JP6594513B2 - 色素化合物及び感熱転写記録用シート - Google Patents
色素化合物及び感熱転写記録用シート Download PDFInfo
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Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B55/00—Azomethine dyes
- C09B55/009—Azomethine dyes, the C-atom of the group -C=N- being part of a ring (Image)
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/10—Amino derivatives of triarylmethanes
- C09B11/12—Amino derivatives of triarylmethanes without any OH group bound to an aryl nucleus
-
- 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
- B41M5/382—Contact thermal transfer or sublimation processes
- B41M5/385—Contact thermal transfer or sublimation processes characterised by the transferable dyes or pigments
-
- 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
- B41M5/382—Contact thermal transfer or sublimation processes
- B41M5/385—Contact thermal transfer or sublimation processes characterised by the transferable dyes or pigments
- B41M5/3858—Mixtures of dyes, at least one being a dye classifiable in one of groups B41M5/385 - B41M5/39
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/201—Dyes with no other substituents than the amino groups
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/10—Amino derivatives of triarylmethanes
- C09B11/12—Amino derivatives of triarylmethanes without any OH group bound to an aryl nucleus
- C09B11/16—Preparation from diarylketones or diarylcarbinols, e.g. benzhydrol
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/10—Amino derivatives of triarylmethanes
- C09B11/12—Amino derivatives of triarylmethanes without any OH group bound to an aryl nucleus
- C09B11/20—Preparation from other triarylmethane derivatives, e.g. by substitution, by replacement of substituents
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/008—Triarylamine dyes containing no other chromophores
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M2205/00—Printing methods or features related to printing methods; Location or type of the layers
- B41M2205/30—Thermal donors, e.g. thermal ribbons
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Thermal Transfer Or Thermal Recording In General (AREA)
Description
R1及びR2は、各々独立して、アルキル基を示し、
R3及びR4は、各々独立して、水素原子、アルキル基、アリール基、またはアリールアルキル基を表し、
R5及びR6は、各々独立して、水素原子、または炭素数1〜4のアルキル基を表し、
R7及びR8は、各々独立して、炭素数1〜4のアルキル基を表し、
R9は、ハロゲン原子、ニトロ基、スルホ基、スルホン酸アルキルエステル基、スルホンアミド基、スルホン酸塩基、またはパーフルオロアルキル基を表し、
R10は、水素原子、ハロゲン原子、ニトロ基、スルホ基、スルホン酸アルキルエステル基、スルホンアミド基、スルホン酸塩基、またはパーフルオロアルキル基を表し、
X−は、アニオンを表す。]
R1〜R8は、式(1−1)におけるR1〜R8と同義である。
R10’は、水素原子、ハロゲン原子、ニトロ基、スルホ基、スルホン酸アルキルエステル基、スルホンアミド基、スルホン酸塩基、またはパーフルオロアルキル基を表す。]
また、本発明は、基材と、該基材上に色材層とを有する感熱転写記録用シートであって、
該色材層は、少なくともイエロー染料を含有するイエロー染料層、マゼンタ染料を含有するマゼンタ染料層、及びシアン染料を含有するシアン染料層を有し、
該シアン染料が、上記式(1−1)または式(1−2)で示される構造を有する色素化合物であることを特徴とする感熱転写記録用シートに関する。
下記式(1−1)又は(1−2)で示される化合物が、高彩度、高耐光性を有し、分散性に優れることを見出し本発明に至った。
R1及びR2は、各々独立して、置換基を有するアルキル基、または無置換のアルキル基を示し、
R3及びR4は、各々独立して、水素原子、置換基を有するアルキル基、無置換のアルキル基、置換基を有するアリール基、または無置換のアリール基を表し、
R5及びR6は、各々独立して、水素原子、または無置換の炭素数1〜4のアルキル基を表し、
R7及びR8は、各々独立して、無置換の炭素数1〜4のアルキル基を表し、
R9は、ハロゲン原子、ニトロ基、スルホ基、スルホン酸エステル基、スルホンアミド基、スルホン酸塩基、ベンゼンスルホニル基、トリフルオロメチルスルホニル基またはパーフルオロアルキル基を表し、
R10は、水素原子、ハロゲン原子、ニトロ基、スルホ基、スルホン酸エステル基、スルホンアミド基、スルホン酸塩基、ベンゼンスルホニル基、トリフルオロメチルスルホニル基、またはパーフルオロアルキル基を表し、
X−は、アニオンを表す。]
R1〜R8は、式(1−1)におけるR1〜R8と同義である。
R9’は、スルホナト基を表し、
R10’は、水素原子、ハロゲン原子、ニトロ基、スルホ基、スルホン酸エステル基、スルホンアミド基、スルホン酸塩基、ベンゼンスルホニル基、トリフルオロメチルスルホニル基、またはパーフルオロアルキル基を表す。]
まず、縮合工程について説明する。縮合工程は、必要に応じて、媒体、縮合剤、酸化剤などの存在下で行うことができる。
次に、酸化工程について説明する。酸化工程は、必要に応じて、媒体、酸化剤などの存在下で行うことができる。
式(2)中、R11〜R15におけるアルキル基としては、上記式(1−1)のR1、R2、R3及びR4におけるアルキル基として例示したものと同様の基が挙げられる。特に、メチル基、エチル基などの炭素数1〜2個のアルキル基を用いる場合、高彩度、高分散、高耐光性に優れるため好ましい。
本発明の感熱転写記録用シートは、基材と、基材上に色材層とを有する。色材層は、少なくとも、イエロー染料を含有するイエロー染料層と、マゼンタ染料を含有するマゼンタ染料層と、シアン染料を含有するシアン染料層を含む。
本発明による感熱転写記録用シートを構成する基材は、後述する色材層を支持するものであり、公知の基材を用いることができる。ある程度の耐熱性と強度を有するものであれば特に限定されるわけではないが、例えば、以下のものが挙げられる。ポリエチレンテレフタレートフィルム、ポリエチレンナフタレートフィルム、ポリカーボネートフィルム、ポリイミドフィルム、ポリアミドフィルム、アラミドフィルム、ポリスチレンフィルム、1,4−ポリシクロヘキシレンジメチレンテレフタレートフィルム、ポリサルホンフィルム、ポリプロピレンフィルム、ポリフェニレンサルフィドフィルム、ポリビニルアルコールフィルム、セロハン、セルロース誘導体、ポリエチレンフィルム、ポリ塩化ビニルフィルム、ナイロンフィルム、コンデンサー紙、パラフィン紙。
感熱転写記録用シートは、基材上に、色材層を有する。色材層は、少なくとも、イエロー染料層とマゼンタ染料層とシアン染料層とを有する。感熱転写記録用シートには、染料層として、従来公知のブラック染料層を追加しても良い。
また感熱転写記録用シートにおいては、サーマルヘッド加熱時(印画時)に十分な滑性を持たせるために、界面活性剤を含有させてもよい。添加することができる界面活性剤としては、カチオン界面活性剤、アニオン界面活性剤、ノニオン界面活性剤が挙げられる。
感熱転写記録用シートを加熱する加熱手段としては、特に限定されるものではないが、サーマルヘッドを用いた常法のみならず、赤外線又はレーザー光も利用することができる。また、ベースフィルムそのものに電気を流すことによって加熱することもできる。この場合には、発熱する通電発熱フィルムを用いて、通電型染料転写シートとすればよい。
(製造例1:化合物(A3)の製造)
N,N−ジブチル−2,6−ジメチルアニリン(2.32g)の氷酢酸(20mL)溶液に、2−スルホベンズアルデヒドナトリウム(0.98g)を加え、100℃で12時間加熱した。反応終了後、室温まで冷却し、水(50mL)で希釈し、クロロホルム(50mL)で抽出した。減圧濃縮後、酢酸エチル(20mL)に溶解し、クロラニル(2.33g)を添加し、80℃、4時間加熱した。反応終了後、ろ過し、得られたろ液を水で3回洗浄した。カラムクロマトグラフィーにより精製し、(A3)(1.96g)を得た。
〔1〕1H−NMR(600MHz、DMSO−d6、室温25℃)の結果:
δ(ppm)=7.78(2H、m)、7.62(1H、dd)、7.45(1H、dd)、6.87(12H、s)、3.78(8H、m)、2.12(12H、s)、1.49(8H、m)、1.31(8H、m)、0.90(12H、m)
〔2〕MALDI−TOF/MS分析結果:
m/z=633.20(M+H)+
製造例1と同様の方法で表1に示す化合物を製造し、同定した。
比較化合物としては、以下の化合物を使用した。
メチルエチルケトン45部/トルエン45部の混合溶液にポリビニルブチラール樹脂(デンカ3000−K;電気化学工業(株)製)5部を少しずつ添加して溶解させた。ここに、化合物(A3)5部を添加して溶解させることで、シアン染料層作製用のシアンインク(C1)を得た。
シアンインク調製例1において、化合物(A3)を表1に示すシアン染料(本発明の化合物及び比較化合物)に変更した以外は、シアンインク調製例1と同様な操作でシアンインク(C2)〜(C4)を得た。
基材として、厚さ4.5μmのポリエチレンテレフタレートフィルム(ルミラー(登録商標);東レ(株)製)を用いる。該基材上に、乾燥後の厚みが1μmになるように上記シアンインク(C1)を塗布し、乾燥することによって、シアン染料層を形成した。
実施例1において、使用するシアンインクを表2に記載のように変更する以外は実施例1と同様にして、シアン染料層を有する感熱転写記録用シートを作製した。
作製した各画像サンプルについて、分光濃度系(蛍光分光濃度計FD−7、コニカミノルタ社製)を用いて、L*a*b*表色系における色度(L*、a*、b*)を測定し、彩度(C*)を下式によって算出した。
A:C*が45.0以上
B:C*が35.0以上45.0未満
C:C*が35.0未満
上記画像サンプルをキセノン試験装置(アトラス ウエザオメータCi4000、株式会社東洋精機製作所製)に投入し、(照度:340nmで0.28W/m2、ブラックパネル温度:40℃、相対湿度:50%)の条件下、20時間曝露した。初期の光学濃度をOD0とし、20時間曝露後のO.D.をOD20としたとき、O.D.残存率を以下のように定義した。
評価基準は以下のとおりである。
A:60<O.D.残存率(%)
B:50<O.D.残存率(%)≦60
C:O.D.残存率(%)≦50
位相差顕微鏡(商品名:BX53、OLYMPUS(株)製)を用いて20倍に拡大して各画像サンプルの観察を行い、化合物の分散性の評価を行った。
A:化合物の凝集物がほとんど観察されない
B:化合物の凝集物が少し確認される
C:化合物の凝集物がかなり確認される
Claims (7)
- 下記式(1−1)又は(1−2)で示される構造を有する色素化合物。
[式(1−1)中、
R1及びR2は、各々独立して、アルキル基を示し、
R3及びR4は、各々独立して、水素原子、アルキル基、アリール基、またはアリールアルキル基を表し、
R5及びR6は、各々独立して、水素原子、または炭素数1〜4のアルキル基を表し、
R7及びR8は、各々独立して、炭素数1〜4のアルキル基を表し、
R9は、ハロゲン原子、ニトロ基、スルホ基、スルホン酸アルキルエステル基、スルホンアミド基、スルホン酸塩基、またはパーフルオロアルキル基を表し、
R10は、水素原子、ハロゲン原子、ニトロ基、スルホ基、スルホン酸アルキルエステル基、スルホンアミド基、スルホン酸塩基、またはパーフルオロアルキル基を表し、
X−は、アニオンを表す。]
[式(1−2)中、
R1〜R8は、式(1−1)におけるR1〜R8と同義である。
R9’は、−SO 3 − を表し、
R10’は、水素原子、ハロゲン原子、ニトロ基、スルホ基、スルホン酸アルキルエステル基、スルホンアミド基、スルホン酸塩基、またはパーフルオロアルキル基を表す。] - 式(1−1)中、R 3 及びR 4 は、各々独立して、水素原子、アルキル基、アリール基、またはベンジル基を表し、R 9 は、ハロゲン原子、ニトロ基、またはパーフルオロアルキル基を表し、R 10 は、水素原子、ハロゲン原子、ニトロ基、またはパーフルオロアルキル基を表し、
式(1−2)中、R 3 及びR 4 は、各々独立して、水素原子、アルキル基、アリール基、またはベンジル基を表し、R 9 は、ハロゲン原子、ニトロ基、またはパーフルオロアルキル基を表し、R 10 は、水素原子、ハロゲン原子、ニトロ基、またはパーフルオロアルキル基を表す、
請求項1に記載の色素化合物。 - 前記式(1−1)および式(1−2)において、R1とR2とが同一のアルキル基であるである請求項1又は2に記載の色素化合物。
- 基材と、該基材上に色材層とを有する感熱転写記録用シートであって、
該色材層は、少なくともイエロー染料を含有するイエロー染料層、マゼンタ染料を含有するマゼンタ染料層、及びシアン染料を含有するシアン染料層を有し、
該シアン染料が、請求項1乃至5のいずれか1項に記載された色素化合物を含むことを特徴とする感熱転写記録用シート。
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