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WO1997045458A1 - Composition de finition durcissable a la lumiere ultraviolette et son procede d'utilisation - Google Patents

Composition de finition durcissable a la lumiere ultraviolette et son procede d'utilisation Download PDF

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Publication number
WO1997045458A1
WO1997045458A1 PCT/US1996/015464 US9615464W WO9745458A1 WO 1997045458 A1 WO1997045458 A1 WO 1997045458A1 US 9615464 W US9615464 W US 9615464W WO 9745458 A1 WO9745458 A1 WO 9745458A1
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WO
WIPO (PCT)
Prior art keywords
composition
weight
percent
acrylate
compound
Prior art date
Application number
PCT/US1996/015464
Other languages
English (en)
Inventor
Andrew A. Sokol
Original Assignee
Uv Coatings Limited
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Uv Coatings Limited filed Critical Uv Coatings Limited
Priority to AU73742/96A priority Critical patent/AU7374296A/en
Publication of WO1997045458A1 publication Critical patent/WO1997045458A1/fr

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Classifications

    • 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

Definitions

  • the present invention relates to a substantially volatile organic solvent-free coating composition which is curable by the application of ultraviolet light thereto, and a method of using the composition. More particularly, the present invention relates to such a coating composition which includes a polymerizable compound which includes at least one acrylate-containing compound and a photoinitiator which initiates a polymerization reaction in the composition when it is exposed to ultraviolet light.
  • a coating composition which includes a polymerizable compound which includes at least one acrylate-containing compound and a photoinitiator which initiates a polymerization reaction in the composition when it is exposed to ultraviolet light.
  • a two-part coating composition curable by exposure to ultraviolet light or other energy source which, generally, comprises a mixture of acrylates and a photoinitiator.
  • the maior predicate of the prior inventions is the elimination of volatile organic solvents and hazardous air pollutants (HAPS) from their respective systems, while still being sprayable.
  • HAPS hazardous air pollutants
  • the inventions of the related applications provide a manor improvement in the art, especially from a health and environmental standpoint.
  • the viscosity of the composition must remain within a certain controlled range m order for the composition to be sprayable.
  • the present invention provides an improved sprayable coating composition which cures very quickly upon exposure to sunlight, ultraviolet light, as well as upon exposure to electron beams or other suitable energy source.
  • the composition of the present invention is made up predominantly of solids and is, preferably, substantially free of volatile organic solvents.
  • a coating composition m accordance with the present invention generally, comprises: from about 60 to about 99.9 percent by weight, based on the total weight of the composition, of a polyme ⁇ zable compound which comprises at least one acrylate; from about 0.5 to about 15 percent by weight, based on the total weight of the composition, of a photoinitiator which initiates a polymerization reaction in the composition when it is exposed to the requisite energy source; and from about 0 to about 40° o , by weight, based on the total weight of the composition, of a non-volatile solvent.
  • the present invention further contemplates the inclusion of a pigment or other visual effect adjuvant into the composition.
  • the adjuvant is present in an amount ranging from about 0.01° to about 95 % , by weight, based on the total weight of the composition.
  • the polymerizable compound may be selected from the group consisting of urethane acrylates, polyester acrylates, monoacrylates, diacrylates, triacrylates, polyacrylate and the like, and mixtures thereof.
  • the photoinitiator may be eliminated;
  • the present invention provides a sprayable coating composition, which is substantially free of volatile organic solvents and which is especially useful for coating wood, metal, stone or concrete or plastic articles.
  • the composition may be made up either as an opaque or a transparent coating composition.
  • the composition hereof is especially advantageous, as contrasted with the known coating compositions, m that it does not generate any significant organic volatile evaporative emission component during the curing process , while enabling the incorporation of a non-volatile organic solvent thereinto.
  • Curing is effected by a rapid polymerization reaction which is initiated by a photoinitiator component of the composition when it is exposed to an energy source, such as sunlight, ultraviolet light, or other natural or artificial ultraviolet light.
  • an energy source such as sunlight, ultraviolet light, or other natural or artificial ultraviolet light.
  • electron beam energy can be used to polymerize the acrylate. Substantially, the entire composition remains in place on the substrate during and after curing.
  • the coating composition of the present invention generally, comprises: from about 60% to about 99.9°, by weight, based on the total composition weight, of a polyme ⁇ zable compound which comprises an acrylate; from about 0 to about 40° o , by weight, based on the total weight of the composition of a non-volatile solvent or diluent; and from about 0.1 to about 15 percent, by weight, based on the total composition weight, of a photoinitiator which initiates a polymerization reaction m the composition when it is exposed to ultraviolet light.
  • the composition hereof includes from about 68 to about 84.9 percent of the polymerizable compound, from about 5% to about 25% of the solvent, and from about 0.1 to about 7 percent of the photoinitiator, by weight .
  • the coating composition hereof comprises 68 to 84 percent of a first t ⁇ acrylate 15 to 25 percent of a second monoacrylate, and 0.1 to about 7 percent of the photoinitiator.
  • non-reactive or non-volatile diluents include, for example, water; organic diluents, such as ketones, alcohols, ethers, petroleum distillates, hydrocarbon solvents, butylcellosolve, and the like, as well as mixtures thereof.
  • useful ketones are acetone methyl ethyl ketone and the like; useful alcohols include, alkanols, diols, triols, and the like, including methyl alcohol, ethyl alcohol, butane diol, trimethylolpropane, glycerol and the like.
  • Useful ethers include, for example, vinyl ether, ethyl ether, methyl ether and the like.
  • Useful hydrocarbon solvents include benzene, tolene, hexane, heptane and so forth, as well as mixtures thereof.
  • diluents include liquid triacrylates, polyesters, esters, and the like.
  • the incorporation of the diluent enables the viscosity of the composition to be lowered to a range of from about O.lcps to about 300cps at 25°C.
  • the viscosity when used with the appropriate photoinitiator, can range upward of to about 100,000cps.
  • the viscosity can range from about O.lcps to about 100,000cps at 25°C and still remain sprayable.
  • non-reactive diluents it is preferred to employ water, alcohols, ketones or ethers, as well as mixtures thereof (and most, preferably, acetone) .
  • the polymerizable compound may be selected from the group consisting of monoacrylates, diacrylates, triacrylates, polyacrylates, urethane acrylates, polyester acrylates, and the like, as well as mixtures thereof.
  • the polymerizable compound preferably, includes a mixture of acrylates.
  • Suitable compounds which may be used in the practice of the present invention include but are not limited to, trimethylolpropane triacrylate, alkoxylated trimethylolpropane triacrylate, such as ethoxylated or propoxylated trimethyolpropane triacrylate, 1,6-hexane diol diacrylate, isobornyl acrylate, aromatic and aliphatic urethane acrylates, vinyl acrylates, epoxy acrylates, ethoxylated bisphenol A diacrylates, trifunctional acrylic ester, unsaturated cyclic diones, polyester diacrylates, and mixtures of the above compositions.
  • the photoinitiator which is used in the composition of the present invention may be of the free radical or catiomc type. A combination of photoinitiators may be used.
  • Photo-initiators which are suitable for use m the practice of the present invention include, but are not limited to, l-phenyl-2- hydroxy-2-methyl-l-propanone, ol ⁇ go ⁇ 2-hydroxy-2 methyl-1- [4- (methylvmyl) phenyl] propanone ⁇ , 2-hydroxy 2-methyl 1-phenyl propan-1 one, bis (2, 6-d ⁇ methoxybenzoyl) -2, 4, 4- tnmethylpentyl phosphine oxide, 1-hydroxycyclohexyl phenyl ketone and benzophenone as well as mixtures thereof.
  • initiators include, for example, bis (n, 5, 2, 4- cyclopentadien -1-yl) -bis [2, 6 -d ⁇ fluoro-3- (lH-pyrol-1-yl) phenyl] titanium and 2-benzyl -2-N,N- dimethyl ammo -1- (4-morpholmophenyl) -1- butanone . Both of these compounds are commercially available and sold by C ⁇ BA under the names IRCACURE 784 DC and IRGACURE 369, respectively.
  • Still other useful photoinitiators include, for example, benzophenone, 2-methyl -1- [4 (methylthio) -2- morpholmopropan] - 1-one, 4- (2-hydroxy) phenyl -2-hydroxy -2-methylpropyl) ketone, 1-hydroxy cyclohexyl phenyl ketone benzophenone, (n-5,2,4- cyclopentadien -1-yl) [1,2,3,4,5, 6-n)- (1-methylethyl) benzene] -iron (+) hexafluorophosphate (-1), 2,2 -dimethoxy -2-phenyl-l-acetophen-one 2,4,6- trimethyl benzoyl-diphenyl phosphine oxide, benzoic acid, 4- (dimethyl ammo) -ethyl ether, as well as mixtures thereof.
  • photoinitiators include those sold by Sartomer under the name ESACURE, including the EB3, -,
  • a preferred coating composition hereof comprises 65 to 85 percent propoxylated trimethylolpropane triacrylate, 15 to 25 isobornyl acrylate, and 0.1 to about 7 percent of a photoinitiator which is a mixture of bis (2, 6-d ⁇ methylbenzoyl) 2, 4, 4-tr ⁇ methylpentyl phosphine oxide and 2-hydroxy- 2-methyl -1-phenyl-propan-l-one, sold commercially by CIBA-GE1GY under the Mark IRGACURE 1700 or IRGACURE CGI1700.
  • This photoinitiator enables both high pigment loading as well as sunlight cure.
  • a preferred pigmented formula m accordance with the present invention comprises 50 to 70 percent of the triacrylate, 1 to 30 percent of the isobornyl acrylate, from about 5 to about 30 percent of the diluent, and, 0.1 to 50 percent pigment solids, and 0.1 to 7 percent of the IRGACURE 1700 photoinitiator.
  • the present invention may be cured by natural sunlight, by medium pressure mercury arc lights, or by long wave ultraviolet light depending on the photoinitiator package used. Also, as noted, the polymerization may be electron beam initiated, thus, omitting the need for the photoinitiator.
  • pigment loading up to about 95° 0 , by weight, of the composition is possible, although not necessarily desirable because of economic reasons.
  • pigments and other visual effect materials including phosphorescent compounds, depending on the oil absorption factors.
  • Useful pigments and other visual effect materials include both organic and inorganic dyes, both natural and synthetic, as well as other naturally occurring materials, organic and inorganic pigments, etc.
  • Useful compounds include, for example, carbon black; titanium dioxide; phthalocyanate; azo dyestuffs; metal oxides, such as iron oxide; synthetic coloring agents, such as nitrosyl amines, benzoyl compounds, and the like; for pearlesence ground mica may be incorporated.
  • polycarbonates, naturally occurring dyes, chromates, molybdates and the like, as well as mixtures thereof may be included herewithm.
  • the pigment and/or visual effect material may be ground and, then, admixed with the coating composition simply by stirring or milling it into the composition or otherwise dispersing it thereinto the like.
  • the composition may have to be heated to a temperature of up to about 100°C, m order to incorporate the pigment and/or visual effect material into the composition.
  • the pigment typically, is it employed m an amount ranging from about 0.1% to about 80%, although up to about 95% is achievable.
  • the compound is present m an amount ranging from about 1% to about 50%.
  • the composition of the present invention is a significant improvement over the prior art coating compositions because of the fact that it does not contain any significant organic solvent which must be evaporated before curing is complete and its attendent environmental problems. Rather, the present invention includes low molecular weight polymerizable monomers and/or oligomers which are polymerized in place upon exposure to ultraviolet light. Therefore, the composition of the present invention is much less hazardous to the environment than the previously available compounds which included organic solvents which had to be evaporated into the atmosphere m order to cure the finish.
  • a low molecular weight mono or di-acrylate is used, preferably, as one component of the present composition. Possible methods of application include spraying, brushing, curtain coating, dipping, and rolling.
  • the formulation can be applied in repeated cycles .
  • composition of the present invention has the ability, under proper conditions, to be applied, cured, and sanded or burnished within the span of one minute and is then ready for repeated cycles. As such, five or ten coats can be applied in as many minutes.
  • the composition has the ability to control viscosity by the use of low molecular weight monomers which take the place of organic solvents but which also participate and contribute to final polymer properties.
  • the formulation can be used as a stain or sealant.
  • porous substrates such as wood, concrete or SMC speed of penetration is a direct function of viscosity. Therefore, by controlling the viscosity of the material, depth and speed of penetration before curing can be controlled.
  • the material polymerizes in and about the substrate providing adhesion thereto.
  • the preferred viscosity of the composition hereof is from about 2 centipoise to about 1200 centipoise to about 1500 at 25°C and preferably from about 2 to about 1200 centipoise at 25°C.
  • a silicone-based surfactant such as a siloxane or silane
  • siloxane or silane may be admixed herewith.
  • inorganic compounds maybe used as well; typically, the silicone is employed as a silane, corresponding to the formula:
  • R-Si-ORl where R and Rl are substituted or unsubstituted linear alkyl or alicyclic having from about 1 to 4 carbon atoms m the alkyl portion thereof.
  • Some useful silanes are for example, methyltrimethoxy silane, butyltrimethoxy silane, chlorpropylt ⁇ methoxy silane, glycidyl oxide methoxy silanes, and the like, as well as mixtures thereof.
  • Preferred compounds are glycidoxy methoxy silanes, such as that sold by Dow Corning under the name SILWET RC-73.
  • Other useful wetting agents include the siloxanes corresponding to the formula:
  • siloxane such as the polydimethyl siloxane fluids.
  • a preferred siloxane is methyloxysiloxane.
  • the silicone surfactant is used m an amount, by weight, based on the total composition, ranging from about 0.0001 percent to about 5.0 percent.
  • Halogenated surfactants are used to achieve high gloss and mar resistance.
  • Useful halogenated surfactants include fluoroaliphatic polymeric esters and alkyl alkoxylates. These halogenerated adjuvants are used m the same amounts as the silicone surfactants:
  • an acrylate or methacrylate ester derivative surfactants may be used.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Paints Or Removers (AREA)
  • Macromonomer-Based Addition Polymer (AREA)

Abstract

Une composition de revêtement apte à être pulvérisée est formulée à l'aide d'un ou plusieurs acrylates et d'un ou plusieurs photoamorceurs qui polymérisent la composition lorsqu'elle est exposée à la lumière ultraviolette. Du fait de l'utilisation de monomères et d'oligomères de faible poids moléculaire, la composition est pratiquement exempte de solvants organiques volatils, et les émissions de vapeurs sont, par conséquent, pratiquement éliminées au cours du durcissement. La composition comprend un diluant non réactif favorisant une plus grande plage de viscosités.
PCT/US1996/015464 1995-09-26 1996-09-26 Composition de finition durcissable a la lumiere ultraviolette et son procede d'utilisation WO1997045458A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU73742/96A AU7374296A (en) 1995-09-26 1996-09-26 Finishing composition which is curable by uv light and method of using same

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US55367995A 1995-09-26 1995-09-26
US08/553,679 1995-09-26

Publications (1)

Publication Number Publication Date
WO1997045458A1 true WO1997045458A1 (fr) 1997-12-04

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PCT/US1996/015464 WO1997045458A1 (fr) 1995-09-26 1996-09-26 Composition de finition durcissable a la lumiere ultraviolette et son procede d'utilisation

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AU (1) AU7374296A (fr)
WO (1) WO1997045458A1 (fr)

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001051533A1 (fr) * 2000-01-13 2001-07-19 Uv Specialties, Inc. Compositions de revetement du bois polymerisables aux uv
WO2001094478A3 (fr) * 2000-06-03 2002-07-18 Votteler Lackfabrik Gmbh & Co Agents de revetement durcissables aux uv, procede de realisation de revetements a partir de ces agents, et leur utilisation
US6541076B2 (en) 1999-12-20 2003-04-01 Patent Holding Company Method of priming SMC parts
US6897248B2 (en) 2000-01-13 2005-05-24 Allied Photochemical, Inc. UV curable ferromagnetic compositions
US6905735B2 (en) 1999-11-05 2005-06-14 Allied Photochemical, Inc. UV curable paint compositions and method of making and applying same
US6906114B2 (en) 2000-09-06 2005-06-14 Allied Photochemical, Inc. UV curable silver chloride compositions for producing silver coatings
US6946628B2 (en) 2003-09-09 2005-09-20 Klai Enterprises, Inc. Heating elements deposited on a substrate and related method
US6967042B2 (en) 1999-11-05 2005-11-22 Allied Photochemical, Inc. UV curable compositions for producing mar resistant coatings and method for depositing same
US6991833B2 (en) 1999-12-06 2006-01-31 Allied Photochemical, Inc. UV curable compositions for producing multilayer paint coatings
US7067462B2 (en) 1999-12-06 2006-06-27 Allied Photochemical, Inc. UV curable lubricant compositions
US7119129B2 (en) 2000-01-13 2006-10-10 Allied Photochemical, Inc. UV curable transparent conductive compositions
US7157507B2 (en) 1999-04-14 2007-01-02 Allied Photochemical, Inc. Ultraviolet curable silver composition and related method
US7323499B2 (en) 2000-09-06 2008-01-29 Allied Photochemical, Inc. UV curable silver chloride compositions for producing silver coatings
US7436115B2 (en) 1999-10-06 2008-10-14 Krohn Roy C Electroluminescent device
ES2319068A1 (es) * 2007-10-30 2009-05-01 Fepyr S.A. Sistema de revestimiento para el lacado de superficies.
WO2020234268A1 (fr) * 2019-05-20 2020-11-26 Brillux Gmbh & Co. Kg Procédé de revêtement d'une surface

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4721734A (en) * 1977-05-17 1988-01-26 Merck Patent Gesellschaft Mit Beschrankter Haftung Photosensitive hydroxylalkylphenones
US5453451A (en) * 1991-05-15 1995-09-26 Sokol; Andrew A. Finishing composition which is curable by UV light and method of using same

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4721734A (en) * 1977-05-17 1988-01-26 Merck Patent Gesellschaft Mit Beschrankter Haftung Photosensitive hydroxylalkylphenones
US5453451A (en) * 1991-05-15 1995-09-26 Sokol; Andrew A. Finishing composition which is curable by UV light and method of using same

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7157507B2 (en) 1999-04-14 2007-01-02 Allied Photochemical, Inc. Ultraviolet curable silver composition and related method
US7436115B2 (en) 1999-10-06 2008-10-14 Krohn Roy C Electroluminescent device
US6967042B2 (en) 1999-11-05 2005-11-22 Allied Photochemical, Inc. UV curable compositions for producing mar resistant coatings and method for depositing same
US6905735B2 (en) 1999-11-05 2005-06-14 Allied Photochemical, Inc. UV curable paint compositions and method of making and applying same
US6991833B2 (en) 1999-12-06 2006-01-31 Allied Photochemical, Inc. UV curable compositions for producing multilayer paint coatings
US7067462B2 (en) 1999-12-06 2006-06-27 Allied Photochemical, Inc. UV curable lubricant compositions
US6541076B2 (en) 1999-12-20 2003-04-01 Patent Holding Company Method of priming SMC parts
EP1272343A4 (fr) * 1999-12-20 2004-06-09 Patent Holding Co Procede d'amorcage de pieces de melange a mouler en feuille
WO2001051533A1 (fr) * 2000-01-13 2001-07-19 Uv Specialties, Inc. Compositions de revetement du bois polymerisables aux uv
US6897248B2 (en) 2000-01-13 2005-05-24 Allied Photochemical, Inc. UV curable ferromagnetic compositions
US7119129B2 (en) 2000-01-13 2006-10-10 Allied Photochemical, Inc. UV curable transparent conductive compositions
WO2001094478A3 (fr) * 2000-06-03 2002-07-18 Votteler Lackfabrik Gmbh & Co Agents de revetement durcissables aux uv, procede de realisation de revetements a partir de ces agents, et leur utilisation
US6906114B2 (en) 2000-09-06 2005-06-14 Allied Photochemical, Inc. UV curable silver chloride compositions for producing silver coatings
US7323499B2 (en) 2000-09-06 2008-01-29 Allied Photochemical, Inc. UV curable silver chloride compositions for producing silver coatings
US6946628B2 (en) 2003-09-09 2005-09-20 Klai Enterprises, Inc. Heating elements deposited on a substrate and related method
ES2319068A1 (es) * 2007-10-30 2009-05-01 Fepyr S.A. Sistema de revestimiento para el lacado de superficies.
WO2009056655A1 (fr) * 2007-10-30 2009-05-07 Fepyr, S.A. Système de revêtement pour le laquage d'une surface
WO2020234268A1 (fr) * 2019-05-20 2020-11-26 Brillux Gmbh & Co. Kg Procédé de revêtement d'une surface

Also Published As

Publication number Publication date
AU7374296A (en) 1998-01-05

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