# US 10,307,940 B2 · System and method for using a VOC free low radiant flux LED UV curable composition

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- Number: US 10,307,940 B2
- Document ID: US10307940B2
- Status: Granted
- Kind: B2
- Application number: 15/593,985
- Filed: 2017-05-12
- Published: 2017-11-16
- Granted: 2019-06-04
- Earliest claimed: 2016-05-13
- Applicants: MSI Coatings Inc.
- Inventors: Matthew Kent Springer
- Web page: https://patentgrep.com/patent/US10307940B2

## CPC

- B29C 35/0805: {using electromagnetic radiation}
- B29C 37/0067: {Using separating agents during or after moulding; Applying separating agents on preforms or articles, e.g. to prevent sticking to each other (separating agents B29C33/60)}
- B29C 70/06: Fibrous reinforcements only
- B29C 73/02: using liquid or paste-like material (B29C73/16 takes precedence)
- B32B 3/12: characterised by a layer of regularly- arranged cells, e.g. a honeycomb structure
- B32B 7/12: using interposed adhesives or interposed materials with bonding properties
- B32B 15/10: of wood
- B32B 15/20: comprising aluminium or copper {(B32B15/016 and B32B15/017 take precedence)}
- B32B 21/042: {of wood (B32B21/13 takes precedence)}
- B32B 21/06: of paper or cardboard
- B32B 21/14: comprising wood board or veneer
- C08J 3/24: Crosslinking, e.g. vulcanising, of macromolecules (mechanical aspects B29C35/00; crosslinking agents C08K)
- C08J 3/28: Treatment by wave energy or particle radiation
- C08J 5/04: Reinforcing macromolecular compounds with loose or coherent fibrous material
- C09D 5/18: Fireproof paints {including high temperature resistant paints}
- C09D 133/08: Homopolymers or copolymers of acrylic acid esters
- B05D 3/067: {Curing or cross-linking the coating}
- B05D 5/00: Processes for applying liquids or other fluent materials to surfaces to obtain special surface effects, finishes or structures
- B29C 37/02: Deburring or deflashing {(thermal deburring in general B23D79/005)}
- B29C 2035/0827: {using UV radiation}
- B29K 2105/06: containing reinforcements, fillers or inserts
- B29K 2309/08: Glass
- B29L 2031/3097: {Cosmonautical vehicles; Rockets}
- B32B 2250/02: 2 layers
- B32B 2255/08: on wood layer
- B32B 2255/26: Polymeric coating
- B32B 2262/101: Glass fibres
- B32B 2262/106: Carbon fibres, e.g. graphite fibres
- B32B 2307/3065: Flame resistant or retardant, fire resistant or retardant
- B32B 2603/00: Vanes, blades, propellers, rotors with blades
- B32B 2605/08: Cars
- B32B 2605/12: Ships
- B32B 2605/18: Aircraft
- C08J 2381/02: Polythioethers; Polythioether-ethers
- B29C: SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING (making preforms B29B11/00; making laminated products by combining previously unconnected layers which become one product whose layers will remain together B32B37/00 - B32B41/00)
- B32B: LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29)
- 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)
- B05D: PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL (conveying articles or workpieces through baths of liquid B65G, e.g. B65G49/02)
- B29K: INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR {MOULDS, } REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
- B29L: INDEXING SCHEME ASSOCIATED WITH SUBCLASS B29C, RELATING TO PARTICULAR ARTICLES

## Abstract

The present invention generally relates to a system and method for using a volatile organic compound (VOC) free low radiant flux LED UV curable composition, and more particularly to unique and novel uses of the composition such as one or two or more of a fire retardant, clear coat, composite material, resin, top coat, improved holdout coating, a sealant coat, and combinations of the same.

## Claims

### Claim 1

A method of using a volatile organic compound (VOC) free low radiant flux UV curable composition as a fire retardant coating to improve a fire retardant nature of a substrate and protect the substrate, comprising the steps of:
(a) preparing the substrate for receiving the VOC free low radiant flux UV curable composition by roughening a surface of the substrate and cleaning the surface;
(b) providing the VOC free low radiant flux UV curable composition;
(c) applying the VOC free low radiant flux UV curable composition on the substrate to form a combination fire retardant and protective coating; and
(d) applying an energy source having a wavelength in a range from about 360 nm to about 420 nm and a radiant flux at a surface of the applied coating of about 100 mW/cm2 or less to cure the combination fire retardant and protective coating within about 120 seconds or less, wherein the cured fire retardant and protective coating passes an aerospace sixty second vertical flammability test with a flame time of zero seconds and a drip flame time of zero seconds,
wherein the VOC free low radiant flux UV curable composition, comprises:
an acrylate monomers/oligomers;
a thiol monomers/oligomers;
a photo initiator; and
a radical inhibitor.

### Claim 2 (depends on 1)

The method of claim 1, wherein the radiant flux at the surface of the coating is about 25 mW/cm2 or less.

### Claim 3 (depends on 1)

The method of claim 1, wherein the radiant flux at the surface of the coating is about 10 mW/cm2 or less.

### Claim 4 (depends on 1)

The method of claim 1, wherein the radiant flux at the surface of the coating is about 5 mW/cm2 or less.

### Claim 5 (depends on 1)

The method of claim 1, wherein the substrate comprises an aerospace panel comprising a honeycomb substrate and a decorative material adhered to the honeycomb substrate.

### Claim 6 (depends on 1)

The method of claim 1, wherein the substrate comprises a first substrate and a second substrate comprising a decorative material arranged on the first substrate.

### Claim 7 (depends on 6)

The method of claim 6, wherein the decorative material comprises a wood veneer.

### Claim 8 (depends on 6)

The method of claim 6, wherein the decorative material comprises a wood stain.

### Claim 9 (depends on 6)

The method of claim 6, wherein the VOC free low radiant flux UV curable composition comprises ninety-five (95%) percent solids or greater.

### Claim 10 (depends on 6)

The method of claim 6, wherein the acrylate monomers/oligomers comprises one or more of ethylene glycol di(meth)acrylate, tetraethyleneglycol-di(meth)acrylate, poly(ethylene glycol)dimethacrylates, the condensation product of bisphenol A and glycidyl methacrylate, 2,2′-bis [4-(3-methacryloxy-2-hydroxypropoxy)-phenyl]propane, hexanediol di(meth)acrylate, tripropylene glycol di(meth)acrylate, butanediol di(meth)acrylate, neopentyl glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, dipropylene glycol di(meth)acrylate, allyl (meth)acrylate trimethylolpropane triacrylate, tris(2-hydroxy ethyl) isocyanurate triacrylate, tricyclodecane dimethanol diacrylate, and combinations thereof.

### Claim 11 (depends on 6)

The method of claim 6, wherein the thiol monomers/oligomers comprises one or more of ethylene glycol bis(thioglycolate), ethylene glycol bis(3-mercaptopropionate), pentaerythritol tetra(3-mercaptopropionate), trimethylolpropane tris(3-mercaptopropionate), pentaerythritol tetra(2-mercaptoacetate), trimethylolpropane tris(2-mercaptoacetate), 1,6-hexanedithiol, 1,2-benzenedithiol, 1,3-benzenedithiol, isophorone diurethane thiol, and combinations thereof.

### Claim 12 (depends on 6)

The method of claim 6, wherein the photo initiator comprises one or more of 2,2-dimethoxy-1,2-diphenylethan-1-one, bis(2,4,6-trimethylbenzoyl)-phenylphosphineoxide, 1-hydroxy-cyclohexyl-phenyl-ketone, 1-hydroxycyclohexyl benzophenone, trimethyl-benzoyl-diphenyl-phosphine-oxide, and combinations thereof.

### Claim 13 (depends on 6)

The method of claim 6, wherein the radical inhibitor comprises one or more of N-nitrosophenylhydroxylamine, hydroquinone and derivatives, monomethyl ether hydroquinone, benzoquinone, methoxy hydroquinone, tert butyl catechol, phenothiazine, or pyrogallol.

### Claim 14

A method of using a volatile organic compound (VOC) free low radiant flux UV curable composition as a fire retardant and clear protective coating to improve a fire retardant nature of a substrate and protect the substrate, comprising the steps of:
(a) providing the substrate;
(b) preparing the substrate for receiving the VOC free low radiant flux UV curable composition by roughening a surface of the substrate and cleaning the surface;
(c) providing the VOC free low radiant flux UV curable composition;
(d) applying the VOC free low radiant flux UV curable composition on the substrate to form a fire retardant and clear protective coating; and
(e) applying an energy source having a wavelength in a range from about 360 nm to about 420 nm and a radiant flux at a surface of the applied coating of about 100 mW/cm2 or less to cure the fire retardant coating within about 120 seconds or less, wherein the cured fire retardant and clear protective coating passes an aerospace sixty second vertical flammability test with a flame time of zero seconds and a drip flame time of zero seconds, repeating steps (b), (d) and (e) for a predetermined number of repeats in order to achieve a predetermined thickness,
wherein the VOC free low radiant flux UV curable composition, comprises:
an acrylate monomers/oligomers;
a thiol monomers/oligomers;
a photo initiator; and
a radical inhibitor.

### Claim 15 (depends on 14)

The method of claim 14, wherein the predetermined thickness is about 10 mils or greater.

### Claim 16 (depends on 1)

The method of claim 1, wherein the apply step (d) comprises using a low-pressure (HVLP) spray gun to apply a wet coat of the VOC free low radiant flux UV curable composition onto the substrate to a thickness of about 2 mils or greater wherein the roughening the surface of the substrate comprises the step of mechanically roughening the surface.

### Claim 17 (depends on 1)

The method of claim 1, wherein the substrate comprises an aerospace panel comprising a honeycomb substrate and having a decorative material adhered to the honeycomb substrate.

### Claim 18 (depends on 17)

The method of claim 17, wherein the honeycomb substrate comprises one or more of fiberglass material, alloy material, aluminum alloy material, carbon fiber material, thermoplastic material, wood material, and metal material.

### Claim 19

A method of using a volatile organic compound (VOC) free low radiant flux UV curable composition as a fire retardant and protective coating, comprising the steps of:
(a) preparing a substrate for receiving the VOC free low radiant flux UV curable composition;
(b) applying the VOC free low radiant flux UV curable composition to the substrate; and
(c) applying an energy source having a wavelength in a range from about 360 nm to about 420 nm and a radiant flux at a surface of the applied UV curable composition of about 500 mW/cm2 or less to cure at least a portion of the UV curable composition and form the fire retardant and protective coating on the substrate, wherein the cured fire retardant and protective coating passes an aerospace sixty second vertical flammability test, and
wherein the VOC free low radiant flux UV curable composition, comprises:
an acrylate monomers/oligomers;
a thiol monomers/oligomers;
a photo initiator; and
a radical inhibitor.

### Claim 20 (depends on 19)

The method of claim 19, wherein the cured fire retardant and protective coating of step (c) is tack free.

### Claim 21 (depends on 19)

The method of claim 19, wherein the substrate is configured to be used in one of an aerospace application, a marine application, an industrial application, a bathware application, a wood finishing application and an automotive application.

### Claim 22 (depends on 19)

The method of claim 19, wherein the substrate comprises a temperature sensitive substrate.

### Claim 23 (depends on 19)

The method of claim 19, wherein the substrate comprises a wood material.

### Claim 24 (depends on 19)

The method of claim 19, wherein the substrate comprises one or more of a fiberglass material, a carbon fiber material, a plastic material, and a thermoplastic material.

### Claim 25 (depends on 19)

The method of claim 19, wherein the substrate comprises one or more of a metal and an alloy material.

### Claim 26 (depends on 19)

The method of claim 19, wherein the substrate comprises a cement material.

### Claim 27 (depends on 19)

The method of claim 19, wherein the substrate comprises an automotive panel.

### Claim 28 (depends on 19)

The method of claim 19, wherein the substrate comprises an aerospace panel.

### Claim 29 (depends on 28)

The method of claim 28, wherein the aerospace panel comprises a honeycomb core.

### Claim 30 (depends on 28)

The method of claim 28, wherein the aerospace panel further comprises a veneer material.

### Claim 31 (depends on 28)

The method of claim 28, wherein the aerospace panel further comprises a decorative material.

### Claim 32 (depends on 19)

The method of claim 19, wherein the cured fire retardant and protective coating of step (c) passes an aerospace sixty second vertical flammability test with a flame time of zero seconds and a drip flame time of zero seconds.

### Claim 33 (depends on 19)

The method of claim 19, further comprising the steps of:
(d) preparing the substrate with the cured fire retardant and clear protective coating for receiving the VOC free low radiant flux UV curable composition;
(e) applying the VOC free low radiant flux UV curable composition to the substrate with the cured fire retardant and clear protective coating; and
(f) applying an energy source to the applied UV curable composition to cure at least a portion of the UV curable composition to form the fire retardant and protective coating on the cured fire retardant and clear protective coating.

### Claim 34 (depends on 33)

The method of claim 33, further comprising the steps of repeating steps (d), (e) and (f) for a predetermined number of repeats in order to achieve a predetermined thickness of the cured fire retardant and protective coating.

### Claim 35 (depends on 19)

The method of claim 19, wherein the energy source has a radiant flux at the surface of the applied coating of about 75 mW/cm2 or less.

### Claim 36 (depends on 19)

The method of claim 19, wherein the energy source has a radiant flux at the surface of the applied coating of about 40 mW/cm2 or less.

### Claim 37 (depends on 19)

The method of claim 19, wherein the energy source has a radiant flux at the surface of the applied coating of about 25 mW/cm2 or less.

### Claim 38 (depends on 19)

The method of claim 19, wherein the energy source has a radiant flux at the surface of the applied coating of about 15 mW/cm2 or less.

### Claim 39 (depends on 19)

The method of claim 19, wherein the VOC free low radiant flux UV curable composition comprises ninety-five (95%) percent solids or greater.

### Claim 40 (depends on 19)

The method of claim 19, wherein the VOC free low radiant flux UV curable composition comprises one-hundred (100%) percent solids.

### Claim 41 (depends on 19)

The method of claim 19, wherein the acrylate monomers/oligomers comprises one or more of ethylene glycol di(meth)acrylate, tetraethyleneglycol-di(meth)acrylate, poly(ethylene glycol)dimethacrylates, the condensation product of bisphenol A and glycidyl methacrylate, 2,2′-bis[4-(3-methacryloxy-2-hydroxypropoxy)-phenyl]propane, hexanediol di(meth)acrylate, tripropylene glycol di(meth)acrylate, butanediol di(meth)acrylate, neopentyl glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, dipropylene glycol di(meth)acrylate, allyl (meth)acrylate trimethylolpropane triacrylate, tris(2-hydroxy ethyl) isocyanurate triacrylate, tricyclodecane dimethanol diacrylate, and combinations thereof.

### Claim 42 (depends on 19)

The method of claim 19, wherein the thiol monomers/oligomers comprises one or more of ethylene glycol bis(thioglycolate), ethylene glycol bis(3-mercaptopropionate), pentaerythritol tetra(3-mercaptopropionate), trimethy lolpropane tris(3-mercaptopropionate), pentaerythritol tetra(2-mercaptoacetate), trimethy lolpropane tris(2-mercaptoacetate), 1,6-hexanedithiol, 1,2-benzenedithiol, 1,3-benzenedithiol, isophorone diurethane thiol, and combinations thereof.

### Claim 43 (depends on 19)

The method of claim 19, wherein the photo initiator comprises one or more of 2,2-dimethoxy- 1,2-diphenylethan-1-one, bis(2,4,6-trimethylbenzoyl)-phenylphosphineoxide, 1-hydroxy-cyclohexyl-phenyl-ketone, 1-hydroxycyclohexyl benzophenone, trimethyl-benzoyl-diphenyl-phosphine-oxide, and combinations thereof.

### Claim 44 (depends on 19)

The method of claim 19, wherein the radical inhibitor comprises one or more of N-nitrosophenylhydroxylamine, hydroquinone and derivatives, monomethyl ether hydroquinone, benzoquinone, methoxy hydroquinone, tert butyl catechol, phenothiazine, or pyrogallol.

### Claim 45 (depends on 19)

The method of claim 19, wherein the energy source has a wavelength in a range from about 380 nm to about 400 nm.

### Claim 46 (depends on 19)

The method of claim 19, wherein the energy source comprises a light emitting diode (LED).