JP5325704B2 - ビニルアセタール系重合体からなるインキ用、塗料用またはセラミック成形用バインダー - Google Patents
ビニルアセタール系重合体からなるインキ用、塗料用またはセラミック成形用バインダー Download PDFInfo
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- JP5325704B2 JP5325704B2 JP2009188772A JP2009188772A JP5325704B2 JP 5325704 B2 JP5325704 B2 JP 5325704B2 JP 2009188772 A JP2009188772 A JP 2009188772A JP 2009188772 A JP2009188772 A JP 2009188772A JP 5325704 B2 JP5325704 B2 JP 5325704B2
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- acetal polymer
- vinyl acetal
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Description
その中でも、ビニルアルコール系重合体とホルムアルデヒドとから製造されるビニルホルマール系重合体、ビニルアルコール系重合体とアセトアルデヒドとから製造されるビニルアセタール系重合体、およびビニルアルコール系重合体とブチルアルデヒドとから製造されるビニルブチラール系重合体は、商業的に重要な位置を占めている。
特に近年、印刷機は高速で運転されることが多いことから、印刷機の高速運転を実現するために、印刷インキが所望の粘度において高い顔料含有率を有しており、かつ印刷により成形される塗膜の厚さが薄い場合でも、色の強度が大きいことが必要であるとされている。一般的に、印刷インキにおいて顔料含有率を高くするためには、その溶液粘度を低くすることが重要である。印刷インキの溶液粘度を低くするためには、低重合度のビニルアセタール系重合体を使用することが考えられるが、完全けん化ビニルアルコール系重合体をアセタール化することにより製造される低重合度ビニルアセタール系重合体を用いる場合には、ビニルアセタール系重合体の水溶液がゲル化しやすい、顔料含有率を高くすることができないなどの問題点があった。
さらに本発明の目的は、セラミックグリーンシートの薄膜化に対応して、粒径が小さいセラミック粉体を原料に用いた場合でも、均質でシート強度の大きいセラミックグリーンシートの製造を可能にするセラミック成形用バインダーに適したビニルアセタール系重合体を提供することにある。
すなわち、本発明は、分子内にN−ビニル−2−カプロラクタムを含有するビニルアセタール系重合体からなるインキ用、塗料用またはセラミック成形用バインダーである。
また、本発明のビニルアセタール系重合体は、セラミック成形用バインダーとして用いることにより、表面の状態が均質でシート強度が高く、薄膜化への対応が可能なセラミックグリーンシートの製造を可能にする。薄膜化されたセラミックグリーンシートは、特に近年望まれている電気・電子部品の小型化・高性能化に有用であることから、小型で大容量のセラミック積層コンデンサーやICチップ用のセラミック電子回路基板などに好適に使用することができる。
本発明のビニルアセタール系重合体は、N−ビニルアミド系単量体単位を含有することが必須であり、その含有量は0.1〜20モル%が好ましく、0.5〜15モル%がより好ましく、1〜12モル%がさらに好ましい。N−ビニルアミド系単量体単位の含有量が0.1モル%より小さい場合には、本発明の課題である高固形分比(高顔料含有率)での低粘度化効果が小さく、N−ビニルアミド系単量体単位の含有量が20モル%を超える場合には、ビニルアセタール重合体の製造が困難になる場合がある。
また、必要に応じて、カルボン酸を含有するアルデヒド化合物を併用してもよい。
けん化反応に用いられる触媒としては、水酸化カリウム、水酸化ナトリウムなどのアルカリ触媒、または硫酸、塩酸、p−トルエンスルホン酸などの酸触媒が挙げられる。
P=([η]×1000/8.29)(1/0.62)
なお、その際に分散剤として、カルボン酸基、マレイン酸基、スルホン酸基、リン酸基等を分子内に有するアニオン系分散剤を併用してもよく、とくに金属イオンを含有しないアニオン系分散剤の使用が好ましい。
PVAの分析は、特に断らない限りJIS−K6726に記載の方法にしたがって行った。PVAに含まれるN−ビニルアミド単量体単位、ビニルエステル系単量体単位の含有量は、DMSO−d6に溶解したサンプルを500MHzのプロトンNMR測定装置(JEOL GX−500)を用いて求めた。
ビニルアセタール系重合体のアセタール化度は、DMSO−d6に溶解したサンプルを500MHzのプロトンNMR測定装置(JEOL GX−500)を用いて求めた。
(1)PVA−1
撹拌機、還流冷却管、窒素導入管、コモノマー逐次添加用ライン、および温度計を取り付けた200Lの反応器に、酢酸ビニル単量体16000g、メタノール64000g、N−ビニルアセトアミド183.6gを仕込み、窒素ガスを30分間バブリングして脱気した。反応器の昇温を開始し、内温が60℃となったところで、2,2’−アゾビス(イソブチロニトリル)60gを添加し重合を開始した。重合開始後、コモノマー添加ラインからN−ビニルアセトアミドの10%メタノール溶液を880mL/hrの添加速度で添加した。さらに重合開始から30分おきに重合液を5mL抜き取り、重合液の固形分を測定して酢酸ビニルの重合率を算出し、残存する酢酸ビニル単量体とN−ビニルアセトアミドのモル比率が一定になるようにN−ビニルアセトアミドの10%メタノール溶液の添加速度を調整しながら重合を行った。重合開始から5時間後に冷却して重合を停止した。このときの固形分濃度は14%であり、N−ビニルアセトアミドの10%メタノール溶液の総添加量は2800mLであった。次いでメタノールを逐次的に添加しながら蒸留を行って未反応の酢酸ビニル単量体を除去し、ポリ酢酸ビニル共重合体のメタノール溶液(濃度50%)を得た。
次に、メタノールを加えて濃度を30%に調整したポリ酢酸ビニル共重合体のメタノール溶液6660gに、40℃の条件下で、水酸化ナトリウムの濃度10%メタノール溶液278g(水酸化ナトリウム/ポリ酢酸ビニル共重合体中の酢酸ビニル単位のモル比が0.03)を添加してけん化を行った。析出したゲル状生成物を粉砕し、水酸化ナトリウムの添加から1時間後に酢酸メチル30000gを添加し、70℃の湯浴中で1時間加熱することにより未反応の水酸化ナトリウムを中和した。液きりした後、メタノール30000gを添加し70℃の湯浴中で、1時間加熱して洗浄した。この洗浄操作を2回繰り返し、65℃で12時間加熱乾燥することにより目的とするPVAを得た。プロトンNMR測定から求めたN−ビニルアセトアミド単量体単位、ビニルエステル系単量体単位の含有量はそれぞれ3.1モル%、2.8モル%であり、粘度平均重合度を定法のJIS K6726に準じて測定したところ230であった。
N−ビニルアミド単量体の種類を表1に示すように変化させ、さらにPVA中のN−ビニルアミド単量体単位の含有量、ビニルエステル系単量体単位の含有量、重合度が表1に示す値となるように重合条件およびけん化条件を変更した以外は、PVA−1と同様にして各種のPVA(PVA−2〜23)を得た。また、N−ビニルアミド単量体の代わりに1−メチルビニルアセテートを用い、さらにけん化して得られるPVA中の1−メチルビニルアルコール単位の含有量、ビニルエステル系単量体単位の含有量、重合度が表1に示す値となるように重合条件およびけん化条件を変更した以外は、PVA−1と同様にしてPVA(PVA−24)を得た。
(ビニルアセタール系重合体の合成)
PVA−1 450gを水5550ml中に投入し、95℃まで昇温して2時間撹拌することによりPVA−1を溶解させた。得られた溶液を35℃まで徐々に冷却し、ブチルアルデヒド265.5gを添加し、分散させた後、さらに0℃まで冷却した。0℃に到達後直ちに20%濃度塩酸溶液210mlを30分かけて滴下した。滴下が終了して31分後に白色粉末が析出し始め、さらに29分が経過した後に20%濃度塩酸溶液474mlを30分かけて滴下した。その後、反応溶液を2時間かけて27℃にまで加温し、この温度をさらに2時間維持した。析出した粒状物を濾別して水で念入りに洗浄し、40℃、減圧下で乾燥した。得られたビニルアセタール系重合体(VAP−1)の分析値を表2に示す。
得られたVAP−1を用いて、固形分濃度が15および25重量%のエタノール溶液を調製し、これら溶液の流出時間をDIN4mmカップ(DIN53211/23℃)で測定した。その結果を表3に示す。
(印刷インクの調整)
VAP−1 43.2gを室温で244.8gのエタノールに溶解し、顔料(クラリアント社製「Hostaperm Blue
B 2G」)72gを添加後、Getzmann Dispermat分散機(モデルCA 40−C)を用いて、ガラスビーズ(直径2mm)600gと共に回転数5000rpmで30分かけて分散させた。得られた分散液中のガラスビーズをろ過により取り除くことにより、顔料濃縮液を得た。さらにこの顔料濃縮液80gをVAP−1の15重量%エタノール溶液により、DIN4mmカップ(DIN53211/23℃)での流出時間が25秒となるまで希釈することにより印刷インクを得た。得られた印刷インクの組成および顔料:バインダー(VAP−1)の含有量比を表4に示す。
使用するPVAの種類およびアルデヒドの種類を表2に示すように変更し、さらにアセタール化度が表2に示す値となるように添加するアルデヒドの種類および量を変更した以外は参考例1と同様にしてビニルアセタール系重合体を合成し、15重量%および25重量%のエタノール溶液の流出時間を評価した。その結果を表3に示す。また参考例1と同様にDIN4mmカップ(DIN53211/23℃)での流出時間が25秒となる印刷インクを調製した結果を表4に示す。
使用するPVAの種類およびアルデヒドの種類を表2に示すように変更し、さらにアセタール化度が表2に示す値となるように添加するアルデヒドの種類および量を変更した以外は参考例1と同様にしてビニルアセタール系重合体を合成し、15重量%および25重量%のエタノール溶液の流出時間を評価した。その結果を表3に示す。また参考例1と同様にDIN4mmカップ(DIN53211/23℃)での流出時間が25秒となる印刷インクを調製した結果を表4に示す。
(ビニルアセタール系重合体の合成)
PVA−5 500gを水6500ml中に投入し、95℃まで昇温して2時間撹拌することによりPVA−5を溶解させた。得られた溶液を30℃まで冷却し、ブチルアルデヒド286gを添加して分散させ、さらに0℃まで冷却した。0℃に到達後直ちに20%濃度塩酸溶液1000mlを30分かけて添加し、反応を開始した。塩酸の添加が終了後、その反応溶液を3時間で30℃にまで加温し、そしてこの温度をさらに2時間維持した。析出した粒状物を濾別して水で念入りに洗浄し、中和/アルカリ性化を行うために、10%水酸化ナトリウム溶液32mlを得られた生成物懸濁液に添加し、これを再び穏やかに加温した。さらに、水で洗浄することによって過剰のアルカリを除去した後、40℃、減圧下で乾燥した。得られたビニルアセタール系重合体(VAP−21)の分析値を表5に示す。
(セラミックグリーンシートの作成)
セラミック粉体として平均粒径0.2μmのチタン酸バリウム粉体100部、ビニルアセタール系重合体(VAP−21)10部、可塑剤としてジオクチルフタレート3部、および溶媒としてトルエン60部、イソプロパノール60部をジルコニア製ボール(直径2mm)500部と共に、16時間ボールミルにより混合・解砕した後、減圧下で脱泡処理してセラミックスラリーを調製した。このセラミックスラリーをドクターブレード法により、離型用のポリエチレンテレフタレートフィルム(PETフィルム)上に塗布し、105℃で5分間乾燥後、PETフィルムから離型することで厚み5μmのセラミックグリーンシートを得た。
(セラミックグリーンシート表面の観察)
光学顕微鏡を用いて、セラミックグリーンシートの表面を観察し、下記の基準で判定した。結果を表5に示す。
A:ボイドや凝集粒子による凹凸がなく均質である。
B:ボイドはないものの、凝集粒子による凹凸が認められる。
C:ボイドと、凝集粒子による凹凸が共に認められる。
(セラミックグリーンシートの強度)
セラミックグリーンシートを40mm×100mmに打ち抜き、島津製オートグラフDCS−100にてグリーンシートのタフネスを測定した(チャック間隔:30mm、引張速度:10mm/min.、測定温度20℃)。なお、1つのサンプルについて5回測定を行った平均値をタフネス値とし、比較例7において得られたタフネス値を1.0としたときの比率(倍)を求めた。結果を表5に示す。
使用するPVAの種類およびアルデヒドの種類を表5に示すように変更し、さらにアセタール化度が表5に示す値となるように添加するアルデヒド量を変更した以外は参考例9と同様にしてビニルアセタール系重合体を合成し、参考例9と同様にしてセラミックグリーンシートを作成してその表面を観察し、さらにシートの強度を求めた。その結果を表5に示す。
使用するPVAの種類およびアルデヒドの種類を表5に示すように変更し、さらにアセタール化度が表5に示す値となるようにアセタール化条件を変更したこと以外は参考例9と同様にしてビニルアセタール系重合体を合成し、参考例9と同様にしてセラミックグリーンシートを作成してその表面を観察し、さらにシートの強度を求めた。その結果を表5に示す。
Claims (5)
- 分子内にN−ビニル−2−カプロラクタム単位を含有するビニルアセタール系重合体からなることを特徴とするインキ用、塗料用またはセラミック成形用バインダー。
- 前記ビニルアセタール系重合体が、ビニルアセタール単量体単位をアセタール化された2つのビニルアルコール単量体単位と数えた場合、ビニルエステル系単量体単位を0.01〜20モル%含有し、N−ビニル−2−カプロラクタム単位の含有量が0.1〜20モル%、アセタール化度45〜80モル%であることを特徴とする請求項1記載のバインダー。
- 前記ビニルアセタール系重合体が、分子内にN−ビニル−2−カプロラクタム単位を0.1〜20モル%、ビニルエステル系単量体単位を0.01〜20モル%含有するビニルアルコール系重合体をアセタール化して得られるものである、請求項1または2記載のバインダー。
- 請求項1〜3のいずれか記載のバインダーを1〜25重量%含有するインキまたは塗料。
- 請求項1〜3のいずれか記載のバインダーを用いてなるセラミックグリーンシート。
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2004
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- 2004-01-17 DE DE200460025758 patent/DE602004025758D1/de not_active Expired - Lifetime
- 2004-01-17 DE DE200460029298 patent/DE602004029298D1/de not_active Expired - Lifetime
- 2004-01-17 EP EP20090166354 patent/EP2128176B1/en not_active Expired - Lifetime
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- 2004-01-17 AT AT09166354T patent/ATE482238T1/de not_active IP Right Cessation
- 2004-01-21 JP JP2004012933A patent/JP2004244631A/ja active Pending
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EP2128176A1 (en) | 2009-12-02 |
JP2009270122A (ja) | 2009-11-19 |
EP2128176B1 (en) | 2010-09-22 |
ATE482238T1 (de) | 2010-10-15 |
ATE459658T1 (de) | 2010-03-15 |
JP2004244631A (ja) | 2004-09-02 |
JP5325705B2 (ja) | 2013-10-23 |
US20040152835A1 (en) | 2004-08-05 |
US6984692B2 (en) | 2006-01-10 |
EP1447416A1 (en) | 2004-08-18 |
DE602004029298D1 (de) | 2010-11-04 |
EP1447416B1 (en) | 2010-03-03 |
DE602004025758D1 (de) | 2010-04-15 |
JP2010001488A (ja) | 2010-01-07 |
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