JP2016199727A - ポリエステル樹脂、平版印刷インキおよび印刷物 - Google Patents
ポリエステル樹脂、平版印刷インキおよび印刷物 Download PDFInfo
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- JP2016199727A JP2016199727A JP2015082777A JP2015082777A JP2016199727A JP 2016199727 A JP2016199727 A JP 2016199727A JP 2015082777 A JP2015082777 A JP 2015082777A JP 2015082777 A JP2015082777 A JP 2015082777A JP 2016199727 A JP2016199727 A JP 2016199727A
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- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
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- 238000004040 coloring Methods 0.000 description 1
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- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
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- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 1
- WPUMVKJOWWJPRK-UHFFFAOYSA-N naphthalene-2,7-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=CC2=CC(C(=O)O)=CC=C21 WPUMVKJOWWJPRK-UHFFFAOYSA-N 0.000 description 1
- OBJNZHVOCNPSCS-UHFFFAOYSA-N naphtho[2,3-f]quinazoline Chemical compound C1=NC=C2C3=CC4=CC=CC=C4C=C3C=CC2=N1 OBJNZHVOCNPSCS-UHFFFAOYSA-N 0.000 description 1
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- 239000001294 propane Substances 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Polymerisation Methods In General (AREA)
- Graft Or Block Polymers (AREA)
- Polyesters Or Polycarbonates (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Abstract
【解決手段】ポリエステル樹脂(A)、顔料、アクリレートオリゴマー、アクリレートモノマー、および、光開始剤を含有することを特徴とする活性エネルギー線硬化型平版印刷インキであって、
ポリエステル樹脂(A)が、ロジン類(a)5〜25重量%、カルボキシル基を2つ以上有する化合物(b)15〜50重量%、イソソルビド(c)10〜45重量%、ポリオール(d)(ただし、イソソルビド(c)を除く)15〜45重量%を反応させたものである、活性エネルギー線硬化型平版印刷インキ。
【選択図】なし
Description
ロジン類(a)5〜25重量%と、
カルボキシル基を2つ以上有する化合物(b)15〜50重量%と、
イソソルビド(c)10〜45重量%と、
ポリオール(d)15〜45重量%とを
反応させてなる上記ポリエステル樹脂(A)に関する。
本発明において有用なジカルボン酸の例としては以下のものが挙げられるが、これらに限定するものではない。テレフタル酸、イソフタル酸、1,4−ナフタレンジカルボン酸、2,6−ナフタレンジカルボン酸、2,7−ナフタレンジカルボン酸、1,4−シクロヘキサンジカルボン酸、シクロヘキサン二酢酸、5−ソジオスルホイソフタル酸、アジピン酸、アゼライン酸、グルタル酸、マレイン酸、マロン酸、ジメチルマロン酸、アリルマロン酸、シュウ酸、セバシン酸、コハク酸、スルホイソフタル酸、2,5−フランジカルボン酸、2,5−チオフェンジカルボン酸、3,4’−及び4,4’−ジフェニルスルフィドジカルボン酸、ジフェニル−4,4’−ジカルボン酸、ナフタレンジカルボキシレート、3,4’−及び4,4’−ジフェニルスルホンジカルボン酸、3,4’−及び4,4’−ベンゾフェノンジカルボン酸、4,4’−メチレンビス(シクロヘキシル)ジカルボン酸、トランス−1,4−シクロヘキサンジカルボン酸、シス−1,4−シクロヘキサンジカルボン酸、シス−及び/又はトランス−1,3−シクロヘキサンジカルボン酸、4−シクロヘキサン−1,2−ジカルボン酸、2−エチルスベリン酸、1,2−ビス(4−カルボキシフェノキシ)エタン、4,4’−メチレン−ビス(安息香酸)、4,4’−メチレン−ビス(シクロヘキシル)カルボン酸、3,4−フランジカルボン酸、1,1−シクロブタンジカルボン酸、p−カルボキシフェニル/オキシ安息香酸、エチレン(p−オキシ安息香酸)、トランス−4,4’−スチルベンジカルボン酸、2,2,3,3−テトラメチルコハク酸、シクロペンタンジカルボン酸、デカヒドロ−1,5−ナフチレンジカルボン酸、デカヒドロ−2,6−ナフチレンジカルボン酸、4,4’−ビシクロヘキシルジカルボン酸、フマル酸、ダイマー酸、レゾルシノール二酢酸、並びに4,4’−二安息香酸などであり、これらは単独で又は組合せて使用する。
カルボキシル基を2つ以上有する化合物(b)15〜50重量%と、
イソソルビド(c)10〜45重量%と、
ポリオール(d)15〜45重量%とを、あわせて100重量%をエステル化させることが好ましい。
なかでも、平版印刷インキ用バインダー、特に、活性エネルギー線硬化型平版印刷インキ用バインダーとして有用である。
およびそれらの混合物が挙げられる。
無機顔料としては黄鉛、亜鉛黄、紺青、硫酸バリウム、カドミムレッド、酸化チタン、亜鉛華、弁柄、アルミナホワイト、炭酸カルシウム、群青、カーボンブラック、グラファイト、アルミニウム粉等が挙げられ、
有機顔料としては、β−ナフトール系、β−オキシナフトエ酸系、β−オキシナフトエ酸系アリリド系、アセト酢酸アリリド系、ピラゾロン系等の溶性アゾ顔料、β−ナフトール系、β−オキシナフトエ酸系アリリド系、アセト酢酸アリリド系モノアゾ、アセト酢酸アリリド系ジスアゾ、ピラゾロン系等の不溶性アゾ顔料、銅フタロシアニンブルー、ハロゲン化(塩素または臭素化)銅フタロシアニンブルー、スルホン化銅フタロシアニンブルー、金属フリーフタロシアニン等のフタロシアニン系顔料、キナクリドン系、ジオキサジン系、スレン系(ピラントロン、アントアントロン、インダントロン、アントラピリミジン、フラバントロン、チオインジゴ系、アントラキノン系、ペリノン系、ペリレン系等)、イソインドリノン系、金属錯体系、キノフタロン系等の多環式顔料および複素環式顔料等の公知公用の各種顔料が使用可能である。
ポリエステル樹脂(A) 10〜40重量%
アクリレートモノマー 30〜75重量%
顔料(有機顔料・無機顔料) 5〜40重量%
光開始剤 0.01〜15重量%
その他の成分 1〜15重量%
が挙げられる。
〔実施例1〕
攪拌機、水分離器付き還流冷却器、温度計付4つ口フラスコに、ガムロジン25部、テレフタル酸15部、イソソルビド45部、ネオペンチルグリコール15部、キシレン60部を仕込み、窒素ガスを吹き込みながら、230℃まで加熱した。
その後、p−トルエンスルホン酸一水和物0.1部を添加し、230℃で15時間脱水縮合し、酸価31、GPC測定ポリスチレン換算重量平均分子量(Mw)1.8万の樹脂(R1)を得た。
次いで、同様のフラスコに樹脂(R1)を34部、ジペンタエリスリトールヘキサアクリレート65.9部、ハイドロキノン0.1部を混合し、110℃で加熱溶融しワニス(V1)を得た。
さらに、リオノールブルーFG7330(トーヨーカラー社製藍顔料)20部、ワニス(V1)を63部、トリメチロールプロパンテトラアクリレート11.9部、4,4’−ビス(ジエチルアミノ)ベンゾフェノン2.5部、2−メチル−2−モノホリノ(4−チオメチルフェニル)プロパン−1−オン2.5部、ハイドロキノン0.1部を、40℃の三本ロールミルにて練肉し、インキのタックが9〜10になるようにトリメチロールプロパンテトラアクリレートで調整し、平版印刷インキ(C1)を得た。
インキのタックは東洋精機社製インコメーターにてロール温度30℃、400rpm、1分後の値を測定した。
実施例1と同様の操作にて、表1に示す配合組成で酸価29、Mw2.7万の樹脂(R2)を得た。次いで、表2に示す配合組成でワニス(V2)、表3に示す配合組成にて平版印刷インキ(C2)を得た。
実施例1と同様の操作にて、表1に示す配合組成で酸価26、Mw2.1万の樹脂(R3)を得た。次いで、表2に示す配合組成でワニス(V3)、表3に示す配合組成にて平版印刷インキ(C3)を得た。
実施例1と同様の操作にて、表1に示す配合組成で酸価36、Mw2.0万の樹脂(R4)を得た。次いで、表2に示す配合組成でワニス(V4)、表3に示す配合組成にて平版印刷インキ(C4)を得た。
実施例1と同様の操作にて、表1に示す配合組成で酸価17、Mw2.4万の樹脂(R5)を得た。次いで、表2に示す配合組成でワニス(V5)、表3に示す配合組成にて平版印刷インキ(C5)を得た。
実施例1と同様の操作にて、表1に示す配合組成で酸価20、Mw2.3万の樹脂(R6)を得た。次いで、表2に示す配合組成でワニス(V6)、表3に示す配合組成にて平版印刷インキ(C6)を得た。
実施例1と同様の操作にて、表1に示す配合組成で酸価31、Mw3.0万の樹脂(R7)を得た。次いで、表2に示す配合組成でワニス(V7)、表3に示す配合組成にて平版印刷インキ(C7)を得た。
実施例1と同様の操作にて、表1に示す配合組成で酸価12、Mw1.5万の樹脂(R8)を得た。次いで、表2に示す配合組成でワニス(V8)、表3に示す配合組成にて平版印刷インキ(C8)を得た。
攪拌機、水分離器付き還流冷却器、温度計付4つ口フラスコに、ガムロジン15部、テレフタル酸35部、ネオペンチルグリコール30部、ペンタエリスリトール20部、キシレン60部を仕込み、窒素ガスを吹き込みながら、230℃まで加熱した。
その後、p−トルエンスルホン酸一水和物0.1部を添加し、230℃で15時間脱水縮合し、酸価32、GPC測定ポリスチレン換算重量平均分子量(Mw)2.7万の樹脂(RA)を得た。
次いで、同様のフラスコに樹脂(RA)を31.5部、ジペンタエリスリトールヘキサアクリレート68.4部、ハイドロキノン0.1部を混合し、110℃で加熱溶融しワニス(VA)を得た。
さらに、リオノールブルーFG7330(トーヨーカラー社製藍顔料)20部、ワニス(VA)を62部、トリメチロールプロパンテトラアクリレート12.9部、4,4’−ビス(ジエチルアミノ)ベンゾフェノン2.5部、2−メチル−2−モノホリノ(4−チオメチルフェニル)プロパン−1−オン2.5部、ハイドロキノン0.1部を、40℃の三本ロールミルにて練肉し、インキのタックが9〜10になるようにトリメチロールプロパンテトラアクリレートで調整し、平版印刷インキ(CA)を得た。
インキのタックは東洋精機社製インコメーターにてロール温度30℃、400rpm、1分後の値を測定した。
比較例1と同様の操作にて、表1に示す配合組成で酸価29、Mw2.6万の樹脂(RB)を得た。次いで、表2に示す配合組成でワニス(VB)、表3に示す配合組成にて平版印刷インキ(CB)を得た。
比較例1と同様の操作にて、表1に示す配合組成で酸価21、Mw3.0万の樹脂(RC)を得た。次いで、表2に示す配合組成でワニス(VC)、表3に示す配合組成にて平版印刷インキ(CC)を得た。
比較例1と同様の操作にて、表1に示す配合組成で酸価18、Mw2.6万の樹脂(RD)を得た。次いで、表2に示す配合組成でワニス(VD)、表3に示す配合組成にて平版印刷インキ(CD)を得た。
比較例1と同様の操作にて、表1に示す配合組成で酸価33、Mw2.8万の樹脂(RE)を得た。次いで、表2に示す配合組成でワニス(VE)、表3に示す配合組成にて平版印刷インキ(CE)を得た。
比較例1と同様の操作にて、表1に示す配合組成で酸価13、Mw1.8万の樹脂(RF)を得た。次いで、表2に示す配合組成でワニス(VF)、表3に示す配合組成にて平版印刷インキ(CF)を得た。
実施例1〜8、比較例1〜6で得られた平版印刷インキを、RIテスター(明製作所製簡易展色装置)を用いて、マリコート紙(北越製紙社製コートボール紙)へ1g/m2の塗布量で印刷し、120W/cmの空冷メタルハライドランプ(東芝社製)1灯を用いて60m/minで紫外線を照射した。
(評価基準) ◎:60以上、○:50以上〜60未満、△:45以上〜50未満、×:45未満
さらに、耐MEK性、耐摩擦性は樹脂の分子量が大きい実施例2、5、6、7が良好であった。これは、分子量が大きくなることで皮膜強度が増すためと考えられる。
さらに、イソソルビド40重量%以上含有する実施例1、6の平版印刷インキは特に光沢値が優れる結果となった。イソソルビドを含有させることで、インキの流動性が上がり紙面のレベリングが良化するためと考えられる。
Claims (5)
- ロジン類(a)、カルボキシル基を2つ以上有する化合物(b)、イソソルビド(c)、および、ポリオール(d)(ただし、イソソルビド(c)を除く)を反応してなるポリエステル樹脂(A)。
- ポリエステル樹脂(A)全体に対して、
ロジン類(a)5〜25重量%と、
カルボキシル基を2つ以上有する化合物(b)15〜50重量%と、
イソソルビド(c)10〜45重量%と、
ポリオール(d)15〜45重量%とを
反応させてなる請求項1記載のポリエステル樹脂(A)。 - 請求項1又は2記載のポリエステル樹脂(A)を含んでなるインキバインダー。
- 請求項3記載のインキバインダーと、顔料と、アクリレートオリゴマーおよび/またはアクリレートモノマーとを含有してなる活性エネルギー線硬化型平版印刷インキ。
- 請求項4記載の活性エネルギー線硬化型平版印刷インキを基材に印刷し、活性エネルギー線により硬化してなることを特徴とする印刷物。
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CN110028834A (zh) * | 2019-04-30 | 2019-07-19 | 伟岸包装制品(苏州)有限公司 | 纸箱印刷油墨调配及生产方法 |
JP7005834B1 (ja) * | 2020-06-03 | 2022-01-24 | 東洋インキScホールディングス株式会社 | 活性エネルギー線硬化型平版印刷インキ及び印刷物 |
JP2023127524A (ja) * | 2022-03-01 | 2023-09-13 | Dicグラフィックス株式会社 | 活性エネルギー線硬化型オフセット印刷インキ、これを用いた印刷物、及び印刷物の製造方法 |
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