# US 2014/0151607 A1 · Ultraviolet-Curable Conductive Ink and Dielectric Ink Compositions Having a Common Binding Medium, with Manufactures and Fabrication Methods

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- Number: US 2014/0151607 A1
- Document ID: US20140151607A1
- Status: Published application
- Kind: A1
- Application number: 14/086,831
- Filed: 2013-11-21
- Published: 2014-06-05
- Earliest claimed: 2012-11-30
- Applicants: NthDegree Technologies Worldwide Inc.
- Inventors: Mark David Lowenthal; Mark Lewandowski; Alexandra Elyse Hartman
- Web page: https://patentgrep.com/patent/US20140151607A1

## CPC

- C09D 11/52: Electrically conductive inks
- C09D 11/101: Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
- 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

Compositions, methods and manufactures are disclosed for an ultraviolet-curable conductive ink and for a binding medium which may be utilized for both a dielectric ink and for a conductive ink. A representative ultraviolet-curable binding medium composition comprises: a difunctional aliphatic polycarbonate urethane acrylate oligomer; a monofunctional monomer such as an isophoryl acrylate monomer or an acrylate ester monomer; a difunctional monomer such as a difunctional alkoxylated acrylate or methacrylate monomer; a first photoinitiator such as an α-hydroxyketone class photoinitiator; and a second photoiniator such as an α-aminoketone class photoinitiator. A plurality of conductive particles, such as silver particles and graphene particles, may be included in the binding medium to provide an ultraviolet-curable conductive ink and, when cured, a conductive layer or wire, for example.

## Claims

### Claim 1

A composition for an ultraviolet-curable binding medium which may be utilized for a dielectric ink and for a conductive ink, the composition comprising:
a difunctional aliphatic polycarbonate urethane acrylate oligomer;
a monofunctional acrylate monomer selected from the group consisting of: an isophoryl acrylate monomer, an acrylate ester monomer, a 3,3,5 trimethyl cyclohexanol acrylate monomer, and mixtures thereof;
a difunctional acrylate monomer selected from the group consisting of: a difunctional alkoxylated acrylate monomer, a difunctional methacrylate monomer, an alkoxylated hexandiol acrylate monomer, a 1,6-hexandiol diacrylate monomer, and mixtures thereof;
a first photoinitiator comprising an α-hydroxyketone class photoinitiator;
a second photoiniator different from the first photoinitiator and comprising an α-aminoketone class photoinitiator; and
a wetting, flow and/or leveling promoter comprising one or more copolymers of ethyl acrylate and 2-ethylhexyl acrylate.

### Claim 2 (depends on 1)

The composition of claim 1, wherein:
the difunctional aliphatic polycarbonate urethane acrylate oligomer is present in an amount between about 47.5% to 52.5% by weight;
the monofunctional acrylate monomer is present in an amount between about 27.5% to 32.5% by weight;
the difunctional acrylate monomer is present in an amount between about 3.0% to 6.0% by weight;
the first photoinitiator is present in an amount between about 9.0% to 11.0% by weight;
the second photoiniator is present in an amount between about 4.0% to 6.0% by weight; and
the wetting, flow and/or leveling promoter is present in an amount between about 0.7% to 1.5% by weight.

### Claim 3 (depends on 2)

An insulating layer, film or trace formed from ultraviolet and thermal curing of the composition of claim 2.

### Claim 4 (depends on 1)

The composition of claim 1, further comprising:
a plurality of conductive particles comprising a mixture of graphene particles and either or both silver particles or silver coated copper particles.

### Claim 5 (depends on 1)

The composition of claim 1, further comprising:
a plurality of conductive particles present in an amount between about 77.5% to 82.5% by weight and comprising silver particles and graphene particles; and wherein:
the difunctional aliphatic polycarbonate urethane acrylate oligomer is present in an amount between about 9.5% to 10.5% by weight;
the monofunctional acrylate monomer is present in an amount between about 5.5% to 6.5% by weight;
the difunctional acrylate monomer is present in an amount between about 0.6% to 1.2% by weight;
the first photoinitiator is present in an amount between about 1.8% to 2.2% by weight;
the second photoiniator is present in an amount between about 0.8% to 1.2% by weight; and
the wetting, flow and/or leveling promoter is present in an amount between about 0.14% to 0.3% by weight.

### Claim 6 (depends on 5)

The composition of claim 5, wherein the graphene particles are present in an amount between about 0.20% to 0.30% by weight.

### Claim 7 (depends on 5)

The composition of claim 5, wherein the graphene particles are present in an amount of about 0.25% by weight.

### Claim 8 (depends on 5)

A method of manufacturing the composition of claim 5, comprising:
mixing the first and second photoinitiators with the monofunctional acrylate monomer to form a photoinitiator monofunctional acrylate monomer mixture;
mixing the difunctional aliphatic polycarbonate urethane acrylate oligomer and the monofunctional acrylate monomer to form an oligomer and monomer mixture;
mixing the photoinitiator monofunctional acrylate monomer mixture with the oligomer and monomer mixture;
adjusting any weight percentages of the monofunctional acrylate monomer and difunctional aliphatic polycarbonate urethane acrylate oligomer;
adding and mixing the difunctional acrylate monomer and the wetting, flow and/or leveling promoter or promotion agent;
adding and mixing the silver particles; and
adding and mixing the graphene particles.

### Claim 9 (depends on 5)

A conductive layer, film or trace formed from ultraviolet and thermal curing of the composition of claim 5.

### Claim 10 (depends on 1)

The composition of claim 1, further comprising a thermal initiator, and wherein the first photoinitiator, the second photoiniator and the thermal initiator are selected from the group consisting of: 1,1-bis(tert-butylperoxy)-3,3,5-trimethylcyclohexane, 1,1′-azobis(cyclohexanecarbonitrile), benzoyl peroxide, tert-butyl peroxy-2 ethylhexanoate, 1,1-Di(tert-butylperoxy)-3,3,5-trimethylcyclohexane, α-hydroxyketones, phenylglyoxylates, benzyldimethyl-ketals, α-aminoketones, mono acyl phosphines, bis acyl phosphines, phosphine oxides, metallocenes, iodonium salts, and mixtures thereof.

### Claim 11 (depends on 1)

The composition of claim 1, further comprising at least one solvent selected from the group consisting of: water; alcohols; cyclic alcohols; lactones; cyclic ketones; glycols; glycerols; carboxylic acids; dicarboxylic acids; tricarboxylic acids; alkyl carboxylic acids; benzene derivatives; butane derivatives; and mixtures thereof.

### Claim 12 (depends on 1)

The composition of claim 1, further comprising a viscosity or rheology modifier selected from the group consisting of: acrylate and (meth)acrylate polymers, copolymers, polymeric precursors or polymerizable precursors; fumed silica, silica powders; and mixtures thereof.

### Claim 13

A composition for an ultraviolet-curable binding medium which may be utilized for a dielectric ink and for a conductive ink, the composition comprising:
a difunctional oligomer comprising a difunctional aliphatic polycarbonate urethane acrylate oligomer;
a monofunctional monomer selected from the group consisting of: urethane monomers, acrylate monomers, epoxy monomers, vinyl monomers, vinyl-ether monomers, polyester monomers, and mixtures thereof;
a difunctional or trifunctional monomer selected from the group consisting of: urethane monomers, acrylate monomers, epoxy monomers, vinyl monomers, vinyl-ether monomers, polyester monomers, and mixtures thereof;
a first photoinitiator; and
a second photoiniator different from the first photoinitiator.

### Claim 14 (depends on 13)

The composition of claim 13, wherein the monofunctional monomer is a monofunctional acrylate monomer.

### Claim 15 (depends on 13)

The composition of claim 13, wherein the monofunctional monomer is selected from the group consisting of: an isophoryl acrylate monomer, an acrylate ester monomer, a 3,3,5 trimethyl cyclohexanol acrylate monomer, vinyl pyrollidone, vinyl caprolactam, and mixtures thereof.

### Claim 16 (depends on 13)

The composition of claim 13, wherein the difunctional monomer is a difunctional acrylate monomer.

### Claim 17 (depends on 13)

The composition of claim 13, wherein the difunctional or trifunctional monomer is selected from the group consisting of: a difunctional alkoxylated acrylate monomer, a difunctional methacrylate monomer, an alkoxylated hexandiol acrylate monomer, a 1,6-hexandiol diacrylate monomer, and mixtures thereof.

### Claim 18 (depends on 13)

The composition of claim 13, further comprising:
a wetting, flow and/or leveling promoter or promotion agent comprising an acrylate copolymer.

### Claim 19 (depends on 18)

The composition of claim 18, wherein the wetting, flow and/or leveling promoter or promotion agent is one or more copolymers of ethyl acrylate and 2-ethylhexyl acrylate.

### Claim 20 (depends on 13)

The composition of claim 13, further comprising a thermal initiator, and wherein the first photoinitiator, the second photoiniator and the thermal initiator are selected from the group consisting of: 1,1-bis(tert-butylperoxy)-3,3,5-trimethylcyclohexane, 1,1′-azobis(cyclohexanecarbonitrile), benzoyl peroxide, tert-butyl peroxy-2 ethylhexanoate, 1,1-Di(tert-butylperoxy)-3,3,5-trimethylcyclohexane, α-hydroxyketones, phenylglyoxylates, benzyldimethyl-ketals, α-aminoketones, mono acyl phosphines, bis acyl phosphines, phosphine oxides, metallocenes, iodonium salts, and mixtures thereof.

### Claim 21 (depends on 13)

The composition of claim 13, wherein:
the difunctional aliphatic polycarbonate urethane acrylate oligomer is present in an amount between about 47.5% to 52.5% by weight;
the monofunctional monomer is present in an amount between about 27.5% to 32.5% by weight and comprises a monofunctional acrylate monomer selected from the group consisting of: an isophoryl acrylate monomer, an acrylate ester monomer, a 3,3,5 trimethyl cyclohexanol acrylate monomer, and mixtures thereof;
the difunctional or trifunctional monomer is present in an amount between about 3.0% to 6.0% by weight and comprises a difunctional acrylate monomer selected from the group consisting of: a difunctional alkoxylated acrylate monomer, a difunctional methacrylate monomer, an alkoxylated hexandiol acrylate monomer, a 1,6-hexandiol diacrylate monomer, and mixtures thereof;
the first photoinitiator is present in an amount between about 9.0% to 11.0% by weight and comprises an α-hydroxyketone class photoinitiator; and
the second photoiniator is present in an amount between about 4.0% to 6.0% by weight and comprises an α-aminoketone class photoinitiator.

### Claim 22 (depends on 13)

The composition of claim 13, further comprising:
a plurality of conductive particles to form a conductive ink, wherein the plurality of conductive particles comprise at least one conductor selected from the group consisting of: aluminum, copper, silver, gold, nickel, palladium, tin, platinum, lead, zinc, graphene, alloys thereof, and mixtures thereof.

### Claim 23 (depends on 22)

The composition of claim 22, wherein the plurality of conductive particles comprise a mixture of graphene particles and either or both silver particles or silver coated copper particles.

### Claim 24 (depends on 13)

The composition of claim 13, further comprising:
a plurality of conductive particles present in an amount between about 77.5% to 82.5% by weight and comprising silver particles and graphene particles; and
a wetting, flow and/or leveling promoter or promotion agent present in an amount in the binding medium between about 0.14% to 0.3% by weight and comprising a polymer or copolymer of ethyl acrylate or 2-ethylhexyl acrylate;
wherein:
the difunctional aliphatic polycarbonate urethane acrylate oligomer is present in an amount between about 9.5% to 10.5% by weight;
the monofunctional monomer is present in an amount between about 5.5% to 6.5% by weight and comprises a monofunctional acrylate monomer selected from the group consisting of: an isophoryl acrylate monomer, an acrylate ester monomer, a 3,3,5 trimethyl cyclohexanol acrylate monomer, and mixtures thereof;
the difunctional or trifunctional monomer is present in an amount between about 0.6% to 1.2% by weight and comprises a difunctional acrylate monomer selected from the group consisting of: a difunctional alkoxylated acrylate monomer, a difunctional methacrylate monomer, an alkoxylated hexandiol acrylate monomer, a 1,6-hexandiol diacrylate monomer, and mixtures thereof;
the first photoinitiator is present in an amount between about 1.8% to 2.2% by weight and comprises an α-hydroxyketone class photoinitiator; and
the second photoiniator is present in an amount between about 0.8% to 1.2% by weight and comprises an α-aminoketone class photoinitiator.

### Claim 25 (depends on 24)

The composition of claim 24, wherein the graphene particles are present in an amount between about 0.20% to 0.30% by weight.

### Claim 26

A composition for an ultraviolet-curable binding medium which may be utilized for a dielectric ink and for a conductive ink, the composition comprising:
a difunctional aliphatic polycarbonate urethane acrylate oligomer present in an amount between about 47.5% to 52.5% by weight;
a monofunctional acrylate monomer present in an amount between about 27.5% to 32.5% by weight and selected from the group consisting of: an isophoryl acrylate monomer, an acrylate ester monomer, a 3,3,5 trimethyl cyclohexanol acrylate monomer, and mixtures thereof;
a difunctional acrylate monomer present in an amount between about 3.0% to 6.0% by weight and selected from the group consisting of: a difunctional alkoxylated acrylate monomer, a difunctional methacrylate monomer, an alkoxylated hexandiol acrylate monomer, a 1,6-hexandiol diacrylate monomer, and mixtures thereof;
a first photoinitiator present in an amount between about 9.0% to 11.0% by weight and comprising an α-hydroxyketone class photoinitiator;
a second photoiniator different from the first photoinitiator, the second photoiniator present in an amount between about 4.0% to 6.0% by weight and comprising an α-aminoketone class photoinitiator; and
one or more copolymers of ethyl acrylate and 2-ethylhexyl acrylate present in an amount between about 0.7% to 1.5% by weight.