JPH0462277B2 - - Google Patents
Info
- Publication number
- JPH0462277B2 JPH0462277B2 JP59153742A JP15374284A JPH0462277B2 JP H0462277 B2 JPH0462277 B2 JP H0462277B2 JP 59153742 A JP59153742 A JP 59153742A JP 15374284 A JP15374284 A JP 15374284A JP H0462277 B2 JPH0462277 B2 JP H0462277B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- recording
- represent
- dye
- group
- 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
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 238000004040 coloring Methods 0.000 claims description 2
- 239000000975 dye Substances 0.000 description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 239000011347 resin Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 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
- 239000000203 mixture 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
- 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 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
- 238000001035 drying Methods 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000123 paper Substances 0.000 description 3
- 229910001961 silver nitrate Inorganic materials 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 230000008033 biological extinction Effects 0.000 description 2
- 238000000576 coating method Methods 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
- 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
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000008018 melting Effects 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
- 239000002904 solvent Substances 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- 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
- 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
- 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
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 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
- 239000011248 coating agent Substances 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- -1 dioxane Chemical class 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
- 125000002887 hydroxy group Chemical group [H]O* 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
- 238000005259 measurement Methods 0.000 description 1
- 239000000113 methacrylic resin Substances 0.000 description 1
- KVHRISPSSMDQOB-UHFFFAOYSA-N n-(2-hydroxyphenyl)methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC=C1O KVHRISPSSMDQOB-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 239000002985 plastic film Substances 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
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 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
- 238000003756 stirring Methods 0.000 description 1
- 238000005092 sublimation method Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000547 substituted alkyl 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
- 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
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
素およびシートに関する。
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。
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を、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
色素をこの記録方式に適用する場合、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。
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。
熱、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。
本発明は上記の条件を全て満足するシアン色素
の提供をその目的とするものである。
また、その色素を用いる感熱転写記録用シート
を他の目的とするものである。
すなわち、本発明は、下記一般式〔〕
（式中、Ｘ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、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、
Y1，Y2，およびY3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、R1およびR2は水
素原子、C1-8の置換もしくは非置換のアルキル
基、アリル基又はアリール基を表わし、Ａは
OBJECTS OF THE INVENTION A. Field of Industrial Application The present invention relates to dyes and sheets used in sublimation type thermal transfer recording. 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 melting method in which a transfer sheet with a heat-melting ink layer formed on a base film is heated by a heat-sensitive head to melt the ink and transfer recording onto a recording medium; There is a sublimation method, in which a transfer sheet on which an ink layer containing a sublimable dye is formed is heated by a thermal head to sublimate the dye, and then transferred and recorded onto a recording medium. Since the amount of sublimation transfer of the dye can be controlled by changing the applied energy, gradation recording becomes easy and is considered to be particularly advantageous for full color recording. C. Problems to be Solved by the Invention When a dye is applied to this recording method, the dye must meet the following conditions. Easily sublimated under the operating conditions of a thermal recording head. Do not thermally decompose under the operating conditions of the thermal recording head. Must have a favorable hue in terms of color reproduction. High molecular extinction coefficient. Stable against heat, light, moisture, chemicals, etc. Easy to synthesize. Excellent ink suitability. An object of the present invention is to provide a cyan dye that satisfies all of the above conditions. Further, a heat-sensitive transfer recording sheet using the dye is intended for another purpose. That is, the present invention provides the following general formula [] (In the formula, represents an atom,
Y 1 , Y 2 , and Y 3 represent a hydrogen atom, an alkyl group optionally substituted with a fluorine atom, an alkoxy group, or a halogen atom, and R 1 and R 2 represent a hydrogen atom, a C 1-8 substituted or represents an unsubstituted alkyl group, allyl group or aryl group, and A is
【式】【formula】
【式】【formula】
【式】【formula】
【式】を表わし、R4および
R5はC1-8の置換もしくは非置換のアルキル基又
はアリール基を表わす。）
で示される感熱転写記録用インドアニリン系色素
及びそれを用いた感熱転写記録用シートをその要
旨とするものである。
式中、R1〜R5の置換アルキル基の置換基の例
としては、アルコキシ基、ヒドロキシ基、アリー
ル基等が挙げられる。
これら、本発明の色素の製造方法としては、た
とえば下記一般式〔〕
（式中、Ａ，Y2およびY3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、Y1，Ｘ，R1およびR2は前記定義に同
じ。）
で示されるアニリン類とを硝酸銀の存在下、加熱
することにより得られる。
本発明の色素の具体的な例としては、実施例に
示したものなどが挙げられるが、それらに限定さ
れるものではない。
特に好ましいものとしては、前記一般式〔〕
において、Ｘ，Y1，Y2およびY3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、R1お
よびR2が水素原子、ヒドロキシアルキル基、ア
ラルキル基又はC1〜6のアルキル基を示し、Ａが
[Formula] is represented, and R 4 and R 5 represent a C 1-8 substituted or unsubstituted alkyl group or aryl group. ) The gist of the invention is an indoaniline dye for thermal transfer recording shown in the following and a sheet for thermal transfer recording using the same. In the formula, examples of substituents for the substituted alkyl groups of R 1 to R 5 include an alkoxy group, a hydroxy group, an aryl group, and the like. As a method for producing these dyes of the present invention, for example, the following general formula [] (In the formula, A, Y 2 and Y 3 are the same as defined above.) Phenols represented by the following general formula [] (In the formula, Y 1 , X, R 1 and R 2 are the same as defined above.) It is obtained by heating the anilines represented by the following in the presence of silver nitrate. Specific examples of the dye of the present invention include those shown in Examples, but are not limited thereto. Particularly preferred is the general formula []
In , _ _ _ , represents an aralkyl group or a C 1-6 alkyl group, and A is
【式】【formula】
【式】又は[Formula] or
【式】を示し、R4およびR5がC1〜4のアル
キル基で示される色素が挙げられる。
本発明の他の目的である感熱転写記録用シート
は、基材上に本発明の色素を含有する色材層を設
けてなるものであつて、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、乾燥する等の方法で作製すること
ができる。
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
みな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−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が、それらの厚さとして
は３〜50μｍ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0.1〜5μｍの範囲となるよう塗布す
れば良い（原崎勇次著、槙書店1979年発行「コー
テイング方式」）。
発明の作用及び効果
本発明の前記〔〕で示されるインドアニリン
系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、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、均一な溶液のインキを
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No.１）を用いてポリイミ
ドフイルム（15μｍ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トツド／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を混合し調製した液を上質紙（200μｍ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
たものである。
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
いて実施（ブラツクパネル温度63±２℃）した
が、40時間の照射後ほとんど変退色しなかつた。
また、転写シートおよび記録は熱・湿気に対して
安定であり、暗所保存性にすぐれていた。
色素の製造は次のようにして行なつた。
下記構造式
で表わされる２−メチルスルホニルアミノ−フエ
ノール3.7ｇと下記構造式
で表わされる化合物5.24ｇにエタノール150mlを
加え、室温で攪拌し、次いで、硝酸銀3.4ｇを水
15mlに溶解させた水溶液を滴下した。28％アンモ
ニア水15mlを加え、さらに硝酸銀10.5ｇを水10ml
に溶解させた水溶液を滴下し、30〜40℃で３時間
反応させた。反応終了後、クロロホルム抽出し、
溶媒留去後、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5.27
ｇ得た。（対理収率76％）
上記色素の融点は135〜137℃、極大吸収波長は
640nm（クロロホルム中）であつた。
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。
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つた。Examples include dyes represented by the formula and in which R 4 and R 5 are C 1-4 alkyl groups. A heat-sensitive transfer recording sheet, which is another object of the present invention, is one in which a coloring material layer containing the dye of the present invention is provided on a base material. The ink can be prepared by dispersing it into fine particles, and then applying the 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 the ink for making the transfer sheet can be made of capacitor paper, thin paper such as glassine paper, polyester, polyamide,
Plastic films with good heat resistance such as polyimide are suitable, and their thickness may range from 3 to 50 .mu.m. The ink can be applied to the base film using a reverse roll coater, gravure coater, rod coater, air doctor coater, etc., and the thickness of the ink coating layer after drying is in the range of 0.1 to 5 μm. All you have to do is apply it so that it is coated ("Coating Method" by Yuji Harasaki, published by Maki Shoten in 1979). Functions and Effects of the Invention Since the indoaniline dye shown in [] above of the present invention has a clear cyan color, it is possible to obtain full-color recording with good color reproducibility by combining it with appropriate magenta and yellow colors. Furthermore, 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 obtained 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 The above dye 10g Polysulfone resin* 10g Chlorobenzene 80g Total 100g *Manufactured by Nissan Chemical Industries, Ltd., Udel P-1700 (trade name) A mixture of 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 applied onto a polyimide film (thickness: 15 μm) and 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 carried out using a thermal head under the following conditions, and it was possible to obtain a record of a clear cyan color 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 medium was an aqueous dispersion of 34% by weight saturated polyester (Toyobo Co., Ltd. Company manufactured by Vyronal
MD-1200, trade name) 10g and silica (manufactured by Nippon Silica Kogyo Co., Ltd., Nipsil E220A, trade name)
Mix 1 g of the prepared liquid and place it on high-quality paper (200 μm thick).
Bar coater (RK Print Coat Instruments)
The product was manufactured by coating and drying using No. 3, manufactured by Co., Ltd. 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 recording was carried out using a carbon arc fade meter (manufactured by Suga Test Instruments Co., Ltd.) (black panel temperature: 63±2° C.), and there was almost no discoloration or fading after 40 hours of irradiation.
Furthermore, the transfer sheet and the recording were stable against heat and moisture, and had excellent storage stability in the dark. The dye was produced as follows. Structural formula below 3.7g of 2-methylsulfonylamino-phenol represented by and the following structural formula Add 150 ml of ethanol to 5.24 g of the compound represented by and stir at room temperature, then add 3.4 g of silver nitrate to water.
An aqueous solution dissolved in 15 ml was added dropwise. Add 15ml of 28% ammonia water, then add 10.5g of silver nitrate to 10ml of water.
An aqueous solution dissolved in the solution was added dropwise, and the mixture was reacted at 30 to 40°C for 3 hours. After the reaction is completed, extract with chloroform,
After distilling off the solvent, column purification was performed using chloroform, and the following structural formula was obtained. Purified product of indoaniline dye expressed by 5.27
I got g. (Yield: 76%) The melting point of the above dye is 135-137℃, and the maximum absorption wavelength is
640 nm (in chloroform). 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 in the same manner as in Example 1. As a result, the results were as shown in Table 1. It was possible to obtain a clear cyan color record with the indicated color density. Lightfastness test of the obtained recording and transfer sheet
The results of the dark storage stability test of the records were good.
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】
＊クロロホルム中の測定値を示す。
[Table] *Measurement values in chloroform are shown.
Claims (1)
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、
Y1，Y2，およびY3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、R1およびR2は水
素原子、C1-8の置換もしくは非置換のアルキル
基、アリル基又はアリール基を表わし、Ａは
【式】【式】 【式】【式】【式】 【式】【式】【式】 【式】【式】を表わし、R4および R5はC1-8の置換もしくは非置換のアルキル基又
はアリール基を表わす。） で示される感熱転写記録用色素。 ２ 基材上に下記一般式で表わされる色素を含有
している色材層を有することを特徴とする感熱転
写記録用シート。 一般式 （式中、Ｘ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、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、
Y1，Y2，およびY3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、R1およびR2は水
素原子、C1-8の置換もしくは非置換のアルキル
基、アリル基又はアリール基を表わし、Ａは
【式】【式】 【式】【式】【式】 【式】【式】【式】 【式】【式】を表わし、R4および R5はC1-8の置換もしくは非置換のアルキル基又
はアリール基を表わす。）[Claims] 1. General formula (In the formula, represents an atom,
Y 1 , Y 2 , and Y 3 represent a hydrogen atom, an alkyl group optionally substituted with a fluorine atom, an alkoxy group, or a halogen atom, and R 1 and R 2 represent a hydrogen atom, a C 1-8 substituted or represents an unsubstituted alkyl group, allyl group or aryl group, A represents [formula] [formula] [formula] [formula] [formula] [formula] [formula] [formula] [formula] [formula]; 4 and R 5 represent a C 1-8 substituted or unsubstituted alkyl group or aryl group. ) A dye for thermal transfer recording. 2. A thermal transfer recording sheet characterized by having a coloring material layer containing a dye represented by the following general formula on a base material. general formula (In the formula, represents an atom,
Y 1 , Y 2 , and Y 3 represent a hydrogen atom, an alkyl group optionally substituted with a fluorine atom, an alkoxy group, or a halogen atom, and R 1 and R 2 represent a hydrogen atom, a C 1-8 substituted or represents an unsubstituted alkyl group, allyl group or aryl group, A represents [formula] [formula] [formula] [formula] [formula] [formula] [formula] [formula] [formula] [formula]; 4 and R 5 represent a C 1-8 substituted or unsubstituted alkyl group or aryl group. )
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15374284A JPS6131292A (en) | 1984-07-24 | 1984-07-24 | 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 |
|---|---|---|---|
| JP15374284A JPS6131292A (en) | 1984-07-24 | 1984-07-24 | Coloring matter for thermal transfer recording |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9933185A Division JPS6131467A (en) | 1985-05-10 | 1985-05-10 | Indoaniline compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6131292A JPS6131292A (en) | 1986-02-13 |
| JPH0462277B2 true JPH0462277B2 (en) | 1992-10-05 |
Family
ID=15569114
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15374284A Granted JPS6131292A (en) | 1984-07-11 | 1984-07-24 | Coloring matter for thermal transfer recording |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6131292A (en) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6490156A (en) * | 1987-09-29 | 1989-04-06 | Kao Corp | P-phenylenediamine derivative and its production |
| US4769360A (en) * | 1987-09-14 | 1988-09-06 | Eastman Kodak Company | Cyan dye-donor element for thermal dye transfer |
| JP2911548B2 (en) * | 1989-08-02 | 1999-06-23 | 大日本印刷株式会社 | Thermal transfer sheet |
| US4933226A (en) * | 1989-12-11 | 1990-06-12 | Eastman Kodak Company | Thermal print element comprising a magenta 3-aryl-2-arylazo-5-aminothiazole or aminothiophene dye stabilized with a cyan indoaniline dye |
| JP3004104B2 (en) * | 1991-11-01 | 2000-01-31 | コニカ株式会社 | Image recording method and image recording apparatus |
| JP2007283748A (en) | 2006-03-23 | 2007-11-01 | Fujifilm Corp | Optical recording medium and visible information recording method |
| EP2111999A1 (en) | 2007-01-26 | 2009-10-28 | Fujifilm Corporation | Optical recording medium, and visible information recording method |
| US8012909B2 (en) | 2007-03-27 | 2011-09-06 | Fujifilm Corporation | Heat-sensitive transfer image-forming method |
| US8129309B2 (en) | 2007-03-29 | 2012-03-06 | Fujifilm Corporation | Heat-sensitive transfer sheet for use in heat-sensitive transfer system and image-forming method using heat-sensitive transfer system |
| EP1974948A3 (en) | 2007-03-29 | 2012-02-08 | FUJIFILM Corporation | Image-forming method using heat-sensitive transfer system |
| US8119562B2 (en) | 2007-03-29 | 2012-02-21 | Fujifilm Corporation | Heat-sensitive transfer sheet and image-forming method using heat-sensitive transfer system |
| EP1980408A3 (en) | 2007-03-29 | 2011-10-26 | FUJIFILM Corporation | Heat-sensitive transfer sheet and image-forming method |
| 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 |
| JP2008273641A (en) | 2007-04-25 | 2008-11-13 | Fujifilm Corp | Cardboard cylinder for heat-sensitive transfer image-receiving sheet, roll shape machined article and image forming method of the sheet |
| US20090165938A1 (en) | 2007-12-28 | 2009-07-02 | Fujifilm Corporation | Method of forming image by heat-sensitive transfer system |
| JP5308692B2 (en) * | 2008-02-28 | 2013-10-09 | 富士フイルムファインケミカルズ株式会社 | Method for producing indoaniline dye |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57186744A (en) * | 1981-05-12 | 1982-11-17 | Fuji Photo Film Co Ltd | Heat developable color photosensitive material |
| JPS59124890A (en) * | 1982-12-30 | 1984-07-19 | Konishiroku Photo Ind Co Ltd | Heat-sensitive transfer sheet |
| JPS59156791A (en) * | 1983-02-26 | 1984-09-06 | Konishiroku Photo Ind Co Ltd | Image-receiving element for thermal transfer |
| JPS59182839A (en) * | 1983-04-01 | 1984-10-17 | Konishiroku Photo Ind Co Ltd | Colored resin composition |
| JPS60130735A (en) * | 1983-12-19 | 1985-07-12 | Konishiroku Photo Ind Co Ltd | Image receiving element for heat transfer |
| JPS6122993A (en) * | 1984-07-11 | 1986-01-31 | Mitsubishi Chem Ind Ltd | Coloring matter for thermal transfer recording |
-
1984
- 1984-07-24 JP JP15374284A patent/JPS6131292A/en active Granted
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57186744A (en) * | 1981-05-12 | 1982-11-17 | Fuji Photo Film Co Ltd | Heat developable color photosensitive material |
| JPS59124890A (en) * | 1982-12-30 | 1984-07-19 | Konishiroku Photo Ind Co Ltd | Heat-sensitive transfer sheet |
| JPS59156791A (en) * | 1983-02-26 | 1984-09-06 | Konishiroku Photo Ind Co Ltd | Image-receiving element for thermal transfer |
| JPS59182839A (en) * | 1983-04-01 | 1984-10-17 | Konishiroku Photo Ind Co Ltd | Colored resin composition |
| JPS60130735A (en) * | 1983-12-19 | 1985-07-12 | Konishiroku Photo Ind Co Ltd | Image receiving element for heat transfer |
| JPS6122993A (en) * | 1984-07-11 | 1986-01-31 | Mitsubishi Chem Ind Ltd | Coloring matter for thermal transfer recording |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6131292A (en) | 1986-02-13 |
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