# US 2019/0169469 A1 · Method for curing an adhesive using microwave irradiation

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- Number: US 2019/0169469 A1
- Document ID: US20190169469A1
- Status: Published application
- Kind: A1
- Application number: 16/266,944
- Filed: 2019-02-04
- Published: 2019-06-06
- Earliest claimed: 2013-11-29
- Assignees: Proionic GmbH
- Applicants: Proionic GmbH
- Inventors: Robert Wutti; Ronald Kalb
- Web page: https://patentgrep.com/patent/US20190169469A1

## CPC

- C09J 5/06: involving heating of the applied adhesive
- C09J 11/06: organic
- C09J: ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES (preparation of glue or gelatine C09H)

## Abstract

The present invention relates to a method method for bonding a thermoplastic material by way of providing a thermoplastic material, applying an ionic liquid to a surface of the thermoplastic material, contacting the thermoplastic material with a separate material, and exposing the resulting arrangement to microwave radiation to melt the surface of the thermoplastic material to which the ionic liquid was applied and allow the adherence of the thermoplastic material to the separate material.

## Claims

### Claim 1

A method for bonding a thermoplastic material, the method comprising the steps of:
providing a thermoplastic material;
applying an ionic liquid [A]+a[B]a− to a surface of the thermoplastic material, wherein
[A]+ represents a cation,
[B]a− represents an anion, and
“a” represents an integer;
contacting the thermoplastic material with a separate material to form an arrangement, wherein the surface of the thermoplastic material to which the ionic liquid was applied is in contact with the separate material; and
exposing the arrangement to microwave radiation, whereupon the surface of the thermoplastic material to which the ionic liquid was applied melts to enable adherence of the thermoplastic material to the separate material.

### Claim 2 (depends on 1)

The method of claim 1, wherein the separate material is a second thermoplastic material.

### Claim 3 (depends on 1)

The method of claim 1, wherein the ionic liquid is applied by introducing or injecting.

### Claim 4 (depends on 1)

The method of claim 1, wherein the ionic liquid is applied as thin layer.

### Claim 5 (depends on 1)

The method of claim 1, wherein a pressure is applied to contact the materials.

### Claim 6 (depends on 1)

The method of claim 1, wherein the thermoplastic material to which the ionic liquid was applied melts locally restricted.

### Claim 7 (depends on 1)

The method of claim 1, wherein [A]+ represents an ammonium cation [R1′R1R2R3N]+, a phosphonium cation [R1′R1R2R3P]+, a sulfonium cation [R1′R1R2S]+, a hetero-aromatic cation, or a guanidinium cation R3R3′N(C═NR1R1′)NR2R2′ of the formula:
where R1, R1′, R2, R2′ and R3, R3′ represent hydrogen or one or more organic residues.

### Claim 8 (depends on 7)

The method of claim 7, wherein R1,R1′,R2,R2′ and R3,R3′ represent independently of each other hydrogen or substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, saturated or unsaturated heterocyclyl, or heteroaryl.

### Claim 9 (depends on 8)

The method of claim 8, wherein the alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, saturated or unsaturated heterocyclyl, or heteroaryl, independently of each other, are substituted with one or more halogens and/or 1 to 3 residues selected from (C1-C6)alkyl, aryl, saturated or unsaturated heterocyclyl, (C3-C7)cycloalkyl, halogen, ORc, SRc, NRcRd, CORc, COORc, CO—NRcRd, 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, and wherein Rc and Rd independently of each other represent hydrogen, (C1-C6)alkyl, halo(C1-C6)alkyl, cycloalkyl, cyclopentyl, cyclohexyl, phenyl, tolyl or benzyl.

### Claim 10 (depends on 8)

The method of claim 8, wherein two of the residues R1,R1′,R2, R2′,R3, R3′ together with a hetero atom to which they are bound form a saturated or unsaturated ring, which is unsubstituted or substituted.

### Claim 11 (depends on 9)

The method of claim 9, wherein at least one carbon chain is disrupted by one or several hetero atoms selected from the group consisting of O, S, NH and N(C1-C4)alkyl.

### Claim 12 (depends on 8)

The method of claim 8, wherein at least one of R1,R1′,R2,R2′ and R3,R3′ represents an saturated or unsaturated heterocyclyl and the heterocycyl residue is an unsaturated 5- or 6-membered hetero-aromatic selected from:
wherein,
R, R1′ independently of each other represent hydrogen, (C1-C30)alkyl, (C3-C12)cycloalkyl, (C2-C30)alkenyl, (C3-C12)cycloalkenyl, aryl, saturated or unsaturated heterocyclyl, or 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 (C1-C30)alkyl, aryl, saturated or unsaturated heterocyclyl, heteroaryl, C3-C7)cycloalkyl, halogen, ORc, SRc, NRcRd, CORc, COORc, CO—NRcRd, 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 Rc and Rd independently of each other represent hydrogen, (C1-C6)alkyl, halo(C1-C6)alkyl, cycloalkyl, cyclopentyl, cyclohexyl, phenyl, tolyl or benzyl;
R4, R5, R6, R7, R8 independently of each mean hydrogen, halogen, nitro, cyano, ORc, SRc, NRcRd, CORc, COORc, CO—NRcRd, (C1-C30)alkyl, (C3-C12)cycloalkyl, (C2-C30)alkenyl, (C3-C12)cycloalkenyl, aryl, saturated or unsaturated heterocyclyl, or 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
(C1-C6)alkyl, aryl, saturated or unsaturated heterocyclyl, heteroaryl, (C3-C7)cycloalkyl, halogen, ORc, SRc, NRcRd, CORc, COORc, CO—NRcRd, 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 Rc and Rd independently of each other represent hydrogen, (C1-C6)alkyl, halo(C1-C6)alkyl, cycloalkyl, cyclopentyl, cyclohexyl, phenyl, tolyl or benzyl, or
two of the residues R, R4, R5, R6, R7, R8, which are adjacent to each other, form together with the atom, to which they are bound, a ring, wherein the ring is unsaturated, saturated, or aromatic and 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(C1-C4)alkyl;
Re, Rf, Rg, Rh independently of each other mean hydrogen, alkyl, alkenyl, alkynyl, 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 (C1-C6)alkyl, aryl, heteroaryl, (C3-C7)cycloalkyl, halogen, ORc, SRc, NRcRd, CORc, COORc, CO—NRcRd, 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 Rc and Rd independently of each other mean hydrogen, (C1-C6)alkyl, halo(c1-c6)alkyl, cycloalkyl, cyclopentyl, cyclohexyl, phenyl, tolyl or benzyl.

### Claim 13 (depends on 1)

The method of 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 H2N—SO3−, deprotonated acesulfame, deprotonated saccharine, cyclamate;
a tetra-substituted borate of the general formula (Va) [BRiRjRkRl]−, wherein Ri to Rl independently of each other represent fluoro or (C1-C30)alkyl, (C3-C12)cycloalkyl, (C2-C30)alkenyl, (C3-C 12)cycloalkenyl, aryl or saturated or unsaturated heterocyclyl, 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 (C1-C30)alkyl, aryl, saturated or unsaturated heterocyclyl, (C3-C7)cycloalkyl, halogen, ORc, SRc, NRcRd, CORc, COORc, CO—NRcRd, 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, and alkoxy siloxane, wherein Rc and Rd independently of each other represent hydrogen, (C1-C6)alkyl, halo (C1-C6)alkyl, cycloalkyl, cyclopentyl, cyclohexyl, phenyl, tolyl or benzyl; or
two of the residues Ri to Rl 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 O, S, N, NH or N—C1-C4-alkyl, or
organic sulfonate of the general formula (Vb)[Rm—SO3]− or organic sulphate of the general formula (Vc)[Rm—OSO3]−, wherein Rm represents (C1-C30)alkyl, (C3-C12)cycloalkyl, (C2-C30)alkenyl, (C3-C12)cycloalkenyl, aryl or saturated or unsaturated heterocyclyl, 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 (C1-C30)alkyl, aryl, saturated or unsaturated heterocyclyl, (C3-C7)cycloalkyl, halogen, ORc, SRc, NRcRd, CORc, COORc, CO—NRcRd, 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, and alkoxy siloxane, wherein Rc and Rd independently of each other represent hydrogen, (C1-C6)alkyl, halo(C1-C6)alkyl, cycloalkyl, cyclopentyl, cyclohexyl, phenyl, tolyl or benzyl;
carboxylate of the general formula (Vd) [Rn—COO]−, wherein Rn represents hydrogen or (C1-C30)alkyl, (C3-C12)cycloalkyl, (C2-C30)alkenyl, (C3-C12)cycloalkenyl, aryl or saturated or unsaturated heterocyclyl, 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 (C1-C30)alkyl, aryl, saturated or unsaturated heterocyclyl, (C3-C7)cycloalkyl, halogen, ORc, SRc, NRcRd, CORc, COORc, CO—NRcRd, 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, and alkoxy siloxane, wherein Rc and Rd independently of each other represent hydrogen, (C1-C6)alkyl, halo(C1-C6)alkyl, cycloalkyl, 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 (Ve) [PFx(CyF2y+1-zHz)6-x]−, wherein 1≤x≤6, 1≤y≤8 and 0≤z≤2y+1; or
an imide of the general formulae (Vf) [Ro—SO2—N—SO2—Rp]−, (Vg) [Rq—SO2—N—CO—Rr]− or (Vh) [Rs—CO—N—CO—Rt]−, wherein Ro to Rt independently of each other represent hydrogen or (C1-C30)alkyl, (C3-C12)cycloalkyl, (C2-C30)alkenyl, (C3-C12)cycloalkenyl, aryl or saturated or unsaturated heterocyclyl, 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 (C1-C30)alkyl, aryl, saturated or unsaturated heterocyclyl, (C3-C7)cycloalkyl, halogen, ORc, SRc, NRcRd, CORc, COORc, CO—NRcRd, 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, and alkoxy siloxane, wherein Rc and Rd independently of each other represent hydrogen, (C1-C6)alkyl, halo(C1-C6)alkyl, cycloalkyl, cyclopentyl, cyclohexyl, phenyl, tolyl or benzyl;
an organic phosphate of the general formula (Vi) [Ru—OPO3]2− or (Vj) [RuO—PO2—ORv]− or an organic phosphonate of the general formula (Vk) [Ru—PO3]2− or (Vl) [Ru—PO2—ORv]−, wherein Ru and Rv independently of each other represent hydrogen or (C1-C30)alkyl, (C3-C12)cycloalkyl, (C2-C30)alkenyl, (C3-C12)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 (C1-C30)alkyl, aryl, saturated or unsaturated heterocyclyl, (C3-C7)cycloalkyl, halogen, ORc, SRc, NRcRd, CORc, COORc, CO—NRcRd, 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, and alkoxy siloxane, wherein Rc and Rd independently of each other represent hydrogen, C1-C6-alkyl, C1-C6-halogenalkyl, cyclopentyl, cyclohexyl, phenyl, tolyl or benzyl.

### Claim 14 (depends on 13)

A method according to claim 13, wherein
defined, carbon containing, organic, saturated or unsaturated, acyclic or cyclic, aliphatic, aromatic or araliphatic residues contain 1 to 30 carbon atoms,
the residues Ri to Rl at the tetra-substituted borate (Va), the residue Rm at the organic sulfonate (Vb) and sulphate (Vc), the residue Ru at the carboxylate (Vd), the residues Ro to Rt at the (fluoroalkyl)fluoro phosphate (Ve), the imides (Vf),(Vg) and (Vh), the residues Ru and Rv at the organic phosphates (Vi),(Vj) and the organic phosphonates (Vk),(Vl) independently of each other mean:
(C1-C30)alkyl and the aryl-, heteroaryl-, cycloalkyl-, halogen-, hydroxy-, amino-, carboxy-, formyl-, —O—, —CO—, —CO—O— or —CO—N< substituted components thereof, 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, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, icosyl, henicosyl, docosyl, 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 CnF2(n-a)+(1-b)H2a+b with n≤30, 0≤a≤n and b=0 or 1;
(C3-C12)cycloalkyl and the aryl-, heteroaryl-, cycloalkyl-, halogen-, hydroxy-, amino-, carboxy-, formyl-, —O—, —CO—, —CO—O-substituted components thereof, cyclopentyl, 2-methyl-1-cyclopentyl, 3-methyl-1-cyclopentyl, cyclohexyl, 2-methyl-1-cyclohexyl, 3-methyl-1-cyclohexyl, 4-methyl-1-cyclohexyl or CnF2(n-a)-(1-b)H2a-b with n≤30, 0≤a≤n and b=0 or 1;
(C2-C30)alkenyl and the aryl-, heteroaryl-, cycloalkyl-, halogen-, hydroxy-, amino-, carboxy-, formyl-, —O—, —CO—, —CO—O-substituted components thereof, 2-propenyl, 3-butenyl, cis-2-butenyl, trans-2-butenyl or CnF2(n-a)-(1-b)H2a-b with n≤30, 0≤a≤n and b=0 or 1;
(C3-C12)cycloalkenyl and the aryl-, heteroaryl-, cycloalkyl-, halogen-, hydroxy-, amino-, carboxy-, formyl-, —O—, —CO—, —CO—O-substituted components thereof, 3-cyclopentenyl, 2-cyclohexenyl, 3-cyclohexenyl, 2,5-cyclohexadienyl or CnF2(n-a)-3(1-b)H2a-3b with n≤30, 0≤a≤n and b=0 or 1;
aryl, saturated or unsaturated heterocyclyl, or 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.

### Claim 15 (depends on 1)

The method of 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−, wherein
Ml+v is selected from the elements of the transition metals,
wherein each individual of the ligands X is independently of each other selected from: fluoride, chloride, bromide, iodide, thiocyanate, dicyanamide, nitrite; nitrate; acetyl acetone; acyl; adenine; 2,2′-azobisisobutyronitrile; alanine; allyl; allyloxycarbonyl; water; aryl; arginine; asparagine; aspartate; BIABN; biotinyl; 2,2′-bis(diphenyl-phosphino)-6,6′-dimethoxy-1,1′-biphenyl; 2,2′-binaphtyldiphenyl-diphosphine; 1,2-bis[4,5-dihydro-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′-e]phosphepine; BINAL; 4,5-dihydro-3H-dinaphtho[2,1-c;1′,2′-e]phosphepine; 2,2′-binaphtyldiol; bis-tert-butyl-bipyridine; benzylmethylphenylphosphine; benzyl; tert-butoxycarbonyl; bis(2-((S)-4-iso-propyl-4,5-dihydrooxazol-2-yl)phenyl)amine; bis(2-((S)-4-tert-butyl-4,5-dihydrooxazol-2-yl)phenyl)amine; 1,2-bis (2,5-diethyl-phospholano)-ethane; butoxy-carbonyl-4-diphenylphosphino-2-diphenylphosphino-methyl-pyrrolidine; 2,2′-bipyridin; benzoyl; benzyloxycarbonyl; CO; cycloheptatrienyl; citrulline; citrate; cyanide; cyclooctadiene; cyclooctatetraene; cyclopentadienyl; pentamethylcyclopentadienyl; cyclohexyl; cytidine; cysteine; cytosine; dibenzilidenacetone; O-isopropylidene-2,3-dihydroxy-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-tetraaza-cyclododecane-1,4,7,10-tetraacetate; diphenylphosphenylethane; diphenylphosphenyl methane; diphenylphosphenyl propane; desoxy ribose; diethylentriamine-pentaacetate; bis(2,5-dimethylphospholano)-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; 3,5-dioxa-4-phosphacyclohepta[2,1-a;3,4-a′]dinapthalene-4-yl)dimethyl amine; methylphenyl-propyl phosphine; methylsulfone; bicyclo[2.2.1]hepta-2,5-; neuraminic acid; N-acetyl-neuraminic acid; N-glycolyl-neuraminic acid; 2,3-bis(diphenylphosphino)-bicyclo[2.2.1]hept-5-ene; nitrilo-triacetic acid; ornithine; succinate; oxalate; phenyl o-anisylmethyl 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.

### Claim 16 (depends on 15)

The method of claim 15, wherein the complex is a complex of the general formula [M+vXv+1]− or [M+vXv+2]2− or [M+vXv+3]3−.

### Claim 17 (depends on 15)

The method of claim 15, wherein M+v is selected from 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.

### Claim 18 (depends on 17)

The method of claim 17, wherein M+v is selected from 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+5, 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.

### Claim 19 (depends on 1)

The method of claim 1, wherein 5-95 wt. % metal salts [M]xb+[B]ya− 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.

### Claim 20 (depends on 19)

The method of claim 19, wherein metal cations of the metal salts 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+, Mg2+, Ca2+, Ba2, Sr2+, Zr4+, Sn2+, Sn4+, Ag+, Zn2+ and Al3+.