JPH03295687A - Dyestuff for thermal transfer recording - Google Patents
Dyestuff for thermal transfer recordingInfo
- Publication number
- JPH03295687A JPH03295687A JP2097704A JP9770490A JPH03295687A JP H03295687 A JPH03295687 A JP H03295687A JP 2097704 A JP2097704 A JP 2097704A JP 9770490 A JP9770490 A JP 9770490A JP H03295687 A JPH03295687 A JP H03295687A
- Authority
- JP
- Japan
- Prior art keywords
- group
- atom
- member ring
- hydrogen atom
- membered ring
- 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
Links
- 239000000975 dye Substances 0.000 title abstract description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 13
- 125000004429 atom Chemical group 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 8
- 125000003118 aryl group Chemical group 0.000 claims abstract description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 5
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 4
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 3
- 125000005647 linker group Chemical group 0.000 claims description 3
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 4
- 239000003086 colorant Substances 0.000 abstract description 2
- 230000018109 developmental process Effects 0.000 abstract 1
- 230000008929 regeneration Effects 0.000 abstract 1
- 238000011069 regeneration method Methods 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- -1 aldehyde compound Chemical class 0.000 description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000000859 sublimation Methods 0.000 description 4
- 230000008022 sublimation Effects 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920001225 polyester resin Polymers 0.000 description 3
- 239000004645 polyester resin Substances 0.000 description 3
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000004450 alkenylene group Chemical group 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000004966 cyanoalkyl group Chemical group 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 239000000986 disperse dye Substances 0.000 description 2
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 229920000298 Cellophane Polymers 0.000 description 1
- 229920000084 Gum arabic Polymers 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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical group ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- INLLPKCGLOXCIV-UHFFFAOYSA-N bromoethene Chemical group BrC=C INLLPKCGLOXCIV-UHFFFAOYSA-N 0.000 description 1
- 125000005569 butenylene group Chemical group 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000012461 cellulose resin Substances 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 125000005462 imide group Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 150000002832 nitroso derivatives Chemical class 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- NARVIWMVBMUEOG-UHFFFAOYSA-N prop-1-en-2-ol Chemical group CC(O)=C NARVIWMVBMUEOG-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006410 propenylene group Chemical group 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 125000005156 substituted alkylene group Chemical group 0.000 description 1
- 125000005649 substituted arylene group Chemical group 0.000 description 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000013077 target material Substances 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000001043 yellow dye Substances 0.000 description 1
- 239000001052 yellow pigment Substances 0.000 description 1
Landscapes
- Thermal Transfer Or Thermal Recording In General (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は悠然転写記録用イエロー色素に関し、更に詳し
くは、昇華型感熱転写記録方法において、有用な転写性
、着色性、諸堅牢性に優れた鮮明なイエロー色の色素を
提供することを目的とｒざ。Detailed Description of the Invention (Field of Industrial Application) The present invention relates to a yellow dye for leisurely transfer recording, and more specifically, it has excellent transferability, colorability, and various fastness properties that are useful in sublimation type heat-sensitive transfer recording methods. The purpose is to provide a vivid yellow pigment.
（従来の技術）
現在、テレビ、ビデオ、スチルビデオカメラなどの一過
性の画像からハードコピーを得る方法の一つに昇華型感
熱転写記録方式がある。(Prior Art) Currently, one of the methods for obtaining hard copies from ephemeral images from televisions, videos, still video cameras, etc. is the sublimation type thermal transfer recording method.
この方法は熱により色素を昇華させて、被記録体に像を
形成させるものであり熱源として発熱素子又は半導体レ
ーザが用いられる。この熱源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、
階調性の良い画像が得られるので、この方式は特にビク
トリアルカラー記録には有利な方法と考えられる。In this method, a dye is sublimated by heat to form an image on a recording medium, and a heating element or a semiconductor laser is used as a heat source. By changing the energy given to this heat source, the amount of dye sublimation transfer can be controlled.
Since an image with good gradation can be obtained, this method is considered to be particularly advantageous for Victorian color recording.
（発明が解決しようとする問題点）
減色法によりフルカラー画像を得る場合、色相表現の基
本となる三原色は、イエロー、マゼンタ、シアンである
。このうちイエローはブルーの補色であり、澄んだ黄色
で、その極大吸収波長が４２０〜４８０ ｎｍであるこ
とが要求される。現在昇華型感熱転写記録用として用い
られているイエロー色の分散染料は、彩度が不足してお
り色再現性の優れたカラー画像は得られない。(Problems to be Solved by the Invention) When obtaining a full-color image by the subtractive color method, the three primary colors that are the basis of hue expression are yellow, magenta, and cyan. Among these, yellow is a complementary color to blue, and is required to be clear yellow and have a maximum absorption wavelength of 420 to 480 nm. Yellow disperse dyes currently used for sublimation type thermal transfer recording lack chroma and cannot provide color images with excellent color reproducibility.
又最近の記録方法の進歩に伴い、低エネルギで十分に濃
度のある鮮明な画像を与えることのできる高速記録用材
料が望まれているが、この点でも現在用いられている分
散染料は十分満足のいく性能を有していない。In addition, with recent advances in recording methods, there is a need for high-speed recording materials that can provide clear images with sufficient density with low energy consumption, but the disperse dyes currently used are not fully satisfactory in this respect. It does not have the same performance.
本発明は、このような状況に鑑み、従来技術の問題点を
解決すべく、鋭意研究の結果、ビスジシアノスチレン系
色素が極めて転写性に優れ、又鮮明なイエロー色を呈し
、マゼンタ色素、シアン色素と混合した際すぐれた色再
現性を示すことを見出し、本発明を完成することに至っ
た。In view of this situation, and in order to solve the problems of the prior art, the present invention was developed as a result of intensive research and found that the bisdicyanostyrene dye has extremely excellent transferability, exhibits a clear yellow color, and is superior to magenta and cyan dyes. It was discovered that it exhibits excellent color reproducibility when mixed with a pigment, leading to the completion of the present invention.
（問題点を解決するための手段）
即ち、本発明は一般式（１）
式中、Ｒ＋、及びＲ３は同−又は異なってもよく、水素
原子、置換又は非置換アルキル基、シクロアルキル基、
アラルキル基、アリール基であるか、あるいはＸと一緒
に５員環又は６員環を形成する原子又は原子団を表し、
Ｒｚ、及びＲ４は同−又は異なってもよく、水素原子、
置換又は非置換アルキル基、シクロアルキル基、アラル
キル基。(Means for Solving the Problems) That is, the present invention has the general formula (1), where R+ and R3 may be the same or different, a hydrogen atom, a substituted or unsubstituted alkyl group, a cycloalkyl group,
represents an aralkyl group, an aryl group, or an atom or atomic group that forms a 5-membered ring or 6-membered ring together with X,
Rz and R4 may be the same or different, and are hydrogen atoms,
Substituted or unsubstituted alkyl groups, cycloalkyl groups, aralkyl groups.
アリール基を表す。なお、Ｒ＋ とＲ２およびＲ３とＲ
４は酸素原子、窒素原子または硫黄原子を含有してもよ
い５員環又は６員環を形成しても良い。Represents an aryl group. In addition, R+ and R2 and R3 and R
4 may form a 5-membered ring or a 6-membered ring which may contain an oxygen atom, nitrogen atom or sulfur atom.
Ｒ１は同−又は異なってもよ（電子吸引基を表し、Ａは
２価の連結基を表す。Ｚはメチン基または窒素原子を表
し、Ｘは水素原子であるか、あるいはＲ６及びＲ１とそ
れぞれ一緒に５員環又は６員環を形成する原子又は原子
団を表す。R1 may be the same or different (represents an electron-withdrawing group, A represents a divalent linking group, Z represents a methine group or a nitrogen atom, X is a hydrogen atom, or R6 and R1, respectively) Represents atoms or atomic groups that together form a 5- or 6-membered ring.
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。The gist is the dye for thermal transfer recording shown in the following.
一般式（１）で示される色素は、公知の方法、例えば下
記反応式に従い一般式（２）で示されるアルデヒド化合
物あるいは一般式（３）で示され石ニトロソ化合物と、
−数式（４）で示される活性メチレン化合物を酸、塩基
あるいは酸塩基触媒の存在下、脱水縮合することにより
容易に製造することができる。The dye represented by the general formula (1) can be prepared by a known method, for example, with an aldehyde compound represented by the general formula (2) or a stone nitroso compound represented by the general formula (3), according to the following reaction formula.
- The active methylene compound represented by formula (4) can be easily produced by dehydration condensation in the presence of an acid, a base, or an acid-base catalyst.
１）
（３）
（４）
（２）
（４）
（１−２）
（式中、Ｒ１，ＲＺ、Ｒ３，Ｒ４，Ｒ５，ＸおよびＡは
いずれも前記した基と同一である）
前記−数式（１）で示されるＲ１及びＲ３としては同−
又は異なってもよく、水素原子；メチル基エチル基、プ
ロピル基、ブチル基等のアルキル基；メトキシエチル基
、エトキシエチル基等のアルコキシアルキル基；ヒドロ
キシエチル基、β−ヒドロキシプロピル基等のヒドロキ
シアルキル基；クロロエチル基等のハロゲノアルキル基
；シアノメチル基、シアノエチル基等のシアノアルキル
基；シクロヘキサン基等のシクロアルキル基；ベンジル
基、フェネチル基等のアラルキル基；フェニル基、トリ
ル基、ハロゲノフェニル基、アルコキシフェニル基等の
アリール基であるか、あるいはＸと一緒に５員環または
６員環を形成する原子が挙げられる。1) (3) (4) (2) (4) (1-2) (In the formula, R1, RZ, R3, R4, R5, X and A are all the same as the above-mentioned groups) - Formula R1 and R3 shown in (1) are the same as -
or may be different, hydrogen atom; alkyl group such as methyl group, ethyl group, propyl group, butyl group; alkoxyalkyl group such as methoxyethyl group, ethoxyethyl group; hydroxyalkyl group such as hydroxyethyl group, β-hydroxypropyl group Group; Halogenoalkyl group such as chloroethyl group; Cyanoalkyl group such as cyanomethyl group, cyanoethyl group; Cycloalkyl group such as cyclohexane group; Aralkyl group such as benzyl group, phenethyl group; Phenyl group, tolyl group, halogenophenyl group, alkoxy Examples include an aryl group such as a phenyl group, or an atom that forms a 5- or 6-membered ring together with X.
Ｒ２及びＲ１としては同−又は異なってもよく、水素原
子；メチル基、エチル基、プロピル基、ブチル基等のア
ルキル基；メトキシエチル基、エトキシエチル基等のア
ルコキシアルキル基；ヒドロキシエチル基、β−ヒドロ
キシプロピル基等のヒドロキシアルキル基；クロロエチ
ル基等のハロゲノアルキル基；シアノメチル基、シアノ
エチル基等のシアノアルキル基；シクロヘキサン基等の
シクロアルキル基；ベンジル基、フェネチル基等のアラ
ルキル基；フェニル基、トリル基、ハロゲノフェニル基
、アルコキシフェニル基等のアリール基が挙げられる。R2 and R1 may be the same or different; hydrogen atom; alkyl group such as methyl group, ethyl group, propyl group, butyl group; alkoxyalkyl group such as methoxyethyl group, ethoxyethyl group; hydroxyethyl group, β - Hydroxyalkyl groups such as hydroxypropyl groups; halogenoalkyl groups such as chloroethyl groups; cyanoalkyl groups such as cyanomethyl and cyanoethyl groups; cycloalkyl groups such as cyclohexane groups; aralkyl groups such as benzyl groups and phenethyl groups; phenyl groups, Examples include aryl groups such as tolyl group, halogenophenyl group, and alkoxyphenyl group.
なお、Ｒ，とＲ２およびＲ１とＲ４は酸素原子。Note that R, and R2 and R1 and R4 are oxygen atoms.
窒素原子または硫黄原子を含有してもよい５員環又は６
員環を形成しても良い。5-membered ring or 6-membered ring which may contain a nitrogen atom or a sulfur atom
A member ring may be formed.
Ｒ２としては同−又は異なってもよく、シアノ基；カル
ボキシル基；アセチル基、プロパノイル基ベンゾイル基
等のアシル基；メタンスルホニル基、エタンスルホニル
基等のアルキルスルホニル基；フェニルスルホニル基、
ｐ−クロロフェニルスルホニル基等のアリールスルホニ
ル基；メチルカルバモイル基、エチルカルバモイル基、
フェニルカルバモイル基等のカルバモイル基：メチルス
ルファモイル基、エチルスルファモイル基、フェニルス
ルファモイル基等のスルファモイル基；メトキシカルボ
ニル基、エトキシカルボニル基、プロポキシカルボニル
基等のアルコキシカルボニル基；フェノキシカルボニル
基、Ｐ−メチルフェノキシカルボニル基等のアリールオ
キンカルボニル基などの電子吸引性基が挙げられる。R2 may be the same or different; cyano group; carboxyl group; acyl group such as acetyl group, propanoyl group, benzoyl group; alkylsulfonyl group such as methanesulfonyl group, ethanesulfonyl group; phenylsulfonyl group,
Arylsulfonyl group such as p-chlorophenylsulfonyl group; methylcarbamoyl group, ethylcarbamoyl group,
Carbamoyl groups such as phenylcarbamoyl groups: sulfamoyl groups such as methylsulfamoyl group, ethylsulfamoyl group, phenylsulfamoyl group; alkoxycarbonyl groups such as methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group; phenoxycarbonyl group , and electron-withdrawing groups such as aryloquine carbonyl groups such as P-methylphenoxycarbonyl groups.
Ａは２価の連結基であり、酸素原子；メチレン基、エチ
レン基、プロピレン基、ブチレン基、イソプロピレン基
、ブロモエチレン基、２−ヒドロキシプロピレン基等の
非置換または置換アルキレン基；ビニレン基、プロペニ
レン基、ブテニレン基等のアルケニレン基；フェニレン
基、ヒドロキシフェニレン基、ナフチレン基等のＩＩＪ
ＪＩまたは置換アリ−リレン基；さらに以下のような官
能基（エーテル基、チオ−エーテル基、カルボニル基ア
ミノ基、アミド基、イミド基、ウレイド基、カルボニル
オキシ基、スルホニル基、スルホニルアミノ基、ビニル
基など）を含有するアルキレン基、アルケニレン基およ
びアリ−リレン基を表す。例えば次式のものが挙げられ
る。A is a divalent linking group; an oxygen atom; an unsubstituted or substituted alkylene group such as a methylene group, an ethylene group, a propylene group, a butylene group, an isopropylene group, a bromoethylene group, or a 2-hydroxypropylene group; a vinylene group; Alkenylene groups such as propenylene group and butenylene group; IIJ such as phenylene group, hydroxyphenylene group, naphthylene group, etc.
JI or substituted arylene group; and the following functional groups (ether group, thio-ether group, carbonyl group, amino group, amide group, imide group, ureido group, carbonyloxy group, sulfonyl group, sulfonylamino group, vinyl represents an alkylene group, an alkenylene group, and an arylene group containing a group (such as a group). For example, the following formula can be cited.
６
ＣＨｚ ０ＣＨｚ 、 ＣＨｚ ＣＨｚ
Ｓ ＣＨｚ ＣＨｚ 、 ＣＨｚ Ｎ ＨＣ
Ｈｚ （Ｒｈは水素原子またはアルキル基）、−Ｃ
Ｈ３ＣＮ、Ｃ０ＣＨ２ＣＨ，＋、 −ＣＨ２ＣＨ２０
ＣＯＣＨ２ＣＨ２−−ＣＨ２ＣＨ２Ｃ０ＮＨＣＯＣＨ２
ＣＨｚ −−ＣＨ２ＮＨＣＯＮＨＣＨ２−−ＣＨ２Ｃ
ＯＮＨＣＨ２−、−ＣＨ２Ｓｏ□ ＮＨＣＨ２−−ｃＨ
ｚＣＨｚＳＯ□ＣＨｚＣＨｚ 、 ＣＨｚＣＨ，
Ｃ＝ＣＣＨ２ＣＨ２−、−ｏ−ＣＨ２−−ＣＨ２−０−
Ｘは水素原子であるか、あるいはＲ，及びＲ２とそれぞ
れ一緒に５員環又は６員環を形成する原子又は原子団を
表す。6 Chz 0Chz, Chz Chz
S CHz CHz, CHz NHC
Hz (Rh is a hydrogen atom or an alkyl group), -C
H3CN, C0CH2CH, +, -CH2CH20
COCH2CH2--CH2CH2C0NHCOCH2
CHz --CH2NHCONHCH2 --CH2C
ONHCH2-, -CH2So□ NHCH2--cH
zCHzSO□CHzCHz, CHzCH,
C=CCH2CH2-, -o-CH2--CH2-0- X represents a hydrogen atom or an atom or atomic group forming a 5-membered ring or a 6-membered ring together with R and R2, respectively.
以下に本発明に用いられる一般式（１）で示される色素
の好ましい具体例を示す。Preferred specific examples of the dye represented by the general formula (1) used in the present invention are shown below.
本発明の色素を用いて感熱転写記録用インキを製造する
方法としては、色素を適当な結合剤と共に溶剤中でボー
ルミルなどを用いて溶解又は微粒化してインキとする方
法がある。結合剤としては、エポキシ樹脂、フェノール
樹脂、ウレタン樹脂、アクリル樹脂、シリコーン樹脂、
セルロース樹脂、ポリ塩化ビニル、ポリエチレン、ポリ
スチレン、ポリカーボネート、ポリエステル、ポリイミ
ド、ポリビニルブチラール、アラビアゴム、カゼインな
どが挙げられる。又溶剤としては、水、メタノール、エ
タノール、プロパノール、ブタノール等のアルコール類
、トルエン、キシレン、モノクロルベンゼン等の芳香族
炭化水素、アセトン、メチルエチルケトン、メチルイソ
ブチルケトン等のケトン類、ジクロルエタン、トリクロ
ルエチレン、パークロルエチレン等のハロゲン化水素類
、酢酸エチル、酢酸ブチル等のエステル類、メチルセロ
ソルブ、エチルセロソルブ等のセロソルブ類などが挙げ
られる。又転写方法としては、上記で得られたインキを
適当な基体上にバーコータを用いて塗布して転写シート
を作成し、該シートを被記録体と重ね、次いでシートの
背面から発熱素子等で加熱する方法があり、そのように
すればシート上の色素が、被記録体上に転写される。転
写基体としては、一般にコンデンサー紙、セロハン紙、
又はポリイミド樹脂、ポリエステル樹脂のような耐熱性
の良好なプラスチックフィルムが適している。A method for producing a thermal transfer recording ink using the dye of the present invention includes a method in which the dye is dissolved or atomized using a ball mill or the like in a solvent together with a suitable binder to form an ink. As a binder, epoxy resin, phenol resin, urethane resin, acrylic resin, silicone resin,
Examples include cellulose resin, polyvinyl chloride, polyethylene, polystyrene, polycarbonate, polyester, polyimide, polyvinyl butyral, gum arabic, and casein. Examples of solvents include water, alcohols such as methanol, ethanol, propanol, and butanol, aromatic hydrocarbons such as toluene, xylene, and monochlorobenzene, ketones such as acetone, methyl ethyl ketone, and methyl isobutyl ketone, dichloroethane, trichloroethylene, and perk. Examples include hydrogen halides such as chloroethylene, esters such as ethyl acetate and butyl acetate, and cellosolves such as methyl cellosolve and ethyl cellosolve. As a transfer method, the ink obtained above is applied onto a suitable substrate using a bar coater to create a transfer sheet, the sheet is placed on the recording medium, and then heated from the back side of the sheet with a heating element, etc. There is a method to do this, in which the dye on the sheet is transferred onto the recording medium. Transfer substrates generally include capacitor paper, cellophane paper,
Alternatively, a plastic film with good heat resistance such as polyimide resin or polyester resin is suitable.
又被記録体としては、普通紙を用いることもてきるが発
色感度を高めるために、ポリエステル系樹脂又はポリア
ミド系樹脂などをコートした紙、あるいはポリプロピレ
ン、ポリ塩化ビニル又はポリエステルなどの合成紙が使
用される。Plain paper can be used as the recording medium, but to increase color sensitivity, paper coated with polyester resin or polyamide resin, or synthetic paper such as polypropylene, polyvinyl chloride, or polyester is used. be done.
本発明の色素は鮮明なイエロー色であるため、例えば下
記構造式
で示されるマゼンタ色素及び下記構造式で示されるシア
ン色素と組み合わせてフルカラーを得るのに適している
。Since the dye of the present invention has a vivid yellow color, it is suitable for obtaining a full color in combination with, for example, a magenta dye represented by the following structural formula and a cyan dye represented by the following structural formula.
（発明の効果）
本発明によれば、−数式（１）で示され良好な転写性を
有するビストリシアノスチレン系色素を用いることによ
り、鮮やかなイエロー色の感熱転写記録が得られる。(Effects of the Invention) According to the present invention, by using a bistricyanostyrene dye represented by formula (1) and having good transferability, a bright yellow thermal transfer recording can be obtained.
以下実施例を挙げて本発明を具体的に説明するが、本実
施例は本発明を限定するものではない。EXAMPLES The present invention will be specifically explained below with reference to Examples, but these Examples do not limit the present invention.
実施例 １
（１）色素の製造
３．３“−ジエチルアミノ−６，６゛ −ジホルミルジ
フェニルメタン９．４ｇとマロノニトリル５．１ｇをエ
タノール９６１ｄに溶解し、それにピペリジン０．４ｇ
を添加して還流下１時間反応させた。反応終了後、冷却
し析出した結晶をろ過した。得られた粗結晶をカラムク
ロマト精製を実施し、３．３゜ジエチルアミノ−６，６
”−（β、β−ジシアノビニル）−ジフェニルメタン４
．２ｇ（収率３５％）を得た。 融点 ２１３〜２１
４℃
本品の極大吸収波長（酢酸エチル）は４３８ｎｍであっ
た。Example 1 (1) Production of dye 3. 9.4 g of 3"-diethylamino-6,6"-diformyldiphenylmethane and 5.1 g of malononitrile were dissolved in ethanol 961d, and 0.4 g of piperidine was dissolved therein.
was added and reacted under reflux for 1 hour. After the reaction was completed, it was cooled and the precipitated crystals were filtered. The obtained crude crystals were purified by column chromatography to obtain 3.3゜diethylamino-6,6
”-(β,β-dicyanovinyl)-diphenylmethane 4
．． 2 g (yield 35%) was obtained. Melting point 213-21
4°C The maximum absorption wavelength (ethyl acetate) of this product was 438 nm.
（２）転写シート及び被転写材の作成
上記（１）で得られた色素 ３部、ポリビニルブチラー
ル樹脂７部及びメチルエチルケトン４５部、トルエン４
５部のインク組成物をボールミルにより充分混練した後
、背面に耐熱処理した６μｍ厚のポリエチレンテレフタ
レートフィルムに、乾ｉｉ布ｔが１．０ｇ／％になるよ
うにバーコータを用いて塗布し、乾燥して本発明の転写
シートを得た。(2) Preparation of transfer sheet and transfer material 3 parts of the dye obtained in (1) above, 7 parts of polyvinyl butyral resin, 45 parts of methyl ethyl ketone, 4 parts of toluene
After thoroughly kneading 5 parts of the ink composition using a ball mill, it was coated on a 6 μm thick polyethylene terephthalate film whose back side was heat-resistant treated using a bar coater so that the dry cloth t was 1.0 g/%, and dried. A transfer sheet of the present invention was obtained.
次に、ポリエステル樹脂１４部、メチルエチルケトン４
３部、トルエン４３部の塗工液を乾燥時１０．０ｇ／ｒ
ｒｆになる割合で基材シートである合成紙に塗布し、乾
燥して被転写材を得た。Next, 14 parts of polyester resin, 4 parts of methyl ethyl ketone
3 parts of toluene and 43 parts of toluene at a dry rate of 10.0 g/r.
It was applied to a synthetic paper as a base sheet at a ratio of RF and dried to obtain a transfer material.
（３）転写記録
前記の本発明転写シートと前記被転写材とを対向させ、
転写シートの裏面から感熱ヘッドを用いて加熱すること
により記録を行い、鮮明なイエロー色の高色濃度記録が
得られた。記録濃度（ＯＤ）は、２．２０であった。(3) Transfer recording The above-mentioned transfer sheet of the present invention and the above-mentioned transfer target material are faced to each other,
Recording was performed by heating the transfer sheet from the back side using a thermal head, and a clear yellow high color density record was obtained. The recording density (OD) was 2.20.
実施例 ２〜３６
以下実施例１と同様にして表−１の色素を合成し、それ
ぞれ悠然転写を行って色濃度の高い鮮明なイエロー色記
録が得られた。Examples 2 to 36 The dyes shown in Table 1 were synthesized in the same manner as in Example 1, and each was transferred slowly to obtain a clear yellow color record with high color density.
Claims (1)
水素原子、置換又は非置換アルキル基、シクロアルキル
基、アラルキル基、アリール基であるか、あるいはＸと
一緒に５員環又は６員環を形成する原子又は原子団を表
し、Ｒ＿２、及びＲ＿４は同一又は異なってもよく、水
素原子、置換又は非置換アルキル基、シクロアルキル基
、アラルキル基、アリール基を表す。なお、Ｒ＿１とＲ
＿２およびＲ＿３とＲ＿４は酸素原子、窒素原子または
硫黄原子を含有してもよい５員環又は６員環を形成して
も良い。 Ｒ＿５は同一又は異なってもよく電子吸引基を表し、Ａ
は２価の連結基を表す。Ｚはメチン基または窒素原子を
表し、Ｘは水素原子であるか、あるいはＲ＿１及びＲ＿
３とそれぞれ一緒に５員環又は６員環を形成する原子又
は原子団を表す。 で示される感熱転写記録用色素。[Claims] General formula (1) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (1) In the formula, R_1 and R_3 may be the same or different,
R_2 and R_4 represent a hydrogen atom, a substituted or unsubstituted alkyl group, a cycloalkyl group, an aralkyl group, an aryl group, or an atom or atomic group that forms a 5-membered or 6-membered ring together with X, and R_2 and R_4 are They may be the same or different and represent a hydrogen atom, a substituted or unsubstituted alkyl group, a cycloalkyl group, an aralkyl group, or an aryl group. In addition, R_1 and R
_2, R_3 and R_4 may form a 5-membered ring or a 6-membered ring which may contain an oxygen atom, nitrogen atom or sulfur atom. R_5 may be the same or different and represents an electron-withdrawing group, and A
represents a divalent linking group. Z represents a methine group or a nitrogen atom, X is a hydrogen atom, or R_1 and R_
Represents an atom or atomic group that forms a 5-membered ring or a 6-membered ring together with 3, respectively. A dye for thermal transfer recording shown in
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2097704A JPH03295687A (en) | 1990-04-16 | 1990-04-16 | Dyestuff for thermal transfer recording |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2097704A JPH03295687A (en) | 1990-04-16 | 1990-04-16 | Dyestuff for thermal transfer recording |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH03295687A true JPH03295687A (en) | 1991-12-26 |
Family
ID=14199312
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2097704A Pending JPH03295687A (en) | 1990-04-16 | 1990-04-16 | Dyestuff for thermal transfer recording |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH03295687A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015083606A1 (en) * | 2013-12-05 | 2015-06-11 | 株式会社Adeka | Novel compound and composition containing novel compound |
-
1990
- 1990-04-16 JP JP2097704A patent/JPH03295687A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015083606A1 (en) * | 2013-12-05 | 2015-06-11 | 株式会社Adeka | Novel compound and composition containing novel compound |
| CN105473666A (en) * | 2013-12-05 | 2016-04-06 | 株式会社艾迪科 | Novel compound and composition containing novel compound |
| JPWO2015083606A1 (en) * | 2013-12-05 | 2017-03-16 | 株式会社Adeka | NOVEL COMPOUND AND COMPOSITION CONTAINING THE COMPOUND |
| TWI664244B (en) * | 2013-12-05 | 2019-07-01 | 日商艾迪科股份有限公司 | Novel compound and composition containing the same |
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