JPS6233688A - Dyestuff for thermal transfer recording - Google Patents

Dyestuff for thermal transfer recording

Info

Publication number
JPS6233688A
JPS6233688A JP60173877A JP17387785A JPS6233688A JP S6233688 A JPS6233688 A JP S6233688A JP 60173877 A JP60173877 A JP 60173877A JP 17387785 A JP17387785 A JP 17387785A JP S6233688 A JPS6233688 A JP S6233688A
Authority
JP
Japan
Prior art keywords
recording
coloring matter
group
ink
alkyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
JP60173877A
Other languages
Japanese (ja)
Inventor
Yukichi Murata
勇吉 村田
Shuichi Maeda
修一 前田
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Mitsubishi Kasei Corp
Original Assignee
Mitsubishi Kasei Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Mitsubishi Kasei Corp filed Critical Mitsubishi Kasei Corp
Priority to JP60173877A priority Critical patent/JPS6233688A/en
Publication of JPS6233688A publication Critical patent/JPS6233688A/en
Pending legal-status Critical Current

Links

Classifications

    • BPERFORMING OPERATIONS; TRANSPORTING
    • B41PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41MPRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00Duplicating or marking methods; Sheet materials for use therein
    • B41M5/26Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
    • B41M5/382Contact thermal transfer or sublimation processes
    • B41M5/385Contact thermal transfer or sublimation processes characterised by the transferable dyes or pigments
    • B41M5/388Azo dyes

Landscapes

  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Thermal Transfer Or Thermal Recording In General (AREA)
  • Coloring (AREA)

Abstract

PURPOSE:To obtain a recording of good color density, by using a specific thermal transfer recording cyanine coloring matter, having a preferable hue in terms of color reproducibility, a large molecular absorptivity coefficient, and stabilities to light, moisture, and chemicals, for an ink layer formed on a base film. CONSTITUTION:The coloring matter is shown by a formula 1. (In the formula, X represents hydrogen, alkyl, alkoxy, alkylcarbonyl-amino, or halogen, Y represents hydrogen, alkyl, alkoxy, or halogen, and R<1> and R<2> hydrogen, substituted or non-substituted alkyl or allyl, or aryl.) The ink prepared by a method wherein the coloring matter is dissolved or dispersed in a medium together with a binder is coated and dried on a base film to produce a transfer sheet. This coloring matter has suitabilities for a full color recording with good color reproducibility and a compounding ingredient for black coloring matter, a good subliming properties, and a large molecular absorptivity coefficient, which enables a recording to the performed at high speed without loading a thermal head to a great extent and to have high color density and sperior shelf stability.

Description

【発明の詳細な説明】 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に関する
DETAILED DESCRIPTION OF THE INVENTION Field of the Invention The present invention relates to dyes used in sublimation type thermal transfer recording.

従来の技術 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を、感熱ヘッド、赤外線など
の加熱手段により加熱して、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を
、加熱手段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、昇華方式は加熱時
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。
Conventional technology The thermal transfer method involves heating a transfer sheet with a heat-melting ink layer formed on a base film using a heating means such as a thermal head or infrared rays to melt the ink and transfer it onto a recording medium. There are two types of methods: the melt method, which performs transfer recording, and the sublimation method, which uses a heating means to heat a transfer sheet on which an ink layer containing a sublimable dye is formed on a base film to sublimate the dye, and transfer and record it onto a recording medium. However, the sublimation method can control the amount of sublimation transfer of the dye by changing the energy applied during heating, which facilitates gradation recording and is considered particularly advantageous for full-color recording.

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。
When applying a dye to this recording method, the dye must meet the following conditions.

■ 感熱記録ヘッドなどの通常用いられる加熱手段の作
動条件で容易に昇華すること。
■ Easily sublimes under the operating conditions of commonly used heating means such as thermal recording heads.

■ 昇華前に熱分解しないこと。■Do not thermally decompose before sublimation.

■ 色再現上、好ましい色相を有すること。■ It must have a favorable hue in terms of color reproduction.

■ 分子吸光係数が大きいこと。■ Large molecular extinction coefficient.

■ 光、湿気、薬品などに対して安定なこと。■ Stable against light, moisture, chemicals, etc.

■ 合成が容易なこと。■ Easy to synthesize.

■ インク化適性が優れていること。■ Excellent suitability for ink production.

発明が解決しようとする問題点 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。
Problems to be Solved by the Invention The object of the present invention is to provide a cyan dye that satisfies all of the above conditions.

問題点を解決するための手段 すなわち、本発明は、下記一般式(1)(式中、xii
水素原子、アルキル基、アルコキシ基、アルキルカルボ
ニルアミノ基又は)・ロゲン原子を表わし、Yは水素原
子、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、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す。)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。
Means for solving the problems, that is, the present invention solves the following general formula (1) (where xii
Represents a hydrogen atom, an alkyl group, an alkoxy group, an alkylcarbonylamino group, or a halogen atom; Y represents a hydrogen atom, an alkyl group, an alkoxy group, or a halogen atom; R1 and R2 are a hydrogen atom, a substituted or unsubstituted alkyl group , represents an allyl group or an aryl group. ) The gist thereof is a dye for thermal transfer recording shown in the following.

これら本発明の色素の製造方法としては、たとえば、下
記構造式(II) で示されるコーアミノーj−二トロチアゾールを常法に
よシ、ジアゾ化し、下記一般式(fir)(式中、X、
 Y%H1及びR2は前記定義に同じ。)で示されるア
ニリン類とカップリングすることる置換アルキル基の置
換基としては、アルコキシ基、ハロゲン原子、シアノ基
、ヒドロキシ基、アルキルカルボニルオキシ基、アルコ
キシカルボニルオキ7基等が挙げられる。
As a method for producing these dyes of the present invention, for example, co-amino-j-nitrothiazole represented by the following structural formula (II) is diazotized by a conventional method, and the following general formula (fir) (wherein X,
Y%H1 and R2 are the same as defined above. Examples of the substituent of the substituted alkyl group coupled with the aniline represented by ) include an alkoxy group, a halogen atom, a cyano group, a hydroxy group, an alkylcarbonyloxy group, an alkoxycarbonyloxy group, and the like.

特に好ましいものとしては、前記一般式(1)において
R1及びR2がCI〜Csのアルキル基、03〜Os 
(7)アルコキシアルキル基、β−クロロエチル基、β
−シアノエチル基、β−ヒドロキシエチル基、ベンジル
基、7エネチル基またはアセチルオキシエチル基であり
、Xが水素原子、メチル基、塩素原子、アセチルアミノ
基またはプロピオニルアミノ基であ5、Yが水素原子で
ある色素が挙げられる。
Particularly preferably, in the general formula (1), R1 and R2 are CI to Cs alkyl groups, 03 to Os
(7) Alkoxyalkyl group, β-chloroethyl group, β
- A cyanoethyl group, a β-hydroxyethyl group, a benzyl group, a 7enethyl group, or an acetyloxyethyl group, where X is a hydrogen atom, a methyl group, a chlorine atom, an acetylamino group, or a propionylamino group, and Y is a hydrogen atom Examples include dyes that are .

本発明の色素を昇華型感熱転写記録方式に適用する場合
、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
ースフィルム上に塗布、乾燥し転写シートを作製する必
要がある。
When applying the dye of the present invention to a sublimation type thermal transfer recording system, an ink is prepared by dissolving the dye or dispersing it in the form of fine particles in a medium together with a binder, and the ink is applied onto a base film and dried. It is necessary to create a 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、ポリスチレン、ポリカーボネート
、ポリスルホン、ホリエーテルスルホン、エチルセルロ
ース、酢酸セルロース、ボリアリレートなどの有機溶剤
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。
Binders for ink preparation include water-soluble resins such as cellulose, acrylic acid, and starch, acrylic resin, methacrylic resin, polystyrene, polycarbonate, polysulfone, polyether sulfone, ethyl cellulose, cellulose acetate, polyarylate, etc. Examples include resins that are soluble in organic solvents. 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.

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フ類、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
In addition to water, media for preparing ink 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, ethers such as tetrahydrofuran and dioxane, N, N-dimethylformamide, N-
Organic solvents such as methylpyrrolidone may be mentioned.

転写シート作製のためのインクを塗布するべ−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ックのフィルムが適しているが、
それらの厚さとしては3〜jO717nの範囲を挙げる
ことができる。
Suitable base films for applying ink for producing transfer sheets include thin paper such as capacitor paper and glassine paper, and films made of plastics with good heat resistance such as polyester, polyamide, and polyimide.
Their thickness can range from 3 to jO717n.

インクをベースフィルムに塗布する方法としては、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0.7〜jμmの
範囲となるよう塗布すれば良い(原崎勇次著、tDt書
店/92り年発行「コーティング方式」)。
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 0.7~ It is sufficient to apply the coating so that the coating is within the range of Jμm (Yuji Harasaki, “Coating Method”, published by tDt Shoten in 1992).

発明の効果 本発明の前記(1)で示されるアゾ系りアン色素は、適
当なイエロー色およびマゼンタ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・緑を得るのに適し
ており、更に、ブラック色素の配合成分としての適性も
有しており、又、昇華し易く、分子吸光係数が大きいた
め感熱ヘッドなど加熱手段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次め、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
。したがって、それらの転写シートを用いることにより
均−性及び色#度の良好な記録を得ることができる。
Effects of the Invention The azo riazo dye shown in the above (1) of the present invention is suitable for obtaining full color green with good color reproducibility by combining with appropriate yellow and magenta colors. Furthermore, it is suitable as a blending component for black dyes, and because it sublimes easily and has a large molecular extinction coefficient, it can record at high speed and with high color density without placing a large burden on heating means such as thermal heads. Obtainable. Furthermore, it is stable against heat, light, moisture, chemicals, etc., and 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.

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々い。
EXAMPLES The present invention will be explained in detail with reference to Examples below, but these Examples do not limit the present invention.

実施例/ (PL)  インクの調製 上記色素           /θを酢酸セルロース
(ダイセル    iot化学社製、L−3o) 上記組成の混合物をペイントコンディショナーで70分
間処理し、インクの調製を行なった。色素及び樹脂は完
全に溶解し、均一な溶液のインキを得ることができた。
Example/(PL) Preparation of ink The above pigment /θ was cellulose acetate (manufactured by Daicel IoT Chemical Co., Ltd., L-3o) A mixture having the above composition was treated with a paint conditioner for 70 minutes to prepare an ink. The pigment and resin were completely dissolved, and an ink with a uniform solution could be obtained.

(′b)転写シートの作製 上記のインクをバーコーター(RK Pri、ntCo
at工nstruments社製A/)を用いてポリイ
ミドフィルム(/jμm厚)上に塗布した後、乾燥して
転写シートを得た。
('b) Preparation of transfer sheet The above ink was coated with a bar coater (RK Pri, ntCo
A transfer sheet was obtained by coating the polyimide film (thickness: /jμm) using A/) manufactured by AT Instruments, and then drying it.

(Q)  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2、鮮明なシアン色で7.
30の均一な色濃度の記録を得ることができた。
(Q) Transfer Recording The ink-coated surface of the above transfer sheet was placed on the recording medium and recorded using a thermal head under the following conditions.
It was possible to obtain 30 records of uniform color density.

記録条件 主走査、副走査の線密度:ダドット/鱈記録電力  :
Q、≦W/ドツト ヘッドの加熱時間   : / Omeecなお、被記
録体は、飽和ポリエステル3弘重i%の水分散液(東洋
紡績株式会社製造、パイロナールMD−/コ00、商品
名)10tと7リカ(日本シリカニ業株式会社梨造、N
1psil  ]!i 、2コθA、商品名)/2を混
合し調製した液を合成紙(/10μm厚)にパーコータ
ー(RK Pr1nt Coat工nstrument
s 社製造、A−?)を用いて塗布後、乾燥して製造し
た。
Recording conditions Main scanning and sub-scanning linear density: Dadot/Cod Recording power:
Q, ≦W/Heating time of dot head: / Omeec Note that the recording medium was an aqueous dispersion of saturated polyester 3% by weight (manufactured by Toyobo Co., Ltd., Pyronal MD-/Co00, trade name) 10t and 7% by weight. (Nippon Sirikani Co., Ltd. Rizo, N
1 psi]! A liquid prepared by mixing 1, 2 θA, trade name)/2 was applied to synthetic paper (/10 μm thick) using a percoater (RK Pr1nt Coat instrument).
Manufactured by S company, A-? ) was applied and dried.

色濃度は、米国マクベス社製造、テンシトメーターRD
−!/ダ型(フィルター:ラツテンA2りを用いて測定
した。
Color density was measured using Tensitometer RD manufactured by Macbeth, USA.
-! /D type (filter: Measured using Ratten A2).

得られた記録の耐光性試験をカーボンアークフェードメ
ーター(スガ試験機株式会社製造)を用いて実施(ブラ
ックパネル温度≦3±−℃)したが、qo待時間照射後
はとんど変退色しなかった。また、転写シートおよび記
録は熱及び湿気に対して安定であり、暗所保存性にすぐ
れていた。
A light resistance test of the obtained record was carried out using a carbon arc fade meter (manufactured by Suga Test Instruments Co., Ltd.) (black panel temperature ≤3±-℃), but after qo waiting period irradiation, the color almost changed and faded. There wasn't. Furthermore, the transfer sheet and recording were stable against heat and moisture, and had excellent storage stability in the dark.

実施例λ 実施例/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/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
度の鮮明な記録を得ることができ穴。
Example λ Ink was prepared, a transfer sheet was prepared, and transfer recording was carried out in the same manner as in Example using the dyes shown in Table 1 instead of the dyes used in Example. Holes that allow you to get a clear record of color density showing.

Claims (1)

【特許請求の範囲】[Claims] (1)一般式〔 I 〕 ▲数式、化学式、表等があります▼〔 I 〕 (式中、Xは水素原子、アルキル基、アルコキシ基、ア
ルキ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、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、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
表わす。) で示される感熱転写記録用色素。
(1) General formula [I] ▲Mathematical formulas, chemical formulas, tables, etc.▼[I] (In the formula, X represents a hydrogen atom, an alkyl group, an alkoxy group, an alkylcarbonylamino group, or a halogen atom,
Y represents a hydrogen atom, an alkyl group, an alkoxy group, or a halogen atom, and R^1 and R^2 represent a hydrogen atom, a substituted or unsubstituted alkyl group, an allyl group, or an aryl group. ) A dye for thermal transfer recording.
JP60173877A 1985-08-07 1985-08-07 Dyestuff for thermal transfer recording Pending JPS6233688A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP60173877A JPS6233688A (en) 1985-08-07 1985-08-07 Dyestuff for thermal transfer recording

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP60173877A JPS6233688A (en) 1985-08-07 1985-08-07 Dyestuff for thermal transfer recording

Publications (1)

Publication Number Publication Date
JPS6233688A true JPS6233688A (en) 1987-02-13

Family

ID=15968780

Family Applications (1)

Application Number Title Priority Date Filing Date
JP60173877A Pending JPS6233688A (en) 1985-08-07 1985-08-07 Dyestuff for thermal transfer recording

Country Status (1)

Country Link
JP (1) JPS6233688A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0284393A (en) * 1988-09-21 1990-03-26 Hitachi Ltd Thermal transfer sheet, production thereof and thermal transfer method
CN104861690A (en) * 2014-02-21 2015-08-26 江苏道博化工有限公司 Method used for preparing disperse blue 360
CN105622543A (en) * 2016-02-16 2016-06-01 北京泛博清洁技术研究院有限公司 Acidic dischargeable blue dye compound for furs and application method of acidic dischargeable blue dye compound for furs
CN106243775A (en) * 2016-07-20 2016-12-21 浙江山峪染料化工有限公司 Warm type disperse dye composition in one
KR20200112124A (en) * 2019-03-21 2020-10-05 충남대학교산학협력단 Disperse dyes for supercritical fluid dyeing and Supercritical fluid dyeing of nylon fabrics using the same

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0284393A (en) * 1988-09-21 1990-03-26 Hitachi Ltd Thermal transfer sheet, production thereof and thermal transfer method
CN104861690A (en) * 2014-02-21 2015-08-26 江苏道博化工有限公司 Method used for preparing disperse blue 360
WO2015123992A1 (en) * 2014-02-21 2015-08-27 江苏道博化工有限公司 Method for preparing disperse blue 360
CN104861690B (en) * 2014-02-21 2017-02-08 江苏道博化工有限公司 Method used for preparing disperse blue 360
CN105622543A (en) * 2016-02-16 2016-06-01 北京泛博清洁技术研究院有限公司 Acidic dischargeable blue dye compound for furs and application method of acidic dischargeable blue dye compound for furs
CN106243775A (en) * 2016-07-20 2016-12-21 浙江山峪染料化工有限公司 Warm type disperse dye composition in one
KR20200112124A (en) * 2019-03-21 2020-10-05 충남대학교산학협력단 Disperse dyes for supercritical fluid dyeing and Supercritical fluid dyeing of nylon fabrics using the same

Similar Documents

Publication Publication Date Title
JPS60239291A (en) Coloring matter for thermal recording
JPH0545436B2 (en)
JPS6131292A (en) Coloring matter for thermal transfer recording
JPS61227092A (en) Azo dyestuff for thermal transfer recording
JPS6233688A (en) Dyestuff for thermal transfer recording
JPS6122993A (en) Coloring matter for thermal transfer recording
JPS60239292A (en) Coloring matter for thermal transfer recording
JPS6339380A (en) Thermal transfer sheet
JP2623241B2 (en) Dye for thermal transfer recording and thermal transfer sheet
JPS61148096A (en) Transfer sheet
JPS61148269A (en) Indoaniline compound and dyestuff for heat-sensitive transfer recording
JP3635933B2 (en) Pyridoneazo dye for thermal transfer, thermal transfer sheet and thermal transfer ink using the same
JPH0515198B2 (en)
JPS6119396A (en) Coloring matter for thermal transfer recording
JPS61244595A (en) Pyridone azo coloring matter for thermal transfer recording
JPS63189289A (en) Thermal transfer sheet
JP3058520B2 (en) Thermal transfer sheet
JPH05236B2 (en)
JPH051155B2 (en)
JP3222236B2 (en) Magenta dye for thermal sublimation transfer recording, ink composition containing the dye, and transfer sheet
JPS61227091A (en) Coloring matter of dicyanoimidazole series for thermal transfer recording
JPS6232147A (en) Dye for thermal transfer recording
JP2944671B2 (en) Dye for sublimation transfer recording
JP2909962B2 (en) Azo dye for thermal transfer recording
JP3370713B2 (en) Cyan dye for thermal sublimation transfer recording, ink composition containing the dye, and transfer sheet