JPS5941363A - 新規ピリリウム系染料およびその製造方法 - Google Patents
新規ピリリウム系染料およびその製造方法Info
- Publication number
- JPS5941363A JPS5941363A JP57150024A JP15002482A JPS5941363A JP S5941363 A JPS5941363 A JP S5941363A JP 57150024 A JP57150024 A JP 57150024A JP 15002482 A JP15002482 A JP 15002482A JP S5941363 A JPS5941363 A JP S5941363A
- Authority
- JP
- Japan
- Prior art keywords
- dye
- formula
- general formula
- thiopyrylium
- methyl
- 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.)
- Granted
Links
- OKYDCMQQLGECPI-UHFFFAOYSA-N thiopyrylium Chemical compound C1=CC=[S+]C=C1 OKYDCMQQLGECPI-UHFFFAOYSA-N 0.000 title claims abstract description 12
- 238000002360 preparation method Methods 0.000 title description 2
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical compound C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 title description 2
- 150000001450 anions Chemical class 0.000 claims abstract description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract description 12
- 239000002904 solvent Substances 0.000 abstract description 5
- 238000000576 coating method Methods 0.000 abstract description 4
- 239000004065 semiconductor Substances 0.000 abstract description 4
- 239000011248 coating agent Substances 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 238000000034 method Methods 0.000 abstract description 2
- 230000003287 optical effect Effects 0.000 abstract description 2
- IBDCHGJXDLAGGO-UHFFFAOYSA-M 4-methyl-2,6-diphenylpyrylium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.C=1C(C)=CC(C=2C=CC=CC=2)=[O+]C=1C1=CC=CC=C1 IBDCHGJXDLAGGO-UHFFFAOYSA-M 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000000975 dye Substances 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
- 238000000862 absorption spectrum Methods 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- -1 fluoroborate Chemical compound 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
- 229960000583 acetic acid Drugs 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- ADPBOZWKPHDQAF-UHFFFAOYSA-N 2-methyl-4,6-diphenylthiopyrylium Chemical compound [S+]=1C(C)=CC(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 ADPBOZWKPHDQAF-UHFFFAOYSA-N 0.000 description 1
- BBIFSSHXMKXRCB-UHFFFAOYSA-N 4-methyl-2,6-diphenylthiopyrylium Chemical compound C=1C(C)=CC(C=2C=CC=CC=2)=[S+]C=1C1=CC=CC=C1 BBIFSSHXMKXRCB-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- OOYGSFOGFJDDHP-KMCOLRRFSA-N kanamycin A sulfate Chemical group OS(O)(=O)=O.O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N OOYGSFOGFJDDHP-KMCOLRRFSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002893 slag Substances 0.000 description 1
- AGGIJOLULBJGTQ-UHFFFAOYSA-N sulfoacetic acid Chemical compound OC(=O)CS(O)(=O)=O AGGIJOLULBJGTQ-UHFFFAOYSA-N 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
Abstract
(57)【要約】本公報は電子出願前の出願データであるた
め要約のデータは記録されません。
め要約のデータは記録されません。
Description
【発明の詳細な説明】
本発明は新規なビリリウム染料、チオピリリウム染料お
よびその製造方法に関するものである。
よびその製造方法に関するものである。
本発明による染料は下記一般式（１）および一般式（２
）で示される。
）で示される。
（式中Ｘは酸素原子または硫黄原子を表わし、Ｒはメチ
ル基またはエチル基を表わし、２θはアニオンを表わす
。） 本発明のビリリウム染料またれチオピリリウム染料は下
記一般式（３）および一般式（４）で示されるピリリウ
ム塩、またはチオピリリウム塩（式中、Ｘは酸素原子ま
たは硫黄原子を表わし、ｚｅはパークロｔ／−ト、フル
オボレート、スルフオアセテートなどのアニオンを表わ
す。）と下記一般式（５）で表わされる、４−７オルば
ルー ４’−Ｎ、Ｎ−ジアルキルアミノスチルベン（式
中、Ｒはメチル基またはエチル基を表わす。）とを溶媒
中で反応させることによって容易に得ることができる。
ル基またはエチル基を表わし、２θはアニオンを表わす
。） 本発明のビリリウム染料またれチオピリリウム染料は下
記一般式（３）および一般式（４）で示されるピリリウ
ム塩、またはチオピリリウム塩（式中、Ｘは酸素原子ま
たは硫黄原子を表わし、ｚｅはパークロｔ／−ト、フル
オボレート、スルフオアセテートなどのアニオンを表わ
す。）と下記一般式（５）で表わされる、４−７オルば
ルー ４’−Ｎ、Ｎ−ジアルキルアミノスチルベン（式
中、Ｒはメチル基またはエチル基を表わす。）とを溶媒
中で反応させることによって容易に得ることができる。
溶媒としては広範な有機溶媒を使用することができるが
とくにエタノールなどのアルコール類、アセトニトリル
などのニトリル類、メチルエチルケト７などのケトン類
、ニトロベンゼンなどのニトロ化合物類、テトラクロロ
エタンなどのハロゲン化炭化水素類無水酢酸などの酸無
水物類などがよい。また反応の促進のために塩基類を加
えることが出来る。具体的にはピペリジン、トリエテル
アばン、ヘキシルアずン、ピリジン、キノリンなどの塩
基をあげることが出来る。
とくにエタノールなどのアルコール類、アセトニトリル
などのニトリル類、メチルエチルケト７などのケトン類
、ニトロベンゼンなどのニトロ化合物類、テトラクロロ
エタンなどのハロゲン化炭化水素類無水酢酸などの酸無
水物類などがよい。また反応の促進のために塩基類を加
えることが出来る。具体的にはピペリジン、トリエテル
アばン、ヘキシルアずン、ピリジン、キノリンなどの塩
基をあげることが出来る。
反応系における原別比合物の割合は一般式（３）又は一
般式（４）で示されるビＩＪ ＩＪウム塩またはチオピ
リリウム塩１モルに対して一般式（５）で示される４−
フォルずルー４’−Ｎ、Ｎ−ジアルキルアずノスナルベ
ンを０．５から１０モル、好ましくは１から２モル使用
する。
般式（４）で示されるビＩＪ ＩＪウム塩またはチオピ
リリウム塩１モルに対して一般式（５）で示される４−
フォルずルー４’−Ｎ、Ｎ−ジアルキルアずノスナルベ
ンを０．５から１０モル、好ましくは１から２モル使用
する。
反応温度は、５０℃付近から溶媒または塩基類の還流温
度で行なわれる。反応時間は１分から１０時間、好まし
くは５分から２時間である。
度で行なわれる。反応時間は１分から１０時間、好まし
くは５分から２時間である。
本発明によるビリリウム染料またはチオピリリウム染料
は６０ＯＩＩＩｌｌ付近から９００ｍ付近までに吸収を
有しておシ、半導体レーザーを用いた電子写真方式ブリ
／ターの電子写真感光被膜、半導体レーザーによる書込
みと再生が可能な光ディスク用禎膜あるいは赤外線カッ
トフィルターなどへの適用が期待される。
は６０ＯＩＩＩｌｌ付近から９００ｍ付近までに吸収を
有しておシ、半導体レーザーを用いた電子写真方式ブリ
／ターの電子写真感光被膜、半導体レーザーによる書込
みと再生が可能な光ディスク用禎膜あるいは赤外線カッ
トフィルターなどへの適用が期待される。
次に本発明のビリリウム染料またはチオピリリウム染料
の製造の念めの実施例を示す。
の製造の念めの実施例を示す。
実施例 １
ビリリウム染料（染料Ａ Ｉ ）の製法。
三ツロフラスコに４−メチル−２，６−シフエニルビリ
リウムパークロレート４゜Ｏ２，４−フォルミルー４’
−Ｎ、Ｎ−ジメチルアずノスチルベン６．０２そして無
水酢酸６０＋ＦＪを仕込み加熱攪拌し、１６０℃で５分
間反応させる。放冷後析出した結晶を戸別し氷酢酸５０
ｍで洗浄しさらにメタノール５０ｍ／で洗浄した後乾燥
し染料５．５２を得た。
リウムパークロレート４゜Ｏ２，４−フォルミルー４’
−Ｎ、Ｎ−ジメチルアずノスチルベン６．０２そして無
水酢酸６０＋ＦＪを仕込み加熱攪拌し、１６０℃で５分
間反応させる。放冷後析出した結晶を戸別し氷酢酸５０
ｍで洗浄しさらにメタノール５０ｍ／で洗浄した後乾燥
し染料５．５２を得た。
収率：８２．２％
、分がト点：２０９〜２１１℃
溶液吸収スはクトル；λｍａｘ”” ７３９ｎｍ （ジ
クロルメタン＃液） ！ ＝ １．４５Ｘ１０５ 赤外線吸収スペクトル： １６４０，１５８０，１５２
０，１４９４゜１１７０ 、１ （１９５（ｃＩｎ−１
）元素分析： ｃ３５Ｈ３ｏｃｚＮｏ５ 計′！Ａ−蝕 分析飴 ｏ ７２．４６ ７２．３７ Ｈ５，２２５，３Ｏ Ｎ ２．４２ ２．３９ 実施例 ２ チオピリリウム染料（染料Ａ２）の製法三ツロフラスコ
に４−メチル−２，６−ジフェニルチオピリリウムバー
クロレート１．２Ｍ’、４−フォルミルー４’−Ｎ、Ｎ
−ジェチルアーミノスチルベン０．９３ ｔそして無水
酢１１１５−を仕込み、加熱攪拌し１００〜１２０℃で
５分間反応させた。
クロルメタン＃液） ！ ＝ １．４５Ｘ１０５ 赤外線吸収スペクトル： １６４０，１５８０，１５２
０，１４９４゜１１７０ 、１ （１９５（ｃＩｎ−１
）元素分析： ｃ３５Ｈ３ｏｃｚＮｏ５ 計′！Ａ−蝕 分析飴 ｏ ７２．４６ ７２．３７ Ｈ５，２２５，３Ｏ Ｎ ２．４２ ２．３９ 実施例 ２ チオピリリウム染料（染料Ａ２）の製法三ツロフラスコ
に４−メチル−２，６−ジフェニルチオピリリウムバー
クロレート１．２Ｍ’、４−フォルミルー４’−Ｎ、Ｎ
−ジェチルアーミノスチルベン０．９３ ｔそして無水
酢１１１５−を仕込み、加熱攪拌し１００〜１２０℃で
５分間反応させた。
放冷後析出した結晶を戸別し氷酢酸５−、メタノール１
０＃＋７！で順次洗浄後乾燥し染料１．１ｆを得た。
０＃＋７！で順次洗浄後乾燥し染料１．１ｆを得た。
収率： ５３．４％
分解点：２０５〜２０６℃
溶液吸収スペクトル：λｍａｘ”” ７８４ ｎｍε−
１，２３ｘ１０”（ジクロルメ タン溶液） 赤外吸収スペクトル： １６３８．１６０５，１５１０
．１４８５゜１１７［）、１１４５．１１０５．１０７
０（ｃＩｎ−１） 元素分析： ０５７Ｊ４０ｔ）ＪＯ４８計算値 分析
値 Ｃ７１，１９７１，１４ Ｈ’５．５０ ５．６１ Ｎ ２．２４ ２．１８ Ｓ ５．１４ ５．１０ 実施例 ６ チオピリリウム染料（染料黒６）の製法三ツロフラスコ
に２−メチル−４，６−ジフェニルチオピリリウムバー
クロレート２．０ｆ％４−フォルイルー４’−Ｎ、Ｎ−
ジエチルアミノスチ ４．（ルベン０．１５Ｆ、そし
て無水酢酸ＡＣＪｍｅを仕込み加熱攪拌し１２５〜１３
０℃で５分間反応させた。 滓放冷後イソプロピルエ
ーテル４０ ｍｌを加え、 り析出物をＰ別イソゾ
ロビルエーテル２０ｒｒｔ、工 ２チルアルコール
２０ ｍｌで順次読ＰＰ後乾燥し、染料１．４４ Ｆを
得た。
１，２３ｘ１０”（ジクロルメ タン溶液） 赤外吸収スペクトル： １６３８．１６０５，１５１０
．１４８５゜１１７［）、１１４５．１１０５．１０７
０（ｃＩｎ−１） 元素分析： ０５７Ｊ４０ｔ）ＪＯ４８計算値 分析
値 Ｃ７１，１９７１，１４ Ｈ’５．５０ ５．６１ Ｎ ２．２４ ２．１８ Ｓ ５．１４ ５．１０ 実施例 ６ チオピリリウム染料（染料黒６）の製法三ツロフラスコ
に２−メチル−４，６−ジフェニルチオピリリウムバー
クロレート２．０ｆ％４−フォルイルー４’−Ｎ、Ｎ−
ジエチルアミノスチ ４．（ルベン０．１５Ｆ、そし
て無水酢酸ＡＣＪｍｅを仕込み加熱攪拌し１２５〜１３
０℃で５分間反応させた。 滓放冷後イソプロピルエ
ーテル４０ ｍｌを加え、 り析出物をＰ別イソゾ
ロビルエーテル２０ｒｒｔ、工 ２チルアルコール
２０ ｍｌで順次読ＰＰ後乾燥し、染料１．４４ Ｆを
得た。
収率：４２％
分解点：２２１〜２２４℃
溶液吸収スペクトル：石ｎａｘ” ７６８ ｎｍｇ＝８
．５Ｘ１０ ’ （ジクロルメ タン溶液） 赤外吸収スはクトル： １６１５，１６００，１５００
．１４７５゜１２７０．１１０５（釧−１） 元素分析： ０５７Ｈ５４０ｔＮＯ４Ｓ計算値 分析
値 ０ ７１．１９ ７１．０２ Ｈ５，５０５，６７ Ｎ ２．２４ ２．０９ ８ ５．１４ ５．１６
．５Ｘ１０ ’ （ジクロルメ タン溶液） 赤外吸収スはクトル： １６１５，１６００，１５００
．１４７５゜１２７０．１１０５（釧−１） 元素分析： ０５７Ｈ５４０ｔＮＯ４Ｓ計算値 分析
値 ０ ７１．１９ ７１．０２ Ｈ５，５０５，６７ Ｎ ２．２４ ２．０９ ８ ５．１４ ５．１６
第１図、第２図および第５図は染料Ａ１、染斗Ａ２およ
び染料Ａ３のジクロルメタン溶液で）可親、赤外吸収ス
はクトルを示す説明図であ０ 特許出願人 キャノン株式会社 代理人ｆＰ埋士狩 野 有 適長（ｎｍ） うｉ長（ｎｍ） 第 ３ 図 遁ｔ（ｎｍ）
び染料Ａ３のジクロルメタン溶液で）可親、赤外吸収ス
はクトルを示す説明図であ０ 特許出願人 キャノン株式会社 代理人ｆＰ埋士狩 野 有 適長（ｎｍ） うｉ長（ｎｍ） 第 ３ 図 遁ｔ（ｎｍ）
Claims (1)
- 【特許請求の範囲】 １）下記一般式（１）または一般式（２）で示されるビ
リリウム染料またはチオピリリウム染料。 （式中Ｘは酸素原子、または硫黄原子を表わし、Ｒはメ
チル基またはエチル基を表わし、ｚｏはアニオンを表わ
す。） ２）下記一般式（３）または一般式（４１で示されるビ
リリウム塩またはチオピリリウム塩 ６Ｈ５ （式中Ｘは酸素原子または硫黄原子を表わしｚｅＦｉア
ニオンを表わす。） と下記一般式（５）で示めされる４−フォルずルー ４
’−Ｎ、Ｎ−ジアルキルアぐノスチルベン（式中Ｒはメ
チル基またはエチル基を表わす。）とを反応させること
を特徴とする下記一般式（１）または一般式（２）で表
わされるビリリウム染料またはテオピＩＪ ＩＪウム染
料の製造方法。 （式中Ｘは酸素原子、または硫黄原子を表わし、Ｒはメ
チル基またはエチル基を表わし、ｚｏはアニオンを表わ
す。）
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57150024A JPS5941363A (ja) | 1982-08-31 | 1982-08-31 | 新規ピリリウム系染料およびその製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57150024A JPS5941363A (ja) | 1982-08-31 | 1982-08-31 | 新規ピリリウム系染料およびその製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5941363A true JPS5941363A (ja) | 1984-03-07 |
| JPH0413384B2 JPH0413384B2 (ja) | 1992-03-09 |
Family
ID=15487821
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57150024A Granted JPS5941363A (ja) | 1982-08-31 | 1982-08-31 | 新規ピリリウム系染料およびその製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5941363A (ja) |
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| Publication number | Publication date |
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| JPH0413384B2 (ja) | 1992-03-09 |
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