JP2018016688A - 活性エネルギー線硬化型インキ用樹脂、活性エネルギー線硬化型インキ用組成物、活性エネルギー線硬化型インキおよび硬化膜 - Google Patents
活性エネルギー線硬化型インキ用樹脂、活性エネルギー線硬化型インキ用組成物、活性エネルギー線硬化型インキおよび硬化膜 Download PDFInfo
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Classifications
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- 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
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/91—Polymers modified by chemical after-treatment
- C08G63/914—Polymers modified by chemical after-treatment derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/918—Polycarboxylic acids and polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L93/00—Compositions of natural resins; Compositions of derivatives thereof
- C08L93/04—Rosin
-
- 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
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
- C09D11/037—Printing inks characterised by features other than the chemical nature of the binder characterised by the pigment
-
- 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
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/102—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions other than those only involving unsaturated carbon-to-carbon bonds
- C09D11/104—Polyesters
-
- 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
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
- C09D167/06—Unsaturated polyesters having carbon-to-carbon unsaturation
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
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Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Polyesters Or Polycarbonates (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
Description
不飽和結合モル比率が上記下限を上回っていれば、ロジン変性不飽和ポリエステル樹脂(A)中におけるα,β−不飽和カルボン酸類(b)由来の不飽和結合の含有割合が比較的多いため、活性エネルギー線硬化型モノマー(後述)との反応点(架橋点)が比較的多くなる。そのため、優れた機械強度(硬度)の硬化膜を得ることができる。また、不飽和結合モル比率が上記上限を下回っていれば、優れた保存安定性を確保することができる。
攪拌機、水分離器付き還流冷却器および温度計付き4つ口フラスコに窒素ガスを吹き込みながら、不均化ロジン(商品名G−100F、ハリマ化成製)7.0部、パラ−t−ブチル安息香酸35.0部、無水マレイン酸13.0部、フタル酸13.0部、トリメチロールプロパン32.0部を混合し、230℃で約8時間脱水縮合させ、酸価8.0mgKOH/g以下の活性エネルギー線硬化型インキ用樹脂(以下、樹脂と略する。)1を得た。
表1の配合比率に変更した以外は、実施例1と同様の操作で、樹脂2〜7および樹脂9〜11を得た。
攪拌機、水分離器付き還流冷却器および温度計付き4つ口フラスコに窒素ガスを吹き込みながら、不均化ロジン(商品名G−100F、ハリマ化成製)29.0部、無水マレイン酸10.7部、安息香酸25.0部、テトラヒドロフタル酸11.3部、および、グリセリン23.6部を混合し、230℃で約8時間脱水縮合させ、酸価8.0以下にした。その後、冷却し、ハイドロキノン0.1部、アクリル酸0.3部を添加し110℃で約12時間反応させ、酸価8.0mgKOH/g以下の樹脂8を得た。
表2の配合比率に変更した以外は、実施例1と同様の操作で、樹脂12〜13および樹脂16〜18を得た。
表2の配合比率に変更した以外は、実施例8と同様の操作で、樹脂14および15を得た。
各実施例および各比較例において得られたワニスを、下記の方法により評価した。
ワニスを約60℃で保管し、ゲル化の有無を目視で確認した。評価の基準を下記する。
A: 1か月後ゲル化しなかった。
B: 10日目以降ゲル化した。
C: 3日目以降ゲル化した。
各実施例および各比較例において得られたインキを、下記の方法により評価した。
0.4mLの各インキをRIテスター全面ロールでアート紙に展色した。その後、UV照射装置(アイグラフィック(株)社製ESC−4011GX)を用いて、メタルハライドランプ80W/cm、コンベアスピード24m/minの条件で、紫外線を照射し、印刷物を硬化させた。また硬化後の印刷物の光沢値を60°−60°光沢計(太佑機材(株)製マイクロトリグロス)で測定した。尚、本試験で光沢値60以上であれば、高い光沢値を有していると判断した。
光沢値測定時と同条件で作成した硬化後の印刷物をJIS K5600(2007年)に準拠し、三菱鉛筆「ユニ」により印刷物皮膜が乖離しない最高硬度を評価した。
また、上記の基準において、F以上であれば実用可能であると判断した。
光沢値測定時と同条件で作成した硬化後の印刷物をJIS K5701−1(2000)に準拠し、S形摩擦試験機((株)安田精機製作所製)を使用して、1816gの加重で40回往復させ、印刷物表面のインキ皮膜の擦れ落ち度合いを5段階で評価した。その基準を下記する。
5:40回往復で擦れ落ちが20%未満であった。
4:40回往復で擦れ落ちが20%以上40%未満であった。
3:40回往復で擦れ落ちが40%以上60%未満であった。
2:40回往復で擦れ落ちが60%以上80%未満であった。
1:40回往復で擦れ落ちが80%以上であった。
各インキを約360mL取り、インコメーター(東洋精機社製 D−2)に均一となるように載せて、1200rpm、ロール温度30℃で回転させ、ロール前面と下面においた白紙に付着したインキの飛散状態を目視確認し、5段階で評価した。その基準を下記する。
5:インキの飛散が殆どなかった。
4:インキの飛散が僅かにあった。
3:インキの飛散はあるが実使用可能であった。
2:インキの飛散が多かった。
1:インキの飛散が著しく激しかった。
DPHA:ジペンタエリスリトールヘキサアクリレート
TMPTA:トリメチロールプロパントリアクリレート
CB:カーボンブラック
イルガキュア907:光重合開始剤、2−メチル−1−(4−メチルチオフェニル)−2−モルフォリノプロパン−1−オン、BASF社製
Claims (10)
- ロジン変性不飽和ポリエステル樹脂(A)を含有する活性エネルギー線硬化型インキ用樹脂であって、
前記ロジン変性不飽和ポリエステル樹脂(A)は、ロジン類(a)、α,β−不飽和カルボン酸類(b)およびポリオール類(c)を含む原料成分の反応物であり、
前記原料成分の総量に対する、前記α,β−不飽和カルボン酸類(b)由来の不飽和結合モル比率が0.50mol/kg以上2.00mol/kg以下であり、
前記ロジン類(a)は、前記ロジン類(a)の総量に対して、安定化処理ロジンを90質量%以上含有し、
前記α,β−不飽和カルボン酸類(b)は、α,β−不飽和ジカルボン酸類を含有し、
前記ポリオール類(c)は、3価以上のアルコールを含有する
ことを特徴とする、活性エネルギー線硬化型インキ用樹脂。 - 前記α,β−不飽和カルボン酸類(b)の総量に対して、α,β−不飽和モノカルボン酸類の含有割合が、3質量%以下である、請求項1に記載の活性エネルギー線硬化型インキ用樹脂。
- 前記ポリオール類(c)の総量に対して、ジオールの含有割合が、10質量%以下である、請求項1または2に記載の活性エネルギー線硬化型インキ用樹脂。
- 前記α,β−不飽和ジカルボン酸類が、フマル酸、マレイン酸および無水マレイン酸からなる群から選択される少なくとも1種の化合物である、請求項1〜3のいずれか一項に記載の活性エネルギー線硬化型インキ用樹脂。
- 前記安定化処理ロジンが、水添ロジンおよび/または不均化ロジンである、請求項1〜4のいずれか一項に記載の活性エネルギー線硬化型インキ用樹脂。
- 前記ロジン類(a)に対する前記α,β−不飽和カルボン酸類(b)の質量比率(前記α,β−不飽和カルボン酸類(b)/前記ロジン類(a))が、0.35以上2以下である、請求項1〜5のいずれか一項に記載の活性エネルギー線硬化型インキ用樹脂。
- 請求項1〜6のいずれか一項に記載の活性エネルギー線硬化型インキ用樹脂と、
活性エネルギー線硬化型モノマーと
を含有することを特徴とする、活性エネルギー線硬化型インキ用組成物。 - 請求項7に記載の活性エネルギー線硬化型インキ用組成物と、
顔料と
を含有することを特徴とする、活性エネルギー線硬化型インキ。 - 請求項7に記載の活性エネルギー線硬化型インキ用組成物の硬化物であることを特徴とする、硬化膜。
- 請求項8に記載の活性エネルギー線硬化型インキの硬化物であることを特徴とする、硬化膜。
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ES17834053T ES2955712T3 (es) | 2016-07-26 | 2017-07-13 | Resina para tintas curables con rayos de energía activa, composición para tintas curables con rayos de energía activa, tinta curable con rayos de energía activa y película curada |
US16/320,304 US10669439B2 (en) | 2016-07-26 | 2017-07-13 | Resin for active energy ray curable ink, composition for active energy ray curable ink, active energy ray curable ink, and cured film |
CN201780042020.7A CN109476940B (zh) | 2016-07-26 | 2017-07-13 | 活性能量射线固化型油墨用树脂、油墨用组合物、油墨及固化膜 |
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