JPH0447635B2 - - Google Patents
Info
- Publication number
- JPH0447635B2 JPH0447635B2 JP58137020A JP13702083A JPH0447635B2 JP H0447635 B2 JPH0447635 B2 JP H0447635B2 JP 58137020 A JP58137020 A JP 58137020A JP 13702083 A JP13702083 A JP 13702083A JP H0447635 B2 JPH0447635 B2 JP H0447635B2
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- pyridone
- cyano
- hydroxy
- 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
- 238000012546 transfer Methods 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- -1 methoxyethyl group Chemical group 0.000 description 41
- 239000000975 dye Substances 0.000 description 22
- 239000000976 ink Substances 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- 239000000123 paper Substances 0.000 description 11
- 239000011347 resin Substances 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000012360 testing method Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- 239000000987 azo dye Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- DAAOZBOEUSKYOG-UHFFFAOYSA-N 1-amino-4-(methylamino)-9,10-dioxoanthracene-2-carboxylic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=C(C(O)=O)C=C2NC DAAOZBOEUSKYOG-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
- GQTIFDAKWBGUAT-UHFFFAOYSA-N 2-hydroxy-4-methyl-5-[(4-methylphenyl)diazenyl]-6-oxo-1H-pyridine-3-carbonitrile Chemical compound CC1=CC=C(C=C1)N=NC1=C(NC(C(=C1C)C#N)=O)O GQTIFDAKWBGUAT-UHFFFAOYSA-N 0.000 description 1
- OIMRCLBUTPELBG-UHFFFAOYSA-N 2-hydroxy-4-methyl-6-oxo-5-phenyldiazenyl-1H-pyridine-3-carbonitrile Chemical compound OC1=C(C(=C(C(N1)=O)C#N)C)N=NC1=CC=CC=C1 OIMRCLBUTPELBG-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- ONCRBDLRDQRCOM-UHFFFAOYSA-N C(C)N1C(C(=C(C(=C1O)N=NC1=CC=CC=C1)C)C#N)=O Chemical compound C(C)N1C(C(=C(C(=C1O)N=NC1=CC=CC=C1)C)C#N)=O ONCRBDLRDQRCOM-UHFFFAOYSA-N 0.000 description 1
- HDDAPNNXKKWRTK-UHFFFAOYSA-N C1=CC(=CC=C1Cl)N=NC1=C(O)N(CC)C(=O)C(C#N)=C1C Chemical compound C1=CC(=CC=C1Cl)N=NC1=C(O)N(CC)C(=O)C(C#N)=C1C HDDAPNNXKKWRTK-UHFFFAOYSA-N 0.000 description 1
- RABUCGAWPAORHS-UHFFFAOYSA-N CN1C(O)=C(N=NC2=CC=CC=C2[N+]([O-])=O)C(C)=C(C#N)C1=O Chemical compound CN1C(O)=C(N=NC2=CC=CC=C2[N+]([O-])=O)C(C)=C(C#N)C1=O RABUCGAWPAORHS-UHFFFAOYSA-N 0.000 description 1
- UZRPBIRBAIPNMC-UHFFFAOYSA-N COC1=C(C=CC=C1)N=NC=1C(=C(C(N(C=1O)CC)=O)C#N)C Chemical compound COC1=C(C=CC=C1)N=NC=1C(=C(C(N(C=1O)CC)=O)C#N)C UZRPBIRBAIPNMC-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004962 Polyamide-imide Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 229920013820 alkyl cellulose Polymers 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- NKWPZUCBCARRDP-UHFFFAOYSA-L calcium bicarbonate Chemical compound [Ca+2].OC([O-])=O.OC([O-])=O NKWPZUCBCARRDP-UHFFFAOYSA-L 0.000 description 1
- 229910000020 calcium bicarbonate Inorganic materials 0.000 description 1
- 239000003990 capacitor Substances 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
- 238000007796 conventional method Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000011086 glassine Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 238000007731 hot pressing Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000002156 mixing Methods 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
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- WLFXSECCHULRRO-UHFFFAOYSA-N pyridine-2,6-diol Chemical compound OC1=CC=CC(O)=N1 WLFXSECCHULRRO-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- NLDYACGHTUPAQU-UHFFFAOYSA-N tetracyanoethylene Chemical group N#CC(C#N)=C(C#N)C#N NLDYACGHTUPAQU-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 238000010023 transfer printing Methods 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
- 239000001043 yellow dye 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
- B41M5/382—Contact thermal transfer or sublimation processes
- B41M5/385—Contact thermal transfer or sublimation processes characterised by the transferable dyes or pigments
- B41M5/388—Azo dyes
Description
本発明はピリドンアゾ系感熱転写記録用色素に
関するものである。
現在、テレビ、CRTカラーデイスプレー、カ
ラーフアクシミリ、磁気カメラなどからカラーハ
ードコピーを得る方法として昇華型感熱転写記録
方法が提案されている。
この方法は昇華性色素を塗布した転写シートを
感熱記録ヘツドで加熱して被記録体に色素を昇華
転写し、カラー記録を得る方法であるが、感熱ヘ
ツドに印加するエネルギーを調整することにより
色素の昇華量を制御できるため、階調表現が容易
であり、他の記録方法に比べ特にフルカラーハー
ドコピーを得るのに有利である。
ところでこの記録方法に使用する色素として
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。
光、湿気、薬品などに対して安定なこと。
合成が容易なこと。
従来、この記録方法には、主に、ポリエステル
繊維の転写捺染用色素が検討されてきたが、上記
の条件を満足し、実用に供し得るものはほとんど
存在せず、充分な色濃度で堅牢な記録が得られな
かつた。
我々は種々の色素について検討を行なつた結果
下記一般色〔〕
（式中、
The present invention relates to a pyridone azo dye for thermal transfer recording. Currently, a dye sublimation thermal transfer recording method has been proposed as a method for obtaining color hard copies from televisions, CRT color displays, color facsimile machines, magnetic cameras, etc. In this method, a transfer sheet coated with a sublimable dye is heated with a heat-sensitive recording head to sublimate and transfer the dye to the recording medium to obtain color recording. Since the amount of sublimation can be controlled, it is easy to express gradation, and compared to other recording methods, it is especially advantageous for obtaining full-color hard copies. By the way, the dye used in this recording method 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 light, moisture, chemicals, etc. Easy to synthesize. Conventionally, dyes for transfer printing of polyester fibers have been mainly studied for this recording method, but there are almost no dyes that satisfy the above conditions and can be put to practical use. Records could not be obtained. We investigated various pigments and found the following general colors: (In the formula,
【式】は、低級アルキル基、
低級アルコキシ基、トリフルオロメチル基、ニト
ロ基もしくはハロゲン原子で置換されていてもよ
いフエニル基を表わし、Ｒは低級アルキル基、低
級アルコキシアルキル基、アリル基又は水素原子
を表わす）で示されるビリドンアゾ系色素が前記
の条件、特に，、を満足するイエロー色の
色素であり、これらを用いることにより充分な色
濃度で堅牢な記録が得られることを見い出し、本
発明を完成した。
前記一般式〔〕において、[Formula] represents a lower alkyl group, a lower alkoxy group, a trifluoromethyl group, a nitro group, or a phenyl group optionally substituted with a halogen atom, and R is a lower alkyl group, a lower alkoxyalkyl group, an allyl group, or hydrogen. It has been discovered that the biridone azo dye represented by (representing an atom) is a yellow dye that satisfies the above-mentioned conditions, in particular, and that solid recording with sufficient color density can be obtained by using these, and the present invention has been made based on the present invention. completed. In the general formula [],
【式】は
メチル基、エチル基、ｎ−プロピル基、iso−プ
ロピル基、ｎ−ブチル基等の低級アルキル基、メ
トキシ基、エトキシ基、ｎ−ブトキシ基等の低級
アルコキシ基、トリフルオロメチル基、ニトロ基
もしくは塩素原子、臭素原子等のハロゲン原子で
置換されていてもよいフエニル基を表わし、Ｒは
メチル基、エチル基、ｎ−プロピル基、iso−プ
ロピル基、ｎ−ブチル基等の低級アルキル基、メ
トキシエチル基、メトキシプロピル基、エトキシ
エチル基等の低級アルコキシアルキル基、アリル
基又は水素原子を表わす。
特に、[Formula] is a lower alkyl group such as methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, lower alkoxy group such as methoxy group, ethoxy group, n-butoxy group, or trifluoromethyl group. , represents a phenyl group which may be substituted with a nitro group or a halogen atom such as a chlorine atom or a bromine atom, and R represents a lower group such as a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, etc. It represents an alkyl group, a lower alkoxyalkyl group such as a methoxyethyl group, a methoxypropyl group, or an ethoxyethyl group, an allyl group, or a hydrogen atom. especially,
【式】がフエニル基、又は、低
級アルキル基もしくは塩素原子を持つフエニル基
で、Ｒが低級アルキル基及びアリル基で表わされ
る色素が好ましい。
なお、本発明でいう「低級」とは「炭素原子数
１〜４」を意味する。
本発明色素の具体例としては以下のものが挙げ
られる。
Ｎ−メチル−３−シアノ−４−メチル、５−フ
エニルアゾ−６−ヒドロ−２−ピリドン、Ｎ−エ
チル−３−シアノ−４−メチル−５−フエニルア
ゾ−６−ヒドロキシ−２−ピリドン、Ｎ−(n)−プ
ロピル−３−シアノ−４−メチル−５−フエニル
アゾ−６−ヒドロキシ−２−ピリドン、Ｎ−
（iso）−プロピル−３−シアノ−４−メチル−５
−フエニルアゾ−６−ヒドロキシ−２−ピリド
ン、Ｎ−(n)−ブチル−３−シアノ−４−メチル−
５−フエニルアゾ−６−ヒドロキシ−２−ピリド
ン、Ｎ−（iso）−ブチル−３−シアノ−４−メチ
ル−５−フエニルアゾ−６−ヒドロキシ−２−ピ
リドン、Ｎ−（β′−メトキシエチル）−３−シアノ
−４−メチル−５−フエニルアゾ−６−ヒドロキ
シ−２−ピリドン、Ｎ−（β′−エトキシエチル）−
３−シアノ−４−メチル−５−フエニルアゾ−６
−ヒドロキシ−２−ピリドン、Ｎ−（γ′−メトキ
シプロピル）−３−シアノ−４−メチル−５−フ
エニルアゾ−６−ヒドロキシ−２−ピリドン、Ｎ
−メチル−３−シアノ−４−メチル−５−（2′−
メチルフエニルアゾ）−６−ヒドロキシ−２−ピ
リドン、Ｎ−エチル−３−シアノ−４−メチル−
５−（2′−メチルフエニルアゾ）−６−ヒドロキシ
−２−ピリドン、Ｎ−メチル−３−シアノ−４−
メチル−５−（3′−メチルフエニルアゾ）−６−ヒ
ドロキシ−２−ピリドン、Ｎ−エチル−３−シア
ノ−４−メチル−５−（3′−メチルフエニルアゾ）
−６−ヒドロキシ−２−ピリドン、Ｎ−メチル−
３−シアノ−４−メチル−５−（4′−メチルフエ
ニルアゾ）−６−ヒドロキシ−２−ピリドン、Ｎ
−エチル−３−シアノ−４−メチル−５−（4′−
メチルフエニルアゾ）−６−ヒドロキシ−２−ピ
リドン、Ｎ−メチル−３−シアノ−４−メチル−
５−（4′−エチルフエニルアゾ）−６−ヒドロキシ
−２−ピリドン、Ｎ−エチル−３−シアノ−４−
メチル−５−（2′エチルフエニルアゾ）−６−ヒド
ロキシ−２−ピリドン、Ｎ−メチル−３−シアノ
−４−メチル−５−（2′，4′−ジメチルフエニル
アゾ）−６−ヒドロキシ−２−ピリドン、Ｎ−エ
チル−３−シアノ−４−メチル−５−（2′，4′−
ジメチルフエニルアゾ）−６−ヒドロキシ−２−
ピリドン、Ｎ−メチル−３−シアノ−４−メチル
５−（2′6′−ジメチルフエニルアゾ）−６−ヒドロ
キシ−２−ピリドン、Ｎ−メチル−３−シアノ−
４−メチル−５−（2′−メトキシフエニルアゾ）−
６−ヒドロキシ−２−ピリドン、Ｎ−エチル−３
−シアノ−４−メチル−５−（2′−メトキシフエ
ニルアゾ）−６−ヒドロキシ−２−ピリドン、Ｎ
−メチル−３−シアノ−４−メチル−５−（4′−
メトキシフエニルアゾ）−６−ヒドロキシ−２−
ピリドン、Ｎ−メチル−３−シアノ−４−メチル
−５−（4′−エトキシフエニルアゾ）−６−ヒドロ
キシ−２−ピリドン、Ｎ−メチル−３−シアノ−
４−メチル−５−（2′−トリフルオロメチルフエ
ニルアゾ）−６−ヒドロキシ−２−ピリドン、Ｎ
−エチル−３−シアノ−４−メチル−５−（2′−
トリフルオロメチルフエニルアゾ）−６−ヒドロ
キシ−２−ピリドン、Ｎ−メチル−３−シアノ−
４−メチル−５−（3′−トリフルオロメチルフエ
ニルアゾ）−６−ヒドロキシ−２−ピリドン、Ｎ
−エチル−３−シアノ−４−メチル−５−（3′−
トリフルオロメチルフエニルアゾ）−６−ヒドロ
キシ−２−ピリドン、Ｎ−メチル−３−シアノ−
４−メチル−５−（4′−トリフルオロメチルフエ
ニルアゾ）−６−ヒドロキシ−２−ピリドン、Ｎ
−エチル−３−シアノ−４−メチル−５−（4′−
トリフルオロメチルフエニルアゾ）−６−ヒドロ
キシ−２−ピリドン、Ｎ−メチル−３−シアノ−
４−メチル−５−（2′−ニトロフエニルアゾ）−６
−ヒドロキシ−２−ピリドン、Ｎ−メチル−３−
シアノ−４−メチル−５−（3′−ニトロフエニル
アゾ）−６−ヒドロキシ−２−ピリドン、Ｎ−メ
チル−３−シアノ−４−メチル−５−（4′−ニト
ロフエニルアゾ）−６−ヒドロキシ−２−ピリド
ン、Ｎ−メチル−３−シアノ−４−メチル−５−
（2′−クロロフエニルアゾ）−６−ヒドロキシ−２
−ピリドン、Ｎ−エチル−３−シアノ−４−メチ
ル−５−（2′−クロロフエニルアゾ）−６−ヒドロ
キシ−２−ピリドン、Ｎ−メチル−３−シアノ−
４−メチル−５−（3′−クロロフエニルアゾ）−６
−ヒドロキシ−２−ピリドン、Ｎ−メチル−３−
シアノ−４−メチル−５−（4′クロロフエニルア
ゾ）−６−ヒドロキシ−２−ピリドン、Ｎ−エチ
ル−３−シアノ−４−メチル−５−（4′−クロロ
フエニルアゾ）−６−ヒドロキシ−２−ピリドン、
Ｎ−メチル−３−シアノ−４−メチル−５−
（2′−フルオロフエニルアゾ−６−ヒドロキシ−
２−ピリドン、Ｎ−エチル−３−シアノ−メチル
−５−（2′−フルオロフエニルアゾ）−６−ヒドロ
キシ−２−ピリドン、Ｎ−メチル−３−シアノ−
４−メチル−５−（3′−フルオロフエニルアゾ）−
６−ヒドロキシ−２−ピリドン、Ｎ−エチル−３
−シアノ−４−メチル−５−（3′−フルオロフエ
ニルアゾ）−６−ヒドロキシ−２−ピリドン、Ｎ
−メチル−３−シアノ−４−メチル−５−（4′−
フルオロフエニルアゾ）−６−ヒドロキシ−２−
ピリドン、Ｎ−エチル−３−シアノ−４−メチル
−５−（4′−フルオロフエニルアゾ）−６−ヒドロ
キシ−２−ピリドン、Ｎ−アリル−３−シアノ−
４−メチル−５−フエニルアゾ−６−ヒドロキシ
−２−ピリドン、Ｎ−アリル−３−シアノ−４−
メチル−５−（2′−メチルフエニルアゾ）−６−ヒ
ドロキシ−２−ピリドン、Ｎ−アリル−３−シア
ノ−４−メチル−５−（3′−メチルフエニルアゾ）
−６−ヒドロキシ−２−ピリドン、Ｎ−アリル−
３−シアノ−４−メチル−５−（4′−メチルフエ
ニルアゾ）−６−ヒドロキシ−２−ピリドン、Ｎ
−アリル−３−シアノ−４−メチル−５−（4′−
エチルフエニルアゾ）−６−ヒドロキシ−２−ピ
リドン、Ｎ−アリル−３−シアノ−４−メチル−
５−（2′，4′−ジメチルフエニルアゾ）−６−ヒド
ロキシ−２−ピリドン、Ｎ−アリル−３−シアノ
−４−メチル−５−（4′−メトキシフエニルアゾ）
−６−ヒドロキシ−２−ピリドン、Ｎ−アリル−
３−シアノ−４−メチル−５−（4′−エトキシフ
エニルアゾ）−６−ヒドロキシ−２−ピリドン、
Ｎ−アリル−３−シアノ−４−メチル−５−
（2′−トリフルオロメチルフエニルアゾ）−６−ヒ
ドロキシ−２−ピリドン、Ｎ−アリル−３−シア
ノ−４−メチル−５−（3′−トリフルオロメチル
フエニルアゾ）−６−ヒドロキシ−２−ピリドン、
Ｎ−アリル−３−シアノ−４−メチル−５−
（4′−トリフルオロメチルフエニルアゾ）−６−ヒ
ドロキシ−２−ピリドン、Ｎ−アリル−３−シア
ノ−４−メチル−５−（2′−ニトロフエニルアゾ）
−６−ヒドロキシ−２−ピリドン、Ｎ−アリル−
３−シアノ−４−メチル−５−（4′−ニトロフエ
ニルアゾ）−６−ヒドロキシ−２−ピリドン、Ｎ
−アリル−３−シアノ−４−メチル−５−（2′ク
ロロフエニルアゾ）−６−ヒドロキシ−２−ピリ
ドン、Ｎ−アリル−３−シアノ−４−メチル−５
−（3′−クロロフエニルアゾ）−６−ヒドロキシ−
２−ピリドン、Ｎ−アリル−３−シアノ−４−メ
チル−５−（4′−クロロフエニルアゾ）−６−ヒド
ロキシ−２−ピリドン、Ｎ−アリル−３−シアノ
−４−メチル−５−（2′−フルオロフエニルアゾ）
−６−ヒドロキシ−２−ピリドン、Ｎ−アリル−
３−シアノ−４−メチル−５−（3′−フルオロフ
エニルアゾ）−６−ヒドロキシ−２−ピリドン、
Ｎ−アリル−３−シアノ−４−メチル−５−
（4′−フルオロフエニルアゾ）−６−ヒドロキシ−
２−ピリドン、３−シアノ−４−メチル−５−フ
エニルアゾ−６−ヒドロキシ−２−ピリドン、３
−シアノ−４−メチル−５−（4′−メトキシフエ
ニルアゾ）−６−ヒドロキシ−２−ピリドン、３
−シアノ−４−メチル−５−（3′−クロロフエニ
ルアゾ）−６−ヒドロキシ−２−ピリドン、３−
シアノ−４−メチル−５−（3′−トリフルオロメ
チルフエニルアゾ）−６−ヒドロキシ−２−ピリ
ドン、３−シアノ−４−メチル−５−（3′−フル
オロフエニルアゾ）−６−ヒドロキシ−２−ピリ
ドン、３−シアノ−４−メチル−５−（4′−クロ
ロフエニルアゾ）−６−ヒドロキシ−２−ピリド
ン。
これらの色素の製造方法としては、公知の方法
に準い、例えば、下記一般式〔〕
（式中A dye in which [Formula] is a phenyl group, a lower alkyl group, or a phenyl group having a chlorine atom, and R is a lower alkyl group or an allyl group is preferred. In addition, "lower" as used in the present invention means "carbon number 1 to 4". Specific examples of the dyes of the present invention include the following. N-Methyl-3-cyano-4-methyl, 5-phenylazo-6-hydro-2-pyridone, N-ethyl-3-cyano-4-methyl-5-phenylazo-6-hydroxy-2-pyridone, N- (n)-Propyl-3-cyano-4-methyl-5-phenylazo-6-hydroxy-2-pyridone, N-
(iso)-propyl-3-cyano-4-methyl-5
-phenylazo-6-hydroxy-2-pyridone, N-(n)-butyl-3-cyano-4-methyl-
5-phenylazo-6-hydroxy-2-pyridone, N-(iso)-butyl-3-cyano-4-methyl-5-phenylazo-6-hydroxy-2-pyridone, N-(β'-methoxyethyl)- 3-cyano-4-methyl-5-phenylazo-6-hydroxy-2-pyridone, N-(β'-ethoxyethyl)-
3-cyano-4-methyl-5-phenylazo-6
-Hydroxy-2-pyridone, N-(γ'-methoxypropyl)-3-cyano-4-methyl-5-phenylazo-6-hydroxy-2-pyridone, N
-Methyl-3-cyano-4-methyl-5-(2'-
methylphenylazo)-6-hydroxy-2-pyridone, N-ethyl-3-cyano-4-methyl-
5-(2'-methylphenylazo)-6-hydroxy-2-pyridone, N-methyl-3-cyano-4-
Methyl-5-(3'-methylphenylazo)-6-hydroxy-2-pyridone, N-ethyl-3-cyano-4-methyl-5-(3'-methylphenylazo)
-6-hydroxy-2-pyridone, N-methyl-
3-cyano-4-methyl-5-(4'-methylphenylazo)-6-hydroxy-2-pyridone, N
-ethyl-3-cyano-4-methyl-5-(4'-
methylphenylazo)-6-hydroxy-2-pyridone, N-methyl-3-cyano-4-methyl-
5-(4'-ethylphenylazo)-6-hydroxy-2-pyridone, N-ethyl-3-cyano-4-
Methyl-5-(2'ethylphenylazo)-6-hydroxy-2-pyridone, N-methyl-3-cyano-4-methyl-5-(2',4'-dimethylphenylazo)-6- Hydroxy-2-pyridone, N-ethyl-3-cyano-4-methyl-5-(2',4'-
dimethylphenylazo)-6-hydroxy-2-
Pyridone, N-methyl-3-cyano-4-methyl5-(2'6'-dimethylphenylazo)-6-hydroxy-2-pyridone, N-methyl-3-cyano-
4-Methyl-5-(2'-methoxyphenylazo)-
6-hydroxy-2-pyridone, N-ethyl-3
-cyano-4-methyl-5-(2'-methoxyphenylazo)-6-hydroxy-2-pyridone, N
-Methyl-3-cyano-4-methyl-5-(4'-
methoxyphenylazo)-6-hydroxy-2-
Pyridone, N-methyl-3-cyano-4-methyl-5-(4'-ethoxyphenylazo)-6-hydroxy-2-pyridone, N-methyl-3-cyano-
4-Methyl-5-(2'-trifluoromethylphenylazo)-6-hydroxy-2-pyridone, N
-ethyl-3-cyano-4-methyl-5-(2'-
trifluoromethylphenylazo)-6-hydroxy-2-pyridone, N-methyl-3-cyano-
4-Methyl-5-(3'-trifluoromethylphenylazo)-6-hydroxy-2-pyridone, N
-ethyl-3-cyano-4-methyl-5-(3'-
trifluoromethylphenylazo)-6-hydroxy-2-pyridone, N-methyl-3-cyano-
4-Methyl-5-(4'-trifluoromethylphenylazo)-6-hydroxy-2-pyridone, N
-ethyl-3-cyano-4-methyl-5-(4'-
trifluoromethylphenylazo)-6-hydroxy-2-pyridone, N-methyl-3-cyano-
4-Methyl-5-(2'-nitrophenylazo)-6
-Hydroxy-2-pyridone, N-methyl-3-
Cyano-4-methyl-5-(3'-nitrophenylazo)-6-hydroxy-2-pyridone, N-methyl-3-cyano-4-methyl-5-(4'-nitrophenylazo)- 6-hydroxy-2-pyridone, N-methyl-3-cyano-4-methyl-5-
(2'-chlorophenylazo)-6-hydroxy-2
-Pyridone, N-ethyl-3-cyano-4-methyl-5-(2'-chlorophenylazo)-6-hydroxy-2-pyridone, N-methyl-3-cyano-
4-Methyl-5-(3'-chlorophenylazo)-6
-Hydroxy-2-pyridone, N-methyl-3-
Cyano-4-methyl-5-(4'-chlorophenylazo)-6-hydroxy-2-pyridone, N-ethyl-3-cyano-4-methyl-5-(4'-chlorophenylazo)-6-hydroxy -2-pyridone,
N-methyl-3-cyano-4-methyl-5-
(2'-fluorophenylazo-6-hydroxy-
2-pyridone, N-ethyl-3-cyano-methyl-5-(2'-fluorophenylazo)-6-hydroxy-2-pyridone, N-methyl-3-cyano-
4-Methyl-5-(3'-fluorophenylazo)-
6-hydroxy-2-pyridone, N-ethyl-3
-cyano-4-methyl-5-(3'-fluorophenylazo)-6-hydroxy-2-pyridone, N
-Methyl-3-cyano-4-methyl-5-(4'-
Fluorophenylazo)-6-hydroxy-2-
Pyridone, N-ethyl-3-cyano-4-methyl-5-(4'-fluorophenylazo)-6-hydroxy-2-pyridone, N-allyl-3-cyano-
4-Methyl-5-phenylazo-6-hydroxy-2-pyridone, N-allyl-3-cyano-4-
Methyl-5-(2'-methylphenylazo)-6-hydroxy-2-pyridone, N-allyl-3-cyano-4-methyl-5-(3'-methylphenylazo)
-6-hydroxy-2-pyridone, N-allyl-
3-cyano-4-methyl-5-(4'-methylphenylazo)-6-hydroxy-2-pyridone, N
-Allyl-3-cyano-4-methyl-5-(4'-
ethylphenylazo)-6-hydroxy-2-pyridone, N-allyl-3-cyano-4-methyl-
5-(2',4'-dimethylphenylazo)-6-hydroxy-2-pyridone, N-allyl-3-cyano-4-methyl-5-(4'-methoxyphenylazo)
-6-hydroxy-2-pyridone, N-allyl-
3-cyano-4-methyl-5-(4'-ethoxyphenylazo)-6-hydroxy-2-pyridone,
N-allyl-3-cyano-4-methyl-5-
(2'-trifluoromethylphenylazo)-6-hydroxy-2-pyridone, N-allyl-3-cyano-4-methyl-5-(3'-trifluoromethylphenylazo)-6-hydroxy- 2-pyridone,
N-allyl-3-cyano-4-methyl-5-
(4'-trifluoromethylphenylazo)-6-hydroxy-2-pyridone, N-allyl-3-cyano-4-methyl-5-(2'-nitrophenylazo)
-6-hydroxy-2-pyridone, N-allyl-
3-cyano-4-methyl-5-(4'-nitrophenylazo)-6-hydroxy-2-pyridone, N
-Allyl-3-cyano-4-methyl-5-(2'chlorophenylazo)-6-hydroxy-2-pyridone, N-allyl-3-cyano-4-methyl-5
-(3'-chlorophenylazo)-6-hydroxy-
2-pyridone, N-allyl-3-cyano-4-methyl-5-(4'-chlorophenylazo)-6-hydroxy-2-pyridone, N-allyl-3-cyano-4-methyl-5-( 2′-fluorophenylazo)
-6-hydroxy-2-pyridone, N-allyl-
3-cyano-4-methyl-5-(3'-fluorophenylazo)-6-hydroxy-2-pyridone,
N-allyl-3-cyano-4-methyl-5-
(4'-fluorophenylazo)-6-hydroxy-
2-pyridone, 3-cyano-4-methyl-5-phenylazo-6-hydroxy-2-pyridone, 3
-cyano-4-methyl-5-(4'-methoxyphenylazo)-6-hydroxy-2-pyridone, 3
-cyano-4-methyl-5-(3'-chlorophenylazo)-6-hydroxy-2-pyridone, 3-
Cyano-4-methyl-5-(3'-trifluoromethylphenylazo)-6-hydroxy-2-pyridone, 3-cyano-4-methyl-5-(3'-fluorophenylazo)-6- Hydroxy-2-pyridone, 3-cyano-4-methyl-5-(4'-chlorophenylazo)-6-hydroxy-2-pyridone. These dyes can be produced according to known methods, such as the following general formula [] (In the ceremony
【式】は、前記一般式〔〕に
おけると同一の意味を表わす）で示されるアニリ
ン類を常法に従いジアゾ化し、下記一般式〔〕
（式中、Ｒは前記一般式〔〕におけると同一
の意味を表わす）で示されるピリドン類とカツプ
リングするか、又は、３−シアノ−４−メチル−
６−ヒドロキシ−２−ピリドンにカツプリングし
て得られる下記一般式〔〕
（式中[Formula] represents the same meaning as in the above general formula []) is diazotized according to a conventional method, and the following general formula [] (wherein R represents the same meaning as in the above general formula []), or 3-cyano-4-methyl-
The following general formula obtained by coupling to 6-hydroxy-2-pyridone [] (In the ceremony
【式】は前記一般式〔〕にお
けると同一の意味を表わす）で示されるアゾ色素
に更に下記一般式〔〕
Ｒ−Ｘ ……〔〕
（式中、Ｒは前記一般式〔〕におけると同一
の意味を表わし、Ｘはハロゲン原子を表わす）あ
るいは、下記一般式〔〕
（式中、Ｒは前記一般式〔〕におけると同一
の意味を表わす）で示されるアルキル化剤を作用
させることにより容易に得ることができる。
本発明の色素をもちいて感熱転写記録用インキ
を製造する方法としては、色素を適当な樹脂、溶
剤、水等と混合し、該記録用インキとすればよ
い。また熱転写方法としては、上記で得られたイ
ンキを適当な基材上に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
背面から感熱記録ヘツドで加熱及び加圧する方法
を挙げることができ、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。
上記のインキを調製するための樹脂としては、
通常の印刷インキに使用されるもので良く、ロジ
ン系、フエノール系、キシレン系、石油系、ビニ
ル系、ポリアミド系、アルキツド系、ニトロセル
ロース系、アルキルセルロースアルキルセルロー
ス類などの油性系の樹脂あるいはマレイン酸系、
アクリル酸系、カゼイン、シエラツク、ニカワな
どの水性系樹脂が使用できる。又、インキ調製の
ための溶剤としては、メタノール、エタノール、
プロンパノール、ブタノ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、ベンゼン、トルエン、キシレンな
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、シク
ロヘキサノンなどのケトン類、リグロイン、シク
ロヘキサン、ケロシンなどの炭化水素類、ジメチ
ルホルムアミドなどが使用できるが、水性系樹脂
を使用の場合には水または水と上記の溶剤類を混
合し使用することもできる。
インキを塗布する基材としては、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、これら
の基材は感熱記録ヘツドから色素への伝熱効率を
良くするため５〜50μm程度の厚さが適当である。
又、被記録体としては、普通紙を用いることも
できるが色素の発色を良くするために、それらに
色素と相溶性の良好な樹脂をコーテイングしたも
の、含浸したものあるいは樹脂のフイルムをラミ
ネートしたものや、アセチル化処理した特殊な加
工紙を使用することにより良好な記録ができる。
又、各種樹脂のフイルムあるいはそれらから作ら
れた合成紙を使用することもできる。
更に、転写記録後転写記録面に例えばポリエス
テルフイルムを熱プレスしラミネートすることに
より色素の発色の改良及び記録の保存安定化を計
ることができる。
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
で表わされるマゼンタ色色素および下記構造色式
で示されるシアン色色素と組み合せてフルカラー
を得るのに適している。
上記のマゼンタ色色素は、Ｎ−エチル−Ｎ−
（β−フエニルエチル）アニリンにテトラシアノ
エチレンを作用させることにより得られる。ま
た、上記のシアン色色素は１−アミノ−２−カル
ボキシ−４−メチルアミノアントラキノンを濃硫
酸中でメタノールを作用させることにより製造す
ることができる。
以下実施例によりこの発明を具体的に説明するが
本実施例は本願発明を限定するものではない。
実施例 １
感熱転写記録用インキの製造方法
上記色素 2g
エチルセルロース 8g
イソプロパノール 90g
計 100g
上記組成の色素混合物を、ガラスビーズを使用
するペイントコンデイシヨナーで約30分間混合処
理することにより該インキを調製した。
転写シートの作成方法
グラビア校正機（版深30μm）を用い上記イン
キをコンデンサー紙（10μm）に塗布した。
受像紙の作成方法
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）10g
と重炭酸カルシウム（丸尾カルシウム製造、スー
パー1500）50重量％の水スラリー50gを混合し、
調製した塗料を上質紙（厚さ200μm）にバーコー
ター（RK Print−Coat Instruments社製造、No.
５）を用いて塗布した。
転写記録方法
上記転写シートのインキ塗布面を上記受像紙の
塗料塗布面に重ね、250Ωの発熱抵抗体を４ドツ
ト／mmの密度で持つ感熱ヘツドを使用し、熱転写
記録を行ない、色濃度1.20のイエロー色の記録を
得た。この時感熱ヘツドには18Vの電圧が６ミリ
秒加えられた。
なお、色濃度は米国マクベス社製テンシトメー
ターRD−514型（フイルター：ラツテンNo.47）
を用いて測定した。
色濃度は下記色により計算した。
色濃度＝log10（I0／Ｉ）
I0：標準白色反射板からの反射光の強さ
Ｉ：試験物体からの反射光の強さ
また、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時間の照射でほとんど変色しなかつた。
実施例 ２
第１表に示す色素2gを使用し、実施例１と同
様の方法により、インキの調製、転写シート及び
受像紙の作成、転写記録を行ない、各々第１表に
示す色濃度のイエロー色の記録を得た。
これらの記録は全て実施例１と同様の方法によ
り耐光性の試験を行つたが該試験では、本発明色
素により得られた記録は、ほとんど変色しなかつ
た。[Formula] represents the same meaning as in the above general formula []) In addition to the azo dye represented by the following general formula [] R-X ... [] (wherein, R is the same as in the above general formula []) and X represents a halogen atom) or the following general formula [] (wherein R represents the same meaning as in the above general formula []) can be easily obtained by reacting with an alkylating agent. As a method for producing a thermal transfer recording ink using the dye of the present invention, the dye may be mixed with a suitable resin, solvent, water, etc. to prepare the recording ink. In the thermal transfer method, the ink obtained above is applied onto a suitable base material to create a transfer sheet, the sheet is placed on the recording medium, and then heated and pressed from the back side of the sheet using a thermal recording head. In this way, the dye on the sheet is transferred onto the recording medium. As the resin for preparing the above ink,
Those used in ordinary printing inks may be used, such as oil-based resins such as rosin-based, phenol-based, xylene-based, petroleum-based, vinyl-based, polyamide-based, alkyd-based, nitrocellulose-based, alkyl cellulose, or maleic resins. Acid-based,
Water-based resins such as acrylic acid, casein, Sierra, and glue can be used. In addition, as a solvent for ink preparation, methanol, ethanol,
Alcohols such as propanol and butanol, cellosolves such as methyl cellosolve and ethyl cellosolve, aromatics such as benzene, toluene and xylene, esters such as ethyl acetate and butyl acetate, ketones such as acetone, methyl ethyl ketone and cyclohexanone, ligroin , hydrocarbons such as cyclohexane and kerosene, dimethylformamide, etc. can be used, but when using an aqueous resin, water or a mixture of water and the above-mentioned solvents can also be used. Substrates for applying ink include capacitor paper, thin paper such as glassine paper, polyester,
A plastic film having good heat resistance such as polyamide or polyimide is suitable, and the thickness of these substrates is suitably about 5 to 50 .mu.m in order to improve the efficiency of heat transfer from the heat-sensitive recording head to the dye. Plain paper can also be used as the recording medium, but in order to improve the color development of the dye, it may be coated or impregnated with a resin that is compatible with the dye, or it may be laminated with a resin film. Good recording can be achieved by using paper or special processed paper that has been treated with acetylation.
It is also possible to use films of various resins or synthetic papers made from them. Furthermore, by hot-pressing and laminating, for example, a polyester film on the transfer recording surface after transfer recording, it is possible to improve the color development of the dye and to stabilize the recording during storage. Since the dye of the present invention has a vivid yellow color,
For example, the following structural formula The magenta color pigment represented by and the structural color formula below Suitable for obtaining full color in combination with cyan dyes shown in The above magenta color dye is N-ethyl-N-
It is obtained by reacting (β-phenylethyl)aniline with tetracyanoethylene. Further, the above cyan dye can be produced by reacting 1-amino-2-carboxy-4-methylaminoanthraquinone with methanol in concentrated sulfuric acid. 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 Method for producing thermal transfer recording ink The ink was prepared by mixing the pigment mixture having the above composition for about 30 minutes with a paint conditioner using glass beads. Method for creating a transfer sheet The above ink was applied to condenser paper (10 μm) using a gravure proofing machine (plate depth 30 μm). Method for making receiver paper: 10 g of an aqueous dispersion of 34% by weight saturated polyester (manufactured by Toyobo Co., Ltd., Vylonal MD-1200)
and 50 g of calcium bicarbonate (Maruo Calcium Manufacturing, Super 1500) 50% by weight water slurry,
Apply the prepared paint to high-quality paper (thickness 200 μm) using a bar coater (manufactured by RK Print-Coat Instruments, No.
5). Transfer recording method The ink-coated surface of the transfer sheet was placed on the paint-coated surface of the image-receiving paper, and thermal transfer recording was performed using a thermal head having a 250Ω heating resistor at a density of 4 dots/mm. A yellow record was obtained. At this time, a voltage of 18V was applied to the heat-sensitive head for 6 milliseconds. The color density was measured using a tensitometer RD-514 model manufactured by Macbeth Co., Ltd. (filter: Ratten No. 47).
Measured using Color density was calculated using the following colors. Color density = log 10 (I 0 /I) I 0 : Intensity of reflected light from the standard white reflector I : Intensity of reflected light from the test object In addition, the light resistance test of the obtained record was performed using a carbon arc film. Conducted using an ademeter (manufactured by Suga Test Instruments Co., Ltd.) (black panel temperature 63±2℃).
There was almost no discoloration after 40 hours of irradiation. Example 2 Using 2 g of the dye shown in Table 1, ink was prepared, a transfer sheet and image receiving paper were prepared, and transfer recording was performed in the same manner as in Example 1, and yellow with the color density shown in Table 1 was obtained. Obtained a color record. All of these records were tested for light resistance in the same manner as in Example 1, and in this test, the records obtained using the dye of the present invention showed almost no discoloration.
【表】【table】
【表】【table】
Claims (1)
基もしくはハロゲン原子で置換されていてもよい
フエニル基を表わし、Ｒは低級アルキル基、低級
アルコキシアルキル基、アリル基又は水素原子を
表わす）で示されるビリドンアゾ系感熱転写記録
用色素。[Claims] 1. General formula [] (In the formula, [Formula] represents a lower alkyl group, a lower alkoxy group, a trifluoromethyl group, a nitro group, or a phenyl group optionally substituted with a halogen atom, and R represents a lower alkyl group, a lower alkoxyalkyl group, an allyl group. (representing a group or a hydrogen atom) A biridone azo-based thermal transfer recording dye.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58137020A JPS6027594A (en) | 1983-07-27 | 1983-07-27 | Pyridone azo dye for thermal transfer recording |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58137020A JPS6027594A (en) | 1983-07-27 | 1983-07-27 | Pyridone azo dye for thermal transfer recording |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6027594A JPS6027594A (en) | 1985-02-12 |
| JPH0447635B2 true JPH0447635B2 (en) | 1992-08-04 |
Family
ID=15188953
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58137020A Granted JPS6027594A (en) | 1983-07-27 | 1983-07-27 | Pyridone azo dye for thermal transfer recording |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6027594A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1903078A2 (en) | 2006-06-29 | 2008-03-26 | FUJIFILM Corporation | Azo dye, heat-sensitive transfer recording ink sheet, heat-sensitive transfer recording method, color toner, inkjet ink and color filter |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5270285A (en) * | 1965-02-28 | 1993-12-14 | Dai Nippon Insatsu Kabushiki Kaisha | Sheet for heat transference |
| US4720480A (en) * | 1985-02-28 | 1988-01-19 | Dai Nippon Insatsu Kabushiki Kaisha | Sheet for heat transference |
| JPH0798426B2 (en) * | 1985-09-18 | 1995-10-25 | 大日本印刷株式会社 | Thermal transfer sheet |
| GB8612778D0 (en) * | 1986-05-27 | 1986-07-02 | Ici Plc | Thermal transfer printing |
| JPS6371392A (en) * | 1986-09-12 | 1988-03-31 | Matsushita Electric Ind Co Ltd | Transfer material for thermal transfer recording |
| EP0302627B1 (en) * | 1987-08-04 | 1993-06-02 | Imperial Chemical Industries Plc | Thermal transfer printing |
| JP2966849B2 (en) * | 1987-12-03 | 1999-10-25 | 三井化学株式会社 | Color material for yellow sublimation transfer |
| GB8906821D0 (en) * | 1989-03-23 | 1989-05-10 | Ici Plc | Thermal transfer printing |
| DE69106734T2 (en) * | 1990-02-14 | 1995-05-18 | Mitsubishi Chem Ind | Thermal transfer recording sheet and ink composition for producing the same. |
| US5041411A (en) * | 1990-12-14 | 1991-08-20 | Eastman Kodak Company | Yellow dye mixture for thermal color proofing |
| US5045524A (en) * | 1990-12-14 | 1991-09-03 | Eastman Kodak Company | Yellow dye mixture for thermal color proofing |
| US5041413A (en) * | 1990-12-14 | 1991-08-20 | Eastman Kodak Company | Yellow dye mixture for thermal color proofing |
| JP3004104B2 (en) * | 1991-11-01 | 2000-01-31 | コニカ株式会社 | Image recording method and image recording apparatus |
| EP0701907A1 (en) | 1994-09-13 | 1996-03-20 | Agfa-Gevaert N.V. | A dye donor element for use in a thermal dye transfer process |
| EP0733487B1 (en) | 1995-01-30 | 2000-05-24 | Agfa-Gevaert N.V. | Method for making a lithographic printing plate requiring no wet processing |
| EP0792757B1 (en) | 1996-02-27 | 2001-06-06 | Agfa-Gevaert N.V. | Dye donor element for use in thermal transfer printing |
| DE10028686A1 (en) * | 2000-06-09 | 2001-12-13 | Dystar Textilfarben Gmbh & Co | New hydroxypyridone methide azo dyes, useful in e.g. dyeing and printing hydrophobic fibers, ink-jet printing and color filters |
| TWI522426B (en) * | 2009-12-25 | 2016-02-21 | Sumitomo Chemical Co | Pyridone compounds |
-
1983
- 1983-07-27 JP JP58137020A patent/JPS6027594A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1903078A2 (en) | 2006-06-29 | 2008-03-26 | FUJIFILM Corporation | Azo dye, heat-sensitive transfer recording ink sheet, heat-sensitive transfer recording method, color toner, inkjet ink and color filter |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6027594A (en) | 1985-02-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0447635B2 (en) | ||
| JPH0578436B2 (en) | ||
| EP0247737A1 (en) | Thermal transfer printing | |
| JPH0447636B2 (en) | ||
| JPH0447637B2 (en) | ||
| JPH055677B2 (en) | ||
| JPH05235B2 (en) | ||
| JPS6031565A (en) | Monoazo dye for thermal transfer recording | |
| JPH0441078B2 (en) | ||
| JPH0513077B2 (en) | ||
| JPH0464880B2 (en) | ||
| JPH05233B2 (en) | ||
| JPH0461795B2 (en) | ||
| JPH0461797B2 (en) | ||
| JPH053398B2 (en) | ||
| JPS6339380A (en) | Thermal transfer sheet | |
| JPH0461794B2 (en) | ||
| JP2623241B2 (en) | Dye for thermal transfer recording and thermal transfer sheet | |
| JPH0466716B2 (en) | ||
| JPS6030393A (en) | Mono-azo coloring matter for thermal transfer recording | |
| JP3265063B2 (en) | Thermal transfer recording dye, thermal transfer recording ink composition and transfer sheet | |
| JPH05234B2 (en) | ||
| JPH0461796B2 (en) | ||
| JPS6030391A (en) | Naphthol coloring matter for thermal transfer recording | |
| JP2940943B2 (en) | Dye for thermal recording and transfer sheet |