JPH04239567A - Purification of organic pigment - Google Patents
Purification of organic pigmentInfo
- Publication number
- JPH04239567A JPH04239567A JP2037091A JP2037091A JPH04239567A JP H04239567 A JPH04239567 A JP H04239567A JP 2037091 A JP2037091 A JP 2037091A JP 2037091 A JP2037091 A JP 2037091A JP H04239567 A JPH04239567 A JP H04239567A
- Authority
- JP
- Japan
- Prior art keywords
- organic pigment
- pigment
- organic
- phosphoric acid
- acid amide
- 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.)
- Pending
Links
- 239000012860 organic pigment Substances 0.000 title claims abstract description 46
- 238000000746 purification Methods 0.000 title claims description 13
- PTMHPRAIXMAOOB-UHFFFAOYSA-N phosphoramidic acid Chemical compound NP(O)(O)=O PTMHPRAIXMAOOB-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000002904 solvent Substances 0.000 claims abstract description 6
- 238000001816 cooling Methods 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 abstract description 7
- 239000004065 semiconductor Substances 0.000 abstract description 2
- 230000001376 precipitating effect Effects 0.000 abstract 1
- 239000000049 pigment Substances 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 238000000921 elemental analysis Methods 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 239000012776 electronic material Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 1
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- -1 methanol and ethanol Chemical class 0.000 description 1
- ROZPNEGZBIUWBX-UHFFFAOYSA-N n-[bis(diethylamino)phosphoryl]-n-ethylethanamine Chemical compound CCN(CC)P(=O)(N(CC)CC)N(CC)CC ROZPNEGZBIUWBX-UHFFFAOYSA-N 0.000 description 1
- WAQPJHNWYPETBC-UHFFFAOYSA-N n-bis(dipropylamino)phosphoryl-n-propylpropan-1-amine Chemical compound CCCN(CCC)P(=O)(N(CCC)CCC)N(CCC)CCC WAQPJHNWYPETBC-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 108091008695 photoreceptors Proteins 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- AXMCIYLNKNGNOT-UHFFFAOYSA-M sodium;3-[[4-[(4-dimethylazaniumylidenecyclohexa-2,5-dien-1-ylidene)-[4-[ethyl-[(3-sulfonatophenyl)methyl]amino]phenyl]methyl]-n-ethylanilino]methyl]benzenesulfonate Chemical compound [Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](C)C)C=2C=CC(=CC=2)N(CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 AXMCIYLNKNGNOT-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
Abstract
Description
【０００１】0001
【産業上の利用分野】本発明は有機顔料の精製法に関す
るものである。詳しくは、有機顔料をリン酸アミドを用
いて精製する方法に関するものである。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for purifying organic pigments. Specifically, the present invention relates to a method for purifying organic pigments using phosphoric acid amide.
【０００２】0002
【従来の技術】有機顔料は塗料・印刷インキ・合成樹脂
等の着色や電子材料として有用であり、近年電子写真感
光体として盛んに用いられるようになった。有機顔料を
有機半導体や太陽電池等の電子材料に利用する場合、顔
料中の不純物が電気的特性の阻害要因となることが指摘
されているが、有機顔料は一般に有機溶媒に難溶性であ
るため精製が困難であった。BACKGROUND OF THE INVENTION Organic pigments are useful for coloring paints, printing inks, synthetic resins, etc. and as electronic materials, and have recently come to be widely used as electrophotographic photoreceptors. When organic pigments are used in electronic materials such as organic semiconductors and solar cells, it has been pointed out that impurities in the pigments impede electrical properties, but organic pigments are generally poorly soluble in organic solvents. Purification was difficult.
【０００３】従来、有機顔料の一般的な精製法としては
、顔料を濃硫酸に溶解した後、水で希釈して析出させて
分離する方法が知られているが、この方法では水に難溶
性の不純物の除去が期待できないうえ、精製処理の際に
顔料が分解する恐れがある。また、昇華による精製法も
知られているが、有機顔料が熱的に不安定であるため適
用範囲が著しく限定されるのみでなく、精製設備に多大
の費用を要する等の問題がある。更にトリフルオロ酢酸
がフタロシアニン顔料を溶解させることも知られている
が（特開平２−２６９７７６号公報）、フタロシアニン
顔料の種類によっては一部分解されることがある。[0003] Conventionally, a general method for purifying organic pigments is to dissolve the pigment in concentrated sulfuric acid, dilute it with water, and separate it by precipitation. It cannot be expected to remove impurities, and there is a risk that the pigment will decompose during the purification process. Further, a purification method by sublimation is also known, but since the organic pigment is thermally unstable, the range of application is significantly limited, and there are problems such as requiring a large amount of cost for purification equipment. Furthermore, it is known that trifluoroacetic acid dissolves phthalocyanine pigments (JP-A-2-269776), but depending on the type of phthalocyanine pigments, it may be partially decomposed.
【０００４】0004
【発明が解決しようとする課題】本発明は、顔料の分解
を生ずることなく、高純度の有機顔料を容易かつ効率よ
く製造し得る精製法を提供することを目的とするもので
ある。SUMMARY OF THE INVENTION An object of the present invention is to provide a purification method that can easily and efficiently produce highly pure organic pigments without causing decomposition of the pigments.
【０００５】[0005]
【課題を解決するための手段】本発明者等は、上記の目
的を達成するため検討を重ねた結果、有機顔料を特定の
リン酸アミドに溶解し、次いで再結晶するか又は貧溶媒
を添加して再沈澱させることにより、顔料の分解を来す
ことなく極めて容易に高純度の有機顔料が得られること
を見い出し本発明に到達した。即ち、本発明の要旨は、
有機顔料を、請求項１における一般式（１）で表される
リン酸アミドに溶解し、次いで冷却及び／又は貧溶媒を
加えて有機顔料を析出分離することを特徴とする精製法
に存する。[Means for Solving the Problem] As a result of repeated studies in order to achieve the above object, the present inventors have solved the problem by dissolving an organic pigment in a specific phosphoric acid amide, and then recrystallizing it or adding a poor solvent. The present invention has been achieved based on the discovery that highly pure organic pigments can be obtained extremely easily without decomposition of the pigments by reprecipitation. That is, the gist of the present invention is
The present invention resides in a purification method characterized by dissolving an organic pigment in a phosphoric acid amide represented by the general formula (1) according to claim 1, and then cooling and/or adding a poor solvent to precipitate and separate the organic pigment.
【０００６】以下、本発明を詳細に説明する。本発明に
適用される有機顔料としては特に限られるものでなく、
例えば、アゾ系、トリフェニルメタン系、キノリン系、
アントラキノン系、ペリノン系、ペリレン系、ジオキサ
ジン系、キナクリドン系、チオインジゴ系、フタロシア
ニン系等の各種の有機顔料が挙げられる。これらはまた
、金属含有有機顔料であってもよく、あるいは金属を含
有しない有機顔料であってもよい。The present invention will be explained in detail below. The organic pigment applicable to the present invention is not particularly limited,
For example, azo type, triphenylmethane type, quinoline type,
Examples include various organic pigments such as anthraquinone, perinone, perylene, dioxazine, quinacridone, thioindigo, and phthalocyanine pigments. These may also be metal-containing organic pigments or metal-free organic pigments.
【０００７】本発明に使用される前記一般式（１）で表
されるリン酸アミドの具体例としては、例えば、ヘキサ
メチルホスホリックトリアミド、ヘキサエチルホスホリ
ックトリアミド、ヘキサプロピルホスホリックトリアミ
ド等が挙げられる。Specific examples of the phosphoric acid amide represented by the general formula (1) used in the present invention include hexamethylphosphoric triamide, hexaethylphosphoric triamide, and hexapropylphosphoric triamide. etc.
【０００８】本発明においては、まず有機顔料を上記の
リン酸アミドに溶解する。リン酸アミドの使用量として
は、有機顔料を溶解するに足る量であればよく、有機顔
料の種類によっても異なるが、通常有機顔料に対して５
〜２００倍量（重量比）のリン酸アミドが使用される。
なお、金属含有有機顔料の場合は、金属を含有しない有
機顔料よりも一般に溶解度が低いので、リン酸アミドの
使用比率を高めることが必要である。溶解時の温度は任
意に選ぶことができるが、通常は２０〜２００℃の範囲
、好ましくは５０〜１５０℃の範囲から選ばれる。In the present invention, an organic pigment is first dissolved in the above-mentioned phosphoric acid amide. The amount of phosphoric acid amide to be used is sufficient as long as it is sufficient to dissolve the organic pigment, and although it varies depending on the type of organic pigment, it is usually 5% to the organic pigment.
~200 times the amount (by weight) of phosphoric acid amide is used. Note that in the case of metal-containing organic pigments, the solubility is generally lower than that of organic pigments that do not contain metals, so it is necessary to increase the usage ratio of phosphoric acid amide. The temperature during melting can be arbitrarily selected, but is usually selected from the range of 20 to 200°C, preferably from 50 to 150°C.
【０００９】有機顔料を溶解したリン酸アミド溶液から
精製された有機顔料を採取するには、有機顔料をリン酸
アミドと混合して所定の温度に保持したのち濾過等によ
り不溶物を除去し、得られた溶液を冷却して有機顔料を
析出させて分離するか、あるいは該溶液に貧溶媒を添加
して有機顔料を再沈澱させる方法が採用される。冷却温
度は有機顔料の種類や溶解時の温度等により適宜選択す
るすることができる。貧溶媒としては、有機顔料の溶解
性が低いものであれば特に限られるものでないが、例え
ば水、メタノ−ル、エタノ−ル等の低級アルコ−ル類又
はジエチルエ−テルのようなエ−テル類が使用される。[0009] To collect the purified organic pigment from the phosphoric acid amide solution in which the organic pigment is dissolved, the organic pigment is mixed with the phosphoric acid amide, maintained at a predetermined temperature, and then insoluble materials are removed by filtration or the like. A method is adopted in which the obtained solution is cooled to precipitate and separate the organic pigment, or a poor solvent is added to the solution to reprecipitate the organic pigment. The cooling temperature can be appropriately selected depending on the type of organic pigment, the temperature at the time of dissolution, etc. The poor solvent is not particularly limited as long as it has low solubility for the organic pigment, but examples include water, lower alcohols such as methanol and ethanol, and ethers such as diethyl ether. class is used.
【００１０】0010
【実施例】以下本発明を実施例について更に詳細に説明
するが、本発明はその要旨を超えない限りこれ等の実施
例に限定されるものではない。EXAMPLES The present invention will be explained in more detail with reference to Examples below, but the present invention is not limited to these Examples unless the gist thereof is exceeded.
【００１１】実施例１
アゾ系の赤色有機顔料ブリリアントカ−ミン６ＢＧ（住
化カラ−社製）４ｇとヘキサメチルホスホリックトリア
ミド１００ ｍｌとを２００ ｍｌのフラスコに入れ、
９０℃に加熱して１時間攪拌したのち熱濾過した。濾液
にメタノ−ル２０ ｍｌを加えて室温に冷却し、濾過し
て析出物を採取し、メタノ−ルで洗浄したのち乾燥して
精製顔料１．２ｇを得た。精製前及び精製後における顔
料の元素分析値は表１に示す通りであった。Example 1 4 g of an azo red organic pigment Brilliant Carmine 6BG (manufactured by Sumika Color Co., Ltd.) and 100 ml of hexamethylphosphoric triamide were placed in a 200 ml flask.
The mixture was heated to 90°C, stirred for 1 hour, and then filtered hot. 20 ml of methanol was added to the filtrate, cooled to room temperature, filtered to collect a precipitate, washed with methanol, and dried to obtain 1.2 g of purified pigment. The elemental analysis values of the pigment before and after purification were as shown in Table 1.
【００１２】0012
【表１】[Table 1]
【００１３】実施例２
フタロシアニン系の青色有機顔料シアニンブル−（東洋
インキ社製）１ ｇとヘキサメチルホスホリックトリア
ミド１００ ｍｌとを２００ ｍｌのフラスコに入れ、
１２０℃に加熱して１時間攪拌したのち熱濾過した。濾
液にメタノ−ル５０ ｍｌを加えて室温に冷却し、濾過
して析出物を採取し、メタノ−ルで洗浄したのち乾燥し
て精製顔料０．３ ｇを得た。
精製前及び精製後における顔料の元素分析値は表２に示
す通りであった。Example 2 1 g of a phthalocyanine-based blue organic pigment Cyanine Blue (manufactured by Toyo Ink Co., Ltd.) and 100 ml of hexamethylphosphoric triamide were placed in a 200 ml flask.
The mixture was heated to 120°C, stirred for 1 hour, and then filtered hot. 50 ml of methanol was added to the filtrate, cooled to room temperature, filtered to collect a precipitate, washed with methanol, and dried to obtain 0.3 g of purified pigment. The elemental analysis values of the pigment before and after purification were as shown in Table 2.
【００１４】[0014]
【表２】[Table 2]
【００１５】実施例３
トリフェニルメタン系の青色有機顔料ビクトリアブル−
（東京化成工業社製）２ｇとヘキサメチルホスホリック
トリアミド１０ ｍｌとを５０ ｍｌのフラスコに入れ
、９０℃に加熱して１０分間攪拌したのち熱濾過した。
濾液を０℃に冷却し、濾過して析出物を採取し、ジエチ
ルエ−テルで洗浄したのち真空乾燥して精製顔料１．７
ｇを得た。精製前及び精製後における顔料の元素分析
値は表３に示す通りであった。Example 3 Triphenylmethane-based blue organic pigment Victoria Blue
(manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 10 ml of hexamethylphosphoric triamide were placed in a 50 ml flask, heated to 90°C, stirred for 10 minutes, and then filtered hot. The filtrate was cooled to 0°C, filtered to collect the precipitate, washed with diethyl ether, and dried in vacuum to obtain a purified pigment of 1.7
I got g. The elemental analysis values of the pigment before and after purification were as shown in Table 3.
【００１６】[0016]
【表３】[Table 3]
【００１７】実施例４
トリフェニルメタン系の紫色有機顔料アシッドバイオレ
ット６Ｂ（東京化成工業社製）２ ｇ及びヘキサメチル
ホスホリックトリアミド８ ｍｌを５０ ｍｌのフラス
コに入れ、９０℃に加熱して１０分間攪拌したのち熱濾
過した。濾液を０℃に冷却しエ−テル５０ ｍｌを加え
た。次いで析出した顔料を濾取し、ジエチルエ−テルで
洗浄したのち真空乾燥して精製顔料１．７ ｇを得た。
精製前及び精製後における顔料の元素分析値は表４に示
す通りであった。Example 4 2 g of the triphenylmethane-based purple organic pigment Acid Violet 6B (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 8 ml of hexamethylphosphoric triamide were placed in a 50 ml flask, heated to 90° C. for 10 After stirring for a minute, it was filtered hot. The filtrate was cooled to 0°C and 50 ml of ether was added. Next, the precipitated pigment was collected by filtration, washed with diethyl ether, and then vacuum dried to obtain 1.7 g of purified pigment. The elemental analysis values of the pigment before and after purification were as shown in Table 4.
【００１８】[0018]
【表４】[Table 4]
【００１９】実施例５
アントラキノン系の青色有機顔料インダンスレンブル−
ＧＣＤ（東京化成工業社製）１ ｇ及びヘキサメチルホ
スホリックトリアミド１００ ｍｌを２００ ｍｌのフ
ラスコに入れ、１１０℃に加熱して１時間攪拌したのち
熱濾過した。濾液を室温に冷却してエ−テル１５０ ｍ
ｌを加えた。次いで析出した顔料を濾取し、ジエチルエ
−テルで洗浄したのち真空乾燥して精製顔料０．０３
ｇを得た。精製前及び精製後における顔料の元素分析値
は表５に示す通りであった。Example 5 Anthraquinone-based blue organic pigment indanthremble
1 g of GCD (manufactured by Tokyo Chemical Industry Co., Ltd.) and 100 ml of hexamethylphosphoric triamide were placed in a 200 ml flask, heated to 110° C., stirred for 1 hour, and then filtered hot. The filtrate was cooled to room temperature and diluted with 150 m
Added l. Next, the precipitated pigment was collected by filtration, washed with diethyl ether, and vacuum dried to obtain a purified pigment of 0.03
I got g. The elemental analysis values of the pigment before and after purification were as shown in Table 5.
【００２０】[0020]
【表５】[Table 5]
【００２１】[0021]
【発明の効果】本発明の方法によれば、有機顔料の分解
がなく、従来法に比べて容易かつ効果的に有機顔料を精
製することができるので工業的規模における高純度有機
顔料の製造上極めて有利である。Effects of the Invention: According to the method of the present invention, there is no decomposition of organic pigments, and organic pigments can be purified more easily and effectively than conventional methods. Extremely advantageous.
Claims (1)
で表されるリン酸アミドに溶解し、次いで冷却及び／又
は貧溶媒を加えて有機顔料を析出分離することを特徴と
する精製法。[Claim 1] An organic pigment represented by the following general formula (1) [Chemical formula 1] (wherein R1 to R6 represent an alkyl group having 1 to 3 carbon atoms)
A purification method characterized by dissolving an organic pigment in a phosphoric acid amide represented by the formula and then cooling and/or adding a poor solvent to precipitate and separate an organic pigment.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2037091A JPH04239567A (en) | 1991-01-22 | 1991-01-22 | Purification of organic pigment |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2037091A JPH04239567A (en) | 1991-01-22 | 1991-01-22 | Purification of organic pigment |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH04239567A true JPH04239567A (en) | 1992-08-27 |
Family
ID=12025187
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2037091A Pending JPH04239567A (en) | 1991-01-22 | 1991-01-22 | Purification of organic pigment |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04239567A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007154212A (en) * | 2007-02-16 | 2007-06-21 | Fujifilm Corp | Organic pigment dispersion and method for producing the same |
| JP2009269937A (en) * | 2008-04-30 | 2009-11-19 | Canon Inc | Method for producing inkjet recording ink, inkjet recording ink, inkjet recording method, ink cartridge, recording unit and inkjet recording apparatus |
-
1991
- 1991-01-22 JP JP2037091A patent/JPH04239567A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007154212A (en) * | 2007-02-16 | 2007-06-21 | Fujifilm Corp | Organic pigment dispersion and method for producing the same |
| JP2009269937A (en) * | 2008-04-30 | 2009-11-19 | Canon Inc | Method for producing inkjet recording ink, inkjet recording ink, inkjet recording method, ink cartridge, recording unit and inkjet recording apparatus |
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