) are those in which • R1 to R5 are methyl. A very particularly preferred guanidinium ion (IVv) is N,N,N',N',N",N"-hexamethylguanldinium. Very particularly preferred choiinium ions (IVw) are those in which • R1 and R2 are each, independently of one another, methyl, ethyl, 1-butyl or 1-octyl and R3 is hydrogen, methyl, ethyl, acetyl, -SO2OH or-PO(OH)2; • R^ is methyl, ethyl, 1-butyl or 1-octyl, R^ is a -CH2-CH2-OR'^ group and R^ and R' are each, independently of one another, hydrogen, methyl, ethyl, acetyl, -SO2OH or -P0(OH)2; or • R1 I S a -CH2-CH2-OR'4 group, R2 is a -CH2-CH2-OR5 group and R3 to R5 are each, independently of one another, hydrogen, methyl, ethyl, acetyl, -SO2OH or -PO(OH)2. Particularly preferred choiinium ions (IVw) are those in which R3 is selected from among hydrogen, methyl, ethyl, acetyl. 5-methoxy-3"Oxapentyl, 8-methoxy-3,6-dioxaoctyl, 11-methoxy-3,6,9-trioxaundecyl, 7-methoxy-4-oxaheptyl, 11-methoxy-4,8-dioxaundecyl, 15-methoxy-4,8,12-trioxapentadecyl, 9-methoxy-5-oxanonyl, 14-meth-oxy-5,10-oxatetradecyl, 5-ethoxy-3-oxapentyl, 8-ethoxy-3,6-dioxaoctyl, 11 -ethoxy-3,6,9-trioxaundecyl, 7-ethoxy-4-oxaheptyl, 11 -ethoxy-4,8-dioxaundecyl, 15-ethoxy-4,8,12-trioxapentadecyl, 9-ethoxy-5-oxanonyl or 14-ethoxy-5,10-oxatetradecyL Very particularly preferred phosphonium ions (IVx) are those in which • R1 to R3 are each, independently of one another, C1-C18-alkyl, in particular butyl, isobutyl, 1-hexyl or 1-octyL Among the abovementioned heterocyclic cations, the pyridinium ions, pyrazolinium ions, pyrazolium ions and imidazolinium ions and also the imidazolium ions are preferred. Preference is also given to ammonium ions. Very particular preference is given to 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 -hexa-decyOpyridinium, 1,2-dimethylpyridinium, 1 -ethyl-2-methylpyridinium, 1 -(1 -butyl)-2-methylpyridinium, 1-(1-hexyl)-2-methylpyridinium, 1-(1-octyl)-2-methyipyridinium, 1-(1-dodecyl)-2-methylpyridinium, 1-(1 -tetradecyl)-2-methylpyridinium, 1 -(1 -hexadecyl)-2-methylpyridinium, 1-methyl-2-ethylpyridlnium, 1,2-diethylpyridinium, 1-(1-butyl)-2- ethylpyridinium, 1-(1-hexyl)-2-ethylpyridinium, 1"(1-octyl)-2-ethylpyridinium, 1-(1-dode- cyl)-2-ethylpyridinium, 1 -(1 -tetradecyl)-2-ethylpyridinium, 1 -(1 -hexadecyl)-2"ethyl- pyridinium, 1,2-dimethyl-5-ethylpyridinium, 1,5-diethyl-2-methylpyridinium, 1-(1-butyl)- 2-methyl-3-ethylpyridinium, 1 -(1 -hexyl)-2-methyl-3"ethylpyridinium, 1 -(1 -octyl)-2- methyl-3-ethylpyridinium, 1-(1-dodecyl)-2-methyl-3-ethylpyridinium, 1-(1-tetradecyl)-2- methyl-3-ethylpyridinium, 1 -(1 -hexadecyl)-2-methyl"3-ethylpyridinium, 1 -methyl- imidazolium, 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 -hexyl)-3-methylimidazolium, 1 -(1 -octyl)-3-methylimidazolium, 1 -(1 -dodecyl)"3- methylimidazolium, 1 -(1 -tetradecyl)-3-methylimidazolium, 1 -(1 -hexadecyl)- 3-methylimidazolium, 1,2-dimethylimidazolium, 1,2,3-trimethylimidazolium, 1-ethyl-2,3-dimethylimidazolium, 1 -(1 -butyl)-2,3-dimethylimidazolium, 1 -(1 -hexyl)-2,3-dimethyl-imidazolium and 1-(1-octyl)-2,3-dimethylimidazolium, 1,4-dimethylimidazolium, 1,3,4-trimethylimidazolium, 1,4-dimethyl-3-ethylimidazolium, 3-butylimidazolium, 1,4-dimethyl-3-octylimidazolium, 1,4,5-trimethylimidazolium, 1,3,4,5-tetramethylimida-zolium, 1,4,5-trimethyl-3-ethylimidazolium, 1,4,5-trimethyl-3-butylimidazolium and 1,4,5-trimethyl-3-octylimidazolium. • the group of alkoxides and aryloxides of the general formula: RaO"; comprising heterocycle, where two of them may together form an unsaturated, saturated or aromatic ring which is optionally interrupted by one or more oxygen and/or sulfur atoms and/or one or more unsubstituted or substituted imino groups, where the radicals mentioned may each be additionally substituted by functional groups, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatoms and/or heterocycles. Here, Ci-Ci8-alkyl which is optionally substituted by functional groups, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatoms and/or heterocycles is, for example, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, 2-ethylhexyl, 2,4,4-trimethylpentyl, decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, 1,1-dimethylpropyl, 1,1-dimethylbutyl, 1,1,3,3-tetramethylbutyl, benzyl, 1-phenylethyl, a,a-dimethylbenzyl, benzhydryl, p-tolylmethyl, 1-(p-butylphenyl)ethyl, p-chlorobenzyl, 2,4-dichlorobenzyl, p-methoxybenzyl, m-ethoxybenzyl, 2-cyanoethyl, 2-cyanopropyl, 2-methoxycarbonylthyl, 2-ethoxycarbonylethyl, 2-butoxycarbonylpropyl, 1,2-di-(methoxycarbonyl)ethyl, 2-methoxyethyl, 2-ethoxyethyl, 2-butoxyethyl, diethoxymethyl, diethoxyethyl, 1,3-dioxolan-2-yl, 1,3-dioxan-2-yl, 2-methyl-1,3-dioxolan-2-yl, 4-methyl-1,3-dioxolan-2-yl, 2-isopropoxyethyl, 2-butoxypropyl, 2-octyloxyethyl, chloromethyl, trichloromethyl, trifluoromethyl, 1,1-dimethyl-2-chloroethyl, 2-methoxyisopropyl, 2-ethoxyethyl, butylthiomethyl, 2-dodecylthioethyl, 2-phenlythioethyl, 2,2,2-trifluoroethyl, 2-hydroxyethyl, 2-hydroxypropyl, 3-hydroxypropyl, 4-hydroxybutyl, 6-hydroxyhexyl, 2-aminoethyl, 2-aminopropyl, 4-aminobutyl, 6-aminohexyl, 2-methylaminoethyl, 2-methylaminopropyl, 3-methylaminopropyl, 4-methylaminobutyl, 6-methylaminohexyl, 2-dimethylaminoethyl, 2-dimethylaminopropyl, 3-dimethylaminopropyl, 4-dimethyl-aminobutyl, 6-dimethylaminohexyl, 2-hydroxy-2,2-dimethylethyl, 2-phenoxyethyl, 2"phenoxypropyl, 3-phenoxypropyl, 4-phenoxybutyl, 6-phenoxyhexyl, 2-methoxyethyl, 2-methoxypropyl, 3-methoxypropyl, 4-methoxybutyl, 6-methoxyhexyl, 2-ethoxyethyl, 2-ethoxypropyl, 3-ethoxypropyl, 4-ethoxybutyl or 6-ethoxyhexyl, C2-C18-Alkyl which is optionally substituted by one or more nonadjacent oxygen and/or sulfur atoms and/or one or more substituted or unsubstituted imino groups is, for example, 5-hydroxy-3-oxapentyl, 8-hydroxy-3,6-dioxaoctyl, 11-hydroxy-3,6,9-tri-oxaundecyl, 7-hydroxy-4-oxaheptyl, 11-hydroxy-4,8-dioxaundecyl, 15-hydroxy-4,8,12-trioxapentadecyl, 9-hydroxy-5"Oxanonyl, 14-hydroxy-5,10-oxatetradecyl, 5"methoxy-3-oxapentyl, 8-methoxy-3,6-dioxaoctyl, 11 -methoxy-3,6,9-trioxaundecyl, 7-methoxy-4-oxaheptyl, 11-methoxy-4,8"dioxaundecyl, 15-methoxy-4,8,12-trioxapentadecyl, 9-methoxy-5-oxanonyl, 14"methoxy-5,10-oxatetradecyl, 5-ethoxy-3-oxapentyl, S-ethoxy-3,6-dioxaoctyl, 11 -ethoxy-3,6,9-trioxaundecyl, 7-ethoxy-4-oxaheptyl, 11 -ethoxy-4,8-dioxaundecyl, 15-ethoxy-4,8,12-trioxapentadecyl, 9-ethoxy-5-oxanonyl or 14-ethoxy-5,10-oxatetradecyl, If two radicals form a ring, these radicals can together form, for example, 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 -CrC4-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 as fused-on building block. The number of nonadjacent oxygen and/or sulfur atoms and/or imino groups is in principle not subject to any restrictions or is automatically restricted by the size of the radical or the cyclic building block. In general, it will be no more than 5 in the respective radical, preferably no more than 4 and very particularly preferably no more than 3. Furthermore, there is generally at least one carbon atom, preferably at least two carbon atoms, between any two heteroatoms. Substituted and unsubstituted imino groups can be, for example, imino, methylimino, isopropylimino, n-butylimino or tert-butylimino. For the purposes of the present invention, the term "functional groups" refers, for example, to the following: carboxy, carboxamide, hydroxy, di-(C1-C4-alkyl)amino, C1- C4-alkyloxycarbonyl, cyano or Ci-C4-alkoxy. Here, C1-C4-alkyl is methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl or tert-butyl. C6-C14-Aryl which is optionally substituted by functional groups, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatoms and/or heterocycles is, for example, phenyl, tolyl, xylyl, a-naphthyl, p-naphthyl, 4-diphenylyl, chlorophenyl, dichlorophenyl, trichlorophenyl, difluorophenyl, methylphenyl, dimethylphenyl, trimethylphenyl, ethylphenyl, diethylphenyl, isopropylphenyl, tert-butylphenyl, dodecylphenyl, methoxyphenyl, dimethoxyphenyl, ethoxyphenyl, hexyloxyphenyl, methylnaphthyl, isopropylnaphthyl, chloronaphthyi, ethoxynaphthyl, 2,6-dimethylphenyl, 2,4,6-trimethylphenyl, 2,6-dimethoxyphenyl, 2,6-dichlorophenyl, 4-bromophenyl, 2- or 4-nitrophenyl, 2,4- or 2,6-dinitrophenyl, 4-dimethylaminophenyl, 4-acetylphenyl, methoxyethylphenyl or ethoxymethylphenyl. C5-Ci2-Cycloalkyl which is optionally substituted by functional groups, aryl, alkyl, aryloxy, halogen, heteroatoms and/or heterocycles is, for example, cyclopentyl, cyclohexyl, cyclooctyl, cyclododecyl, methylcyclopentyl, dimethylcyclopentyl, methylcyclohexyl, dimethylcyclohexyl, diethylcyclohexyl, butylcyclohexyl, methoxycyclohexyl, dimethoxycyclohexyl, diethoxycyclohexyl, butylthiocyclohexyl, chlorocyclohexyl, dichlorocyclohexyl, dichlorocyclopentyl or a saturated or unsaturated bicyclic system such as norbornyl or norbornenyl. A five- or six-membered, oxygen-, nitrogen- and/or sulfur-comprising heterocycle is, for example, furyl , thiophenyl, pyryl, pyridyl, indolyl, benzoxazolyl, dioxolyl, dioxyl, benzimidazolyl, benzthiazolyl, dimethylpyridyl, methylquinolyl, dimethylpyryl, methoxyfuryl, dimethoxypyridyl, difluoropyridyl, methylthiophenyl, isopropylthiophenyl or tert-butylthiophenyl. Preferred anions are selected from the group of halides and halogen-comprising compounds, the group of carboxylic acids, the group of sulfates, sulfites and sulfonates and the group of phosphates. Preferred anions are chloride, bromide, iodide, SCN", OCN', CN", acetate, C1-C4-alkylsulfates, R1-COO', R1SO3', R1RbPOV, methanesulfonates, tosylate, C1-C4 dialkylphosphates, hydrogen sulfate or tetrachloroaluminate. Particularly preferred anions are CI", CH3COO" or CH3SO3". Both cations and anions are present in the ionic liquid. Within the ionic liquid, a proton or an alkyl radical is transferred from the cation to the anion. This forms two uncharged molecules. There is thus an equilibrium in which anions, cations and the two uncharged molecules formed therefrom are present. The solution preferably has a temperature of not more than 180°C. The solution of the present invention more preferably has a temperature of not more than 160°C, even more preferably not more than 120°C and particularly preferably not more than 100°C. In a preferred embodiment, the proportion of nitrogen-comprising base is 6 - 20% by weight, more preferably 6 - 15% by weight, even more preferably 6 to 14% by weight, even more preferably 6 to 13% by weight, particularly preferably from 6 to 10% by weight, based on the total weight of the solution. Furthermore the proportion is preferably 7 to 14% by weight, especially 8 to 13% by weight. The nitrogen-comprising base is preferably a compound whose nitrogen atom or atoms is/are primary, secondary or tertiary and which is derived from the quaternary compounds of the formulae (IVa) to (IVw), with the radical R forming the quaternary nitrogen not being present and the other substituents having, independently of one another, the abovementioned meanings and also being able, if appropriate, to be hydrogen. The base is preferably derived from the cation present in the ionic liquid, if this is a quaternary nitrogen-comprising compound. However, it is also possible for this not to be the case. Further preferred bases are listed in DE-A 102 02 838 on page 4, line 17, to page 7, line 51, the disclosure of which is hereby fully incorporated by reference. Particularly preferred bases are amines, imidazoles, monoethylamine, isopropylamine, ethylhexylamine, ethanolamine or imidazole. The present invention further provides a process for preparing a solution according to the invention, which comprises the steps addition of cellulose to a solution comprising an ionic liquid comprising anions and cations as solvent and from 6 to 30% by weight of a nitrogen-comprising base, based on the total weight of the solution, and mixing of the solution until the cellulose is completely dissolved. Mixing is preferably carried out by means of stirring, shaking and/or with the aid of microwaves. The dissolution preferably occurs within 3 days, more preferably within one day and particularly preferably within 12 hours. The present invention further provides for the use of a solution according to the present invention for the physical or chemical treatment of cellulose. The chemical treatment can comprise oxidation, reduction, pyrolysis, hydrolysis, isomeration, sterification, alkoxylation or copolymerization. The present invention is illustrated by the following examples. Examples An amount of an ionic liquid and an amine is placed in a reaction vessel at 95°C with stirring and is admixed with an amount of cellulose powder. The mixture is stirred at 95oC until the cellulose has dissolved completely. In addition, the time required for this is determined. The batch sizes and results are summarized in the following table. BMIM = 1-n-butyl-3-methylimidazolium Claims 1. A solution comprising cellulose, an ionic liquid comprising anions and cations as solvent and 6 - 30% by weight of a nitrogen-comprising base, based on the total weight of the solution, wherein the ionic liquid comprises at least one cation of formula (IVe) and oligomers comprising these structures, where • the radical R is hydrogen, a carbon-comprising organic, saturated or unsaturated, acyclic or cyclic, aliphatic, aromatic or araliphatic radical which has from 1 to 20 carbon atoms and is unsubstituted or interrupted by from 1 to 5 heteroatoms or functional groups or substituted; and • the radicals R1 to R9 are each, independently of one another, hydrogen, a sulfo group or a carbon-comprising organic, saturated or unsaturated, acyclic or cyclic, aliphatic, aromatic or araliphatic radical which has from 1 to 20 carbon atoms and is unsubstituted or interrupted by from 1 to 5 heteroatoms or functional groups or substituted, with the radicals R1 to R9 which are bound to a carbon atom (and not to a heteroatom) in the abovementioned formulae (IV) also being able to be halogen or a functional group; or two adjacent radicals from the group consisting of R1 to R9 can together also be a divalent, carbon-comprising organic, saturated or unsaturated, acyclic or cyclic, aliphatic, aromatic or araliphatic radical which has from 1 to 30 carbon atoms and is unsubstituted or interrupted by from 1 to 5 heteroatoms or functional groups or substituted. • the group of alkoxides and aryloxides of the general formula R'O"; • the group of halometalates of the general formula [MqHalr]9--, where M is a metal and Hal is fluorine, chlorine, bromine or iodine, q and r are positive integers and indicate the stoichiometry of the complex and s is a positive integer and indicates the charge on the complex; • the group of sulfides, hydrogen sulfides, polysulfides, hydrogen polysulfides and thiolates of the general formulae: S'-, HS-, [Sv]'-, [HSv]-, [R^S]-. where v is a positive integer from 2 to 10; and nitrogen- and/or sulfur-comprising heterocycle, where two of them may together form an unsaturated, saturated or aromatic ring which is optionally interrupted by one or more oxygen and/or sulfur atoms and/or one or more unsubstituted or substituted imino groups, where the radicals mentioned may each be additionally substituted by functional groups, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatoms and/or heterocycles. 5. The solution according to any of claims 1 to 4 which has a temperature of not more than 180°C. 6. The solution according to any of claims 1 to 5. wherein the proportion of the nitrogen-comprising base is 6 - 20% by weight, based on the total weight of the solution. 7. The solution according to any of claims 1 to 6, wherein the nitrogen-comprising base is a compound whose nitrogen atom or atoms is/are primary, secondary or tertiary and which is derived from the quaternary compounds of the formula (IVe). with the radical R forming the quaternary nitrogen of the quaternary compounds not being present and the other substituents having, independently of one another, the meanings given in claim 1, and also being able, if appropriate, to be hydrogen. 8. A process for preparing a solution according to any of claims 1 to 7, which comprises the steps addition of cellulose to a solution comprising an ionic liquid comprising anions and cations as defined in claim 1 as solvent and from 6 to 30% by weight of a nitrogen-comprising base, based on the total weight of the solution, and mixing of the solution until the cellulose is completely dissolved. 9. Method of using a solution according to any of claims 1 to 7 for the physical or chemical treatment of cellulose. Dated this 15 day of October 2007

Full Text

"as originally filed

99

Solubility of cellulose in ionic liquids with addition of amine base
Description
The present invention relates to a solution comprising cellulose and an ionic liquid as solvent, a process for preparing it and its use.
Cellulose is a very versatile raw material. In the textile industry, cellulose is, for example, the most important constituent of fiber raw materials, in particular of cotton.
Cellulose can be used unchanged or after physical or chemical treatment. In the latter two cases, it is advantageous for cellulose to be in preferably completely dissolved form in a solvent. However, cellulose is insoluble in most solvents.
Cellulose is soluble as a copper chelate complex in some copper solutions. Regenerated cellulose can be obtained by precipitation of the cellulose. However, such copper solutions are not very suitable as solvents for cellulose in the case of physical or chemical treatment of the cellulose.
For this reason, the systems known, inter alia, as ionic liquids in the literature were proposed very early on as solvents for cellulose.
Thus, US-A 1,943,176 describes the dissolution of cellulose in benzylpyridinium chloride.
As an example of an ionic liquid, benzylpyridinium chloride is a salt which is present in molten form and thus as a liquid at comparatively low temperatures.
Ionic liquids are becoming increasingly important as solvents, e.g. for carrying out chemical reactions. Peter Wasserscheidt, Angew. Chem. 2000, 112, 3926-3945, for example, gives an overview of the use of ionic liquids in transition metal catalysis.

Ionic liquids which are present in the liquid state even at room temperature are described, for example, by K.N. Marsh et al.. Fluid Phase Equilibria 219 (2004), 93-98, and J.G. Huddleston et al., Green Chemistry 2001, 3, 156-164.
DE-A 102 02 838 describes the use of ionic liquids for separating acids from chemical mixtures.
Owing to the good solvent capabilities of ionic liquids, their use for the dissolution of cellulose is also proposed in the more recent international patent application WO-A 03/029329. However, it is emphasized there that such a solution comprises cellulose and an ionic liquid as solvent must comprise essentially no nitrogen-comprising bases.
Although the characteristics of the cellulose-comprising solution and its preparation described in WO-A 03/029329 have good results, there is a need to provide improved solutions.
It is therefore an object of the present invention to provide a solution of dissolved cellulose which displays improved properties.
The object is achieved by a solution comprising cellulose, an ionic liquid comprising anions and cations as solvent and from 6 to 30% by weight of a nitrogen-comprising base, based on the total weight of the solution.
It has been found that when a nitrogen-comprising base is added in the concentration range indicated, an improvement in the properties of the solution, for example in respect of the dissolution rate of the cellulose, a lower viscosity and a reduction in the melting point of the ionic liquid can be achieved at least partly.
The cellulose to be dissolved can originate from, for example, regenerated cellulose, fibrous cellulose, wood fibers, lint, cotton or paper.
It is preferred that, in the solution of the present invention, more than 1% by weight of cellulose, based on the total weight of the solution, are completely dissolved. More preferably, more than 3% by weight, particularly preferably more than 5% by weight and in particular at least 7% by weight, based on the total weight of the solution, are completely dissolved.

Advantageously, up to 35% by weight of cellulose, based on the total weight of the solution, can be completely dissolved. Furthermore, up to 25% by weight of cellulose, based on the total weight of the solution, can be completely dissolved. Solutions in which up to 15% by weight of cellulose are completely dissolved are especially suitable for particular applications.
For the purposes of the present invention, ionic liquids are preferably salts of the general formula

where n is 1, 2, 3 or 4, [A]+is a quaternary ammonium cation, an oxonium cation, a sulfonium cation or a phosphonium cation and [Y]+ is a monovalent, divalent, trivalent or tetravalent anion;
(B) mixed salts of the general formulae (II)

mentioned for [A]+, and [Y]+ is as defined under (A); or
(C) mixed salts of the general formulae (III)

The ionic liquids preferably have a melting point of less than 180°C. The melting point is more preferably in the range from -50°C to 150°C, still more preferably In the range from -20°C to 120oC and most preferably below 100°C.
Compounds which are suitable for forming the cations [A]+ of Ionic liquids are, for
example, known from DE 102 02 838 A1. Thus, such compounds can comprise oxygen, phosphorus, sulfur or In particular nitrogen atoms, for example at least one nitrogen atom, preferably 1-10 nitrogen atoms, particularly preferably 1-5 nitrogen atoms, very particularly preferably 1-3 nitrogen atoms and in particular 1-2 nitrogen atoms. If appropriate, further heteroatoms such as oxygen, sulfur or phosphorus atoms can also be comprised. The nitrogen atom Is a suitable carrier of the positive charge In the cation of the ionic liquid, from which a proton or an alkyl radical can then be transferred in equilibrium to the anion so as to produce an electrically neutral molecule.
If the nitrogen atom is the carrier of the positive charge in the cation of the Ionic liquid, a cation can firstly be produced by quaternization of the nitrogen atom of, for example, an amine or nitrogen heterocycle in the synthesis of the ionic liquids. The quaternization can be effected by alkylation of the nitrogen atom. Depending on the alkylatlon reagent used, salts having different anions are obtained. In cases in which it Is not possible to form the desired anion directly in the quaternization, this can be effected in a further step of the synthesis. For example, starting from an ammonium hallde, the halide can be reacted with a Lewis acid to form a complex anion from the halide and Lewis acid. As an alternative, it is possible to replace a halide Ion by the desired anion. This can be achieved by addition of a metal salt with precipitation of the metal halide formed, by means of an ion exchanger or by displacement of the halide ion by a strong acid (with liberation of the hydrogen halide). Suitable methods are described, for example, in Angew. Chem. 2000, 112, pp. 3926 - 3945, and the references cited therein.

Suitable alkyl radicals by which the nitrogen atom in the amines or nitrogen heterocycles can, for example, be quaternized are C1 - C18-alkyl, preferably C1 - C10-alkyl, particularly preferably C1- C6-alkyI and very particularly preferably methyl. The alkyl group can be unsubstituted or bear one or more identical or different substituents.
Preference is given to compounds which comprise at least one five- or six-membered heterocycle, in particular a five-membered heterocycle, which has at least one nitrogen atom and, if appropriate, an oxygen or sulfur atom; particular preference is given to compounds which comprise at least one five- or six-membered heterocycle which has one, two or three nitrogen atoms and a sulfur or oxygen atom, very particularly preferably those having two nitrogen atoms. Preference is also given to aromatic heterocycles.
Particularly preferred compounds are ones which have a molecular weight of less than 1000 g/mol, very particularly preferably less than 500 g/mol and in particular less than 250 g/mol.
Furthermore, preference is given to cations which are selected from among the compounds of the formulae (IVa) to (IVw),

and oligomers comprising these structures.
Further suitable cations are compounds of the general formulae (IVx) and (IVy)

and oligomers comprising this structure.
In the abovementioned formulae (IVa) to (IVy),
• the radical R is hydrogen, a carbon-comprising organic, saturated or
unsaturated, acyclic or cyclic, aliphatic, aromatic or araliphatic radical which has
from 1 to 20 carbon atoms and is unsubstituted or interrupted by from 1 to 5
heteroatoms or functional groups or substituted; and
• the radicals R1 to R9 are each, independently of one another, hydrogen, a sulfo
group or a carbon-comprising organic, saturated or unsaturated, acyclic or
cyclic, aliphatic, aromatic or araliphatic radical which has from 1 to 20 carbon
atoms and is unsubstituted or interrupted by from 1 to 5 heteroatoms or
functional groups or substituted, with the radicals R1 to R9 which are bound to a
carbon atom (and not to a heteroatom) in the abovementioned formulae (IV)
also being able to be halogen or a functional group; or

two adjacent radicals from the group consisting of R1 to R9 can together also be a divalent, carbon-comprising organic, saturated or unsaturated, acyclic or cyclic, aliphatic, aromatic or araliphatic radical which has from 1 to 30 carbon atoms and is unsubstituted or interrupted by from 1 to 5 heteroatoms or functional groups or substituted.
Preferred are cations of formulae (IVb) to (IVy).

Halogens may be fluorine, chlorine, bromine and iodine.
The radical R is preferably
• Ci-Cia-alkyl which may be unbranched or branched and unsubstituted or substituted by one or more hydroxy, halogen, phenyl, cyano, CrCe-alkoxycarbonyl and/or sulfonic acid substituents and has a total of from 1 to 20 carbon atoms, for example 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-l-pentyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl,
4-methyl-2-pentyl, 2-methyl-3-pentyl, 3-methyl-3-pentyl, 2,2-climethyl-1-butyl,
2,3-dimethyl-1-butyl, 3,3-dimethyl-1-butyl, 2-ethyl-1-butyl, 2,3-dimethyl-2-butyl,
3,3-dimethyl-2-butyl, 1-heptyl, 1-octyl, 1-nonyl, 1-decyl, 1-undecyl, 1-dodecyl,
1-tetradecyl, 1-hexadecyl, 1-octadecyl, 2-hydroxyethyl, benzyl, 3-phenylpropyl,
2-cyanoethyl, 2-(methoxycarbonyl)ethyl, 2-(ethoxycarbonyl)ethyl,
2-(n-butoxycarbonyl)ethyl, trifluoromethyl, difluoromethyl, fluoromethyl, pentafluoroethyl, heptafluoropropyl, heptafluoroisopropyl, nonafluorobutyl, nonafluoroisobutyl, undecylfluoropentyl, undecylfluoroisopentyl, 6-hydroxyhexyl and propylsulfonic acid;
• glycols, butylene glycols and oligomers thereof having from 1 to 100 units and a

preferably from 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;
• vinyl; and
• N,N-di-C1-C6-alkylamino, for example N,N-dimethylamino and N,N-diethyl-
amino.
In case the cation is a pyridinium ion of formula (Iva) it is preferred, that R is other than benzyl, allyl, ethyl or ethoxycarbonylmethyl, wherein R1 to R5 is H.
The radical R is particularly preferably unbranched and unsubstituted C1-C18-alkyl, for example methyl, ethyl, 1-propyl. 1-butyl, 1-pentyl, 1-hexyl, 1-heptyl, 1-octyl, 1-decyl,

The radicals R1 to R9 are preferably, independently of one another,
• hydrogen;
• halogen;
• a functional group;

• C1-C18-alkyI which is optionally substituted by functional groups, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatoms and/or heterocycles and/or interrupted by one or more oxygen and/or sulfur atoms and/or one or more substituted or unsubstituted imino groups;
• C2-C18-alkenyl which is optionally substituted by functional groups, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatoms and/or heterocycles and/or interrupted by one or more oxygen and/or sulfur atoms and/or one or more substituted or unsubstituted imino groups;
• C6-C12-aryl which is optionally substituted by functional groups, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatoms and/or heterocycles;
• C5-C12-cycloalkyl which is optionally substituted by functional groups, aryl, alkyl, aryloxy. alkyloxy, halogen, heteroatoms and/or heterocycles;
• C5-Ci2-cycloalkenyl which is optionally substituted by functional groups, aryl. alkyl, aryloxy, alkyloxy, halogen, heteroatoms and/or heterocycles; or
• a five- or six-membered, oxygen-, nitrogen- and/or sulfur-comprising heterocycle which is optionally substituted by functional groups, aryl, alkyl, aryloxy, alkyloxy. halogen, heteroatoms and/or heterocycles; or
two adjacent radicals together form
• an unsaturated, saturated or aromatic ring which is optionally substituted by
functional groups, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatoms and/or
heterocycles and optionally interrupted by one or more oxygen and/or sulfur
atoms and/or one or more substituted or unsubstituted imino groups.
Ci-Ci8-alkyl which is optionally substituted by functional groups, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatoms and/or heterocycles 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, i 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-methyl-3-pentyl,

2,2-dimethyl-1-butyl, 2,3-dimethyl-1-butyl, 3,3-dimethyl-1-butyl, 2-ethyl-1-butyl,
2,3"dimethyl-2-butyl, 3,3-dimethyl-2-butyl, heptyl, octyl, 2-etylhexyl, 2,4,4-tri-
methylpentyl, 1,1,3,3-tetramethylbutyl, 1 -nonyl, 1 -decyl, 1 -undecyl, 1 -dodecyl,
1 -tridecyl, 1 -tetradecyl, 1 -pentadecyl, 1 -hexadecyl, 1 -heptadecyl, 1 -octadecyl,
cyclopentylmethyl, 2-cyclopentyiethyl, 3-cyclopenty)propyl, cyclohexylmethyl,
2-cyclohexylethyl, 3-cyclohexylpropyl, benzyl (phenylmethyl), diphenylmethyl
(benzhydryl), triphenylmethyl, 1-phenylethyl, 2-phenylethyl, 3-phenylpropyl,
a,a-dimethylbenzyl, p-tolylmethyl, 1-(p-butylphenyl)ethyl, p-chlorobenzyl, 2,4-
dichlorobenzyl, p-methoxybenzyl, m-ethoxybenzyl, 2-cyanoethyl, 2-cyanopropyl, 2-
methoxycarbonylethyl, 2-ethoxycarbonylethyl, 2-butoxycarbonylpropyl, 1,2-
di(metho)cycarbonyl)ethyl, methoxy, ethoxy, formyl, 1,3-dioxolan-2-yl, 1,3-dioxan-2-yl,
2-methyl-1,3-dioxolan-2-yl, 4-methyl-1,3-dioxolan-2-yl, 2-hydroxyethyl, 2-
hydroxypropyl, 3-hydroxypropyl, 4-hydroxybutyl, 6-hydroxyhexyl, 2*aminoethyl, 2-
aminopropyl, 3-aminopropyl, 4-aminobutyl, 6-aminohexyl, 2-methylaminoethyl, 2-
methylaminopropyl, 3-methylaminopropyl, 4-methylaminobutyl, 6-methylaminohexyl, 2-
dimethylaminoethyl, 2-dimethylaminopropyl, 3-dimethylaminopropyl, 4-
dimethylaminobutyl, 6-dimethylaminohexyl, 2-hydroxy-2,2-dimethylethyl, 2-phenoxyethyl, 2-phenoxypropyl, 3-phenoxypropyl, 4-phenoxybutyl, 6-phenoxyhexyl, 2-methoxyethyl, 2-methoxypropyl, 3-methoxypropyl, 4-methoxybutyl, 6-methoxyhexyl, 2-ethoxyethyl, 2-ethoxypropyl, 3-ethoxypropyl, 4-ethoxybutyl, 6-ethoxyhexyl, acetyl, CnF2(n-a)+(i-b)H2a+b where n is from 1 to 30, 0
C2-C18-Alkenyl which is optionally substituted by functional groups, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatoms and/or heterocycles and/or interrupted by one or more oxygen and/or sulfur atoms and/or one or more substituted or unsubstituted imino groups is preferably vinyl, 2-propenyl, 3-butenyl, cis-2-butenyl, trans-2-butenyl or CnF2(n-a)-(i-b)H2a-b whsre n S 30, 0 Ce-Cia-Aryl which is optionally substituted by functional groups, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatoms and/or heterocycles is preferably phenyl, tolyl, xylyl, a-naphthyl, 3-naphthyl, 4-diphenylyl, chlorophenyl, dichlorophenyl, trichlorophenyl, difluorophenyl. methylphenyl, dimethylphenyl, trimethylphenyl, ethylphenyl, diethylphenyl, isopropylphenyi, tert-butylphenyl, dodecylphenyl, methoxyphenyl, dimethoxyphenyl, ethoxyphenyl, hexyloxyphenyl, methylnaphthyl, isopropylnaphthyl, chloronaphthyl, ethoxynaphthyl, 2,6-dimethylphenyl, 2,4,6-trlmethylphenyl, 2,6-dimethoxyphenyl, 2,6-dichlorphenyl, 4-bromophenyl, 2-nitrophenyl, 4-nitrophenyl, 2,4-dinitrophenyl, 2,6-dinitrophenyl, 4-dJmethylaminophenyl, 4-acetylphenyl, ethoxyethylphenyl, ethoxymethylphenyl, methylthlophenyl, isopropylthiophenyl or tert-butylthiophenyl or C6F(5.a)Ha where 0 C5-Ci2-Cycloalkyl which is optionally substituted by functional groups, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatoms and/or heterocycles is preferably cyclopentyl, cyclohexyl, cyclooctyl, cyclododecyl, methylcyclopentyl, dimethylcyclopentyl, methylcyclohexyl, dimethylcyclohexyl, diethylcyclohexyl, butylcyclohexyl, methoxycyclohexl, dimethoxycyclohexyl, diethoxycyclohexyl, butylthiocyclohexyl, chlorocyclohexyl, dichlorocyclohexyl, dichlorocyclopentyl, CnF2(n-a)-(i-b)H2aH3 where n C5-C12-Cycloalkenyl which is optionally substituted by functional groups, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatoms and/or heterocycles is preferably 3-cyclopentenyl, 2-cyclohexenyl, 3-cyclohexenyl, 2,5-cycioh6xadienyl or CnF2(n-a)-3(i-b)H2a-3b where n A five- or six-membered, oxygen-, nitrogen- and/or sulfur-comprising heterocycle which is optionally substituted by functional groups, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatoms and/or heterocycles is preferably furyl, thiophenyl, pyrryl, pyridyl, indolyl, benzoxazolyl, dioxolyl, dioxyl, benzimidazolyl, benzthiazolyl, dimethylpyridyl, methylquinolyl, dimethylpyrryl, methoxyfuryl, dimethoxypyridyl or difluoropyridyl.

If two adjacent radicals together form an unsaturated, saturated or aromatic ring which Is optionally substituted by functional groups, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatoms and/or heterocycles and optionally interrupted by one or more oxygen and/or sulfur atoms and/or one or more substituted or unsubstltuted imino groups, the two radicals together are 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 -C1-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.
If the abovementioned radicals comprise oxygen and/or sulfur atoms and/or substituted or unsubstltuted imino groups, the number of oxygen and/or sulfur atoms and/or imino groups is not subject to any restrictions. In general, there will be no more than 5 in the radical, preferably no more than 4 and very particularly preferably no more than 3.
If the abovementioned radicals comprise heteroatoms, there is generally at least one carbon atom, preferably at least two carbon atoms, between any two heteroatoms.
The radicals R1 to R9 are particularly preferably, independently of one another,
• hydrogen;
• unbranched or branched C1-C16-alkyl which is unsubstltuted or substituted by one or more hydroxy, halogen, phenyl, cyano, C1-C6-alkoxycarbonyl and/or sulfonic acid substituents and has a total of from 1 to 20 carbon atoms, for example 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-methyl-3-pentyl, 2,2-dimethyl-1 -butyl, 2,3-dimethyl-1 -butyl, 3,3-dimethyl-1-butyl, 2-ethyl-1-butyl, 2,3-dimethyl-2-butyl, 3,3-dimethyl-2-butyl, 1-heptyl, 1-octyl, 1-nonyl, 1-decyl, 1-undecyl, 1-dodecyl, 1-tetradecyl, 1-hexa-decyl, 1-octadecyl, 2-hydroxyethyl, benzyl, 3-phenylpropyl, 2-cyanoethyl, 2-(methoxycarbonyl)ethyl, 2-(ethoxycarbonyl)ethyl, 2-(n-butoxycarbonyl)ethyl, trifluoromethyl, difluoromethyl, fluoromethyl, pentafluoroethyl, heptafluoropropyl, heptafluoroisopropyl, nonafluorobutyl, nonafluoroisobutyl, undecylfluoropentyl, undecylfiuoroisopentyl, 6-hydroxyhexyl and propylsulfonic acid;

• glycols, butylene glycols and oligomers thereof having from 1 to 100 units and a
hydrogen atom or a C1-Cs8alkyI group as end group, for example

hydrogen, methyl or ethyl and n is preferably from 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;
• vinyl; and
• N,N-di-Ci-C6-alkylamino, for example N,N-dimethylamino and N,N-diethylamino.
The radicals R1 to R9 are very particularly preferably, independently of one another, hydrogen or C1-C19-alkyl, for example methyl, ethyl, 1-butyl, 1-pentyl, 1-hexyl, 1-heptyl, 1-octyl, phenyl, 2-hydroxyethyl, 2-cyanoethyl, 2-(methoxycarbonyl)ethyl, 2"(ethoxycarbonyl)ethyl, 2-(n-butoxycarbonyl)ethyl, N,N-dimethylamino, N,N-diethylamino, chlorine or CH3O-(CH2CH2O)n-CH2CH2- and CH3CH2O-(CH2CH2O)n-CH2CH2- where n is from 0 to 3.
Very particularly preferred pyridinium ions (IVa) are those in which
• one of the radicals R1 to R5 is methyl, ethyl or chlorine and the remaining radicals
R1 to R5 are hydrogen;
• R3 is dimethylamino and the remaining radicals R1, R2, R'4 and R5 are hydrogen;
• all radicals R1 to R5 are hydrogen;
• R2 is carboxy or carboxamide and the remaining radicals R1,R2, R4 and R5 are
hydrogen; or
• R1 and R2 or R2 and R3 are together 1,4-buta-1,3-dienylene and the remaining
radicals R1, R2, R4 and R5 are hydrogen;

and, in particular, those in which

Very particularly preferred pyridinium ions (IVa) are 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 -tetra-
decyl)pyridinium, 1-(1-hexadecyl)pyridinium, 1,2-dimethylpyridinium, 1-ethyl-2-methyl-
pyridinium, 1-(1-butyl)-2-methylpyridinium, 1-(1-hexyl)-2-methylpyridinium,
1 -(1 -octyl)-2-methylpyridinium, 1 -(1 -dodecyl)-2-methylpyridinium, 1 -(1 -tetradecyl)-2-methylpyridinium, 1-(1-hexadecyl)-2"methylpyridinium, 1-methyl-2-ethylpyridinium, 1,2-diethylpyridinium, 1 -(1 -butyl)-2"ethylpyridinium, 1 -(1 -hexyl)-2-ethylpyridinium, 1 -(1 -octyl)-2-ethylpyridinium, 1 -(1 "dodecyl)-2-ethylpyridinium, 1 -(1 -tetradecyl)-2-ethyl-pyridinium, 1 -(1 -hexadecyl)"2-ethylpyridinium, 1,2-dimethyl-5-ethylpyridinium, 1,5-di-ethyl-2-methylpyridinium, 1 -(1 -butyl)-2-methyl-3-ethylpyridinium, 1 -(1 -hexyl)-2-methyl-3-ethylpyridinium and 1-(1-octyl)-2-methyl-3-ethylpyridinium, 1-(1-dodecyl)-2-methyl-3-ethylpyridinium, 1-(1-tetradecyl)-2-methyl-3-ethylpyridinium and 1-(1-hexadecyl)-2-methyl"3-ethylpyridinium.

Very particularly preferred pyrazinium ions (IVd) are those in which

Very particularly preferred imidazolium ions (IVe) are 1 -methylimidazolium, 1 -ethylimidazolium, 1 -(1 -butyl)imidazolium, 1 -(1 -octyl)imidazolium, 1 -(1 -dode-cyl)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-ethyl-imidazolium, 1 -(1 -hexyl)-3-butylimidazolium, 1 -(1 -octyl)-3-methylimidazolium, 1 -(1 -octyl)-3-ethylimidazolium, 1-(1-octyl)"3-butylimidazolium, 1-(1-dodecyl)-3-methyl-imidazolium, 1-(1-dodecyl)-3-ethylimidazolium, 1-(1-dodecyl)-3-butylimidazolium, 1-(1-dodecyl)-3-octylimidazolium, 1 -(1 -tetradecyl)-3-methylimidazolium, 1 -(1 -tetradecyl)-3-ethylimidazolium, 1 -(1 -tetradecyl)-3-butylimidazolium, 1 -(1 -tetradecyl)-3-octylimi-dazolium, 1-(1-hexadecyl)-3-methylimidazolium, 1-(1-hexadecyl)-3-ethylimidazolium, 1-(1 -hexadecyl)-3-butylimidazolium, 1 -(1 -h6xadecyl)-3-octylimidazolium, 1,2-dimethyl-imidazolium, 1,2,3-trimethylimidazolium, 1 -ethyl-2,3-dimethylimidazolium, 1 -(1 -butyl)-2,3-dimethylimidazolium, 1 -(1 -hexyl)-2,3-dlmethylimidazolium, 1 -(1 -octyl)-2,3-di-methyllmidazolium, 1,4-dimethylimidazolium, 1,3,4-trlmethylimidazolium, 1,4-dimethyl-3-ethylimidazolium, 3-butylimidazolium, 1,4-dimethyl-3-octylimidazolium, 1,4,5-tri-methylimidazolium, 1,3,4,5-tetramethylimidazolium, 1,4,5-trimethyl-3-ethylimidazolium, 1,4,5-trimethyl-3-butylimidazolium and 1,4,5-trimethyl"3-octylimidazolium.
Very particularly preferred pyrazolium ions (IVf), (IVg) or (IVg') are those in which
• R1 is hydrogen, methyl or ethyl and R1 to R4 are each, independently of one another, hydrogen or methyl.

Very particularly preferred pyrazolium ions (IVh) are those in which

Very particularly preferred 1-pyrazolinium ions (IVi) are those in which

Very particularly preferred 2-pyrazolinium ions (IVj) or (IVj') are those in which

Very particularly preferred thiazolium Ions (IVo) or (IVo') and oxazolium ions (IVp) are those in which
• R1 is hydrogen, methyl, ethyl or phenyl and R2 and R3 are each, independently
of one another, hydrogen or methyl.
Very particularly preferred 1,2,4-triazolium ions (IVq), (IVq') or (IVq") are those in which
• R1 and R2 are each, independently of one another, hydrogen, methyl, ethyl or
phenyl and R^ is hydrogen, methyl or phenyl.
Very particularly preferred 1,2,3-triazolium ions (IVr), (IVr') or (IVr") are those in which
• R1 is hydrogen, methyl or ethyl and R2 and R3 are each, independently of one
another, hydrogen or methyl, or R2 and R3 are together 1,4-buta-l ,3-dienylene.
Very particularly preferred pyrrolidinium ions (IVs) are those in which
• R1 is hydrogen, methyl, ethyl or phenyl and R2 to R9 are each, independently of
one another, hydrogen or methyl.
Very particularly preferred imidazolidinium ions (IVt) are those in which
• R1 and R4 are each, independently of one another, hydrogen, methyl, ethyl or
phenyl and R2 and R3 and also R5 to R8 are each, independently of one
another, hydrogen or methyl.
Very particularly preferred ammonium ions (IVu) are those in which
• R1 to R3 are each, independently of one another, C1-C18-alkyI; or
• R1 and R2 are together 1,5-pentylene or 3-oxa-1,5-pentylene and R3 is C1-C18-alkyl, 2-hydroxyethyl or 2-cyanoethyL
Very particularly preferred ammonium ions (IVu) are methyltri(1-butyl)ammonium, N,N-dimethylpiperidinium and N,N-dimethylmorpholinium.

Examples of tertiary amines from which the quaternary ammonium ions of the general
formula (IVu) are derived from quaternation by the abovementioned radicals R are
diethyl-n-butylamine, diethyi-tert-butylamine, diethyl-n-pentylamine, diethylhexylamine,
diethyloctylamine, diethyl(2-ethylhexyl)amine, di-n-propylbutylamine, di-n-propyl-n-
pentylamine, di-n-propylhexylamine, di-n-propyloctylamine, di-n-propyl(2-ethyl-
hexyl)amine, diisopropylethylamine, diisopropyl-n-propylamine, diisopropylbutylamine,
diisopropylpentylamine, diisopropylhexylamine, diisopropyloctylamine, diisopropyl(2-
ethylhexyl)amine, di-n-butylethylamine, di-n-butyl-n-propylamine, di-n-butyl-n-
pentylamine, di-n-butylhexylamine, di-n-butyloctylamine, di-n-butyl(2-ethylhexyl)amine,
N-n-butylpyrrolidine, N-sec-butylpyrrolidine, N-tert-butylpyrrolidine, N-n-
pentylpyrrolidine, N,N-dimethylcyclohexylamine, N.N-diethylcyclohexylamine, N,N-di-n-butylcyclohexylamine. N-n-propylpiperidine, N-isopropylpiperidine, N-n-butylpiperidine, N-sec-butylpiperidine, N-tert-butylpiperidine, N-n-pentylpiperidine, N-n-butylmorpholine, N-sec-butylmorpholine, N-tert-butylmorpholine, N-n-pentylmorpholine, N-benzyl-N-ethylaniline, N-benzyl-N-n-propylaniline, N-benzyl-N-isopropylaniline, N-benzyl-N-n-butylaniline, N,N-dimethyl-p-toluidene, N,N-diethyl-p-toluidene, N,N-di-n-butyl-p-toluidene, diethylbenzylamine, dl-n-propylbenzylamine, di-n-butylbenzylamine, diethylphenylamine, di-n-propylphenylamine and di-n-butylphenylamine.
Preferred tertiary amines (IVu) are diisopropylethylamine, diethyl-tert-butylamine, diisopropylbutylamine, di-n-butyl-n-pentylamine, N,N-di-n-butylcyclohexylamine and tertiary amines derived from pentyl isomers.
Particularly preferred tertiary amines are di-n-butyl-n-pentylamine and tertiary amines derived from pentyl isomers. A further preferred tertiary amine which has three identical radicals is triallylamine.
Very particularly preferred guanidinium ions (IVv) are those in which
• R1 to R5 are methyl.
A very particularly preferred guanidinium ion (IVv) is N,N,N',N',N",N"-hexamethylguanldinium.

Very particularly preferred choiinium ions (IVw) are those in which
• R1 and R2 are each, independently of one another, methyl, ethyl, 1-butyl or 1-octyl and R3 is hydrogen, methyl, ethyl, acetyl, -SO2OH or-PO(OH)2;
• R^ is methyl, ethyl, 1-butyl or 1-octyl, R^ is a -CH2-CH2-OR'^ group and R^ and R'* are each, independently of one another, hydrogen, methyl, ethyl, acetyl, -SO2OH or -P0(OH)2; or
• R1 I S a -CH2-CH2-OR'4 group, R2 is a -CH2-CH2-OR5 group and R3 to R5 are
each, independently of one another, hydrogen, methyl, ethyl, acetyl, -SO2OH or -PO(OH)2.
Particularly preferred choiinium ions (IVw) are those in which R3 is selected from among hydrogen, methyl, ethyl, acetyl. 5-methoxy-3"Oxapentyl, 8-methoxy-3,6-dioxaoctyl, 11-methoxy-3,6,9-trioxaundecyl, 7-methoxy-4-oxaheptyl, 11-methoxy-4,8-dioxaundecyl, 15-methoxy-4,8,12-trioxapentadecyl, 9-methoxy-5-oxanonyl, 14-meth-oxy-5,10-oxatetradecyl, 5-ethoxy-3-oxapentyl, 8-ethoxy-3,6-dioxaoctyl, 11 -ethoxy-3,6,9-trioxaundecyl, 7-ethoxy-4-oxaheptyl, 11 -ethoxy-4,8-dioxaundecyl, 15-ethoxy-4,8,12-trioxapentadecyl, 9-ethoxy-5-oxanonyl or 14-ethoxy-5,10-oxatetradecyL
Very particularly preferred phosphonium ions (IVx) are those in which
• R1 to R3 are each, independently of one another, C1-C18-alkyl, in particular butyl,
isobutyl, 1-hexyl or 1-octyL
Among the abovementioned heterocyclic cations, the pyridinium ions, pyrazolinium ions, pyrazolium ions and imidazolinium ions and also the imidazolium ions are preferred. Preference is also given to ammonium ions.
Very particular preference is given to 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 -hexa-decyOpyridinium, 1,2-dimethylpyridinium, 1 -ethyl-2-methylpyridinium, 1 -(1 -butyl)-2-methylpyridinium, 1-(1-hexyl)-2-methylpyridinium, 1-(1-octyl)-2-methyipyridinium, 1-(1-dodecyl)-2-methylpyridinium, 1-(1 -tetradecyl)-2-methylpyridinium, 1 -(1 -hexadecyl)-2-methylpyridinium, 1-methyl-2-ethylpyridlnium, 1,2-diethylpyridinium, 1-(1-butyl)-2-

ethylpyridinium, 1-(1-hexyl)-2-ethylpyridinium, 1"(1-octyl)-2-ethylpyridinium, 1-(1-dode-
cyl)-2-ethylpyridinium, 1 -(1 -tetradecyl)-2-ethylpyridinium, 1 -(1 -hexadecyl)-2"ethyl-
pyridinium, 1,2-dimethyl-5-ethylpyridinium, 1,5-diethyl-2-methylpyridinium, 1-(1-butyl)-
2-methyl-3-ethylpyridinium, 1 -(1 -hexyl)-2-methyl-3"ethylpyridinium, 1 -(1 -octyl)-2-
methyl-3-ethylpyridinium, 1-(1-dodecyl)-2-methyl-3-ethylpyridinium, 1-(1-tetradecyl)-2-
methyl-3-ethylpyridinium, 1 -(1 -hexadecyl)-2-methyl"3-ethylpyridinium, 1 -methyl-
imidazolium, 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 -hexyl)-3-methylimidazolium, 1 -(1 -octyl)-3-methylimidazolium, 1 -(1 -dodecyl)"3-
methylimidazolium, 1 -(1 -tetradecyl)-3-methylimidazolium, 1 -(1 -hexadecyl)-
3-methylimidazolium, 1,2-dimethylimidazolium, 1,2,3-trimethylimidazolium, 1-ethyl-2,3-dimethylimidazolium, 1 -(1 -butyl)-2,3-dimethylimidazolium, 1 -(1 -hexyl)-2,3-dimethyl-imidazolium and 1-(1-octyl)-2,3-dimethylimidazolium, 1,4-dimethylimidazolium, 1,3,4-trimethylimidazolium, 1,4-dimethyl-3-ethylimidazolium, 3-butylimidazolium, 1,4-dimethyl-3-octylimidazolium, 1,4,5-trimethylimidazolium, 1,3,4,5-tetramethylimida-zolium, 1,4,5-trimethyl-3-ethylimidazolium, 1,4,5-trimethyl-3-butylimidazolium and 1,4,5-trimethyl-3-octylimidazolium.

• the group of alkoxides and aryloxides of the general formula: RaO";

comprising heterocycle, where two of them may together form an unsaturated, saturated or aromatic ring which is optionally interrupted by one or more oxygen and/or sulfur atoms and/or one or more unsubstituted or substituted imino groups, where the radicals mentioned may each be additionally substituted by functional groups, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatoms and/or heterocycles.
Here, Ci-Ci8-alkyl which is optionally substituted by functional groups, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatoms and/or heterocycles is, for example, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, 2-ethylhexyl, 2,4,4-trimethylpentyl, decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, 1,1-dimethylpropyl, 1,1-dimethylbutyl, 1,1,3,3-tetramethylbutyl, benzyl, 1-phenylethyl, a,a-dimethylbenzyl, benzhydryl, p-tolylmethyl, 1-(p-butylphenyl)ethyl, p-chlorobenzyl, 2,4-dichlorobenzyl, p-methoxybenzyl, m-ethoxybenzyl, 2-cyanoethyl, 2-cyanopropyl, 2-methoxycarbonylthyl, 2-ethoxycarbonylethyl, 2-butoxycarbonylpropyl, 1,2-di-(methoxycarbonyl)ethyl, 2-methoxyethyl, 2-ethoxyethyl, 2-butoxyethyl, diethoxymethyl, diethoxyethyl, 1,3-dioxolan-2-yl, 1,3-dioxan-2-yl, 2-methyl-1,3-dioxolan-2-yl, 4-methyl-1,3-dioxolan-2-yl, 2-isopropoxyethyl, 2-butoxypropyl, 2-octyloxyethyl, chloromethyl, trichloromethyl, trifluoromethyl, 1,1-dimethyl-2-chloroethyl, 2-methoxyisopropyl, 2-ethoxyethyl, butylthiomethyl, 2-dodecylthioethyl, 2-phenlythioethyl, 2,2,2-trifluoroethyl, 2-hydroxyethyl, 2-hydroxypropyl, 3-hydroxypropyl, 4-hydroxybutyl, 6-hydroxyhexyl, 2-aminoethyl, 2-aminopropyl, 4-aminobutyl, 6-aminohexyl, 2-methylaminoethyl, 2-methylaminopropyl, 3-methylaminopropyl, 4-methylaminobutyl, 6-methylaminohexyl,

2-dimethylaminoethyl, 2-dimethylaminopropyl, 3-dimethylaminopropyl, 4-dimethyl-aminobutyl, 6-dimethylaminohexyl, 2-hydroxy-2,2-dimethylethyl, 2-phenoxyethyl, 2"phenoxypropyl, 3-phenoxypropyl, 4-phenoxybutyl, 6-phenoxyhexyl, 2-methoxyethyl, 2-methoxypropyl, 3-methoxypropyl, 4-methoxybutyl, 6-methoxyhexyl, 2-ethoxyethyl, 2-ethoxypropyl, 3-ethoxypropyl, 4-ethoxybutyl or 6-ethoxyhexyl,
C2-C18-Alkyl which is optionally substituted by one or more nonadjacent oxygen and/or sulfur atoms and/or one or more substituted or unsubstituted imino groups is, for example, 5-hydroxy-3-oxapentyl, 8-hydroxy-3,6-dioxaoctyl, 11-hydroxy-3,6,9-tri-oxaundecyl, 7-hydroxy-4-oxaheptyl, 11-hydroxy-4,8-dioxaundecyl, 15-hydroxy-4,8,12-trioxapentadecyl, 9-hydroxy-5"Oxanonyl, 14-hydroxy-5,10-oxatetradecyl, 5"methoxy-3-oxapentyl, 8-methoxy-3,6-dioxaoctyl, 11 -methoxy-3,6,9-trioxaundecyl, 7-methoxy-4-oxaheptyl, 11-methoxy-4,8"dioxaundecyl, 15-methoxy-4,8,12-trioxapentadecyl, 9-methoxy-5-oxanonyl, 14"methoxy-5,10-oxatetradecyl, 5-ethoxy-3-oxapentyl, S-ethoxy-3,6-dioxaoctyl, 11 -ethoxy-3,6,9-trioxaundecyl, 7-ethoxy-4-oxaheptyl, 11 -ethoxy-4,8-dioxaundecyl, 15-ethoxy-4,8,12-trioxapentadecyl, 9-ethoxy-5-oxanonyl or 14-ethoxy-5,10-oxatetradecyl,
If two radicals form a ring, these radicals can together form, for example, 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 -CrC4-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 as fused-on building block.
The number of nonadjacent oxygen and/or sulfur atoms and/or imino groups is in principle not subject to any restrictions or is automatically restricted by the size of the radical or the cyclic building block. In general, it will be no more than 5 in the respective radical, preferably no more than 4 and very particularly preferably no more than 3. Furthermore, there is generally at least one carbon atom, preferably at least two carbon atoms, between any two heteroatoms.
Substituted and unsubstituted imino groups can be, for example, imino, methylimino, isopropylimino, n-butylimino or tert-butylimino.
For the purposes of the present invention, the term "functional groups" refers, for example, to the following: carboxy, carboxamide, hydroxy, di-(C1-C4-alkyl)amino, C1-

C4-alkyloxycarbonyl, cyano or Ci-C4-alkoxy. Here, C1-C4-alkyl is methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl or tert-butyl.
C6-C14-Aryl which is optionally substituted by functional groups, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatoms and/or heterocycles is, for example, phenyl, tolyl, xylyl, a-naphthyl, p-naphthyl, 4-diphenylyl, chlorophenyl, dichlorophenyl, trichlorophenyl, difluorophenyl, methylphenyl, dimethylphenyl, trimethylphenyl, ethylphenyl, diethylphenyl, isopropylphenyl, tert-butylphenyl, dodecylphenyl, methoxyphenyl, dimethoxyphenyl, ethoxyphenyl, hexyloxyphenyl, methylnaphthyl, isopropylnaphthyl, chloronaphthyi, ethoxynaphthyl, 2,6-dimethylphenyl, 2,4,6-trimethylphenyl, 2,6-dimethoxyphenyl, 2,6-dichlorophenyl, 4-bromophenyl, 2- or 4-nitrophenyl, 2,4- or 2,6-dinitrophenyl, 4-dimethylaminophenyl, 4-acetylphenyl, methoxyethylphenyl or ethoxymethylphenyl.
C5-Ci2-Cycloalkyl which is optionally substituted by functional groups, aryl, alkyl, aryloxy, halogen, heteroatoms and/or heterocycles is, for example, cyclopentyl, cyclohexyl, cyclooctyl, cyclododecyl, methylcyclopentyl, dimethylcyclopentyl, methylcyclohexyl, dimethylcyclohexyl, diethylcyclohexyl, butylcyclohexyl, methoxycyclohexyl, dimethoxycyclohexyl, diethoxycyclohexyl, butylthiocyclohexyl, chlorocyclohexyl, dichlorocyclohexyl, dichlorocyclopentyl or a saturated or unsaturated bicyclic system such as norbornyl or norbornenyl.
A five- or six-membered, oxygen-, nitrogen- and/or sulfur-comprising heterocycle is, for example, furyl , thiophenyl, pyryl, pyridyl, indolyl, benzoxazolyl, dioxolyl, dioxyl, benzimidazolyl, benzthiazolyl, dimethylpyridyl, methylquinolyl, dimethylpyryl, methoxyfuryl, dimethoxypyridyl, difluoropyridyl, methylthiophenyl, isopropylthiophenyl or tert-butylthiophenyl.
Preferred anions are selected from the group of halides and halogen-comprising compounds, the group of carboxylic acids, the group of sulfates, sulfites and sulfonates and the group of phosphates.
Preferred anions are chloride, bromide, iodide, SCN", OCN', CN", acetate, C1-C4-alkylsulfates, R1-COO', R1SO3', R1RbPOV, methanesulfonates, tosylate, C1-C4 dialkylphosphates, hydrogen sulfate or tetrachloroaluminate.

Particularly preferred anions are CI", CH3COO" or CH3SO3".
Both cations and anions are present in the ionic liquid. Within the ionic liquid, a proton or an alkyl radical is transferred from the cation to the anion. This forms two uncharged molecules. There is thus an equilibrium in which anions, cations and the two uncharged molecules formed therefrom are present.
The solution preferably has a temperature of not more than 180°C. The solution of the present invention more preferably has a temperature of not more than 160°C, even more preferably not more than 120°C and particularly preferably not more than 100°C.
In a preferred embodiment, the proportion of nitrogen-comprising base is 6 - 20% by weight, more preferably 6 - 15% by weight, even more preferably 6 to 14% by weight, even more preferably 6 to 13% by weight, particularly preferably from 6 to 10% by weight, based on the total weight of the solution. Furthermore the proportion is preferably 7 to 14% by weight, especially 8 to 13% by weight.
The nitrogen-comprising base is preferably a compound whose nitrogen atom or atoms is/are primary, secondary or tertiary and which is derived from the quaternary compounds of the formulae (IVa) to (IVw), with the radical R forming the quaternary nitrogen not being present and the other substituents having, independently of one another, the abovementioned meanings and also being able, if appropriate, to be hydrogen.
The base is preferably derived from the cation present in the ionic liquid, if this is a quaternary nitrogen-comprising compound. However, it is also possible for this not to be the case.
Further preferred bases are listed in DE-A 102 02 838 on page 4, line 17, to page 7, line 51, the disclosure of which is hereby fully incorporated by reference.
Particularly preferred bases are amines, imidazoles, monoethylamine, isopropylamine, ethylhexylamine, ethanolamine or imidazole.
The present invention further provides a process for preparing a solution according to the invention, which comprises the steps

addition of cellulose to a solution comprising an ionic liquid comprising anions and cations as solvent and from 6 to 30% by weight of a nitrogen-comprising base, based on the total weight of the solution, and
mixing of the solution until the cellulose is completely dissolved.
Mixing is preferably carried out by means of stirring, shaking and/or with the aid of microwaves.
The dissolution preferably occurs within 3 days, more preferably within one day and particularly preferably within 12 hours.
The present invention further provides for the use of a solution according to the present invention for the physical or chemical treatment of cellulose.
The chemical treatment can comprise oxidation, reduction, pyrolysis, hydrolysis, isomeration, sterification, alkoxylation or copolymerization.
The present invention is illustrated by the following examples.

Examples
An amount of an ionic liquid and an amine is placed in a reaction vessel at 95°C with stirring and is admixed with an amount of cellulose powder. The mixture is stirred at 95oC until the cellulose has dissolved completely. In addition, the time required for this is determined.
The batch sizes and results are summarized in the following table.

BMIM = 1-n-butyl-3-methylimidazolium

Claims
1. A solution comprising cellulose, an ionic liquid comprising anions and cations as solvent and 6 - 30% by weight of a nitrogen-comprising base, based on the total weight of the solution, wherein the ionic liquid comprises at least one cation of formula (IVe)

and oligomers comprising these structures, where
• the radical R is hydrogen, a carbon-comprising organic, saturated or unsaturated, acyclic or cyclic, aliphatic, aromatic or araliphatic radical which has from 1 to 20 carbon atoms and is unsubstituted or interrupted by from 1 to 5 heteroatoms or functional groups or substituted; and
• the radicals R1 to R9 are each, independently of one another, hydrogen, a sulfo group or a carbon-comprising organic, saturated or unsaturated, acyclic or cyclic, aliphatic, aromatic or araliphatic radical which has from 1 to 20 carbon atoms and is unsubstituted or interrupted by from 1 to 5 heteroatoms or functional groups or substituted, with the radicals R1 to R9 which are bound to a carbon atom (and not to a heteroatom) in the abovementioned formulae (IV) also being able to be halogen or a functional group; or
two adjacent radicals from the group consisting of R1 to R9 can together also be a divalent, carbon-comprising organic, saturated or unsaturated, acyclic or cyclic, aliphatic, aromatic or araliphatic radical which has from 1 to 30 carbon atoms and is unsubstituted or interrupted by from 1 to 5 heteroatoms or functional groups or substituted.

• the group of alkoxides and aryloxides of the general formula
R'O";
• the group of halometalates of the general formula
[MqHalr]9--,
where M is a metal and Hal is fluorine, chlorine, bromine or iodine, q and r are positive integers and indicate the stoichiometry of the complex and s is a positive integer and indicates the charge on the complex;
• the group of sulfides, hydrogen sulfides, polysulfides, hydrogen polysulfides and
thiolates of the general formulae:
S'-, HS-, [Sv]'-, [HSv]-, [R^S]-.
where v is a positive integer from 2 to 10; and

nitrogen- and/or sulfur-comprising heterocycle, where two of them may together form an unsaturated, saturated or aromatic ring which is optionally interrupted by one or more oxygen and/or sulfur atoms and/or one or more unsubstituted or substituted imino groups, where the radicals mentioned may each be additionally substituted by functional groups, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatoms and/or heterocycles.

5. The solution according to any of claims 1 to 4 which has a temperature of not
more than 180°C.
6. The solution according to any of claims 1 to 5. wherein the proportion of the
nitrogen-comprising base is 6 - 20% by weight, based on the total weight of the
solution.
7. The solution according to any of claims 1 to 6, wherein the nitrogen-comprising
base is a compound whose nitrogen atom or atoms is/are primary, secondary or
tertiary and which is derived from the quaternary compounds of the formula (IVe).
with the radical R forming the quaternary nitrogen of the quaternary compounds
not being present and the other substituents having, independently of one
another, the meanings given in claim 1, and also being able, if appropriate, to be
hydrogen.
8. A process for preparing a solution according to any of claims 1 to 7, which
comprises the steps
addition of cellulose to a solution comprising an ionic liquid comprising anions and cations as defined in claim 1 as solvent and from 6 to 30% by weight of a nitrogen-comprising base, based on the total weight of the solution, and
mixing of the solution until the cellulose is completely dissolved.
9. Method of using a solution according to any of claims 1 to 7 for the physical or
chemical treatment of cellulose.
Dated this 15 day of October 2007

Documents:

4580-CHENP-2007 AMENDED CLAIMS 13-12-2011.pdf

4580-CHENP-2007 AMENDED PAGES OF SPECIFICATION 18-08-2011.pdf

4580-CHENP-2007 AMENDED CLAIMS 18-08-2011.pdf

4580-CHENP-2007 AMENDED PAGES OF SPECIFICATION 13-12-2011.pdf

4580-CHENP-2007 CORRESPONDENCE OTHERS 01-03-2011.pdf

4580-CHENP-2007 CORRESPONDENCE OTHERS 09-12-2013.pdf

4580-CHENP-2007 CORRESPONDENCE OTHERS 13-12-2011.pdf

4580-CHENP-2007 CORRESPONDENCE OTHERS 11-04-2014.pdf

4580-CHENP-2007 EXAMINATION REPORT REPLY RECEIVED 18-08-2011.pdf

4580-CHENP-2007 FORM-3 09-12-2013.pdf

4580-CHENP-2007 FORM-3 13-12-2011.pdf

4580-chenp-2007 form-3 18-08-2011.pdf

4580-CHENP-2007 POWER OF ATTORNEY 18-08-2011.pdf

4580-CHENP-2007 AMENDED CLAIMS 29-04-2014.pdf

4580-CHENP-2007 AMENDED PAGE OF SPECIFICATION 29-04-2014.pdf

4580-CHENP-2007 CORRESPONDENCE OTHERS 13-12-2013.pdf

4580-CHENP-2007 EXAMINATION REPORT REPLY RECEIVED 29-04-2014.pdf

4580-CHENP-2007 FORM-3 13-12-2013.pdf

4580-CHENP-2007 FORM-3 29-04-2014.pdf

4580-chenp-2007-abstract.pdf

4580-chenp-2007-claims.pdf

4580-chenp-2007-correspondnece-others.pdf

4580-chenp-2007-description(complete).pdf

4580-chenp-2007-form 1.pdf

4580-chenp-2007-form 18.pdf

4580-chenp-2007-form 26.pdf

4580-chenp-2007-form 3.pdf

4580-chenp-2007-form 5.pdf

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Patent Number

260689

Indian Patent Application Number

4580/CHENP/2007

PG Journal Number

21/2014

Publication Date

23-May-2014

Grant Date

16-May-2014

Date of Filing

15-Oct-2007

Name of Patentee

BASF AKTIENGESELLSCHAFT

Applicant Address

D-67056, LUDWIGSHAFEN,GERMANY

Inventors:

#	Inventor's Name	Inventor's Address
1	MASSE, MATTHIAS,	AM KLIPFELSTOR 4, 67346 SPEYER, GERMANY
2	STEGMANN, VEIT	SIEGSTRASSE 14, 68167 MANNHEIM GERMANY

PCT International Classification Number

C08B 1/00

PCT International Application Number

PCT/EP06/61560

PCT International Filing date

2006-04-12

PCT Conventions:

#	PCT Application Number	Date of Convention	Priority Country
1	102005017733.6	2005-04-15	Germany