JP4973130B2 - 印刷インキ用組成物 - Google Patents
印刷インキ用組成物 Download PDFInfo
- Publication number
- JP4973130B2 JP4973130B2 JP2006299760A JP2006299760A JP4973130B2 JP 4973130 B2 JP4973130 B2 JP 4973130B2 JP 2006299760 A JP2006299760 A JP 2006299760A JP 2006299760 A JP2006299760 A JP 2006299760A JP 4973130 B2 JP4973130 B2 JP 4973130B2
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- JP
- Japan
- Prior art keywords
- parts
- component
- general formula
- polyurethane resin
- alcohol
- 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.)
- Expired - Fee Related
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- 238000007639 printing Methods 0.000 title claims description 17
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 29
- 125000002947 alkylene group Chemical group 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- 150000002440 hydroxy compounds Chemical class 0.000 claims description 14
- 150000001298 alcohols Chemical class 0.000 claims description 13
- 239000004970 Chain extender Substances 0.000 claims description 10
- 239000005056 polyisocyanate Substances 0.000 claims description 7
- 229920001228 polyisocyanate Polymers 0.000 claims description 7
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- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 150000003462 sulfoxides Chemical class 0.000 claims description 2
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- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 12
- 239000000853 adhesive Substances 0.000 description 12
- 230000001070 adhesive effect Effects 0.000 description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 12
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 12
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- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 8
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- 239000005058 Isophorone diisocyanate Substances 0.000 description 7
- 125000005442 diisocyanate group Chemical group 0.000 description 7
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 7
- 239000003973 paint Substances 0.000 description 7
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- 239000004814 polyurethane Substances 0.000 description 7
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- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
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- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 6
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- 238000011156 evaluation Methods 0.000 description 5
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- 239000002904 solvent Substances 0.000 description 5
- JVYDLYGCSIHCMR-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)butanoic acid Chemical compound CCC(CO)(CO)C(O)=O JVYDLYGCSIHCMR-UHFFFAOYSA-N 0.000 description 4
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 239000004743 Polypropylene Substances 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
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- 238000012644 addition polymerization Methods 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 239000000539 dimer Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 239000013110 organic ligand Substances 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 229920005604 random copolymer Polymers 0.000 description 4
- UHAMPPWFPNXLIU-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)pentanoic acid Chemical compound CCCC(CO)(CO)C(O)=O UHAMPPWFPNXLIU-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000007646 gravure printing Methods 0.000 description 3
- 229940035429 isobutyl alcohol Drugs 0.000 description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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- 238000007142 ring opening reaction Methods 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
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- ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 2
- BDLXTDLGTWNUFM-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxy]ethanol Chemical compound CC(C)(C)OCCO BDLXTDLGTWNUFM-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- GMRFGPHHDYBTCX-UHFFFAOYSA-N 4,4-bis(2-hydroxyphenyl)butanoic acid Chemical compound C=1C=CC=C(O)C=1C(CCC(=O)O)C1=CC=CC=C1O GMRFGPHHDYBTCX-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 2
- MVFNWZHRHUOGKQ-UHFFFAOYSA-N 4-methyl-1,7-dioxacyclotridecane-8,13-dione Chemical compound CC1CCOC(=O)CCCCC(=O)OCC1 MVFNWZHRHUOGKQ-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- RBNPOMFGQQGHHO-UWTATZPHSA-N D-glyceric acid Chemical compound OC[C@@H](O)C(O)=O RBNPOMFGQQGHHO-UWTATZPHSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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- XCOBTUNSZUJCDH-UHFFFAOYSA-B lithium magnesium sodium silicate Chemical compound [Li+].[Li+].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Na+].[Na+].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3 XCOBTUNSZUJCDH-UHFFFAOYSA-B 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
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Landscapes
- Adhesives Or Adhesive Processes (AREA)
- Polyurethanes Or Polyureas (AREA)
- Paints Or Removers (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Description
なお、一般式(1)で表されるアルコール類(a)中、一般式(2)で表される繰り返し単位の繰り返し数mが、1〜500の整数および一般式(3)で表される繰り返し単位の繰り返し数nが1〜1000の整数となるようにすることが好ましい。mは2〜200がより好ましく、2〜50が特に好ましく、nは、2〜200がより好ましく、2〜50が特に好ましい。
攪拌機、温度計および窒素ガス導入管を備えた丸底フラスコに、数平均分子量2,000のε-カプロラクトン(含有量50%)とプロピレンオキシド(含有量50%)のランダム共重合ポリオール(商品名:アドバノールADL−X1400:旭硝子(株)製)1,000部とイソホロンジイソシアネート222部を仕込み、窒素気流下に100℃で6時間反応させ遊離イソシアネート価3.44%のプレポリマーとなし、これにメチルエチルケトン523部を加えてウレタンプレポリマーの均一溶液とした。次いで、イソホロンジアミン73.8部、ジ−n−ブチルアミン16.9部、メチルエチルケトン1,518部およびイソプロピルアルコール1,020部からなる混合物の存在下に上記ウレタンプレポリマー溶液1,745部を添加し、50℃で3時間反応させた。こうして得られたポリウレタン樹脂溶液は、樹脂固形分濃度が30%、粘度が400mPa・s/25℃、数平均分子量(ゲルパーメーションクロマトグラフィーによるポリスチレン換算値、以下同じ)は18,000であった。
攪拌機、温度計および窒素ガス導入管を備えた丸底フラスコに、数平均分子量2,000のε-カプロラクトン(含有量50%)とプロピレンオキシド(含有量50%)のランダム共重合ポリオール(商品名:アドバノールADL−X1400:旭硝子(株)製)500部、数平均分子量2,000のポリ(3−メチル−1,5−ペンチレンアジペート)グリコール(商品名:クラレポリオールP2010:(株)クラレ製)500部とイソホロンジイソシアネート222部を仕込み、窒素気流下に100℃で6時間反応させ遊離イソシアネート価3.44%のプレポリマーとなし、これにメチルエチルケトン523部を加えてウレタンプレポリマーの均一溶液とした。次いで、イソホロンジアミン73.8部、ジ−n−ブチルアミン16.9部、メチルエチルケトン1,518部およびイソプロピルアルコール1,020部からなる混合物の存在下に上記ウレタンプレポリマー溶液1,745部を添加し、50℃で3時間反応させた。こうして得られたポリウレタン樹脂溶液は、樹脂固形分濃度が30%、粘度が500mPa・s/25℃、数平均分子量は20,000であった。
攪拌機、温度計および窒素ガス導入管を備えた丸底フラスコに、数平均分子量2,000のポリ(3−メチル−1,5−ペンチレンアジペート)グリコール(商品名:クラレポリオールP2010:(株)クラレ製)1,000部とイソホロンジイソシアネート222部を仕込み、窒素気流下に100℃で6時間反応させ遊離イソシアネート価3.44%のプレポリマーとなし、これにメチルエチルケトン523部を加えてウレタンプレポリマーの均一溶液とした。次いで、イソホロンジアミン73.8部、ジ−n−ブチルアミン16.9部、メチルエチルケトン1,518部およびイソプロピルアルコール1,020部からなる混合物の存在下に上記ウレタンプレポリマー溶液1,745部を添加し、50℃で3時間反応させた。こうして得られたポリウレタン樹脂溶液は、樹脂固形分濃度が30%、粘度が600mPa・s/25℃、数平均分子量は21,000であった。
攪拌機、温度計および窒素ガス導入管を備えた丸底フラスコに、数平均分子量2,000のポリプロピレングリコール(商品名:アデカポリエーテルP2000:(株)ADEKA製)5000部と数平均分子量2,000のポリオキシテトラメチレングリコール(商品名:PTMG2000:三菱化学(株)製)500部とイソホロンジイソシアネート222部を仕込み、窒素気流下に100℃で6時間反応させ遊離イソシアネート価3.44%のプレポリマーとなし、これにメチルエチルケトン523部を加えてウレタンプレポリマーの均一溶液とした。次いで、イソホロンジアミン73.8部、ジ−n−ブチルアミン16.9部、メチルエチルケトン1,518部およびイソプロピルアルコール1,020部からなる混合物の存在下に上記ウレタンプレポリマー溶液1,745部を添加し、50℃で3時間反応させた。こうして得られたポリウレタン樹脂溶液は、樹脂固形分濃度が30%、粘度が400mPa・s/25℃、数平均分子量は17,000であった。
チタン白(ルチル型)30部、酢酸エチル10部、メチルエチルケトン10部、イソプロピルアルコール10部、製造例1〜2および比較製造例1〜2で得られたポリウレタン樹脂溶液を40部、それぞれペイントシェイカーで練肉して白色印刷インキを調製した。製造例1〜2および比較製造例1〜2で得られたポリウレタン樹脂を用いた印刷インキを、それぞれ評価例1〜2および比較評価例1〜2とする。
◎:全く剥れなかった。
〇:インキ皮膜の80%以上がフィルムに残った。
△:インキ皮膜の50%以上80%未満がフィルムに残った。
×:インキ皮膜の50%未満がフィルムに残った。
○:インキ塗膜がすぐに溶解を始めた。
△:インキ塗膜が徐々に溶解した。
×:インキ塗膜がほとんど溶解しなかった。
攪拌機、温度計および窒素ガス導入管を備えた丸底フラスコに、数平均分子量2,000のε-カプロラクトン(含有量50%)とプロピレンオキシド(含有量50%)のランダム共重合ポリオール(商品名:アドバノールADL−X1400:旭硝子(株)製)1,010部、ジメチロールブタン酸99部、イソホロンジイソシアネート391部を仕込み、窒素気流下に70℃で6時間反応させ遊離イソシアネート価3.29%のプレポリマーを得た。次いで、イソプロピルアルコール233部、イソホロンジアミン81部、ジ−n−ブチルアミン28部、28%アンモニア水41部および水2705部からなる混合物の存在下に上記ウレタンプレポリマー1,495部を添加し、50℃で3時間反応させた。こうして得られたポリウレタン樹脂水分散液は、樹脂固形分濃度が35%、粘度が300mPa・s/25℃、数平均分子量は15,000であった。
攪拌機、温度計および窒素ガス導入管を備えた丸底フラスコに、数平均分子量2,000のポリ(1,4−ブチレンアジペート)グリコール(商品名:アデカニューエースF9−30:(株)ADEKA製)505部、数平均分子量2,000のポリプロピレングリコール(商品名:アデカポリエーテルP2000:(株)ADEKA製)505部、ジメチロールブタン酸99部、イソホロンジイソシアネート391部を仕込み、窒素気流下に70℃で6時間反応させ遊離イソシアネート価3.29%のプレポリマーを得た。次いで、イソプロピルアルコール233部、イソホロンジアミン81部、ジ−n−ブチルアミン28部、28%アンモニア水41部および水2705部からなる混合物の存在下に上記ウレタンプレポリマー1,495部を添加し、50℃で3時間反応させた。こうして得られたポリウレタン樹脂水分散液は、樹脂固形分濃度が35%、粘度が400mPa・s/25℃、数平均分子量は15,000であった。
実施例3および比較例3で得られたポリウレタン樹脂水分散液を40℃で一ヶ月保温し、状態の変化を観察した。結果を表2に示す。
○:変化なし
×:沈殿物あり
チタン白(ルチル型)30部、水20部、イソプロピルアルコール10部、製造例3および比較製造例3で得られたポリウレタン樹脂水分散液を40部、それぞれペイントシェイカーで練肉し、さらに水20部、イソプロピルアルコール10部を混合して白色塗料を調製した。
上記白色塗料をABS板上に、乾燥後の膜厚が20μmになるようにスプレー塗布し、室温で放置した後、塗膜のレベリング状態を目視で観察した。
○:塗膜表面が平滑で光沢あり
△:塗膜表面の平滑性に乏しく、光沢が劣る
×:塗膜表面が梨地状で光沢がない
Claims (2)
- 1分子中に1〜8個の水酸基を有するヒドロキシ化合物、ε−カプロラクトンおよびプロピレンオキシドを同時に存在させ、反応させて得られる、一般式(1):R1−(A−OH)x(式中、R1は、1分子中に1〜8個の水酸基を有するヒドロキシ化合物から水酸基を除いた残りの基、Aは、一般式(2):−(OOC−X)−(式中、Xは、分岐構造を有していてもよい炭素数5のアルキレン基を表す。)で表される繰り返し単位および一般式(3):−(O−Y)−(式中、Yは、分岐構造を有していてもよい炭素数3のアルキレン基を表す。)で表される繰り返し単位から構成される構造、xは1〜8の整数を表す。)で表されるアルコール類(a)を含有するアルコール成分(A)、ポリイソシアネート類(B)ならびに必要に応じて鎖伸張剤(C)および/または鎖長停止剤(D)を反応させることにより得られるポリウレタン樹脂を含有することを特徴とする印刷インキ用組成物。
- 前記一般式(1)で表されるアルコール類(a)が、一般式(2)で表される繰り返し単位の繰り返し数mが、1〜500の整数および一般式(3)で表される繰り返し単位の繰り返し数nが1〜1000の整数である請求項1に記載の印刷インキ用組成物。
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