JP2001011343A - UV curable resin composition and inkjet recording material having a coating based on the composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a recording material capable of imparting excellent printing characteristics and water resistance after printing when an aqueous ink is used, and ultraviolet light capable of providing such a recording material. Provide a curable resin composition. A composition comprising the following components (a) to (d), wherein the total amount of the three components (a), (b) and (c) is 100 parts by weight. Is an ultraviolet curable resin composition satisfying the following conditions. (A) hydrophilic acrylic monomer: 10 to 80 parts by weight (b) hydrophilic polymer: 3 to 50 parts by weight (c) quaternary ammonium base-containing acrylic monomer:
3 to 40 parts by weight (d) photopolymerizable initiator: 0.1 to 10 parts by weight

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to an ultraviolet-curable resin composition. In particular, the present invention relates to a film suitable for use in recording with an aqueous inkjet ink and an ultraviolet curable composition capable of forming a recording material having the same.

[0002]

2. Description of the Related Art Recording with an aqueous ink has been widely used in various fields because it has little effect on the environment and health. In particular, in recent years, the ink jet recording system has become widespread, and writing on various substrates has been studied. The ink used here usually includes a water-soluble dye,
The solvent contains water or a small amount of alcohol or the like. Therefore, if the printing surface is hydrophobic, the ink may be repelled without being absorbed, or the drying may be slow, causing problems such as transfer and contamination of the periphery. Therefore, in order to make the printing surface hydrophilic and improve ink receptivity, a coating made of a water-soluble polymer such as starch, gelatin, polyvinylpyrrolidone, polyvinyl alcohol, cellulose derivative, and sodium polyacrylate was formed on the substrate surface. Also, it has been proposed to mix inorganic or organic particles into the surface to make the surface porous. However, these methods have insufficient water resistance, such as print bleeding when water droplets adhere to the printing surface.

For the purpose of improving water resistance, there is a method for preventing re-elution of ink by forming an ion complex with a water-soluble dye, which often has an anionic group such as a sulfone group, and a cationic substance. Is being developed. Since the cationic substance used here is very hydrophilic, it is difficult to dissolve in water or a substance other than a highly hydrophilic solvent, and such a solvent is necessary to use the cationic substance in the composition. There was a problem that is.

Generally, in the process of producing a recording material for an aqueous ink, the above-mentioned water-soluble polymer, porous substance, cationic substance and the like are dissolved and mixed in a solvent to prepare a coating liquid. It is carried out in such a procedure that after coating on a substrate, drying and / or ultraviolet curing are carried out (JP-A-9-245379, JP-A-9-208609). In this case, since the coating liquid contains a solvent such as water, it was necessary to provide a drying step. On the other hand, the application of a receiving layer having an ultraviolet-curable ink jet recording material to an optical recording medium such as a CD-R has attracted attention.
No. 88, for example. When such a recording material is used for an optical recording medium, the coating liquid is required to be solvent-free in the process, but as described above, those containing a cationic substance include a solvent. Iris
JP-A-188345), and those without solvent do not contain a cationic substance.
No. 80), there is a practical problem that the water resistance of the ink is insufficient.

[0005]

SUMMARY OF THE INVENTION An object of the present invention is to provide a recording material capable of imparting excellent printing characteristics and water resistance after printing when an aqueous ink is used, and such a recording material. To provide an ultraviolet-curable resin composition capable of giving the following.

[0006]

Means for Solving the Problems The present inventors have conducted various studies to solve the above-mentioned problems, and as a result, have found that these problems can be solved by using a composition having a specific composition. Thus, the present invention has been completed. That is, the gist of the present invention is a composition containing the following components (a) to (d), wherein the total amount of the three components (a), (b) and (c) (hereinafter referred to as “resin equivalent component”) (Hereinafter referred to as "amount") as 100 parts by weight, the composition satisfies the following conditions. (A) hydrophilic acrylic monomer: 10 to 80 parts by weight (b) hydrophilic polymer: 3 to 50 parts by weight (c) quaternary ammonium base-containing acrylic monomer:
3 to 40 parts by weight (d) Photopolymerizable initiator: 0.1 to 10 parts by weight

[0007] The gist of the present invention is that the above-mentioned ultraviolet curable resin composition containing a volatile solvent in an amount of 10 parts by weight or less per 100 parts by weight of a resin equivalent component and an inorganic filler and / or an organic filler are equivalent to a resin. It is also present in the above-mentioned ultraviolet-curable resin composition containing 1 to 45 parts by weight per 100 parts by weight of the component. Another gist of the present invention is the above-mentioned ultraviolet curable resin composition, wherein the hydrophilic acrylic monomer as the component (a) has a structure represented by the following general formula (1) or (2). ,as well as

[0008]

Embedded image CH ₂ ＣＨCH—COO—R ¹ —OH (1)

(R ¹ : an alkylene group having 1 to 8 carbon atoms which may have a branched chain)

[0010]

Embedded image _{CH 2 = CH-COO-CH} 2 -CH (OH) -CH 2 O-R 2 (2)

(R ² : an alkyl group having 1 to 8 carbon atoms;
(Aryl group or aralkyl group) The ultraviolet curable resin composition according to the above, wherein the quaternary ammonium salt group-containing acrylic monomer of the component (c) has a structure represented by the general formula (3). ing.

[0012]

Embedded image CH ₂ ＣＨCH—COO—R ³ —N ⁺ (R ⁴ R ⁵ R ⁶ ) · X ⁻ (3)

(R ³ : alkylene group having 1 to 5 carbon atoms R ⁴ , R ⁵ : 1 carbon atom which may be the same or different
Alkyl groups having from 1 to 4 R ⁶ : alkyl groups having 1 to 10 carbon atoms, aryl groups, aralkyl groups, or groups represented by —CH ₂ COOR ⁷ (R ⁷ : alkyl groups having 1 to 4 carbon atoms) X ^- : Halogen ion or alkyl sulfate ion having 1 to 4 carbon atoms)

Another gist of the present invention is that a monomer or an oligomer having at least two radically polymerizable double bonds in a molecule is contained in an amount of 0.1 to 5 parts by weight per 100 parts by weight of a resin equivalent component.
The UV curable resin composition and the copolymerizable monomer contained in an amount of 0.1 parts by weight per 100 parts by weight of the resin-equivalent component amount.
The above-mentioned ultraviolet-curable resin composition containing 1 to 50 parts by weight. Another gist of the present invention is to provide an ink jet recording material having a cured layer of the above-mentioned ultraviolet curable resin composition on a substrate and an optical recording medium having the ink jet recording material as an ink receiving layer. Exist.

[0015]

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in detail. The hydrophilic acrylic monomer of 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. However, components corresponding to the component (c) described later are excluded. Examples of the hydrophilic group include a hydroxyl group, an acid amide group,
Examples include a morpholino group, an alkoxy group having 1 to 4 carbon atoms, a polyoxyethylene group having 1 to 60 carbon atoms, an amino group, a carboxyl group, a tetrahydrofurfuryl group, and a glycidyl group.

Specific examples of the hydrophilic acrylic monomer include hydroxyethyl acrylate, 1-hydroxypropyl acrylate, 2-hydroxypropyl acrylate, 2-hydroxybutyl acrylate, 4-hydroxybutyl acrylate, hydroxypentyl acrylate, and 2-hydroxypropyl acrylate. Hydroxy-3-phenoxypropyl acrylate, 2-hydroxy-3-butoxypropyl acrylate, 2-hydroxy-3-methoxypropyl acrylate, diethylene glycol monoacrylate, triethylene glycol monoacrylate, polyethylene glycol monoacrylate, dipropylene glycol monoacrylate, polypropylene Those having a hydroxyl group such as rylene glycol monoacrylate and glycerin monoacrylate, dimethyl Those having an acid amide group such as acrylamide or diethylacrylamide, or a highly polar monomer such as acryloylmorpholine, N-vinylpyrrolidone, 2-ethoxyethyl acrylate, 2-methoxyethyl acrylate, glycidyl acrylate, or tetrahydrofurfuryl acrylate Body.
These acrylic monomers may be used alone,
Two or more types may be used in combination. In particular, an acrylate having a structure represented by the following general formula (1) or (2) is preferable from the viewpoints of ink absorbency, solubility of other components, and the like.

[0017]

Embedded image CH ₂ ＣＨCH—COO—R ¹ —OH (1)

(R ¹ : alkylene group having 1 to 8 carbon atoms which may have a branched chain)

[0019]

Embedded image _{CH 2 = CH-COO-CH} 2 -CH (OH) -CH 2 O-R 2 (2)

(R ² : an alkyl group having 1 to 8 carbon atoms,
(Aryl group or aralkyl group) The amount of the (a) hydrophilic acrylic monomer to be used is 10 to 80 when the amount of the resin equivalent component is 100 parts by weight.
Use parts by weight. A more preferred amount is 20 to 70 parts by weight. (A) When the amount of the hydrophilic acrylic monomer exceeds 80 parts by weight, the resulting coating film has too high a hydrophilicity, resulting in inferior water resistance. Viscosity increases and handleability deteriorates.

The hydrophilic polymer of the component (b) used in the present invention refers to a polymer having a solubility in water of 1 g / 100 g or more, preferably 5 g / 100 g or more. Examples thereof include polyvinylpyrrolidone, polyvinyl alcohol and hydroxy alcohol. Examples include homopolymers of ethyl cellulose, hydroxypropyl cellulose, polyacrylamide, polyethylene glycol, and the like, and copolymers containing such monomer components. Among them, polyvinylpyrrolidone, polyethylene glycol, and hydroxypropylcellulose are preferred from the viewpoint of solubility in water and hydrophilic acrylic monomers. Particularly preferred is polyvinylpyrrolidone. In the case of a copolymer, it may be a copolymer with a non-hydrophilic monomer.

As the hydrophilic polymer (b), only one kind may be used, or two or more kinds may be used in combination. As the hydrophilic polymer, those which are soluble in the hydrophilic acrylic monomer (a) are preferably used. However, when the polymer is hardly soluble or insoluble, a small amount of water, methanol, ethanol, propanol, butanol or the like is used. May be dissolved in a solvent such as alcohols, ethers such as dimethyl ether, diethyl ether, methyl ethyl ether and dipropyl ether, and ketones such as acetone and methyl ethyl ketone.

(B) The hydrophilic polymer is used in an amount of 3 to 50 parts by weight based on 100 parts by weight of the resin equivalent component. A more preferable content in the composition is 5 to 40 parts by weight. If the amount of the hydrophilic polymer exceeds 50 parts by weight, the water resistance of the ink tends to deteriorate, and the viscosity of the resin composition increases. On the other hand, if the amount is less than 3 parts by weight, the wettability and absorbability of the ink of the coating film will be poor. The acrylic monomer containing a quaternary ammonium base as the component (c) is an acrylic monomer having a quaternary ammonium base in the molecule, and forms an ion complex with the anionic dye in the ink, and exhibits water resistance. Improve. This fourth
As the quaternary ammonium salt group-containing acrylic monomer, those having a structure represented by the following general formula (3) are preferable.

[0024]

Embedded image CH ₂ ＣＨCH—COO—R ³ —N ⁺ (R ⁴ R ⁵ R ⁶ ) · X ⁻ (3)

(R ³ : alkylene group having 1 to 5 carbon atoms R ⁴ , R ⁵ : 1 carbon atom which may be the same or different
Alkyl groups having from 1 to 4 R ⁶ : alkyl groups having 1 to 10 carbon atoms, aryl groups, aralkyl groups, or groups represented by —CH ₂ COOR ⁷ (R ⁷ : alkyl groups having 1 to 4 carbon atoms) X ^- : Halogen ion or alkyl sulfate ion having 1 to 4 carbon atoms)

The quaternary ammonium salt group-containing acrylic monomer may be used alone or in combination of two or more. The amount of the (c) quaternary ammonium base-containing acrylic monomer used is 3 to 40 parts by weight per 100 parts by weight of the resin equivalent component. A more preferred amount is 5 to 30 parts by weight. If the content of the quaternary ammonium base-containing acrylic monomer exceeds 40 parts by weight, the surface of the formed film tends to become sticky, while if it is 3 parts by weight or less, the water resistance of the ink deteriorates.

As the photopolymerization initiator of the component (d), a compound capable of generating a free radical (radical) by being dissociated by an active energy ray such as light or ultraviolet light is used.
Specific examples thereof include 2,2-diethoxyacetophenone, benzyldimethyl ketal, 2-hydroxy-2-
Methylpropiophenone, acetophenones such as 1-hydroxycyclohexylgenyl ketone, benzophenone, Michler's ketone, benzophenones such as o-benzoyl-methylbenzoate, benzoin alkyl ethers such as isopropylbenzoin ether,
Thioxanthones such as 2-chlorothioxanthone,
Bisacylphosphine oxides such as bis (2,4,6-trimethylbenzoyl) phenylphosphine oxide and bis (2,6-dimethoxybenzoyl) -2,4,4-trimethylpentylphosphine oxide are exemplified. These photopolymerization initiators can be used alone or 2
More than one type may be used in combination. Further, a sensitizer may be added. The amount of the photopolymerization initiator to be used is 0.1 to 10 parts by weight, more preferably 0.5 to 5 parts by weight, per 100 parts by weight of the resin equivalent component. When the use amount of the photopolymerization initiator exceeds 5 parts by weight, the strength of the obtained coating film decreases, while when it is less than 0.1 part by weight, sufficient ultraviolet curability cannot be obtained.

The ultraviolet-curable resin composition of the present invention contains, in addition to the above essential components, a filler (filler) such as an inorganic filler or an organic filler for the purpose of rapidly absorbing the ink and promoting drying. Is preferably contained. Examples of the inorganic filler that can be used include silica, clay, talc, diatomaceous earth, calcium carbonate, calcium sulfate, barium sulfate, aluminum silicate, synthetic zeolite, alumina, zinc oxide, and titanium oxide. As the organic filler, polyacrylate, polymethacrylate, styrene resin, polyester resin, polycarbonate, modified melamine resin, polyvinyl alcohol, polyacrylamide,
Examples thereof include polymer particles such as polyvinylpyrrolidone and rubber, particles of a crosslinked product of these polymers, and powders of natural polymers such as lignin, protein, and cellulose.

These inorganic fillers and organic fillers may be used alone or in combination depending on the purpose of improving the drying property after writing, adjusting the viscosity of the ink, or improving the color tone. These inorganic fillers and / or organic fillers are used in an amount of 1 to 40 per 100 parts by weight of the resin equivalent component.
It is preferable to use parts by weight.
-30 parts by weight. The amount of these fillers used is 40
If the amount is more than 10 parts by weight, the viscosity of the composition becomes high, and the strength of the obtained film decreases. On the other hand, if the added amount is less than 1 part by weight, sufficient ink drying property cannot be imparted to the coating, and the viscosity of the composition may be too low.

The composition of the present invention contains a monomer or oligomer having at least two radically polymerizable double bonds in the molecule (hereinafter referred to as a monomer or an oligomer) for the purpose of improving curability and increasing the strength of the coating. It is preferable to collectively add "polyfunctional monomers"). Examples of such polyfunctional monomers include, for example, trimethylolpropane triacrylate, triacryl isocyanurate, 1,4-butanediol diacrylate, neopentyl glycol diacrylate, dicyclopentadienyl diacrylate, and pentaerythritol Tetraacrylate, glycerin diacrylate, pentaerythritol triacrylate, dipentaerythritol hexaacrylate, ethylene glycol diacrylate, or an ester of acrylic acid with a polyester diol composed of a ring-opening polymer of phthalic anhydride and propylene oxide, and adipic acid , 6
Esters of acrylic acid with polyester diol composed of hexanediol, esters of acrylic acid with triol composed of a reaction product of trimellitic acid and diethylene glycol, hexamethylene diisocyanate and 1,6
-Hydroxydiol and a reaction product of polyurethane and 2-hydroxyethyl acrylate or adipic acid and a diisocyanate oligomer obtained by reacting a polyester diol of 1,6-hexanediol and tolylene diisocyanate to form 2-hydroxyethyl acrylate And oligomers having two or more radically polymerizable groups in the molecule, such as urethane-based oligomers that have been reacted with, and ether-based oligomers composed of esters of polypropylene glycol and acrylic acid. The amount of these polyfunctional monomers to be used is preferably 0.1 to 5 parts by weight, more preferably 0.5 to 3 parts by weight, per 100 parts by weight of the resin equivalent component. If the amount exceeds 5 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.

Further, in order to improve and adjust various physical properties such as hardness, adhesion, water resistance and moisture resistance of the obtained film, the ultraviolet curable resin composition of the present invention further comprises A monomer copolymerizable with the monomer in this component (hereinafter referred to as “copolymerizable monomer”) may be contained. Examples of the copolymerizable monomer that can be used as described above include, for example, butyl acrylate, pentyl acrylate, cyclohexyl acrylate, 2-ethylhexyl acrylate, phenoxyethyl acrylate, isobornyl acrylate, dicyclopentanyl acrylate, and dicyclopentenyl. Acrylate and dicyclopentenyloxyethyl acrylate. The amount of these copolymerizable monomers to be used is preferably 0.1 to 50 parts by weight, more preferably 0.1 to 30 parts by weight, per 100 parts by weight of the resin equivalent component. If the amount exceeds 50 parts by weight, the ink drying property 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.

In addition to the components other than the above, a polymerization inhibitor, a preservative, an antifoaming agent, a fungicide, and the like may be added to the composition of the present invention as long as the objects and effects of the present invention are not impaired. it can. The method for producing the composition of the present invention is not particularly limited, and any method can be used. For example, (a) a hydrophilic acrylic monomer, (b) a hydrophilic polymer,
(C) a quaternary ammonium base-containing acrylic monomer,
And (d) a method of weighing a predetermined amount of an essential component and other optional components of the photopolymerizable initiator, mixing and dissolving, adding an organic filler and / or an inorganic filler, and stirring and mixing. And a method of stirring and mixing the components at once. As a device for stirring and mixing, for example, a stirring tank, a dissolver, a ball mill, a kneader, a sand mill, a three-roll, an ultrasonic disperser, and the like can be used.
The temperature during mixing is from room temperature to prevent polymerization during mixing.
The temperature is preferably in the range of 60 ° C.

By coating the composition of the present invention on a base material such as paper, glass, plastic, ceramic and metal and curing it with ultraviolet rays, a high-performance ink jet recording material can be obtained. As a method of applying this composition on a substrate, there are spin coating, spray coating, dipping, gravure roll, knife coating, reverse roll, screen printing, bar coating, etc. Can be used without any particular limitation. The obtained coating film is cured by irradiating ultraviolet rays to form a coating film. When a solvent is contained in the composition, the composition may be applied onto a substrate, dried to remove the solvent, formed into a coating film, and cured with ultraviolet light. UV irradiation intensity for curing is 10
It may be about 0 to 1000 mJ / cm ² .

The thickness of the recording layer thus prepared is preferably 1 to 100 μm. A more preferred layer thickness is 5 to 40 μm. If the thickness is too large, the recording material is likely to be warped or hardened insufficiently. If the thickness is too small, the ink permeability tends to decrease, and the ink drying property after printing tends to deteriorate. Such a recording material can be suitably used for inkjet as described above. Further, since this recording material can be prepared using almost no 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. FIG.
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 16 is formed thereon. The optical recording medium of the present invention has a structure other than the structure shown in FIG. 1 as long as it has an ink receiving layer formed using the ultraviolet curable resin composition of the present invention as the outermost layer. You may.

[0035]

EXAMPLES Hereinafter, the present invention will be described more specifically with reference to examples, but the present invention is not limited to the following examples unless it exceeds the gist of the present invention. <Production Example 1> Synthesis of hydrophilic acrylic monomer (2-hydroxy-3-butoxypropyl acrylate) In a 300 ml flask equipped with a stirrer and a condenser, 78 g of butyl glycidyl ether, 1.05 g of dimethylbenzylamine as a catalyst, 0.162 g of methoxyphenol was charged as a polymerization inhibitor, and 8
The temperature was raised to 5 ° C. Thereafter, 56.2 g of acrylic acid was added dropwise, and the reaction was performed for 8 hours. The resulting reaction product was purified to obtain 94 g of 2-hydroxy-3-butoxypropyl acrylate.

<Production Example 2> Synthesis of acrylic monomer containing quaternary ammonium base (1) In a 300 ml flask equipped with a stirrer and a condenser, 85.9 g of dimethylaminoethyl acrylate and methoxyphenol as a polymerization inhibitor were added. 0.266 g was charged, and the temperature was raised to 60 ° C. while blowing air. Thereafter, 73.5 g of ethyl chloroacetate was added dropwise and reacted for 1 hour.
The reaction was continued for 2 hours while adding 106.2 g of -hydroxybutyl acrylate dropwise to obtain a quaternary ammonium salt group-containing acrylic monomer. <Production Example 3> Synthesis of quaternary ammonium base-containing acrylic monomer (2) In a 300 ml flask equipped with a stirrer and a cooling tube, 42.96 g of dimethylaminoethyl acrylate, and 0.08 g of methoxyphenol as a polymerization inhibitor. The temperature was raised to 60 ° C. while charging and blowing air. Thereafter, 46.25 g of diethyl sulfuric acid was added dropwise and reacted for 2 hours to obtain a quaternary ammonium salt group-containing acrylic monomer.

<Examples 1 to 9 and Comparative Examples 1 to 4> The components shown in the table were mixed in predetermined amounts and dispersed by stirring to prepare an ultraviolet curable resin composition. This composition is applied on a 50 μm-thick polyester film using a # 10 bar coater, and then irradiated with 330 mJ / cm ² of ultraviolet light to form a coating based on a polyester film having a 15 μm-thick coating. A recording material was produced. (However, in Example 1, after coating with a bar coater, the coating was dried at 70 ° C. for 3 minutes, and then subjected to an ultraviolet curing treatment.)

The abbreviations in the table indicate the following compounds, polymers or chemicals. MA: acryloylmorpholine M600A: 2-hydroxy-3-phenoxypropyl acrylate DMAA: dimethylacrylamide PEG: polyethylene glycol (molecular weight: about 20,000) PVP: polyvinylpyrrolidone (K30) DMC: dimethylaminoethyl methacrylate methyl chloride modified product Saftomer ST3300: 4th Methacrylic polymer containing quaternary ammonium base (Mitsubishi Chemical Corporation) PR202: Urethane acrylate oligomer (Mitsubishi Chemical Corporation) Irgacure 819: Photopolymerization initiator (Ciba Specialty Chemicals Corporation) 70PA: Hydroxy group-containing diacrylate Monomer (Kyoeisha Chemical Co., Ltd.) 3EGA: Triethylene glycol diacrylate (Kyoeisha Chemical Co., Ltd.) FA513: Dicyclopentanyl acrylate (Hitachi Chemical Co., Ltd.) 2EHA: 2-ethylhexyl acrylate Epostar 1002: acrylic resin crosslinkable filler (manufactured by Nippon Shokubai Co., Ltd.) Finesil X-37: silica powder (particle size of about 2 [mu] m)
(Manufactured by Tokuyama Corporation) Titanium oxide: Taipaque CR-95 (Ishihara Sangyo Co., Ltd.)
Made)

<Evaluation Method> An ink jet printer (Canon: Canon) was applied to the recording materials obtained in the above Examples and Comparative Examples.
Using BJC430J-Lite), solid printing of each color of black, blue, red, and yellow was performed.
The evaluation was performed according to the following method. (1) Ink bleeding The ink bleeding in the printed portion was visually evaluated. ：: No ink bleeding observed X: Ink bleeding observed (2) Ink absorbency Two minutes after printing was completed, plain paper was brought into contact with the printed portion, and the ink transfer was visually evaluated. . ：: Almost no transfer was observed. ：: Slight transfer was observed. X: Clear transfer was observed. (3) Water resistance of ink One day after printing, water was dropped on the printed part, and after 30 seconds, the water was wiped off. The state of remaining ink was visually evaluated. ◎: Almost no change ○: Slight decolorization ×: Remarkable decolorization

<Evaluation of Results> (1) As shown in the table, the recording material having a coating based on the composition of the present invention showed good results in all of the above evaluation items. (2) In Comparative Example 1 in which a methacrylic monomer was used in place of the quaternary ammonium group-containing acrylic monomer as the component (c), the ink bleeding was poor, and dimethylacrylamide not corresponding to the component (c) was used. In Comparative Example 2 using, all of the ink bleeding, absorption, and water resistance were inferior. (3) Instead of the hydrophilic acrylic monomer of the component (a),
Comparative Example 3 using hydroxyethyl methacrylate, which is hydrophilic but is a methacrylic monomer, is inferior in all of ink bleeding, absorbency, and water resistance. (4) The hydrophilic polymer of the component (b) and the fourth polymer of the component (c)
In Comparative Example 4 in which a polymer containing a quaternary ammonium base was used instead of both of the acrylic monomers containing a quaternary ammonium group, this polymer was dissolved in the hydrophilic acrylic monomer of the component (a). No uniform composition was obtained.

[0041]

[Table 1]

[0042]

[Table 2]

[0043]

As described above, when the composition of the present invention is applied to a base material and cured with ultraviolet light, a film having excellent printing characteristics and water resistance can be obtained when used as a recording material for printing with an aqueous ink. Can be given. Further, since almost no solvent is used, the effect on the environment and health during coating and curing is small.

[Brief description of the drawings]

FIG. 1 shows an example of an optical recording medium having a recording layer based on the ultraviolet-curable resin composition of the present invention.

[Explanation of symbols]

 DESCRIPTION OF SYMBOLS 1 Optical recording medium 12 Substrate 13 Recording layer containing a pigment as a main component 14 Metal reflection layer provided in close contact with the recording layer 15 Protective layer 16 Recording surface layer formed on the protective layer

 ──────────────────────────────────────────────────の Continuing on the front page (72) Inventor Yasuo Kitani 1 Tohocho, Yokkaichi-shi, Mie Mitsubishi Chemical Corporation Yokkaichi Office (72) Inventor Fujio Matsuishi 1000 Kamoshida-cho, Aoba-ku, Yokohama-shi, Kanagawa Prefecture Mitsubishi Chemical Corporation F-term in Yokohama Research Institute (reference) EL066 EN137 EP016 EU026 EU236 EV308 EW148 FA083 FD013 FD019 FD140 FD158 GP03 GS00 4J011 AA05 PA07 PA09 PA13 PA53 PA54 PA55 PA59 PA64 PA65 PA69 PA74 PA85 PA88 PA89 PA90 PB19 PB22 QA03 QA06 QA07 QA07 QA07 QA08 QA34 SA64 SA84 TA06 TA09 TA10 UA01 VA01 WA10 4 J038 BA042 CE022 CG172 CK032 DF022 FA151 FA152 FA162 KA04 KA08 PA17 PB11

Claims (9)

[Claims] 1. A composition comprising the following components (a) to (d), wherein the total amount of the three components (a), (b) and (c) (hereinafter referred to as “resin equivalent component amount” Wherein the composition satisfies the following conditions when (a) is 100 parts by weight: (A) hydrophilic acrylic monomer: 10 to 80 parts by weight (b) hydrophilic polymer: 3 to 50 parts by weight (c) quaternary ammonium base-containing acrylic monomer:
3 to 40 parts by weight (d) Photopolymerizable initiator: 0.1 to 10 parts by weight 2. The ultraviolet curable resin composition according to claim 1, wherein the volatile solvent contains 10 parts by weight or less per 100 parts by weight of the resin equivalent component. 3. The ultraviolet curable resin composition according to claim 1, wherein the composition contains 1 to 45 parts by weight of an inorganic filler and / or an organic filler per 100 parts by weight of a resin equivalent component. 4. The method according to claim 1, wherein the hydrophilic acrylic monomer as the component (a) has a structure represented by the following general formula (1) or (2). The ultraviolet-curable resin composition according to the above. CH ₂ ＣＨCH—COO—R ¹ —OH (1) (R ¹ : an alkylene group having 1 to 8 carbon atoms which may have a branched chain) CH ₂ ＣＨCH— COO—CH ₂ —CH (OH) —CH ₂ O—R ² (2) (R ² : an alkyl group, an aryl group or an aralkyl group having 1 to 8 carbon atoms) 5. The ultraviolet ray according to claim 1, wherein the quaternary ammonium salt group-containing acrylic monomer of the component (c) has a structure represented by the general formula (3). Curable resin composition. Embedded image CH ₂ ＣＨCH—COO—R ³ —N ⁺ (R ⁴ R ⁵ R ⁶ ) · X ⁻ (3) (R ³ : alkylene group having 1 to 5 carbon atoms R ⁴ , R ⁵ : same) But may be different 1 carbon atom
Alkyl groups having from 1 to 4 R ⁶ : alkyl groups having 1 to 10 carbon atoms, aryl groups, aralkyl groups, or groups represented by —CH ₂ COOR ⁷ (R ⁷ : alkyl groups having 1 to 4 carbon atoms) X ^- : Halogen ion or alkyl sulfate ion having 1 to 4 carbon atoms) 6. The method according to claim 1, wherein the monomer or oligomer having at least two radical polymerizable double bonds in the molecule is contained in an amount of 0.1 to 5 parts by weight per 100 parts by weight of the resin equivalent component. Item 2. The ultraviolet-curable resin composition according to item 1. 7. A copolymerizable monomer having a resin equivalent component amount of 100
The amount is 0.1 to 50 parts by weight per part by weight.
The ultraviolet-curable resin composition according to any one of the above. 8. A recording material for ink jet, comprising a cured layer of the ultraviolet-curable resin composition according to claim 1 on a substrate. 9. An optical recording medium having the ink jet recording material according to claim 8 as an ink receiving layer.