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
  • 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
  • C08F222/36—Amides or imides
  • C08F222/40—Imides, e.g. cyclic imides
• • 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
  • C08F22/00—Homopolymers and 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
  • C08F22/36—Amides or imides
  • C08F22/40—Imides, e.g. cyclic imides
• • 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
  • C08F222/04—Anhydrides, e.g. cyclic anhydrides
  • C08F222/06—Maleic anhydride
• • 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
  • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
  • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
  • C08F290/06—Polymers provided for in subclass C08G
• • 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 photocurable compositions.
• the present invention relates to photocurable compositions that can be printed using an ink jet printer.
• Photocurable materials typically contain one or more polymerizable materials (for example, a mixture of free-radically polymerizable monomers and/or oligomers) and one or more photoinitiators.
• the productivity (that is, speed) of processes utilizing photocurable materials depends, at least in part, on the amount of actinic radiation (that is, radiation having at least one wavelength in the ultraviolet or visible region of the spectrum) required to achieve a desired degree of cure (that is, polymerization and/or crosslinking) of the photocurable material, insufficient curing may result in inadequate surface cure of the material (for example, a printed image) and/or poor curing of the full thickness of the layer (that is, poor through cure), which may cause poor adhesion of the cured material to the substrate on which it is printed and/or handling problems. Due to the nature of typical commercial printing processes and the presence of light absorbing colorants, cure speed and through cure are typically important variables in formulating and utilizing photocurable inks.
• Photocurable inks are typically formulated by including colorant in the photocurable composition.
• Photocurable inks may offer advantages over conventional inks. For example, uncured ink images printed using photocurable inks can typically be made permanent (that is, fixed) by exposure to actinic radiation. Immediately after fixing the image, it may typically be handled without risk of damage (for example, by smearing). The problems of insufficient and/or slow curing may be particularly troublesome, if photocurable material is applied to porous materials (for example, woven or nonwoven fabrics).
• penetration of the photocurable material into the porous material may result in a relatively thick layer of photocurable material and/or attenuation of the amount of actinic radiation that is available for curing the full thickness of the photocurable material.
• the present invention provides a photocurable composition
• a photocurable composition comprising: at least one free-radically polymerizable material; at least one benzophenone derivative; at least one acylphosphine oxide; and at least one maleimide having the formula:
• each R2 independently represents a divalent organic group or a covalent bond
• n is 1, 2, or 3.
• the present invention provides a method for applying a photocurable composition to a substrate comprising: providing a substrate; providing a photocurable composition comprising: at least one free-radically polymerizable material; at least one benzophenone derivative; at least one acylphosphine oxide; and at least one maleimide having the formula:
• an article comprises a substrate having thereon a reaction product of a photocurable composition comprising: at least one free-radically polymerizable material; at least one benzophenone derivative; at least one acylphosphine oxide; and at least one maleimide having the formula:
• each R2 independently represents a divalent organic group or a covalent bond, and n is 1, 2, or 3.
• the photocurable compositions further contain at least one colorant.
• the photocurable compositions are useful for Inkjet printing applications.
• Photocurable compositions of the present invention typically comprise at least one, preferably a mixture of two or more, free-radically polymerizable materials, the specific choice of free-radically polymerizable materials being determined by the specific properties sought (that is, hardness, toughness, flexibility).
• the total amount of free-radically polymerizable material(s) present in photocurable compositions of the present invention is in a range of from 25 percent by weight to 98 percent by weight free-radically polymerizable material(s), based on the total weight of the photocurable composition, although other amounts may be used.
• the total amount of free-radically polymerizable material(s) is in a range of from 30 percent by weight to 95 percent by weight, more preferably from 50 percent by weight to 90 percent by weight, based on the total weight of the photocurable composition.
• Free-radically polymerizable materials include, for example, free-radically polymerizable monomers and/or oligomers, either or both of which may be monofunctional or multifunctional. Free-radically polymerizable materials suitable for use in practice of the present invention are well known in the art, and include those described in, for example, U.S. Pat. Nos. 5,395,863 (Burns et al.); and 5,275,646 (Hudd et al.); and XLS. Pat. Publication No. 2002/0086914 Al (Lee et al), published July 4, 2002.
• Exemplary free-radically polymerizable monomers include styrene and substituted styrenes (for example, ⁇ -methylstyrene); vinyl esters (for example, vinyl acetate); vinyl ethers (for example, butyl vinyl ether); N-vinyl compounds (for example, N-vinyl-2- pyrrolidone, N-vinylcaprolactam); acrylamide and substituted acrylamides (for example,
• N,N-dialkylacrylamide N,N-dialkylacrylamide
• acrylates and/or methacrylates that is, collectively referred to herein as (meth)acrylates
• (meth)acrylates) for example, isooctyl (meth)acrylate, nonylphenol ethoxylate (meth)acrylate, isononyl (meth)acrylate, diethylene glycol (meth)acrylate, isobornyl (meth)acrylate, 2-(2-ethoxyethoxy)ethyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, lauryl (meth)acrylate, butanediol mono(meth)acrylate, ⁇ -carboxyethyl
• (meth)acrylate isobutyl (meth)acrylate, cycloaliphatic epoxide, ⁇ -epoxide, 2-hydroxyethyl (meth)acrylate, (meth)acrylonitrile, maleic anhydride, itaconic acid, isodecyl (meth)acrylate, dodecyl (meth)acrylate, n-butyl (meth)acrylate, methyl (meth)acrylate, hexyl (meth)acrylate, (meth)acrylic acid, N-vinylcaprolactam, stearyl (meth)acrylate, hydroxy functional polycaprolactone ester (meth)acrylate, hydroxyethyl (meth)acrylate, hydroxymethyl (meth)acrylate, hydroxypropyl (meth)acrylate, hydroxyisopropyl (meth)acrylate, hydroxybutyl (meth)acrylate, hydroxyisobutyl (meth)acrylate, t
• Exemplary commercially available free-radically polymerizable oligomers include those acrylated oligomers available under the trade designation “EBECRYL” from UCB Chemicals, Smyrna, Georgia (for example, “EBECRYL 220", “EBECRYL 80", “EBECRYL 230", “EBECRYL 244", “EBECRYL 284", “EBECRYL 8402", “EBECRYL 5129”, “EBECRYL 4833”, “EBECRYL 4835”, or “EBECRYL 8301”), and acrylated oligomers available from Sartomer Company, Exton, Pennsylvania (for example, acrylated oligomers having the trade designations "CN501", “CN502", “CN550”, or “CN551").
• free-radically polymerizable multifunctional monomers and oligomers are di- or tri-functional, and are preferably present in photocurable compositions of the present invention in an amount in a range of from 1 weight percent to 70 weight percent, more preferably in an amount in a range of from 10 weight percent to 60 weight percent, based on the total weight of the photocurable composition.
• Photocurable compositions of the present invention typically include at least one benzophenone derivative (that is, a compound having the benzophenone skeletal structure).
• benzophenone derivatives and methods for making them are well known in the art, and are described in, for example, U.S. Pat. No. 6,207,727 (Beck et al.).
• Exemplary benzophenone derivatives include symmetrical benzophenones (for example, benzophenone, 4,4'-dimethoxybenzophenone, 4,4'-diphenoxybenzophenone, 4,4'-diphenylbenzophenone, 4,4'-dimethylbenzophenone, 4,4-dichlorobenzophenone) ; asymmetric benzophenones (for example, chlorobenzophenone, ethylbenzophenone, benzoylbenzophenone, bromobenzophenone); and free-radically polymerizable benzophenones (for example, acryloxyethoxybenzophenone).
• Benzophenone itself is inexpensive, and may be preferable if cost is a factor.
• Polymerizable benzophenones may be useful if residual odor or volatiles are a concern, and may be preferable for those applications as they become covalently incorporated into the composition during cure.
• Photocurable compositions of the present invention typically include at least one acylphosphine oxide.
• Acylphosphine oxides and methods for making them are well known in the art and are described in, for example, U.S. Pat. No. 4,710,523 (Lechtkien et al.).
• acylphosphine oxides include 2,4,6- trimethylbenzoyldiphenylphosphine oxide (for example, as available under the trade designation "LUCIRL TPO” from BASF Corporation, Mount Olive, New Jersey), and bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide (for example, as available under the trade designation "IRGACURE 819” from Ciba Specialty Chemicals, Tarrytown, New York).
• Photocurable compositions of the present invention typically include at least one maleimide having the formula:
• each R2 independently represents a divalent organic group or a covalent bond, and n is 1, 2, or 3.
• Exemplary divalent groups include substituted or unsubstituted alkylene (for example, alkylene having from 1 to 18 carbon atoms), substituted or unsubstituted arylene (for example, arylene having from 6 to 18 carbon atoms), substituted or unsubstituted aralkylene (for example, aralkylene having from about 7 to about 19 carbon atoms), and substituted or unsubstituted alkarylene (for example, alkarylene having from 7 to 19 carbon atoms).
• substituted or unsubstituted alkylene for example, alkylene having from 1 to 18 carbon atoms
• substituted or unsubstituted arylene for example, arylene having from 6 to 18 carbon atoms
• substituted or unsubstituted aralkylene for example, aralkylene having from about 7 to about 19 carbon atoms
• substituted or unsubstituted alkarylene for example, alkarylene having from 7 to 19 carbon atom
• the divalent group or groups may independently be substituted with one or more additional groups attached to and/or within the skeleton of the divalent group (for example, alkyl, halo, oxo, thia, oxa, aza, hydroxy, alkoxy, thioalkoxy, acyloxy).
• maleimides include aliphatic maleimides (for example, N- methylmaleimide, N- ethylmaleimide, N-propylmaleimide, N-n-butylmaleimide, N-tert- butylmaleimide, N-pentylmaleimide, N-hexylmaleimide, N-laurylmaleimide, 2- maleimidoethyl ethyl carbonate, or 2-maleimidoethyl isopropyl carbonate); alicyclic maleimides (for example, N-cyclohexylmaleimide); aromatic maleimides (for example, N- 2-methylphenylmaleimide, N-(2-ethylphenyl)maleimide, N-(4- hydroxyphenyl)maleimide); aliphatic bismaleimides (for example, N,N'- methylenebismaleimide, N,N'-ethylenebismaleimide, N,N'- trimethylenebismaleimide, N,
• the maleimide is preferably non-polymeric and/or has a molecular weight of less than 1000 grams per mole.
• the benzophenone derivative, acylphosphine oxide, and maleimide are preferably selected such that they are soluble in the photocurable composition and are substantially not reactive with other components of the photocurable composition in the absence of actinic radiation.
• the combined amount of benzophenone derivative, acylphosphine oxide, and maleimide is in a range of from 0.01 to 20 weight percent, preferably in a range of from 3 to 12 weight percent, more preferably in a range of from 4 to 10 weight percent, based on the combined weight of polymerizable material, benzophenone derivative, acylphosphine oxide, and maleimide that is present.
• the amounts of benzophenone derivative and acylphosphine oxide may be any amounts falling within the abovementioned limitation, but preferably the weight ratio of benzophenone derivative to acylphosphine oxide is in a range of from 1:5 to 10:1. More preferably, the weight ratio of 5 benzophenone derivative to acylphosphine oxide is in a range of from 1:3 to 5:1.
• the maleimide may be any amount falling within the abovementioned limitation, but preferably the amount of maleimide is in a range of from 0.01 percent by weight to 5 percent by weight, more preferably in a range of from 0.5 percent by weight to 2.5 percent by weight, more preferably in a range of from 0.8 percent by weight to 2 0 percent by weight based on the combined weight of polymerizable material, benzophenone derivative, acylphosphine oxide, and maleimide that is present.
• Sensitizers, co-initiators, and amine synergists can, optionally, be included in photocurable compositions of the present invention in order to improve the curing rate.
• Examples include isopropylthioxanthone, ethyl 4-(dimethylamino)benzoate, 2-ethylhexyl
• Photocurable compositions of the present invention may, optionally, include one or more colorants.
• Useful colorants include dyes and pigments, which may be used alone or in any combination.
• Useful dyes and pigments may be of any color, and are well known in the art, for example, as described in U.S. Pat. Nos. 6,294,592 (Herrmann et al.) and 0 6,114,406 (Caiger et al.).
• the colorant comprises at least one pigment.
• the amount of optional colorant(s) used in photocurable compositions of the present invention is typically less than 25 volume percent based on the total volume of the ink composition, although higher volume percentages may be used.
• the colorant(s), if present is in an amount in a range of from 0.1 percent by volume to 15 percent by volume, based on 5 the total volume of the ink composition.
• Photocurable compositions of the present invention may, optionally, contain solvent.
• Solvent may consist of one or more non-reactive diluent materials that may serve, for example, to lower the viscosity of photocurable composition, lower the surface tension of the photocurable composition, and/or dissolve components in the photocurable
• any amount of solvent may be utilized.
• small quantities of solvent may be added as described, for example, in PCT Publication No. WO 02/38687 Al (Ylitalo et al.), published May 16, 2002.
• the amount of optional solvent incorporated is kept to a minimum, preferably essentially none (for example, less than one weight percent).
• Exemplary solvents include water; alcohols such as isopropyl alcohol (IP A) or ethanol; ketones such as methyl ethyl ketone, cyclohexanone, or acetone; aromatic hydrocarbons; isophorone; butyrolactone; N-methyl pyrrolidone; tetrahydrofuran; ethers such as lactates, acetates, and the like; ester solvents such as propylene glycol monomethyl ether acetate (PM acetate), diethylene glycol ethyl ether acetate (DE acetate), ethylene glycol butyl ether acetate (EB acetate), dipropylene glycol monomethyl acetate (DP acetate), iso- alkyl esters, isohexyl acetate, isoheptyl acetate, isooctyl acetate, isononyl acetate, isodecyl acetate, isododecyl a
• additives may, for example, include one or more of colorants, slip modifiers, thixotropic agents, foaming agents, antifoaming agents, flow or other rheology control agents, waxes, oils, plasticizers, binders, antioxidants, stabilizers, electrical conductive agents, fungicides, bactericides, organic and/or inorganic filler particles, leveling agents, opacifiers, antistatic agents, and/or dispersants.
• colorants include one or more of colorants, slip modifiers, thixotropic agents, foaming agents, antifoaming agents, flow or other rheology control agents, waxes, oils, plasticizers, binders, antioxidants, stabilizers, electrical conductive agents, fungicides, bactericides, organic and/or inorganic filler particles, leveling agents, opacifiers, antistatic agents, and/or dispersants.
• Photocurable compositions of the present invention may be cured, for example, by exposure to actinic radiation (that is, radiation having a wavelength in the ultraviolet or visible region of the spectrum).
• Suitable sources of actinic radiation include mercury lamps, xenon lamps, carbon arc lamps, tungsten filament lamps, lasers, electron beam energy, sunlight, microwave driven lamps, and the like.
• the source of radiation is a medium pressure mercury lamp.
• Photocurable compositions of the present invention may be applied (for example, coated, printed) onto a substrate. Exemplary application methods include spraying, dip coating, bar coating, curtain coating, roll coating, gravure coating.
• the photocurable composition may be printed onto a substrate.
• Useful printing techniques include those known in the graphic arts including, for example, screen printing, gravure printing, flexography, lithography, or ink jet printing.
• the photocurable compositions may be printed, for example, to form graphic elements, text items, continuous layers, bar codes, or other features.
• photocurable compositions of the present invention can be applied to ' a substrate using an ink jet printhead.
• the ink jet printhead may be operated at an elevated temperature (for example, piezo printing).
• the photocurable composition has a viscosity of less than or equal to 35 millipascal-seconds at the ink jet printhead operating temperature (for example, less than or equal to 80 C) and shear conditions (for example, 800 per second).
• Exemplary ink jet printing methods include thermal ink jet, piezo ink jet, continuous ink jet, and bubble jet techniques. Piezo Inkjet printing may be especially useful in some embodiments of the present invention.
• curable ink jet printable compositions and methods for printing them may be found in, for example, U.S. Pat. Publication No. 2002/0085056 (Ylitalo), published July 4, 2002.
• Photocurable compositions of the present invention may be applied to (for example, coated, printed) a substrate.
• Useful substrates may be rigid or flexible.
• Exemplary substrates include wood, metal (including foils), paper (including resin coated papers), textiles (including woven or nonwoven fabrics), polymer films (including vinyl films (for example, those marketed under the trade designation "SCOTCHCAL” by 3M Company), multilayered films (for example, as described in U.S. Pat. Nos. 6,180,228 (Bruno et al.)), retroreflective films (for example, as described in U.S. Pat. Nos. 6,350,035
• Photocurable compositions in the following examples were prepared by placing all ingredients in an amber glass jar and allowing the mixture to roll on a roller mill overnight to provide a completely homogeneous solution.
• Photocurable compositions were coated onto a 15-centimeter (cm) x 20 cm piece of SUBSTRATE C using a number 8 wire wound rod (obtained from RD Specialties, Webster, New York) resulting in a nominal coating thickness of from 8 to 10 micrometers.
• the coated films were cured in one pass using an RPC model QC120233 AN/DR UV processor, obtained from RPC Industries, Plainfield, Illinois.
• the minimum speed of the processor belt was 30 feet per minute (9 meters per minute).
• the processor was equipped with two medium pressure mercury lamps with an intensity of 400 watts per inch (160 watts per centimeter). The coating was considered cured if it passed both of the following tests:
• Cotton applicator test a cotton tipped applicator was rubbed ten times by hand with firm pressure against the coating (or until smearing of the coating was observed). If no smearing was observed and no cotton fibers transferred to the coating, then the cotton applicator test was passed.
• Thumb print test a thumb was pressed with moderate pressure against the coating, twisted 90 degrees, then lifted off the coating. If no marring of the coating surface was visually discerned, then the thumb print test was passed.
• a solution was prepared consisting of 10 parts of stock solution, 0.4 parts of benzophenone (obtained from UCB Radcure), and 0.4 parts of 2,4,6- trimethylbenzoyldiphenylphosphine oxide photoinitiator (obtained under the trade designation "CfflVACURE TPO” from Chitec Chemical Company, Taipei, Taiwan).
• COMPARATIVE EXAMPLE B A solution was prepared consisting of 98.2 parts of stock solution and 1.8 parts of BM1. EXAMPLES 1 - 7 Maleimides BM1 and NMM were added in amounts specified in Table 1 (below) to seven solutions identical to that of Comparative Example A.
• a yellow millbase was prepared by pre-dissolving 25 parts of a dispersant (obtained under the trade designation "SOLSPERSE 32000" from Zeneca, Inc., Wilmington, Delaware) in 35 parts tetrahydrofurfuryl acrylate (obtained from Sartomer Company) and then adding 40 parts of yellow pigment, obtained under the trade designation "FANCHON FAST YELLOW Y-5688" from Bayer Corporation, Pittsburgh, Pennsylvania. Initial wetting of the pigment was accomplished using high shear mixing. Next, the dispersion was subjected to high energy milling in order to reduce the particle size to less than 0.5 microns.
• a dispersant obtained under the trade designation "SOLSPERSE 32000" from Zeneca, Inc., Wilmington, Delaware
• tetrahydrofurfuryl acrylate obtained from Sartomer Company
• Initial wetting of the pigment was accomplished using high shear mixing.
• the dispersion was subjected to high energy milling in order to reduce the particle size to less than
• a photocurable ink formulation was prepared by combining 7.5 parts of the yellow millbase, 82.5 parts of stock solution, 5 parts of benzophenone, and 5 parts of bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide (that is, "IRGACURE 819") in a jar, and placing the jar on a roller mill overnight to provide a homogenous photocurable ink.
• BM1 and NMM were added in amounts specified in Table 2 (below) to two inks identical to that of Comparative Example C.
• EXAMPLE 10 An inkjet ink was prepared in a manner as described in Comparative Example C, except using the following amounts of the components: 185 parts of stock solution, 15 parts of yellow millbase, 10 parts of benzophenone, 10 parts bis(2,4,6- trimethylbenzoyl)phenylphosphine oxide, and 0.1 parts N-methylmaleimide.
• the ink viscosity was measured at 25 C using a Model No. CVO 12O HR NF rheometer (cup and bob configuration, CS C25 cup), obtained from Bohlin Instruments, Ltd., East Brunswick, New Jersey.
• the ink viscosity was 26 millipascal-seconds at shear rate of 800 per second.
• the ink surface tension was measured using a Kruss tensiometer, obtained from Kruss USA, Charlotte, North Carolina, according to the Wilhemy plate method.
• the ink surface tension at 25 C was 30.4 millinewtons per meter.
• EXAMPLES 11 - 16 A variety of substrates were mounted onto a translatable X-Y stage and printed at a resolution of 300 dots per inch (760 dots per cm) by 300 dots per inch (760 dots per cm) using a 256 nozzle piezo printhead (obtained under the trade designation "GALAXY” from Spectra, Inc., Hanover, New Hampshire) equipped with a deaeration lung and operating at a printhead temperature of 55 C.
• the printhead settings were: 1.25 kilohertz frequency, 145 volts driving voltage, and pulse width of 8 microseconds.
• the printed ink was cured using a UV processor (obtained from Fusion UV Systems, Gaithersburg, Maryland) equipped with a D-type lamp delivering a single pass dosage of 20O millijoules per square centimeter. The results are reported in Table 3 (below).

Landscapes

• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Health & Medical Sciences (AREA)
• Polymers & Plastics (AREA)
• Medicinal Chemistry (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Wood Science & Technology (AREA)
• Life Sciences & Earth Sciences (AREA)
• Materials Engineering (AREA)
• Engineering & Computer Science (AREA)
• Inks, Pencil-Leads, Or Crayons (AREA)
• Polymerisation Methods In General (AREA)
• Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
• Ink Jet Recording Methods And Recording Media Thereof (AREA)
• Paints Or Removers (AREA)
• Materials For Photolithography (AREA)

Priority Applications (4)

Applications Claiming Priority (2)

Publications (1)

Family

ID=31494683

Family Applications (1)

Country Status (8)

Families Citing this family (33)

Citations (5)

Family Cites Families (23)

• 2002
  • 2002-08-08 US US10/214,619 patent/US20040029044A1/en not_active Abandoned
• 2003
  • 2003-06-17 GB GB0500794A patent/GB2406572B/en not_active Expired - Fee Related
  • 2003-06-17 JP JP2004527574A patent/JP4272156B2/ja not_active Expired - Fee Related
  • 2003-06-17 CN CNB038189046A patent/CN1307221C/zh not_active Expired - Fee Related
  • 2003-06-17 WO PCT/US2003/019136 patent/WO2004014970A1/en not_active Ceased
  • 2003-06-17 DE DE10393025T patent/DE10393025T5/de not_active Ceased
  • 2003-06-17 AU AU2003282345A patent/AU2003282345A1/en not_active Abandoned
  • 2003-06-17 KR KR1020057002239A patent/KR101009124B1/ko not_active Expired - Fee Related

Patent Citations (5)

Non-Patent Citations (2)

Also Published As

Similar Documents

Legal Events