JPS6157651A - Indoaniline compounds, thermal transfer recording dyes, and thermal transfer recording sheets - Google Patents
Indoaniline compounds, thermal transfer recording dyes, and thermal transfer recording sheetsInfo
- Publication number
- JPS6157651A JPS6157651A JP59181230A JP18123084A JPS6157651A JP S6157651 A JPS6157651 A JP S6157651A JP 59181230 A JP59181230 A JP 59181230A JP 18123084 A JP18123084 A JP 18123084A JP S6157651 A JPS6157651 A JP S6157651A
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Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 11
- 239000000975 dye Substances 0.000 title abstract description 21
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 21
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims abstract 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract 3
- 150000002367 halogens Chemical class 0.000 claims abstract 3
- 239000000126 substance Substances 0.000 claims description 43
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims 6
- 125000001153 fluoro group Chemical group F* 0.000 claims 6
- 125000003277 amino group Chemical group 0.000 claims 2
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 abstract description 6
- 238000002360 preparation method Methods 0.000 abstract description 5
- 229910001961 silver nitrate Inorganic materials 0.000 abstract description 3
- 238000000859 sublimation Methods 0.000 abstract description 3
- 230000008022 sublimation Effects 0.000 abstract description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000007800 oxidant agent Substances 0.000 abstract 1
- 239000000976 ink Substances 0.000 description 16
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
- 238000005516 engineering process Methods 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000008033 biological extinction Effects 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- 229920002492 poly(sulfone) Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- ZYKBEIDPRRYKKQ-UHFFFAOYSA-N 4-[4-(diethylamino)-2-methylphenyl]imino-1-oxo-n-phenylnaphthalene-2-carboxamide Chemical compound CC1=CC(N(CC)CC)=CC=C1N=C1C2=CC=CC=C2C(=O)C(C(=O)NC=2C=CC=CC=2)=C1 ZYKBEIDPRRYKKQ-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004962 Polyamide-imide Substances 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- RYPWQHONZWFXBN-UHFFFAOYSA-N dichloromethyl(methylidene)-$l^{3}-chlorane Chemical compound ClC(Cl)Cl=C RYPWQHONZWFXBN-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000011086 glassine Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229940035429 isobutyl alcohol Drugs 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- -1 moisture Substances 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 238000007665 sagging Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000005092 sublimation method Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Impression-Transfer Materials And Handling Thereof (AREA)
- Thermal Transfer Or Thermal Recording In General (AREA)
Abstract
Description
【発明の詳細な説明】
発明の目的
イ〕 産業上の利用分野
本発明は、新規インドアニリン系化合物及び昇華型感熱
転写記録に使用される色素に関する。DETAILED DESCRIPTION OF THE INVENTION OBJECT OF THE INVENTION A] Industrial Field of Application The present invention relates to a novel indoaniline compound and a dye used in dye sublimation heat-sensitive transfer recording.
口）従来の技術
従来、ファクシミリプリンター、複写機あるいは、テレ
ビ画際等ｔカラー記急する技術が要望され、電子写真、
インクジェット、感熱転写等によるカラー記録技術が検
討されている。(Example) Conventional technology In the past, there was a demand for T-color recording technology such as facsimile printers, copying machines, and television screens, and electrophotography,
Color recording technologies using inkjet, thermal transfer, etc. are being considered.
・ 感熱転写記録方式は、装置の保守や操作が容易で
、装置や消耗品が安価であるため、他の方法に比べ有利
と考えられる。- The thermal transfer recording method is considered advantageous over other methods because the equipment is easy to maintain and operate, and the equipment and consumables are inexpensive.
感熱転写方式には、ベースフィルム上に熱溶融性インク
層を形成させた転写シートｔ。The thermal transfer method uses a transfer sheet t in which a heat-melting ink layer is formed on a base film.
感熱ヘッドにより刃口熱して、該インクを溶融し、被記
録体上に転写記録する溶融方式と。A melting method in which a thermal head heats the cutting edge to melt the ink and transfer it onto a recording medium.
ベースフィルム上に昇華性色素を含有するインク層を形
成させた転写シートｔ、感熱ヘッドにより加熱して色素
を昇華させ、被記録体上に転写記録する昇華方式とがあ
るが、昇華方式は感熱ヘッドに与えるエネルギーχ変え
ることにより色素の昇華転写ｉ′ヒ制御することができ
るので１階調記録が容易となり、フルカラー記録には特
に有利と考えられる。There is a transfer sheet t in which an ink layer containing a sublimable dye is formed on a base film, and a sublimation method uses a heat-sensitive head to heat the dye to sublimate it and transfer it to the recording medium. By changing the energy χ applied to the head, the dye sublimation transfer i' can be controlled, which facilitates one-gradation recording, which is considered to be particularly advantageous for full-color recording.
パノ 発明が解決しようとする問題点
この記録方式に適用する色素としては以下のような条件
が具備される必要がある。Pano Problems to be Solved by the Invention The following conditions must be met for the dye to be applied to this recording method.
すなわち、感熱記録ヘッドの作動条件で容易に昇華し、
感熱記録ヘッドの作動条件で熱分解せず１色再現上、好
ましい色相？有し。That is, it sublimates easily under the operating conditions of the thermal recording head,
What is the preferred hue for reproducing one color without thermal decomposition under the operating conditions of a thermal recording head? I have it.
分子吸光係数が大きく、熱、党、湿気、薬品などに対し
て安定であり１合成が容易であり。It has a large molecular extinction coefficient, is stable against heat, dust, moisture, chemicals, etc., and is easy to synthesize.
そしてインク化適性が優れている等である。It also has excellent suitability for ink production.
二）発明の目的
不発明は、上記の条件′ｆｔ溝足するシアン色素の提供
Ｉその目的とするものである。2) Object of the invention The object of the invention is to provide a cyan dye that satisfies the above conditions.
発明の構成
イ〕 問題点ｌ解決するための手段
本発明は、一般式ＣＩＩ
（式中、又は水素原子、フッ素原子により置換されてい
てもよいアルキル基、アルコキシ基、ホルミルアミノ基
、フッ素ご子により置換すれていてもよいアルキルカル
ボニルアミノ基、アリールカルボニルアミノ基又はハロ
ゲン原子を表わし、Ｙは水素原子、フッ素原子により置
換されていてもよいアルキル基、アルコキシ基又はハロ
ゲンぶ子を表わし、Ｒ１およびＲ１は水素原子、Ｃ１〜
、の置換もしくは非置換のアルキル基を表わし Ｒ３お
よびＲ４はよびＲ６は０１〜Ｂの置換もしくは非置換の
アルキル基を表わす］
で示される新規インドアニＩＪン系化合物お裏び感熱転
写配分用色素をその要旨とするものである。Structure of the Invention (a) Means for Solving Problems (1) The present invention solves the problems by solving the following problems: R1 and R1 is a hydrogen atom, C1~
represents a substituted or unsubstituted alkyl group, and R3 and R4 represent a substituted or unsubstituted alkyl group of 01 to B] and a dye for thermal transfer distribution. This is the summary.
本発明の一般式ＣＩ）で示されるインドアニ
１リン系化合物および感熱転写記鎌用色素において ｐ
ｌ、 Ｒ２，Ｉ（ｉ及びＲ６の置換アルギル基の置換基
としては、ハロゲン原子、アルコキシ基、ビニル基、ヒ
トａｑシ基、アリル基等カ挙げられる。Indian anidine represented by the general formula CI) of the present invention
1 In phosphorus compounds and dyes for thermal transfer printing, p
Examples of the substituent for the substituted argyl group for i and R6 include a halogen atom, an alkoxy group, a vinyl group, a human aq group, and an allyl group.
上記本発明の化合物および色素の製造性としては、たと
えば、下記一般式ＣＩＩ）（式中、 Ｒ３，Ｒ４は前記
定義に同じ。）で示されるフェノール類と下記一般式圓
（式中、Ｘ、Ｙ、Ｒ１およびＲ２は前記定ｉＫ同じ。）
で示されるアニリン類とを硝酸鉄等の酸化剤で処理する
ことにより得ることかで′きる。As for the manufacturability of the compounds and dyes of the present invention, for example, phenols represented by the following general formula CII) (wherein, R3 and R4 are the same as defined above) and the following general formula (wherein, X, Y, R1 and R2 are the same as defined above.
本発明のインドアニＩＪン系化会物及び感熱伝写記碌用
色素の一般式〔Ｉ〕において、４？に好ましいものとし
ては、ＸおよびＹが水素原子、メチル基、メトギシ基、
エトキシ基、塩素原子、臭素原子又はトリフルオロメチ
ル基を示し、Ｒ１および創が氷素原子、ヒトＯ−？シア
ル中ル基、アラルキル基又はＯ，ｋａのアル争Ｃ１，４
のアルキル基又はハロゲン化アルキル基で示されろ化合
物及び色素か挙げられる。In the general formula [I] of the Indian compound and thermal transfer dye of the present invention, 4? Preferably, X and Y are a hydrogen atom, a methyl group, a methoxy group,
Indicates an ethoxy group, a chlorine atom, a bromine atom, or a trifluoromethyl group, R1 and an ice atom, and a human O-? Al group in sial, aralkyl group or O, ka alkyl group C1,4
Compounds and dyes represented by an alkyl group or a halogenated alkyl group may be mentioned.
本発明の化合物（色素）を不記録方式に適用する場合、
化金物を結着剤とともに媒体中に溶解あるいぼ微粒子状
に分散させることによりインクを調製し、該インクｔベ
ースフィルム上に塗布、乾燥し転写シートを炸裂する必
要がある。When applying the compound (dye) of the present invention to a non-recording method,
It is necessary to prepare an ink by dissolving or dispersing the chemical compound in the form of fine particles in a medium together with a binder, apply the ink onto a base film, dry it, and explode the transfer sheet.
インク調製のための結着剤としては、セルロース系、ア
クリル酸系、でんぷん系などの水溶性樹脂、アクリル樹
脂、メタクリル樹脂。Binders for ink preparation include water-soluble resins such as cellulose, acrylic acid, and starch, acrylic resins, and methacrylic resins.
ポリスチレン、ポリカーボネート、ポリスルホン、ポリ
エーテルスルホン、エチルセルロースなどの茗機溶剤に
可溶性の樹脂などン挙げることができる。有機溶剤可溶
性の閘脂の場合有機溶剤溶液としてのみならず水性分散
液の形で使用することも可能である。Examples include resins soluble in the organic solvent, such as polystyrene, polycarbonate, polysulfone, polyethersulfone, and ethyl cellulose. In the case of organic solvent-soluble resins, it is possible to use them not only as organic solvent solutions but also in the form of aqueous dispersions.
インク調製のための媒体としては水の他に。Besides water as a medium for ink preparation.
メチルアルコール、イソプロピルアルコール。Methyl alcohol, isopropyl alcohol.
イソブチルアルコールなどのアルコール類。Alcohols such as isobutyl alcohol.
メチルセロソルブ、エチルセロソルブなどのセロソルブ
類、トルエン、キシレン、りａロペンゼンなどの芳香族
類、酢酸エチル、酢酸ブチルなどのエステル類、アセト
ン、メチルエチルケトン、メチルイソブチルケトン、シ
クロヘキサノ７などのケトン類、塩化メチレン、クロロ
ホルム、トリクロロエチレンなどの塩累系溶剤、テトラ
ヒドロフラン、ジオキサンがトのエーテル％ｉ、Ｎ、Ｎ
−ジメチルホルムアミド、Ｎ−メチルピロリドンなどの
有機溶剤を挙げることができる。Cellosolves such as methyl cellosolve and ethyl cellosolve, aromatics such as toluene, xylene and lyalopenzene, esters such as ethyl acetate and butyl acetate, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexano 7, chloride Salt-based solvents such as methylene, chloroform, trichloroethylene, tetrahydrofuran, dioxane are ether%i, N, N
- Organic solvents such as dimethylformamide and N-methylpyrrolidone can be mentioned.
＋Ｅ 写シー ト作製のためθ）インクを塗布するベー
スフィルムとしてハ、コンデンサーｉ。+E Photography sheet θ) As a base film for applying ink, Capacitor i.
グラシン紙のような薄葉紙、ポリエステル。Thin paper like glassine paper, polyester.
ポリアミド、ポリイミドのような耐臥住の良好なプラス
チックのフィルムが適しているが。Films made of plastics with good sagging resistance, such as polyamide or polyimide, are suitable.
それらの厚さとしては、３〜よ０μｍの範囲を挙げるこ
とができる。Their thickness can range from 3 to 0 μm.
イ７り’１ベースフィルムに塗布する方法とシテハ、リ
バースロールコータ−、グラビアコーター、ロッドコー
ター、エアトクタコーの範囲となるよう塗布すれば良い
（原崎勇次著、槙書店、ｉｑ’ｙｑ年発行「コーティン
グ１式゛」）。How to apply the coating to the base film and how to apply it using the Shiteha, reverse roll coater, gravure coater, rod coater, or airtocco. 1 type ゛'').
発明の作用及び効果
系色素は鮮明なシアン色を脣するため、適由なマゼンタ
色およびイエロー色と組み合せることにより色再現性の
良好なフルカラー記録を得るのに適しており又昇華し易
（、分子吸光係数が大きいため感熱ヘッドに大きな負担
をかけることなく、高速で色濃度の高い記録を得ること
ができる。更に熱、光、湿気、薬品などに対して安定で
あるため、転写記録中に熱分解すること 。Functions and Effects of the Invention Since the dye has a clear cyan color, it is suitable for obtaining a full-color record with good color reproducibility by combining it with appropriate magenta and yellow colors, and is easy to sublimate ( Because of its large molecular extinction coefficient, it is possible to obtain high-speed recording with high color density without placing a large burden on the thermal head.Furthermore, it is stable against heat, light, moisture, chemicals, etc., so it can be used during transfer recording. to be pyrolyzed into .
な（、得られた記録の保存性も優れている。又本発明の
色素は有機溶剤に対する溶解性及び水に対する分散性が
良好であるため均一に溶解あるいは分散した高濃度のイ
ンクを調製することが容易でありそれらのインクを用い
ることにより１色素が均一に高濃度で゛塗布された転写
シートを得ることができる。したがって、それらの転写
シー）Ｙ用いることにより均−性及び色濃度の良好な記
録暑得ることができる。(The storage stability of the obtained records is also excellent.Also, since the dye of the present invention has good solubility in organic solvents and good dispersibility in water, it is possible to prepare a highly concentrated ink that is uniformly dissolved or dispersed.) By using these inks, it is possible to obtain a transfer sheet coated with one dye uniformly and at a high concentration. Therefore, by using these transfer sheets, it is possible to obtain good uniformity and color density. You can get record heat.
実施例
以下実施例によりこの発明ン具体的に説明するが、かか
る実施例は本発明を限定するものではない。EXAMPLES The present invention will be explained in detail with reference to Examples below, but these Examples are not intended to limit the present invention.
実施例！
ａ）色素の製造
下記構造式
で表わされるλ、３−とスーアセトアｉドーフェノール
ｕ、／ｆｌと下記構造式
で表わされる化付物！、Ｊｆ／にエタノール３００ｍ／
Ｙ ７１［１え、室温で攪拌し１次いで、硝酸銀、ｙ
、ｔｔｇ暑水１３ｍ１に溶解させた水溶ｇ、’に滴下し
た。２１％アンモニア水１５ｍ１をフロえ、さらに硝酸
銀ｔｏ、ｒｇｙｌ水ｔｏｍｌに溶解させた水溶ｇ、を滴
下し、３Ｑ〜ａＯ℃で３時間反応 ′させた、反
応終了後、クロロホルム抽出し、９媒留去後、クロロホ
ルムでカラム精製を行ない、下記構造式
で表わされるインドアニリン系色素の精製品”２ ｊ、
７ ｇ得た。ｃ対理収率りｇ％ノ上記色素のマススペ
クトルはｍ／ｅ ＝ Ｊ Ａ ｔであり、極大吸収波長
は＆、？４！ｎｍ（クロロホルムノであった。Example! a) Production of dyes λ, 3- and Suacetoidophenol u,/fl represented by the following structural formula and an adduct represented by the following structural formula! , Jf/ to ethanol 300m/
Y 71 [1st, stirred at room temperature, then silver nitrate, y
, ttg was added dropwise to the aqueous solution g,' dissolved in 13 ml of hot water. Float 15 ml of 21% ammonia water, add dropwise silver nitrate and aqueous solution g dissolved in rgyl water to ml, and react at 3Q~aO℃ for 3 hours. After the reaction is complete, extract with chloroform and remove with 9 mortar. After that, column purification was performed using chloroform to obtain a purified product of indoaniline dye represented by the following structural formula.
I got 7g. The mass spectrum of the above dye is m/e = J At, and the maximum absorption wavelength is &, ? 4! nm (chloroform).
ｂ）インクの調製
Ｎ３（ｊｔＪＬ；ａｊｌ
上記色素 ｌｏｇ
ポリスルホン樹脂※ ｔ０９
クロロベンゼン ざｏｆ！
合計 ｉｏｏｇ
※ 日産化学工業株式会社製造、ニーデルＰ−１７００
ｃ商品名）
上記組成の混合物ｔペイントコンディショナーで７０分
間処理し、インクの調！！ｌ’行なった。色素及び樹脂
は完全に溶解し、均一な溶液のインキｌ得ることができ
た。b) Preparation of ink N3 (jtJL; ajl Above dye log Polysulfone resin * t09 Chlorobenzene Zaof! Total ioog * Manufactured by Nissan Chemical Industries, Ltd., Needel P-1700
C Product name) Treat the mixture with the above composition with paint conditioner for 70 minutes to condition the ink! ! I did it. The pigment and resin were completely dissolved, and a uniform solution of the ink could be obtained.
Ｃ）転写シートの作製
上記のインクχバーコーター（ＲＫ Ｐｒ１ｎｔｃｏａ
ｔ工ｎａｔｒｕｍｅｎｔｓ社製／Ｆ５ ／ Ｊ Ｙ用い
てポリイミドフィルム（／ｊμｍ厚〕上に塗布した後、
自然乾燥して転写シート？得た。C) Preparation of transfer sheet The above ink χ bar coater (RK Pr1ntcoa
After applying it on a polyimide film (/μm thick) using F5/JY manufactured by T-Natruments,
Air dry and transfer sheet? Obtained.
ｄ）転写記録
上記転写シートのインク塗布面を被記録体と重ね感熱ヘ
ッドを用い下記条件で記録し、鮮明なシアン色でｉ、３
ｏの均一で高、い色濃度の記録を得ることができた。d) Transfer recording The ink-applied surface of the above transfer sheet was placed on the recording medium and recorded using a thermal head under the following conditions, with a clear cyan color i, 3.
It was possible to obtain a record of uniform high color density of o.
記録条件
主走査、副走査の線密度：４ｔドツト／闘記録電力
：（７，４Ｗ／ドツトヘツドの方り熱時
間 ：１０ｍａθＣなお、被記録体は、飽和ポリエ
ステル、７４を重量俤の水分散液（東洋紡績株式会社製
造。Recording conditions Main scanning and sub-scanning linear density: 4t dots/recording power
: (7.4 W/dotted head heating time: 10 maθC) The recording medium is a saturated polyester, an aqueous dispersion of 74 (manufactured by Toyobo Co., Ltd.).
バイロナー）ｖ ＭＤ−１２００，商品名）１０１とシ
リカ（日本シリカニ業株式会社製造。Vyloner) v MD-1200, trade name) 101 and silica (manufactured by Nippon Silikani Gyo Co., Ltd.).
Ｎ１ｐｓｉｌ Ｆ２２２ｏＡ、 商品名）／ｇ’を混
合し調製した？Ｗ’に上質紙（コＯＱμｍ厚）にバーコ
ーター （ＲＫ Ｐｉｎｔ ＣｏａｔＩｎａｔｒｕｍｅ
ｎｔｓ社製造。Was it prepared by mixing N1psil F222oA, trade name)/g'? Bar coater (RK Pint Coat Inatrume) on high quality paper (OQμm thickness) on W'
Manufactured by nts.
Ａ ３ ） ’ｒ：用いて塗布後、乾燥して製造したも
のである。A3) 'r: Manufactured by applying and drying.
色濃度は、米国マクベス社共造、デンシトメーターＨＤ
−ｊ／Ｑ型（フィルター：ラッテン扁コよ）？用いて測
定した。Color density is measured using a densitometer HD, co-produced by Macbeth Co., Ltd.
-J/Q type (filter: ratten flat)? It was measured using
得られた記録のｌｌｌｉｔ元性試験ｔカーボンアークフ
ェードメーター（スガ試験機社製造）χ用いて実施（ブ
ラックパネル温度す、ｙ−にユ℃）したが４０時間の照
射後はとんど変退色しなかった。また、転写シートおよ
び記録は熱。The originality test of the obtained records was carried out using a carbon arc fade meter (manufactured by Suga Test Instruments Co., Ltd.) (black panel temperature: y- to ℃), but after 40 hours of irradiation, the color almost changed and faded. I didn't. Also, the transfer sheet and recording are heated.
湿気に対して安定であり、暗所保存性にすぐれていた◎
実施例コ
実施例１で用いた色素のかわりに第１表に示す色素を用
い実施例１と同様の方法でインクの調製、転写シートの
作製、転写記録を莢施した結果、各々第１表に示す色濃
度の鮮明なシアン色の配分暑得ることができた。It was stable against moisture and had excellent storage stability in the dark. ◎ Example Co. Ink was prepared in the same manner as in Example 1 using the pigments shown in Table 1 instead of the pigments used in Example 1. As a result of preparing the transfer sheet and performing the transfer recording, it was possible to obtain a clear cyan color distribution with the color density shown in Table 1.
得られた記録の耐光性試験および転写シート・記録の暗
所保存性試験の結果は良好であった。The results of the light fastness test of the obtained record and the dark storage stability test of the transfer sheet/record were good.
Claims (4)
てもよいアルキル基、アルコキシ基、ホルミルアミノ基
、フツ素原子により置換されていてもよいアルキルカル
ボニルアミノ基、アリールカルボニルアミノ基又はハロ
ゲン原子を表わし、Ｙは水素原子、フツ素原子により置
換されていてもよいアルキル基、アルコキシ基又はハロ
ゲン原子を表わし、Ｒ＾１およびＲ＾２は水素原子、Ｃ
＿１＿〜＿８の置換もしくは非置換のアルキル基を表わ
し、Ｒ＾３およびＲ＾４は▲数式、化学式、表等があり
ます▼、▲数式、化学式、表等があります▼、▲数式、
化学式、表等があります▼、▲数式、化学式、表等があ
ります▼、 ▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼、▲数式、化学式、表等があります▼
、▲数式、化学式、表等があります▼、 ▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼、▲数式、化学式、表等があります▼
を表わし、Ｒ＾５およびＲ＾６はＣ＿１＿〜＿８の置換
もしくは非置換のアルキル基を表わす） で示されるインドアニリン系化合物。(1) General formula [I] ▲Mathematical formulas, chemical formulas, tables, etc.▼......[I] (In the formula, X is a hydrogen atom, an alkyl group optionally substituted with a fluorine atom, an alkoxy group, formyl represents an amino group, an alkylcarbonylamino group optionally substituted with a fluorine atom, an arylcarbonylamino group, or a halogen atom, and Y is a hydrogen atom, an alkyl group optionally substituted with a fluorine atom, an alkoxy group, or a halogen Represents an atom, R^1 and R^2 are hydrogen atoms, C
_1_-_8 represents a substituted or unsubstituted alkyl group, and R^3 and R^4 are ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲Mathematical formulas,
There are chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
and R^5 and R^6 represent substituted or unsubstituted alkyl groups of C_1_-_8).
合物において、ＸおよびＹが水素原子、メチル基、メト
キシ基、エトキシ基、塩素原子、臭素原子又はトリフル
オロメチル基を示し、Ｒ＾１およびＲ＾２が水素原子、
ヒドロキシアルキル基、アラルキル基又はＣ＿１＿〜＿
６のアルキル基を示し、Ｒ＾３およびＲ＾４が▲数式、
化学式、表等があります▼、▲数式、化学式、表等があ
ります▼、▲数式、化学式、表等があります▼、▲数式
、化学式、表等があります▼、▲数式、化学式、表等が
あります▼、▲数式、化学式、表等があります▼、 ▲数式、化学式、表等があります▼又は▲数式、化学式
、表等があります▼を示し、Ｒ＾５およびＲ＾６がＣ＿
１＿〜＿４のアルキル基又はハロゲン化アルキル基で示
される化合物。(2) In the indoaniline compound according to claim 1, X and Y represent a hydrogen atom, a methyl group, a methoxy group, an ethoxy group, a chlorine atom, a bromine atom, or a trifluoromethyl group, and R^1 and R^2 is a hydrogen atom,
Hydroxyalkyl group, aralkyl group or C_1_～_
6 alkyl group, R^3 and R^4 are ▲ formula,
There are chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or ▲There are mathematical formulas, chemical formulas, tables, etc.▼, and R^5 and R^6 are C_
A compound represented by an alkyl group or a halogenated alkyl group of 1_ to_4.
てもよいアルキル基、アルコキシ基、ホルミルアミノ基
、フツ素原子により置換されていてもよいアルキルカル
ボニルアミノ基、アリールカルボニルアミノ基又はハロ
ゲン原子を表わし、Ｙは水素原子、フツ素原子により置
換されていてもよいアルキル基、アルコキシ基又はハロ
ゲン原子を表わし、Ｒ＾１およびＲ＾２は水素原子、Ｃ
＿１＿〜＿８の置換もしくは非置換のアルキル基を表わ
し、Ｒ＾３およびＲ＾４は▲数式、化学式、表等があり
ます▼、▲数式、化学式、表等があります▼、▲数式、
化学式、表等があります▼、▲数式、化学式、表等があ
ります▼、 ▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼、▲数式、化学式、表等があります▼
、▲数式、化学式、表等があります▼、 ▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼、▲数式、化学式、表等があります▼
を表わし、Ｒ＾５およびＲ＾６はＣ＿１＿〜＿８の置換
もしくは非置換のアルキル基を表わす） で示される感熱転写記録用色素。(3) General formula [I] ▲Mathematical formulas, chemical formulas, tables, etc.▼......[I] (In the formula, X is a hydrogen atom, an alkyl group optionally substituted with a fluorine atom, an alkoxy group, formyl represents an amino group, an alkylcarbonylamino group optionally substituted with a fluorine atom, an arylcarbonylamino group, or a halogen atom, and Y is a hydrogen atom, an alkyl group optionally substituted with a fluorine atom, an alkoxy group, or a halogen Represents an atom, R^1 and R^2 are hydrogen atoms, C
_1_-_8 represents a substituted or unsubstituted alkyl group, and R^3 and R^4 are ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲Mathematical formulas,
There are chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
and R^5 and R^6 represent substituted or unsubstituted alkyl groups of C_1_-_8).
において、ＸおよびＹが水素原子、メチル基、メトキシ
基、エトキシ基、塩素原子、臭素原子又はトリフルオロ
メチル基を示し、Ｒ＾１およびＲ＾２が水素原子、ヒド
ロキシアルキル基、アラルキル基又はＣ＿１＿〜＿６の
アルキル基を示し、Ｒ＾３およびＲ＾４が▲数式、化学
式、表等があります▼、▲数式、化学式、表等がありま
す▼、▲数式、化学式、表等があります▼▲数式、化学
式、表等があります▼、▲数式、化学式、表等がありま
す▼、▲数式、化学式、表等があります▼、▲数式、化
学式、表等があります▼又は ▲数式、化学式、表等があります▼を示し、Ｒ＾５およ
びＲ＾６がＣ＿１＿〜＿４のアルキル基又はハロゲン化
アルキル基で示される色素。(4) In the dye for thermal transfer recording according to claim 3, X and Y represent a hydrogen atom, a methyl group, a methoxy group, an ethoxy group, a chlorine atom, a bromine atom, or a trifluoromethyl group, and R^ 1 and R^2 represent a hydrogen atom, a hydroxyalkyl group, an aralkyl group, or an alkyl group of C_1_-_6, and R^3 and R^4 have ▲a mathematical formula, a chemical formula, a table, etc.▼, ▲a mathematical formula, a chemical formula, a table, etc. There are ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas , chemical formula, table, etc. ▼ or ▲ Numerical formula, chemical formula, table, etc. available ▼, and R^5 and R^6 are C_1_-_4 alkyl groups or halogenated alkyl groups.
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59181230A JPS6157651A (en) | 1984-08-30 | 1984-08-30 | Indoaniline compounds, thermal transfer recording dyes, and thermal transfer recording sheets |
| DE19853524519 DE3524519A1 (en) | 1984-07-11 | 1985-07-09 | Dyes for heat-sensitive sublimation transfer recording |
| CA000486541A CA1283660C (en) | 1984-07-11 | 1985-07-09 | Dyes for sublimation heat-sensitive transfer recording |
| GB8517439A GB2161824B (en) | 1984-07-11 | 1985-07-10 | Dyes for sublimation heat-sensitive transfer recording |
| FR8510579A FR2567532B1 (en) | 1984-07-11 | 1985-07-10 | DYES FOR SUBLIMATION THERMAL TRANSFER RECORDING |
| US07/008,268 US4829047A (en) | 1984-07-11 | 1987-01-29 | Dye transfer sheet for sublimation heat-sensitive transfer recording |
| US07/696,929 USRE34737E (en) | 1984-07-11 | 1991-05-08 | Dye transfer sheet for sublimation heat-sensitive transfer recording |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59181230A JPS6157651A (en) | 1984-08-30 | 1984-08-30 | Indoaniline compounds, thermal transfer recording dyes, and thermal transfer recording sheets |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6157651A true JPS6157651A (en) | 1986-03-24 |
Family
ID=16097077
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59181230A Withdrawn JPS6157651A (en) | 1984-07-11 | 1984-08-30 | Indoaniline compounds, thermal transfer recording dyes, and thermal transfer recording sheets |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6157651A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61268493A (en) * | 1985-05-23 | 1986-11-27 | Dainippon Printing Co Ltd | Thermal transfer sheet |
| JPS6264595A (en) * | 1985-09-18 | 1987-03-23 | Dainippon Printing Co Ltd | Heat transfer sheet |
| JPS62225564A (en) * | 1986-03-28 | 1987-10-03 | Dainippon Printing Co Ltd | Dye and heat transfer sheet using same |
| JP2008248125A (en) * | 2007-03-30 | 2008-10-16 | Fujifilm Corp | Indian aniline dye, thermal transfer recording ink sheet, thermal transfer recording method, color toner, inkjet ink, and color filter |
-
1984
- 1984-08-30 JP JP59181230A patent/JPS6157651A/en not_active Withdrawn
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61268493A (en) * | 1985-05-23 | 1986-11-27 | Dainippon Printing Co Ltd | Thermal transfer sheet |
| JPS6264595A (en) * | 1985-09-18 | 1987-03-23 | Dainippon Printing Co Ltd | Heat transfer sheet |
| JPS62225564A (en) * | 1986-03-28 | 1987-10-03 | Dainippon Printing Co Ltd | Dye and heat transfer sheet using same |
| JP2008248125A (en) * | 2007-03-30 | 2008-10-16 | Fujifilm Corp | Indian aniline dye, thermal transfer recording ink sheet, thermal transfer recording method, color toner, inkjet ink, and color filter |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |