JPH1060292A - 2-anilino-3-methyl-6-N-n-butyl-N-iso-amylaminofluoran high melting point crystal - Google Patents
2-anilino-3-methyl-6-N-n-butyl-N-iso-amylaminofluoran high melting point crystalInfo
- Publication number
- JPH1060292A JPH1060292A JP8237230A JP23723096A JPH1060292A JP H1060292 A JPH1060292 A JP H1060292A JP 8237230 A JP8237230 A JP 8237230A JP 23723096 A JP23723096 A JP 23723096A JP H1060292 A JPH1060292 A JP H1060292A
- Authority
- JP
- Japan
- Prior art keywords
- melting point
- methyl
- anilino
- butyl
- iso
- 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
- 239000013078 crystal Substances 0.000 title claims abstract description 43
- 238000002844 melting Methods 0.000 title claims abstract description 40
- 230000008018 melting Effects 0.000 title claims abstract description 35
- 238000000034 method Methods 0.000 claims abstract description 19
- 238000002441 X-ray diffraction Methods 0.000 claims abstract description 13
- 238000010521 absorption reaction Methods 0.000 claims abstract description 12
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 claims abstract description 11
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 8
- 239000000126 substance Substances 0.000 claims abstract description 8
- 238000004040 coloring Methods 0.000 abstract description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 8
- FWQHNLCNFPYBCA-UHFFFAOYSA-N fluoran Chemical class C12=CC=CC=C2OC2=CC=CC=C2C11OC(=O)C2=CC=CC=C21 FWQHNLCNFPYBCA-UHFFFAOYSA-N 0.000 abstract description 4
- 230000035945 sensitivity Effects 0.000 abstract description 3
- 230000002123 temporal effect Effects 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000012937 correction Methods 0.000 description 9
- 238000002845 discoloration Methods 0.000 description 9
- 239000002243 precursor Substances 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- -1 fluoran compound Chemical class 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CYMPUOGZUXAIMY-UHFFFAOYSA-N 4-methoxy-2-methyl-n-phenylaniline Chemical compound CC1=CC(OC)=CC=C1NC1=CC=CC=C1 CYMPUOGZUXAIMY-UHFFFAOYSA-N 0.000 description 2
- HIGJFSLYFBALKI-UHFFFAOYSA-N CCCCN(CCC(C)C)F Chemical compound CCCCN(CCC(C)C)F HIGJFSLYFBALKI-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- QKRLLHNFWIVXIH-UHFFFAOYSA-N n-fluoro-3-methylbutan-1-amine Chemical compound CC(C)CCNF QKRLLHNFWIVXIH-UHFFFAOYSA-N 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- ZXYPDMNPLWGWBI-UHFFFAOYSA-N 2'-(2-chloroanilino)-6'-(dibutylamino)spiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound C=1C(N(CCCC)CCCC)=CC=C(C2(C3=CC=CC=C3C(=O)O2)C2=C3)C=1OC2=CC=C3NC1=CC=CC=C1Cl ZXYPDMNPLWGWBI-UHFFFAOYSA-N 0.000 description 1
- MWQVWKAVNPGBJR-UHFFFAOYSA-N 2'-anilino-3'-chloro-6'-(diethylamino)spiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound C=1C(N(CC)CC)=CC=C(C2(C3=CC=CC=C3C(=O)O2)C2=C3)C=1OC2=CC(Cl)=C3NC1=CC=CC=C1 MWQVWKAVNPGBJR-UHFFFAOYSA-N 0.000 description 1
- NRDYAGBYAYPNAQ-UHFFFAOYSA-N 2'-anilino-3'-methyl-6'-[methyl(propyl)amino]spiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound C=1C(N(C)CCC)=CC=C(C2(C3=CC=CC=C3C(=O)O2)C2=C3)C=1OC2=CC(C)=C3NC1=CC=CC=C1 NRDYAGBYAYPNAQ-UHFFFAOYSA-N 0.000 description 1
- XAAILNNJDMIMON-UHFFFAOYSA-N 2'-anilino-6'-(dibutylamino)-3'-methylspiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound C=1C(N(CCCC)CCCC)=CC=C(C2(C3=CC=CC=C3C(=O)O2)C2=C3)C=1OC2=CC(C)=C3NC1=CC=CC=C1 XAAILNNJDMIMON-UHFFFAOYSA-N 0.000 description 1
- CEGHCPGGKKWOKF-UHFFFAOYSA-N 2'-anilino-6'-[cyclohexyl(methyl)amino]-3'-methylspiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound C=1C=C(C2(C3=CC=CC=C3C(=O)O2)C2=CC(NC=3C=CC=CC=3)=C(C)C=C2O2)C2=CC=1N(C)C1CCCCC1 CEGHCPGGKKWOKF-UHFFFAOYSA-N 0.000 description 1
- HUSIBQLZEMMTCQ-UHFFFAOYSA-N 2'-anilino-6'-[ethyl(3-methylbutyl)amino]-3'-methylspiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound C=1C(N(CCC(C)C)CC)=CC=C(C2(C3=CC=CC=C3C(=O)O2)C2=C3)C=1OC2=CC(C)=C3NC1=CC=CC=C1 HUSIBQLZEMMTCQ-UHFFFAOYSA-N 0.000 description 1
- ZTILAOCGFRDHBH-UHFFFAOYSA-N 4-(4-propan-2-yloxyphenyl)sulfonylphenol Chemical compound C1=CC(OC(C)C)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 ZTILAOCGFRDHBH-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000012485 toluene extract Substances 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Landscapes
- Heat Sensitive Colour Forming Recording (AREA)
- Color Printing (AREA)
- Pyrane Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
(57)【要約】
【課題】 発色感度、地肌カブリ性、耐油耐可塑性、耐
光カブリ性および経時安定性のいずれにおいても上市に
充分堪えうる性能を持ち、かつ耐水性耐湿性において抜
群に優れた性能をもつ新しいフルオラン化合物の提供。
【解決手段】 化学式（１）
【化１】
で示され、かつ融点１６２．８〜１６３．５℃、Ｃｕ−
Ｋα線によるＸ線回折法における回折角（２θ）が１
９．６００゜および２２．１４０゜に強いピークがあ
り、ＦＴ−ＩＲによる−ＮＨ−基の主もな吸収が３３７
０ｃｍ-1にあることを特徴とする２−アニリノ−３−メ
チル−６−Ｎ−ｎ−ブチル−Ｎ−ｉｓｏ−アミルアミノ
フルオラン高融点結晶体。(57) [Summary] [Problem] It has a performance that can sufficiently withstand the market in all of the coloring sensitivity, background fog resistance, oil resistance and plasticity resistance, light fog resistance and temporal stability, and is excellent in water resistance and moisture resistance. Providing new fluoran compounds with high performance. SOLUTION: Chemical formula (1) And melting point 162.8-163.5 ° C, Cu-
The diffraction angle (2θ) in the X-ray diffraction method using Kα ray is 1
There are strong peaks at 9.600 ° and 22.140 °, and the main absorption of the —NH— group by FT-IR is 337.
A 2-anilino-3-methyl-6-N-n-butyl-N-iso-amylaminofluoran high-melting crystal which is at 0 cm -1 .
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、２−アニリノ−３
−メチル−６−Ｎ−ｎ−ブチル−Ｎ−ｉｓｏ−アミルア
ミノフルオラン高融点結晶体に関する。TECHNICAL FIELD The present invention relates to 2-anilino-3
-Methyl-6-N-n-butyl-N-iso-amylaminofluorane high melting point crystal.
【０００２】[0002]
【従来技術】従来から感熱記録体に用いる発色色素前駆
体としては種々のフルオラン化合物が提案されており、
とくに特公昭５６−５２７５９号公報には、一般式
（２）2. Description of the Related Art Various fluoran compounds have been proposed as coloring dye precursors for use in thermosensitive recording media.
In particular, Japanese Patent Publication No. 56-52759 discloses the general formula (2)
【化２】 （式中Ｒ1は炭素数５〜８のアルキル基を、Ｒ2は炭素数
１〜８のアルキル基を、Ｒ3は水素原子、炭素数１〜４
の低級アルキル基、ベンジル基を、Ｘ1、Ｘ2は独立して
水素原子、炭素数１〜４の低級アルキル基を、Ｘ3は水
素原子、炭素数１〜４の低級アルキル基、ハロゲン原
子、トリフルオロメチル基を示し、ｎは１又は２の整数
を示す。ただし、Ｒ2が炭素数１〜５のアルキル基を、
Ｘ1、Ｘ2が共に水素原子を、Ｘ3が水素原子、炭素数１
〜４の低級アルキル基、ハロゲン原子を夫々示す時、Ｒ
1はアミル基を示さない。）で表わされるフルオラン化
合物を前記発色色素前駆体とする発明について記載され
ており、多数の例示化合物と実施例が開示されている
が、Ｒ1がＣ4Ｈ9、Ｒ2が（ＣＨ3）2（ＣＨ2）3−、
Ｒ3、Ｘ1、Ｘ2、Ｘ3がいずれも水素である２−アニリノ
−３−メチル−６−Ｎ−ｎ−ブチル−Ｎ−ｉｓｏ−アミ
ルアミノフルオランについては開示されていない。Embedded image (Wherein R 1 is an alkyl group having 5 to 8 carbon atoms, R 2 is an alkyl group having 1 to 8 carbon atoms, R 3 is a hydrogen atom, and 1 to 4 carbon atoms.
X 1 and X 2 are independently a hydrogen atom, a lower alkyl group having 1 to 4 carbon atoms, X 3 is a hydrogen atom, a lower alkyl group having 1 to 4 carbon atoms, a halogen atom , A trifluoromethyl group, and n represents an integer of 1 or 2. Provided that R 2 represents an alkyl group having 1 to 5 carbon atoms,
X 1 and X 2 are both hydrogen atoms, X 3 is a hydrogen atom, and has 1 carbon atom.
When each represents a lower alkyl group of 4 to 4 and a halogen atom,
1 does not represent an amyl group. The invention using the fluoran compound represented by the formula (1) as the color-forming dye precursor is described, and a large number of exemplary compounds and examples are disclosed, wherein R 1 is C 4 H 9 and R 2 is (CH 3 ). 2 (CH 2 ) 3- ,
There is no disclosure of 2-anilino-3-methyl-6-N-n-butyl-N-iso-amylaminofluoran wherein R 3 , X 1 , X 2 and X 3 are all hydrogen.
【０００３】前記公報で代表されるフルオラン系の発色
色素前駆体として、発色感度、地肌カブリ性、耐湿性、
耐油耐可塑剤性、耐光カブリ性などの基本特性がすべて
の点で満足するものとして上市されているものは、３
−ジエチルアミノ−６−メチル−７−アニリノフルオラ
ン、２′−アニリノ−６′−（Ｎ−エチル−Ｎ−イソ
ペンチルアミノ）−３′−メチルスピロ〔フタリド−
３，９′−キサンテン〕、３−（Ｎ−シクロヘキシル
−Ｎ−メチルアミノ）−６−メチル−７−アニリノフル
オラン、２−アニリノ−３−メチル−６−（Ｎ−エチ
ル−ｐ−トルイジノ）フルオラン、３−ジエチルアミ
ノ−７−クロロアニリノフルオラン、２′−（２−ク
ロロアニリノ）−６′−ジブチルアミノスピロ〔フタリ
ド−３，９′−キサンテン〕、２′−アニリノ−３′
−クロロ−６′−（ジエチルアミノ）スピロ〔フタリド
−３，９′−キサンテン〕、２′−アニリノ−３′−
メチル−６′−（Ｎ−メチル−Ｎ−プロピルアミノ）ス
ピロ〔フタリド−３，９′−キサンテン〕、２′−ア
ニリノ−６′−（ジブチルアミノ）−３′−メチルスピ
ロ〔フタリド−３，９′−キサンテン〕など極く限られ
た化合物にすぎない。[0003] As fluoran-based coloring dye precursors represented by the above-mentioned publications, coloring sensitivity, background fog resistance, moisture resistance,
Those that are marketed as satisfying all the basic characteristics such as oil resistance, plasticizer resistance, light fog resistance, etc. are 3
-Diethylamino-6-methyl-7-anilinofluoran, 2'-anilino-6 '-(N-ethyl-N-isopentylamino) -3'-methylspiro [phthalide-
3,9'-xanthene], 3- (N-cyclohexyl-N-methylamino) -6-methyl-7-anilinofluoran, 2-anilino-3-methyl-6- (N-ethyl-p-toluidino ) Fluorane, 3-diethylamino-7-chloroanilinofluoran, 2 '-(2-chloroanilino) -6'-dibutylaminospiro [phthalide-3,9'-xanthene], 2'-anilino-3'
-Chloro-6 '-(diethylamino) spiro [phthalide-3,9'-xanthene], 2'-anilino-3'-
Methyl-6 '-(N-methyl-N-propylamino) spiro [phthalide-3,9'-xanthene], 2'-anilino-6'-(dibutylamino) -3'-methylspiro [phthalide-3,9 '-Xanthene].
【０００４】また、３−ジブチルアミノ−６−メチル−
７−アニリノフルオランについては、特定の結晶変態
が、他の結晶のものに較べて自己発色性と経時黄変性に
優れていることが特公平４−２１６７５号公報に、また
３−ジブチルアミノ−６−メチル−７−（４′−フルオ
ロアニリノ）フルオランについても同様の傾向がみられ
ることが特開昭６０−２１７２６７号公報にそれぞれ記
載されているが、これらの化合物はいずれも前記一般式
におけるＲ1とＲ2がいずれもブチル基の場合についての
みである。Further, 3-dibutylamino-6-methyl-
With respect to 7-anilinofluoran, Japanese Patent Publication No. 4-21675 discloses that a specific crystal modification is superior in self-coloring property and yellowing with time to that of other crystals, and 3-dibutylamino. It is described in JP-A-60-217267 that -6-methyl-7- (4'-fluoroanilino) fluoran exhibits the same tendency, but all of these compounds are of the above general formula. This is only when R 1 and R 2 in the formula are both butyl groups.
【０００５】[0005]
【発明が解決しようとする課題】そこで、本発明の目的
は発色感度、地肌カブリ性、耐油耐可塑剤性、耐光カブ
リ性および経時安定性のいずれにおいても上市に充分堪
えうる性能を持ち、かつ耐水性、耐湿性において抜群に
優れた性能をもつ新しいフルオラン化合物を提供する点
にある。SUMMARY OF THE INVENTION Accordingly, an object of the present invention is to provide a color sensitivity, background fog resistance, oil and plasticizer resistance, light fog resistance and stability over time that are sufficiently high enough to be put on the market. It is an object of the present invention to provide a new fluoran compound having excellent performance in water resistance and moisture resistance.
【０００６】[0006]
【課題を解決するための手段】本発明者らは、各種フル
オラン化合物のうちで、とくに２−アニリノ−３−メチ
ル−６−Ｎ−ｎ−ブチル−Ｎ−ｉｓｏ−アミルアミノフ
ルオランにつき鋭意研究を進めた結果、この化合物は、
前記Ｒ1がＣ4Ｈ9−で、Ｒ2が（ＣＨ3）2（ＣＨ2）3−で
あり、前記特公平４−２１６７５号や特開昭６０−２１
７２６７号公報の化合物が前記Ｒ1とＲ2がいずれもブチ
ル基の場合に複数の結晶体があることは知られている
が、Ｒ1がＣ4Ｈ9−で、Ｒ2が（ＣＨ3）2（ＣＨ2）3−の
場合にも複数の結晶体が存在していることをつきとめ
た。Means for Solving the Problems The present inventors have made intensive studies on 2-anilino-3-methyl-6-Nn-butyl-N-iso-amylaminofluorane, among various fluoran compounds. As a result of this, this compound,
R 1 is C 4 H 9 — and R 2 is (CH 3 ) 2 (CH 2 ) 3 —, as disclosed in JP-B-4-21675 and JP-A-60-21.
It is known that the compound of JP 7267 has a plurality of crystals when both R 1 and R 2 are butyl groups, but R 1 is C 4 H 9 — and R 2 is (CH 3 ) 2 (CH 2) 3 - a plurality of crystals was discovered to be present in the case of.
【０００７】前記化学式（１）で示される１つの結晶体
は、融点１６２．８〜１６３．５℃、Ｃｕ−Ｋα線によ
るＸ線回折法における回折角（２θ）が１９．６００゜
および２２．１４０゜に強いピークがあり（図１参
照）、ＦＴ−ＩＲによる−ＮＨ−基の主もな吸収が３３
７０ｃｍ-1にあり（図２参照）、白色またはわずかに着
色している高融点結晶体であり、他の１つの結晶体は融
点１４８〜１５３℃、Ｃｕ−Ｋα線によるＸ線回折法に
おける回折角（２θ）が６．５８０゜、１７．７６０゜
および２１．１６０゜に強いピークがあり（図３参
照）、ＦＴ−ＩＲによる−ＮＨ−基の吸収が３４０２ｃ
ｍ-1にあり（図４参照）、白色または微緑白色の低融点
結晶体である。One crystal represented by the chemical formula (1) has a melting point of 162.8 to 163.5 ° C., a diffraction angle (2θ) in the X-ray diffraction method using Cu-Kα ray of 19.600 ° and 22. There is a strong peak at 140 ° (see FIG. 1), and the main absorption of the —NH— group by FT-IR is 33%.
It is a high melting point crystal at 70 cm -1 (see FIG. 2), which is white or slightly colored, and the other crystal has a melting point of 148 to 153 ° C., and is obtained by X-ray diffraction using Cu-Kα ray. There are strong peaks at bending angles (2θ) of 6.580 °, 17.760 ° and 21.160 ° (see FIG. 3), and the absorption of the —NH— group by FT-IR is 3402c.
m -1 (see FIG. 4) and is a white or slightly greenish-white low melting point crystal.
【０００８】そこで、この２つの結晶体について種々検
討を行ったところ、前記高融点結晶体を用いて感熱記録
シートを実際に９６時間放置し、目視により変退色の程
度を調べたところ、高融点物使用の場合は変退色が認め
られないのに対して、低融点物は自己発色性が強くいち
じるしい変色があり、地肌が黄色または赤褐色に変色し
てしまうものであった。[0008] Then, when various investigations were conducted on these two crystals, the heat-sensitive recording sheet was actually left standing for 96 hours using the high-melting-point crystals, and the degree of discoloration was visually examined. When the product was used, no discoloration was observed. On the other hand, the low melting point product had a strong self-coloring property and had a remarkable discoloration, and the background was discolored to yellow or reddish brown.
【０００９】そこで、本発明は、化学式（１）Therefore, the present invention provides a compound represented by the chemical formula (1):
【化３】 で示され、かつ融点１６２．８〜１６３．５℃、Ｃｕ−
Ｋα線によるＸ線回折法における回折角（２θ）が１
９．６００゜および２２．１４０゜に強いピークがあ
り、ＦＴ−ＩＲによる−ＮＨ−基の主もな吸収が３３７
０ｃｍ-1にあることを特徴とする２−アニリノ−３−メ
チル−６−Ｎ−ｎ−ブチル−Ｎ−ｉｓｏ−アミルアミノ
フルオラン高融点結晶体に関する。Embedded image And melting point 162.8-163.5 ° C, Cu-
The diffraction angle (2θ) in the X-ray diffraction method using Kα ray is 1
There are strong peaks at 9.600 ° and 22.140 °, and the main absorption of the —NH— group by FT-IR is 337.
The present invention relates to a crystal having a high melting point of 2-anilino-3-methyl-6-N-n-butyl-N-iso-amylaminofluoran, which is at 0 cm -1 .
【００１０】高融点物である本発明結晶体は、例えば以
下のようにして合成することができる。９３〜９９％の
硫酸４５〜２００ｇを１０〜２５℃に保ち、２−（ヒド
ロキシ−４−ｎ−ブチル−Ｎ−ｉｓｏ−アミルアミノベ
ンゾイル）安息香酸１８．０ｇを溶解させる。この溶液
を０〜２０℃に保ち、２−メチル−４−メトオキシジフ
ェニルアミン１０．３ｇを少量ずつ１０〜６０分で加え
る。５〜４５℃で３〜３５時間反応させる。反応液を２
００〜６００ｇの氷水中に注加する。析出する結晶を濾
過水洗してから１０％苛性ソーダ水溶液３００ｇとトル
エン２００〜５００ｇに投入する。還流下、９０分かき
まぜた後、トルエン層を分液、温水で洗浄し、活性炭３
ｇを加え、８０℃に加熱して濾過する。結晶の析出は、
トルエンを６０℃以上で減圧濃縮して、そのまま放冷す
る方法と、さらにシロップ状になるまで濃縮を続けた
後、５０〜５５℃でメタノールを加え、放冷する方法と
がある。なお、約３０℃以下での低温濃縮晶析では低融
点結晶または高融点結晶に若干の低融点結晶が混合した
ものが得られることがあるので注意を要する。The crystalline material of the present invention, which is a high melting point, can be synthesized, for example, as follows. While maintaining 45-200 g of 93-99% sulfuric acid at 10-25 ° C., 18.0 g of 2- (hydroxy-4-n-butyl-N-iso-amylaminobenzoyl) benzoic acid is dissolved. The solution is kept at 0 to 20 ° C., and 10.3 g of 2-methyl-4-methoxydiphenylamine is added little by little over 10 to 60 minutes. React at 5-45 ° C for 3-35 hours. Reaction solution 2
Pour into 100-600 g of ice water. The precipitated crystals are washed with filtered water and then charged into 300 g of a 10% aqueous sodium hydroxide solution and 200 to 500 g of toluene. After stirring under reflux for 90 minutes, the toluene layer was separated and washed with warm water.
g, heat to 80 ° C. and filter. The precipitation of crystals
There are a method of concentrating toluene at 60 ° C. or more under reduced pressure and allowing it to cool as it is, and a method of continuing concentration until a syrup is formed and then adding methanol at 50 to 55 ° C. and allowing it to cool. It should be noted that low-temperature concentrated crystallization at about 30 ° C. or lower may give a mixture of low melting point crystals or high melting point crystals and some low melting point crystals.
【００１１】[0011]
【実施例】以下に実施例と比較例を挙げて本発明を説明
するが、本発明はこれにより限定されるものではない。The present invention will be described below with reference to examples and comparative examples, but the present invention is not limited to these examples.
【００１２】実施例１ （２−アニリノ−３−メチル−６−Ｎ−ｎ−ブチル−Ｎ
−ｉｓｏ−アミルアミノフルオランの高融点物の合成）
９５％硫酸１００ｇを２０℃に保ち、２−（ヒドロキシ
−４−ｎ−ブチル−Ｎ−ｉｓｏ−アミルアミノベンゾイ
ル）安息香酸１８．０ｇを溶解させ１０℃に冷却する。
同温度に保ちながら２−メチル−４−メトオキシジフェ
ニルアミン１０．３ｇを１５分で加え、１０℃で１０時
間反応させ、反応生成物を４００ｇの氷水中に注加す
る。析出した結晶を濾過水洗してから１０％苛性ソーダ
水溶液３００ｇとトルエン２００ｇの混合溶液に投入す
る。トルエン還流下で９０分かきまぜた後、トルエン層
を分液、温水で洗浄し、活性炭３ｇを加え、８０℃に加
熱して濾過する。トルエン抽出物を６０℃以上に加熱し
てトルエンを減圧回収する。溶剤留去後、５０℃のシロ
ップ状の液にメタノール２５０ｍｌを加え、放冷後析出
した結晶を濾別し、メタノールで洗浄してから８０〜９
０℃で乾燥すると白色結晶１５．８ｇが得られた。Example 1 (2-anilino-3-methyl-6-Nn-butyl-N
Synthesis of high melting point product of -iso-amylaminofluoran)
100 g of 95% sulfuric acid is kept at 20 ° C., 18.0 g of 2- (hydroxy-4-n-butyl-N-iso-amylaminobenzoyl) benzoic acid is dissolved and cooled to 10 ° C.
While maintaining the same temperature, 10.3 g of 2-methyl-4-methoxydiphenylamine is added in 15 minutes, reacted at 10 ° C. for 10 hours, and the reaction product is poured into 400 g of ice water. The precipitated crystals are filtered and washed, and then poured into a mixed solution of 300 g of a 10% aqueous sodium hydroxide solution and 200 g of toluene. After stirring under reflux of toluene for 90 minutes, the toluene layer is separated, washed with warm water, added with 3 g of activated carbon, heated to 80 ° C. and filtered. The toluene extract is heated to 60 ° C. or higher, and toluene is recovered under reduced pressure. After distilling off the solvent, 250 ml of methanol was added to the syrupy liquid at 50 ° C., and after standing to cool, the precipitated crystals were separated by filtration, washed with methanol, and then washed with 80 to 9 to 90%
Drying at 0 ° C. yielded 15.8 g of white crystals.
【００１３】この結晶の融点は１６２．８〜１６３．５
℃であり、その９５％酢酸溶液中での最大吸収波長と分
子吸光係数（サンプル０．１ｇを９５％酢酸に溶解し、
１００ｍｌとする。この溶液０．５ｍｌを５０ｍｌメス
フラスコに希釈し、同様に９５％酢酸で５０ｍｌに希釈
し吸光度を測定した。）は、それぞれ測定の結果、４５
０．６ｎｍ・１．９２９×１０4および５９４．２ｎｍ
・１．９９０×１０4であり、Ｃｕ−Ｋα線によるＸ線
回折法における回折角（２θ）が１９．６００゜および
２２．１４０゜に強いピークがあり（図１参照）、ＦＴ
−ＩＲによる−ＮＨ−基の主もな吸収が３３７０ｃｍ-1
にあるものであった。この化合物はトルエンに溶解する
と無色であり、シリカゲル（酸性）上で速やかに黒色に
発色する。また、シリカゲルＴＬＣ板の上での展開では
黒色の単一像であった。The melting point of this crystal is 162.8-163.5.
° C, the maximum absorption wavelength and the molecular extinction coefficient in a 95% acetic acid solution (0.1 g of a sample is dissolved in 95% acetic acid,
Make up to 100 ml. 0.5 ml of this solution was diluted in a 50 ml volumetric flask, similarly diluted to 50 ml with 95% acetic acid, and the absorbance was measured. ) Indicates the result of each measurement, 45
0.6 nm 1.929 × 10 4 and 594.2 nm
1.990 × 10 4 , the diffraction angles (2θ) in the X-ray diffraction method by Cu-Kα ray have strong peaks at 19.600 ° and 22.140 ° (see FIG. 1), and FT
Main absorption of -NH- group by -IR is 3370 cm -1
It was in. This compound is colorless when dissolved in toluene, and rapidly develops a black color on silica gel (acidic). When developed on a silica gel TLC plate, a single black image was obtained.
【００１４】この化合物の元素分析を行った結果は以下
の通りであった。 元素分析値 Ｃ Ｈ Ｎ 理論値 ７９．０９０ ７．００５ ５．１２２ 実測値 ７９．０７２ ６．９８２ ５．１３０ 元素分析の結果から化学式（１）の化合物であることが
証明出来た。The results of elemental analysis of this compound were as follows. Elemental analysis value CHN Theoretical value 79.090 7.005 5.122 Observed value 79.072 6.982 5.130 The result of elemental analysis proved to be the compound of Chemical Formula (1).
【００１５】比較例１ （２−アニリノ−３−メチル−６−Ｎ−ｎ−ブチル−Ｎ
−ｉｓｏ−アミルアミノフルオランの高融点物から低融
点物への変換）実施例１で得られた高融点物５．０ｇを
四塩化炭素３００ｍｌに加え、２時間煮沸し完全に溶解
させる。−２℃まで急速に冷却した後、更に−２〜−１
０℃まで冷却しながら４時間緩やかにかきまぜる。析出
した結晶を濾別し、５℃以下に冷却した四塩化炭素３０
ｍｌで洗浄した後、３０〜４０℃で恒量に達するまで乾
燥すると微緑白色の結晶３．７ｇを得た。Comparative Example 1 (2-anilino-3-methyl-6-Nn-butyl-N
-Conversion of high melting point product of iso-amylaminofluorane from low melting point product) 5.0 g of the high melting point obtained in Example 1 was added to 300 ml of carbon tetrachloride and boiled for 2 hours to completely dissolve. After rapidly cooling to −2 ° C.,
Stir gently for 4 hours while cooling to 0 ° C. The precipitated crystals were separated by filtration, and carbon tetrachloride 30 cooled to 5 ° C. or lower was used.
After washing with ml, it was dried at 30 to 40 ° C. until a constant weight was reached, to obtain 3.7 g of slightly greenish white crystals.
【００１６】この結晶は融点１４９．５〜１５０．４℃
で、Ｃｕ−Ｋα線によるＸ線回折分析を行った結果、回
折角（２θ）６．５８０゜、１７．７６０゜および２
１．１６０゜に強いピークがあり、ＦＴ−ＩＲによる−
ＮＨ−基の吸収が３４０２ｃｍ-1にある低融点の２−ア
ニリノ−３−メチル−６−Ｎ−ｎ−ブチル−Ｎ−ｉｓｏ
−アミルアミノフルオランであった。This crystal has a melting point of 149.5 to 150.4 ° C.
As a result of X-ray diffraction analysis using Cu-Kα ray, diffraction angles (2θ) were 6.580 °, 17.760 ° and 2 °.
1. There is a strong peak at 160 °,
Low melting point 2-anilino-3-methyl-6-Nn-butyl-N-iso with NH-group absorption at 3402 cm -1
-Amylaminofluoran.
【００１７】実施例２ 〔実施例１の化合物を用いた感熱記録シートの作成〕 Ａ液 実施例１で得た高融点の２−アニリノ−３−メチル−６−Ｎ−ｎ− ブチル−Ｎ−ｉｓｏ−アミルアミノフルオラン ２ｇ 水 ２０ｇ ポリビニルアルコール１０％水溶液 ２０ｇ Ｂ液 ４−ヒドロキシ−４′−イソプロポキシ−ジフェニルスルホン ７ｇ 水 １０ｇ ポリビニルアルコール１０％水溶液 ４０ｇ Ａ液、Ｂ液を各々別個にサンドグラインダーを用いて平
均粒径が２．５μになるまで粉砕混和し、各々のスラリ
ーを作成した。このＡ液、Ｂ液とを全量混合し、ペイン
トコンディショナーを用い３０分間かけて均一に分散混
和し、白色のスラリーを調製した。このスラリーを坪量
５０ｇ／ｍ2の上質紙にバーコーターＮｏ−１４（巻線
０．３５ｍｍ）を使用し、高融点の発色色素前駆体の塗
布量が１．５ｇ／ｍ2になるように均一に塗布し、室温
で乾燥して感熱記録シートを作成した。Example 2 [Preparation of a heat-sensitive recording sheet using the compound of Example 1] Solution A High melting point 2-anilino-3-methyl-6-Nn-butyl-N- obtained in Example 1 iso-amylaminofluorane 2 g water 20 g polyvinyl alcohol 10% aqueous solution 20 g solution B 4-hydroxy-4'-isopropoxy-diphenylsulfone 7 g water 10 g polyvinyl alcohol 10% aqueous solution 40 g solution A and solution B were separately sand-grindered. The mixture was pulverized and mixed until the average particle size became 2.5 μm to prepare respective slurries. The solution A and the solution B were all mixed and uniformly dispersed and mixed over 30 minutes using a paint conditioner to prepare a white slurry. Using a bar coater No. 14 (winding 0.35 mm) on high-quality paper having a basis weight of 50 g / m 2 , the slurry was coated such that the coating amount of the high-melting-point coloring dye precursor was 1.5 g / m 2. The coating was uniformly applied and dried at room temperature to prepare a heat-sensitive recording sheet.
【００１８】比較例２ 前記Ａ液の発色色素前駆体を比較例１で得た低融点の２
−アニリノ−３−メチル−６−Ｎ−ｎ−ブチル−Ｎ−ｉ
ｓｏ−アミルアミノフルオランに代えたほかは、実施例
１と同様にして感熱記録シートを製造した。Comparative Example 2 The color-forming dye precursor of the liquid A was prepared by using the low melting point 2 obtained in Comparative Example 1.
-Anilino-3-methyl-6-N-n-butyl-Ni
A heat-sensitive recording sheet was produced in the same manner as in Example 1, except that so-amylaminofluoran was used.
【００１９】これらの感熱シートの自己発色濃度、変退
色および最大発色濃度を測定した結果は、下記表１のと
おりである。The results of measurement of the self-coloring density, discoloration and fading and the maximum coloring density of these heat-sensitive sheets are as shown in Table 1 below.
【表１】 [Table 1]
【００２０】前記各データの測定方法は下記のとおりで
ある。 ◇自己発色濃度 ：マクベス濃度計ＲＤ−５１４型黒
色フィルター（ラッテン（地肌発色濃度） ＃１０６）
で測定した値 ◇変退色 ：感熱記録シートを実際に９６時間
放置し、目視により感熱記録シートの変退色の程度を調
べた。 ◇最大発色濃度 ：熱ブロック印字装置を使用し、１
３５℃ ２ｋｇ／ｃｍ2で３秒間加熱発色させた発色画
像をマクベス濃度計ＲＤ−５１４型黒色フィルター（ラ
ッテン＃１０６）で測定した値The measuring method of each data is as follows. ◇ Self-coloring density: Macbeth densitometer RD-514 type black filter (Ratten (ground color density) # 106)
◇ Discoloration: The thermal recording sheet was actually left for 96 hours, and the degree of discoloration of the thermal recording sheet was visually examined. ◇ Maximum color density: 1
A value obtained by measuring a color image formed by heating and coloring at 35 ° C. 2 kg / cm 2 for 3 seconds with a Macbeth densitometer RD-514 type black filter (Ratten # 106).
【００２１】本発明の結晶体と前記各種の上市化合物と
の各種物性を対比すると下記表２のとおりである。Table 2 below shows various physical properties of the crystal of the present invention and the above-mentioned various commercially available compounds.
【表２】 ◎：非常に優れている ○：優れている □：普通 △：やゝ悪い[Table 2] ◎: Excellent ○: Excellent □: Normal △: Poor
【００２２】１． 化学式（１）1. Chemical formula (1)
【化４】 で示され、かつ融点１６２．８〜１６３．５℃、Ｃｕ−
Ｋα線によるＸ線回折法における回折角（２θ）が１
９．６００゜および２２．１４０゜に強いピークがあ
り、ＦＴ−ＩＲによる−ＮＨ−基の主もな吸収が３３７
０ｃｍ-1にあることを特徴とする２−アニリノ−３−メ
チル−６−Ｎ−ｎ−ブチル−Ｎ−ｉｓｏ−アミルアミノ
フルオラン高融点結晶体。 ２． 前記１．の高融点結晶体を含む発色色素前駆体。 ３． 発色層に前記１．の高融点結晶体を含む感熱記録
体。Embedded image And melting point 162.8-163.5 ° C, Cu-
The diffraction angle (2θ) in the X-ray diffraction method using Kα ray is 1
There are strong peaks at 9.600 ° and 22.140 °, and the main absorption of the —NH— group by FT-IR is 337.
A 2-anilino-3-methyl-6-N-n-butyl-N-iso-amylaminofluoran high-melting crystal which is at 0 cm -1 . 2. 1. A coloring dye precursor containing a high melting point crystal of the above. 3. The above-described 1. Thermosensitive recording medium containing a high-melting-point crystal.
【００２３】[0023]
【効果】 （１）本発明の結晶体は、従来上市の前駆体に較べて、
耐水性、耐湿性が格段にすぐれている。 （２）本発明の結晶体はカプセルオイルに対する溶解性
が良いので感熱色素としても利用できる。 （３）本発明の高融点結晶体を用いた感熱記録体は、低
融点結晶体を用いたものが自己発色性が強く、光により
地肌が黄色または赤褐色に変色してしまうのに較べて、
このような変退色がなく、極めて安定であった。 （４）本発明の発色色素前駆体を用いた感熱記録体は、
自己発色性、即ち、地肌発色がなく、対日光によって変
退色のない、すぐれたものであった。[Effects] (1) The crystalline form of the present invention is
Water resistance and moisture resistance are remarkably excellent. (2) Since the crystal of the present invention has good solubility in capsule oil, it can be used as a thermosensitive dye. (3) Compared to the thermosensitive recording medium using the high melting point crystal of the present invention which uses the low melting point crystal, the self-coloring property is strong and the background is discolored to yellow or reddish brown by light.
There was no such discoloration and discoloration, and it was extremely stable. (4) The thermosensitive recording material using the coloring dye precursor of the present invention is:
It had excellent self-coloring properties, that is, no background coloring and no discoloration due to sunlight.
【図１】本発明の２−アニリノ−３−メチル−６−Ｎ−
ｎ−ブチル−Ｎ−ｉｓｏ−アミルアミノフルオランの高
融点結晶体のＸ線回折図であり、横軸は回折（２θ）を
示し、縦軸は回折強度を示す。FIG. 1 shows the 2-anilino-3-methyl-6-N- of the present invention.
FIG. 3 is an X-ray diffraction diagram of a high melting point crystal of n-butyl-N-iso-amylaminofluoran, where the horizontal axis indicates diffraction (2θ) and the vertical axis indicates diffraction intensity.
【図２】本発明の２−アニリノ−３−メチル−６−Ｎ−
ｎ−ブチル−Ｎ−ｉｓｏ−アミルアミノフルオランの高
融点結晶体のＦＴ−ＩＲの測定チャートである。FIG. 2 shows the 2-anilino-3-methyl-6-N- of the present invention.
It is a FT-IR measurement chart of a high melting point crystal of n-butyl-N-iso-amylaminofluoran.
【図３】２−アニリノ−３−メチル−６−Ｎ−ｎ−ブチ
ル−Ｎ−ｉｓｏ−アミルアミノフルオランの低融点結晶
体のＸ線回折図であり、横軸は回折（２θ）を示し、縦
軸は回折強度を示す。FIG. 3 is an X-ray diffraction pattern of a low-melting-point crystal of 2-anilino-3-methyl-6-N-n-butyl-N-iso-amylaminofluoran, and the horizontal axis indicates diffraction (2θ). The vertical axis indicates the diffraction intensity.
【図４】２−アニリノ−３−メチル−６−Ｎ−ｎ−ブチ
ル−Ｎ−ｉｓｏ−アミルアミノフルオランの低融点結晶
体のＦＴ−ＩＲの測定チャートである。FIG. 4 is an FT-IR measurement chart of a low-melting-point crystal of 2-anilino-3-methyl-6-N-n-butyl-N-iso-amylaminofluoran.
【手続補正書】[Procedure amendment]
【提出日】平成８年９月９日[Submission date] September 9, 1996
【手続補正１】[Procedure amendment 1]
【補正対象書類名】明細書[Document name to be amended] Statement
【補正対象項目名】特許請求の範囲[Correction target item name] Claims
【補正方法】変更[Correction method] Change
【補正内容】[Correction contents]
【特許請求の範囲】[Claims]
【化１】 で示され、かつ融点１６２．８〜１６３．５℃、Ｃｕ−
Ｋα線によるＸ線回折法における回折角（２θ）が１
９．６００゜および２２．１４０゜に強いピークがあ
り、ＦＴ−ＩＲによる−ＮＨ−基の主もな吸収が３３７
０ｃｍ-1にあることを特徴とする２−アニリノ−３−メ
チル−６−Ｎ−ｎ−ブチル−Ｎ−ｉｓｏ−アミルアミノ
フルオラン高融点結晶体。Embedded image And melting point 162.8-163.5 ° C, Cu-
The diffraction angle (2θ) in the X-ray diffraction method using Kα ray is 1
There are strong peaks at 9.600 ° and 22.140 °, and the main absorption of the —NH— group by FT-IR is 337.
A 2-anilino-3-methyl-6-N-n-butyl-N-iso-amylaminofluoran high-melting crystal which is at 0 cm -1 .
【手続補正２】[Procedure amendment 2]
【補正対象書類名】明細書[Document name to be amended] Statement
【補正対象項目名】０００９[Correction target item name] 0009
【補正方法】変更[Correction method] Change
【補正内容】[Correction contents]
【０００９】そこで、本発明は、化学式（１）Therefore, the present invention provides a compound represented by the chemical formula (1):
【化３】 で示され、かつ融点１６２．８〜１６３．５℃、Ｃｕ−
Ｋα線によるＸ線回折法における回折角（２θ）が１
９．６００゜および２２．１４０゜に強いピークがあ
り、ＦＴ−ＩＲによる−ＮＨ−基の主もな吸収が３３７
０ｃｍ-1にあることを特徴とする２−アニリノ−３−メ
チル−６−Ｎ−ｎ−ブチル−Ｎ−ｉｓｏ−アミルアミノ
フルオラン高融点結晶体に関する。Embedded image And melting point 162.8-163.5 ° C, Cu-
The diffraction angle (2θ) in the X-ray diffraction method using Kα ray is 1
There are strong peaks at 9.600 ° and 22.140 °, and the main absorption of the —NH— group by FT-IR is 337.
The present invention relates to a crystal having a high melting point of 2-anilino-3-methyl-6-N-n-butyl-N-iso-amylaminofluoran, which is at 0 cm -1 .
【手続補正３】[Procedure amendment 3]
【補正対象書類名】明細書[Document name to be amended] Statement
【補正対象項目名】００２２[Correction target item name] 0022
【補正方法】変更[Correction method] Change
【補正内容】[Correction contents]
【００２２】１． 化学式（１）1. Chemical formula (1)
【化４】 で示され、かつ融点１６２．８〜１６３．５℃、Ｃｕ−
Ｋα線によるＸ線回折法における回折角（２θ）が１
９．６００゜および２２．１４０゜に強いピークがあ
り、ＦＴ−ＩＲによる−ＮＨ−基の主もな吸収が３３７
０ｃｍ-1にあることを特徴とする２−アニリノ−３−メ
チル−６−Ｎ−ｎ−ブチル−Ｎ−ｉｓｏ−アミルアミノ
フルオラン高融点結晶体。 ２． 前記１．の高融点結晶体を含む発色色素前駆体。 ３． 発色層に前記１．の高融点結晶体を含む感熱記録
体。Embedded image And melting point 162.8-163.5 ° C, Cu-
The diffraction angle (2θ) in the X-ray diffraction method using Kα ray is 1
There are strong peaks at 9.600 ° and 22.140 °, and the main absorption of the —NH— group by FT-IR is 337.
A 2-anilino-3-methyl-6-N-n-butyl-N-iso-amylaminofluoran high-melting crystal which is at 0 cm -1 . 2. 1. A coloring dye precursor containing a high melting point crystal of the above. 3. The above-described 1. Thermosensitive recording medium containing a high-melting-point crystal.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 庁内整理番号 ＦＩ 技術表示箇所 // Ｃ０７Ｄ 311/86 Ｂ４１Ｍ 5/18 １０５ ──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. 6 Identification number Agency reference number FI Technical display location // C07D 311/86 B41M 5/18 105
Claims (1)
Ｋα線によるＸ線回折法における回折角（２θ）が１
９．６００゜および２２．１４０゜に強いピークがあ
り、ＦＴ−ＩＲによる−ＮＨ−基の主もな吸収が３３７
０ｃｍ-1にあることを特徴とする２−アニリノ−３−メ
チル−６−Ｎ−ｎ−ブチル−Ｎ−ｉｓｏ−アミルアミノ
フルオラン高融点結晶体。[Claim 1] Chemical formula (1) And melting point 162.8-163.5 ° C, Cu-
The diffraction angle (2θ) in the X-ray diffraction method using Kα ray is 1
There are strong peaks at 9.600 ° and 22.140 °, and the main absorption of the —NH— group by FT-IR is 337.
A 2-anilino-3-methyl-6-N-n-butyl-N-iso-amylaminofluoran high-melting crystal which is at 0 cm -1 .
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8237230A JPH1060292A (en) | 1996-08-20 | 1996-08-20 | 2-anilino-3-methyl-6-N-n-butyl-N-iso-amylaminofluoran high melting point crystal |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8237230A JPH1060292A (en) | 1996-08-20 | 1996-08-20 | 2-anilino-3-methyl-6-N-n-butyl-N-iso-amylaminofluoran high melting point crystal |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH1060292A true JPH1060292A (en) | 1998-03-03 |
Family
ID=17012319
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8237230A Pending JPH1060292A (en) | 1996-08-20 | 1996-08-20 | 2-anilino-3-methyl-6-N-n-butyl-N-iso-amylaminofluoran high melting point crystal |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH1060292A (en) |
-
1996
- 1996-08-20 JP JP8237230A patent/JPH1060292A/en active Pending
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