JPH0251558B2 - - Google Patents
Info
- Publication number
- JPH0251558B2 JPH0251558B2 JP59279497A JP27949784A JPH0251558B2 JP H0251558 B2 JPH0251558 B2 JP H0251558B2 JP 59279497 A JP59279497 A JP 59279497A JP 27949784 A JP27949784 A JP 27949784A JP H0251558 B2 JPH0251558 B2 JP H0251558B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- group
- phthalocyanine
- infrared
- compound
- 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.)
- Expired - Lifetime
Links
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class 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 9
- -1 phthalocyanine compound Chemical class 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000004171 alkoxy aryl group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 229910052733 gallium Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 229910052738 indium Inorganic materials 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 239000000047 product Substances 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000000921 elemental analysis Methods 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000006096 absorbing agent Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-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
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 229910021617 Indium monochloride Inorganic materials 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- APHGZSBLRQFRCA-UHFFFAOYSA-M indium(1+);chloride Chemical compound [In]Cl APHGZSBLRQFRCA-UHFFFAOYSA-M 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 108091008695 photoreceptors Proteins 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
Landscapes
- Photoreceptors In Electrophotography (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
【発明の詳細な説明】
発明の背景
技術分野
本発明は、フタロシアニン化合物、特に近赤外
および赤外域に吸収をもつフタロシアニン化合物
に関する。
先行技術とその問題点
フタロシアニン化合物は、光、熱、湿度等、い
ずれに対しても安定であり、堅牢性に優れてい
る。特に、金属フタロシアニンは、その高い安定
性と強い色調から各種の染料あるいは顔料として
広く用いられているほか、大きなπ電子共役系の
中に金属イオンが存在するため、電導、光電導、
エネルギー変換、電極、触媒等の材料として、ま
た高分子とブレンドすることにより高度の機能を
有するフイルムや薄膜等の高分子材料などとして
注目され、種々研究が行われている。
これらのフタロシアニン化合物の用途の１つに
光の吸収剤としての役割が挙げられる。
しかし、吸収剤として用いた場合、近赤外およ
び赤外域に吸収がなく、近赤外および赤外域に吸
収をもつたフタロシアニン化合物が要望されてい
る。
発明の目的
本発明の目的は、近赤外および赤外域に吸収を
持つフタロシアニン化合物を提供することにあ
る。
発明の開示
このような目的は、下記の本発明によつて達成
される。
すなわち、本発明は、
式
MX−Pc（−OR）o（Ｙ）16-o
｛式中、Ｍは、Al、GaまたはInを表わす。
Ｘは、ハロゲン原子を表わす。
Pcは、フタロシアニン核を表わす。
Ｒは、炭素原子数１〜20のアルキル基または炭
素原子数６〜24のアリール基もしくはアルコキシ
アリール基を表わす。
Ｙは、水素原子またはハロゲン原子を表わす。
ｎは、５〜16の正の整数を表わす。｝
で示されることを特徴とするフタロシアニン化合
物である。
発明の具体的構成
以下、本発明の具体的構成について詳細に説明
する。
本発明のフタロシアニン化合物は、下記式
（）で示されるものである。
式
MX−Pc（−OR）o（Ｙ）16-o （）
上記式（）において、Ｍは、Al、Ga、Inで
ある。
Ｘはハロゲン原子、例えばＦ、Cl、Br、Ｉ
等；
であり、なかでもCl、Br、Ｉが好ましい。
Pcは下記式（）で表わされるフタロシアニ
ン核である。
式
上記式（）で、−ORもしくはＹが置換する
位置は１〜16のいずれかである。
Ｒは、炭素数１〜20の置換もしくは非置換のア
ルキル基、例えばメチル基、エチル基、プロピル
基、ブチル基、ペンチルヘキシル基、シクロヘキ
シル基、ドデシル基等；炭素数６〜24のアリール
基、例えばフエニル基等；炭素数６〜24のアルコ
キシアリール基、例えばメトキシフエニル基、BACKGROUND OF THE INVENTION Technical Field The present invention relates to phthalocyanine compounds, particularly phthalocyanine compounds having absorption in the near-infrared and infrared regions. Prior art and its problems Phthalocyanine compounds are stable against light, heat, humidity, etc. and have excellent robustness. In particular, metal phthalocyanines are widely used as various dyes and pigments due to their high stability and strong color tone.In addition, metal phthalocyanines are widely used as various dyes and pigments due to their high stability and strong color tone.
It has attracted attention as a material for energy conversion, electrodes, catalysts, etc., and as a polymer material for films and thin films that have advanced functions when blended with polymers, and various studies are being conducted on it. One of the uses of these phthalocyanine compounds is as a light absorber. However, when used as an absorbent, there is a demand for phthalocyanine compounds that do not absorb in the near-infrared and infrared regions but have absorption in the near-infrared and infrared regions. OBJECT OF THE INVENTION An object of the present invention is to provide a phthalocyanine compound having absorption in the near-infrared and infrared regions. DISCLOSURE OF THE INVENTION These objects are achieved by the invention described below. That is, the present invention has the following formula: MX-Pc(-OR) o (Y) 16-o {wherein M represents Al, Ga or In. X represents a halogen atom. Pc represents a phthalocyanine nucleus. R represents an alkyl group having 1 to 20 carbon atoms, an aryl group or an alkoxyaryl group having 6 to 24 carbon atoms. Y represents a hydrogen atom or a halogen atom. n represents a positive integer from 5 to 16. } It is a phthalocyanine compound characterized by the following. Specific Configuration of the Invention The specific configuration of the present invention will be described in detail below. The phthalocyanine compound of the present invention is represented by the following formula (). Formula MX-Pc(-OR) o (Y) 16-o () In the above formula (), M is Al, Ga, or In. X is a halogen atom, such as F, Cl, Br, I
etc.; Among them, Cl, Br, and I are preferable. Pc is a phthalocyanine nucleus represented by the following formula (). formula In the above formula (), the position substituted by -OR or Y is any one of 1 to 16. R is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, such as a methyl group, ethyl group, propyl group, butyl group, pentylhexyl group, cyclohexyl group, dodecyl group, etc.; an aryl group having 6 to 24 carbon atoms; For example, phenyl group; alkoxyaryl group having 6 to 24 carbon atoms, such as methoxyphenyl group,
【式】等；である。
Ｙは、水素原子；
ハロゲン原子、例えばＦ、Cl、Br、Ｉ等；で
あり、なかでもCl、Brが好ましい。
ｎは、５〜16の正の整数を表わし、なかでも８
〜16であることが好ましい。
以下に本発明のフタロシアニン化合物の具体例
を挙げる。
(1) オクタ−（−OCH3）−AlClPc
(2) オクタ−（−OC2H5）−InClPc
(3) オクタ−（[Formula] etc.; Y is a hydrogen atom; a halogen atom, such as F, Cl, Br, I, etc.; of these, Cl and Br are preferred. n represents a positive integer from 5 to 16, especially 8
-16 is preferred. Specific examples of the phthalocyanine compounds of the present invention are listed below. (1) Octa-(-OCH 3 )-AlClPc (2) Octa-(-OC 2 H 5 )-InClPc (3) Octa-(
【式】）−GaClPc (4) オクタ−（−OC3H7）−InBrPc (5) オクタ−（−Ｏ[Formula])−GaClPc (4) Octa−(−OC 3 H 7 )−InBrPc (5) Octa−(−O
【式】） AlClPc (6) デカ−（−Ｏ−C2H5）AlIPc (7) ウンデカ−（−Ｏ[Formula]) AlClPc (6) Deca-(-O-C 2 H 5 )AlIPc (7) Undeca-(-O
【式】） GaBrPc (8) ペンタデカ−（【formula】) GaBrPc (8) Pentadeka (
【式】OCH3） AlClPc (9) ペンタデカ−（[Formula] OCH 3 ) AlClPc (9) Pentadeca (
【式】OC2H5） GaClPc (10) ペンタデカ−（−Ｏ−C2H5）InIPc (11) ペンタデカ−（−Ｏ−C2H5）CaIPc (12) ヘキサデカ−（−Ｏ[Formula] OC 2 H 5 ) GaClPc (10) Pentadeca-(-O-C 2 H 5 ) InIPc (11) Pentadeca-(-O-C 2 H 5 ) CaIPc (12) Hexadeca-(-O
【式】） InClPc (13) ヘキサデカ−（【formula】) InClPc (13) Hexadeca (
【式】）GaClPc
(14) ヘキサデカ−（−Ｏ−C2H5）InBrPc
(15) ヘキサデカ−（−OC3H7）AlClPc
(16) ウンデカ−（−Ｏ−C2H5）InClPc
本発明のフタロシアニン化合物は、一般に次の
スキームに従う方法で合成することができる。
Li2Pc（−OR）16＋nMXY2
アミルアルコール中
―――――――――――→
130℃、1hrMX−Pc（−OR）o（Ｙ）16-o
この方法を用いた場合の反応生成物の精製は次
のように行う。
反応生成物を100℃に冷却し、エタノールで希
釈した後、室温に戻して濾過する。この濾別した
ものをエタノールで洗浄し、さらにエタノール水
溶液で洗浄し、乾燥する。こうして得られた粗生
成物をシリカカラムでトルエンによつて展開し、
分離して精製する。
発明の具体的作用効果
本発明のフタロシアニン化合物は、
MX−Pc（−OR）o（Ｙ）16-o
で示されるものであるため、近赤外および赤外域
に吸収をもつものが得られる。
従つて、きわめて光や熱に対して堅牢性の高い
近赤外、赤外吸収剤が実現し、光記録媒体や電子
写真感光体用等の吸収剤として有用である。
スキーム２
ROH＋KOHキノリン中
―――――――→
140℃、1hrRO-K+
nRO-K+＋MXPc（Ｙ）16
―――――――――――→
160〜180℃、1hrMX−Pc（―OR）o（Ｙ）16-o＋副生成物
精製はスキーム１の場合と同様に行う。
発明の具体的実施例
以下、本発明の具体的実施例を示し、本発明を
さらに詳細に説明する。
実施例 １
例示化合物（14）の合成[Formula]) GaClPc (14) Hexadeca-(-O-C 2 H 5 ) InBrPc (15) Hexadeca-(-OC 3 H 7 ) AlClPc (16) Undeca-(-O-C 2 H 5 ) InClPc This invention The phthalocyanine compound can be generally synthesized by a method according to the following scheme. Li 2 Pc (−OR) 16 +nMXY 2 in amyl alcohol――――――――――→ 130℃, 1hrMX−Pc(−OR) o (Y) 16-o Reaction using this method Purification of the product is carried out as follows. The reaction product is cooled to 100°C, diluted with ethanol, then returned to room temperature and filtered. The filtered product is washed with ethanol, further washed with an aqueous ethanol solution, and dried. The crude product thus obtained was developed with toluene on a silica column,
Separate and purify. Specific Effects of the Invention Since the phthalocyanine compound of the present invention is represented by MX-Pc(-OR) o (Y) 16-o , one having absorption in the near-infrared and infrared regions can be obtained. Therefore, near-infrared and infrared absorbers with extremely high fastness to light and heat have been realized, and are useful as absorbers for optical recording media, electrophotographic photoreceptors, and the like. Scheme 2 ROH+KOH in quinoline――――――――→ 140℃, 1hrRO - K + nRO - K + +MXPc(Y) 16 ――――――――――――→ 160～180℃, 1hrMX−Pc( -OR) o (Y) 16-o + by-product Purification is carried out as in Scheme 1. Specific Examples of the Invention Hereinafter, specific examples of the present invention will be shown and the present invention will be explained in further detail. Example 1 Synthesis of exemplified compound (14)
【式】１モルと、エタノール
（EtOH）４モルとを140℃、２時間で反応させ、
[Formula] 1 mole and 4 moles of ethanol (EtOH) are reacted at 140℃ for 2 hours,
【式】を得た。
この化合物４モルにLi+（OC5H11）-2モルを加え
て150℃で２時間反応させ、Li2Pc（−OEt）16を得
た。さらに、この化合物１モルにInCl31モルを加
えて、アミルアルコール中で130℃で１時間反応
させ、目的物を得た。この反応生成物を100℃に
冷却した後、エタノール（EtOH）で希釈して室
温に戻し、濾過した。濾別したものをEtOHで洗
浄し、さらにEtOH−H2O（１：１）溶液で洗浄
し、乾燥した。このようにして得られた粗生成物
をシリカカラムでトルエンによつて展開し、分
離、精製して目的物を得た。
収率 18.6％
元素分析
Ｃ Ｈ Ｎ In
計算値／％ 54.44 5.67 7.94 8.14
実測値／％ 54.52 5.66 7.91 8.16
吸収極大 λmax
830nｍ（スピンナー塗布により0.1μｍ厚の薄膜
を形成して測定）
実施例 ２
例示化合物(2)の合成
実施例１と同様にして目的物を得た。
収率 23.2％
元素分析
Ｃ Ｈ Ｎ In
計算値／％ 44.66 3.10 8.68 8.90
実測値／％ 43.92 3.11 8.66 8.94
実施例 ３
例示化合物(3)の合成
実施例１と同様にして目的物を得た。
収率 28.4％
元素分析
Ｃ Ｈ Ｎ Ga
計算値／％ 58.94 2.46 6.88 4.28
実測値／％ 57.94 2.47 6.91 4.30
実施例 ４
例示化合物(5)の合成
実施例１と同様にして目的物を得た。
収率 18.6％
元素分析
Ｃ Ｈ Ｎ Ga
計算値／％ 66.25 2.76 5.52 3.44
実測値／％ 65.84 2.72 5.58 3.49
実施例 ５
例示化合物(12)の合成
βナフトール16モルとKOH16モルとをキノリ
ン中で140℃にて１時間反応させた。
これにInClPc（Cl）161モルを加え、160〜180℃
にて１時間反応させた。
得られた反応生成物の精製は実施例１と同様に
行つた。
収率 23.6％
元素分析
Ｃ Ｈ Ｎ In
計算値／％ 78.52 3.82 3.82 3.91
実測値／％ 77.94 3.85 3.88 3.89
吸収極大 λmax
840nｍ（スピンナー塗布により0.1μｍ厚の薄膜
を形成して測定）
実施例 ６
例示化合物(8)の合成
実施例５と同様にして目的物を得た。
収率 28.5％
元素分析
Ｃ Ｈ Ｎ Al
計算値／％ 69.11 1.89 4.71 1.13
実測値／％ 69.25 1.87 4.70 1.13
実施例 ７
例示化合物(4)の合成
実施例５と同様にして目的物を得た。
収率 22.8％
元素分析
Ｃ Ｈ Ｎ In
計算値／％ 37.29 3.10 6.22 6.37
実測値／％ 37.11 3.12 6.21 6.39
実施例 ８
例示化合物（16）の合成
実施例５と同様にして目的物を得た。
収率 29.4％
元素分析
Ｃ Ｈ Ｎ In
計算値／％ 49.15 4.17 8.49 8.71
実測値／％ 48.93 4.19 8.51 8.70I got [formula]. Li + (OC 5 H 11 ) − 2 mol was added to 4 mol of this compound and reacted at 150° C. for 2 hours to obtain Li 2 Pc(−OEt) 16 . Furthermore, 1 mol of InCl 3 was added to 1 mol of this compound, and the mixture was reacted in amyl alcohol at 130° C. for 1 hour to obtain the desired product. The reaction product was cooled to 100°C, diluted with ethanol (EtOH), returned to room temperature, and filtered. The filtered product was washed with EtOH, further washed with EtOH-H 2 O (1:1) solution, and dried. The crude product thus obtained was developed with toluene on a silica column, separated and purified to obtain the desired product. Yield 18.6% Elemental analysis C H N In Calculated value/% 54.44 5.67 7.94 8.14 Actual value/% 54.52 5.66 7.91 8.16 Absorption maximum λmax 830 nm (measured by forming a 0.1 μm thick thin film by spinner coating) Example 2 Exemplary compound Synthesis of (2) The target product was obtained in the same manner as in Example 1. Yield 23.2% Elemental analysis C H N In Calculated value/% 44.66 3.10 8.68 8.90 Actual value/% 43.92 3.11 8.66 8.94 Example 3 Synthesis of exemplified compound (3) The target product was obtained in the same manner as in Example 1. Yield 28.4% Elemental analysis C H N Ga Calculated value/% 58.94 2.46 6.88 4.28 Actual value/% 57.94 2.47 6.91 4.30 Example 4 Synthesis of exemplified compound (5) The target product was obtained in the same manner as in Example 1. Yield 18.6% Elemental analysis C H N Ga Calculated value/% 66.25 2.76 5.52 3.44 Actual value/% 65.84 2.72 5.58 3.49 Example 5 Synthesis of exemplified compound (12) 16 moles of β-naphthol and 16 moles of KOH were mixed in quinoline at 140°C The mixture was reacted for 1 hour. Add 1 mol of InClPc (Cl) 16 to this and heat to 160-180℃.
The mixture was reacted for 1 hour. The obtained reaction product was purified in the same manner as in Example 1. Yield 23.6% Elemental analysis C H N In Calculated value/% 78.52 3.82 3.82 3.91 Actual value/% 77.94 3.85 3.88 3.89 Absorption maximum λmax 840 nm (measured by forming a 0.1 μm thick thin film by spinner coating) Example 6 Exemplary compound Synthesis of (8) The target product was obtained in the same manner as in Example 5. Yield 28.5% Elemental analysis C H N Al Calculated value/% 69.11 1.89 4.71 1.13 Actual value/% 69.25 1.87 4.70 1.13 Example 7 Synthesis of exemplified compound (4) The target product was obtained in the same manner as in Example 5. Yield 22.8% Elemental analysis C H N In Calculated value/% 37.29 3.10 6.22 6.37 Actual value/% 37.11 3.12 6.21 6.39 Example 8 Synthesis of exemplified compound (16) The target product was obtained in the same manner as in Example 5. Yield 29.4% Elemental analysis C H N In Calculated value/% 49.15 4.17 8.49 8.71 Actual value/% 48.93 4.19 8.51 8.70
Claims (1)
素原子数６〜24のアリール基もしくはアルコキシ
アリール基を表わす。 Ｙは、水素原子またはハロゲン原子を表わす。 ｎは、５〜16の正の整数を表わす。｝ で示されることを特徴とするフタロシアニン化合
物。[Claims] 1 Formula MX-Pc(-OR) o (Y) 16-o {wherein M represents Al, Ga or In. X represents a halogen atom. Pc represents a phthalocyanine nucleus. R represents an alkyl group having 1 to 20 carbon atoms, an aryl group or an alkoxyaryl group having 6 to 24 carbon atoms. Y represents a hydrogen atom or a halogen atom. n represents a positive integer from 5 to 16. } A phthalocyanine compound characterized by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27949784A JPS61152689A (en) | 1984-12-26 | 1984-12-26 | Phthalocyanins |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27949784A JPS61152689A (en) | 1984-12-26 | 1984-12-26 | Phthalocyanins |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61152689A JPS61152689A (en) | 1986-07-11 |
| JPH0251558B2 true JPH0251558B2 (en) | 1990-11-07 |
Family
ID=17611869
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP27949784A Granted JPS61152689A (en) | 1984-12-26 | 1984-12-26 | Phthalocyanins |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61152689A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR960013076B1 (en) * | 1987-02-13 | 1996-09-30 | 더 세크 레터리 오브 스테이트 퍼 디펜스 인 허 브리태닉 머제스티스 가번먼트 오브 더 유나이티드 킹덤 오브 그레이트 브리튼 앤드 노던 아일랜드 | Substituted phthalocyanines |
| JPH0631239B2 (en) * | 1987-04-06 | 1994-04-27 | 株式会社日本触媒 | Novel fluorine-containing phthalocyanine compound and method for producing the same |
| US5312706A (en) * | 1992-05-29 | 1994-05-17 | Xerox Corporation | Infra-red photoconductor based on octa-substituted phthalocyanines |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60199890A (en) * | 1984-02-17 | 1985-10-09 | チバ‐ガイギ アクチエンゲゼルシヤフト | Water-soluble phthalocyanine compound and use as optical activator |
-
1984
- 1984-12-26 JP JP27949784A patent/JPS61152689A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60199890A (en) * | 1984-02-17 | 1985-10-09 | チバ‐ガイギ アクチエンゲゼルシヤフト | Water-soluble phthalocyanine compound and use as optical activator |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61152689A (en) | 1986-07-11 |
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| LAPS | Cancellation because of no payment of annual fees |