JP3672651B2 - Ultraviolet curable resin composition for ink jet recording system and cured product thereof - Google Patents

Description

【００１４】
評価法
（貯蔵安定性）：各組成物をカートリッジ式のインク容器に密閉し、５０℃に加温し、１ケ月間放置し組成物の状態を観察した。
○・・・・全く変化していない。
△・・・・やや増粘がみられる。
×・・・・ゲル物が発生している。
（インクノズルの状態）：インクジエットプリンターで塗布試験中、インクノズルの状態を観察した。
○・・・・全く問題が無い。
△・・・・やや組成物の出が悪い。
×・・・・組成物が出なくなる。
（塗布性）：塗布された塗膜の状態を観察した。
○・・・・均一に塗布されている。
△・・・・やや膜厚にバラツキがある。
×・・・・塗布されない部分がある。
（硬化状態）：塗膜の硬化状態を観察した。
○・・・・問題なく硬化している。
×・・・・硬化の不良が発生している。
【００１５】
注）＊１ ＫＡＹＡＲＡＤ Ｒ−１１４：日本化薬（株）製、ビスフェノールＡ、ジグリシジルエーテルのアクリル酸エステル化物。
＊２ Ｉｒｇ １８４：チバ・ガイギー社製、光ラジカル重合開始剤
１−ヒドロキシシクロヘキシルフェニルケトン
＊３ オプトマーＳＰ−１７０：旭電化（株）製、光カチオン重合開始剤
【００１６】
表１の結果から明らかなように、本発明の樹脂組成物はインクジエットプリンターでの塗布適性に優れており、又、塗布や記録のための被記録媒体用樹脂層を必要としない。
【００１７】
【発明の効果】
本発明のインクジエット記録方式用紫外線硬化性樹脂組成物は、インクジエットプリンターでの塗布性能に優れ、塗布や記録のための被記録媒体用樹脂層を必要としない。スピンコーターでの塗布法のような再使用するための複雑な工程も必要がなく、光ディスク用材料に適する。[0001]
BACKGROUND OF THE INVENTION
The present invention relates to an ultraviolet curable resin composition for an ink jet recording system. More specifically, the present invention relates to an ultraviolet curable resin composition for an ink jet recording system and a cured product thereof particularly suitable for optical disk materials such as an optical disk overcoat agent or hard coat agent.
[0002]
[Prior art]
An ink jet recording method is used as one method for outputting an image such as a document or an image created by a personal computer to a recording medium such as paper or an OHP film. Usually, the recording medium in the ink jet recording system has a drawback that a resin layer for the recording medium must be formed on paper or a plastic film in order to improve the water resistance and light resistance of the image. Yes.
On the other hand, in the field of optical discs, an ultraviolet curable resin composition for protecting a recording film is used as an overcoat agent. As a coating method, a spin coat method is used and an amount larger than that used is used. In order to reuse an overcoat agent in an amount other than the required amount that must be placed on the recording film, the ink needs to be precisely filtered, which complicates the process.
[0003]
[Problems to be solved by the invention]
The present invention improves the above-described drawbacks, and can form an image or a coating film on a paper or plastic substrate without forming a resin layer for a recording medium, and can apply only a necessary amount. An ultraviolet curable resin composition for a jet recording system and a cured product thereof are provided.
[0004]
[Means for Solving the Problems]
The present invention relates to an ultraviolet curable resin composition for an ink jet recording system, comprising a (meth) acrylate compound (A), a vinyl ether compound (B), and a photopolymerization initiator (C), and a cured product thereof. .
[0005]
DETAILED DESCRIPTION OF THE INVENTION
Hereinafter, the present invention will be described in detail.
Specific examples of the (meth) acrylate compound (A) used in the present invention include, for example, hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, 1,4-butanediol mono (meth) acrylate, carbitol ( (Meth) acrylate, glycidyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, phenoxyethyl (meth) acrylate, phenyl polyethoxy (meth) acrylate, 1,6-hexanediol di (meth) acrylate, 1,9-nonane Diol di (meth) acrylate, polyethylene glycol di (meth) acrylate, 2-ethyl-2-butyl-1,3-butanediol di (meth) acrylate, hydroxypivalate neopentyl glycol di (meth) acrylate, Sphenol A polyethoxydi (meth) acrylate, bisphenol F polyethoxydi (meth) acrylate, trimethylolpropane tri (meth) acrylate, tricyclodecane dimethylol di (meth) acrylate, trimethylolpropane polyethoxytri (meth) acrylate, trimethylol Propane polypropoxytri (meth) acrylate, pentaerythritol tetra (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol polyethoxytetra (meth) acrylate, ditrimethylolpropane tetra (meth) acrylate, dipentaerythritol hexa And penta (meth) acrylate, dipentaerythritol polycaprolactone hexa (meth) acrylate, etc. Monomer, epoxy resin [for example, bisphenol A type epoxy resin (for example, Epicoat 828, Epicoat 1001 etc., manufactured by Yuka Shell Epoxy Co., Ltd.), bisphenol F type epoxy resin (for example, Yuka Shell Epoxy Corporation) Manufactured, Epicoat R-807, Epicoat 4001P, etc.), aliphatic epoxy resins (eg, glycerin polyglycidyl ether, trimethylolpropane triglycidyl ether, 1,6-hexanediol diglycidyl ether, etc.), phenol novolac type epoxy resins, etc. ] And (meth) acrylic acid are reaction products of epoxy (meth) acrylate and urethane (meth) acrylate [for example, ethylene glycol, propylene glycol, 1,4-butanediol, polypropylene glycol, polytetramethyl Polyols such as lenglycol, neopentyl glycol, polyester diol, polycaprolactone diol, polycarbonate diol and organic polyisocyanates such as tolylene diisocyanate, isophorone diisocyanate, hexamethylene diisocyanate and 2-hydroxyethyl (meth) acrylate, 2- And reactive oligomers such as hydroxyl-containing (meth) acrylates and reactants such as hydroxypropyl (meth) acrylate, 1,4-butanediol mono (meth) acrylate, pentaerythritol tri (meth) acrylate, and the like. .
[0006]
Specific examples of the vinyl ether compound (B) used in the present invention include 2-hydroxyethyl vinyl ether, 1,4-butanediol monovinyl ether, 1,9-nonanediol monovinyl ether, diethylene glycol monovinyl ether, triethylene glycol monovinyl ether, Cyclohexyl-1,4-dimethylol monovinyl ether, 2-chloroethyl vinyl ether, 2- (meth) acryloyloxyethyl vinyl ether, triethylene glycol vinyl ether, tetraethylene glycol divinyl ether, polytetramethylene glycol divinyl ether, 1,4-butane Diol divinyl ether, 1,9-nonanediol vinyl ether, cyclohexyl-1,4-dimethylol divinyl ether, trime Reactive vinyl ether monomers such as roll propane trivinyl ether and pentaerythritol tetravinyl ether, ethylene glycol, 1,4-butanediol, 3-methyl-1,5-pentanediol, polypropylene glycol, neopentyl glycol, polytetramethylene glycol Polyols such as polyester polyol and polycaprolactone polyol and tolylene diisocyanate, organic polyisocyanates such as 4,4'-diphenylmethane diisocyanate, isophorone diisocyanate, hexamethylene diisocyanate and hydroxyl group-containing vinyl ethers (for example, 2-hydroxyethyl vinyl ether, 1,4-butanediol monovinyl ether, cyclohexyl-1,4-dimethylol monovinyl ether Reactivity of urethane vinyl ether, which is a reaction product of the above), polyester polyvinyl ether, which is a reaction product of hydroxyl-containing vinyl ethers and polycarboxylic acid chlorides (for example, phthalic acid dichloride, isophthalic acid dichloride, tetrahydrophthalic acid dichloride, etc.) A vinyl ether oligomer etc. can be mentioned.
[0007]
Specific examples of the photopolymerization initiator (C) used in the present invention include 1-hydroxycyclohexyl phenyl ketone, 2,2-dimethoxy-2-phenylacetophenone, 2,2-diethoxy-2-phenylacetophenone, Benzyldimethyl ketal, 2,4-diethylthioxanthone, 2-chlorothioxanthone, isopropylthioxanthone, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholino-propane-1,4-benzoyl-4'-methyl Photoradical polymerization initiators such as diphenyl sulfide, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 2-ethylanthraquinone, etc.
Triphenylsulfonium hexafluoroantimonate, triphenylsulfonium hexafluorophosphate, SP-170, SP-150 (manufactured by Asahi Denka Co., Ltd.), FC-508, FC-512 (manufactured by 3M Company), UVE-1014 ( Polyarylsulfonium salts such as General Electric Company), metallocene compounds such as Irg-261 (manufactured by Ciba Geigy), diphenyliodonium hexafluoroantimonate, p-nonylphenylphenyliodonium hexafluoroantimonate, 4,4′- Examples include photocationic polymerization initiators such as polyaryliodonium salts such as diethoxyphenyliodonium hexafluoroantimonate. These photopolymerization initiators can be used alone or in combination of two or more.
[0009]
The resin composition of this invention can be prepared by melt | dissolving, mixing, kneading | mixing, etc. each component of (A), (B) and (C).
In the resin composition of the present invention, the proportion of each component used can be as follows (% is% by weight).
The component (A) is preferably 10 to 80% by weight, particularly preferably 20 to 75% by weight. The component (B) is preferably 10 to 85% by weight, particularly preferably 20 to 75% by weight. The component (C) is preferably 0.1 to 20% by weight, particularly preferably 0.5 to 15% by weight.
[0010]
The resin composition of the present invention may further include an epoxy resin (for example, a bisphenol A type epoxy resin, an aliphatic epoxy resin, an alicyclic epoxy resin, etc.), a colorant such as a dye or a pigment, an antifoaming agent, if necessary. Agents, leveling agents, polymerization inhibitors, waxes, antioxidants, non-reactive polymers, silane coupling agents, light stabilizers, antistatic agents, slip agents and the like can also be added.
As described above, the resin composition of the present invention is suitably used for optical disc materials such as an optical disc overcoat agent, hard coat agent or adhesive, but in addition, ink, paint, coating, adhesive, etc. Useful for.
[0011]
The resin composition of the present invention has an ink jet printer and has a thickness of 1 to 50 μm with a composition of various substrates (paper, plastic, plastic film, ceramic, glass, wood, etc.) or an optical disk substrate. Applied in range. After coating, the coating is cured by irradiating with ultraviolet rays.
[0012]
【Example】
Hereinafter, the present invention will be described more specifically with reference to examples. In addition, the part in an Example is a weight part.
Examples 1-4
The resin composition was prepared by heating and mixing in accordance with the formulation shown in Table 1. Each composition obtained was subjected to a coating test with an ink jet printer so as to have a thickness of 3 μm on the base of the optical disk, the storage stability of each composition in the ink container, and the state of the ink nozzles of the ink jet printer. The applicability was evaluated. Next, the applied coating film was irradiated with ultraviolet rays to obtain a cured coating film. The cured state was observed.
[0013]
[Table 1]

[0014]
Evaluation method (storage stability): Each composition was sealed in a cartridge-type ink container, heated to 50 ° C., allowed to stand for 1 month, and the state of the composition was observed.
○ ・ ・ ・ ・ No change at all.
Δ: Some thickening is observed.
X ··························································
(Ink nozzle state): During the application test with an ink jet printer, the state of the ink nozzle was observed.
○ ・ ・ ・ ・ No problem at all.
Δ: Slightly poor composition.
X ··· The composition is not produced.
(Applicability): The state of the applied coating film was observed.
○: Uniformly applied.
Δ: Some variation in film thickness.
× ··· There are parts that are not applied.
(Curing state): The cured state of the coating film was observed.
○ ···· Hardened without problems.
× ···· Hardening failure occurred.
[0015]
Note) * 1 KAYARAD R-114: Nippon Kayaku Co., Ltd., bisphenol A, diglycidyl ether acrylate ester.
* 2 Irg 184: Photo radical polymerization initiator 1-hydroxycyclohexyl phenyl ketone manufactured by Ciba Geigy Co., Ltd. * 3 Optomer SP-170: Photo cationic polymerization initiator manufactured by Asahi Denka Co., Ltd.
As is apparent from the results in Table 1, the resin composition of the present invention is excellent in application suitability with an ink jet printer, and does not require a recording medium resin layer for application or recording.
[0017]
【The invention's effect】
The ultraviolet curable resin composition for an ink jet recording system of the present invention is excellent in coating performance with an ink jet printer and does not require a resin layer for a recording medium for coating or recording. There is no need for a complicated process for reuse such as a coating method with a spin coater, and it is suitable for an optical disk material.

Claims (1)

In the ultraviolet curable resin composition for ink jet recording system, (meth) acrylate compound (excluding urethane (meth) acrylate) (A) is 10 to 80% by weight and vinyl ether compound (B) is 10 to 85% by weight. % And a photopolymerization initiator (C) in an amount of 0.1 to 20% by weight. An ultraviolet curable resin composition for an ink jet recording system for an optical disc .