JPH029882A - Production of phthalocyanines - Google Patents
Production of phthalocyaninesInfo
- Publication number
- JPH029882A JPH029882A JP15994988A JP15994988A JPH029882A JP H029882 A JPH029882 A JP H029882A JP 15994988 A JP15994988 A JP 15994988A JP 15994988 A JP15994988 A JP 15994988A JP H029882 A JPH029882 A JP H029882A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- phthalocyanine
- group
- solvent
- alkoxyl
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 239000002904 solvent Substances 0.000 claims abstract description 16
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 12
- 229910052796 boron Inorganic materials 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 11
- 125000005843 halogen group Chemical group 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- PMJMHCXAGMRGBZ-UHFFFAOYSA-N subphthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(=N3)N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C3=N1 PMJMHCXAGMRGBZ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 3
- 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 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract description 10
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 abstract description 6
- RZVCEPSDYHAHLX-UHFFFAOYSA-N 3-iminoisoindol-1-amine Chemical compound C1=CC=C2C(N)=NC(=N)C2=C1 RZVCEPSDYHAHLX-UHFFFAOYSA-N 0.000 abstract description 5
- 239000006227 byproduct Substances 0.000 abstract description 4
- 229910052736 halogen Inorganic materials 0.000 abstract description 4
- 150000002367 halogens Chemical class 0.000 abstract description 3
- 239000004973 liquid crystal related substance Substances 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- 239000012046 mixed solvent Substances 0.000 abstract description 2
- 230000003287 optical effect Effects 0.000 abstract description 2
- 239000004065 semiconductor Substances 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 9
- 238000000862 absorption spectrum Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- -1 4,5-dimethyliminoindoline Chemical compound 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- JBPFCKKZYCHCRF-UHFFFAOYSA-N 3-imino-6,7-dimethylisoindol-1-amine Chemical compound CC1=CC=C2C(=N)NC(=N)C2=C1C JBPFCKKZYCHCRF-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical compound N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 description 1
- 229920006391 phthalonitrile polymer Polymers 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- AJSTXXYNEIHPMD-UHFFFAOYSA-N triethyl borate Chemical compound CCOB(OCC)OCC AJSTXXYNEIHPMD-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Description
【発明の詳細な説明】
[産業上の利用分野]
本発明は、ガスセンサー、有機半導体、光デスクメモリ
ー材、液晶等への使用に適するフタロシアニン類、とく
に3:1型非対称フタロシアニン類を製造する方法に関
する。[Detailed Description of the Invention] [Industrial Application Field] The present invention produces phthalocyanines, particularly 3:1 type asymmetric phthalocyanines, suitable for use in gas sensors, organic semiconductors, optical desk memory materials, liquid crystals, etc. Regarding the method.
[従来の技術]
フタロシアニン類の製造法については各種の方法が提案
されてきたが、いずれも種々のフタロシアニン類の混合
物が生成し、その中から目的とするフタロシアニン類を
単離することは容易ではなかった。[Prior Art] Various methods have been proposed for producing phthalocyanines, but all of them produce a mixture of various phthalocyanines, and it is not easy to isolate the desired phthalocyanine from the mixture. There wasn't.
例えば従来提案されてきた3、1型非対称フタロシアニ
ンの製造法は、ジイミノインインドリンとその誘導体、
もしくはフタロニトリルとその誘導体からなる2Mの原
料を、金属塩等とともに混合加熱する方法である。これ
らの方法では、目的とする3:1型非対称フタロシアニ
ンの他にそれ以外のフタロシアニンおよび/4たはその
誘導体がかなり多量に生成するため、生成した混合物中
から3:1型非対称フタロシアニンを単離する必要があ
った。しかし、フタロシアニンおよびその誘導体は各種
の溶媒に対し難溶性であるため、その単離は非常に困難
である。For example, the production method of type 3,1 asymmetric phthalocyanine that has been proposed so far includes diiminoinindoline and its derivatives,
Alternatively, there is a method in which a 2M raw material consisting of phthalonitrile and its derivatives is mixed and heated with a metal salt or the like. In these methods, in addition to the target 3:1 type asymmetric phthalocyanine, other phthalocyanines and/4 or their derivatives are produced in considerable amounts, so it is necessary to isolate the 3:1 type asymmetric phthalocyanine from the resulting mixture. I needed to. However, since phthalocyanine and its derivatives are sparingly soluble in various solvents, isolation thereof is extremely difficult.
[発明が解決しようとする課題]
本発明は、目的生成物であるフタロシアニン類例えば3
:1型非対称フタロシアニン類以外のフタロシアニン類
を生成しないフタロシアニン類の製造法を提供すること
により、各種混合物中から目的生成物を単離するという
前記従来技術が有していた課題を解決するフタロシアニ
ン類の製造法を提供する。[Problems to be Solved by the Invention] The present invention solves the problem of phthalocyanines, which are target products, such as 3
: A phthalocyanine that solves the problem of isolating a target product from various mixtures, which was posed by the prior art, by providing a method for producing phthalocyanines that does not produce phthalocyanines other than type 1 asymmetric phthalocyanines. Provides a manufacturing method.
[課題を解決するための手段]
本発明は1式で1)
(式中、R4−R1は相互に独立に、水素原子、アルキ
ル基、ニトロ基、アルコキシル基またはハロゲン原子を
示し、Xはハロゲン原子またはアルコキシル基を示す)
の5ub−フタロシアニンホウ素錯体と、式(2)(式
中、R′1〜R°、は相互に独立に、水素原子、アルキ
ル基、ニトロ基、アルコキシル基、ハロゲン原子、ニト
ロ基またはシアン基を示す)のジイミノイソインドリン
と念、式(1)および式(2)の両化合物を溶解する溶
媒中で反応させ、式(3)
(式中、R1−R1およびRo1〜R゛4は式(1)お
よび式(2)と同じ意味を有する)
のフタロシアニン類を製造する方法を提供する。[Means for Solving the Problems] The present invention has the following formula: atom or alkoxyl group) and a 5ub-phthalocyanine boron complex of formula (2) (in the formula, R'1 to R° are each independently a hydrogen atom, an alkyl group, a nitro group, an alkoxyl group, or a halogen atom). , nitro group or cyan group) is reacted with diiminoisoindoline of formula (3) (in which R1-R1 and Ro1 to R'4 have the same meanings as formulas (1) and (2)) A method for producing phthalocyanines is provided.
さらに本発明は、式(1)の5ub−フタロシアニンホ
ウ素錯体と式(2)においてR′、〜R°、の少なくと
も1個はそれぞれが対応するR1−R1と異なるジイミ
ノイソインドリン(以下式(2°)のジイミノイソイン
ドリンという)とを反応させ、3:1型非対称フタロシ
アニン類(以下式(3′)のフタロシアニン類という)
の製造に適した方法を提供する。Furthermore, the present invention provides a 5ub-phthalocyanine boron complex of formula (1) and a diiminoisoindoline (hereinafter formula ( 2°) diiminoisoindoline) to form 3:1 type asymmetric phthalocyanines (hereinafter referred to as phthalocyanines of formula (3')).
To provide a method suitable for manufacturing.
本発明においてそれぞれが対応するとは、RがR3に、
Ro2がR2に、Ro、がR1に、Ro、がR4に対応
することを意味する。In the present invention, R corresponds to R3,
This means that Ro2 corresponds to R2, Ro corresponds to R1, and Ro corresponds to R4.
本発明で用いる5ub−フタロシアニンボウ索i13体
のハロゲン化物およびその誘導体はモチ1〜シエエテフ
ユルケミー(Monatshefte fur
Chemie 、 150 頁 、 1972
) 3己載の合成法によって得ることができる。さら
にこの化合物のハロゲン配位子のアルコキシル基への置
換は、例えば該化合物のα−クロルナフタリン溶液を大
過剰のアルコール中で加熱することによって達成される
。The halides of 5ub-phthalocyanine I13 and derivatives thereof used in the present invention are
Chemie, 150 pages, 1972
) 3 can be obtained by the synthesis method described above. Further, substitution of the halogen ligand of this compound with an alkoxyl group is achieved, for example, by heating a solution of the compound in α-chlornaphthalene in a large excess of alcohol.
本発明で用いる溶媒は、式(1)および式(2)の化合
物の少なくとも一部をともに溶解し、かつ式(4)
に示す反応を、反応温度内で生じせしめない溶媒である
。式(4)の反応はジメチルエタノールアミン等のアミ
ン系溶媒を使用したときに生じ易いことが知られている
。即ち本発明での使用に適する溶媒としては、具体的に
は例えばα−クロルナフタリンとジメチルスルホキシド
(DMSO)の1=1〜1:2の混合溶媒である。外に
もアミルアルコール、ジメチルホルムアミド等上記条件
を満足する溶媒であればいずれも使用できる。溶媒の使
用量は式(1)および式(2)の化合物の両者を全部溶
解する量が好ましいが、両者の一部づつを溶解する星で
あってもよい。The solvent used in the present invention is a solvent that dissolves at least a portion of the compounds of formula (1) and formula (2) and does not cause the reaction represented by formula (4) to occur within the reaction temperature. It is known that the reaction of formula (4) tends to occur when an amine solvent such as dimethylethanolamine is used. Specifically, a solvent suitable for use in the present invention is, for example, a mixed solvent of α-chlornaphthalene and dimethyl sulfoxide (DMSO) in a ratio of 1=1 to 1:2. In addition, any solvent that satisfies the above conditions, such as amyl alcohol and dimethylformamide, can be used. The amount of solvent used is preferably such that it completely dissolves both the compounds of formula (1) and formula (2), but it may be sufficient to dissolve only a portion of each compound.
反応温度は100℃以下が好ましく、さらに好ましくは
70〜100℃である。70℃より下では反応速度が遅
く、100℃を超えると目的生成物以外の副生物を生じ
易くなるので好ましくない。The reaction temperature is preferably 100°C or lower, more preferably 70 to 100°C. If the temperature is lower than 70°C, the reaction rate is slow, and if it exceeds 100°C, by-products other than the desired product are likely to be produced, which is not preferable.
しかし本発明において反応温度は上記範囲に限定される
ものではなく、目的生成物の種類によっては反応温度が
100℃を超えても副生物を生じない場合があり、目的
生成物の種類によって反応温度を適宜還択することがで
きる。However, in the present invention, the reaction temperature is not limited to the above range; depending on the type of target product, no by-product may be produced even if the reaction temperature exceeds 100°C; can be selected as appropriate.
反応時間は、反応温度、原料の溶媒への溶解状態によっ
て異なるが、反応終点は式(1)の化合物の色がほとん
ど消失する時点によって判断できる。The reaction time varies depending on the reaction temperature and the state of dissolution of the raw materials in the solvent, but the end point of the reaction can be determined by the point at which the color of the compound of formula (1) almost disappears.
[実施例]
以下実施例により、本発明をより具体的に説明する。各
実施例中、部は重量部を示す。[Example] The present invention will be described in more detail with reference to Examples below. In each example, parts indicate parts by weight.
実施例I
DMSO16,000部、α−クロルナフタリンs、o
oo部の溶媒中に5ub−フタロシアニンポウ素錯体塩
化物(式(1)中、R3−R1がI−Tであり、Xが0
1である)200部、4.5−ジメチルイミノインドリ
ン(式(2゛)中、R’ + 、 R’ +がHであり
、Ro2+ R’、がCH*’である)800部を加え
、80℃で4時間撹拌すると、沈澱として青色の2.3
−ジメチルフタロシアニン(式(3%式%
R′コがCH,である)を得た。沈澱を濾過し、つぃで
熱したDMSO、メタノール、アセトンのjlliTで
洗浄し、50〜60°Cで乾燥した。Example I 16,000 parts of DMSO, α-chlornaphthalene s, o
5ub-phthalocyanine boron complex chloride (in formula (1), R3-R1 is IT and X is 0
1), 800 parts of 4,5-dimethyliminoindoline (in formula (2゛), R' + , R' + are H, and Ro2+ R' is CH*'), When stirred at 80℃ for 4 hours, blue 2.3 precipitate
-Dimethylphthalocyanine (formula (3% formula % R' is CH) was obtained. The precipitate was filtered, washed with hot DMSO, methanol, and acetone at 50-60 °C. Dry.
2.3−ジメチルフタロシアニンの量は28部であった
。得られた2、3−ジメチルフタロシアニンの硫酸溶媒
中での吸収スペクトルを、フタロシアニンおよび2.3
.6.7.10.11.14.15−オクタメチルフタ
ロシアニンのスペクトルと比較して第1図に示す。The amount of 2,3-dimethylphthalocyanine was 28 parts. The absorption spectrum of the obtained 2,3-dimethylphthalocyanine in a sulfuric acid solvent was compared to phthalocyanine and 2.3-dimethylphthalocyanine.
.. A comparison with the spectrum of 6.7.10.11.14.15-octamethylphthalocyanine is shown in FIG.
2.3−ジメチルフタロシアニンとLi塩とし、CD3
0D中で測定したH −N M Rのデータを以下に示
す。2.3-dimethylphthalocyanine and Li salt, CD3
The H-NMR data measured in 0D is shown below.
δ=9.42 (6H,q)、9.15 (2H,S)
、 8.03 (6H,CI) 、 2.86
<611 、S)実施例2
sub−フタロシアニンホウ素錯体塩化物のα−クロル
ナフタリン溶液を大過剰のエタノール中で温度78℃で
加熱することにより、5ub−フタロシアニンポウ素釦
体エトキシ化物(式(1)中R1〜R4がHであり、X
がQC,H5である)を得た。δ=9.42 (6H,q), 9.15 (2H,S)
, 8.03 (6H, CI) , 2.86
<611,S) Example 2 A solution of sub-phthalocyanine boron complex chloride in α-chlornaphthalene was heated in a large excess of ethanol at a temperature of 78°C to form a 5ub-phthalocyanine boron ethoxide (formula (1) ) in which R1 to R4 are H, and
is QC, H5) was obtained.
このエトキシ化物のCDCl3中で測定したH−NMR
データは次のとおりである。H-NMR of this ethoxylated product measured in CDCl3
The data are as follows.
δ−8,85,(6H,q)、7.89 (61(、q
>、1.52 (2H,q)、0.17 (31−1,
t)実施例1と同じ溶媒24.000部中に、得られた
5ub−フタロシアニンホウ素錯体エトギシ化物100
部、4.5−ジメチlレジイミノイソイン・ドリフ10
0部を加え、90℃で3時間撹拌して沈澱を得た。この
沈澱を実施例1と同様の方法で洗浄し乾燥した。得られ
た生成物は、青色の2.3−ジメチルフタロシアニンで
あった。δ-8,85,(6H,q),7.89(61(,q
>, 1.52 (2H, q), 0.17 (31-1,
t) In 24.000 parts of the same solvent as in Example 1, 100 parts of the obtained 5ub-phthalocyanine boron complex ethoxylate
parts, 4,5-dimethyl-resiiminoisoin drift 10
0 part was added and stirred at 90°C for 3 hours to obtain a precipitate. This precipitate was washed and dried in the same manner as in Example 1. The product obtained was blue 2,3-dimethylphthalocyanine.
実施例3
sub−フタロシアニンホウ素錯体塩化物のα−クロル
ナフタリン溶液を大過剰のt−ブタノール中で温度11
8℃で加熱することにより、5ub−フタロシアニンホ
ウ素錯体t−ブトキシ化物(式(1)%式%
る)を得た。このt−ブトキシ化物のCDC1j中で測
定したH−NMRデータは次のとおりである。Example 3 A solution of sub-phthalocyanine boron complex chloride in α-chlornaphthalene was heated to 11°C in a large excess of t-butanol.
By heating at 8°C, a 5ub-phthalocyanine boron complex t-butoxylated product (formula (1)) was obtained. The H-NMR data of this t-butoxylated product measured in CDC1j are as follows.
δ−8,85(6H,q>、7.88 (6H,q)、
0.04 (9H,S)
実施例1と同じ溶媒24000部中に、得られた5ub
−フタロシアニンホウ素銘体t−ブトキシ化物100部
、4.5−ジメチルジイミノイソインドリン100部を
加え、90℃で3時間撹拌して沈澱を得た。この沈澱を
実施例1と同様の方法で洗浄し乾燥した。得られた生成
物は、青色の2.3−ジメチルフタロシアニンであった
。δ-8,85 (6H,q>, 7.88 (6H,q),
0.04 (9H,S) In 24000 parts of the same solvent as in Example 1, the obtained 5ub
-100 parts of phthalocyanine boron t-butoxylated product and 100 parts of 4,5-dimethyldiiminoisoindoline were added and stirred at 90°C for 3 hours to obtain a precipitate. This precipitate was washed and dried in the same manner as in Example 1. The product obtained was blue 2,3-dimethylphthalocyanine.
実施例4
アミルアルコール24.000部中に実11ON2で得
られたs u b−フタロシアニンボウ素錯体エトキシ
化物100部、4.5−ジメチルジイミノイソインドリ
ン100部を加え、90°Cで1時間撹拌して沈澱を得
た。この沈澱を実施例1と同様の方法で洗浄し乾燥した
。得られた生成物は青色の2.3−ジメチルフタロシア
ニンであった。Example 4 To 24.000 parts of amyl alcohol were added 100 parts of the su b-phthalocyanine complex ethoxylate obtained in Example 11ON2 and 100 parts of 4,5-dimethyldiiminoisoindoline, and the mixture was heated at 90°C for 1 hour. A precipitate was obtained by stirring. This precipitate was washed and dried in the same manner as in Example 1. The product obtained was blue 2,3-dimethylphthalocyanine.
[発明の効果]
本発明によれば、目的生成物であるフタロシアニン化合
物、あるいは3:1型非対称フタロシアニン化合物のみ
が反応終了時に沈澱として生成するので、単に沢過し、
洗浄するのみで該化合物を得ることができる。このため
従来の合成法では困難であったフタロシアニン化合物あ
るいは3・1型非対称フタロシアニン化合物からの他の
フタロシアニン化合物等の副生物の単離を不要とすると
いう顕著な効果を奏する。[Effects of the Invention] According to the present invention, only the target product, the phthalocyanine compound or the 3:1 type asymmetric phthalocyanine compound, is produced as a precipitate at the end of the reaction.
The compound can be obtained only by washing. Therefore, this method has the remarkable effect of eliminating the need to isolate by-products such as phthalocyanine compounds or other phthalocyanine compounds from type 3/1 asymmetric phthalocyanine compounds, which was difficult with conventional synthesis methods.
第1図は、実施例1で得られた本発明の2.3−ジメチ
ルフタロシアニンの硫酸溶媒中での吸収スペクトルを、
フタロシアニンおよび2.3.6.7.10.11.1
4.15−オクタメチルフタロシアニンの吸収スペクト
ルと比較して示す。
a:2.3−ジメチルフタロシアニンの吸収スペクトル
b=フタロシアニンの吸収スペク1〜ルC:2.3.6
.7.10.11.14.15−オクタメチルフタロシ
アニンの吸収スペクトル特許出願人 東洋インキ製造株
式会社FIG. 1 shows the absorption spectrum of 2,3-dimethylphthalocyanine of the present invention obtained in Example 1 in a sulfuric acid solvent.
Phthalocyanines and 2.3.6.7.10.11.1
A comparison with the absorption spectrum of 4.15-octamethylphthalocyanine is shown. a: Absorption spectrum of 2.3-dimethylphthalocyanine b = Absorption spectrum of phthalocyanine 1 to C: 2.3.6
.. 7.10.11.14.Absorption spectrum of 15-octamethylphthalocyanine Patent applicant: Toyo Ink Mfg. Co., Ltd.
Claims (1)
ルキル基、ニトロ基、アルコキシル基またはハロゲン原
子を示し、Xはハロゲン原子またはアルコキシル基を示
す) のsub−フタロシアニンホウ素錯体と、式(2)▲数
式、化学式、表等があります▼(2) (式中、R′_1〜R′_4は相互に独立に、水素原子
、アルキル基、ニトロ基、アルコキシル基、ハロゲン原
子、ニトロ基またはシアノ基を示す) のジイミノイソインドリンとを、式(1)および式(2
)の両化合物の少なくとも1部を溶解する溶媒中で反応
させ、式(3) ▲数式、化学式、表等があります▼(3) (式中、R_1〜R_4およびR′_1〜R′_4は式
(1)および式(2)と同じ意味を有する) のフタロシアニン類を製造する方法。 2、式(1) ▲数式、化学式、表等があります▼(1) (式中、R_1〜R_4は相互に独立に、水素原子、ア
ルキル基、ニトロ基、アルコキシル基またはハロゲン原
子を示し、Xはハロゲン原子またはアルコキシル基を示
す) のsub−フタロシアニンホウ素錯体と、式(2′)▲
数式、化学式、表等があります▼(2′) (式中、R′_1〜R′_4は相互に独立に、水素原子
、アルキル基、ニトロ基、アルコキシル基、ハロゲン原
子、ニトロ基またはシアノ基を示す、ただしR′_1〜
R′_4の少なくとも1個は式(1)のそれぞれが対応
するR_1〜R_4と異なる) のジイミノイソインドリンとを、式(1)および式(2
′)の両化合物の少なくとも1部を溶解する溶媒中で反
応させ、式(3′) ▲数式、化学式、表等があります▼(3′) (式中、R_1〜R_4およびR′_1〜R′_4は式
(1)および式(2′)と同じ意味を有する) の3:1型非対象フタロシアニン類を製造する方法。[Claims] 1. Formula (1) ▲ Numerical formulas, chemical formulas, tables, etc. ▼ (1) (In the formula, R_1 to R_4 each independently represent a hydrogen atom, an alkyl group, a nitro group, an alkoxyl group, or (represents a halogen atom, X represents a halogen atom or an alkoxyl group) and the sub-phthalocyanine boron complex of formula (2) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (2) (in the formula, R'_1 to R' _4 independently represents a hydrogen atom, an alkyl group, a nitro group, an alkoxyl group, a halogen atom, a nitro group, or a cyano group.
) are reacted in a solvent that dissolves at least a part of both compounds, and the formula (3) ▲ has mathematical formulas, chemical formulas, tables, etc. ▼ (3) (where R_1 to R_4 and R'_1 to R'_4 are A method for producing a phthalocyanine having the same meaning as formula (1) and formula (2). 2. Formula (1) ▲ Numerical formulas, chemical formulas, tables, etc. ▼ (1) (In the formula, R_1 to R_4 each independently represent a hydrogen atom, an alkyl group, a nitro group, an alkoxyl group, or a halogen atom, represents a halogen atom or an alkoxyl group) and a sub-phthalocyanine boron complex of formula (2') ▲
There are mathematical formulas, chemical formulas, tables, etc.▼(2') (In the formula, R'_1 to R'_4 are each independently a hydrogen atom, an alkyl group, a nitro group, an alkoxyl group, a halogen atom, a nitro group, or a cyano group. , where R'_1~
At least one of R'_4 is different from the corresponding R_1 to R_4 in formula (1).
') are reacted in a solvent that dissolves at least a part of both compounds, and the formula (3') ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (3') '_4 has the same meaning as formula (1) and formula (2')) A method for producing a 3:1 type asymmetric phthalocyanine.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP15994988A JPH029882A (en) | 1988-06-28 | 1988-06-28 | Production of phthalocyanines |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP15994988A JPH029882A (en) | 1988-06-28 | 1988-06-28 | Production of phthalocyanines |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH029882A true JPH029882A (en) | 1990-01-12 |
Family
ID=15704680
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP15994988A Pending JPH029882A (en) | 1988-06-28 | 1988-06-28 | Production of phthalocyanines |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH029882A (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1994024612A1 (en) * | 1993-04-15 | 1994-10-27 | Zeneca Limited | Chemical compounds |
US5776656A (en) * | 1995-07-28 | 1998-07-07 | Tdk Corporation | Optical recording medium |
WO2002080158A1 (en) * | 2001-03-30 | 2002-10-10 | Interaxia Ag | Optical recording medium and method for the production thereof |
WO2006011446A1 (en) * | 2004-07-27 | 2006-02-02 | Nippon Steel Chemical Co., Ltd. | Composition for color filter and color filter |
-
1988
- 1988-06-28 JP JP15994988A patent/JPH029882A/en active Pending
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1994024612A1 (en) * | 1993-04-15 | 1994-10-27 | Zeneca Limited | Chemical compounds |
US5776656A (en) * | 1995-07-28 | 1998-07-07 | Tdk Corporation | Optical recording medium |
WO2002080158A1 (en) * | 2001-03-30 | 2002-10-10 | Interaxia Ag | Optical recording medium and method for the production thereof |
WO2006011446A1 (en) * | 2004-07-27 | 2006-02-02 | Nippon Steel Chemical Co., Ltd. | Composition for color filter and color filter |
JPWO2006011446A1 (en) * | 2004-07-27 | 2008-07-31 | 新日鐵化学株式会社 | Color filter composition and color filter |
JP4571138B2 (en) * | 2004-07-27 | 2010-10-27 | 新日鐵化学株式会社 | Color filter composition and color filter |
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