JPH0245568A - Leuco pigment compound - Google Patents
Leuco pigment compoundInfo
- Publication number
- JPH0245568A JPH0245568A JP63195781A JP19578188A JPH0245568A JP H0245568 A JPH0245568 A JP H0245568A JP 63195781 A JP63195781 A JP 63195781A JP 19578188 A JP19578188 A JP 19578188A JP H0245568 A JPH0245568 A JP H0245568A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- sensitive paper
- methyl
- heat
- 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 8
- 239000000049 pigment Substances 0.000 title 1
- 239000000463 material Substances 0.000 abstract description 6
- 230000035945 sensitivity Effects 0.000 abstract description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-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
- 239000003377 acid catalyst Substances 0.000 abstract description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract description 2
- 239000000975 dye Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 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
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical group F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 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
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- -1 dipropylamino- Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
Landscapes
- Heat Sensitive Colour Forming Recording (AREA)
- Color Printing (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全便用した記録材料は、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２／弘Ｏ≠≠
２、米国特許弘弘ｔｏｏｔλ、同！ＩＡｊ Ａり２０１
特公昭６０−．２Ｊり２コ、特開昭！７−／７９ｒ３１
ｒ、同１．０−１２３１！ｔ。(Prior Art) Recording materials containing 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 2/Hiroo≠≠
2. U.S. patent Hirohiro tootλ, same! IAj Ari201
Tokuko Showa 60-. 2J Ri2ko, Tokukai Akira! 7-/79r31
r, same 1.0-1231! t.
同４０−／コ３！！７などに詳しい。Same 40-/ko 3! ! I am familiar with 7 etc.
最近とくに、記録材料の高速度化に伴い、記録速度の向
上、高感度化が試みられている。Recently, in particular, with the increase in the speed of recording materials, attempts have been made to improve the recording speed and sensitivity.
感熱紙の高感度化に対しては既にいくつかの手法が検討
されており、その７つけ熱可融化剤を用いるものである
。Several methods have already been considered for increasing the sensitivity of thermal paper, and one of them is the use of a heat-fusible agent.
熱可融化剤については特開昭ｊ♂−！７７ｒり、同よ？
−了７０タグなど非常に基本的な我々の発明がある。For information on heat-fusifying agents, please refer to JP Kokai Shoj♂-! 77rri, same?
- There are some very basic inventions of ours, such as the 70 tag.
が、この方法では発色反応に直接寄与しない成分全記録
材料中に含有させるために、ハンドリング及びコストの
問題があった。However, this method has problems in handling and cost because components that do not directly contribute to the color reaction are included in the entire recording material.
一方、フルオラン環に長鎖アルキル基金導入し油溶性の
向上と低融点化による感度の向上も試みられているが原
料入手の点で若干の問題があった。On the other hand, attempts have been made to improve oil solubility and sensitivity by lowering the melting point by introducing a long-chain alkyl group into the fluorane ring, but there have been some problems in obtaining raw materials.
本発明者らはλ−位アニリノ基の各種置換基に検討を加
え高感度化に有効なロイコ色素化合物全見出したもので
ある。The present inventors investigated various substituents of the λ-position anilino group and discovered all leuco dye compounds effective for increasing sensitivity.
（本発明の目的）
本発明は、感熱紙用途に適切な黒色相を示しかつ高感度
化に有効なロイコ色素化合物を提供する。(Object of the present invention) The present invention provides a leuco dye compound that exhibits a black hue suitable for use in thermal paper and is effective for increasing sensitivity.
（発明の構成）
本発明の目的はλ−ｐ−エチルアニリノ−３−メチル−
２−ジアルキルアミノフルオランによシ達成された。(Structure of the Invention) The object of the present invention is to
This was achieved with 2-dialkylaminofluorane.
本発明の化合物は、種々の合成ルートに従って調製でき
る。Compounds of the invention can be prepared according to a variety of synthetic routes.
たとえば、２−メチル−弘−エトキシ−μ′エチルジフ
ェニルアミント２−ヒドロキシ−弘−ジアルキルアミノ
ベンゾイル安息香酸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
。For example, 2-methyl-Hiro-ethoxy-μ'ethyldiphenylaminete 2-hydroxy-Hiro-dialkylaminobenzoylbenzoic acid can be easily obtained by condensation using an acid catalyst such as concentrated sulfuric acid, fuming sulfuric acid, or phosphoric acid. It will be done.
アニリノのｐ−位にエチル基がある事が、色相と融点の
点から特に重要である。The presence of an ethyl group at the p-position of anilino is particularly important from the viewpoint of hue and melting point.
（実施例１）
かきまぜ機のついた２００ｎｌのフラスコ中に、♂０ｒ
ｎｌの濃硫酸と２０４の発煙硫酸をはかりとる。(Example 1) In a 200nl flask equipped with a stirrer, ♂0r
Weigh out nl of concentrated sulfuric acid and 204 ml of fuming sulfuric acid.
かきまぜながら、水冷し、０．７モルのコーヒドロキシ
ー≠−ジエチ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, the mixture is cooled with water, and 0.7 mol of co-hydroxy≠-diethylaminobenzoylbenzoic acid is added dropwise to uniformly dissolve.
ひきつづき０，１モルのλ−メチルー弘−メトキシー≠
′−エチルジフェニルアミン１ＪＩＩＩｔ、７０分後に
室温に戻し、その温度でμ時間ついで≠００Ｃで４時間
かきまぜる。Continued 0.1 mole of λ-methyl-Hiro-methoxy≠
'-ethyldiphenylamine 1JIIIt, returned to room temperature after 70 minutes, stirred at that temperature for μ hours and then at ≠00C for 4 hours.
水冷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、ベンゼンから再結晶すると融点ｌ
λ０−／ｕコ０Ｃの白色結晶として２−ｐ−二チルアニ
リノー３−メチル−ぶ−ジエチルアミノフルオランが得
られた。The reaction mixture is poured into water-cooled 20% caustic soda water to make it alkaline, and the precipitated coarse crystals are separated and thoroughly washed with water. It shows a black phase on contact with bisphenol A or on silica gel plates, and when recrystallized from benzene it has a melting point of l.
2-p-ditylanilino-3-methyl-bu-diethylaminofluorane was obtained as white crystals of λ0-/u0C.
（実施例、２）
実施例／の２−ヒドロキシ−弘−ジエチルアミノヘンソ
イル安息香酸に代えて、λ−ヒドロキシー≠−ジブチル
アミノベンゾイル安息香酸を用い他は同様にしてｓ”−
ｐ−エチルアニリ、／−３−メチル−６−シブチルアミ
ノフルオランを得た。(Example 2) In place of 2-hydroxy-Hiro-diethylaminobenzoylbenzoic acid in Example 2, λ-hydroxy≠-dibutylaminobenzoylbenzoic acid was used, and the other conditions were the same as s”-
p-ethylanili,/-3-methyl-6-sibutylaminofluorane was obtained.
酢酸エチル−ヘキサン混合溶媒から再結晶すると融点１
ｏｒ−／／（７０Ｃの白色結晶として単離された。When recrystallized from a mixed solvent of ethyl acetate and hexane, the melting point is 1.
or-//(isolated as white crystals at 70C).
本発明に於て、６−位のジアルキルアミノ基としては、
総炭素原子数コないし／λ特に弘ないし１０のＮ−フル
フリル−Ｎ〜メチルアミノ−１Ｎ〜シクロへキシル−Ｎ
−ｉチルアミノ−１Ｎ−シクロへキシル−Ｎ−エチルア
ミノ−１Ｎ−インアミル−Ｎ−エチルアミノ−、ジイン
ブチルアミノ−Ｎ−イソプロピルブチルアミノ−、ジイ
ンはンチルアミノ、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:
N-furfuryl-N to methylamino-1N to cyclohexyl-N with a total number of carbon atoms from 1 to 10, especially Hiro to 10
-ithylamino-1N-cyclohexyl-N-ethylamino-1N-yamyl-N-ethylamino-, diynebutylamino-N-isopropylamino-, diyne is preferably enthylamino, dipropylamino-, or the like.
Claims (1)
アミノフルオラン2-p-ethylanilino-3-methyl-6-dialkylaminofluorane
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63195781A JPH0245568A (en) | 1988-08-05 | 1988-08-05 | Leuco pigment compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63195781A JPH0245568A (en) | 1988-08-05 | 1988-08-05 | Leuco pigment compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0245568A true JPH0245568A (en) | 1990-02-15 |
Family
ID=16346858
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63195781A Pending JPH0245568A (en) | 1988-08-05 | 1988-08-05 | Leuco pigment compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0245568A (en) |
-
1988
- 1988-08-05 JP JP63195781A patent/JPH0245568A/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4330473A (en) | Recording material | |
| JPS598302B2 (en) | Fukusokanshikichikanlactonekagobutsunoseihou | |
| EP0220515B1 (en) | Fluoran derivatives, process for preparation thereof and recording material containing the same | |
| JPH0245568A (en) | Leuco pigment compound | |
| JPS59175444A (en) | Phenolic compound and thermally sensitive recorder containing the same | |
| US3996212A (en) | Fluoran compounds | |
| JP2866108B2 (en) | Method for producing benzoic acid derivative | |
| JPS6118943B2 (en) | ||
| JPH03240761A (en) | Benzoic acid derivative and production thereof | |
| JP3627196B2 (en) | Fluorane compound and chromogenic recording material using the same | |
| JPS6191259A (en) | Fluoran compound and its preparation | |
| JPH0270760A (en) | Leuco dye compound | |
| JP2764317B2 (en) | Benzoic acid derivative and method for producing the same | |
| JPS61229591A (en) | Thermal recording material | |
| JPH0641141A (en) | Fluoran compound | |
| JPH06107665A (en) | Bislactone compound and its production | |
| JPH04187687A (en) | Preparation of fluorane compound | |
| JPH075844B2 (en) | Novel fluoran compound and color former for leuco heat-sensitive recording materials containing the same | |
| CN114163429A (en) | Thermochromic material with single-crystal violet lactone structure, color developing composition, preparation method and application of thermochromic material | |
| JPS59142254A (en) | Novel fluoran derivative and thermal recording material using the same | |
| JPS6047067A (en) | Fluoran compound and production thereof | |
| JPS6037799B2 (en) | Chromogenic recording material | |
| JPH01308459A (en) | Production of leuco compound | |
| JPH02138368A (en) | leuco dye | |
| JPS62161750A (en) | Benzoic acid derivative |