JPH0350793B2 - - Google Patents
Info
- Publication number
- JPH0350793B2 JPH0350793B2 JP20001383A JP20001383A JPH0350793B2 JP H0350793 B2 JPH0350793 B2 JP H0350793B2 JP 20001383 A JP20001383 A JP 20001383A JP 20001383 A JP20001383 A JP 20001383A JP H0350793 B2 JPH0350793 B2 JP H0350793B2
- Authority
- JP
- Japan
- Prior art keywords
- parts
- present
- pyrazoloindazolone
- general formula
- phenyl group
- 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
Links
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- 238000006356 dehydrogenation reaction Methods 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 5
- 239000007800 oxidant agent Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000005452 bending Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000004800 polyvinyl chloride Substances 0.000 description 3
- 229920000915 polyvinyl chloride Polymers 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- -1 aromatic nitro compounds Chemical class 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- PBBXJBOFMIHTSC-UHFFFAOYSA-N 1,6-dioxecane-2,5,7,10-tetrone Chemical compound O=C1CCC(=O)OC(=O)CCC(=O)O1 PBBXJBOFMIHTSC-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- AFPHTEQTJZKQAQ-UHFFFAOYSA-N 3-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC([N+]([O-])=O)=C1 AFPHTEQTJZKQAQ-UHFFFAOYSA-N 0.000 description 1
- RTZZCYNQPHTPPL-UHFFFAOYSA-N 3-nitrophenol Chemical compound OC1=CC=CC([N+]([O-])=O)=C1 RTZZCYNQPHTPPL-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 235000005811 Viola adunca Nutrition 0.000 description 1
- 240000009038 Viola odorata Species 0.000 description 1
- 235000013487 Viola odorata Nutrition 0.000 description 1
- 235000002254 Viola papilionacea Nutrition 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 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 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- KSKWGMNRWCYVAT-UHFFFAOYSA-N diethyl 2,5-dioxocyclohexane-1,4-dicarboxylate Chemical compound CCOC(=O)C1CC(=O)C(C(=O)OCC)CC1=O KSKWGMNRWCYVAT-UHFFFAOYSA-N 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- 150000004031 phenylhydrazines Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- LJRGBERXYNQPJI-UHFFFAOYSA-M sodium;3-nitrobenzenesulfonate Chemical compound [Na+].[O-][N+](=O)C1=CC=CC(S([O-])(=O)=O)=C1 LJRGBERXYNQPJI-UHFFFAOYSA-M 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
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Description
【発明の詳細な説明】
本発明は、ピラゾロインダゾロン系色素及びそ
の製造法に関するものである。即ち、本発明は一
般式
で表されるピラゾロインダゾロン系色素を提供す
るものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a pyrazoloindazolone dye and a method for producing the same. That is, the present invention is based on the general formula The present invention provides a pyrazoloindazolone dye represented by:
本発明の化合物は青色〜紫色結晶で、プラスチ
ツクスの着色や液晶用色素として有用な物質であ
る。 The compound of the present invention has blue to purple crystals and is a substance useful for coloring plastics and as a pigment for liquid crystals.
本発明はまた一般式
で表されるピラゾロインダゾロン誘導体を脱水素
酸化して、一般式
で表されるピラゾロインダゾロン系色素の製造法
を提供するものである。 The invention also relates to the general formula By dehydrogenating and oxidizing the pyrazoloindazolone derivative represented by the general formula The present invention provides a method for producing a pyrazoloindazolone dye represented by:
本発明の出発物質であるピラゾロインダゾロン
誘導体（以下、化合物とする）は新規な物質で
あり、このものは、サクシニルコハク酸エステル
とフエニルヒドラジン類とを酸触媒の存在下に加
熱することによつて容易に製造することができ
る。 The pyrazoloindazolone derivative (hereinafter referred to as a compound), which is the starting material of the present invention, is a new substance, which can be obtained by heating succinyl succinate and phenylhydrazines in the presence of an acid catalyst. It can be easily manufactured by
本発明の酸化反応で用いられる溶媒は特に限定
を必要としないが、メタノール、エタノール、プ
ロパノールなどのアルコール類、エチレングリコ
ール、ジエチレングリコール、メチルセロソル
ブ、エチルセロソルブなどの二価アルコール又は
その誘導体、Ｎ−メチル−２−ピロリドン、ジメ
チルスルホキシド、ジメチルホルムアミド、ジオ
キサンなどの極性の強い有機溶媒が好ましい。こ
れらの有機溶媒の使用量は通常出発物質の５〜20
重量倍、好ましくは７〜10重量倍である。 The solvent used in the oxidation reaction of the present invention is not particularly limited, but includes alcohols such as methanol, ethanol, and propanol, dihydric alcohols or derivatives thereof such as ethylene glycol, diethylene glycol, methyl cellosolve, and ethyl cellosolve, N-methyl Strongly polar organic solvents such as -2-pyrrolidone, dimethylsulfoxide, dimethylformamide, and dioxane are preferred. The amount of these organic solvents used is usually 5 to 20% of the starting material.
weight, preferably 7 to 10 times.
酸化剤としては、ニトロベンゼン、ｍ−ニトロ
ベンゼンスルホン酸ナトリウム、ｍ−ニトロフエ
ノール、ｍ−ニトロ安息香酸などの芳香族ニトロ
化合物、ベンゾキノン、アントラキノン、アント
ラキノンスルホン酸ナトリウム、クロラニルなど
のキノン類及びヨウ素などのような比較的温和な
酸化剤が好ましい。また、上記有機溶媒中で単に
空気を導入することによつても実施することがで
きる。酸化剤の使用量は出発物質１モルに対して
１〜２モル使用するのが好ましい。 Examples of oxidizing agents include aromatic nitro compounds such as nitrobenzene, sodium m-nitrobenzenesulfonate, m-nitrophenol, and m-nitrobenzoic acid, quinones such as benzoquinone, anthraquinone, sodium anthraquinonesulfonate, chloranil, and iodine. A relatively mild oxidizing agent is preferred. It can also be carried out simply by introducing air into the organic solvent. The amount of the oxidizing agent used is preferably 1 to 2 moles per mole of the starting material.
本発明の酸化反応は、上記有機溶媒中、空気又
は酸化剤の存在下に、必要があれば触媒量のアル
カリを添加し、50〜200℃、好ましくは60〜150℃
に加熱することにより行われる。 The oxidation reaction of the present invention is carried out in the above organic solvent in the presence of air or an oxidizing agent, with the addition of a catalytic amount of alkali if necessary, at a temperature of 50 to 200°C, preferably 60 to 150°C.
This is done by heating to .
反応時間は反応温度、使用する有機溶媒や酸化
剤などの相違によつて多少異なるが、通常は30分
から４時間位いが適当である。 The reaction time varies somewhat depending on the reaction temperature, the organic solvent used, the oxidizing agent, etc., but is usually about 30 minutes to 4 hours.
本発明により得られる化合物（）は青紫色結
晶で、融点は300℃以下であり、有機溶媒に溶け
て鮮明な青紫色を呈する。 The compound () obtained by the present invention is a blue-violet crystal, has a melting point of 300°C or less, and exhibits a clear blue-purple color when dissolved in an organic solvent.
ポリ塩化ビニル、ポリエチレン、ポリスチレン
などの熱可塑性プラスチツクの染色に用いると耐
候性、耐熱性に優れた着色物を与える。 When used to dye thermoplastics such as polyvinyl chloride, polyethylene, and polystyrene, it provides colored products with excellent weather resistance and heat resistance.
次に、本発明を実施例により説明するが、本発
明はこれらによつて限定されるものではない。 Next, the present invention will be explained with reference to Examples, but the present invention is not limited thereto.
実施例中、単に部とあるのは重量部を示す。 In the examples, parts simply indicate parts by weight.
原料製造例
サクシニルコハク酸ジエチルエステル25.6部、
フエニルヒドラジン32.4部、トルエン300部及び
36％塩酸0.5部を窒素気流中で４時間還流させた。
冷却後、生成した白色結晶を取し、アセトン、
水の順で洗浄したのち、60℃で乾燥した。４，８
−ジヒドロ−２，６−ジフエニル−1H，5H−ピ
ラゾロ〔5.4−ｆ〕インダゾール−３，７−ジオ
ンが15部得られた。Raw material production example 25.6 parts of succinyl succinic acid diethyl ester,
32.4 parts of phenylhydrazine, 300 parts of toluene and
0.5 part of 36% hydrochloric acid was refluxed for 4 hours in a nitrogen stream.
After cooling, remove the white crystals and add acetone,
After washing with water, it was dried at 60°C. 4,8
15 parts of -dihydro-2,6-diphenyl-1H,5H-pyrazolo[5.4-f]indazole-3,7-dione were obtained.
元素分析値： C69.3 H4.7 N16.7 ％
C20H16N4O2としての計算値：
C69.77H4.65N16.28％
IR（KBr、cm-1）：
3450（NH）、2890（CH2）、3050（フエニル基
Ｈ）、1640（Ｃ＝Ｏ）、1600、1490（フエニル基）、
1300（Ｃ−Ｎ）、745、690（−置換ベンゼン面外変
角振動）
1H−NMR（DMSO−d6溶媒δ）：
1.58（−CH2−）、7.8〜8.1（フエニル基）
実施例 １
４，８−ジヒドロ−２，６−ジフエニル−1H，
5H−ピラゾロ〔５，４−ｆ〕インタゾール−３，
７−ジオン10部とクロラニル５部とを氷酢酸100
部中で１時間還流させた。生成した青紫色結晶を
取し、水及びエタノールで洗浄したのち、60℃
で乾燥した。２，６−ジフエニル−1H，5Hピラ
ゾロ〔５，４−ｆ〕インタゾール−３，７−ジオ
ンが9.8部得られた。Elemental analysis value: C69.3 H4.7 N16.7 % Calculated value as C 20 H 16 N 4 O 2 :
C69.77H4.65N16.28% IR (KBr, cm -1 ): 3450 (NH), 2890 (CH 2 ), 3050 (phenyl group H), 1640 (C=O), 1600, 1490 (phenyl group),
1300 (C-N), 745, 690 (-substituted benzene out-of-plane bending vibration) 1 H-NMR (DMSO-d 6 solvent δ): 1.58 (-CH 2 -), 7.8-8.1 (phenyl group) Examples 1 4,8-dihydro-2,6-diphenyl-1H,
5H-pyrazolo[5,4-f]intazole-3,
Add 10 parts of 7-dione and 5 parts of chloranil to 100 parts of glacial acetic acid.
The mixture was refluxed for 1 hour in a vacuum chamber. The generated blue-purple crystals were collected, washed with water and ethanol, and then heated at 60°C.
It was dried. 9.8 parts of 2,6-diphenyl-1H,5H pyrazolo[5,4-f]intazole-3,7-dione were obtained.
元素分析値： C68.79H3.80N16.81％
C20H14N4O2としての計算値：
C70.18H4.09N16.37％
IR（KBr／cm-1）：
3400（NH）、3050（フエニル基Ｈ）、1700（Ｃ＝
Ｏ）、1600、1490（フエニル基Ｃ）、820（１，２，
４，５置換面外変角振動）、770、715（モノ置換面
外変角振動）
1H−NMR（DMSO−d6、δ）：
7.8〜8.2（フエニル基）
使用例 １
実施例１で得られた本発明の化合物0.02部を
DOP100部に溶解し、ポリ塩化ビニル200部を加
え、150℃のロールで５分間混練した。青色で鮮
明な透明塩ビシートが得られた。このシートは耐
熱性及び耐候性に優れていた。Elemental analysis value: C68.79H3.80N16.81% Calculated value as C20H14N4O2 :
C70.18H4.09N16.37% IR (KBr/cm -1 ): 3400 (NH), 3050 (phenyl group H), 1700 (C=
O), 1600, 1490 (phenyl group C), 820 (1, 2,
4,5-substituted out-of-plane bending vibration), 770, 715 (mono-substituted out-of-plane bending vibration) 1 H-NMR (DMSO-d 6 , δ): 7.8-8.2 (phenyl group) Usage example 1 In Example 1 0.02 part of the obtained compound of the present invention
It was dissolved in 100 parts of DOP, 200 parts of polyvinyl chloride was added, and the mixture was kneaded for 5 minutes with a roll at 150°C. A transparent PVC sheet with a clear blue color was obtained. This sheet had excellent heat resistance and weather resistance.
Claims (1)
酸化することを特徴とする一般式 で表されるピラゾロインダゾロン系色素の製造
法。[Claims] 1. General formula A pyrazoloindazolone dye represented by 2 General formula A general formula characterized by dehydrogenation and oxidation of a pyrazoloindazolone derivative represented by A method for producing a pyrazoloindazolone dye represented by
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20001383A JPS6092356A (en) | 1983-10-27 | 1983-10-27 | Pyrazoloindazolone dye and production thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20001383A JPS6092356A (en) | 1983-10-27 | 1983-10-27 | Pyrazoloindazolone dye and production thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6092356A JPS6092356A (en) | 1985-05-23 |
| JPH0350793B2 true JPH0350793B2 (en) | 1991-08-02 |
Family
ID=16417342
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP20001383A Granted JPS6092356A (en) | 1983-10-27 | 1983-10-27 | Pyrazoloindazolone dye and production thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6092356A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015123193A1 (en) | 2014-02-12 | 2015-08-20 | E. I. Du Pont De Nemours And Company | Fungicidal benzodipyrazoles |
-
1983
- 1983-10-27 JP JP20001383A patent/JPS6092356A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6092356A (en) | 1985-05-23 |
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