JP2011515535A - リン酸塩遊離が低減した改質顔料、ならびにそれからの分散体およびインクジェットインク組成物 - Google Patents
リン酸塩遊離が低減した改質顔料、ならびにそれからの分散体およびインクジェットインク組成物 Download PDFInfo
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- JP2011515535A JP2011515535A JP2011500790A JP2011500790A JP2011515535A JP 2011515535 A JP2011515535 A JP 2011515535A JP 2011500790 A JP2011500790 A JP 2011500790A JP 2011500790 A JP2011500790 A JP 2011500790A JP 2011515535 A JP2011515535 A JP 2011515535A
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- modified pigment
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- 230000036961 partial effect Effects 0.000 claims abstract description 34
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- 125000002877 alkyl aryl group Chemical group 0.000 claims description 7
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- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/324—Inkjet printing inks characterised by colouring agents containing carbon black
- C09D11/326—Inkjet printing inks characterised by colouring agents containing carbon black characterised by the pigment dispersant
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/324—Inkjet printing inks characterised by colouring agents containing carbon black
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
- Ink Jet (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
Abstract
Description
次の例は、少なくとも1つの有機基に結合したカーボンブラックを含む改質含量の調製を説明する。例1については、有機基は、式−CO−NH−CH(PO3H2)2またはその塩を有する基を含む。例1については、有機基は、−SO2−NH−CH(PO3H2)2 またはその塩を有する基を含む。
例1
アミノメチレンビスホスホネート(AMBP)が、次の方法の1つを用いて下のスキーム1に示されるように調製された。
リン酸(750g、9.15モル、1.6当量)が、機械的な撹拌機、保護管付コンデンサー、水冷却機(water condenser)、温度計および添加漏斗を備えた反応器に窒素雰囲気下に充填された。これに1,4−ジオキサン(1.5L)、ついでホルムアルデヒド(250g、5.56モル、1当量)が、撹拌しながら添加された。窒素雰囲気が取り除かれ、混合物は60℃で1時間、温められ、ついで20℃に冷却された。三塩化リン(1.5L、17.19モル、3.1当量)が、3時間にわたって混合物に添加され、得られる混合物は60℃で3時間、加熱された。その加熱の間、反応混合物は白色の粘着性の塊に変わり、終わり近くでは撹拌が困難であった。加熱と撹拌が中止され、反応混合物は室温に一夜放置された。デカンテーションにより液相を除去した後、水(2.5L)が加水分解のために反応塊に添加され、ついで加熱されて4時間還流された。反応混合物は、室温に冷却され、ろ過され、メタノール(2.5L)で洗浄され、真空下に乾燥され、白色固体としてAMBP(540g、収率51%)を生成した。この化合物についての1HNMRデータ(D2O/NaOH)は、次のとおりであった:2.56(t、1H,J=16.4Hz)。この化合物についてのLC−MSデータは、次のとおりであった:190[M−1]。
方法B
機械的なオーバーヘッド撹拌機、保護管付水冷却機、温度計および液体添加漏斗を備えた20Lマルチ首丸底フラスコ中で、ホルムアルデヒド(500g、11.11モル)およびリン酸(800g、9.75モル)に、脱イオン水(600mL,33.33モル)が添加された。混合物は氷水浴中で10℃に冷却され、これに三塩化リン0.5L(水への三塩化リンの添加は発熱性)が、20〜25℃未満の温度で3時間にわたり添加され、ついでさらに30分間にわたって、三塩化リン0.5Lがさらに添加された。すべての水が消費されたとき、温度は10℃未満に低下し、これに三塩化リン2.5Lが15分間にわたって添加された(三塩化リン添加は合計3.5L,40モルであった。)。泡立ちを調節するために、撹拌機はフラスコ内で上げられ、もっと高速で撹拌された。ついで、反応混合物は2〜2.5時間で、60℃に温められ、反応塊が固化し、もはや撹拌できなくなるまで(60℃に達した後、約1時間)、その温度で保持された。加熱および撹拌は中止され、反応混合物は40℃へゆっくり冷却するために、一夜放置された。残りの過剰三塩化リンは、デカンテーションにより除去され、脱塩水1Lが窒素雰囲気下に4時間にわたって反応混合物に添加された(この急冷(quenching)プロセスの熱進化(heat evolution)は、激しく反応し得る過剰水の存在を避けるために水を少しずつ添加することにより調節された)。反応混合物は、約0.5時間撹拌され、ついでさらに脱塩水4Lが添加され、加熱されて6時間還流された。得られる混合物は、35℃に一夜冷却され、ついでろ過され、脱イオン水2Lで、さらにアセトン2Lで洗浄され、減圧下で一夜乾燥され、白色固体としてAMBP(830g、収率39%)を生成した。この化合物についての1HNMRデータ(400MHz、D2O/NaOH)は、次のとおりであった:2.56(t、1H,J=16.4Hz)。この化合物についてのLC−MSデータは、次のとおりであった:190[M−1]。
方法A
カーボンブラック20g、化合物3の20ミリモルおよびDI水200mLが、室温でSilversonミキサー(6000rpm)で混合された。得られるスラリーのpHが4より大きかったら、硝酸20ミリモルも添加された。30分後に、少量の水中の亜硝酸ナトリウム(20ミリモル)が混合物にゆっくりと添加された。温度は撹拌により60℃に達し、1時間継続された。本発明の改質顔料が生成された。pHはNaOH溶液により10に調整された。30分後に、得られる改質顔料分散体は、少なくとも1つのジェミナルビスホスホン酸基またはその塩と結合した顔料を含み、DI水20容量を用いてSpectrum膜で透析ろ過され(diafiltered)、約12%固形分に濃縮され、所望の粒径を得るために30分間、超音波処理された(sonicated)。
方法B
ProcessAll 4HV ミキサー(4L)に、乾燥カーボンブラック500g、DI水1L,および化合物3が充填された。ついで、得られる混合物は、10分間、300rpmで強く混合する間、60℃に加熱された。これに20%亜硝酸ナトリウム水性溶液(化合物3の量に基づき1モル当量)が15分間にわたって添加された。加熱および混合は合計3時間継続された。ミキサーの内容物は、追加DI水750mLで希釈されて除去され、ついで得られる改質顔料の分散体は、DI水を用いて透析ろ過により精製された。透析ろ過の終わり(浸漬物導電率(permeate conductivity)<200マイクロシーメンス)で、分散体中の改質顔料の濃度は、15%に調整され、ついでCarr Continuous Centrifuge(PilotFuge)内で遠心分離された。
化合物4は、4−ニトロベンゼンスルフォニルクロライドが4−ニトロベンゾイルクロライドの代わりに使用されたことを除けば、例1に記載される手順を用いてAMBPから調製された。反応は下のスキーム4に示される。
改質カーボンブラック顔料の分散体は、処理レベルが0.5ミリモル/gであったことを除けば、米国特許出願公開第2007/0100024号の例12に記載される手順を用いて調製された。
例4
本発明の改質顔料の分散体は、使用された顔料がPigment Red 122(PR122)またはSmall Particle Pigment Red 122(PR122sp)(いずれもSun Chemicalより入手し得る)であったことを除けば、例1に記載される方法Aを用いて調製された。具体的な顔料および処理レベルは得られるナトリウム含量とともに、下の表4に示される。
改質顔料の比較分散体が調製され、それらは2つのホスホン酸基またはその塩と結合した顔料を含んでいた。その改質顔料分散体は、米国特許出願公開第2007/0100024号の例12に記載される手順を用いて調製された。特に、比較例1の改質顔料分散体は、この公開の例88に記載されるように調製された。ただし、Black Pearls(登録商標)880カーボンブラック(上に示されるBP880)が顔料として使用され、そして処理レベルは0.6ミリモル/g(比較例1Aについて)、0.7ミリモル/g(比較例1Bについて)、および1.0ミリモル/g(比較例1Cについて)であった。比較例2の改質顔料分散体は、Pigment Red 122(上に示されるPR122)が顔料として使用されたことを除けば、この公開の例72Bに記載されるように調製された。比較例3の改質顔料分散体は、この公開の例7aに記載されるように調製され、その処理レベルは1.7ミリモル/gであった。比較例4の改質顔料分散体は、この公開の例10に記載されるように調製され、その処理レベルは0.5ミリモル/gであった。最後に、比較例5の改質顔料分散体は、この公開の例11および13に記載されるように調製され、その処理レベルは0.5ミリモル/gであった。
例5〜11および比較例6〜8
次の例は、インクジェットインク組成物の調製および印刷性能を記載する。例5〜11は本発明のインクジェットインク組成物であるが、比較例6〜8は比較のインクジェットインク組成物を説明する。各組成物で使用された具体的な顔料は、下の表5に示される。
例12
本発明の各改質顔料の15%水性分散体の熱安定性も評価された。本発明の分散体は室温および70℃のいずれでも安定(4〜6週間以上)であり、粒径および15%固体での粘度の変化が10%未満であることがわかった。
Claims (41)
- 液体ビヒクル、および少なくとも1つの有機基に結合した顔料からなる少なくとも1つの改質顔料からなるインクジェットインク組成物であり、その有機基は少なくとも1つのジェミナルビスホスホン酸基、その部分エステル、またはその塩からなり、その改質顔料は、70℃で1週間後に、1%以下のリン酸塩遊離値を有するインクジェットインク組成物。
- 有機基は、式-CR(PO3H2)2を持つ、少なくとも1つの基、その部分エステル、またはその塩からなり、ここでRはHまたはC1〜C6のアルキル基である、請求項1に記載のインクジェットインク組成物。
- 有機基は、式-CO-Q-CH(PO3H2)2もしくは式-SO2-Q-CH(PO3H2)2を持つ、少なくとも1つの基、その部分エステル、またはその塩からなり、ここでQはO、S、またはNR’であり、R’はH、C1〜C18のアルキル基、C1〜C18のアシル基、アラルキル基、アルカリール基またはアリール基である、請求項1に記載のインクジェットインク組成物。
- QはNHである請求項3に記載のインクジェットインク組成物。
- 有機基は、式−X−CO−Q−CH(PO3H2)2もしくは−X−SO2−Q−CH(PO3H2)2 を有する基、その部分エステル、またはその塩を有し、ここでXは顔料に結合され、アリーレン、ヘテロアリーレン、アルキレン、アルカリーレン、またはアラルキレン基である請求項1に記載のインクジェットインク組成物。
- Xがアリーレン基である請求項5に記載のインクジェットインク組成物。
- QはNHである請求項5に記載のインクジェットインク組成物。
- 有機基は、式−C6H4−CONHCH(PO3H2)2基、−C6H4−SO2NHCH(PO3H2)2 基、その部分エステル、またはその塩である請求項1に記載のインクジェットインク組成物。
- 顔料が、ブルー顔料、ブラック顔料、ブラウン顔料、シアン顔料、グリーン顔料、ホワイト顔料、バイオレット顔料、マゼンタ顔料、レッド顔料、オレンジ顔料、イエロー顔料またはそれらの混合物である請求項1に記載のインクジェットインク組成物。
- 顔料がカーボンブラックである請求項1に記載のインクジェットインク組成物。
- 改質顔料が、70℃で2週間後に、2%以下のリン酸塩遊離値を有する請求項1に記載のインクジェットインク組成物。
- 改質顔料が、70℃で3週間後に、3%以下のリン酸塩遊離値を有する請求項1に記載のインクジェットインク組成物。
- 改質顔料が、70℃で4週間後に、4%以下のリン酸塩遊離値を有する請求項1に記載のインクジェットインク組成物。
- 液体ビヒクルが水性ビヒクルである請求項1に記載のインクジェットインク組成物。
- 液体ビヒクル、および少なくとも1つの有機基に結合した顔料からなる少なくとも1つの改質顔料からなるインクジェットインク組成物であり、その有機基は式-CO-Q-CH(PO3H2)2もしくは式-SO2-Q-CH(PO3H2)2を持つ、少なくとも1つの基、その部分エステル、またはその塩からなり、ここでQはO、S、またはNR’であり、R’はH、C1〜C18のアルキル基、C1〜C18のアシル基、アラルキル基、アルカリール基またはアリール基である、インクジェットインク組成物。
- QはNHである請求項15に記載のインクジェットインク組成物。
- 有機基は、式−X−CO−Q−CH(PO3H2)2もしくは−X−SO2−Q−CH(PO3H2)2 、その部分エステル、またはその塩を有し、ここでXは顔料に結合され、アリーレン、ヘテロアリーレン、アルキレン、アルカリーレン、またはアラルキレン基である請求項15に記載のインクジェットインク組成物。
- Xがアリーレン基である請求項17に記載のインクジェットインク組成物。
- QはNHである請求項17に記載のインクジェットインク組成物。
- 有機基は、式−C6H4−CONHCH(PO3H2)2基、−C6H4−SO2NHCH(PO3H2)2 基、その部分エステル、またはその塩である請求項15に記載のインクジェットインク組成物。
- 液体ビヒクルが水性ビヒクルである請求項15に記載のインクジェットインク組成物。
- 少なくとも1つの有機基に結合した顔料からなる改質顔料であり、その有機基は式-CO-Q-CH(PO3H2)2もしくは式-SO2-Q-CH(PO3H2)2を持つ、少なくとも1つの基、その部分エステル、またはその塩からなり、ここでQはO、S、またはNR’であり、R’はH、C1〜C18のアルキル基、C1〜C18のアシル基、アラルキル基、アルカリール基またはアリール基である、改質顔料。
- QはNHである請求項22に記載の改質顔料。
- 有機基は、式−X−CO−Q−CH(PO3H2)2もしくは−X−SO2−Q−CH(PO3H2)2 、その部分エステル、またはその塩を有し、ここでXは顔料に結合され、アリーレン、ヘテロアリーレン、アルキレン、アルカリーレン、またはアラルキレン基である請求項22に記載の改質顔料。
- Xがアリーレン基である請求項24に記載の改質顔料。
- QはNHである請求項24に記載の改質顔料。
- 有機基は、式−C6H4−CONHCH(PO3H2)2基、−C6H4−SO2NHCH(PO3H2)2 基、その部分エステル、またはその塩である請求項22に記載の改質顔料。
- 顔料が、ブルー顔料、ブラック顔料、ブラウン顔料、シアン顔料、グリーン顔料、ホワイト顔料、バイオレット顔料、マゼンタ顔料、レッド顔料、オレンジ顔料、イエロー顔料またはそれらの混合物である請求項22に記載の改質顔料。
- 顔料がカーボンブラックである請求項22に記載の改質顔料。
- 改質顔料が液体ビヒクル中の分散体の形態である請求項22に記載の改質顔料。
- 液体ビヒクルが水性ビヒクルである請求項30に記載の改質顔料。
- 改質顔料が、70℃で1週間後に、1%以下のリン酸塩遊離値を有する請求項30に記載の改質顔料。
- 改質顔料が、70℃で2週間後に、2%以下のリン酸塩遊離値を有する請求項30に記載の改質顔料。
- 改質顔料が、70℃で3週間後に、3%以下のリン酸塩遊離値を有する請求項30に記載の改質顔料。
- 改質顔料が、70℃で4週間後に、4%以下のリン酸塩遊離値を有する請求項30に記載の改質顔料。
- 少なくとも1つの有機基に結合した顔料からなる改質顔料であり、その有機基は少なくとも1つのジェミナルビスホスホン酸基、その部分エステル、またはその塩からなり、その改質顔料は、液体ビヒクル中の分散体の形態であり、70℃で1週間後に、1%以下のリン酸塩遊離値を有する改質顔料。
- 液体ビヒクルが水性ビヒクルである請求項36に記載の改質顔料。
- 改質顔料が、70℃で2週間後に、2%以下のリン酸塩遊離値を有する請求項36に記載の改質顔料。
- 改質顔料が、70℃で3週間後に、3%以下のリン酸塩遊離値を有する請求項36に記載の改質顔料。
- 改質顔料が、70℃で4週間後に、4%以下のリン酸塩遊離値を有する請求項36に記載の改質顔料。
- 有機基は、式-CR(PO3H2)2を持つ、少なくとも1つの基、その部分エステル、またはその塩からなり、ここでRはHまたはC1〜C6のアルキル基である、請求項36に記載の改質顔料。
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US6970008P | 2008-03-17 | 2008-03-17 | |
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PCT/US2009/001604 WO2009117071A1 (en) | 2008-03-17 | 2009-03-13 | Modified pigments having reduced phosphate release, and dispersions and inkjet ink compositions therefrom |
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JP2014109200A Active JP5902752B2 (ja) | 2008-03-17 | 2014-05-27 | リン酸塩遊離が低減した改質顔料、ならびにそれからの分散体およびインクジェットインク組成物 |
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Also Published As
Publication number | Publication date |
---|---|
CN101970586A (zh) | 2011-02-09 |
WO2009117071A1 (en) | 2009-09-24 |
US20090229489A1 (en) | 2009-09-17 |
CN101970586B (zh) | 2014-08-20 |
JP5902752B2 (ja) | 2016-04-13 |
JP2014221897A (ja) | 2014-11-27 |
EP2268747A1 (en) | 2011-01-05 |
JP2016053164A (ja) | 2016-04-14 |
BRPI0908448A2 (pt) | 2019-09-24 |
US7819962B2 (en) | 2010-10-26 |
EP2268747B1 (en) | 2017-08-30 |
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