JP2006508210A - β−キナクリドン色素類の製造 - Google Patents
β−キナクリドン色素類の製造 Download PDFInfo
- Publication number
- JP2006508210A JP2006508210A JP2004554536A JP2004554536A JP2006508210A JP 2006508210 A JP2006508210 A JP 2006508210A JP 2004554536 A JP2004554536 A JP 2004554536A JP 2004554536 A JP2004554536 A JP 2004554536A JP 2006508210 A JP2006508210 A JP 2006508210A
- Authority
- JP
- Japan
- Prior art keywords
- dihydroquinacridone
- quinacridone
- weight
- salt
- hydrogen peroxide
- 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.)
- Granted
Links
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- 238000004519 manufacturing process Methods 0.000 title description 7
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- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 52
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 claims abstract description 47
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- KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical class [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 claims description 3
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- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 claims 1
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- 229920002223 polystyrene Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920001291 polyvinyl halide Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000001054 red pigment Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- SDKPSXWGRWWLKR-UHFFFAOYSA-M sodium;9,10-dioxoanthracene-1-sulfonate Chemical compound [Na+].O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)[O-] SDKPSXWGRWWLKR-UHFFFAOYSA-M 0.000 description 1
- YWPOLRBWRRKLMW-UHFFFAOYSA-M sodium;naphthalene-2-sulfonate Chemical compound [Na+].C1=CC=CC2=CC(S(=O)(=O)[O-])=CC=C21 YWPOLRBWRRKLMW-UHFFFAOYSA-M 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Chemical class 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B48/00—Quinacridones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Compounds Of Unknown Constitution (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
さな粒子状のキナクリドンの存在は、本発明の直接的な色素バイオレットβ−キナクリドン色素の生成に付加的に有益な効果作用を有し得る。
ミルベース処方
30.9gのアクリル樹脂、トルエン中の45%のアクリル樹脂からなる16.4gのAB分散剤および42.8g(American ChemicalからのSolvesso(登録商標)100)を1ピントジャーに充填する。実施例6に記載の、30.0gのβ−キナクリドンおよび980gの4mm直径の鋼鉄製ダイアゴナル棒を加える。ジャーを、Skandex(登録商標)振とう機で5時間振とうする。ミルベースは、色素/結合剤の比が0.5である25.0%の色素を含む。
48.9gの上記ミルベース、メラミン樹脂触媒を含む、71.7gの透明な47.8%の固体の色素化されていない樹脂溶媒溶液、非水性分散樹脂およびUV吸収剤、および29.4gの透明な色素化されていない58%固体非色素化ポリエステルウレタン樹脂溶媒溶液を混合し、76部のキシレン、21部のブタノールおよび3部のメタノールを含む溶媒混合物で希釈し、#2Fisher Cupにより測定される、20〜22秒の噴霧粘度にする。樹脂/色素分散液は、ベースコートとして、1.5分間の間隔で、パネルに2回噴霧する。2分後、クリヤコート樹脂を、2回、1.5分間間隔で、ベースコートに噴霧する。その後、噴霧したパネルを、10分間フラッシュキャビネット中で空気でフラッシュし、その後、129℃で30分間オーブン中で「焼き」、バイオレット色のパネルを得る。コートされるパネルは優れた耐気候性を有する。
Claims (11)
- 6,13−ジヒドロキナクリドン塩が、アルカリ金属塩、好ましくは、二ナトリウムもしくは二カリウム塩またはその混合物である、請求項1のプロセス。
- 0.2μmより小さな平均粒子サイズを有する粒子状のβ−結晶相キナクリドンを酸化前または酸化中に加える、請求項1または2のプロセス。
- 粒子β−キナクリドンが、6,13−ジヒドロキナクリドンに基づいて、0.1〜10重量%の濃度で存在し、好ましくは、硫酸からの沈降により、最も好ましくは、ナフタレンスルホン酸ホルムアルデヒドポリマーの存在下で、製造される、請求項3のプロセス。
- 酸化ステップが、6,13−ジヒドロキナクリドン塩、触媒、ポリビニルピロリドン、塩基、液相、および場合により粒子β−キナクリドンおよび/または粒子成長阻害剤から本質的になるスラリーを、過酸化水素の水溶液と組合せることにより行われる、請求項1〜4のいずれかのプロセス。
- 液相が、100重量部の6,13−ジヒドロキナクリドン当たり、20〜750、好ましくは、40〜600重量部の水および50〜750重量部、好ましくは、100〜600重量部のC1〜C3アルコールから本質的になり、好ましいC1〜C3アルコールがメタノールである、請求項5のプロセス。
- 過酸化水素の水溶液を、30℃またはそれ以上の温度で、好ましくは、50℃から還流温度で、5分間から6時間の時間かけてスラリーに加え、反応媒体を、その後、30℃またはそれ以上の温度で、好ましくは、50℃から還流温度で、5分間から4時間、好ましくは、5分間から2時間攪拌しながら維持して、酸化を完了させる、請求項5または6のプロセス。
- 6,13−ジヒドロキナクリドン塩が、6,13−ジヒドロキナクリドンを、1モルの6,13−ジヒドロキナクリドン当たり、1〜8モル、好ましくは、2.2〜7モルの塩基で処理することにより得られる、請求項1〜7のいずれかのプロセス。
- 触媒が、キノンの6,13−ジヒドロキナクリドン重量の0.005〜0.15倍、好ましくは、アントラキノン、アントラキノンモノスルホン酸、アントラキノンジスルホン酸またはその塩、最も好ましくは、アントラキノン−2−スルホン酸、アントラキノン−2,7−ジスルホン酸またはそのナトリウムもしくはカリウム塩である、請求項1〜8のいずれかのプロセス。
- 過酸化水素水溶液中の過酸化水素の濃度が、1〜50重量%、好ましくは、5〜30重量%である、請求項1〜9のいずれかのプロセス。
- 酸化ステップを、6,13−ジヒドロキナクリドンに基づいて、0.05〜10重量%の粒子成長阻害剤、好ましくは、フタルイミドメチル−、イミダゾリルメチル−、ピラゾリルメチル−キナクリドン、またはキナクリドンモノスルホン酸またはその塩の存在下で行なう、請求項1〜10のいずれかのプロセス。
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US42978002P | 2002-11-27 | 2002-11-27 | |
PCT/EP2003/050839 WO2004048479A1 (en) | 2002-11-27 | 2003-11-17 | Preparation of beta quinacridone pigments |
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JP2006508210A true JP2006508210A (ja) | 2006-03-09 |
JP2006508210A5 JP2006508210A5 (ja) | 2010-10-28 |
JP4608320B2 JP4608320B2 (ja) | 2011-01-12 |
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US (1) | US6864371B2 (ja) |
EP (1) | EP1565530B1 (ja) |
JP (1) | JP4608320B2 (ja) |
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CN (1) | CN100349988C (ja) |
AT (1) | ATE372358T1 (ja) |
AU (1) | AU2003296761A1 (ja) |
BR (1) | BR0316531A (ja) |
CA (1) | CA2505763A1 (ja) |
DE (1) | DE60316179T2 (ja) |
MX (1) | MXPA05005679A (ja) |
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Cited By (1)
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JP5800109B1 (ja) * | 2013-12-19 | 2015-10-28 | Dic株式会社 | 低アミン含有量のキナクリドン顔料の製造方法 |
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US20060249245A1 (en) * | 2000-10-31 | 2006-11-09 | Bernard Balling | Ceramic and glass correction inks |
US7211139B2 (en) * | 2005-05-03 | 2007-05-01 | Sun Chemical Corporation | Process for preparing nanoscale quinacridone |
US7427323B1 (en) * | 2007-06-07 | 2008-09-23 | Xerox Corporation | Quinacridone nanoscale pigment particles |
US7427324B1 (en) * | 2007-06-07 | 2008-09-23 | Xerox Corporation | Methods of making quinacridone nanoscale pigment particles |
CN105348127A (zh) * | 2015-12-08 | 2016-02-24 | 温州金源化工有限公司 | 喹吖啶酮中间体的制备方法 |
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DE60316179D1 (de) | 2007-10-18 |
WO2004048479A1 (en) | 2004-06-10 |
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JP4608320B2 (ja) | 2011-01-12 |
RU2005120168A (ru) | 2006-05-10 |
KR20050084035A (ko) | 2005-08-26 |
AU2003296761A1 (en) | 2004-06-18 |
CN1717455A (zh) | 2006-01-04 |
US6864371B2 (en) | 2005-03-08 |
ATE372358T1 (de) | 2007-09-15 |
BR0316531A (pt) | 2005-10-04 |
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