JPH0270760A - Leuco dye compound - Google Patents
Leuco dye compoundInfo
- Publication number
- JPH0270760A JPH0270760A JP88222650A JP22265088A JPH0270760A JP H0270760 A JPH0270760 A JP H0270760A JP 88222650 A JP88222650 A JP 88222650A JP 22265088 A JP22265088 A JP 22265088A JP H0270760 A JPH0270760 A JP H0270760A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- leuco dye
- acid
- dye compound
- sulfuric acid
- 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
- 150000001875 compounds Chemical class 0.000 title abstract description 11
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract description 4
- -1 fluoran compound Chemical class 0.000 abstract description 4
- 125000001424 substituent group Chemical group 0.000 abstract description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 4
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 abstract description 3
- 239000002253 acid Substances 0.000 abstract description 2
- 239000003377 acid catalyst Substances 0.000 abstract description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- 239000000975 dye Substances 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- MDQRDWAGHRLBPA-UHFFFAOYSA-N fluoroamine Chemical class FN MDQRDWAGHRLBPA-UHFFFAOYSA-N 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- FWQHNLCNFPYBCA-UHFFFAOYSA-N fluoran Chemical class C12=CC=CC=C2OC2=CC=CC=C2C11OC(=O)C2=CC=CC=C21 FWQHNLCNFPYBCA-UHFFFAOYSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Landscapes
- Color Printing (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
Abstract
Description
【発明の詳細な説明】
（発明の利用分野）
本発明はロイコ色素化合物に関し、特に感圧紙、感熱紙
等の記録材料用の無色染料として有用なロイコ色素化合
物に関する。DETAILED DESCRIPTION OF THE INVENTION (Field of Application of the Invention) The present invention relates to a leuco dye compound, and particularly to a leuco dye compound useful as a colorless dye for recording materials such as pressure-sensitive paper and thermal paper.
（従来技術）
無色染料と電子受容性化合物を使用した記録材料は、感
圧紙、感熱紙、感光感圧紙、通電感熱記録紙等として既
によく知られている。たとえば英国特許コｌ弘Ｕリタ、
米国特許弘≠ｔｏｏｔコ、同≠！ｊ６ＰコＯ１特公昭７
Ｉ０−コ３り２２、特開昭ｊ７−／７り１３４．同ＡＯ
−／１３１３乙、同６０−／２３よｊ７などに詳しい。(Prior Art) Recording materials using colorless dyes and electron-accepting compounds are already well known as pressure-sensitive paper, heat-sensitive paper, light-sensitive pressure-sensitive paper, electrically conductive heat-sensitive recording paper, and the like. For example, British Patent Col.
U.S. Patent Hiro≠tootko, the same≠! j6pko O1 special public show 7
I0-ko3ri 22, JP-A-Shoj7-/7ri 134. Same AO
I am familiar with -/1313 Otsu, 60-/23 Yoj7, etc.
最近と＜Ｋ、記録材料の多様化に伴い、耐性の向上、高
感度化などが試みられている。Recently, with the diversification of recording materials, attempts have been made to improve resistance and increase sensitivity.
特に、黒色用を示すフルオラン化合物については、我々
も詳しい検討を行っているが、コーアリール７ミ／−Ｊ
−アルキル、アルコキシ、ハロゲノ又はアリール−乙−
置換アミノフルオランに限られている。In particular, we are conducting detailed studies on fluoran compounds for black color, but
-Alkyl, alkoxy, halogeno or aryl-
Limited to substituted aminofluoranes.
３−位の置換基、６−位の置換基の特性を改良する試み
は多い。There have been many attempts to improve the characteristics of the 3-position substituent and the 6-position substituent.
しかし出発原料である、たとえば３−メチル−弘−アミ
ノアニシジン、３−クロロ−弘−アミノアニシジン又は
３−メトキシ−弘−アミノアニシジンなどは原料入手が
困難で、高価である欠点をもっていた。However, the starting materials, such as 3-methyl-Hiro-aminoanisidine, 3-chloro-Hiro-aminoanisidine, or 3-methoxy-Hiro-aminoanisidine, have the disadvantage of being difficult to obtain and expensive. .
又、２−０−クロロアニリノ−６−置換アミノフルオラ
ンも黒色用を示すことが知られているが、耐光性に欠点
をもっており改良が必要であった。Furthermore, 2-0-chloroanilino-6-substituted aminofluorane is also known to exhibit black color, but it has a drawback in light resistance and needs to be improved.
（発明の目的）
本発明は、３−位に置換基をもたないフルオラン化合物
で、艮好な黒色用を示し、かつ耐性の良好な特定の化合
物ｔ−提供する。(Object of the Invention) The present invention provides a specific compound t- which is a fluoran compound having no substituent at the 3-position, exhibits a good black color, and has good resistance.
本発明は、感熱紙用途に適切な黒色相金示しかつ高感度
化に有効なロイコ色素化合物を提供する。The present invention provides a leuco dye compound that exhibits a black phase suitable for use in thermal paper and is effective for increasing sensitivity.
（発明の構成）
本発明の目的は−−（ｊ 、 ４−ジメチルアニリノ）
−６−ジアルキルアミノフルオランにより達成され友。(Structure of the Invention) The object of the present invention is --(j, 4-dimethylanilino)
- Achieved by 6-dialkylaminofluorane.
本発明の化合物は、釉々の合成ルートに従って調製でき
る。The compounds of the invention can be prepared according to the synthetic route of glazes.
たトエば、コーメチルー≠−エトキシ−２′、６′−ジ
メチルジフェニルアミンと２−ヒドロキシ−弘−ジアル
キルアミノベンゾイル安息香ｉ！ｌｉ！ｔ−濃硫酸、発
煙硫酸、リン酸などの酸触媒を用いて縮合させることに
より容易に得られる。However, comethyl≠-ethoxy-2',6'-dimethyldiphenylamine and 2-hydroxy-Hiro-dialkylaminobenzoyl benzoyl! li! It can be easily obtained by condensation using an acid catalyst such as t-concentrated sulfuric acid, fuming sulfuric acid, or phosphoric acid.
アニリノの２位及び４位にλつのメチル基がある事が、
色相及び耐性（針元・性、耐薬品性、耐ＮＯｘ性など）
向上の上で特に重要である。The presence of λ methyl groups at the 2nd and 4th positions of anilino means that
Hue and resistance (needle base/gender, chemical resistance, NOx resistance, etc.)
This is particularly important for improvement.
（実施例） 以下に、本発明の実施例をつける。(Example) Examples of the present invention are given below.
（実施例／） かきまぜ機のついた２００ｍ１のフラスコ中Ｋ。(Example/) 200m1 medium flask with a stirrer.
１０ｙｄの濃硫酸と２Ｑσの発煙硫酸をはかりとる。Weigh out 10 yards of concentrated sulfuric acid and 2Qσ of fuming sulfuric acid.
かきまぜながら、氷冷し、００１モルのコーヒドロキシ
ー弘−ジエテルアミノベンゾイル安息香酸を滴下し均一
に溶解させる。While stirring and cooling on ice, 001 mol of co-hydroxy-Hiro-dietheraminobenzoylbenzoic acid was added dropwise and uniformly dissolved.
ひきつづき０．１モルの２−メチル−≠−メトキシーλ
′、６′−ジメチルジフェニルアミンを加え、３０分後
に室温に戻し、その温度で参時間ついで参〇 ’Ｃで６
時間かきまぜる。followed by 0.1 mol of 2-methyl-≠-methoxyλ
',6'-dimethyldiphenylamine was added, and after 30 minutes the temperature was returned to room temperature.
Stir the time.
氷冷２０％苛性ソーダ水中に、反応混合物を注いでアル
カリ性とし、析出してくる粗結晶を分離しよく水洗する
。ビスフェノールＡとの接触もしくはシリカゲルプレー
ト上で黒色相を示した。The reaction mixture is made alkaline by pouring it into ice-cold 20% caustic soda water, and the precipitated crude crystals are separated and thoroughly washed with water. It showed a black phase on contact with bisphenol A or on silica gel plates.
シリカゲルを担体とし、ヘキサン−酢酸エチル混合浴媒
で分離すると融点！タターコｏｏ’Ｃの白色結晶として
コー（２，６−ジメチルアニリノ）−６−ジニチルアミ
ノフルオランが得られた。Melting point when separated using silica gel as a carrier and a hexane-ethyl acetate mixed bath medium! Ko(2,6-dimethylanilino)-6-dinithylaminofluorane was obtained as white crystals of Tatako oo'C.
（実施例２）
実施例１の２−ヒドロキシ−弘−ジエチルアミノベンゾ
イル安息香飯に代えて、コーヒドロキシー≠−ジブチル
アミノベンゾイル安息香ｍｔ−用いた。他は同様にして
、コー（２，６−ジメチルアニリノ）−６−シプチルア
ミノフルオランヲ得り。(Example 2) In place of the 2-hydroxy-hiro-diethylaminobenzoylbenzoic rice of Example 1, co-hydroxy≠-dibutylaminobenzoylbenzoyl mt- was used. Co(2,6-dimethylanilino)-6-cyptylaminofluorane was obtained in the same manner.
本発明に於て、６−位のジアルキルアミノ基としては、
総炭素原子数２ないしｌコ特に！ないし１０のＮ−フル
フリル−Ｎ−メチルアミノ−１Ｎ−シクロヘキシル−Ｎ
−ブチルアミノ−１Ｎ−シクロヘキシル−Ｎ−エチルア
ミノ−１Ｎ−イソアミル−Ｎ−エチルアミノ−、ジイソ
ブチルアミノ＋、Ｎ−インプロピルブチルアミノ−、ジ
イソペンチルアミノ、ジプロピルアミノ−などが好まし
い。In the present invention, the dialkylamino group at the 6-position is:
Especially if the total number of carbon atoms is 2 to 1! to 10 N-furfuryl-N-methylamino-1N-cyclohexyl-N
-Butylamino-1N-cyclohexyl-N-ethylamino-1N-isoamyl-N-ethylamino-, diisobutylamino+, N-inpropylbutylamino-, diisopentylamino, dipropylamino-, and the like are preferred.
Claims (1)
ミノフルオラン2-(2,6-dimethylanilino)-6-dialkylaminofluorane
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP88222650A JPH0270760A (en) | 1988-09-06 | 1988-09-06 | Leuco dye compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP88222650A JPH0270760A (en) | 1988-09-06 | 1988-09-06 | Leuco dye compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0270760A true JPH0270760A (en) | 1990-03-09 |
Family
ID=16785778
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP88222650A Pending JPH0270760A (en) | 1988-09-06 | 1988-09-06 | Leuco dye compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0270760A (en) |
-
1988
- 1988-09-06 JP JP88222650A patent/JPH0270760A/en active Pending
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