JP2009165910A - 分散剤、及びそれを用いた顔料組成物並びに顔料分散体 - Google Patents
分散剤、及びそれを用いた顔料組成物並びに顔料分散体 Download PDFInfo
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- JP2009165910A JP2009165910A JP2008003812A JP2008003812A JP2009165910A JP 2009165910 A JP2009165910 A JP 2009165910A JP 2008003812 A JP2008003812 A JP 2008003812A JP 2008003812 A JP2008003812 A JP 2008003812A JP 2009165910 A JP2009165910 A JP 2009165910A
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- 239000000049 pigment Substances 0.000 title claims abstract description 140
- 239000002270 dispersing agent Substances 0.000 title claims abstract description 78
- 239000000203 mixture Substances 0.000 title claims abstract description 41
- 239000006185 dispersion Substances 0.000 title claims description 31
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 49
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 34
- 229920000642 polymer Polymers 0.000 claims abstract description 32
- 125000004018 acid anhydride group Chemical group 0.000 claims abstract description 27
- 239000000178 monomer Substances 0.000 claims description 46
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- 125000000217 alkyl group Chemical group 0.000 claims description 20
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
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- 229910052799 carbon Inorganic materials 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
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- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
- 239000003973 paint Substances 0.000 description 5
- 229920002223 polystyrene Polymers 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 229910052801 chlorine Chemical group 0.000 description 4
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
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- 125000000524 functional group Chemical group 0.000 description 4
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- 150000002367 halogens Chemical group 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
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Landscapes
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Abstract
【解決手段】酸無水物基を有する重合体(a)中の酸無水物基1モルに対して、片末端領域に2つの水酸基を有するビニル重合体(b)中の水酸基0.2〜2.0モルを付加反応させてなる分散剤。
【選択図】なし
Description
片末端領域に2つの水酸基を有するビニル重合体(b)中の水酸基0.2〜2.0モルを付加反応させてなる分散剤に関する。
フェニル(メタ)アクリレート、ベンジル(メタ)アクリレート、フェノキシエチル(メタ)アクリレート、フェノキシジエチレングリコール(メタ)アクリレート等の芳香族(メタ)アクリレート類;
(メタ)アクリル酸、イタコン酸、マレイン酸、フマール酸、クロトン酸等のカルボキシル基含有単量体;
グリシジル(メタ)アクリレート、オキセタン(メタ)アクリレート、テトラヒドロフルフリール(メタ)アクリレート等の複素環式(メタ)アクリレート類;
メトキシポリプロピレングリコール(メタ)アクリレート、エトキシポリエチレングリコール(メタ)アクリレート等のアルコキシポリアルキレングリコール(メタ)アクリレート類;
(メタ)アクリルアミド、N,N−ジメチル(メタ)アクリルアミド、N,N−ジエチル(メタ)アクリルアミド、N−イソプロピル(メタ)アクリルアミド、N−ブチル(メタ)アクリルアミド、イソブチル(メタ)アクリルアミド、t−ブチル(メタ)アクリルアミド、及びt−オクチル(メタ)アクリルアミドダイアセトン(メタ)アクリルアミド、アクリロイルモルホリン等の(N置換型)(メタ)アクリルアミド類;
N,N−ジメチルアミノエチル(メタ)アクリレート、N,N−ジエチルアミノエチル (メタ)アクリレート等のアミノ基含有(メタ)アクリレート類;
及び、(メタ)アクリロニトリル等のニトリル類;
片末端メタクリロイル化ポリメチルメタクリレートオリゴマー、片末端メタクリロイル化ポリスチレンオリゴマー、及び片末端メタクリロイル化ポリエチレングリコール等の重合性オリゴマー等があげられる。
エチルビニルエーテル、n−プロピルビニルエーテル、イソプロピルビニルエーテル、n−ブチルビニルエーテル、イソブチルビニルエーテル等のビニルエーテル類;
酢酸ビニル、プロピオン酸ビニル等の脂肪酸ビニル類;
N−メチルマレイミド、N−エチルマレイミド、N−シクロヘキシルマレイミド、N−フェニルマレイミド等のN置換マレイミド類があげられる。
フェニル(メタ)アクリレート、ベンジル(メタ)アクリレート、フェノキシエチル(メタ)アクリレート、フェノキシジエチレングリコール(メタ)アクリレート等の芳香族(メタ)アクリレート類;
(メタ)アクリル酸、イタコン酸、マレイン酸、フマール酸、クロトン酸等のカルボキシル基含有単量体;
2−ヒドロキシエチル(メタ)アクリレート、3−ヒドロキシプロピル(メタ)アクリレート、2−ヒドロキシプロピル(メタ)アクリレート、4−ヒドロキシブチル(メタ)アクリレート、3−ヒドロキシブチル(メタ)アクリレート、2−ヒドロキシブチル(メタ)アクリレート、エチル−α−(ヒドロキシメチル)アクリレート、2−ヒドロキシ−3−フェノキシプロピルアクリレート、1,4−シクロヘキサンジメタノールモノ(メタ)アクリレート等の水酸基含有(メタ)アクリレート類;
グリシジル(メタ)アクリレート、オキセタン(メタ)アクリレート、テトラヒドロフルフリール(メタ)アクリレート等の複素環式(メタ)アクリレート類;
メトキシポリプロピレングリコール(メタ)アクリレート、エトキシポリエチレングリコール(メタ)アクリレート等のアルコキシポリアルキレングリコール(メタ)アクリレート類;
(メタ)アクリルアミド、N,N−ジメチル(メタ)アクリルアミド、N,N−ジエチル(メタ)アクリルアミド、N−イソプロピル(メタ)アクリルアミド、N−ブチル(メタ)アクリルアミド、イソブチル(メタ)アクリルアミド、t−ブチル(メタ)アクリルアミド、及びt−オクチル(メタ)アクリルアミドダイアセトン(メタ)アクリルアミド、アクリロイルモルホリン等の(N置換型)(メタ)アクリルアミド類;
N,N−ジメチルアミノエチル(メタ)アクリレート、N,N−ジエチルアミノエチル(メタ)アクリレート等のアミノ基含有(メタ)アクリレート類;
及び、(メタ)アクリロニトリル等のニトリル類;
片末端メタクリロイル化ポリメチルメタクリレートオリゴマー、片末端メタクリロイル化ポリスチレンオリゴマー、及び片末端メタクリロイル化ポリエチレングリコール等の重合性オリゴマー等があげられる。
エチルビニルエーテル、n−プロピルビニルエーテル、イソプロピルビニルエーテル、n−ブチルビニルエーテル、イソブチルビニルエーテル等のビニルエーテル類;
酢酸ビニル、プロピオン酸ビニル等の脂肪酸ビニル類;
N−メチルマレイミド、N−エチルマレイミド、N−シクロヘキシルマレイミド、N−フェニルマレイミド等のN置換マレイミド類があげられる。
ベンジルアルコール、フェネチルアルコール、p−ヒドロキシフェネチルアルコール等の脂肪芳香族アルコール類;
乳酸、β−乳酸等のカルボン酸含有アルコール類;
グリセロール、3−エチル−3−ヒドロキシメチルオキセタン、フルフリールアルコール、テトラヒドロフルフリールアルコール、グリセリンカーボネート、N−(2−ヒドロキシエチル)マレイミド等の複素環含有アルコール類等が挙げられる。
Xは、−SO2−、−CO−、−CH2NHCOCH2−、−CH2−又は直接結合を表す。
X1、X2は、−SO2−、−CO−、−CH2NHCOCH2−、−CH2−又は直接結合を表す。
一般式(7)−COCl
一般式(8)−CH2NHCOCH2Cl
一般式(9)−CH2Cl
アセトン、メチルエチルケトン、メチル−n−プロピルケトン、メチルイソプロピルケトン、メチル−n−ブチルケトン、メチルイソブチルケトン、メチル−n−アミルケトン、メチルイソアミルケトン、ジエチルケトン、エチル−n−プロピルケトン、エチルイソプロピルケトン、エチル−n−ブチルケトン、エチルイソブチルケトン、ジ−n−プロピルケトン、ジイソブチルケトン、シクロヘキサノン、メチルシクロヘキサノン、イソホロン等のケトン類;
酢酸メチル、酢酸エチル、酢酸−n−プロピル、酢酸イソプロピル、酢酸−n−ブチル、酢酸イソブチル、酢酸ヘキシル、酢酸オクチル、乳酸メチル、乳酸プロピル、乳酸ブチル等のエステル類;
γ−ブチロラクトン、ε−カプロラクトン等のラクトン類;
エチレングリコール、エチレングリコールモノイソプロピルエーテル、エチレングリコールモノブチルエーテル、エチレングリコールモノヘキシルエーテル、ジエチレングリコールモノメチルエーテル、ジエチレングリコールモノエチルエーテル、ジエチレングリコールモノブチルエーテル、エチレングリコールジメチルエーテル、エチレングリコールジエチルエーテル、ジエチレングリコールジメチルエーテル、ジエチレングリコールメチルエチルエーテル、ジエチレングリコールジエチルエーテル、プロピレングリコール、プロピレングリコールモノメチルエーテル、プロピレングリコールモノエチルエーテル、プロピレングリコールモノプロピルエーテル、プロピレングリコールモノブチルエーテル、ジプロピレングリコールモノメチルエーテル、ジプロピレングリコールモノエチルエーテル、ジプロピレングリコールジプロピルエーテル、トリプロピレングリコールモノメチルエーテル、テトラエチレングリコールジメチルエーテル等のグリコール及びグリコールエーテル類;
エチレングリコールモノメチルエーテルアセテート、エチレングリコールモノエチルエーテルアセテート、エチレングリコールモノブチルエーテルアセテート、ジエチレングリコールモノメチルエーテルアセテート、ジエチレングリコールモノエチルエーテルアセテート、ジエチレングリコールモノブチルエーテルアセテート、プロピレングリコールモノメチルエーテルアセテート、プロピレングリコールモノエチルエーテルアセテート、プロピレングリコールモノブチルエーテルアセテート、ジプロピレングリコールモノメチルエーテルアセテート等のグリコールアセテート類;
n−ヘキサン、イソヘキサン、n−ノナン、イソノナン、ドデカン、イソドデカン等の飽和炭化水素類;
1−ヘキセン、1−ヘプテン、1−オクテン等の不飽和炭化水素類;
シクロヘキサン、シクロヘプタン、シクロオクタン、シクロデカン、デカリン等の環状飽和炭化水素類;
シクロヘキセン、シクロヘプテン、シクロオクテン、1,1,3,5,7−シクロオクタテトラエン、シクロドデセン等の環状不飽和炭化水素類;
N−メチル−2−ピロリドン、N−エチル−2−ピロリドン、2−ピロリドン等の(N−アルキル)ピロリドン類;
N−メチル−2−オキサゾリジノン等のN−アルキルオキサゾリジノン類;
ベンゼン、トルエン、キシレン等の芳香族炭化水素類等があげられる。
ガス導入管、温度計、コンデンサー、攪拌機を備えた反応容器に、メチルメタクリレート942部、1−チオグリセロール11部と、メチルエチルケトン(MEK)1429部を仕込み、窒素ガスで置換した。反応容器内を75℃に加熱して、12時間反応した。固形分測定により95%が反応したことを確認後、室温まで冷却して、重量平均分子量4000の、片末端領域に2つの水酸基を有するビニル重合体(中間体1)の固形分40%溶液を得た。
表1に記載した原料と仕込み量を用いた以外は中間体1合成と同様にして合成を行い、片末端領域に2つの水酸基を有するビニル重合体(中間体2〜6)の固形分40%溶液を得た。
BMA:n−ブチルメタクリレート
EA:エチルアクリレート
MAA:メタクリル酸
MEK:メチルエチルケトン
ガス導入管、温度計、コンデンサー、攪拌機を備えた反応容器に、PGMAc(プロピレングリコールモノメチルエーテルアセテート)250部を入れ、容器に窒素ガスを注入しながら80℃に加熱して、同温度でメチルメタクリレート80.0部、2−ヒドロキシエチルメタクリレート20.0部、及び2,2'−アゾビスイソブチロニトリル4.0部の混合物を1時間かけて滴下することにより重合反応を行った。滴下終了後、更に80℃で3時間反応させた後、2,2'−アゾビスイソブチロニトリル1.0部をPGMAc50部に溶解させたものを添加し、更に80℃で1時間反応を続けた。その後、2−メタクリロイルオキシエチルイソシアネート23.8部を添加し、更に80℃で6時間反応を行い、ワニス用樹脂を得た。PGMAcを添加して固形分を20%に調整した。ワニス用樹脂の重量平均分子量は、約24000であった。
ガス導入管、温度計、コンデンサー、攪拌機を備えた反応容器に、SMAベースレジン1000(仕込みモル比がスチレン/無水マレイン酸=1/1から得られる重量平均分子量5500のスチレン−無水マレイン酸共重合体;サートマー社製)47部、固形分40%の中間体1の溶液2382部、触媒として1,8−ジアザビシクロ−[5.4.0]−7−ウンデセン1.0部(1000ppm)と、MEK71部を仕込み、窒素ガスで置換した。反応容器内を75℃に加熱して、16時間反応した。酸価の測定で98%以上の酸無水物がハーフエステル化していることを確認後、反応溶液を冷却して、PGMAcで固形分調整することにより固形分40%の分散剤溶液(D1)を得た。
表2に記載した原料と仕込み量を用いた以外は実施例1と同様にしてそれぞれ合成を行い、固形分40%の分散剤溶液(D2及びD3)を得た。
ガス導入管、温度計、コンデンサー、攪拌機を備えた反応容器に、無水マレイン酸24部と、MEK71部を仕込み、窒素ガスで置換した後、反応容器内を75℃に加熱した。スチレン12部、インデン12部と、2,2’−アゾビスイソブチロニトリル0.75部の混合物を反応容器内に2時間かけて滴下した。更に反応を5時間行い、固形分測定により95%が反応したことを確認した。次に、固形分40%の中間体4の溶液2382部と、触媒として1,8−ジアザビシクロ−[5.4.0]−7−ウンデセン1.0部(1000ppm)を添加し、16時間反応した。酸価の測定で98%以上の酸無水物がハーフエステル化していることを確認後、反応溶液を冷却して、PGMAcで固形分調整することにより固形分40%の分散剤溶液(D4)を得た。
表2に記載した原料と仕込み量を用いた以外は実施例4と同様にしてそれぞれ合成を行い、固形分40%の分散剤溶液(D5及びD6)を得た。
SMA3000:仕込みモル比がスチレン/無水マレイン酸=1/3から得られる重量平均分子量9500のスチレン−無水マレイン酸共重合体(サートマー社製;製品名SMAベースレジン3000)
表3に記載した原料と仕込み量を用いた以外は実施例1と同様にしてそれぞれ合成を行い、固形分40%の分散剤溶液(D7及びD8)溶液を得た。
下記表4に示す割合で、顔料(C.I.Pigment Blue 15:6)、実施例1にて合成した固形分40%の分散剤溶液(D1)、塩基性基を有する顔料誘導体48、及びPGAMcを配合し、0.8mmφガラスビーズ100部を加えスキャンデックスで3時間分散し、銅フタロシアニン顔料組成物を作製した。
下記表4に示す割合で配合し、実施例7と同様にして顔料組成物を得た。
下記表5に示す割合で、顔料(C.I.Pigment Blue 15:6)、実施例1にて合成した固形分40%の分散剤溶液(D1)、塩基性基を有する顔料誘導体48、製造例7で合成したワニス用樹脂、及びPGAMcを配合し、0.8mmφガラスビーズ100部を加えスキャンデックスで3時間分散し、銅フタロシアニン分散体を作製した。
下記表5に示す割合で配合し、実施例13と同様にして顔料分散体を得た。
本発明の顔料組成物及び顔料分散体の性能を評価するために、得られた顔料組成物及び顔料分散体の粘度をB型粘度計(25℃、回転速度100rpm)で測定し、初期粘度、及び経時安定性を評価した。(粘度は低いほど良好。) 初期粘度は分散後1日室温で放置後に測定、経時粘度は1週間40℃に放置後に測定を行った。初期粘度に対する経時粘度の変化率が±10%以内の時は、経時安定性は○、±10%〜±20%の時は△、±20%の範囲外の時は×とした。
青用顔料:ε型銅フタロシアニン顔料(C.I.Pigment Blue 15:6)(BASF製「ヘリオゲンブルーL−6700F」)
青用誘導体:フタロシアニン顔料誘導体(誘導体48)
紫用顔料:ジオキサジンバイオレット顔料(C.I.Pigment Violet 23)(東洋インキ製造社製「リオノゲンバイオレットRL」)
紫用誘導体:ジオキザジン系顔料誘導体(誘導体49)
赤用顔料:ジケトピロロピロール系顔料(C.I.Pigment Red 254)8.33部(チバガイギー社製「イルガフォーレッドB−CF」)、アントラキノン系顔料(C.I.Pigment Red 177)1.33部(チバガイギー社製「クロモフタールレッドA2B」)、アントラキノン系顔料(C.I.Pigment Yellow 199)0.34部(チバガイギー社製「クロモフタールエローGT-AD」)の混合物
赤用誘導体:アントラキノン誘導体(誘導体4)
黄用顔料:イソインドリン系顔料(C.I.Pigment Yellow 139)(BASF社製「パリオトールエローD1819」
黄用誘導体:トリアジン誘導体(誘導体44)
Claims (12)
- 酸無水物基を有する重合体(a)中の酸無水物基1モルに対して、
片末端領域に2つの水酸基を有するビニル重合体(b)中の水酸基0.2〜2.0モルを付加反応させてなる分散剤。 - 酸無水物基を有する重合体(a)が、無水マレイン酸と、無水マレイン酸と共重合可能なエチレン性不飽和単量体(a1)と、をラジカル重合して得られることを特徴とする請求項1記載の分散剤。
- 片末端領域に2つの水酸基を有するビニル重合体(b)が、分子内に2つの水酸基と1つのチオール基とを有する化合物(b1)の存在下に、エチレン性不飽和単量体(b2)をラジカル重合してなることを特徴とする請求項1又は2記載の分散剤。
- エチレン性不飽和単量体(b2)が、メチルメタクリレートを含むことを特徴とする請求項3記載の分散剤。
- エチレン性不飽和単量体(b2)が、更にブチルメタクリレートを含むことを特徴とする請求項4記載の分散剤。
- エチレン性不飽和単量体(b2)の合計100重量%中、メチルメタクリレートとブチルメタクリレートとの合計が20〜100重量%であることを特徴とする請求項4又は5記載の分散剤。
- 片末端領域に2つの水酸基を有するビニル重合体(b)の重量平均分子量が、1,000〜30,000であることを特徴とする請求項1〜7いずれか記載の分散剤。
- 重量平均分子量が、1,500〜100,000であり、かつ、酸価が5〜120mgKOH/gであることを特徴とする請求項1〜8いずれか記載の分散剤。
- 請求項1〜9いずれか記載の分散剤と、顔料とを含有する顔料組成物。
- 更に、塩基性基を有する顔料誘導体、塩基性基を有するアントラキノン誘導体、塩基性基を有するアクリドン誘導体、及び塩基性基を有するトリアジン誘導体からなる群から選ばれる塩基性誘導体の少なくとも一種を含有する請求項10記載の顔料組成物。
- 請求項10又は11記載の顔料組成物とワニスとを含んでなる顔料分散体。
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JP2011032374A (ja) * | 2009-07-31 | 2011-02-17 | Sanyo Shikiso Kk | 微細顔料組成物およびその製造方法 |
JP2011045862A (ja) * | 2009-08-28 | 2011-03-10 | Nippon Shokubai Co Ltd | 高分子分散剤 |
CN114736533A (zh) * | 2022-04-13 | 2022-07-12 | 苏州世名科技股份有限公司 | 表面改性有机颜料及改性方法、应用和包含其的色母粒 |
CN116333531A (zh) * | 2021-12-22 | 2023-06-27 | 东洋油墨Sc控股株式会社 | 着色剂分散体、油墨、油墨组和印刷物 |
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