JP2018072456A - 凸版印刷原版用感光性樹脂組成物、及びそれから得られる凸版印刷原版 - Google Patents
凸版印刷原版用感光性樹脂組成物、及びそれから得られる凸版印刷原版 Download PDFInfo
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- JP2018072456A JP2018072456A JP2016209275A JP2016209275A JP2018072456A JP 2018072456 A JP2018072456 A JP 2018072456A JP 2016209275 A JP2016209275 A JP 2016209275A JP 2016209275 A JP2016209275 A JP 2016209275A JP 2018072456 A JP2018072456 A JP 2018072456A
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- Prior art keywords
- photosensitive resin
- water
- resin composition
- polyamide
- meth
- Prior art date
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- 238000007639 printing Methods 0.000 title claims abstract description 89
- 239000011342 resin composition Substances 0.000 title claims abstract description 46
- 239000002243 precursor Substances 0.000 title claims abstract description 8
- 239000004952 Polyamide Substances 0.000 claims abstract description 66
- 229920002647 polyamide Polymers 0.000 claims abstract description 66
- 150000001875 compounds Chemical class 0.000 claims abstract description 44
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- 239000003999 initiator Substances 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 4
- 239000011347 resin Substances 0.000 claims description 22
- 229920005989 resin Polymers 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 18
- 150000004985 diamines Chemical class 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 125000002723 alicyclic group Chemical group 0.000 claims description 13
- 238000007644 letterpress printing Methods 0.000 claims description 13
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 150000003863 ammonium salts Chemical class 0.000 claims description 5
- 229920002614 Polyether block amide Polymers 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 229920006146 polyetheresteramide block copolymer Polymers 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 28
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- -1 alicyclic diamine Chemical class 0.000 description 24
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- 239000007795 chemical reaction product Substances 0.000 description 18
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 13
- 238000011156 evaluation Methods 0.000 description 12
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 11
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- 235000005985 organic acids Nutrition 0.000 description 7
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 6
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- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
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- 239000000463 material Substances 0.000 description 5
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 5
- 238000012719 thermal polymerization Methods 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
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- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
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- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- DPNXHTDWGGVXID-UHFFFAOYSA-N 2-isocyanatoethyl prop-2-enoate Chemical compound C=CC(=O)OCCN=C=O DPNXHTDWGGVXID-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 235000000126 Styrax benzoin Nutrition 0.000 description 3
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- 125000004193 piperazinyl group Chemical group 0.000 description 3
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- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 2
- DBRHKXSUGNZOLP-UHFFFAOYSA-N 2-(2-isocyanatoethoxy)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCN=C=O DBRHKXSUGNZOLP-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-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
- XUSNPFGLKGCWGN-UHFFFAOYSA-N 3-[4-(3-aminopropyl)piperazin-1-yl]propan-1-amine Chemical compound NCCCN1CCN(CCCN)CC1 XUSNPFGLKGCWGN-UHFFFAOYSA-N 0.000 description 2
- ORTCGSWQDZPULK-UHFFFAOYSA-N 3-isocyanatopropyl prop-2-enoate Chemical compound C=CC(=O)OCCCN=C=O ORTCGSWQDZPULK-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
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- QLBRROYTTDFLDX-UHFFFAOYSA-N [3-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCCC(CN)C1 QLBRROYTTDFLDX-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
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Landscapes
- Macromonomer-Based Addition Polymer (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Materials For Photolithography (AREA)
- Polyamides (AREA)
- Polymerisation Methods In General (AREA)
Abstract
Description
(1)少なくとも(A)水分散性又は水溶性のポリアミド、(B)光重合性不飽和化合物、及び(C)光重合開始剤を含む凸版印刷原版用感光性樹脂組成物であって、(A)水分散性又は水溶性のポリアミドが、分子鎖末端に以下の式Iの構造単位を有することを特徴とする凸版印刷原版用感光性樹脂組成物。
式中、A1は炭素数2〜4のアルキレン基又は−CH2CH2OCH2CH2−を示し、R1は水素又はメチル基を示す。
(2)(A)水分散性又は水溶性のポリアミドが、式Iの構造単位をポリアミド1kg当たり0.03〜0.5モル含有することを特徴とする、(1)に記載の凸版印刷原版用感光性樹脂組成物。
(3)(A)水分散性又は水溶性のポリアミドが、ポリエーテルアミド、ポリエーテルエステルアミド、三級窒素含有ポリアミド、又はアンモニウム塩型三級窒素原子含有ポリアミドであることを特徴とする、(1)又は(2)に記載の凸版印刷原版用感光性樹脂組成物。
(4)(A)水分散性又は水溶性のポリアミドが、ジアミン及びジカルボン酸から得られる脂環族構造単位を30〜90モル%含有することを特徴とする、(1)〜(3)のいずれかに記載の凸版印刷原版用感光性樹脂組成物。
(5)(1)〜(4)のいずれかに記載の凸版印刷原版用感光性樹脂組成物からなる感光性樹脂層を設けていることを特徴とする凸版印刷原版。
式中、A1は炭素数2〜4のアルキレン基又は−CH2CH2OCH2CH2−を示し、R1は水素又はメチル基を示す。
まず、感光層厚みが685μmの感光性樹脂凸版原版に、画像として網点175線−1%〜95%、最小独立点直径50〜600μm、最小独立線幅が10〜150μm、ベタ画像(幅1cm×長さ5cm)を含む印刷評価ネガを用い、175線−1%が再現する最小露光時間を最適露光時間として、25W/m2のケミカルランプを用いて感光性樹脂表面より高さ5cmの距離から露光した。次にブラシ式ウォッシャー(120μmφナイロンブラシ、日本電子精機(株)制作JW−A2−PD型)で25℃の水道水で現像し、レリーフ画像を得た。更に70℃で10分間、温風乾燥した後に超高圧水銀灯で30秒間後露光して印刷版を得た。175線−1%の画像再現性は10倍のルーペを使い、肉眼で判定した。得られた印刷版を用いてハイライト印刷性の評価を行った。印刷機には、輪転印刷機P−20(三條機械製)を用い、インキにはベストキュア藍(T&K TOKA製)、被印刷物にはグロスPW−8K(リンテック製)を用いた。印圧(版と被印刷物間の圧力)を段階的に高め、ベタ箇所のカスレが無くなる箇所を適性印圧として印刷評価を実施した。また、ベタ箇所のインキ濃度が1.7absになるようにインク送り量を調整した。適性圧での175線1%〜5%の網点濃度を、CCDOT4(エス・デェイ・ジー株式会社製)を用いて測定し、その結果を%で表して表1にまとめた。測定した印刷物の網点濃度は、ネガフィルムの網点濃度に近い方が良く、さらにはネガフィルム網点が5%から1%へ減少するのに応じて印刷物の網点濃度もスムーズに減少していくことが好ましい。このように、印刷物の網点濃度がスムーズに減少する場合には、ハイライトの階調性が優れるとの評価となる。
(1)のハイライト部印刷性評価用レリーフを作成した時と同じ方法で印刷版を製造し、適性印圧から100μm加圧した状態で印刷を行った。印刷物にクラックが確認された印刷ショット数を表1にまとめた。ショット数が多いほど耐刷性に優れることを示す。
(ポリアミドの合成)
ε−カプロラクタム339質量部、シクロヘキサンジカルボン酸596質量部、メチルイミノビスプロピルアミン514質量部、50%次亜リン酸水溶液5質量部、及び水1000質量部をオートクレーブ中に仕込み、窒素置換後、密閉して徐々に加熱した。内圧が0.4MPaに達した時点から、その圧力を保持できなくなるまで水を留出させ、約2時間で常圧に戻し、その後1時間常圧で反応させた。最高重合反応温度は255℃であった。これにより、相対粘度2.10のポリアミドを得た。ポリアミドの組成をH−NMRで測定し、仕込み組成とポリマー組成に差異がないことを確認した。
得られたポリアミド1000質量部をメタノール1000質量部に溶解後、イソシアネート基含有エチレン性不飽和化合物としてカレンズMOI(2−イソシアナトエチルメタクリレート、昭和電工(株)製)をポリマー1kg当たり0.18モルとなる量を200g/分の速度で滴下し、ポリアミド主鎖末端のアミノ基とカレンズMOIのイソシアナト基を反応させた。なお、付加反応の完了は、IRスペクトルにおける2,250cm−1のイソシアナト基由来のピークの消失により確認した。
引き続いて、イソシアネート基含有エチレン性不飽和化合物を付加させたポリアミド55質量部にトリメチロールプロパントリグリシジルエステルのアクリル酸付加物40.0質量部、乳酸4質量部、ハイドロキノンモノメチルエーテル0.1質量部、2,2’,4,4’−テトラヒドロキシベンゾフェノン0.02質量部およびベンジルメチルケタール1.0質量部を添加して30分間攪拌した。次いで、徐々に昇温してメタノールを留出させ、釜内の温度が110℃となるまで濃縮し、流動性のある粘稠なアンモニウム塩型三級窒素原子含有ポリアミドを含有する感光性樹脂組成物を得た。
イソシアネート基含有エチレン性不飽和化合物としてカレンズAOI(2−イソシアナトエチルアクリレート、昭和電工(株)製)を用いたこと以外は実施例1と同様にして、感光性樹脂組成物を作成し、印刷原版を得た。得られた印刷原版について、実施例1と同様の評価を行なった。評価結果を表1に示す。
イソシアネート基含有エチレン性不飽和化合物としてカレンズMOI−EG(2−イソシアナトエトキシエチルメタクリレート、昭和電工(株)製)を用いたこと以外は実施例1と同様にして、感光性樹脂組成物を作成し、印刷原版を得た。得られた印刷原版について、実施例1と同様の評価を行なった。評価結果を表1に示す。
イソシアネート基含有エチレン性不飽和化合物としてアクロイルオキシプロピルイソシアネート(特許第4823546号の実施例6に従って製造)を用いたこと以外は実施例1と同様にして、感光性樹脂組成物を作成し、印刷原版を得た。得られた印刷原版について、実施例1と同様の評価を行なった。評価結果を表1に示す。
イソシアネート基含有エチレン性不飽和化合物の含有量を表1に示すように変更させたこと以外は実施例1と同様にして、感光性樹脂組成物を作成し、印刷原版を得た。得られた印刷原版について、実施例1と同様の評価を行なった。評価結果を表1に示す。
水分散性又は水溶性のポリアミドの種類(原料化合物、及びその配合割合)を表1に示すように変更させたこと以外は実施例1と同様にして、感光性樹脂組成物を作成し、印刷原版を得た。得られた印刷原版について、実施例1と同様の評価を行なった。評価結果を表1に示す。
イソシアネート基含有エチレン性不飽和化合物を全く導入しなかった以外は実施例1と同様にして、感光性樹脂組成物を作成し、印刷原版を得た。得られた印刷原版について、実施例1と同様の評価を行なった。評価結果を表1に示す。
イソシアネート基含有エチレン性不飽和化合物として6−イソシアナトヘキシルメタクリレートを用いたことを以外は実施例1と同様にして、感光性樹脂組成物を作成し、印刷原版を得た。得られた印刷原版について、実施例1と同様の評価を行なった。評価結果を表1に示す。
イソシアネート基含有エチレン性不飽和化合物として2−ヒドロキシエチルアクリレートとヘキサメチレンジイソシアネートとの当モル反応物を用いたこと以外は実施例1と同様にして、感光性樹脂組成物を作成し、印刷原版を得た。得られた印刷原版について、実施例1と同様の評価を行なった。評価結果を表1に示す。
Claims (5)
- (A)水分散性又は水溶性のポリアミドが、式Iの構造単位をポリアミド1kg当たり0.03〜0.5モル含有することを特徴とする、請求項1に記載の凸版印刷原版用感光性樹脂組成物。
- (A)水分散性又は水溶性のポリアミドが、ポリエーテルアミド、ポリエーテルエステルアミド、三級窒素含有ポリアミド、又はアンモニウム塩型三級窒素原子含有ポリアミドであることを特徴とする、請求項1又は2に記載の凸版印刷原版用感光性樹脂組成物。
- (A)水分散性又は水溶性のポリアミドが、ジアミン及びジカルボン酸から得られる脂環族構造単位を30〜90モル%含有することを特徴とする、請求項1〜3のいずれかに記載の凸版印刷原版用感光性樹脂組成物。
- 請求項1〜4のいずれかに記載の凸版印刷原版用感光性樹脂組成物からなる感光性樹脂層を設けていることを特徴とする凸版印刷原版。
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