US20130280544A1 - Radiation curable coating compositions for metal - Google Patents
Radiation curable coating compositions for metal Download PDFInfo
- Publication number
- US20130280544A1 US20130280544A1 US13/976,803 US201113976803A US2013280544A1 US 20130280544 A1 US20130280544 A1 US 20130280544A1 US 201113976803 A US201113976803 A US 201113976803A US 2013280544 A1 US2013280544 A1 US 2013280544A1
- Authority
- US
- United States
- Prior art keywords
- meth
- acrylate
- coating composition
- isocyanate
- radiation curable
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1811—C10or C11-(Meth)acrylate, e.g. isodecyl (meth)acrylate, isobornyl (meth)acrylate or 2-naphthyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- 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
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- C09D175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
- C09D175/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F230/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing phosphorus
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- 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
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- 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
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- 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
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- C09D175/08—Polyurethanes from polyethers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- 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
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0041—Photosensitive materials providing an etching agent upon exposure
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
- G03F7/035—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2390/00—Containers
- C08G2390/40—Inner coatings for containers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31678—Of metal
- Y10T428/31692—Next to addition polymer from unsaturated monomers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31678—Of metal
- Y10T428/31692—Next to addition polymer from unsaturated monomers
- Y10T428/31699—Ester, halide or nitrile of addition polymer
Definitions
- the present disclosure relates to radiation curable coating compositions that can provide useful coatings and coated surfaces for packaging materials such as metal cans.
- radiation curable coatings such as those that cure through ultra-violet (“UV”) radiation or electron beam (“EB”) radiation have a tendency to be inflexible cured coatings that are prone to higher levels of shrinkage. Consequently, coatings utilizing chemistry for such curing have been heretofore recognized by those skilled in the art to be inadequate in terms of direct to metal adhesion, formability, and retort resistance as well as limited in application in terms of adhesion and extensibility within the flexible packaging industry.
- UV ultra-violet
- EB electron beam
- adhesion promoters are known in the art, it is surprising that higher levels of these compounds than normally used in supplier literature or other published information offer such a significant improvement in adhesion and do not cause severe problems with blush resistance of the cured coating. Higher levels are especially useful on “cleaned only” metal substrates without pretreatment and chrome free substrates.
- the present invention includes radiation curable coating compositions comprising a (meth)acrylate functional compound and an adhesion promoting (meth)acrylate compound as well as radiation curable coating compositions comprising a (meth)acrylate functional compound, a poly(meth)acrylate and a reactive diluent.
- the present invention also includes packaging comprising: a metal substrate; and a radiation curable coating composition disposed on the substrate.
- the present invention includes methods of coating a packaging comprising: a) preparing a radiation curable coating composition as described herein; and b) applying the coating composition to the packaging.
- the radiation curable coatings of the present invention have been found to be hard, flexible and exhibit good adhesion to metal substrates.
- the coated films of the present invention can withstand retort conditions with minimal blush and minimal loss of adhesion.
- the present invention includes radiation curable coating compositions comprising a (meth)acrylate functional compound and an adhesion promoting (meth)acrylate compound as well as radiation curable coating compositions comprising a (meth)acrylate functional compound, a poly(meth)acrylate and a reactive diluent.
- the (meth)acrylate functional compound can be made for non-limiting example from the reaction of a multifunctional isocyanate, a polyol and a hydroxyl functional (meth)acrylate in the presence of a catalyst.
- the (meth)acrylate functional compound and the adhesion promoting (meth)acrylate compound may each be a monomer, an oligomer, or combination thereof, and references to a monomer are understood to include an oligomer and vice-versa.
- the (meth)acrylate functional compound is present in an amount up to about 50 wt % of the coating composition.
- the (meth)acrylate functional compounds can be made from various materials known in the art, such as and without limitation, a (meth)acrylate functional polyester, a (meth)acrylate functional polyacrylate, a (meth)acrylate functional polyether, a (meth)acrylate functional polycarbonate, an oil polyol ether, a (meth)acrylate functional urethane, a (meth)acrylate functional compound of WO 2008/151286 (the contents of which are incorporated herein by reference), or a combination thereof.
- One possible (meth)acrylate functional compound is a urethane, made readily but not exclusively from the reaction of a multifunctional isocyanate, a polyol and a hydroxyl functional (meth)acrylate in the presence of a catalyst.
- the adhesion promoting (meth)acrylate compound may be for non-limiting example a phosphate (meth)acrylic-functional monomer, a carboxylate (meth)acrylic-functional monomer, a phosphate (meth)acrylic-functional oligomer, a carboxylate (meth)acrylic-functional oligomer, or a combination thereof.
- the phosphate (meth)acrylic-functional monomer may include phosphate esters or hydroxyl functional esters of methacrylic acid.
- the carboxylate (meth)acrylic-functional monomer/oligomer may include without limitation carboxylic acid functional esters, carboxylic acid functional ethers and combinations thereof.
- the phosphate (meth)acrylic-functional monomer/oligomer may be present in an amount up to about 12 wt % of the coating composition.
- the carboxylate (meth)acrylic-functional monomer/oligomer may be present in an amount from about 0.5 to about 50 wt % of the coating composition.
- the adhesion promoting (meth)acrylate compound may be present in an amount up to about 65 wt % of the total coating composition film forming components.
- the poly(meth)acrylate is present in an amount up to about 25 wt % of the coating composition or from about 5 to about 15 wt %.
- the poly(meth)acrylate may include without limitation tricyclodecyl dimethanol diacrylate, dipropylene glycol diacrylate, and the like, as well as combinations thereof.
- the reactive diluent can be present in an amount up to about 95 wt % of the coating composition or from about 20 to about 60 wt %.
- the reactive diluent may include without limitation a mono(meth)acrylate.
- Multifunctional isocyanates for use in the present invention include but are not limited to an isocyanate, a di-isocyanate, a poly-isocyanate, an aliphatic isocyanate, an aromatic isocyanate, di-hexamethylene, poly-hexamethylene, hexane diisocyanate, isophorane, MDI, and combinations thereof.
- Polyols for use in the present invention include but are not limited to polyesters, diols, alcohols, polycarbonates, polypropylene glycol, polyethylene glycol, polytetramethylene oxide, and combinations thereof.
- the polyol has a molecular weight of about 100 to about 10,000, or about 500 to about 5000.
- Suitable hydroxyl functional (meth)acrylates include but are not limited to a hydroxyl monomer, 4-hydroxy butyl (meth)acrylate, butane diol mono-(meth)acrylate, hydroxy propyl (meth)acrylate, hydroxy ethyl (meth)acrylate, an extended hydroxyl (meth)acrylate, polycaprolactone (meth)acrylate, and combinations thereof.
- the amount of the hydroxyl functional (meth)acrylate can range from about 5% to about 95% by weight based on the weight of the (meth)acrylate functional compound, and in other examples from about 25% to about 75% by weight based on the weight of the (meth)acrylate functional compound.
- the molar ratio of multifunctional isocyanate/polyol/hydroxyl functional (meth)acrylate is about 1/0.1-2/0.2-5, about 1/0.25-0.75/0.5-2.5, or about 1/0.5/2. On a weight basis, the ratio can be about 1 to about 75% of the multifunctional isocyanate to up to about 90% of the polyol to about 1 to about 99% of the hydroxyl functional (meth)acrylate. In some embodiments, there is a slight excess of hydroxyl functionality over isocyanate functionality which allows the reaction to proceed to at least 99% conversion of the multifunctional isocyanate.
- Additional hydroxyl functional materials can be included with the hydroxyl functional (meth)acrylate. Additional hydroxy functional materials can include but are not limited to alcohols, diols, polyols, polyesters, polyethers (such as for non-limiting example, benzyl alcohol, trimethylol propane, polypropylene glycol, hexane diol), and combinations thereof.
- the catalyst can be a catalyst suitable for polymerization such as without limitation a tin catalyst such as dibutyl tin di-laurate or dibutyl tin oxide, a zirconium catalyst such as zirconium propionate, a bismuth catalyst such as bismuth neodecanoate, a tertiary amine catalyst such as triethylene diamine, or a combination thereof.
- the amount of the catalyst can range from about 1 ppm to about 10,000 ppm, from about 10 ppm to about 1,000 ppm, or from about 20 ppm to about 200 ppm. It is generally convenient to employ the catalyst in the form of a solution in an organic solvent.
- suitable solvents include without limitation aromatic hydrocarbon solvents, cycloaliphatic polar solvents (such as cycloaliphatic ketones including cyclohexanone), polar aliphatic solvents (such as alkoxyalkanols including 2-methoxyethanol), the diol starting material, and combinations thereof.
- aromatic hydrocarbon solvents such as cycloaliphatic polar solvents (such as cycloaliphatic ketones including cyclohexanone), polar aliphatic solvents (such as alkoxyalkanols including 2-methoxyethanol), the diol starting material, and combinations thereof.
- cycloaliphatic polar solvents such as cycloaliphatic ketones including cyclohexanone
- polar aliphatic solvents such as alkoxyalkanols including 2-methoxyethanol
- An air atmosphere and an effective inhibitor such as for example methoxy hydroquinone, hydroquinone, di-tert butyl hydroquinone, butylated hydroxyl toluene, phenothiazine, or a combination thereof can be used to prevent free radical polymerization of the hydroxyl functional (meth)acrylate monomer/oligomer.
- the inhibitor may be present in an amount of about 10 to about 10,000 ppm.
- the reaction of the multifunctional isocyanate, the polyol and the hydroxyl functional (meth)acrylate can be carried out at a temperature that ranges from about ambient temperature to about 70° C. or about 110° C., an in other examples from about 90° C. to about 100° C.
- a diluent may be added during the reaction to reduce viscosity, such as for non-limiting example a free radical reactive species such as a (meth)acrylate, a methyl(meth)acrylate, isobornyl (meth)acrylate, t-butyl cyclohexyl (meth)acrylate, tricyclodecyl dimethanol di(meth)acrylate, or a combination thereof.
- the diluent may be present in an amount up to about 75% or more of the total batch weight.
- Various embodiments of the present invention provide radiation cured coating compositions that are essentially free of BADGE and NOGE even when cured with low energy curing, such as electron beam curing.
- the various radiation cured coating compositions described herein have improved flexibility and are, for example, more flexible than coatings with other (meth)acrylate coatings.
- the coating compositions of the present invention can also provide retort resistance for rigid packaging applications according to the most common retort tests know for rigid packaging applications.
- the curable coating compositions of the present invention can be used without the need for a prime coat so as to be in direct contact to metal substrates.
- the coating compositions can be applied to substrates in any manner known to those skilled in the art.
- the following ingredients were added under agitation while a mixing operation was done under medium speed agitation.
- the finished coating was drawn down over a metal substrate and cured under electron beam at a minimum setting of 3 megarads per 90 kilovolts.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Paints Or Removers (AREA)
- Polyurethanes Or Polyureas (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US13/976,803 US20130280544A1 (en) | 2010-12-28 | 2011-12-23 | Radiation curable coating compositions for metal |
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201061427582P | 2010-12-28 | 2010-12-28 | |
EP11154036 | 2011-02-10 | ||
EP11154036.5 | 2011-02-10 | ||
US13/976,803 US20130280544A1 (en) | 2010-12-28 | 2011-12-23 | Radiation curable coating compositions for metal |
PCT/EP2011/073931 WO2012089656A2 (en) | 2010-12-28 | 2011-12-23 | Radiation curable coating compositions for metal |
Publications (1)
Publication Number | Publication Date |
---|---|
US20130280544A1 true US20130280544A1 (en) | 2013-10-24 |
Family
ID=43706753
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US13/976,763 Active US9856392B2 (en) | 2010-12-28 | 2011-12-23 | Radiation curable coating compositions for metal |
US13/976,803 Abandoned US20130280544A1 (en) | 2010-12-28 | 2011-12-23 | Radiation curable coating compositions for metal |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US13/976,763 Active US9856392B2 (en) | 2010-12-28 | 2011-12-23 | Radiation curable coating compositions for metal |
Country Status (14)
Country | Link |
---|---|
US (2) | US9856392B2 (es) |
EP (2) | EP2658932A2 (es) |
KR (2) | KR20140007351A (es) |
CN (2) | CN103443209B (es) |
AU (2) | AU2011351530B2 (es) |
BR (1) | BR112013015806B1 (es) |
CA (2) | CA2822524A1 (es) |
ES (1) | ES2564483T5 (es) |
HK (1) | HK1192272A1 (es) |
MX (2) | MX2013007458A (es) |
MY (1) | MY167220A (es) |
RU (2) | RU2013132741A (es) |
WO (2) | WO2012089656A2 (es) |
ZA (2) | ZA201304518B (es) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10005935B2 (en) | 2015-05-01 | 2018-06-26 | Lord Corporation | Adhesive for rubber bonding |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2010100122A1 (en) | 2009-03-05 | 2010-09-10 | Akzo Nobel Coatings International B.V. | Hydroxyl functional oil polyols and coating compositions prepared from hydroxyl functional oil polyols |
RU2606632C2 (ru) | 2011-12-21 | 2017-01-10 | Акцо Нобель Коатингс Интернэшнл Б.В. | Композиции на водной основе для получения покрытий |
WO2013092541A1 (en) | 2011-12-21 | 2013-06-27 | Akzo Nobel Coatings International B.V. | Solvent-based coating compositions |
CN103254353A (zh) * | 2013-04-27 | 2013-08-21 | 晟通科技集团有限公司 | 一种水溶性丙烯酸树脂及用其制作的亲水涂料 |
CN107109112B (zh) * | 2014-10-08 | 2020-07-03 | 巴斯夫欧洲公司 | 经磷酸酯改性的丙烯酸多元醇 |
EP3516004A4 (en) | 2016-09-19 | 2020-05-13 | Dow Global Technologies LLC | TWO-COMPONENT SOLVENT-FREE ADHESIVE COMPOSITIONS AND METHODS OF MAKING SAME |
CN108977047A (zh) * | 2018-05-23 | 2018-12-11 | 无锡万博涂料化工有限公司 | 一种基于eb固化的卷材涂料 |
KR102315050B1 (ko) * | 2020-04-07 | 2021-10-21 | 대주전자재료 주식회사 | 고온 이형 가능한 도전성 접착제 및 태양 전지 모듈 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5128391A (en) * | 1988-02-24 | 1992-07-07 | Borden, Inc. | Extensible and pasteurizable radiation curable coating for metal containing organofunctional silane adhesion promoter |
Family Cites Families (68)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3929929A (en) | 1973-05-29 | 1975-12-30 | Ici America Inc | Vinyl urethane resins |
US4025548A (en) | 1974-02-04 | 1977-05-24 | The O'brien Corporation | Radiation curable oligomers |
US4153778A (en) | 1978-03-30 | 1979-05-08 | Union Carbide Corporation | Acrylyl capped urethane oligomers |
US4508916A (en) | 1979-04-11 | 1985-04-02 | Minnesota Mining And Manufacturing Company | Curable substituted urethane acrylates |
AU530007B2 (en) | 1981-04-02 | 1983-06-30 | Dow Chemical Company, The | Laminated container body and manufacture thereof |
US4452374A (en) | 1981-04-02 | 1984-06-05 | The Dow Chemical Company | Manufacture of draw-redraw cans using an irradiated film laminated or extrusion coated steel sheet material |
FI832883A (fi) | 1982-08-12 | 1984-02-13 | Scm Corp | Vattenhaltig sjaelvhaerdbar polymerblandning |
JPS6053570A (ja) | 1983-09-05 | 1985-03-27 | Toray Ind Inc | 電子線キユア性塗料組成物 |
JPS60112865A (ja) | 1983-11-25 | 1985-06-19 | Nippon Paint Co Ltd | プレコ−ト用塗料組成物及びプレコ−ト鋼板 |
US4607084A (en) | 1984-06-11 | 1986-08-19 | Celanese Specialty Resins, Inc. | Radiation curable acrylated polyurethane oligomer compositions |
JPS6392618A (ja) | 1986-10-07 | 1988-04-23 | Sumitomo Chem Co Ltd | リン酸エステルを含む光硬化性組成物 |
US5128387A (en) | 1987-07-28 | 1992-07-07 | Borden, Inc. | Extensible and pasteurizable radiation curable coating for metal |
JPH08503517A (ja) | 1992-11-24 | 1996-04-16 | ミネソタ・マイニング・アンド・マニュファクチュアリング・カンパニー | 放射線硬化性オリゴマーおよびそれらから製造した磁気記録媒体 |
JPH0859770A (ja) | 1994-08-15 | 1996-03-05 | Dainippon Ink & Chem Inc | ポリウレタンポリ尿素架橋微粒子分散体及びその製造方法 |
JPH0931150A (ja) | 1995-05-15 | 1997-02-04 | Dainippon Ink & Chem Inc | ウレタンプレポリマー、活性エネルギー線硬化型水性ポリウレタン樹脂組成物、及びその製造方法 |
US5578693A (en) | 1995-09-05 | 1996-11-26 | Bomar Specialties Company | Multifunctional terminally unsaturated urethane oligomers |
US6743879B1 (en) | 1996-04-10 | 2004-06-01 | Hehr International Inc. | Methacrylic-urethane oligomers, method of preparation and oligomer-containing resin compositions |
JPH10204325A (ja) | 1997-01-27 | 1998-08-04 | Toyo Ink Mfg Co Ltd | 電子線硬化型塗料およびその硬化方法 |
EP0975693B2 (en) * | 1997-04-22 | 2006-01-18 | Koninklijke DSM N.V. | Liquid curable resin composition |
US6488993B2 (en) | 1997-07-02 | 2002-12-03 | William V Madigan | Process for applying a coating to sheet metal |
JP4288691B2 (ja) | 1999-04-15 | 2009-07-01 | 日立化成工業株式会社 | 光硬化性樹脂組成物を含む塗料を用いた硬化塗膜の製造法 |
JP2001038452A (ja) | 1999-07-28 | 2001-02-13 | Daido Steel Co Ltd | 連続鋳造方法 |
DE19960693A1 (de) | 1999-12-16 | 2001-07-19 | Dupont Performance Coatings | Verfahren zur anodischen Elektrotauchlackierung, sowie Elektrotauchlacke |
US6306468B1 (en) | 2000-02-25 | 2001-10-23 | Polymeric Processes Inc. | Metal tube coating process |
WO2001088050A2 (en) * | 2000-05-18 | 2001-11-22 | Henkel Loctite Corporation | Adhesive compositions for bonding passive substrates such as magnesium alloys |
US6951910B2 (en) | 2000-09-14 | 2005-10-04 | Dsm Ip Assets B.V. | Coating compositions for plastic substrates |
DE10048849A1 (de) | 2000-10-02 | 2002-04-18 | Basf Coatings Ag | Verfahren zur Herstellung eines thermisch und mit aktinischer Strahlung härtbaren Mehrkomponentensystems und seine Verwendung |
EP1254936B1 (en) | 2001-05-04 | 2007-03-14 | Rohm And Haas Company | Method for preparing a laminate |
US6433091B1 (en) * | 2001-05-10 | 2002-08-13 | Henkel Loctite Corporation | Adhesive composition |
US20020172760A1 (en) | 2001-05-17 | 2002-11-21 | Shu An | Apparatus and process for the post-production repair of converted can ends |
US6974665B2 (en) | 2001-09-06 | 2005-12-13 | University Of Nebraska | In situ screening to optimize variables in organic reactions |
US20030079333A1 (en) | 2001-10-29 | 2003-05-01 | Guthrie Joseph D. | Process for making a metal-polymer composite having an irradiated polymer coating |
US20030225149A1 (en) | 2002-04-30 | 2003-12-04 | Blazecka Peter G. | Process for preparing highly functionalized gamma-butyrolactams and gamma-amino acids |
US6696106B1 (en) | 2002-09-11 | 2004-02-24 | Alcoa Inc. | Primer for radiation curable coating compositions |
US7122684B2 (en) | 2003-03-13 | 2006-10-17 | Roche Colorado Corporation | Process for preparing 1,2-diamino compounds |
JP2005060631A (ja) * | 2003-08-20 | 2005-03-10 | Jsr Corp | 放射線硬化性液状樹脂組成物 |
US7109252B2 (en) | 2003-11-25 | 2006-09-19 | Bomar Specialties Company | TMXDI-based oligomer and formulations containing it |
US6989407B2 (en) | 2004-01-09 | 2006-01-24 | Northwest Coatings, Llc | Radiation curable laminating adhesives based on cycloaliphatic carboxylic acid functional monomers |
CN1651533A (zh) * | 2004-01-13 | 2005-08-10 | 上海飞凯光电材料有限公司 | 辐射固化涂料及其应用 |
DE102004012902A1 (de) | 2004-03-17 | 2005-10-06 | Bayer Materialscience Ag | Herstellung von neuen strahlenhärtenden Bindemitteln |
EP1616710A1 (de) | 2004-07-01 | 2006-01-18 | Alcan Technology & Management Ltd. | Verfahren zur Herstellung eines Verpackungsmaterials |
US7297748B2 (en) | 2004-08-31 | 2007-11-20 | Rhodia Inc. | Direct to metal polyurethane coating compositions |
US7368171B2 (en) | 2004-09-03 | 2008-05-06 | H.B. Fuller Licensing & Financing, Inc. | Laminating adhesive, laminate including the same, and method of making a laminate |
KR20080006640A (ko) | 2005-05-02 | 2008-01-16 | 사이텍 설패이스 스페셜티즈, 에스.에이. | 접착제 조성물 및 이의 제조 방법 |
JP4899535B2 (ja) | 2005-08-17 | 2012-03-21 | セントラル硝子株式会社 | 防曇性被膜及び防曇性物品 |
US20070088111A1 (en) | 2005-08-26 | 2007-04-19 | Ppg Industries Ohio, Inc. | Coating compositions exhibiting corrosion resistance properties, related coated substrates, and methods |
JP5021194B2 (ja) | 2005-09-15 | 2012-09-05 | Hoya株式会社 | 硬化性組成物及びそれを用いた光学部材 |
KR100725249B1 (ko) * | 2005-12-20 | 2007-06-04 | (주)디피아이 홀딩스 | 철재 도장용 자외선 경화 도료 |
CN100343344C (zh) | 2005-12-26 | 2007-10-17 | 中国化工建设总公司常州涂料化工研究院 | 用于金属镀膜表面防护的紫外光固化涂料 |
EP1818349A1 (en) | 2006-02-13 | 2007-08-15 | Cytec Surface Specialties, S.A. | Radiation curable compositions |
ATE489407T1 (de) | 2006-04-19 | 2010-12-15 | Stepan Co | Strahlungshärtbare zusammensetzungen für verbesserte witterungsbeständigkeit |
JP2007305220A (ja) | 2006-05-11 | 2007-11-22 | Lintec Corp | 光記録媒体製造用シートおよび光記録媒体、ならびにそれらの製造方法 |
CN101096472A (zh) | 2006-06-26 | 2008-01-02 | 上海飞凯光电材料有限公司 | 辐射固化材料粘接性能促进剂 |
CN101117458A (zh) | 2006-08-01 | 2008-02-06 | 天津市振东涂料有限公司 | 一种紫外光或电子束引发的固化涂料 |
DE102006045041A1 (de) | 2006-09-25 | 2008-03-27 | Evonik Degussa Gmbh | Strahlenhärtbare Formulierung, die zu flexiblen Beschichtungen mit erhöhtem Korrosionsschutz auf Metalluntergründen führt |
JP5665318B2 (ja) * | 2006-10-27 | 2015-02-04 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | 非芳香族環系を有する低分子量のエチレン系不飽和化合物を含有する放射線硬化可能な混合物 |
EP2091882B9 (en) | 2006-12-14 | 2012-09-26 | DSM IP Assets B.V. | D1365 bj radiation curable primary coating for optical fiber |
WO2008076302A1 (en) * | 2006-12-14 | 2008-06-26 | Dsm Ip Assets B.V. | D 1368 cr radiation curable primary coating for optical fiber |
ES2551552T3 (es) | 2007-06-05 | 2015-11-19 | Akzo Nobel Coatings International B.V. | Composición de revestimiento curable por radiación derivada de aceites vegetales epoxidados |
US20090012202A1 (en) | 2007-07-03 | 2009-01-08 | Henkel Corporation | Acrylated Urethanes, Processes for Making the Same and Curable Compositions Including the Same |
US20090047531A1 (en) | 2007-08-17 | 2009-02-19 | Ppg Industries Ohio, Inc. | Packages having radiation-curable coatings |
JP2009102208A (ja) | 2007-10-25 | 2009-05-14 | Nof Corp | 防曇ガラス |
DE102007056477A1 (de) * | 2007-11-22 | 2009-05-28 | Kalle Gmbh | Druckfarbensystem zum Bedrucken von Nahrungsmittelhüllen auf Polyamidbasis, bedruckte Nahrungsmittelhüllen und Verfahren zu ihrer Herstellung |
KR100938430B1 (ko) | 2007-12-28 | 2010-01-22 | (주)디피아이 홀딩스 | 금속용 전자선 경화형 도료 조성물 및 이를 이용한 도막 형성 방법 |
US20090176907A1 (en) | 2008-01-08 | 2009-07-09 | Ramesh Subramanian | Direct-to-metal radiation curable compositions |
DE102008021151A1 (de) * | 2008-04-28 | 2009-10-29 | Bayer Materialscience Ag | Blockfeste, strahlungshärtbare Beschichtungssysteme auf Basis hochmolekularer, wässriger Polyurethandispersionen |
US20110214738A1 (en) | 2008-11-12 | 2011-09-08 | Pythagoras Solar Inc. | Concentrating photovoltaic module |
EP2763707B1 (en) * | 2011-10-03 | 2018-03-28 | Hyalex Orthopaedics, Inc. | Polymeric adhesive for anchoring compliant materials to another surface |
-
2011
- 2011-12-23 RU RU2013132741/05A patent/RU2013132741A/ru not_active Application Discontinuation
- 2011-12-23 KR KR20137017278A patent/KR20140007351A/ko not_active Application Discontinuation
- 2011-12-23 CA CA 2822524 patent/CA2822524A1/en not_active Abandoned
- 2011-12-23 EP EP11805520.1A patent/EP2658932A2/en not_active Withdrawn
- 2011-12-23 BR BR112013015806-9A patent/BR112013015806B1/pt active IP Right Grant
- 2011-12-23 AU AU2011351530A patent/AU2011351530B2/en active Active
- 2011-12-23 WO PCT/EP2011/073931 patent/WO2012089656A2/en active Application Filing
- 2011-12-23 EP EP11802104.7A patent/EP2658893B2/en active Active
- 2011-12-23 MY MYPI2013701076A patent/MY167220A/en unknown
- 2011-12-23 RU RU2013133899A patent/RU2650934C2/ru active
- 2011-12-23 US US13/976,763 patent/US9856392B2/en active Active
- 2011-12-23 ES ES11802104T patent/ES2564483T5/es active Active
- 2011-12-23 US US13/976,803 patent/US20130280544A1/en not_active Abandoned
- 2011-12-23 WO PCT/EP2011/073929 patent/WO2012089655A2/en active Application Filing
- 2011-12-23 CN CN201180062309.8A patent/CN103443209B/zh active Active
- 2011-12-23 KR KR1020137015991A patent/KR101963671B1/ko active IP Right Grant
- 2011-12-23 CN CN2011800609419A patent/CN103380181A/zh active Pending
- 2011-12-23 MX MX2013007458A patent/MX2013007458A/es unknown
- 2011-12-23 AU AU2011351531A patent/AU2011351531A1/en not_active Abandoned
- 2011-12-23 MX MX2013007459A patent/MX2013007459A/es not_active Application Discontinuation
- 2011-12-23 CA CA2822527A patent/CA2822527C/en active Active
-
2013
- 2013-06-19 ZA ZA2013/04518A patent/ZA201304518B/en unknown
- 2013-06-19 ZA ZA2013/04519A patent/ZA201304519B/en unknown
-
2014
- 2014-06-10 HK HK14105458.8A patent/HK1192272A1/zh unknown
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5128391A (en) * | 1988-02-24 | 1992-07-07 | Borden, Inc. | Extensible and pasteurizable radiation curable coating for metal containing organofunctional silane adhesion promoter |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10005935B2 (en) | 2015-05-01 | 2018-06-26 | Lord Corporation | Adhesive for rubber bonding |
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US9856392B2 (en) | Radiation curable coating compositions for metal | |
CN101072806A (zh) | 封闭的异氰酸酯和它们在涂料组合物中的用途 | |
KR20020008070A (ko) | 코팅용 수지 조성물 및 경화용 코팅 조성물 | |
TW201542602A (zh) | 胺甲酸乙酯(甲基)丙烯酸酯系化合物、活性能量射線硬化性樹脂組成物及塗佈劑 | |
JPWO2003027163A1 (ja) | アロファネート基を有するポリイソシアネート組成物及びハイソリッド塗料 | |
JP6821792B2 (ja) | ポリイソシアネート硬化剤、水性塗料組成物、塗膜及び塗装物 | |
JP6805268B2 (ja) | ポリイソシアネート組成物及び塗料組成物 | |
JP6437837B2 (ja) | ポリイソシアネート組成物、塗料組成物、及び塗膜 | |
JP2016210944A (ja) | ポリイソシアネート組成物及びその製造方法、硬化性組成物、硬化物、並びに硬化樹脂 | |
CN113817126B (zh) | 一种适用于双组份水性环氧体系的反应型粘度调节组合物及其制备方法和用途 | |
JP2000290493A (ja) | ブロックポリイソシアネート組成物 | |
JPH11100426A (ja) | 水系ポリイソシアネート組成物 | |
JP7401662B2 (ja) | ブロックポリイソシアネート組成物、樹脂組成物、樹脂膜及び積層体 | |
KR102280617B1 (ko) | 상도용 도료 조성물 | |
JP7069653B2 (ja) | ポリイソシアネート組成物およびそれを用いた二液型塗料組成物 | |
JP2023101150A (ja) | ブロックポリイソシアネート組成物、樹脂組成物、樹脂膜及び積層体 | |
JP2024070486A (ja) | ポリイソシアネート組成物、樹脂組成物及び樹脂硬化物 | |
EP4177289A2 (en) | Blocked polyisocyanate composition and method for producing the same, resin composition, resin film and method for producing the same, and laminate | |
WO2023277081A1 (ja) | ブロックポリイソシアネート組成物、樹脂組成物、樹脂膜及び積層体 | |
JP2020132783A (ja) | ウレタン(メタ)アクリレート、これを含む活性エネルギー線硬化性組成物、及びその硬化物 | |
JP2001163940A (ja) | 硬化性組成物 | |
JPH10147627A (ja) | 硬化剤組成物及びそれを用いた一液性熱硬化組成物 | |
JP2006160838A (ja) | ポリイソシアネート組成物 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AS | Assignment |
Owner name: AKZO NOBEL COATINGS INTERNATIONAL B.V., NETHERLAND Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:CRAUN, GARY PIERCE;GARDNER, KENNETH JAMES;MILLER, PATRICIA;REEL/FRAME:030702/0783 Effective date: 20130531 |
|
STCB | Information on status: application discontinuation |
Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION |