JP5900668B2 - 印刷インキ組成物 - Google Patents
印刷インキ組成物 Download PDFInfo
- Publication number
- JP5900668B2 JP5900668B2 JP2015007901A JP2015007901A JP5900668B2 JP 5900668 B2 JP5900668 B2 JP 5900668B2 JP 2015007901 A JP2015007901 A JP 2015007901A JP 2015007901 A JP2015007901 A JP 2015007901A JP 5900668 B2 JP5900668 B2 JP 5900668B2
- Authority
- JP
- Japan
- Prior art keywords
- printing ink
- glycol
- ink
- printing
- resin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 229920005749 polyurethane resin Polymers 0.000 claims description 44
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- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 17
- 229920000642 polymer Polymers 0.000 claims description 15
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- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 14
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 12
- 229920001228 polyisocyanate Polymers 0.000 claims description 9
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
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- CONKBQPVFMXDOV-QHCPKHFHSA-N 6-[(5S)-5-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-2-oxo-1,3-oxazolidin-3-yl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C[C@H]1CN(C(O1)=O)C1=CC2=C(NC(O2)=O)C=C1 CONKBQPVFMXDOV-QHCPKHFHSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 229920000298 Cellophane Polymers 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000005456 alcohol based solvent Substances 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 150000001414 amino alcohols Chemical class 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
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- 150000002334 glycols Chemical class 0.000 description 3
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- DSKYSDCYIODJPC-UHFFFAOYSA-N 2-butyl-2-ethylpropane-1,3-diol Chemical compound CCCCC(CC)(CO)CO DSKYSDCYIODJPC-UHFFFAOYSA-N 0.000 description 2
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 description 2
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 2
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- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
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- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
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- SDQROPCSKIYYAV-UHFFFAOYSA-N 2-methyloctane-1,8-diol Chemical compound OCC(C)CCCCCCO SDQROPCSKIYYAV-UHFFFAOYSA-N 0.000 description 1
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- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
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- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
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- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
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- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
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- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 1
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- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
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- 239000003208 petroleum Substances 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
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- 229920013716 polyethylene resin Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
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- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
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- 238000001556 precipitation Methods 0.000 description 1
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- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
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- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
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Description
高分子ポリオールとポリイソシアネートとを反応させてなるポリウレタン樹脂を含むノントルエン系印刷インキ用バインダーにおいて、(1)〜(3)を特徴とする印刷インキ用バインダーに関する。
(1)高分子ポリオールが、グリコールおよびアジピン酸からなるポリエステルポリオールを、高分子ポリオール全量に対して50重量%以上含有する。
(2)前記グリコールが、ネオペンチルグリコールおよびエチレングリコールを含有する。
(3)前記グリコールが、グリコール全量に対して、80重量%以上のネオペンチルグリコールを含有する。
I. Pigment No Yellow83を用いることが好ましい。
0070(1996年)に準じて行われる。アミン価の測定方法については、後述の通り行なった。分子量はGPC(ゲルパーミエーションクロマトグラフィー)装置を用いて分子量分布を測定し、ポリスチレン換算分子量として求めた。アミン価の測定方法は、下記の通りである。
試料を0.5〜2g精秤する。(試料量:Sg)精秤した試料に中性エタノール(BDG中性)30mLを加え溶解させる。得られた溶液を0.2mol/lエタノール性塩酸溶液(力価:f)で滴定を行なう。溶液の色が緑から黄に変化した点を終点とし、この時の滴定量(AmL)を用い次の(式1)によりアミン価を求めた。
(式1) アミン価=(A×f×0.2×56.108)/S
攪拌機、温度計、分水器および窒素ガス導入管を備えた丸底フラスコに、ネオペンチルグリコール40.86部、エチレングリコール2.15部、アジピン酸56.99部、テトラブチルチタネート0.002部を仕込み、窒素気流下に230℃で縮合により生じる水を除去しながらエステル化を8時間行った。ポリエステルの酸価が15以下になったことを確認後、真空ポンプにより徐々に真空度を上げ反応を終了した。これにより水酸基価22.4mgKOH/g(水酸基価から算出される数平均分子量5000)、酸価0.3mgKOH/gのポリエステルジオ−ル(PES5)を得た。
表1、表2の仕込み比にて、合成例5−1と同様の操作で、ポリエステルジオ−ルを得た。尚、数平均分子量については合成例5−1と同じく水酸基価から算出した。
攪拌機、温度計、還流冷却器および窒素ガス導入管を備えた四つ口フラスコに、ポリエステルジオ−ル(PES5)18.550部、数平均分子量2000のポリプロピレングリコール(以下PPG2000と表記する)3.174部、イソホロンジイソシアネート2.352部を仕込み、窒素気流下に120℃で6時間反応させ、酢酸n−プロピル10.000部を加え冷却し、末端イソシアネートプレポリマーの溶液34.076部を得た。次いでイソホロンジアミン0.910部、ジn−ブチルアミン0.014部、酢酸n−プロピル46.250部およびイソプロピルアルコール18.750部を混合したものへ、得られた末端イソシアネートプレポリマーの溶剤溶液34.076部を室温で徐々に添加し、次に50℃で1時間反応させポリウレタン樹脂溶液(PU5)を得た。
表3〜6の仕込み比にて、合成例5−2と同様の操作で、ポリウレタン樹脂溶液を得た。
チタニックスJR−805(テイカ社製)30部、ポリウレタン樹脂溶液(PU5)10部、酢酸n−プロピル/イソプロピルアルコール混合溶剤(重量比75/25)10.0部を撹拌混合しサンドミルで練肉した後、ポリウレタン樹脂溶液(PU5)40部、酢酸n−プロピル/イソプロピルアルコール混合溶剤(重量比75/25)10.0部を攪拌混合し白色印刷インキ(W5)を得た。得られた白色印刷インキ(W5)100部に、酢酸n−プロピル/イソプロピルアルコール混合溶剤(重量比75/25)50部を希釈溶剤として添加混合し、白色希釈印刷インキ(WD5)を得た。
実施例6、7、比較例1〜5については対応するポリウレタン樹脂(PU6、7、PU9〜13)を用い実施例5と同様な方法で白色印刷インキW6、7、W9〜13、及びそれらの希釈インキである白色希釈印刷インキ(WD6、7、WD9〜13)を得た。表7,8に配合を示す。
銅フタロシアニン藍(リオノールブルーKLH 東洋インキ製造(株)社製)12部、ポリウレタン樹脂溶液(PU18)20部、酢酸n−プロピル/イソプロピルアルコール混合溶剤(重量比70/30)10部を撹拌混合しサンドミルで練肉した後、ポリウレタン樹脂溶液(PU18)20部、酢酸n−プロピル/イソプロピルアルコール混合溶剤(重量比70/30)38部を攪拌混合し、藍色印刷インキ(C5)を得た。得られた藍色印刷インキ(C5)100部に、酢酸n−プロピル/イソプロピルアルコール混合溶液(重量比70/30)50部を希釈溶剤として添加混合し、藍色希釈印刷インキ(CD5)を得た。
実施例14、15、比較例6〜10については対応するポリウレタン樹脂(PU15〜21)、PU22〜26)を用い実施例13と同様な方法で藍色印刷インキC6、7、9〜13、及びそれらの希釈インキである藍色希釈印刷インキ(CD6、7、9〜13)を得た。表9,10に配合を示す。
評価方法と評価基準は下記の通りである。結果を表11、12に示す。
ポリウレタン樹脂溶液を評価した。ポリウレタン樹脂溶液自身も、生産効率上、低温での流動性が必要とされる。得られたポリウレタン樹脂溶液(PU5〜7、9〜13、18〜20、22〜26)を50gを70gガラス製サンプル瓶に入れ、−5℃の恒温槽にて12時間放置後、低温安定性を次の基準に従って評価した。
○ :外観は透明のままで、流動性が有る。
○△:やや不透明になる
△ :白濁し、流動性が低下する。
△×:分離、沈殿する。
× :固化、及びゲル化する。
実用レベルは〇である。
NBR(ニトリルブタジエンゴム)製のゴム硬度80Hsの圧胴、刃先の厚みが60μm(母材の厚み40μm、片側セラミック層の厚み10μm)のセラミックメッキドクターブレード、東洋プリプレス株式会社製のクロム硬度1050Hvの電子彫刻版(スタイラス角度120度、色インキ用:250線/inch、白インキ用:200線/inch)、および実施例1〜16および比較例1〜10で得られた希釈印刷インキを富士機械工業株式会社製グラビア印刷機にセットしドクター圧2kg/cm2、100m/分の回転速度で版を60分間空転した後に、片面コロナ処理OPPフィルム「パイレンP2161(東洋紡績株式会社製)」のコロナ処理面に、印刷速度100m/分で印圧2kg/cm2で印刷、60℃の熱風で乾燥し、印刷物を得た。印刷中は、粘度コントローラーを用いて、各々の希釈溶剤を適宜補充して一定の粘度を保っている。
印刷物を4cm×4cmにサンプリングし、このサンプルの印刷面と同じ大きさの未印刷フィルムの非処理面とを合わせて、40℃12時間、10kgfの加圧を行い、サンプルを剥離した時の、インキ取られと抵抗感とを観察した。
◎ :印刷物からインキの転移が全く認められず、剥離時の抵抗感もなかった。
〇 :印刷物からインキの転移が全く認められず、剥離時の抵抗感も少なかった。
○△:印刷物からインキの転移が全く認められなかった。
△ :印刷物からインキの転移がわずかに認められた。
△×:印刷物からインキの転移が、面積にして50%程度認められた。
× :印刷物からインキの転移が、ほとんどの面積で認められた。
実用レベルは〇である。
2.接着性
印刷物皮膜にセロハンテープ(ニチバン製、幅12mm)を貼り付け親指で5回強く擦った後、セロハンテープを徐々に引き離し途中から、急激に引き離してインキ皮膜の剥離の程度を調べた。
○ :急激に引き離しても全くインキの剥離が認められない。
○△:急激に引き離すとインキの剥離が僅かに認められた。
△ :ゆっくり引き離しても全くインキの剥離が認められないが、急激に引き離すと
インキの剥離が認められた。
△×:ゆっくり引き離しても50%程度の面積のインキの剥離が認められた。
× :ゆっくり引き離してもほとんどのインキの剥離が認められた。
実用レベルは〇である。
Claims (4)
- 高分子ポリオールとポリイソシアネートとを反応させてなるポリウレタン樹脂を含むノントルエン系印刷インキ用バインダーにおいて、(1)〜(3)を特徴とする印刷インキ用バインダー。
(1)高分子ポリオールが、グリコールおよびアジピン酸からなるポリエステルポリオールを、高分子ポリオール全量に対して50重量%以上含有する。
(2)前記グリコールが、ネオペンチルグリコールおよびエチレングリコールを含有する。
(3)前記グリコールが、グリコール全量に対して、80重量%以上のネオペンチルグリコールを含有する。 - 請求項1記載の印刷インキ用バインダーを含有するノントルエン系印刷インキ組成物。
- 基材上に、請求項2記載の印刷インキ組成物を印刷してなる皮覆物。
- 請求項3記載の皮覆物の印刷面にラミネートしてなるラミネート積層物。
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