WO2001034671A1 - Composition de resine pouvant etre traitee par rayonnement ultraviolet et matiere d'impression a jet d'encre comportant un film a base de cette composition - Google Patents

Composition de resine pouvant etre traitee par rayonnement ultraviolet et matiere d'impression a jet d'encre comportant un film a base de cette composition Download PDF

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WO2001034671A1
WO2001034671A1 PCT/JP2000/007898 JP0007898W WO0134671A1 WO 2001034671 A1 WO2001034671 A1 WO 2001034671A1 JP 0007898 W JP0007898 W JP 0007898W WO 0134671 A1 WO0134671 A1 WO 0134671A1
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group
weight
ultraviolet
resin composition
monomer
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PCT/JP2000/007898
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English (en)
Japanese (ja)
Inventor
Toshiya Seko
Maomi Fujimori
Yasuo Kitani
Fujio Matsuishi
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Mitsubishi Chemical Corporation
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Priority to AU13041/01A priority Critical patent/AU1304101A/en
Publication of WO2001034671A1 publication Critical patent/WO2001034671A1/fr

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    • 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
    • C08F2/00—Processes of polymerisation
    • C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • B41M5/50—Recording sheets characterised by the coating used to improve ink, dye or pigment receptivity, e.g. for ink-jet or thermal dye transfer recording
    • B41M5/52—Macromolecular coatings
    • B41M5/5209—Coatings prepared by radiation-curing, e.g. using photopolymerisable compositions
    • 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
    • C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
    • C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
    • 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
    • C08F271/00—Macromolecular compounds obtained by polymerising monomers on to polymers of nitrogen-containing monomers as defined in group C08F26/00
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
    • C08L51/003—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
    • 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
    • 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
    • G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers

Definitions

  • the present invention relates to an ultraviolet curable resin composition.
  • the present invention relates to a film suitable for use in recording with an aqueous ink jet ink and an ultraviolet curable composition capable of forming a recording material having the same.
  • the ink used here usually contains a water-soluble dye and water or a small amount of alcohol as a solvent. Therefore, if the printing surface is hydrophobic, the ink may be repelled without being absorbed, or the drying may be delayed, causing problems such as transfer and contamination of the periphery.
  • a coating made of a water-soluble polymer such as starch, gelatin, polyvinylpyrrolidone, polyvinyl alcohol, cellulose derivative, sodium polyacrylate, etc. is applied on the substrate surface. It has been proposed to form or mix inorganic or organic particles into the surface to make it porous. However, these methods have insufficient water resistance, such as print bleeding when water droplets adhere to the printing surface.
  • a method was developed to prevent ink re-elution by forming an ion complex with a water-soluble dye, which often has anionic groups such as sulfone groups, and a cationic substance. ing. Since the cationic substances used here are very hydrophilic, they can be used for substances other than water or highly hydrophilic solvents. Is difficult to dissolve, and there is a problem that such a solvent is necessary in order to use a cationic substance in a composition.
  • a coating liquid is prepared by dissolving and mixing the above-mentioned water-soluble polymer, porous material, cationic material, and the like in a solvent. It is carried out in such a manner that it is coated on the substrate and then dried and / or cured by ultraviolet rays (Japanese Patent Application Laid-Open No. 9-245359, Japanese Patent Application Laid-Open No. 9-209609). In this case, since the coating liquid contains a solvent such as water, it was necessary to provide a drying step.
  • An object of the present invention is to provide a recording material capable of imparting excellent printing characteristics, water resistance after printing, and moisture resistance when an aqueous ink is used, and an ultraviolet light capable of providing such a recording material.
  • An object of the present invention is to provide a curable resin composition. Disclosure of the invention
  • the present inventors have conducted various studies to solve the above problems, and as a result, have found that these problems can be solved by using a composition having a specific composition, and have completed the present invention. That is, the gist of the present invention is a composition containing the following components (a) to (d), wherein component (d) is 100 parts by weight in total of components (a) and (b). 0 to 55 parts by weight with respect to the ultraviolet curable resin composition.
  • FIG. 1 is an example of an optical recording medium having a recording layer based on the composition of the present invention.
  • Reference numerals in the figure, 1 denotes an optical recording medium
  • 12 denotes a substrate
  • 13 denotes a recording layer mainly composed of a dye
  • 14 denotes a metal reflective layer provided in close contact with the recording layer
  • 15 denotes protection.
  • Layer 17 is a recording surface layer (ink receiving layer) formed from the composition of the present invention.
  • the hydrophilic acrylic monomer as the component (a) constituting the composition of the present invention can be used without any particular limitation as long as it is a monofunctional acrylic monomer having a hydrophilic group.
  • hydrophilic acrylic monomer means that the solubility in water is 1 g / 100 g or more, among which 5 g / 100 g or more, particularly 10 g / 100 g or more. g / 100 g or more is preferable.
  • hydrophilic group examples include a hydroxyl group, an acid amide group, a morpholino group, an alkoxy group having 1 to 4 carbon atoms, a tetrahydrofurfuryl group, and a glycidyl group.
  • hydrophilic acryl-based monomer examples include hydroxyxethyl acrylate, 1-hydroxypropyl acrylate, 2-hydroxypropyl acrylate, 1-hydroxybutyl acrylate, and 4-hydroxybutyl acrylate.
  • hydroxy cypentyl acrylate 2-hydroxy-1-phenoxypropyl acrylate, 2-hydroxy-3-butoxypropyl acrylate, 2-hydroxy_3-methoxypropyl
  • a hydroxyl group such as acrylate, diethylene glycol monoacrylate, triethylene glycol monoacrylate, polyethylene glycol monoacrylate, dipropylene glycol monoacrylate, polypropylene glycol monoacrylate, and glycerin monoacrylate.
  • hydrophilic acrylic monomers may be used alone or in combination of two or more.
  • Esters of acrylic acid and acryloyl morpholine having a structure represented by the following general formula (2) or (3) are preferable from the viewpoints of ink absorbency and solubility of other components, and more preferably 4-hydrazine.
  • Roxybutyl acrylate and acryloyl morpholine are preferable from the viewpoints of ink absorbency and solubility of other components, and more preferably 4-hydrazine.
  • Roxybutyl acrylate and acryloyl morpholine When 4-hydroxybutyl acrylate and acryloyl morpholine are used, the weight ratio of 4-hydroxy butyl acrylate / acryloyl morpholine is 10/90 to 90/1. A range of 0 is preferred.
  • the ratio of 4-hydroxyheptyl acrylate is 10 or less, the solubility of other components is poor, and when it is 90 or more, ink absorbency may be poor.
  • the ratio of acryloylmorpholine is 90 or more, the water resistance of the ink is poor, and when the ratio is 10 or less, the film hardness may decrease.
  • the cationic copolymer constituting the component (b) is a cationic copolymer containing a quaternary nitrogen, and preferably contains a structural unit derived from a quaternary ammonium salt-containing acryl-based monomer. It is particularly preferable to use a cationic copolymer containing a structural unit represented by the following general formula (1).
  • R 1 hydrogen atom or methyl group
  • A oxygen atom or imino group
  • R 2 —CH 2 —CH (OH) — CH 2 — group or alkylene group having 2 to 5 carbon atoms
  • R 3 and R 4 alkyl groups having 1 to 4 carbon atoms which may be the same or different
  • R 5 an alkyl group having 1 to 10 carbon atoms, an aryl group, an aralkyl group,
  • X— a halogen ion or an alkyl sulfate ion having 1 to 4 carbon atoms
  • the structural unit represented by the general formula (1) is usually contained in an amount of 21 to 95 parts by weight, preferably 25 to 90 parts by weight, based on the cationic copolymer.
  • the content of the structural unit represented by the general formula (1) is more than 95% by weight, the resulting cationic copolymer has too high hydrophilicity, and the solubility in the hydrophilic acrylic monomer is low.
  • it is less than 20% by weight the water resistance of the ink may deteriorate.
  • the cationic copolymer containing the structural unit represented by the general formula (1) is obtained by copolymerizing a monomer having the structure represented by the general formula (1) with another copolymerizable monomer by a conventional method.
  • the solubility of the component (a) in the hydrophilic acrylic monomer can be controlled. Is possible.
  • the cationic copolymer containing the structural unit represented by the general formula (1) has, in addition to the monomer having the structure represented by the general formula (1), an alkyl chain having 1 to 18 carbon atoms.
  • the structural unit derived from the (meth) acrylic acid ester monomer is usually contained in the cationic copolymer in an amount of 5 to 79% by weight, preferably 10 to 75% by weight. If this content exceeds 79% by weight, the hydrophilicity of the resulting cationic copolymer will decrease, and the ink absorption and water resistance will deteriorate. If it is less than 5% by weight, the ink will have poor moisture resistance.
  • Containing a structural unit derived from a (meth) acrylic acid ester monomer having an alkyl chain having 1 to 18 carbon atoms facilitates the solubility of the component (a) in the hydrophilic acrylic monomer. Can be controlled.
  • Examples of the (meth) acrylate monomer having an alkyl group having 1 to 18 carbon atoms include methyl (meth) acrylate, ethyl (meth) acrylate, i-butyl (meth) acrylate, and t-butyl (meth).
  • Acrylate, cyclohexyl examples thereof include (meth) acrylate, 2-ethylhexyl (meth) acrylate, lauryl (meth) acrylate, and stearyl (meth) acrylate, with cyclohexyl (meth) acrylate and i-butyl (meta) being preferred.
  • At least one selected from the group consisting of a hydroxyl group, a morpholino group, and an alkoxy group having 1 to 4 carbon atoms for the purpose of further improving ink absorbency, moisture resistance, and solubility in a hydrophilic acrylic monomer. It is preferable to copolymerize a structural unit derived from a hydrophilic (meth) acrylic monomer or dimethylacrylamide. Their hydrophilicity
  • the unit derived from the (meth) acrylic monomer is preferably contained in the cationic copolymer in an amount of 5 to 70% by weight, more preferably 10 to 60% by weight. If the content exceeds 70% by weight, the resulting cationic copolymer will have too high a hydrophilicity, and the solubility of the component (a) in the hydrophilic acrylic monomer will be poor or will be produced. If the hydrophilicity of the coating becomes too high, the water resistance tends to deteriorate.
  • the hydrophilic (meth) acrylic monomer refers to a (meth) acrylic monomer having a solubility in water of lg / 100 g or more, and in particular, 5 g / 100 g or more, especially 100 g / 100 g or more is preferable.
  • Hydrophilic (meth) acrylic monomers that can be used in the present invention include hydroxyethyl (meth) acrylate, 1-hydroxypropyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, and 1-hydroxybutyl.
  • Highly polar monomers such as (meth) acrylate, glycidyl (meth) acrylate, and tetrahydrofurfuryl (meth) acrylate are exemplified.
  • preferred are acryloyl morpholine, 4-hydroxybutyl (meth) acrylate, hydroxypropyl (meth) acrylate, hydroxyethyl (methyl) acrylate, dimethyl acrylamide, and getyl acrylamide.
  • dimethyl acrylamide is more preferred.
  • the cationic copolymer constituting the composition of the present invention has a solubility in the component (a) of 5%.
  • the weight average molecular weight of the cationic copolymer constituting the composition of the present invention is usually from 5,000 to 500,000, preferably from 10,000 to 100,000.
  • the weight-average molecular weight (hereinafter abbreviated as “Mw”) is a value measured by gel permeation chromatography (GPC) using polyoxyethylene as a standard substance. (It is preferable to use Wako Beads G-40, G-50, etc. as the column.)
  • the Mw of the cationic copolymer is higher than 500,000, the viscosity of the composition is high, and the handleability is deteriorated. If the Mw is less than 5,000, the ink absorbency and moisture resistance may be deteriorated.
  • the quaternary ammonium base in the structural unit derived from the monomer represented by the general formula (1) forms an ion complex with the anion dye in the ink, improves water resistance, and improves the molecular weight. It is considered that by setting the value to 5,000 to 500,000, the mobility of the cation portion is reduced, thereby preventing ink bleeding at high temperature and high humidity.
  • the content ratio of the hydrophilic acrylic monomer of the component (a) and the cationic copolymer of the component (b) in the composition of the present invention is 40 / (weight ratio of (a) / (b)). It needs to be in the range of 60 to 95/5, and more preferably 50/50 to 85/15.
  • the photopolymerization initiator of the component (c) constituting the composition of the present invention a compound having a property of generating a free radical (radical) by dissociation by active energy rays such as light and ultraviolet rays is used.
  • active energy rays such as light and ultraviolet rays
  • photopolymerization initiators may be used alone, two or more of them may be used in combination, or a photosensitizer may be used in combination.
  • the amount of the photopolymerization initiator to be used is generally 0.1 to 10 parts by weight, preferably 0.5 to 5 parts by weight, per 100 parts by weight of the component (a). If the amount of the photopolymerization initiator is more than 10 parts by weight, the strength of the obtained film is reduced. On the other hand, if it is less than 0.1 part by weight, sufficient ultraviolet curability may not be obtained.
  • alcohols such as water, methanol, ethanol, isopropanol, and butanol, tetrahydrofuran, ethyl ether
  • Organic solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, toluene, hexane, and chloroform
  • 0 to 55 parts by weight preferably 0 to 45 parts by weight can be added to 100 parts by weight of the total amount of the components (b) and (b).
  • composition of the present invention uses a cationic copolymer or the like having good solubility in a hydrophilic acryl-based monomer, there is almost no need to use a solvent. Therefore, there is an advantage that a drying step is almost unnecessary and the emission of organic substances is small.
  • the ultraviolet-curable resin composition of the present invention preferably contains a hydrophilic copolymer in addition to the above-mentioned essential components in order to improve the ink absorbency, as long as the purpose is not impaired.
  • the hydrophilic copolymer has a solubility in water of 1 g / 100 g or more, preferably 5 g / 100 g or more.
  • examples thereof include polyvinyl pyrrolidone, polyvinyl alcohol, and the like.
  • Examples include homopolymers of hydroxyxethyl cellulose, hydroxypropyl cellulose, polyacrylamide, polyethylene glycol, and the like, or copolymers containing such monomer components, and solubility in other components.
  • Polyvinyl viridone is preferred from the viewpoint of ink absorbency and the like.
  • a copolymer it may be a copolymer with a non-hydrophilic monomer.
  • hydrophilic polymer only one kind may be used, or two or more kinds may be used in combination.
  • the amount of the hydrophilic polymer used is 3 to 45 parts by weight when the total amount of the component (a) and the component (b) (hereinafter sometimes referred to as “resin equivalent component”) is 100 parts by weight. It is preferable to use parts. A more preferred amount is 5 to 40 parts by weight. If the amount of the hydrophilic polymer is more than 45 parts by weight, the water resistance of the ink tends to deteriorate, and the viscosity of the resin composition may increase. On the other hand, if the amount is less than 3 parts by weight, the wettability and the absorbability of the ink of the coating may deteriorate.
  • the resin composition of the present invention preferably contains an inorganic filler and / or an organic filler for the purpose of rapidly absorbing the ink and promoting drying.
  • inorganic fillers examples include silica, clay, silica, diatomaceous earth, calcium carbonate, calcium sulfate, barium sulfate, aluminum silicate, calcium silicate, synthetic zeolite, alumina, zinc oxide, and titanium oxide. And the like.
  • organic fillers include polymer particles such as polyacrylate, polymer acrylate, styrene resin, polyester resin, polycarbonate, modified melamine resin, polyvinyl alcohol, polyacrylamide, polyvinylpyrrolidone, and rubber. Examples thereof include crosslinked particles of these polymers, and powders of natural polymers such as lignin, protein, cellulose, and gelatin.
  • inorganic fillers and organic fillers may be used alone, or may be used in combination according to the purpose of improving the absorbency after writing, adjusting the viscosity of the ink, or improving the color tone.
  • the amount of these inorganic and / or organic fillers used is based on the resin equivalent
  • the viscosity of the composition becomes high and the strength of the obtained coating film decreases. On the other hand, if the added amount is less than 1 part by weight, sufficient ink absorbency cannot be imparted to the coating, and the viscosity of the composition may be too low.
  • composition of the present invention contains a monomer having at least two radically polymerizable double bonds in a molecule (hereinafter referred to as “multifunctional unit”) for the purpose of improving curability and increasing the strength of a film. ) Is preferably added.
  • polyfunctional monomers include, for example, trimethylolpropane acrylate, triacryl isocyanurate, 1,4-butanediol diacrylate, neopentylglycol diacrylate, dicyclopentenyl genyl acrylate, and pentaerythritol Toll tetraacrylate, glycerin diacrylate, pentaerythritol triacrylate, dipentyl erythritol hexyl acrylate, ethylene glycol diacrylate, from ring-opened polymers of anhydride and propylene oxide
  • the amount of the polyfunctional monomer to be used is preferably 0.1 to 20 parts by weight, more preferably 0.5 to 10 parts by weight, per 100 parts by weight of the resin equivalent component. You. If the amount exceeds 20 parts by weight, the ink absorbency of the resulting film will be poor. If the amount is less than 0.1 part by weight, the strength of the film may be slightly reduced.
  • the ultraviolet curable resin composition of the present invention further comprises, in addition to the above components, (Hereinafter collectively referred to as “copolymerizable monomers”).
  • copolymerizable monomers examples include, for example, butyl acrylate, pentyl acrylate, cyclohexyl acrylate, 2-ethylhexyl acrylate, and phenoloxy acrylate. Rate, isobornyl acrylate, dicyclopentenyl acrylate, dicyclopentenyl acrylate, dicyclopentenyloxyshethyl acrylate, and the like.
  • the amount of these copolymerizable monomers to be used is preferably 0.1 to 50 parts by weight per 100 parts by weight of the resin equivalent component, and more preferably 0.1 to 30 parts by weight. It is. If the amount is more than 50 parts by weight, the ink absorbency of the formed film will be poor, and if it is less than 0.1 part by weight, the strength of the film may be slightly weakened.
  • the composition of the present invention contains a polymerization inhibitor, a preservative, a sensitizer, a defoaming agent, a dispersant, a fungicide and the like within a range that does not impair the objects and effects of the present invention. Can be added.
  • the method for producing the composition of the present invention is not particularly limited, and any method can be used.
  • a hydrophilic acrylic monomer (b) a cationic copolymer, and (c) an essential component of a photopolymerization initiator, and (d) a solvent to be added as necessary.
  • a stirring tank for example, a stirring tank, a dissolver, a ball mill, a kneader, a sand mill, a three-roll mill, an ultrasonic disperser, and the like can be used.
  • the temperature at the time of mixing is preferably in the range of room temperature to 60 ° C. in order to prevent polymerization during mixing.
  • the method of applying this composition on a substrate includes a spin coating method, a spray coating method, a dive method, a gravure roll method, a knife coating method, a reverse roll method, a screen printing method, a bar coating method, and the like.
  • a method usually used for forming a film can be used without any particular limitation.
  • the obtained coating film is cured by irradiating ultraviolet rays to form a coating film.
  • the composition may be applied onto a substrate, dried to remove the solvent, formed into a coating film, and cured with ultraviolet light.
  • the irradiation intensity of ultraviolet light for curing is 1 0 0: may be L 0 0 0 m J / cm 2 approximately.
  • the thickness of the recording layer thus prepared is preferably from 1 to 100 m. More preferably, the thickness of the layer is from 5 to 40 m. If the thickness is too thick, the recording material is likely to warp or harden insufficiently. If the thickness is too thin, the ink permeability tends to decrease, and the ink absorbency after printing tends to deteriorate.
  • Such a recording material can be suitably used for an ink jet as described above. Further, since this recording material can be prepared without using a solvent, it is suitable as an ink receiving layer of an optical recording medium.
  • FIG. 1 shows an example of an optical recording medium having such a recording layer.
  • the optical recording medium 1 has a recording layer 13 mainly composed of a dye on a substrate 12, a metal reflective layer 14 in close contact with the recording layer 13, and a protective layer 15.
  • the recording surface layer 17 is formed on the protective layer 15.
  • the optical recording medium of the present invention A structure other than the structure shown in FIG. 1 may be adopted as long as the outer layer has an ink receiving layer formed by using the ultraviolet-curable resin composition of the present invention.
  • Example 1 A structure other than the structure shown in FIG. 1 may be adopted as long as the outer layer has an ink receiving layer formed by using the ultraviolet-curable resin composition of the present invention.
  • a 1000 ml flask equipped with a stirrer and a condenser was charged with 300 g of Solmix as a solvent and 2.1 g of AIBN as a polymerization initiator, and after purging with nitrogen for 30 minutes, the temperature was raised to 80 ° C. Then, a mixture of methyl chloride-modified dimethylaminoethyl methacrylate (80% aqueous solution) (12.5 g), dimethyl acrylamide (37.5 g), i-butyl methyl acrylate (22.5 g) and Solmix (51 g) was added to the dropping funnel. The mixture was dropped into the flask over 2 hours, and polymerization was carried out at 80 ° C. for 2 hours.
  • the molecular weight (Mw) of the cationic copolymer (3) was 2.8 ⁇ 10 4 .
  • methyl chloride-modified dimethylaminoethyl methacrylate (80% aqueous solution) 28.12 g, 4-hydroxybutyla 20 g of acrylate, 7.5 g of t-butyl methacrylate, 37.5 g of Solmix as a solvent, 37.5 g of water, 0.5 g of AIBN as a polymerization initiator, and nitrogen replacement for 30 minutes After that, the temperature was raised to 80 ° C, and polymerization was performed for 2 hours.
  • the molecular weight (Mw) of the cationic copolymer (4) was 1.2 ⁇ 10 5 .
  • the molecular weight (Mw) of the cationic copolymer (9) was 2.10 4 .
  • a predetermined amount of each component shown in Table 1 was blended, stirred and dispersed to prepare an ultraviolet-curable resin composition.
  • a recording material having a polyester film as a base material was prepared.
  • the abbreviations in the table indicate the following contents.
  • ACMO Acryloylmorpholine (Nippon Kayaku Co., Ltd.)
  • 4HBA 4-hydroxybutyl acrylate (Nippon Kasei Co., Ltd.)
  • Irgacure 819 Photopolymerization initiator (manufactured by Ciba Specialty Co., Ltd.)
  • Darocure 1 173 Photopolymerization initiator (Chivas Specialty Chemicals Co., Ltd.) 2
  • E HA 2-ethylhexyl acrylate
  • P VP Polyvinylpyrrolidone
  • ESLEC KX-l Polyvinylacetone (Sekisui Chemical Co., Ltd.)
  • ESLEC KW-1 Polyvinylacetal (Sekisui Chemical Co., Ltd.)
  • Poster 1002 Acryl-based crosslinkable filler (Nippon Shokubai Co., Ltd.) )
  • PAA-HC1 Polyallylamine hydrochloride (Nitto Boseki Co., Ltd.)
  • Fine Seal X-45 Silica (particle size: about 4 ⁇ m) (manufactured by Tokuyama Corp.)
  • Cationic monomer Ethyl acetate-modified dimethylaminoethyl acrylate type dye CR-95: titanium oxide (Ishihara Sangyo Co., Ltd.)
  • UX 2201 Urethane acrylate oligomer (manufactured by Nippon Kayaku Co., Ltd.)
  • the printed sample was placed in a constant temperature / humidity chamber at 30 ° C. and 90%, and the bleeding of characters was visually evaluated.
  • the nail was pressed against the UV cured film, and the surface was visually evaluated for scratches.
  • Component (c) parts by weight based on 100 parts by weight of (a)
  • composition of the present invention when applied to a base material and cured with ultraviolet light, a film having excellent printing characteristics, water resistance, and moisture resistance when used as a recording material for printing with an aqueous ink. Can be given. In addition, since no solvent is used, emission of organic substances can be reduced during coating and curing.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Ink Jet Recording Methods And Recording Media Thereof (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

L'invention concerne une matière d'impression présentant une excellente capacité d'impression à l'aide d'une encre à base d'eau, et peut présenter une résistance à l'eau et à l'humidité après impression; et une composition de résine pouvant être traitée par rayonnement ultraviolet, qui permet d'obtenir cette matière d'impression. La composition est caractérisée en ce qu'elle comporte les ingrédients (a) à (d) suivants: (a) monomère acrylique hydrophile; (b) copolymère cationique contenant de l'azote quaternaire; (c) initiateur de photopolymérisation; (d) solvant, et que la proportion de l'ingrédient (d) est de 0 à 55 parties en poids par 100 parties en poids correspondant à la somme des ingrédients (a) et (b).
PCT/JP2000/007898 1999-11-11 2000-11-09 Composition de resine pouvant etre traitee par rayonnement ultraviolet et matiere d'impression a jet d'encre comportant un film a base de cette composition WO2001034671A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU13041/01A AU1304101A (en) 1999-11-11 2000-11-09 Ultraviolet-curable resin composition and ink-jet recording material having filmbased on the composition

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP11/321125 1999-11-11
JP32112599 1999-11-11

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0673305A (ja) * 1991-03-26 1994-03-15 Mitsubishi Rayon Co Ltd 耐擦傷性及び帯電防止性に優れた合成樹脂成形品用被覆剤組成物
JPH10188345A (ja) * 1996-12-20 1998-07-21 Mitsui Chem Inc 光記録媒体
JP2001011343A (ja) * 1999-06-25 2001-01-16 Mitsubishi Chemicals Corp 紫外線硬化性樹脂組成物及び該組成物に基づく被膜を有するインクジェット用被記録材

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0673305A (ja) * 1991-03-26 1994-03-15 Mitsubishi Rayon Co Ltd 耐擦傷性及び帯電防止性に優れた合成樹脂成形品用被覆剤組成物
JPH10188345A (ja) * 1996-12-20 1998-07-21 Mitsui Chem Inc 光記録媒体
JP2001011343A (ja) * 1999-06-25 2001-01-16 Mitsubishi Chemicals Corp 紫外線硬化性樹脂組成物及び該組成物に基づく被膜を有するインクジェット用被記録材

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