# US 11,306,219 B2 · Coatings having repellent function and use thereof

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- Number: US 11,306,219 B2
- Document ID: US11306219B2
- Status: Granted
- Kind: B2
- Application number: 16/466,617
- Filed: 2017-12-21
- Published: 2019-10-24
- Granted: 2022-04-19
- Earliest claimed: 2016-12-29
- Assignees: FundacióN Cidetec
- Applicants: FundacióN Cidetec
- Inventors: Eneko Azaceta Muñoz; Jesús Palenzuela Conde; Ramón Tena Zaera; Estibaliz Medina
- Web page: https://patentgrep.com/patent/US11306219B2

## CPC

- C09D 5/1668: {Vinyl-type polymers}
- C09D 139/04: Homopolymers or copolymers of monomers containing heterocyclic rings having nitrogen as ring member
- C09D 5/00: Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced {(electrically insulating plastics, resins or waxes H01B3/30)}; Filling pastes
- C09D 5/1687: {Use of special additives}
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)

## Abstract

It is provided a coating composition comprising an ionic liquid, and a crosslinked polymeric ionic liquid, wherein the crosslinked polymeric ionic liquid and the ionic liquid are not linked through covalent bonds, and wherein the crosslinked polymeric ionic liquid is linked to a substrate surface. It is also provided a process for its preparation, as well as an article of manufacture at least in part coated with the coating composition as defined above.

## Claims

### Claim 1

A coating composition comprising
an ionic liquid, and
a crosslinked polymeric ionic liquid,
wherein the crosslinked polymeric ionic liquid and the ionic liquid are not linked through covalent bonds, and
wherein the crosslinked polymeric ionic liquid is covalently linked to a substrate surface.

### Claim 2 (depends on 1)

The coating composition of claim 1, wherein the crosslinked polymeric ionic liquid and the ionic liquid are forming an ionogel.

### Claim 3 (depends on 1)

The coating composition of claim 1, wherein the ionic liquid is a compound of formula AaBb, wherein
A is an organic cation comprising at least one omniphobic group,
a is an integer from 1 to 100,
B is an anion with a formula selected from the group consisting of:
wherein
R are the same or different and are selected from the group consisting of —H, —OH, —F, —Cl, —Br, —I, —CN, —NO2, —SO3H, C1-C6 hydroxy alkyl and a completely fluorinated, partially fluorinated or non-fluorinated radical selected from the group consisting of linear or branched C1-C30 alkyl, C1-C30 heteroalkyl, C1-C30 alkoxy, C1-C30 heteroalkoxy C1-C30 alkyl sulfide, C1-C30 heteroalkyl sulfide, C3-C12 cycloalkyl, C1-C12 heterocyclyl, C2-C8 alkenyl, C2-C8 heteroalkenyl, C2-C8 alkynyl, C2-C8 heteroalkynyl, C6-C12 aryl, C1-C12 heteroaryl, alkylaryl, alkylheteroaryl, alkylcyclyl, alkylheterocyclyl, Ph2P(O)—, Ph2P—, (CH3)2P(O)—, (CH3)2P—, Ph2P(S)—, (CH3)2P(S)—, Ph3P═N—, (CH3)3P═N—, FSO2(CH2)n—, CISO2(CH2)n—, HSO3(CH2)n—, HCO2(CH2)n, FSO2NHSO2(CH2)n—, CF3SO2NHSO2(CH2)n—, CnH2n+1 SO2NHSO2(CH2)n—, FSO2(CH2)n—, CISO2(CH2)n—, CnF2n+1 SO2NH(CH2)n—, CH3O—(Si(CH3)2O)n—, HO—(Si(CH3)2O)n—, R—(Si(CH3)2O)n—, wherein n is an integer having a value from 1 to 48; and wherein, optionally, two adjacent substituents R are linked to each other pairwise to form a polycyclic ring system; and
b is the integer defining the stoichiometry necessary to neutralize the positive charge of Aa.

### Claim 4 (depends on 3)

The coating composition of claim 3, wherein A is an organic cation with a formula selected from the group consisting of:
wherein
i) at least one R′ is a completely fluorinated, partially fluorinated or non-fluorinated radical selected from the group consisting of linear or branched C1-C30 alkyl, C1-C30 heteroalkyl, C1-C30 alkoxy, C1-C30 heteroalkoxy C1-C30 alkyl sulfide, C1-C30 heteroalkyl sulfide, C3-C12 cycloalkyl, C1-C12 heterocyclyl, C2-C8 alkenyl, C2-C8 heteroalkenyl, C2-C8 alkynyl, C2-C8 heteroalkynyl, C6-C12 aryl, C1-C12 heteroaryl, alkylaryl, alkylheteroaryl, alkylcyclyl, alkylheterocyclyl, Ph2P(O)—, Ph2P—, (CH3)2P(O)—, (CH3)2P—, Ph2P(S)—, (CH3)2P(S)—, Ph3P═N—, (CH3)3P═N—, FSO2(CH2)n—, CISO2(CH2)n—, HSO3(CH2)n—, HCO2(CH2)n, FSO2NHSO2(CH2)n—, CF3SO2NHSO2(CH2)n—, CnH2n+1 SO2NHSO2(CH2)n—, FSO2(CH2)n—, CISO2(CH2)n—, CnF2n+1 SO2NH(CH2)n—, CH3O—(Si(CH3)2O)n—, HO—(Si(CH3)2O)n—, R—(Si(CH3)2O)n—, wherein n is an integer having a value from 1 to 48;
and wherein, optionally, two adjacent substituents R′ are linked to each other pairwise to form a polycyclic ring system, and
ii) the remaining R′ are the same or different and are selected from the group consisting of —H, —OH, —F, —Cl, —Br, —I, —CN, —NO2, —SO3H, C1-C6 hydroxy alkyl.

### Claim 5 (depends on 4)

The coating composition of claim 4, wherein the at least one R′ is a fluorinated compound with a formula selected from the group consisting of
and —(CH2)n—(CF2)m—CF3, wherein n=0 to 8, and m=(n+1) to (n+12).

### Claim 6 (depends on 1)

The coating composition of claim 1, wherein the crosslinked polymeric ionic liquid is obtainable by polymerizing an ionic liquid crosslinker, and, optionally, an ionic liquid monomer of formula OxBb′, wherein
O is an organic cation comprising an omniphobic group and a polymerizable group,
x is an integer from 1 to 100,
B is an anion with a formula selected from the group consisting of:
wherein
R are the same or different and are selected from the group consisting of —H, —OH, —F, —Cl, —Br, —I, —CN, —NO2, —SO3H, C1-C6 hydroxy alkyl and a completely fluorinated, partially fluorinated or non-fluorinated radical selected from the group consisting of linear or branched C1-C30 alkyl, C1-C30 heteroalkyl, C1-C30 alkoxy, C1-C30 heteroalkoxy C1-C30 alkyl sulfide, C1-C30 heteroalkyl sulfide, C3-C12 cycloalkyl, C1-C12 heterocyclyl, C2-C8 alkenyl, C2-C8 heteroalkenyl, C2-C8 alkynyl, C2-C8 heteroalkynyl, C6-C12 aryl, C1-C12 heteroaryl, alkylaryl, alkylheteroaryl, alkylcyclyl, alkylheterocyclyl, Ph2P(O)—, Ph2P—, (CH3)2P(O)—, (CH3)2P—, Ph2P(S)—, (CH3)2P(S)—, Ph3P═N—, (CH3)3P═N—, FSO2(CH2)n—, CISO2(CH2)n—, HSO3(CH2)n—, HCO2(CH2)n, FSO2NHSO2(CH2)n—, CF3SO2NHSO2(CH2)n—, CnH2n+1 SO2NHSO2(CH2)n—, FSO2(CH2)n—, CISO2(CH2)n—, CnF2n+1 SO2NH(CH2)n—, CH3O—(Si(CH3)2O)n—, HO—(Si(CH3)2O)n—, R—(Si(CH3)2O)n—, wherein n is an integer having a value from 1 to 48; and wherein, optionally, two adjacent substituents R are linked to each other pairwise to form a polycyclic ring system; and b′ is the integer defining the stoichiometry necessary to neutralize the positive charge of Ox;
in the presence of either
i) a solvent system which is a suitable organic solvent, a ionic liquid of formula AaBb, or a mixture thereof, wherein A is an organic cation comprising at least one omniphobic group, a is an integer from 1 to 8, B is as defined above, and b is the integer defining the stoichiometry necessary to neutralize the positive charge of Aa; or alternatively
ii) an ionic liquid of formula AaBb as a lubricant.

### Claim 7 (depends on 6)

The coating composition of claim 6, wherein
O is an organic cation with a formula selected from the group consisting of:
wherein
i) at least one R′ is a completely fluorinated, partially fluorinated or non-fluorinated radical selected from the group consisting of linear or branched C1-C30 alkyl, C1-C30 heteroalkyl, C1-C30 alkoxy, C1-C30 heteroalkoxy C1-C30 alkyl sulfide, C1-C30 heteroalkyl sulfide, C3-C12 cycloalkyl, C1-C12 heterocyclyl, C2-C8 alkenyl, C2-C8 heteroalkenyl, C2-C8 alkynyl, C2-C8 heteroalkynyl, C6-C12 aryl, C1-C12 heteroaryl, alkylaryl, alkylheteroaryl, alkylcyclyl, alkylheterocyclyl, Ph2P(O)—, Ph2P—, (CH3)2P(O)—, (CH3)2P—, Ph2P(S)—, (CH3)2P(S)—, Ph3P═N—, (CH3)3P═N—, FSO2(CH2)n—, CISO2(CH2)n—, HSO3(CH2)n—, HCO2(CH2)n, FSO2NHSO2(CH2)n—, CF3SO2NHSO2(CH2)n—, CnH2n+1 SO2NHSO2(CH2)n—, FSO2(CH2)n—, CISO2(CH2)n—, CnF2n+1 SO2NH(CH2)n—, CH3O—(Si(CH3)2O)n—, HO—(Si(CH3)2O)n—, R—(Si(CH3)2O)n—, wherein n is an integer having a value from 1 to 48; and wherein, optionally, two adjacent substituents R are linked to each other pairwise to form a polycyclic ring system,
ii) at least one R′ is a polymerizable group, and
iii) the remaining R are the same or different and are selected from the group consisting of C1-C30 alkyl, C1-C30 alkoxy, C1-C30 alkyl sulfide, C3-C12 cycloalkyl, C1-C12 heterocyclyl, C2-C8 alkenyl, C2-C8 alkynyl, C6-C12 aryl, C1-C12 heteroaryl, alkylaryl, alkylheteroaryl, alkylcyclyl, alkylheterocyclyl, Ph2P(O)—, Ph2P—, Me2P(O)—, Me2P—, Ph2P(S)—, Me2P(S)—, Ph3P═N—, Me3P═N—, FSO2CF2—, CISO2(CF2)n—, HSO3(CF2)n—, HCO2(CF2)n, FSO2NHSO2(CF2)n—, CF3SO2NHSO2(CF2)n—, CnF2n+1 SO2NHSO2(CF2)n—, FSO2(CF2)n—, CISO2(CF2)n—, CnF2n+1 SO2NH(CF2)n—, —OH, —F, —Cl, —Br, —I, —CN, —NO2, —SO3H and C1-C6 hydroxy alkyl, wherein n is an integer from 1 to 48; and
wherein, optionally, two adjacent substituents R are linked to each other pairwise to form a polycyclic ring system; and
A is an organic cation with a formula selected from the group consisting of:
wherein
i) at least one R′ is a completely fluorinated, partially fluorinated or non-fluorinated radical selected from the group consisting of linear or branched C1-C30 alkyl, C1-C30 heteroalkyl, C1-C30 alkoxy, C1-C30 heteroalkoxy C1-C30 alkyl sulfide, C1-C30 heteroalkyl sulfide, C3-C12 cycloalkyl, C1-C12 heterocyclyl, C2-C8 alkenyl, C2-C8 heteroalkenyl, C2-C8 alkynyl, C2-C8 heteroalkynyl, C6-C12 aryl, C1-C12 heteroaryl, alkylaryl, alkylheteroaryl, alkylcyclyl, alkylheterocyclyl, Ph2P(O)—, Ph2P—, (CH3)2P(O)—,
wherein
i) at least one R″ is a polymerizable group, and
ii) a R″ of one of the two Q organic cations and a R″ of the other Q organic cation are linked together and are defining a group X,
wherein, X is a birradical selected from the group consisting of: (C1-C20)alkyl; (C1-C20)alkyl substituted with one or more radicals independently selected from the group consisting of: (C1-C5)alkyl, —OH, halogen, phenyl, phenyl substituted with one or more (C1-C4)alkyl radicals, phenyl substituted with one or more halogen radicals, benzyl, benzyl substituted with one or more (C1-C4)alkyl radicals, benzyl substituted with one or more halogen radicals, —C(═O)R3, —C(═O)(R7), —OC(═O)(O)R3, —C(═O)(O−), —C(═O)(O)R3, —OR3, —CH(OR3)(OR4), —C(OR3)(OR4)(R5), —C(OR3)(OR4)(OR5), —C(OR3)(OR4)(OR5)(OR6), —NR1R2, —N+R1R2R3, —C(═NR1)(R2), —C(═O)(NR1R2), —N(C(═O)(R1)) (C(═O)(R2))(R3), —O(CN), —NC(═O), —ONO2, —CN, —NC, —ON(═O), —NO2, —NO, —C5H4N, —SR1, SSR1, —S(═O)(R1), —S(═O)(═O)(R1), —S(═O)(OH), —S(═O)(═O)(OH), —SCN, —NCS, —C(═S)(R1), —PR1R2, —P(═O)(OH)2, —OP(═O)(OH)2, —OP(═O)(OR1)(OR2), —B(OH), —B(OR1)(OR2) and —B(OR1)(R2), wherein R1, R2, R3, R4, R5, and R6 are radicals independently selected from the group consisting of H, (C1-C20)alkyl, (C5-C12)aryl(C1-C20)alkyl, and (C5-C12)aryl; and R7 is halogen;
a 2 to 20-member heteroalkyl; a 2 to 20-member heteroalkyl substituted with one or more radicals independently selected from the group consisting of: —OH, halogen, phenyl, phenyl substituted with one or more (C1-C4)alkyl radicals, phenyl substituted with one or more halogen radicals, benzyl, benzyl substituted with one or more (C1-C4)alkyl radicals, benzyl substituted with one or more halogen radicals, (CH3)2P—, Ph2P(S)—, (CH3)2P(S)—, Ph3P═N—, (CH3)3P═N—, FSO2(CH2)n—, CISO2(CH2)n—, HSO3(CH2)n—, HCO2(CH2)n, FSO2NHSO2(CH2)n—, CF3SO2NHSO2(CH2)n—, CnH2n+1 SO2NHSO2(CH2)n—, FSO2(CH2)n—, CISO2(CH2)n—, CnF2n+1 SO2NH(CH2)n—, CH3O—(Si(CH3)2O)n—, HO—(Si(CH3)2O)n—, R—(Si(CH3)2O)n—, wherein n is an integer having a value from 1 to 48; and wherein, optionally, two adjacent substituents R are linked to each other pairwise to form a polycyclic ring system, and
ii) the remaining R′ are the same or different and are selected from the group consisting of —H, —OH, —F, —Cl, —Br, —I, —CN, —NO2, —SO3H, C1-C6 hydroxy alkyl.

### Claim 8 (depends on 7)

The coating composition of claim 7, wherein the omniphobic R′ group is a fluorinated compound with a formula selected from the group consisting of
and —(CH2)n—(CF2)m—CF3, wherein n=0 to 8, and m=(n+1) to (n+12).

### Claim 9 (depends on 6)

The coating composition of claim 6, wherein the polymerizable group is either independently selected from the group consisting of a vinyl, an acrylic, a methacrylic, and an allyl group, or alternatively, independently selected from the group consisting of —OH, —SH, —NH2, —COOH, —C(═O)X, ester, anhydride, —NCO, —NCS, and epoxy, provided an ether, thioether, amido, ester, urethane, tiourethane, urea, or thioruea type chemical bond is obtained.

### Claim 10 (depends on 6)

The coating composition of claim 6, wherein
the ionic liquid crosslinker is a compound of formula SsQq-X-QqSs, wherein
Q is an organic cation independently selected from the group consisting of: —C(═O)R3, —C(═O)(R7), —OC(═O)(O)R3, —C(═O)(0-), —C(═O)(O)R3, —OR3, —CH(OR3)(OR4), —C(OR3)(OR4)(R5), —C(OR3)(OR4)(OR5), —C(OR3)(OR4)(OR5)(OR6), —NR1R2, —N+R1R2R3, —C(═NR1)(R2), —C(═O)(NR1R2), —N(C(═O)(R1)) (C(═O)(R2))(R3), —O(CN), —NC(═O), —ONO2, —CN, —NC, —ON(═O), —NO2, —NO, —C5H4N, —SR1, —SSR1, —S(═O)(R1), —S(═O)(═O)(R1), —S(═O)(OH), —S(═O)(═O)(OH), —SCN, —NCS, —C(═S)(R1), —PR1R2, —P(═O)(OH)2, —OP(═O)(OH)2, —OP(═O)(OR1)(OR2), —B(OH), —B(OR1)(OR2) and —B(OR1)(R2), wherein R1, R2, R3, R4, R5, R6, and R7 are as defined above; and a homopolymer or copolymer comprising a polymeric chain selected from the group consisting of: alkyd resin, epoxy resin, phenolic resin, polyvinyl halides, polyacetal, polyacrylics, polyalkylenes, polyalkenylenes, polyalkynylenes, polyamic acids, polyamides, polyamines, polyanhydrides, polyarylenealkylenes, polyarylenes, polyazomethines, polybenzimidazoles, polybenzothiazoles, polybenzyls, polycarbodiimides, polycarbonates, polycarbones, polycarboranes, polycarbosilanes, polycyanurates, polydienes, polyester-polyurethanes, polyesters, polyetheretherketones, polyether-polyurethanes, polyethers, polyhydrazides, polyimidazoles, polyimides, polyisocyanurates, polyketones, polyolefines, polyoxyalkylenes, polyoxyphenylenes, polyphenyls, polyphosphazenes, polypyrroles, polypyrrones, polyquinolines, polyquinoxalines, polysilanes, polysilazanes, polysiloxanes, polysilsesquioxanes, polysulfides, polysulfonamides, polysulfones, polythiazoles, polythiomethylenes, polythiophenylenes, polyureas, polyurethanes, polyvinyl acetals, polyvinyl butyrals, polyvinyl formals, polyvinyl alkanoates, vinyl polymers, and natural polymers; and
iii) the remaining R″ are the same or different and are selected from the group consisting of H, C1-C30 alkyl, C1-C30 alkyl substituted with one or more F, C6-C12 aryl, C6-C12 aryl substituted with one or more F;
q is an integer from 1 to 100,
S is an anion with a formula selected from the group consisting of:
wherein
R are the same or different and are selected from the group consisting of —H, —OH, —F, —Cl, —Br, —I, —CN, —NO2, —SO3H, C1-C6 hydroxy alkyl and a completely fluorinated, partially fluorinated or non-fluorinated radical selected from the group consisting of linear or branched C1-C30 alkyl, C1-C30 heteroalkyl, C1-C30 alkoxy, C1-C30 heteroalkoxy C1-C30 alkyl sulfide, C1-C30 heteroalkyl sulfide, C3-C12 cycloalkyl, C1-C12 heterocyclyl, C2-C8 alkenyl, C2-C8 heteroalkenyl, C2-C8 alkynyl, C2-C8 heteroalkynyl, C6-C12 aryl, C1-C12 heteroaryl, alkylaryl, alkylheteroaryl, alkylcyclyl, alkylheterocyclyl, Ph2P(O)—, Ph2P—, (CH3)2P(O)—, (CH3)2P—, Ph2P(S)—, (CH3)2P(S)—, Ph3P═N—, (CH3)3P═N—, FSO2(CH2)n—, CISO2(CH2)n—, HSO3(CH2)n—, HCO2(CH2)n, FSO2NHSO2(CH2)n—, CF3SO2NHSO2(CH2)n—, CnH2n+1 SO2NHSO2(CH2)n—, FSO2(CH2)n—, CISO2(CH2)n—, CnF2n+1 SO2NH(CH2)n—, CH3O—(Si(CH3)2O)n—, HO—(Si(CH3)2O)n—, R—(Si(CH3)2O)n—, wherein n is an integer having a value from 1 to 48; and wherein, optionally, two adjacent substituents R are linked to each other pairwise to form a polycyclic ring system; and
s is an integer indicating the stoichiometry necessary to neutralize the positive charge of Qq.

### Claim 11 (depends on 1)

A process for the preparation of a coating composition as defined in claim 1, over at least part of the surface of a substrate, the process comprising:
a) functionalising at least part of the surface of the substrate;
b) mixing
an ionic liquid crosslinker,
a solvent system which is a suitable organic solvent, or a non-polymerizable ionic liquid of formula AaBb, wherein
A is an organic cation comprising at least one omniphobic group,
a is an integer from 1 to 100,
B is an anion with a formula selected from the group consisting of:
wherein
R are the same or different and are selected from the group consisting of —H, —OH, —F, —Cl, —Br, —I, —CN, —NO2, —SO3H, C1-C6 hydroxy alkyl and a completely fluorinated, partially fluorinated or non-fluorinated radical selected from the group consisting of linear or branched C1-C30 alkyl, C1-C30 heteroalkyl, C1-C30 alkoxy, C1-C30 heteroalkoxy C1-C30 alkyl sulfide, C1-C30 heteroalkyl sulfide, C3-C12 cycloalkyl, C1-C12 heterocyclyl, C2-C8 alkenyl, C2-C8 heteroalkenyl, C2-C8 alkynyl, C2-C8 heteroalkynyl, C6-C12 aryl, C1-C12 heteroaryl, alkylaryl, alkylheteroaryl, alkylcyclyl, alkylheterocyclyl, Ph2P(O)—, Ph2P—, (CH3)2P(O)—, (CH3)2P—, Ph2P(S)—, (CH3)2P(S)—, Ph3P═N—, (CH3)3P═N—, FSO2(CH2)n—, CISO2(CH2)n—, HSO3(CH2)n—, HCO2(CH2)n, FSO2NHSO2(CH2)n—, CF3SO2NHSO2(CH2)n—, CnH2n+1 SO2NHSO2(CH2)n—, FSO2(CH2)n—, CISO2(CH2)n—, CnF2n+1 SO2NH(CH2)n—, CH3O—(Si(CH3)2O)n—, HO—(Si(CH3)2O)n—, R—(Si(CH3)2O)n—, wherein n is an integer having a value from 1 to 48; and wherein, optionally, two adjacent substituents R are linked to each other pairwise to form a polycyclic ring system; and b′ is the integer defining the stoichiometry necessary to neutralize the positive charge of Ox, and
b is the integer defining the stoichiometry necessary to neutralize the positive charge of Aa; and
optionally, an ionic liquid monomer, wherein
c) at least partially coating the surface functionalised in step a) with the mixture prepared in step b);
d) carrying out a polymerization and crosslinking reaction of the coated surface of step c),
e) removing the solvent system used in step b); and
f) spreading over the coated surface of the substrate obtained in step d) an ionic liquid as a lubricant.

### Claim 12 (depends on 11)

The process of claim 11, wherein the amount of ionic liquid monomer is from 0 to 99.89 wt %, from 0.01 to 50 wt %, from 0.2 to 50 wt %, or from 0.5 to 17 wt %, with respect to the total weight of the mixture of ionic liquid crosslinker, solvent system, and ionic liquid monomer.

### Claim 13 (depends on 11)

The process of claim 11, wherein the amount of ionic liquid crosslinker is from 0.1 to 99.99 wt %, from 0.5 to 90 wt %, from 1 to 80 wt %, of from 3 to 20 wt % with respect to the total weight of the mixture of ionic liquid crosslinker, solvent system, and ionic liquid monomer.

### Claim 14 (depends on 1)

A process for the preparation of a coating composition as defined in claim 1, over at least part of the surface of a substrate, the process comprising:
a) functionalising at least part of the surface of the substrate;
b) mixing
an ionic liquid crosslinker,
an ionic liquid as a lubricant, and
optionally, an ionic liquid monomer;
c) at least partially coating the surface functionalised in step a) with the mixture prepared in step b);
d) carrying out a polymerization and crosslinking reaction of the coated surface.

### Claim 15 (depends on 1)

An article of manufacture coated with the coating composition of claim 1.

### Claim 16 (depends on 2)

The coating composition of claim 2, wherein the ionic liquid is a compound of formula AaBb, wherein
A is an organic cation comprising at least one omniphobic group,
a is an integer from 1 to 100,
B is an anion with a formula selected from the group consisting of:
wherein
R are the same or different and are selected from the group consisting of —H, —OH, —F, —Cl, —Br, —I, —CN, —NO2, —SO3H, C1-C6 hydroxy alkyl and a completely fluorinated, partially fluorinated or non-fluorinated radical selected from the group consisting of linear or branched C1-C30 alkyl, C1-C30 heteroalkyl, C1-C30 alkoxy, C1-C30 heteroalkoxy C1-C30 alkyl sulfide, C1-C30 heteroalkyl sulfide, C3-C12 cycloalkyl, C1-C12 heterocyclyl, C2-C8 alkenyl, C2-C8 heteroalkenyl, C2-C8 alkynyl, C2-C8 heteroalkynyl, C6-C12 aryl, C1-C12 heteroaryl, alkylaryl, alkylheteroaryl, alkylcyclyl, alkylheterocyclyl, Ph2P(O)—, Ph2P—, (CH3)2P(O)—, (CH3)2P—, Ph2P(S)—, (CH3)2P(S)—, Ph3P═N—, (CH3)3P═N—, FSO2(CH2)n—, CISO2(CH2)n—, HSO3(CH2)n—, HCO2(CH2)n, FSO2NHSO2(CH2)n—, CF3SO2NHSO2(CH2)n—, CnH2n+1 SO2NHSO2(CH2)n—, FSO2(CH2)n—, CISO2(CH2)n—, CnF2n+1 SO2NH(CH2)n—, CH3O—(Si(CH3)2O)n—, HO—(Si(CH3)2O)n—, R—(Si(CH3)2O)n—, wherein n is an integer having a value from 1 to 48; and wherein, optionally, two adjacent substituents R are linked to each other pairwise to form a polycyclic ring system; and
b is the integer defining the stoichiometry necessary to neutralize the positive charge of Aa.

### Claim 17 (depends on 16)

The coating composition of claim 16, wherein A is an organic cation with a formula selected from the group consisting of:
wherein
i) at least one R′ is a completely fluorinated, partially fluorinated or non-fluorinated radical selected from the group consisting of linear or branched C1-C30 alkyl, C1-C30 heteroalkyl, C1-C30 alkoxy, C1-C30 heteroalkoxy C1-C30 alkyl sulfide, C1-C30 heteroalkyl sulfide, C3-C12 cycloalkyl, C1-C12 heterocyclyl, C2-C8 alkenyl, C2-C8 heteroalkenyl, C2-C8 alkynyl, C2-C8 heteroalkynyl, C6-C12 aryl, C1-C12 heteroaryl, alkylaryl, alkylheteroaryl, alkylcyclyl, alkylheterocyclyl, Ph2P(O)—, Ph2P—, (CH3)2P(O)—, (CH3)2P—, Ph2P(S)—, (CH3)2P(S)—, Ph3P═N—, (CH3)3P═N—, FSO2(CH2)n—, CISO2(CH2)n—, HSO3(CH2)n—, HCO2(CH2)n, FSO2NHSO2(CH2)n—, CF3SO2NHSO2(CH2)n—, CnH2n+1 SO2NHSO2(CH2)n—, FSO2(CH2)n—, CISO2(CH2)n—, CnF2n+1 SO2NH(CH2)n—, CH3O—(Si(CH3)2O)n—, HO—(Si(CH3)2O)n—, R—(Si(CH3)2O)n—, wherein n is an integer having a value from 1 to 48; and wherein, optionally, two adjacent substituents R′ are linked to each other pairwise to form a polycyclic ring system, and
ii) the remaining R′ are the same or different and are selected from the group consisting of —H, —OH, —F, —Cl, —Br, —I, —CN, —NO2, —SO3H, C1-C6 hydroxy alkyl.

### Claim 18 (depends on 17)

The coating composition of claim 17, wherein the at least one R′ is a fluorinated compound with a formula selected from the group consisting of
and —(CH2)n—(CF2)m—CF3, wherein n=0 to 8, and m=(n+1) to (n+12).

### Claim 19 (depends on 16)

The coating composition of claim 16, wherein the crosslinked polymeric ionic liquid is obtainable by polymerizing an ionic liquid crosslinker, and, optionally, an ionic liquid monomer of formula OxBb′, wherein
O is an organic cation comprising an omniphobic group and a polymerizable group,
x is an integer from 1 to 100,
B is an anion with a formula selected from the group consisting of:
wherein
R are the same or different and are selected from the group consisting of —H, —OH, —F, —Cl, —Br, —I, —CN, —NO2, —SO3H, C1-C6 hydroxy alkyl and a completely fluorinated, partially fluorinated or non-fluorinated radical selected from the group consisting of linear or branched C1-C30 alkyl, C1-C30 heteroalkyl, C1-C30 alkoxy, C1-C30 heteroalkoxy C1-C30 alkyl sulfide, C1-C30 heteroalkyl sulfide, C3-C12 cycloalkyl, C1-C12 heterocyclyl, C2-C8 alkenyl, C2-C8 heteroalkenyl, C2-C8 alkynyl, C2-C8 heteroalkynyl, C6-C12 aryl, C1-C12 heteroaryl, alkylaryl, alkylheteroaryl, alkylcyclyl, alkylheterocyclyl, Ph2P(O)—, Ph2P—, (CH3)2P(O)—, (CH3)2P—, Ph2P(S)—, (CH3)2P(S)—, Ph3P═N—, (CH3)3P═N—, FSO2(CH2)n—, CISO2(CH2)n—, HSO3(CH2)n—, HCO2(CH2)n, FSO2NHSO2(CH2)n—, CF3SO2NHSO2(CH2)n—, CnH2n+1 SO2NHSO2(CH2)n—, FSO2(CH2)n—, CISO2(CH2)n—, CnF2n+1 SO2NH(CH2)n—, CH3O—(Si(CH3)2O)n—, HO—(Si(CH3)2O)n—, R—(Si(CH3)2O)n—, wherein n is an integer having a value from 1 to 48; and wherein, optionally, two adjacent substituents R are linked to each other pairwise to form a polycyclic ring system; and b′ is the integer defining the stoichiometry necessary to neutralize the positive charge of Ox;
in the presence of either
i) a solvent system which is a suitable organic solvent, a ionic liquid of formula AaBb, or a mixture thereof, wherein A is an organic cation comprising at least one omniphobic group, a is an integer from 1 to 8, B is as defined above, and b is the integer defining the stoichiometry necessary to neutralize the positive charge of Aa; or alternatively
ii) an ionic liquid of formula AaBb as a lubricant.

### Claim 20 (depends on 19)

The coating composition of claim 19, wherein
O is an organic cation with a formula selected from the group consisting of:
wherein
i) at least one R′ is a completely fluorinated, partially fluorinated or non-fluorinated radical selected from the group consisting of linear or branched C1-C30 alkyl, C1-C30 heteroalkyl, C1-C30 alkoxy, C1-C30 heteroalkoxy C1-C30 alkyl sulfide, C1-C30 heteroalkyl sulfide, C3-C12 cycloalkyl, C1-C12 heterocyclyl, C2-C8 alkenyl, C2-C8 heteroalkenyl, C2-C8 alkynyl, C2-C8 heteroalkynyl, C6-C12 aryl, C1-C12 heteroaryl, alkylaryl, alkylheteroaryl, alkylcyclyl, alkylheterocyclyl, Ph2P(O)—, Ph2P—, (CH3)2P(O)—, (CH3)2P—, Ph2P(S)—, (CH3)2P(S)—, Ph3P═N—, (CH3)3P═N—, FSO2(CH2)n—, CISO2(CH2)n—, HSO3(CH2)n—, HCO2(CH2)n, FSO2NHSO2(CH2)n—, CF3SO2NHSO2(CH2)n—, CnH2n+1 SO2NHSO2(CH2)n—, FSO2(CH2)n—, CISO2(CH2)n—, CnF2n+1 SO2NH(CH2)n—, CH3O—(Si(CH3)2O)n—, HO—(Si(CH3)2O)n—, R—(Si(CH3)2O)n—, wherein n is an integer having a value from 1 to 48; and wherein, optionally, two adjacent substituents R are linked to each other pairwise to form a polycyclic ring system,
ii) at least one R′ is a polymerizable group, and
iii) the remaining R are the same or different and are selected from the group consisting of C1-C30 alkyl, C1-C30 alkoxy, C1-C30 alkyl sulfide, C3-C12 cycloalkyl, C1-C12 heterocyclyl, C2-C8 alkenyl, C2-C8 alkynyl, C6-C12 aryl, C1-C12 heteroaryl, alkylaryl, alkylheteroaryl, alkylcyclyl, alkylheterocyclyl, Ph2P(O)—, Ph2P—, Me2P(O)—, Me2P—, Ph2P(S)—, Me2P(S)—, Ph3P═N—, Me3P═N—, FSO2CF2—, CISO2(CF2)n—, HSO3(CF2)n—, HCO2(CF2)n, FSO2NHSO2(CF2)n—, CF3SO2NHSO2(CF2)n—, CnF2n+1 SO2NHSO2(CF2)n—, FSO2(CF2)n—, CISO2(CF2)n—, CnF2n+1 SO2NH(CF2)n—, —OH, —F, —Cl, —Br, —I, —CN, —NO2, —SO3H and C1-C6 hydroxy alkyl, wherein n is an integer from 1 to 48; and
wherein, optionally, two adjacent substituents R are linked to each other pairwise to form a polycyclic ring system; and
A is an organic cation with a formula selected from the group consisting of:
wherein
i) at least one R′ is a completely fluorinated, partially fluorinated or non-fluorinated radical selected from the group consisting of linear or branched C1-C30 alkyl, C1-C30 heteroalkyl, C1-C30 alkoxy, C1-C30 heteroalkoxy C1-C30 alkyl sulfide, C1-C30 heteroalkyl sulfide, C3-C12 cycloalkyl, C1-C12 heterocyclyl, C2-C8 alkenyl, C2-C8 heteroalkenyl, C2-C8 alkynyl, C2-C8 heteroalkynyl, C6-C12 aryl, C1-C12 heteroaryl, alkylaryl, alkylheteroaryl, alkylcyclyl, alkylheterocyclyl, Ph2P(O)—, Ph2P—, (CH3)2P(O)—, (CH3)2P—, Ph2P(S)—, (CH3)2P(S)—, Ph3P═N—, (CH3)3P═N—, FSO2(CH2)n—, CISO2(CH2)n—, HSO3(CH2)n—, HCO2(CH2)n, FSO2NHSO2(CH2)n—, CF3SO2NHSO2(CH2)n—, CnH2n+1 SO2NHSO2(CH2)n—, FSO2(CH2)n—, CISO2(CH2)n—, CnF2n+1 SO2NH(CH2)n—, CH3O—(Si(CH3)2O)n—, HO—(Si(CH3)2O)n—, R—(Si(CH3)2O)n—, wherein n is an integer having a value from 1 to 48; and wherein, optionally, two adjacent substituents R are linked to each other pairwise to form a polycyclic ring system, and
ii) the remaining R′ are the same or different and are selected from the group consisting of —H, —OH, —F, —Cl, —Br, —I, —CN, —NO2, —SO3H, C1-C6 hydroxy alkyl;
wherein the polymerizable group is either independently selected from the group consisting of a vinyl, an acrylic, a methacrylic, and an allyl group, or alternatively, independently selected from the group consisting of —OH, —SH, —NH2, —COOH, —C(═O)X, ester, anhydride, —NCO, —NCS, and epoxy, provided an ether, thioether, amido, ester, urethane, tiourethane, urea, or thioruea type chemical bond is obtained.