US2017015871A1PendingUtilityA1
Method for curing an adhesive using microwave irradiation
Est. expiryNov 29, 2033(~7.4 yrs left)· nominal 20-yr term from priority
C09J 11/06C09J 5/06C08F 2/46
60
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Claims
Abstract
A method for curing a polymer adhesive composition using microwaves, characterized in that the adhesive composition contains an ionic liquid [A] + a [B] a− , wherein [A] + represents a cation, [B] a− represents an anion, and a represents an integer.
Claims
exact text as granted — not AI-modified1 . A method for curing a polymer adhesive composition comprising:
curing the polymer adhesive composition using microwaves, and wherein the adhesive composition contains an ionic liquid [A] + a [B] a− , where [A] + represents a cation, [B] a− represents an anion and “a” represents an integer.
2 . A method according to claim 1 , wherein [A] + represents an ammonium cation [R 1′ R 1 R 2 R 3 N] + , a phosphonium cation [R 1′ R 1 R 2 R 3 ] 30 , a sulfonium cation [R 1′ R 1 R 2 R 3 S] + , a hetero-aromatic cation or a guanidinium cation R 3 R 3 ′N(C═NR 1 R 1 ′)NR 2 R 2 ′ of the formula:
where R 1 , R 1′ , R 2 , R 2′ and R 3 , R 3 ′ represent hydrogen or organic residues, e.g., independently of each other hydrogen, or unsubstituted alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl, aryl or saturated or unsaturated heterocyclyl, e.g., heteroaryl, wherein the 7 residues mentioned last, independently of each other, may be unsubstituted or substituted by one or more halogen and/or 1 to 3 residues selected from
(C 1 -C 6 )alkyl, aryl, saturated or unsaturated heterocyclyl, e.g., heteroaryl, (C 3 -C 7 )cycloalkyl, halogen, OR c , SR c , NR c R d , COR c , COOR c , CO—NR c R d , acrylate, methacrylate, cyanoacrylate, epoxide, vinyl, vinyl ether, vinyl ester, styrene, allyl, phenol, alkyl phenol, ketone, amidoamine, urea, urethane, imidazole, benzimidazole, isocyanate, dicarboxylic acid anhydride, resorcinol, melamine, siloxane, alkoxy siloxane, wherein R c and R d independently of each other represent hydrogen, (C 1 -C 6 )alkyl, halo(C 1 -C 6 )alkyl, cycloalkyl, in particular cyclopentyl, cyclohexyl, phenyl, tolyl or benzyl; or wherein two of the residues R 1 , R 1′ , R 2 , R 2′ , R 3 , R 3′ together with the hetero atom, to which they are bound, form a saturated or unsaturated ring, which is unsubstituted or substituted, and
wherein each carbon chain may be disrupted by one or several hetero atoms selected from the group consisting of O, S, NH or N(C 1 -C 4 )alkyl.
3 . A method according to claim 2 , wherein the heterocycyl residue is unsaturated and selected from a 5-or 6-membered hetero-aromatic, which has at least one nitrogen atom as well as optionally an oxygen or sulphur atom and which is unsubstituted or substituted and/or annulated, in particular selected from the group of the formula
wherein
R, R 1 ′ independently of each other represent hydrogen, (C 1 -C 30 )alkyl, (C 3 -C 12 )cycloalkyl, (C 2 -C 30 )alkenyl, (C 3 -C 12 )cycloalkenyl, aryl or saturated or unsaturated heterocyclyl, in particular heteroaryl, wherein the 6 residues last mentioned are each independently of each other unsubstituted or substituted by
one or several halogen residues, and/or 1 to 3 residues selected from the group consisting of (C 1 -C 30 )alkyl, aryl, saturated or unsaturated heterocyclyl, in particular heteroaryl, C 3 -C 7 )cycloalkyl, halogen, OR c , SR c , NR c R d , COR c , COOR c , CO—NR c R d , acrylate, methacrylate, cyanoacrylate, epoxide, vinyl, vinyl ether, vinyl ester, styrene, allyl, phenol, alkyl phenol, ketone, amidoamine, urea, urethane, imidazole, benzimidazole, isocyanate, dicarboxylic acid anhydride, resorcinol, melamine, siloxane, alkoxy siloxane, wherein
R c and R d independently of each other represent hydrogen, (C 1 -C 6 )alkyl, halo(C 1 -C 6 )alkyl, cycloalkyl, in particular cyclopentyl, cyclohexyl, phenyl, tolyl or benzyl;
R 4 , R 5 , R 6 , R 7 , R 8 independently of each mean hydrogen, halogen, nitro, cyano, OR c , SR c , NR c R d , COR c , COOR c , CO—NR c R d , (C 1 -C 30 )alkyl, (C 3 -C 12 )cycloalkyl, (C 2 -C 30 )alkenyl, (C 3 -C 12 )cycloalkenyl, aryl or saturated or unsaturated heterocyclyl, in particular heteroaryl, wherein the 6 residues last mentioned are each independently of each unsubstituted or substituted by
one or several halogen and/or 1 to 3 residues selected from the group consisting of
(C 1 -C 6 )alkyl, aryl, saturated or unsaturated heterocyclyl, in particular heteroaryl, (C 3 -C 7 )cycloalkyl, halogen, OR c , SR c , NR c R d , COR c , COOR c , CO—NR c R d , acrylate, methacrylate, cyanoacrylate, epoxide, vinyl, vinyl ether, vinyl ester, styrene, allyl, phenol, alkyl phenol, ketone, amidoamine, urea, urethane, imidazole, benzimidazole, isocyanate, dicarboxylic acid anhydride, resorcinol, melamine, siloxane, alkoxy siloxane, wherein R c and R d independently of each other represent hydrogen, (C 1 -C 6 )alkyl, halo(C 1 -C 6 )alkyl, cycloalkyl, in particular cyclopentyl, cyclohexyl, phenyl, tolyl or benzyl,
or
two of the residues R, R 4 , R 5 , R 6 , R 7 , R 8 , which are adjacent to each other, form together with the atom, to which they are bound, a ring, wherein this may be unsaturated or saturated, in particular aromatic, unsubstituted or substituted and wherein the carbon chain formed by the respective residues may be disrupted by one or several heteroatoms selected from the group consisting of O, S, N, NH or N(C 1 -C 4 )alkyl;
R c , R f , R g , R h independently of each other mean hydrogen, alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl, aryl or heteroaryl residues, wherein the 7 residues last mentioned independently of each other may support one or several halogen residues and/or 1 to 3 residues selected from the group consisting of (C 1 -C 6 )alkyl, aryl, heteroaryl, (C 3 -C 7 )cycloalkyl, halogen, OR c , SR c , NR c R d , COR c , COOR c , CO—NR c R d , acrylate, methacrylate, cyanoacrylate, epoxide, vinyl, vinyl ether, vinyl ester, styrene, allyl, phenol, alkyl phenol, ketone, amidoamine, urea, urethane, imidazole, benzimidazole, isocyanate, dicarboxylic acid anhydride, resorcinol, melamine, siloxane, alkoxy siloxane, wherein R c and R d independently of each other mean hydrogen, (C 1 -C 6 )alkyl, halo(c 1 -c 6 )alkyl, cycloalkyl, in particular cyclopentyl, cyclohexyl, phenyl, tolyl or benzyl.
4 . A method according to claim 1 , wherein [B] a− is selected from:
fluoride, chloride, bromide, iodide, dicyanamide, thiocyanate; perchlorate, hexafluorophosphate, nitrite, nitrate, sulphate, hydrogen sulphate, carbonate, hydrogen carbonate, alkyl carbonate, methyl carbonate, aryl carbonate; phosphate; hydrogen phosphate; dihydrogen phosphate; sulfamate H 2 N—SO 3 − , deprotonated acesulfame (6-methyl-2,2-dioxo-oxathiazine-4-olate), deprotonated saccharine (1,1-dioxo-3-one-1,2-benzothiazolate), cyclamate (deprotonated cyclohexane sulfamic acid),
a tetra-substituted borate of the general formula (Va) [BR i R j R k R l ] − , wherein R i to R 1 independently of each other represent fluoro or (C 1 -C 30 )alkyl, (C 3 -C 12 )cycloalkyl, (C 2 -C 30 )alkenyl, (C 3 -C 12 )cycloalkenyl, aryl or saturated or unsaturated heterocyclyl, in particular heteroaryl, wherein the 6 residues last mentioned independently of each other are unsubstituted or substituted by
one or several halogen and/or
1 to 3 residues selected from the group consisting of (C 1 -C 30 )alkyl, aryl, saturated or unsaturated heterocyclyl, in particular heteroaryl, (C 3 -C 7 )cycloalkyl, halogen, Or c , SR c , NR c R d , COR c , COOR c , CO—NR c R d , acrylate, methacrylate, cyanoacrylate, epoxide, vinyl, vinyl ether, vinyl ester, styrene, allyl, phenol, alkyl phenol, ketone, amidoamine, urea, urethane, imidazole, benzimidazole, isocyanate, dicarboxylic acid anhydride, resorcinol, melamine, siloxane, alkoxy siloxane, wherein
R c and R d independently of each other represent hydrogen, (C 1 -C 6 )alkyl, halo (C 1 -C 6 )alkyl, cycloalkyl, in particular cyclopentyl, cyclohexyl, phenyl, tolyl or benzyl;
or
two of the residues R i to R l form together with the boron atom, to which they are bound, a five-, six- or seven-membered ring, wherein this may be saturated or unsaturated, unsubstituted or substituted and wherein the carbon chain formed by the respective carbon atoms may be disrupted by one or several heteroatoms selected from the group consisting of 0, S, N, NH or N-C 1 -C 4 -alkyl,
or
organic sulfonate of the general formula (Vb)[R m —SO 3 ] − or organic sulphate of the general formula (Vc)[R m —OSO 3 ] − , wherein
R m represents (C 1 -C 30 )alkyl, (C 3 -C 12 )cycloalkyl, (C 2 -C 30 )alkenyl, (C 3 -C 12 )cycloalkenyl, aryl or saturated or unsaturated heterocyclyl, in particular heteroaryl, wherein the 6 residues mentioned last independently of each other are unsubstituted or substituted by
one or several halogen, and/or
1 to 3 residues selected from the group consisting of (C 1 -C 30 )alkyl, aryl, saturated or unsaturated heterocyclyl, in particular heteroaryl, (C 3 -C 7 )cycloalkyl, halogen, OR c , SR c , NR c R d , COR c , COOR c , CO—NR c R d , acrylate, methacrylate, cyanoacrylate, epoxide, vinyl, vinyl ether, vinyl ester, styrene, allyl, phenol, alkyl phenol, ketone, amidoamine, urea, urethane, imidazole, benzimidazole, isocyanate, dicarboxylic acid anhydride, resorcinol, melamine, siloxane, alkoxy siloxane, wherein
R c and R d independently of each other represent hydrogen, (C 1 -C 6 )alkyl, halo(C 1 -C 6 )alkyl, cycloalkyl, in particular cyclopentyl, cyclohexyl, phenyl, tolyl or benzyl;
carboxylate of the general formula (Vd) [R n —COO] − , wherein
R n represents hydrogen or (C 1 -C 30 )alkyl, (C 3 -C 12 )cycloalkyl, (C 2 -C 3o )alkenyl, (C 3 -C 12 )cycloalkenyl, aryl or saturated or unsaturated heterocyclyl, in particular heteroaryl, wherein the 6 residues mentioned last independently of each other are unsubstituted or substituted by
one or several halogen, and/or
1 to 3 residues selected from the group consisting of the group (C 1 -C 30 )alkyl, aryl, saturated or unsaturated heterocyclyl, in particular heteroaryl, (C 3 -C 7 )cycloalkyl, halogen, OR c , SR c , NR c R d , COR c , COOR c , CO—NR c R d , acrylate, methacrylate, cyanoacrylate, epoxide, vinyl, vinyl ether, vinyl ester, styrene, allyl, phenol, alkyl phenol, ketone, amidoamine, urea, urethane, imidazole, benzimidazole, isocyanate, dicarboxylic acid anhydride, resorcinol, melamine, siloxane, alkoxy siloxane, wherein
R c and R d independently of each other represent hydrogen, (C 1 -C 6 )alkyl, halo(C 1 -C 6 )alkyl, cycloalkyl, in particular cyclopentyl, cyclohexyl, phenyl, tolyl or benzyl;
or
carboxylate, which formally is derived by way of deprotonation of one or optionally also several carboxylic acid groups of fruit acids, saccharic acids, amino acids, fatty acids, volatile acids and resin acids or which is conjugated into these acids, respectively;
a (fluoroalkyl)fluorophosphate of the general formula (Vc) [PF x (C y F 2y+1−z H z ) 6−x ] − , wherein 1≦x≦6, 1≦y≦8 and 0≦z≦2y+1;
or
an imide of the general formulae (Vf) [R o —SO 2 —N—SO 2 -R p ] − , (Vg) [R q —SO 2 —N—CO—R r ] − or (Vh) [R s —CO—N—CO—R r ] − , [R s -CO-N-CO-R t ] − , wherein
R o to R t independently of each other represent hydrogen or (C 1 -C 30 )alkyl, (C 3 -C 12 )cycloalkyl, (C 2 -C 30 )alkenyl, (C 3 -C 12 )cycloalkenyl, aryl or saturated or unsaturated heterocyclyl, in particular heteroaryl, wherein the 6 residues mentioned last independently of each other are unsubstituted or substituted by
one or several halogen and/or
1 to 3 residues selected from the group consisting of (C 1 -C 30 )alkyl, aryl, saturated or unsaturated heterocyclyl, in particular heteroaryl, (C 3 -C 7 )cycloalkyl, halogen, OR c , SR c , NR c R d , COR c , COOR c , CO—NR c R d , acrylate, methacrylate, cyanoacrylate, epoxide, vinyl, vinyl ether, vinyl ester, styrene, allyl, phenol, alkyl phenol, ketone, amidoamine, urea, urethane, imidazole, benzimidazole, isocyanate, dicarboxylic acid anhydride, resorcinol, melamine, siloxane, alkoxy siloxane, wherein
R c and R d independently of each other represent hydrogen, (C 1 -C 6 )alkyl, halo(C 1 -C 6 )alkyl, cycloalkyl, in particular cyclopentyl, cyclohexyl, phenyl, tolyl or benzyl;
an organic phosphate of the general formula (Vi) [R u —OPO 3 ] 2− or (Vj) [R u O—PO 2 —OR v ] − or an organic phosphonate of the general formula (Vk) [R u —PO 3 ] 2− or (Vl) [R u —PO 2 —OR v ] − , wherein
R u and R v independently of each other represent hydrogen or (C 1 -C 30 )alkyl, (C 3 -C 12 )cycloalkyl, (C 2 -C 30 )alkenyl, (C 3 -C 12 )cycloalkenyl, aryl or heteroaryl, wherein the 6 residues mentioned last independently of each other are unsubstituted or substituted by
one or several halogen and/or
1 to 3 residues selected from the group consisting of (C 1 -C 30 )alkyl, aryl, saturated or unsaturated heterocyclyl, in particular heteroaryl, (C 3 -C 7 )cycloalkyl, halogen, OR c , SR c , NR c R d , COR c , COOR c , CO—NR c R d , acrylate, methacrylate, cyanoacrylate, epoxide, vinyl, vinyl ether, vinyl ester, styrene, allyl, phenol, alkyl phenol, ketone, amidoamine, urea, urethane, imidazole, benzimidazole, isocyanate, dicarboxylic acid anhydride, resorcinol, melamine, siloxane, alkoxy siloxane, wherein
R c and R d independently of each other represent hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -halogenalkyl, cyclopentyl, cyclohexyl, phenyl, tolyl or benzyl.
5 . A method according to claim 1 , wherein anion [B] a− is a complex of a central metal atom M +v of the oxidation number v=1,2,3,4,5 or 6 and ligands X − , e.g., a complex of the general formula [M +v X v+1 ] − (Vm) or [M +v X v+2 ] 2− (Vn) or [M +v X v+3 ] 3− (Vo), wherein
M +v is selected from the elements of the transition metals,
in particular selected from the elements Ag, Al, Ce, Cs, Cr, Co, Cu, Dy, Er, Eu, Gd, Ho, Ir, Fe, Mn, Mo, Nd, Ni, Pt, Pr, Re, Rh, Rb, Ru, Sm, Sn, Ta, Tb, Tm, Ti, W, V and Y, in particular in the oxidation states Ag + , Al +3 , Ce +2 , Ce +3 , Ce +4 , Cs +1 , Cr +2 , Cr +3 , Cr +6 , Co +2 , Co +3 , Cu +1 , Cu +2 , Dy +3 , Er +2 , Eu +3 , Eu +3 , Gd +2 , Gd +3 , Ho +2 , Ho +3 , Ir +4 , Fe +2 , Fe +3 , Mn +2 , Mn +3 , Mo +2 , Mo +3 , Mo +4 , Mo +5 , Nd +2 , Nd +3 , Ni +2 , Ni +3 , Pt +4 , Pr +2 , Pr +3 , Re +4 , Re +6 , Rh +2 , Rh +3 , Rb +4 , Ru +3 , Ru +4 , Sn +2 , Sn +4 , Sm +2 , Sm +3 , Ta +5 , Tb +3 , Tm +3 , Ti +2 , Ti +3 , W +4 , W +5 , V +2 , V +3 , V +4 , V +5 , Y +2 and Y +3 , wherein
each individual of the ligands X is independently of each other selected in particular from: fluoride, chloride, bromide, iodide, thiocyanate, dicyanamide, nitrite; nitrate; acetyl acetone; acyl; adenine; 2,2′-azobisisobutyronitrile; alanine; allyl; allyloxycarbonyl; water; aryl; arginine; asparagine; aspartate; BIAB N; biotinyl; 2,2 ‘-bis(diphenyl-pho sphino)-6,6 ’-dimethoxy-1,1′-biphenyl; 2,2′-binaphtyldiphenyldiphosphine; 1,2bis [4,5dihydro-3H binaphtho [1,2-c:2′, 1′-e]phosphepino]benzol; 1,1′-bis {4,5-dihydro-3H-dinaphtho [1,2-c:2′,1∝-e]phosphepino} ferrocene; 4,4′-di-tert-butyl-4,4′,5,5′-tetrahydro-3,3′-bis-3H-di-naphtho[2,1-c:1′,2,2′-e]phosphepine; BINAL; 4,5dihydro-3H-di-naphtho[2,1-c;1′,2′-e]phosphepine ; 2,2′-binaphtyldiol; bistertbutylbipyridine; benzylmethylphenylphosphine; benzyl; tert-butoxycarbonyl; bis(2-((S)-4iso-propyl-4,5dihydrooxazol-2yl)phenyl)amine; bis(2-((S)-4-tert-butyl-4,5dihydroox azol-2yl)phenyl)amine; 1,2-bis(2,5-diethyl-pho spholano)-ethane; butoxy-carbonyl-4diphenylphosphino-2diphenylphosphino-methylpyrrolidine; 2,2′-bipyridin; benzoyl; benzyloxycarbonyl; CO; cycloheptatrienyl; citrulline; citrate; cyanide; cyclooctadiene; cyclooctatetraene; cyclopentadienyl; pentamethylcyclopentadienyl; cyclohexyl; cytidine; cysteine; cytosine; dibenzilidenacetone; O-isopropylidene-2,3dihydroxy-1,4-bis(diphenylphosphino)butane; (1R,2R)-bis[(2-methoxyphenyl)phenyl-phosphino]ethane; 4-dimethylamino pyridine; dimethylglyoxime, dipivaloyl methanate; Dess-Martin periodinane; 1,4,7,10-tetraaz a-cyclododecane-1,4,7,10-tetraacetate; diphenylphosphenylethane; diphenylphosphenyl methane; diphenylphosphenyl propane; desoxy ribose; diethylentriamine-pentaacetate; bis(2,5dimethylphospholano)-benzol; ethylene diamintetraacetate; ethylene diamine; fluorenyl methoxycarbonyl; 7,7-dimethyl-1,1,1,2,2,3,3-heptafluorooctan-4,6-dionato; galactose; galactosamine; N-acetyl galactosamine, glycolyl; glucose; glucosamine, N-acetyl-glucosamine, glutamine, glutamate, glycine, guanine; guanosine; haemoglobin; hexafluoroacetyl acetonate; histidine; hexamethyl phosphoric acid triamide; hydroxyproline; isoleucine; leucine; lysine; 2,2′-bis[(N,N-dimethylamino)(phenyl)methyl]-1,1′-bisdicyclohexyl-phosphino)ferrocene; myoglobin; methionine; methaemoglobin; metmyoglobin; 3,5dioxa-4-phosphacyclohepta[2,1-a;3,4-a′]dinapthalene-4yl)dimethyl amine; methylphenylpropyl phosphine; methylsulfone; bicyclo[2.2.1]hepta-2,5-; neuraminic acid; N-acetyl-neuraminic acid; N-glycolyl-neuraminic acid; 2,3bis(diphenylphosphino)-bicyclo[2.2.1]hept-5-ene; nitrilo-triacetic acid; ornithine; succinate; oxalate; phenyl oanisylmethyl phosphine; phthalo cyanine; phenyl alanine; phenanthroline; picolyl amine; piperidine; para-nitro-benzoic acid; porphyrin; proline; pyridyl; PYBOX; pyroglutamate ; pyrazine; ribose; sarcosine; salene; serine; succinyl; 1,4,7-triazacyclononane; tert-butyl-di-methyl-silyl; tartrate; terpyridine; thymidine; threonine; thymine; tetramethylethylene diamine; trimesic acid; tris(pyrazolyl)borate; triphenyl phosphane; tryptophane; tyrosine; tetrazole; ubiquitin; uracil; uridine; valine.
6 . A method according to claim 1 , wherein
defined, carbon containing, organic, saturated or unsaturated, acyclic or cyclic, aliphatic, aromatic or araliphatic residues contain 1 to 30 carbon atoms, the residues R i to R 1 at the tetra-substituted borate (Va), the residue R m at the organic sulfonate (Vb) and sulphate (Vc), the residue R n at the carboxylate (Vd), the residues R o to R t at the (fluoroalkyl)fluoro phosphate (Ve), the imides (Vf),(Vg) and (Vh), the residues R u and R v at the organic phosphates (Vi),(Vj) and the organic phosphonates (Vk),(Vl) independently of each other preferably mean: (C 1 -C 30 )alkyl and the aryl-, heteroaryl-, cycloalkyl-, halogen-, hydroxy-, amino-, carboxy-, formyl-, —O—, —CO—, —CO—O—or —CO—N<substituted components thereof, in particular 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-l-butyl, 2-methyl-2-butyl, 3-methyl-2-butyl, 2,2-dimethyl-l-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-l-butyl, 3,3 -dimethyl-1-butyl, 2-ethyl-1-butyl, 2,3-dimethyl-2-butyl, 3,3-dimethyl-2-butyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, icosyl, henicosyl, do co s yl, tricosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, triacontyl, phenylmethyl (benzyl), diphenylmethyl, triphenylmethyl, 2-phenylethyl, 3-phenylpropyl, cyclopentylmethyl, 2-cyclopentylethyl, 3-cyclopentylpropyl, cyclohexylmethyl, 2-cyclohexylethyl, 3-cyclohexylpropyl, methoxy, ethoxy, formyl, acetyl or C n F 2(n−a)+(1−b) H 2a+b with n≦30, 0≦a≦n and b=0 or 1 (for example, CF 3 , C 2 F 5 , CH 2 CH 2 —C (n−2) F 2(n−2)+1 , C 6 F 13 , C 8 F 17 , C 10 F 21 , C 12 F 25 ); (C 3 -C 12 )cycloalkyl and the aryl-, heteroaryl-, cycloalkyl-, halogen-, hydroxy-, amino-, carboxy-, formyl-, —O—, —CO—or —CO—O—-substituted components thereof, such as, e.g., cyclopentyl, 2-methyl-1-cyclopentyl, 3-methyl-1-cyclopentyl, cyclohexyl, 2-methyl-l-cyclohexyl, 3-methyl-1-cyclohexyl, 4-methyl-1-cyclohexyl or C, a F 2(n−a)−(1−b) H 2a−b with n≦30, 0≦a≦n and b=0 or 1; (C 2 -C 30 )alkenyl and the aryl-, heteroaryl-, cycloalkyl-, halogen-, hydroxy-, amino-, carboxy-, formyl-, —O—, —CO—or —CO—O-substituted components thereof, in particular 2-propenyl, 3-butenyl, cis-2-butenyl, trans-2-butenyl or C a F 2(n−a)−(1−b) H 2a−b with n≦30, 0≦a≦n and b=0 or 1; (C 3 -C 12 )cycloalkenyl and the aryl-, heteroaryl-, cycloalkyl-, halogen-, hydroxy-, amino-, carboxy-, formyl-, —O—, —CO—or —CO—O-substituted components thereof, in particular 3-cyclopentenyl, 2-cyclohexenyl, 3-cyclohexenyl, 2,5-cyclohexadienyl or CF n F 2(n−a)−3(1−b) H 2a−3b with n≦30, 0≦a≦n and b=0 or 1; aryl or saturated or unsaturated heterocyclyl, in particular heteroaryl having 2 to 30 carbon atoms and the alkyl-, aryl-, heteroaryl-, cycloalkyl-, halogen-, hydroxy-, amino-, carboxy-, formyl-, —O—, —CO—or —CO—O-substituted components thereof, in particular phenyl, 2-methyl-phenyl (2-tolyl), 3-methyl-phenyl (3-tolyl), 4-methyl-phenyl, 2-ethyl-phenyl, 3-ethyl-phenyl, 4-ethyl-phenyl, 2,3-dimethyl-phenyl, 2,4-dimethyl-phenyl, 2,5-dimethyl-phenyl, 2,6-dimethyl-phenyl, 3,4-dimethyl-phenyl, 3,5-dimethyl-phenyl, 4-phenyl-phenyl, 1-naphthyl, 2-naphthyl, 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl or C 6 F (5−a) H a with 0≦a≦5.
7 . A method according to claim 1 , wherein 5 -95 wt. % metal salts [M] b+ [B] y a− have been added to the ionic liquids, wherein a,b,x,y independently of each other mean the integers 1,2,3 or 4 and wherein the product of x and b equals the product of y and a,
wherein in particular the metal cations are selected from Cr +2 , Cr +3 , Co +2 , Co +3 , Cu +1 , Cu +2 , Fe +2 , Fe +3 , Mn +2 , Mn +3 , Ni +2 , Ni + 3 , Ti +2 , Ti +3 , Li + , Na + , K + , Cs + , Mg 2+ , Ca 2+ , Ba 2 , Sr 2+ , Zr 4+ , Sn 2+ , Sn 4+ , Ag + , Zn 2+ and Al 3+ , especially preferred ones being Co +2 , Co +3 , Cu +1 , Cu +2 , Fe +2 , Fe +3 , Mn +2 , Mn +3 , Ti +2 , Ti +3 , Li + , Na + , K + , Mg 2+ , Ca 2+ , Zn 2+ and Al 3+ .Cited by (0)
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