JPH0513076B2 - - Google Patents
Info
- Publication number
- JPH0513076B2 JPH0513076B2 JP59143928A JP14392884A JPH0513076B2 JP H0513076 B2 JPH0513076 B2 JP H0513076B2 JP 59143928 A JP59143928 A JP 59143928A JP 14392884 A JP14392884 A JP 14392884A JP H0513076 B2 JPH0513076 B2 JP H0513076B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- atom
- methyl
- dye
- recording
- 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.)
- Expired - Lifetime
Links
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 8
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- -1 propionylamino group Chemical group 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 5
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 4
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
- 238000004040 coloring Methods 0.000 claims description 2
- 239000000975 dye Substances 0.000 description 20
- 239000011347 resin Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-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
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
- 239000010410 layer Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000123 paper Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000008033 biological extinction Effects 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 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
- 239000000377 silicon dioxide Substances 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- OWNRRUFOJXFKCU-UHFFFAOYSA-N Bromadiolone Chemical compound C=1C=C(C=2C=CC(Br)=CC=2)C=CC=1C(O)CC(C=1C(OC2=CC=CC=C2C=1O)=O)C1=CC=CC=C1 OWNRRUFOJXFKCU-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
- 239000004952 Polyamide 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
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 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
- 239000011247 coating layer Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000011086 glassine Substances 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
- 239000007788 liquid Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000113 methacrylic resin Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 230000019612 pigmentation Effects 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920002647 polyamide 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
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000005092 sublimation method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
Landscapes
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Thermal Transfer Or Thermal Recording In General (AREA)
Description
発明の目的
イ 産業上の利用分野
本発明は、昇華型感熱転写記録に使用される色
素及びそれを用いた感熱転写記録用シートに関す
る。
ロ 従来の技術
従来、フアクシミリプリンター、複写機あるい
は、テレビ画像等をカラー記録する技術が要望さ
れ、電子写真、インクジエツト、感熱転写等によ
るカラー記録技術が検討されている。
感熱転写記録方式は、装置の保守が操作が容易
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。
感熱転写方式には、ベースフイルム上に熱溶融
性インク層を形成させた転写シート、感熱ヘツド
により加熱して、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、ベースフイルム上に
昇華性色素を含有するインク層を形成させた転写
シートを、感熱ヘツ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、昇華方式は感熱ヘツドに与えるエネルギー
を変えるエネルギーを変えることにより色素の昇
華転写量を制御することができるので、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。
ハ 発明が解決しようとする問題点
本発明は感熱記録ヘツドの作動条件で容易に昇
華すること、感熱記録ヘツドの作動条件で熱分解
しないこと、色再現上、好ましい色相を有するこ
と、分子吸光係数が大きいこと、光、湿気、薬品
などに対して安定なこと、合成が容易なこと、イ
ンク化適性が優れていること等の条件を満足する
シアン色素の提供をその目的とし、また他の目的
は該色素を用いた感熱転写記録用シートに関する
ものである。
発明の構成
本発明は、一般式〔〕
(式中、Xは水素原子、メチル基、メトキシ
基、ホルミルアミノ基、アセチルアミノ基、プロ
ピオニルアミノ基、塩素原子、臭素原子、ヨウ素
原子又はフツ素原子を表わし、Yは水素原子、メ
トキシ基、エトキシ基、塩素原子、臭素原子、ヨ
ウ素原子、フツ素原子又はメチル基を表わし、
R,R1およびR2は水素原子、置換もしくは非置
換のC1〜C8のアルキル基又はアリール基を表す。
但しN−〔3−〔{4−(N,N−ジエチルアミノ)
−2−メチル}フエニル〕イミノ−6−オキソ−
1,4−シクロヘキサジエン−1−イル〕アセト
アミドを除く。
で示される感熱転写記録用色素をその要旨とする
ものである。
すなわち本発明の色素は上記一般式〔〕で示
される色素である。
一般式〔〕においてR,R1およびR2で示さ
れる基としては、水素原子、C1〜C8のアルキル
基、C3〜C8のアルコキシアルキル基、C2〜C4の
ヒドロキシアルキル基、C1〜C8のハロゲン化ア
ルキル基、〓−シアノエチル基、アリル基又はテ
トラヒドロフルフリル基が好ましい。この他R1
及びR2としては、ベンジル基、〓−フエニルエ
チル基、〓−フエノキシエチル基、C4〜C8の〓
−アシルオキシエチル基、C4〜C8の〓−アルコ
キシカルボニルエチル基、C4〜C8の〓−アルコ
キシカルボニルオキシエチル基、フエニル基が同
様に好ましい。但し、本発明の色素はN−〔3−
〔{4−(N,N−ジエチルアミノ)−2−メチル}
フエニル〕イミノ−6−オキソ−1,4−シクロ
ヘキサジエン−1−イル〕アセトアミドで示され
る下記の構造式で示される色素は除外される。
そして、本発明の色素は、下記一般式〔〕
(式中、Rは前記定義に同じ。)
で示されるフエノール類と下記一般式〔〕
(式中、X,Y,R1,R2は前記定義に同じ。)
で表わされるアニリン類とを、硝酸銀の存在下、
加熱することにより製造することができる。
本発明の色素を含有する色材層を基材上に有す
る本発明の感熱転写記録用シートは、例えば色素
を結着剤とともに媒体中に溶解あるいは微粒子状
に分散させることによりインクを調製し該インク
をベースフイルム上に塗布、乾燥し転写シートを
作製すればよい。
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、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有機溶剤
に可溶性の樹脂などを挙げることができる。有機
溶剤可溶性の樹脂の場合有機溶剤溶液としてのみ
らず水性分散液の形で使用することも可能であ
る。
インク調製のための媒体としては水の他に、メ
チルアルコール、イソプロピルアルコール、イソ
ブチルアルコールなどのアルコール類、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、クロロベンゼンなどの
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、シクロヘキサノンなどのケトン
類、塩化メチレン、クロロホルム、トリクロロエ
チレンなどの塩素系溶剤、テトラヒドロフラン、
ジオキサンなどのエーテル類、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。
転写シート作製のためのインクを塗布するベー
スフイルムとしては、コンデンサー紙、グラシン
紙のような薄葉紙、ポリエステル、ポリアミド、
ポリイミドのような耐熱性の良好なプラスチツク
のフイルムが適している。また、該ベースフイル
ムの厚さとしては、3〜50〓mの範囲を挙げるこ
とができる。
インクをベースフイルムに塗布する方法として
は、リバースロールコーター、グラビアコータ
ー、ロツドコーター、エアドクタコーターなどを
使用して実施することができ、インキの塗布層の
厚さは乾燥後、0.1〜5〓mの範囲となるよう塗
布すれば良い(原崎勇次、「コーテイング方式」
(1979)槙書店)。
発明の作用及び効果
本発明の前記〔〕で示される色素は鮮明なシ
アン色を有するため、適当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
華し易く、分子吸光係数が大きいため感熱ヘツド
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なく、得られる記録の保存性
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、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。したがつ
て、それらの転写シートを用いることにより均一
性及び色濃度の良好な記録を得ることができる。
実施例
以下実施例によりこの発明を具体的に説明する
がかかる実施例は本発明を限定するものではな
い。
実施例 1
a インクの調製
上記色素 10g
ポリスルホン樹脂* 10gクロロベンゼン 80g
合計 100g
* 日産化学工業株式会社製造、ユーデルP−
1700(商品名)
上記組成の混合物をペイントコンデイシヨナー
で10分間処理し、インクの調製を行なつた。色素
及び樹脂は完全に溶解し、均一な溶液のインクを
得ることができた。
b 転写シートの作製
上記のインクをバーコーター(RK Print
Coat Instruments社製造、No.1)を用いてポリ
イミドフイルム(15〓m厚)上に塗布した後、自
然乾燥して転写シートを得た。
c 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
ね感熱ヘツドを用い下記条件で記録し、鮮明なシ
アン色で1.40の均一で高い色濃度の記録を得るこ
とができた。
記録条件
主走査、副走査の線密度 :4ドツト/mm
記録電力 :0.6W/ドツト
ヘツドの加熱時間 :10msec
なお、被記録体は、飽和ポリエステル34重量%
の水分散液(東洋紡績株式会社製造、バイロナー
ルMD−1200、商品名)10gとシリカ(日本シリ
カ工業株式会社製造、Nipsil E220A、商品名)
1gとを混合し調製した液を上質紙(200〓m厚)
にバーコーター(RK Print Coat Instruments
社製造、No.3)を用いて塗布後、乾燥して製造し
た。
色濃度は、米国マクベス社製造、デンシトメー
ターRD−514型(フイルター:ラツテンNo.25)
を用いて測定した。
得られた記録の耐光性試験をカーボンアークフ
エードメーター(スガ試験機株式会社製造)を用
いてブラツクパネル温度63±2℃で実施したが40
時間の照射後ほとんど変退色しなかつた。
実施例 2
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の方法に従つてインクの
調製、転写シートの作製、及び転写記録を実施し
た結果、各々第1表に示す色濃度の鮮明なシアン
色の記録を得ることができた。
OBJECT OF THE INVENTION A. Field of Industrial Application The present invention relates to a dye used in sublimation type heat-sensitive transfer recording and a heat-sensitive transfer recording sheet using the same. B. Prior Art Conventionally, there has been a demand for technology for color recording facsimile printers, copying machines, television images, etc., and color recording technologies using electrophotography, inkjet, thermal transfer, etc. are being considered. The thermal transfer recording method is considered to be advantageous over other methods because the device is easy to maintain and operate, and the device and consumables are inexpensive. Thermal transfer methods include a transfer sheet in which a heat-melting ink layer is formed on a base film, and a melting method in which a transfer sheet is heated with a heat-sensitive head to melt the ink and transferred onto a recording medium, and a transfer sheet is formed on a base film. There is a sublimation method in which a transfer sheet on which an ink layer containing a sublimable dye is formed is heated with a thermal head to sublimate the dye and transfer it onto the recording medium. Since the amount of sublimation transfer of the dye can be controlled by changing the energy, gradation recording becomes easy and it is considered to be particularly advantageous for full color recording. C. Problems to be Solved by the Invention The present invention is characterized in that it sublimates easily under the operating conditions of a thermal recording head, does not thermally decompose under the operating conditions of a thermal recording head, has a hue favorable for color reproduction, and has a molecular extinction coefficient. The purpose is to provide a cyan dye that satisfies the following conditions: large pigmentation, stability against light, moisture, chemicals, etc., easy synthesis, excellent suitability for ink production, and other purposes. relates to a heat-sensitive transfer recording sheet using the dye. Structure of the invention The present invention is based on the general formula [] (In the formula, X represents a hydrogen atom, a methyl group, a methoxy group, a formylamino group, an acetylamino group, a propionylamino group, a chlorine atom, a bromine atom, an iodine atom, or a fluorine atom, and Y represents a hydrogen atom, a methoxy group, Represents an ethoxy group, chlorine atom, bromine atom, iodine atom, fluorine atom or methyl group,
R, R 1 and R 2 represent a hydrogen atom, a substituted or unsubstituted C 1 to C 8 alkyl group, or an aryl group.
However, N-[3-[{4-(N,N-diethylamino)
-2-methyl}phenyl]imino-6-oxo-
1,4-Cyclohexadien-1-yl]acetamide is excluded. The gist is the dye for thermal transfer recording shown in the following. That is, the dye of the present invention is a dye represented by the above general formula []. In the general formula [], the groups represented by R, R 1 and R 2 include a hydrogen atom, a C 1 to C 8 alkyl group, a C 3 to C 8 alkoxyalkyl group, and a C 2 to C 4 hydroxyalkyl group. , a C1 - C8 halogenated alkyl group, a -cyanoethyl group, an allyl group, or a tetrahydrofurfuryl group. Other R 1
and R 2 is a benzyl group, a phenylethyl group, a phenoxyethyl group, a C 4 to C 8
-acyloxyethyl group, C4 - C8 〓-alkoxycarbonylethyl group, C4 - C8 〓-alkoxycarbonyloxyethyl group, and phenyl group are similarly preferred. However, the dye of the present invention is N-[3-
[{4-(N,N-diethylamino)-2-methyl}
Phenyl]imino-6-oxo-1,4-cyclohexadien-1-yl]acetamide dyes represented by the following structural formula are excluded. The dye of the present invention has the following general formula [] (In the formula, R is the same as defined above.) Phenols represented by the following general formula [] (In the formula, X, Y, R 1 and R 2 are the same as defined above.) In the presence of silver nitrate,
It can be manufactured by heating. The thermal transfer recording sheet of the present invention having a coloring material layer containing the dye of the present invention on a base material can be prepared by preparing an ink by dissolving or dispersing the dye in the form of fine particles in a medium together with a binder. A transfer sheet may be prepared by applying ink onto a base film and drying it. Binders for ink preparation include water-soluble resins such as cellulose, acrylic acid, and starch, and organic solvent-soluble resins such as acrylic resin, methacrylic resin, polystyrene, polycarbonate, polysulfone, polyethersulfone, and ethyl cellulose. Examples include resin. In the case of an organic solvent-soluble resin, it is possible to use it not only as an organic solvent solution but also in the form of an aqueous dispersion. In addition to water, media for ink preparation include alcohols such as methyl alcohol, isopropyl alcohol, and isobutyl alcohol, cellosolves such as methyl cellosolve and ethyl cellosolve, aromatics such as toluene, xylene, and chlorobenzene, ethyl acetate, Esters such as butyl acetate, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone, chlorinated solvents such as methylene chloride, chloroform, and trichloroethylene, tetrahydrofuran,
Examples include ethers such as dioxane, and organic solvents such as N,N-dimethylformamide and N-methylpyrrolidone. The base film used to apply ink for the production of transfer sheets includes condenser paper, thin paper such as glassine paper, polyester, polyamide,
A plastic film with good heat resistance, such as polyimide, is suitable. Further, the thickness of the base film may be in the range of 3 to 50 m. The ink can be applied to the base film using a reverse roll coater, gravure coater, rod coater, air doctor coater, etc. The thickness of the ink coating layer after drying is 0.1 to 5 mm. (Yuji Harasaki, "Coating method")
(1979) Maki Shoten). Functions and Effects of the Invention Since the dye shown in [] above of the present invention has a clear cyan color, it is suitable for obtaining full-color recording with good color reproducibility by combining it with appropriate magenta and yellow colors. Moreover, since it sublimes easily and has a large molecular extinction coefficient, it is possible to obtain high-speed recording with high color density without placing a large burden on the heat-sensitive head. Furthermore, since it is stable against heat, light, moisture, chemicals, etc., it does not undergo thermal decomposition during transfer recording, and the resulting recording has excellent storage stability. Furthermore, since the dye of the present invention has good solubility in organic solvents and good dispersibility in water, it is easy to prepare a uniformly dissolved or dispersed ink with high concentration, and by using such ink, , it is possible to obtain a transfer sheet on which the dye is uniformly coated at a high concentration. Therefore, by using these transfer sheets, recording with good uniformity and color density can be obtained. EXAMPLES The present invention will be specifically explained below with reference to Examples, but these Examples are not intended to limit the present invention. Example 1 a Preparation of ink Above dye 10g Polysulfone resin * 10g Chlorobenzene 80g Total 100g * Manufactured by Nissan Chemical Industries, Ltd., Udel P-
1700 (trade name) A mixture having the above composition was treated with a paint conditioner for 10 minutes to prepare an ink. The pigment and resin were completely dissolved, and an ink with a uniform solution could be obtained. b Preparation of transfer sheet Apply the above ink using a bar coater (RK Print
Coat Instruments Co., Ltd., No. 1) was used to coat a polyimide film (15 mm thick), and the transfer sheet was air-dried to obtain a transfer sheet. c. Transfer Recording The ink coated surface of the above transfer sheet was overlapped with the recording medium and recording was performed using a thermal head under the following conditions, and it was possible to obtain a clear cyan record with a uniform and high color density of 1.40. Recording conditions Main scanning and sub-scanning linear density: 4 dots/mm Recording power: 0.6 W/dot Head heating time: 10 msec The recording material is 34% by weight saturated polyester.
10 g of aqueous dispersion (manufactured by Toyobo Co., Ltd., Vylonal MD-1200, trade name) and silica (manufactured by Nippon Silica Kogyo Co., Ltd., Nipsil E220A, trade name)
Mix 1g of the prepared liquid with high-quality paper (200〓m thick)
Bar coater (RK Print Coat Instruments)
Co., Ltd., No. 3) was applied and dried. Color density was measured using a densitometer RD-514 model (filter: Ratten No. 25) manufactured by Macbeth, USA.
Measured using A light resistance test of the obtained record was conducted using a carbon arc fade meter (manufactured by Suga Test Instruments Co., Ltd.) at a black panel temperature of 63±2°C.
There was almost no discoloration or fading after irradiation for hours. Example 2 The dyes shown in Table 1 were used instead of the dyes used in Example 1, and ink preparation, transfer sheet production, and transfer recording were carried out according to the method of Example 1. A clear cyan color record with the color density shown in Table 1 could be obtained.
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
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【表】【table】
Claims (1)
基、ホルミルアミノ基、アセチルアミノ基、プロ
ピオニルアミノ基、塩素原子、臭素原子、ヨウ素
原子又はフツ素原子を表わし、Yは水素原子、メ
トキシ基、エトキシ基、塩素原子、臭素原子、ヨ
ウ素原子、フツ素原子又はメチル基を表わし、
R,R1およびR2は水素原子、置換もしくは非置
換のC1〜C8のアルキル基又はアリール基を表わ
す。但し、N−〔3−〔{4−(N,N−ジエチルア
ミノ)−2−メチル}フエニル〕イミノ−6−オ
キソ−1,4−シクロヘキサジエン−1−イル〕
アセトアミドを除く。) で示される感熱転写記録用色素。 2 基材上に一般式〔1〕 (式中、Xは水素原子、メチル基、メトキシ
基、ホルミルアミノ基、アセチルアミノ基、プロ
ピオニルアミノ基、塩素原子、臭素原子、ヨウ素
原子又はフツ素原子を表わし、Yは水素原子、メ
トキシ基、エトキシ基、塩素原子、臭素原子、ヨ
ウ素原子、フツ素原子又はメチル基を表わし、
R,R1およびR2は水素原子、置換もしくは非置
換のC1〜C8のアルキル基又はアリール基を表わ
す。但し、N−〔3−〔{4−(N,N−ジエチルア
ミノ)−2−メチル}フエニル〕イミノ−6−オ
キソ−1,4−シクロヘキサジエン−1−イル〕
アセトアミドを除く。) で示される色素を含有する色材層を設けてなる感
熱転写記録用シート。[Claims] 1 General formula [1] (In the formula, X represents a hydrogen atom, a methyl group, a methoxy group, a formylamino group, an acetylamino group, a propionylamino group, a chlorine atom, a bromine atom, an iodine atom, or a fluorine atom, and Y represents a hydrogen atom, a methoxy group, Represents an ethoxy group, chlorine atom, bromine atom, iodine atom, fluorine atom or methyl group,
R, R 1 and R 2 represent a hydrogen atom, a substituted or unsubstituted C 1 to C 8 alkyl group, or an aryl group. However, N-[3-[{4-(N,N-diethylamino)-2-methyl}phenyl]imino-6-oxo-1,4-cyclohexadien-1-yl]
Excludes acetamide. ) A dye for thermal transfer recording. 2 General formula [1] on the base material (In the formula, X represents a hydrogen atom, a methyl group, a methoxy group, a formylamino group, an acetylamino group, a propionylamino group, a chlorine atom, a bromine atom, an iodine atom, or a fluorine atom, and Y represents a hydrogen atom, a methoxy group, Represents an ethoxy group, chlorine atom, bromine atom, iodine atom, fluorine atom or methyl group,
R, R 1 and R 2 represent a hydrogen atom, a substituted or unsubstituted C 1 to C 8 alkyl group, or an aryl group. However, N-[3-[{4-(N,N-diethylamino)-2-methyl}phenyl]imino-6-oxo-1,4-cyclohexadien-1-yl]
Excludes acetamide. ) A heat-sensitive transfer recording sheet comprising a coloring material layer containing a dye represented by:
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP59143928A JPS6122993A (en) | 1984-07-11 | 1984-07-11 | Coloring matter for thermal transfer recording |
CA000486541A CA1283660C (en) | 1984-07-11 | 1985-07-09 | Dyes for sublimation heat-sensitive transfer recording |
DE19853524519 DE3524519A1 (en) | 1984-07-11 | 1985-07-09 | Dyes for heat-sensitive sublimation transfer recording |
FR8510579A FR2567532B1 (en) | 1984-07-11 | 1985-07-10 | DYES FOR SUBLIMATION THERMAL TRANSFER RECORDING |
GB8517439A GB2161824B (en) | 1984-07-11 | 1985-07-10 | Dyes for sublimation heat-sensitive 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 |
---|---|---|---|
JP59143928A JPS6122993A (en) | 1984-07-11 | 1984-07-11 | Coloring matter for thermal transfer recording |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS6122993A JPS6122993A (en) | 1986-01-31 |
JPH0513076B2 true JPH0513076B2 (en) | 1993-02-19 |
Family
ID=15350344
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP59143928A Granted JPS6122993A (en) | 1984-07-11 | 1984-07-11 | Coloring matter for thermal transfer recording |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS6122993A (en) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6131292A (en) * | 1984-07-24 | 1986-02-13 | Mitsubishi Chem Ind Ltd | Coloring matter for thermal transfer recording |
JPH0717107B2 (en) * | 1985-05-23 | 1995-03-01 | 大日本印刷株式会社 | Thermal transfer sheet |
JPH0798426B2 (en) * | 1985-09-18 | 1995-10-25 | 大日本印刷株式会社 | Thermal transfer sheet |
JPS6371393A (en) * | 1986-09-12 | 1988-03-31 | Matsushita Electric Ind Co Ltd | Transfer material for thermal transfer recording and thermal transfer recording method |
EP0285665B1 (en) * | 1986-10-07 | 1993-09-15 | Dai Nippon Insatsu Kabushiki Kaisha | Thermal transfer sheet |
JPS63199687A (en) * | 1987-02-16 | 1988-08-18 | Matsushita Electric Ind Co Ltd | Transfer material for thermal transfer recording |
JP2681781B2 (en) * | 1987-12-30 | 1997-11-26 | 大日本印刷株式会社 | Thermal transfer sheet |
JP3004104B2 (en) * | 1991-11-01 | 2000-01-31 | コニカ株式会社 | Image recording method and image recording apparatus |
JP5204418B2 (en) * | 2007-03-30 | 2013-06-05 | 富士フイルム株式会社 | Indian aniline dye, thermal transfer recording ink sheet, thermal transfer recording method, color toner, inkjet ink, and color filter |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6024996A (en) * | 1983-07-21 | 1985-02-07 | Konishiroku Photo Ind Co Ltd | Recording sheet for heat transfer recording medium |
-
1984
- 1984-07-11 JP JP59143928A patent/JPS6122993A/en active Granted
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6024996A (en) * | 1983-07-21 | 1985-02-07 | Konishiroku Photo Ind Co Ltd | Recording sheet for heat transfer recording medium |
Also Published As
Publication number | Publication date |
---|---|
JPS6122993A (en) | 1986-01-31 |
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Legal Events
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EXPY | Cancellation because of completion of term |