JPH0730267B2 - Crystalline oxytitanium phthalocyanine and method for producing the same - Google Patents
Crystalline oxytitanium phthalocyanine and method for producing the sameInfo
- Publication number
- JPH0730267B2 JPH0730267B2 JP14344586A JP14344586A JPH0730267B2 JP H0730267 B2 JPH0730267 B2 JP H0730267B2 JP 14344586 A JP14344586 A JP 14344586A JP 14344586 A JP14344586 A JP 14344586A JP H0730267 B2 JPH0730267 B2 JP H0730267B2
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- oxytitanium phthalocyanine
- temperature
- type
- producing
- reaction
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Classifications
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording-members for original recording by exposure, e.g. to light, to heat or to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/0664—Dyes
- G03G5/0696—Phthalocyanines
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- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Photoreceptors In Electrophotography (AREA)
Description
【発明の詳細な説明】 （産業上の利用分野） 本発明は、特定の結晶型のオキシチタニウムフタロシア
ニン及びその製造方法に関するものである。TECHNICAL FIELD The present invention relates to a specific crystal form of oxytitanium phthalocyanine and a method for producing the same.
（従来の技術と発明が解決しようとする問題点） フタロシアニン類は、塗料、印刷インキ、樹脂の着色・
触媒或は電子材料として有用な化合物であり、殊に電子
写真感光体用材料として近年盛んに用いられるようにな
つた。(Problems to be solved by conventional technology and invention) Phthalocyanines are used for coloring paints, printing inks, and resins.
It is a compound useful as a catalyst or an electronic material, and in recent years, it has been actively used especially as a material for an electrophotographic photoreceptor.
本発明者らは、オキシチタニウムフタロシアニンの製造
方法について詳細に検討した結果、製造条件の微妙な違
いによつて３種の結晶型（以下夫々「Ａ型」、「Ｂ型」
及び「Ｃ型」という）が生成することを確認した。夫々
の粉末Ｘ線回折図を図−１、図−２及び図−３に示す。
Ａ型は回折角（２θ）9.3゜、26.3゜に、Ｂ型は7.6゜、
28.6゜に、Ｃ型は7.0゜、15.6゜、23.4゜、25.5゜に夫
々特徴的な回折ピークを有する。As a result of detailed examination of the method for producing oxytitanium phthalocyanine, the present inventors have found that there are three types of crystal forms (hereinafter referred to as “A type” and “B type”, respectively) due to subtle differences in production conditions.
And "type C") are generated. The respective powder X-ray diffraction patterns are shown in FIGS. 1, 2 and 3.
The A type has a diffraction angle (2θ) of 9.3 ° and 26.3 °, the B type has 7.6 °,
At 28.6 °, C type has characteristic diffraction peaks at 7.0 °, 15.6 °, 23.4 °, and 25.5 °.
上記３種の結晶は通常混合物として得られることが多い
が、夫々物性が異なるために、混合物のまま用いると物
性の不安定性に由来する種々のトラブルが起こり易い。
従つて、その製造に際しては純粋な結晶型のオキシチタ
ニウムフタロシアニンを取得するのが望ましいことは言
うまでもない。The above-mentioned three kinds of crystals are usually obtained as a mixture in many cases, but since the physical properties are different from each other, if they are used as a mixture, various troubles due to instability of physical properties are likely to occur.
Therefore, it goes without saying that it is desirable to obtain pure crystalline form of oxytitanium phthalocyanine in the production thereof.
例えば、オキシチタニウムフタロシアニンは、その使用
形態として各種のポリマーや溶媒等に分散させた後、塗
布、乾燥を経て製品化する場合が多い。併しながら、そ
の結晶型の相異によつてポリマーや溶媒等との相互作用
が異なるために、結晶型の異なつたものの混合物を用い
ると、分散性が阻害されたり、物性が不安定になること
が多い。このような欠点を排除するためには、純粋な結
晶型のオキシチタニウムフタロシアニンを製造する必要
があり、その製造法の開発が強く望まれている所以であ
る。For example, oxytitanium phthalocyanine is often used as a form of use after being dispersed in various polymers or solvents, and then applied and dried to be commercialized. At the same time, since the interaction with the polymer, solvent, etc. is different due to the difference in the crystal type, when a mixture of different crystal types is used, the dispersibility is hindered or the physical properties become unstable. Often. In order to eliminate such defects, it is necessary to produce pure crystalline oxytitanium phthalocyanine, which is the reason why development of the production method is strongly desired.
（問題点を解決するための手段） 本発明者らは、純粋なＣ型結晶を得るべく鋭意検討を重
ねた結果、或る特定の条件下ではオキシチタニウムフタ
ロシアニンのＣ型結晶のみが選択的に生成することを見
出し、本発明に到達した。(Means for Solving Problems) The inventors of the present invention have conducted extensive studies to obtain a pure C-type crystal, and as a result, under certain specific conditions, only the C-type crystal of oxytitanium phthalocyanine was selectively formed. The inventors have found that they are produced and have reached the present invention.
すなわち、本発明の要旨は粉末Ｘ線回折スペクトルにお
いて、回折角（２θ±0.2゜）7.0゜、15.6゜、23.4゜、
25.5゜に強い回折ピークを有することを特徴とする結晶
型オキシチタニウムフタロシアニンおよび有機溶媒中、
170〜300℃の温度でｏ−フタロジニトリルと四塩化チタ
ンを縮合し、次いで加水分解してオキシチタニウムフタ
ロシアニンを製造する方法において、縮合後縮合物と有
機溶媒を100℃以下の温度で分離することによつて該オ
キシチタニウムフタロシアニンを得ることを特徴とす
る、オキシチタニウムフタロシアニンの製造方法に存す
る。That is, the gist of the present invention is that in the powder X-ray diffraction spectrum, the diffraction angles (2θ ± 0.2 °) 7.0 °, 15.6 °, 23.4 °,
In crystalline oxytitanium phthalocyanine and an organic solvent, which have a strong diffraction peak at 25.5 °,
In the method of producing oxytitanium phthalocyanine by condensing o-phthalodinitrile and titanium tetrachloride at a temperature of 170 to 300 ° C, the condensate after condensation is separated from the organic solvent at a temperature of 100 ° C or less. Thus, the method for producing oxytitanium phthalocyanine is characterized in that the oxytitanium phthalocyanine is obtained.
以下、本発明を詳細に説明する。Hereinafter, the present invention will be described in detail.
一般的に、オキシチタニウムフタロシアニンは、有機溶
媒中170〜300℃の温度で、ｏ−フタロジニトリルと四塩
化チタンとの縮合反応によつて生成するジクロロチタニ
ウムフタロシアニンを熱時別し、次いで加水分解する
ことによつて製造される。Generally, oxytitanium phthalocyanine is prepared by subjecting dichlorotitanium phthalocyanine produced by the condensation reaction of o-phthalodinitrile and titanium tetrachloride in an organic solvent at a temperature of 170 to 300 ° C., and then hydrolyzing it. It is manufactured by
本発明者らは、上記縮合反応後の縮合物（ジクロロチタ
ニウムフタロシアニン）と反応溶媒の分離条件に着目
し、詳細な検討を行なつた。その結果、両者を分離する
際の温度がオキシチタニウムフタロシアニンの結晶型を
左右する重要な因子であることを見出した。 The present inventors have paid attention to the conditions for separating the condensate (dichlorotitanium phthalocyanine) after the condensation reaction and the reaction solvent, and have made detailed studies. As a result, they have found that the temperature at which they are separated is an important factor that determines the crystal form of oxytitanium phthalocyanine.
即ち、縮合物と反応溶媒の分離を100℃以下の温度で行
なうことにより、純粋なＣ型結晶が選択的且つ容易に得
られることを見出した。該分離温度が100℃以上の場合
は、Ａ型又はＢ型或はそれらの混合物が得られ、本発明
の目的は達成されない。That is, it was found that pure C-type crystals can be selectively and easily obtained by separating the condensate and the reaction solvent at a temperature of 100 ° C. or lower. When the separation temperature is 100 ° C. or higher, type A or type B or a mixture thereof is obtained, and the object of the present invention is not achieved.
縮合物と反応溶媒の分離温度は100℃以下であれば任意
に選択できるが、好ましくは20〜70℃の範囲である。分
離温度が低過ぎると反応液の粘度が高くなり、分離操作
が難かしくなるので避けるのが望ましい。又、分離方法
としては、過法、遠心分離法、沈降法等のいずれも採
用可能である。The separation temperature of the condensate and the reaction solvent can be arbitrarily selected as long as it is 100 ° C or lower, but is preferably in the range of 20 to 70 ° C. If the separation temperature is too low, the viscosity of the reaction solution becomes high and the separation operation becomes difficult, so it is desirable to avoid it. Further, as a separation method, any of an over-method, a centrifugal separation method, a sedimentation method and the like can be adopted.
縮合反応温度は170〜300℃の範囲であれば任意に選択で
きるが、好ましくは170〜250℃の範囲である。反応温度
が低過ぎると反応に長時間を要するので実用的でない。
又、反応温度が高過ぎると、反応溶媒や生成物が分解す
る恐れがあるので、300℃以上の温度は避けるのが望ま
しい。The condensation reaction temperature can be arbitrarily selected as long as it is in the range of 170 to 300 ° C, but is preferably in the range of 170 to 250 ° C. If the reaction temperature is too low, the reaction takes a long time, which is not practical.
Further, if the reaction temperature is too high, the reaction solvent or the product may be decomposed, so it is desirable to avoid a temperature of 300 ° C. or higher.
ｏ−フタロジニトリルと四塩化チタンの仕込モル比は任
意に選択できるが、4:1の仕込モル比が好適である。4:1
以外の仕込モル比でも本発明の目的は達せられるが、収
率の低下、未反応原料の回収等不利な面が多くなるので
避けるのが望ましい。The molar ratio of o-phthalodinitrile and titanium tetrachloride can be arbitrarily selected, but a molar ratio of 4: 1 is preferable. 4: 1
Although the object of the present invention can be achieved with a charging molar ratio other than the above, it is desirable to avoid it because it has many disadvantages such as a decrease in yield and recovery of unreacted raw materials.
縮合反応に用いられる有機溶媒は任意に選択できるが、
沸点が170℃以上のものから選ぶのが好ましい。例えば
α−クロロナフタレン、β−クロロナフタレン、α−ブ
ロモナフタレン、α−メチルナフタレン、α−メトキシ
ナフタレン等のナフタレン類、ジフエニルエーテル、4,
4′−ジクロロジフエニルエーテル、3,3′−ジメチルジ
フエニルエーテル等のジフエニルエーテル類、ジフエニ
ルメタン、4,4′−ジメチルジフエニルメタン、3,3′−
ジクロロジフエニルメタン等のジフエニルメタン類等が
挙げられる。沸点が170℃以下の溶媒、例えばトルエ
ン、クロロベンゼン、エチルベンゼン等を用いることも
できるが、この場合は加圧下で反応する必要があり、反
応装置や操作等が煩雑になるので、上記のような沸点が
170℃以上の有機溶媒が好ましい。The organic solvent used in the condensation reaction can be arbitrarily selected,
It is preferable to select one having a boiling point of 170 ° C. or higher. For example, naphthalene such as α-chloronaphthalene, β-chloronaphthalene, α-bromonaphthalene, α-methylnaphthalene, α-methoxynaphthalene, diphenyl ether, 4,
Diphenyl ethers such as 4'-dichlorodiphenyl ether and 3,3'-dimethyldiphenyl ether, diphenylmethane, 4,4'-dimethyldiphenylmethane, 3,3'-
Examples thereof include diphenylmethanes such as dichlorodiphenylmethane. It is also possible to use a solvent having a boiling point of 170 ° C. or lower, such as toluene, chlorobenzene, and ethylbenzene, but in this case, it is necessary to carry out the reaction under pressure, and the reaction apparatus and operation become complicated, so the boiling point as described above But
An organic solvent of 170 ° C. or higher is preferable.
有機溶媒の使用量は、ｏ−フタロジニトリルに対して２
〜15倍量、好ましくは５〜10倍量から選ばれる。この範
囲より少ないと反応液が粘稠になり、均一な混合撹拌が
困難になる。又、この範囲より多くても反応は順調に進
行するが、単位容積当りの収量が少なくなるので経済的
でない。The amount of the organic solvent used is 2 with respect to o-phthalodinitrile.
It is selected from ˜15 times, preferably 5 to 10 times. If the amount is less than this range, the reaction liquid becomes viscous and uniform mixing and stirring becomes difficult. If the amount is more than this range, the reaction proceeds smoothly, but the yield per unit volume decreases, which is not economical.
ジクロロチタニウムフタロシアニンの加水分解は常法に
従い、過剰量の水を用いて熱水処理によつて行なう。熱
水処理はPH5〜７になるまで繰返して行なうのが好まし
い。更に好ましくは、熱処理後キノリン、α−クロロナ
フタレン、Ｎ−メチルピロリドン等の有機溶剤中で加熱
処理する。この処理はオキシチタニウムフタロシアニン
の結晶化度を高める効果があり、純度の向上にも役立
つ。Hydrolysis of dichlorotitanium phthalocyanine is carried out by hot water treatment using an excess amount of water according to a conventional method. The hot water treatment is preferably repeated until the pH becomes 5 to 7. More preferably, after the heat treatment, heat treatment is carried out in an organic solvent such as quinoline, α-chloronaphthalene, N-methylpyrrolidone. This treatment has the effect of increasing the crystallinity of oxytitanium phthalocyanine and is also useful for improving the purity.
熱水処理温度は任意に選ぶことができるが、好ましくは
50℃以上、更に好ましくは70〜100℃の範囲から選ばれ
る。50℃以下では加水分解速度が小さく、反応の完結に
要する時間が長くなる。又、オキシチタニウムフタロシ
アニンとの親和性を高めるために、C1〜C4の低級アルコ
ールを少量添加するのも有効である。The hot water treatment temperature can be arbitrarily selected, but is preferably
It is selected from the range of 50 ° C or higher, more preferably 70 to 100 ° C. At 50 ° C or lower, the hydrolysis rate is low, and the time required for completion of the reaction is long. It is also effective to add a small amount of a C 1 -C 4 lower alcohol in order to increase the affinity with oxytitanium phthalocyanine.
以下に実施例、比較例、応用例を挙げて本発明を更に具
体的に説明する。Hereinafter, the present invention will be described more specifically with reference to Examples, Comparative Examples, and Application Examples.
実施例１ 温度計、撹拌器、還流冷却器を備えた１の反応フラス
コに、α−クロロナフタレン600ml、ｏ−フタロジニト
リル92g（0.718モル）及び四塩化チタン20ml（0.182モ
ル）を仕込み、撹拌下油浴上で200℃まで昇温した。200
℃で５時間反応した後、50℃まで冷却して過した。得
られたジクロロチタニウムフタロシアニンの湿ケーキを
α−クロロナフタレン400mlで洗浄し、次いでメタノー
ル800mlを加えて撹拌下60℃で２時間懸洗し、ケーキを
別した。更に脱イオン水800mlを加えて90℃に昇温
に、撹拌下同温度で２時間熱懸洗後ケーキを別して
（この操作を２回繰返す）、オキシチタニウムフタロシ
アニンの湿ケーキを得た。Example 1 600 ml of α-chloronaphthalene, 92 g (0.718 mol) of o-phthalodinitrile and 20 ml (0.182 mol) of titanium tetrachloride were charged into a reaction flask 1 equipped with a thermometer, a stirrer, and a reflux condenser, and stirred. The temperature was raised to 200 ° C on a lower oil bath. 200
After reacting at 50 ° C for 5 hours, the mixture was cooled to 50 ° C and passed. The obtained dichlorotitanium phthalocyanine wet cake was washed with 400 ml of α-chloronaphthalene, then 800 ml of methanol was added, and the mixture was washed with stirring at 60 ° C. for 2 hours, and the cake was separated. Further, 800 ml of deionized water was added, the temperature was raised to 90 ° C., and the mixture was hot-suspended under stirring at the same temperature for 2 hours and then the cake was separated (this operation was repeated twice) to obtain a wet cake of oxytitanium phthalocyanine.
次いでこの湿ケーキにＮ−メチルピロリドン700mlを加
えて、撹拌下150℃で２時間懸洗した後、ケーキを別
した（この操作を２回繰返す。）得られた湿ケーキにメ
タノール800mlを加えて、撹拌下60℃で２時間懸洗した
後ケーキを別し、乾燥した結果、精オキシチタニウム
フタロシアニン78g（収率75％）を得た。このものの粉
末Ｘ線回折パターンは図−３に一致し、Ｃ型結晶である
ことが確認された。又、元素分析値は次の通りであつ
た。Then, 700 ml of N-methylpyrrolidone was added to this wet cake, and the suspension was washed with stirring at 150 ° C. for 2 hours, and the cake was separated (this operation is repeated twice). 800 ml of methanol was added to the obtained wet cake. After stirring and stirring at 60 ° C. for 2 hours, the cake was separated and dried to obtain 78 g (yield 75%) of purified oxytitanium phthalocyanine. The powder X-ray diffraction pattern of this product was in agreement with Fig. 3, and it was confirmed to be a C-type crystal. The elemental analysis values are as follows.
Ｃ Ｈ Ｎ Cl 理論値（％） 66.68 2.80 19.44 ０ 実測値（％） 66.51 2.71 19.33 0.58 実施例２〜４ 縮合反応後の過温度及び縮合反応溶媒を変えた以外
は、実施例１と同様に実験した結果を次表に示す。CHNCl theoretical value (%) 66.68 2.80 19.44 0 measured value (%) 66.51 2.71 19.33 0.58 Examples 2 to 4 The same experiment as in Example 1 except that the overtemperature after the condensation reaction and the condensation reaction solvent were changed. The results are shown in the following table.
比 較 例 縮合反応後の過を130℃の温度で行なつた以外は、実
施例１と同様にしてオキシチタニウムフタロシアニンを
製造した。収量は75g、結晶型はＡ型とＢ型の混合物で
あつた。このものの粉末ｘ線回折図を図−４に示す。 Comparative Example An oxytitanium phthalocyanine was produced in the same manner as in Example 1 except that the temperature after the condensation reaction was carried out at a temperature of 130 ° C. The yield was 75 g, and the crystalline form was a mixture of A type and B type. The powder x-ray diffraction pattern of this product is shown in FIG.
応 用 例（電子写真感光体） 実施例１で製造したオキシチタニウムフタロシアニンの
Ｃ型結晶0.4gとポリビニルブチラール0.2gを４−メトキ
シ−４−メチル−２−ペンタノン30gと共にサンドグラ
インダーで分散し、この分散液をポリエステルフイルム
上に蒸着したアルミ蒸着層の上にフイルムアプリケータ
ーにより塗布、乾燥して電荷発生層を形成した。塗布膜
厚は0.3g/m2である。Application Example (Electrophotographic Photoreceptor) 0.4 g of C-type crystals of oxytitanium phthalocyanine prepared in Example 1 and 0.2 g of polyvinyl butyral were dispersed in a sand grinder together with 30 g of 4-methoxy-4-methyl-2-pentanone. The dispersion was applied onto a vapor deposited aluminum layer on a polyester film using a film applicator and dried to form a charge generation layer. The coating film thickness is 0.3 g / m 2 .
この電荷発生層の上に、Ｎ−メチル−３−カルバゾール
カルバルデヒドジフエニルヒドラゾン70部とｐ−ニトロ
ベンゾイルオキシベンザルマロノニトリル２部及びポリ
カーボネート樹脂（三菱化成工業社製ノバレツクス7025
A）100部からなる膜厚17μｍの電荷移動層を積層し、積
層型の感光層を有する電子写真感光体を得た。On this charge generation layer, 70 parts of N-methyl-3-carbazolecarbaldehyde diphenylhydrazone, 2 parts of p-nitrobenzoyloxybenzalmalononitrile and polycarbonate resin (Novarex 7025 manufactured by Mitsubishi Kasei Co., Ltd.)
A) A charge transfer layer consisting of 100 parts and having a film thickness of 17 μm was laminated to obtain an electrophotographic photoreceptor having a laminated type photosensitive layer.
この感光体の感度として半減露光量（E1/2）を静電複写
紙試験装置（川口電機製作所製モデルSP−428）により
測定した。即ち、暗所でコロナ電流が22μＡになるよう
に設定した印加電圧によるコロナ放電により、感光体を
負帯電し、次いで5luxの照度の白色光により露光し、表
面電位が−450Vから225Vに半減するに要する露光量（E1
/2）を求めたところ、1.14lux・secであつた。この時の
感光体の帯電圧（初期の表面電位）は−480V、暗減衰は
41V/sec、露光10秒後の表面電位（残留電位）は−28Vで
あつた。The half-exposure amount (E1 / 2) as the sensitivity of this photoconductor was measured by an electrostatic copying paper test apparatus (Kawaguchi Denki Seisakusho model SP-428). That is, the photoconductor is negatively charged by corona discharge by an applied voltage set so that the corona current becomes 22 μA in the dark, and then exposed to white light with an illuminance of 5 lux, and the surface potential is halved from -450V to 225V. Exposure required for (E1
/ 2) was found to be 1.14 lux · sec. At this time, the charged voltage of the photoconductor (initial surface potential) is -480V, and the dark decay is
The surface potential (residual potential) of 41 V / sec and 10 seconds after exposure was -28 V.
以上の如く、本発明の方法によつて製造したオキシチタ
ニウムフタロシアニンのＣ型結晶は、優れた電子写真特
性を有しており、特に半導体レーザー用感光体として有
用である。As described above, the C-type crystal of oxytitanium phthalocyanine produced by the method of the present invention has excellent electrophotographic characteristics and is particularly useful as a photoconductor for a semiconductor laser.
図−１はオキシチタニウムフタロシアニンのＡ型結晶の
粉末Ｘ線回折図であり、回折角（２θ）9.3゜、26.3゜
に特徴的な強い回折ピークを有する。 図−２はオキシチタニウムフタロシアニンのＢ型結晶の
粉末Ｘ線回折図であり、回折角（２θ）7.6゜、28.6゜
に特徴的な強い回折ピークを有する。 図−３はオキシチタニウムフタロシアニンのＣ型結晶の
粉末Ｘ線回折図であり、回折角（２θ）7.0゜、15.6゜
に特徴的な強い回折ピークを有する。 図−４は比較例で得られたオキシチタニウムフタロシア
ニンの粉末Ｘ線回折図であり、Ａ型結晶とＢ型結晶の混
合物である。回折角（２θ）7.6゜、9.3゜、26.3゜、2
8.6゜に、Ａ型及びＢ型結晶の特徴的な回折ピークを有
する。FIG. 1 is a powder X-ray diffraction pattern of the A-type crystal of oxytitanium phthalocyanine, which has strong diffraction peaks at diffraction angles (2θ) of 9.3 ° and 26.3 °. FIG. 2 is a powder X-ray diffraction pattern of the B-type crystal of oxytitanium phthalocyanine, which has strong diffraction peaks characteristic at diffraction angles (2θ) of 7.6 ° and 28.6 °. FIG. 3 is a powder X-ray diffraction diagram of a C-type crystal of oxytitanium phthalocyanine, which has strong diffraction peaks at diffraction angles (2θ) of 7.0 ° and 15.6 °. FIG. 4 is a powder X-ray diffraction diagram of oxytitanium phthalocyanine obtained in Comparative Example, which is a mixture of A-type crystals and B-type crystals. Diffraction angle (2θ) 7.6 °, 9.3 °, 26.3 °, 2
At 8.6 °, there are characteristic diffraction peaks of the A-type and B-type crystals.
Claims (2)
（２θ±0.2゜）7.0゜、15.6゜、23.4゜、25.5゜に強い
回折ピークを有することを特徴とする結晶型オキシチタ
ニウムフタロシアニン。1. A crystalline oxytitanium phthalocyanine having strong diffraction peaks at diffraction angles (2θ ± 0.2 °) of 7.0 °, 15.6 °, 23.4 ° and 25.5 ° in a powder X-ray diffraction spectrum.
ロジニトリルと四塩化チタンを縮合し、次いて加水分解
してオキシチタニウムフタロシアニンを製造する方法に
おいて、縮合後縮合物と有機溶媒を100℃以下の温度で
分離することによつて、粉末Ｘ線回折スペクトルにおい
て、回折角（２θ±0.2゜）7.0゜、15.6゜、23.4゜、2
5.5゜に強い回折ピークを有するオキシチタニウムフタ
ロシアニンを得ることを特徴とする、オキシチタニウム
フタロシアニンの製造方法。2. A method of condensing o-phthalodinitrile and titanium tetrachloride in an organic solvent at a temperature of 170 to 300 ° C. and then hydrolyzing to produce oxytitanium phthalocyanine, which comprises a condensation product after condensation and an organic compound. By separating the solvent at a temperature of 100 ° C. or lower, the diffraction angles (2θ ± 0.2 °) of 7.0 °, 15.6 °, 23.4 °, 2
A method for producing oxytitanium phthalocyanine, which comprises obtaining oxytitanium phthalocyanine having a strong diffraction peak at 5.5 °.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14344586A JPH0730267B2 (en) | 1986-06-19 | 1986-06-19 | Crystalline oxytitanium phthalocyanine and method for producing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14344586A JPH0730267B2 (en) | 1986-06-19 | 1986-06-19 | Crystalline oxytitanium phthalocyanine and method for producing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63366A JPS63366A (en) | 1988-01-05 |
| JPH0730267B2 true JPH0730267B2 (en) | 1995-04-05 |
Family
ID=15338863
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14344586A Expired - Fee Related JPH0730267B2 (en) | 1986-06-19 | 1986-06-19 | Crystalline oxytitanium phthalocyanine and method for producing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0730267B2 (en) |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6322940B1 (en) | 1999-01-08 | 2001-11-27 | Sharp Kabushiki Kaisha | Electrophotographic photoreceptor and electrophotographic image forming process |
| US6291120B1 (en) | 1999-05-14 | 2001-09-18 | Sharp Kabushiki Kaisha | Electrophotographic photoreceptor and coating composition for charge generating layer |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63366A (en) | 1988-01-05 |
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