JPS62247352A - Black color developing diazo copying material - Google Patents
Black color developing diazo copying materialInfo
- Publication number
- JPS62247352A JPS62247352A JP8705986A JP8705986A JPS62247352A JP S62247352 A JPS62247352 A JP S62247352A JP 8705986 A JP8705986 A JP 8705986A JP 8705986 A JP8705986 A JP 8705986A JP S62247352 A JPS62247352 A JP S62247352A
- Authority
- JP
- Japan
- Prior art keywords
- coupling component
- naphthol
- diazo
- diazo copying
- copying material
- 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.)
- Granted
Links
- 239000000463 material Substances 0.000 title claims description 23
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 22
- 230000008878 coupling Effects 0.000 claims abstract description 25
- 238000010168 coupling process Methods 0.000 claims abstract description 25
- 238000005859 coupling reaction Methods 0.000 claims abstract description 25
- 150000008049 diazo compounds Chemical class 0.000 claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 7
- 238000004040 coloring Methods 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- GPXLWVUGESTLCA-UHFFFAOYSA-N 2-(tert-butylamino)naphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(NC(C)(C)C)=CC=C21 GPXLWVUGESTLCA-UHFFFAOYSA-N 0.000 abstract description 4
- MOXBCYIWIODTKI-UHFFFAOYSA-N 4-(dimethylamino)benzenediazonium Chemical compound CN(C)C1=CC=C([N+]#N)C=C1 MOXBCYIWIODTKI-UHFFFAOYSA-N 0.000 abstract description 3
- LKRFCQYWHSKAOG-UHFFFAOYSA-N 2-(butylamino)naphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(NCCCC)=CC=C21 LKRFCQYWHSKAOG-UHFFFAOYSA-N 0.000 abstract description 2
- RGCITEKHKXPDDH-UHFFFAOYSA-N 4-(diethylamino)benzenediazonium Chemical compound CCN(CC)C1=CC=C([N+]#N)C=C1 RGCITEKHKXPDDH-UHFFFAOYSA-N 0.000 abstract description 2
- JFGQHAHJWJBOPD-UHFFFAOYSA-N 3-hydroxy-n-phenylnaphthalene-2-carboxamide Chemical compound OC1=CC2=CC=CC=C2C=C1C(=O)NC1=CC=CC=C1 JFGQHAHJWJBOPD-UHFFFAOYSA-N 0.000 abstract 1
- 230000032683 aging Effects 0.000 abstract 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 12
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 8
- 229920002301 cellulose acetate Polymers 0.000 description 7
- 229920006267 polyester film Polymers 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 6
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 5
- WXHLLJAMBQLULT-UHFFFAOYSA-N 2-[[6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-yl]amino]-n-(2-methyl-6-sulfanylphenyl)-1,3-thiazole-5-carboxamide;hydrate Chemical compound O.C=1C(N2CCN(CCO)CC2)=NC(C)=NC=1NC(S1)=NC=C1C(=O)NC1=C(C)C=CC=C1S WXHLLJAMBQLULT-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- -1 hexyl-1-hydroxy-2-naphthylamide Chemical compound 0.000 description 5
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 230000005540 biological transmission Effects 0.000 description 4
- YKYOUMDCQGMQQO-UHFFFAOYSA-L cadmium dichloride Chemical compound Cl[Cd]Cl YKYOUMDCQGMQQO-UHFFFAOYSA-L 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- NJLLALPCADBTIS-UHFFFAOYSA-N 2,5-dibutoxy-4-morpholin-4-ylbenzenediazonium Chemical compound C1=C([N+]#N)C(OCCCC)=CC(N2CCOCC2)=C1OCCCC NJLLALPCADBTIS-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001739 density measurement Methods 0.000 description 3
- 230000006866 deterioration Effects 0.000 description 3
- 238000005562 fading Methods 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- 150000005207 1,3-dihydroxybenzenes Chemical class 0.000 description 2
- QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- GMICNERLJRJXAS-UHFFFAOYSA-N 4-morpholin-4-yl-2,5-di(propan-2-yloxy)benzenediazonium Chemical compound C1=C([N+]#N)C(OC(C)C)=CC(N2CCOCC2)=C1OC(C)C GMICNERLJRJXAS-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000000987 azo dye Substances 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- RRZFEOOHKQSQRS-UHFFFAOYSA-N 2-(dodecylamino)naphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(NCCCCCCCCCCCC)=CC=C21 RRZFEOOHKQSQRS-UHFFFAOYSA-N 0.000 description 1
- FUYYAJCEDZSWBQ-UHFFFAOYSA-N 2-[(4-methylphenyl)methylamino]benzenediazonium Chemical compound C1=CC(C)=CC=C1CNC1=CC=CC=C1[N+]#N FUYYAJCEDZSWBQ-UHFFFAOYSA-N 0.000 description 1
- MRYJADXDULIXCM-UHFFFAOYSA-N 2-morpholin-4-ylbenzenediazonium Chemical compound N#[N+]C1=CC=CC=C1N1CCOCC1 MRYJADXDULIXCM-UHFFFAOYSA-N 0.000 description 1
- RSLBWQMPUBDKQZ-UHFFFAOYSA-N 3-methoxy-4-pyrrolidin-1-ylbenzenediazonium Chemical compound COC1=CC([N+]#N)=CC=C1N1CCCC1 RSLBWQMPUBDKQZ-UHFFFAOYSA-N 0.000 description 1
- CVDKUNVLQOHHFZ-UHFFFAOYSA-N 4-(dibenzylamino)benzenediazonium Chemical compound C1=CC([N+]#N)=CC=C1N(CC=1C=CC=CC=1)CC1=CC=CC=C1 CVDKUNVLQOHHFZ-UHFFFAOYSA-N 0.000 description 1
- BOTGCZBEERTTDQ-UHFFFAOYSA-N 4-Methoxy-1-naphthol Chemical compound C1=CC=C2C(OC)=CC=C(O)C2=C1 BOTGCZBEERTTDQ-UHFFFAOYSA-N 0.000 description 1
- BIHDOXAXFMXYDF-UHFFFAOYSA-N 4-anilinobenzenediazonium Chemical compound C1=CC([N+]#N)=CC=C1NC1=CC=CC=C1 BIHDOXAXFMXYDF-UHFFFAOYSA-N 0.000 description 1
- XJNHUSFVTDWFFU-UHFFFAOYSA-N 7-thiabicyclo[4.1.0]hepta-2,4-diene-2,6-diol Chemical compound OC1=CC=CC2(O)SC12 XJNHUSFVTDWFFU-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- QCUOBSQYDGUHHT-UHFFFAOYSA-L cadmium sulfate Chemical compound [Cd+2].[O-]S([O-])(=O)=O QCUOBSQYDGUHHT-UHFFFAOYSA-L 0.000 description 1
- 229910000331 cadmium sulfate Inorganic materials 0.000 description 1
- 229960001948 caffeine Drugs 0.000 description 1
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide 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
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000006224 matting agent Substances 0.000 description 1
- 229910001507 metal halide Chemical class 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920006289 polycarbonate film Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229930182490 saponin Natural products 0.000 description 1
- 150000007949 saponins Chemical class 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/52—Compositions containing diazo compounds as photosensitive substances
- G03C1/61—Compositions containing diazo compounds as photosensitive substances with non-macromolecular additives
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/52—Compositions containing diazo compounds as photosensitive substances
- G03C1/58—Coupling substances therefor
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
Abstract
Description
【発明の詳細な説明】
（句産業上の利用
この発明は、ジアゾ複写材料に関するものである。より
詳細には、カップリング成分として特定の化合物を含む
ことによって、未現像及び現像処理済みフィルムの熱・
湿度及び光に対する安定性に優れ、経時による画像劣化
の少ない黒発色ジアゾ複写材料に関するものである。DETAILED DESCRIPTION OF THE INVENTION (Industrial Applications) This invention relates to diazo copying materials.More specifically, by including a specific compound as a coupling component, it is possible to use diazo copying materials for undeveloped and developed films. heat·
The present invention relates to a black-coloring diazo copying material that has excellent stability against humidity and light and exhibits little image deterioration over time.
（ロ）従来の技術
従来、黒色のジアゾ複写を得るためには、青色カップリ
ング成分と赤〜黄色カップリング成分を適切な比率で組
み合わせ、黒色となしている。この際青色カップリング
成分としてはナフトールＡｓ誘導体が、他方のカップリ
ング成分としては、フェノール誘導体、レゾルシン誘導
体、１−ナフトール、アセト酢酸アニリド等が知られて
いる。(b) Prior Art Conventionally, in order to obtain a black diazo copy, a blue coupling component and a red to yellow coupling component are combined in an appropriate ratio to produce black. In this case, naphthol As derivatives are known as the blue coupling component, and phenol derivatives, resorcinol derivatives, 1-naphthol, acetoacetanilide, etc. are known as the other coupling component.
青色カップリング成分のナフトールＡｓ誘導体は、未現
像及び現像処理済みフィルムの熱・湿度及び光に対する
安定性、経時による画像劣化等の諸性能を十分満足する
ものである。The naphthol As derivative as the blue coupling component sufficiently satisfies the various properties of undeveloped and developed films, such as stability against heat, humidity and light, and image deterioration over time.
他方のカップリング成分としては、耐光堅牢性に優れ、
現像速度の速いアセト酢酸アニリドが広く用いられてい
るが、未現像フィルムの経時安定性に問題がある。また
レゾルシン誘導体は、赤から茶色の発色しか得られず、
組み合わし得る青色カップリング成分が限られるうえ、
分子量が小さいため未現像フィルムの安定性及び耐光堅
牢性に問題がある。１−ナフトールを用いた場合、現像
速度は速いが、カップリング成分自体が昇華性のため、
未現像フィルムの安定性及び耐光堅牢性に問題があり、
その改良が望まれていた。The other coupling component has excellent light fastness,
Acetoacetic acid anilide, which has a fast development speed, is widely used, but there is a problem in the stability of undeveloped film over time. In addition, resorcinol derivatives can only produce a red to brown color,
The blue coupling components that can be combined are limited, and
Since the molecular weight is small, there are problems with the stability and light fastness of the undeveloped film. When using 1-naphthol, the development speed is fast, but since the coupling component itself is sublimable,
There are problems with the stability and light fastness of the undeveloped film,
Improvement was desired.
（ハ）発明が解決しようとする問題点
この発明はこの様な欠点を改良するためになされたもの
で、その目的はジアゾ化合物と青色カップリング成分及
び特定の化合物を組み合わせることにより、経時に於け
る濃度の低下を防止し、高画像品質を与える黒発色ジア
ゾ複写材料を提供することにある。(c) Problems to be solved by the invention This invention was made to improve these drawbacks, and its purpose is to combine a diazo compound, a blue coupling component, and a specific compound to solve the problem over time. It is an object of the present invention to provide a black coloring diazo copying material which prevents a decrease in image density and provides high image quality.
上記目的を達成する為に、ジアゾ複写材料に使用される
素材についても詳細な検討を行うことでこの発明に至っ
た。In order to achieve the above object, the present invention was achieved by conducting detailed studies on materials used in diazo copying materials.
（ニ）問題点を解決するための手段
この発明によれば、支持体上に、ジアゾ化合物と青色カ
ップリング成分及び一般式（１）：（式中Ｒは炭素数４
〜２０のアルキル基）で表される化合物の少なくとも１
種類を含むことを特徴とする黒発色ジアゾ複写材料が提
供される。(d) Means for Solving the Problems According to the present invention, a diazo compound, a blue coupling component and the general formula (1): (wherein R is 4 carbon atoms
-20 alkyl groups)
A black coloring diazo copying material is provided which is characterized in that it comprises a variety of black coloring diazo copying materials.
この発明で用いるカップリング成分としては、前記一般
式（Ｉ）で示されるものが使用される。この種類のカッ
プリング成分は、青色カップリング成分と組み合わせる
と良好な黒発色を示し、更にこの黒発色ジアゾ複写材料
は、経時による画像劣化が少なく、未現像及び現像処理
済みフィルムの熱・湿度及び光に対する安定性に優れて
いる。As the coupling component used in this invention, those represented by the above general formula (I) are used. This type of coupling component exhibits good black coloring when combined with a blue coupling component, and this black coloring diazo copying material exhibits little image deterioration over time and is resistant to heat and humidity on undeveloped and developed films. Excellent stability against light.
一般式（Ｉ）で示される化合物の具体例としては、ｎ−
ブチル−１−ヒドロキシ−２−ナフチルアミド、ｔｅｒ
ｔ−ブチル−１−ヒドロキシ−２−ナフチルアミド、ヘ
キシル−１−ヒドロキシ−２−ナフチルアミド、オクチ
ル−１−ヒドロキシ−２−ナフチルアミド、ドデシル−
１−ヒドロキシ−２−ナフチルアミド、ヘキサドデシル
−１−ヒドロキシ−２−ナフチルアミド、エイコサシル
−１−ヒドロキシ−２−ナフチルアミド等が挙げられる
。Specific examples of the compound represented by general formula (I) include n-
Butyl-1-hydroxy-2-naphthylamide, ter
t-Butyl-1-hydroxy-2-naphthylamide, hexyl-1-hydroxy-2-naphthylamide, octyl-1-hydroxy-2-naphthylamide, dodecyl-
Examples include 1-hydroxy-2-naphthylamide, hexadodecyl-1-hydroxy-2-naphthylamide, and eicosacil-1-hydroxy-2-naphthylamide.
この発明で用いられる青色カップリング成分は特に制約
されないが、一般にはナフトールＡｓ誘導体が望ましい
。例えば１−ヒドロキシ４メトキシナフタレン、１−ヒ
ドロキシナフトール４スルホン酸、２−ナフトール−３
−カルボン酸、２−ナフトール、３−カルボン酸−アニ
リド、２．ナフトール、３−カルボン酸−２′−メトキ
シアニリド、２−ナフトール−３−カルボン酸−２−エ
トキシアニリド、２−ナフトール−３−カルボン酸４′
−クロルアニリド、２−ナフトール−３−カルボン酸−
３’Ｎ−モルホリノ−プロピルアミド、２−ナフトール
−３−カルボン酸−エタノールアミド、２−ナフトール
−３−カルボン酸−ジェタノールアミド、２−ナフトー
ル−３−カルボン酸く−ナフトアニリド、２−ナフトー
ル−３−カルボン酸−〇−ナフトアニリド、２−ナフト
ール−３−カルボン酸−２−メチルアニリド、２−ナフ
トール−３−カルボン酸−３′−ニトロアニリド、２−
ナフトール−３−カルボン酸−２’、５’−ジメトキシ
アニリド等が挙げられる。The blue coupling component used in this invention is not particularly limited, but naphthol As derivatives are generally preferred. For example, 1-hydroxy4methoxynaphthalene, 1-hydroxynaphthol4sulfonic acid, 2-naphthol-3
-carboxylic acid, 2-naphthol, 3-carboxylic acid-anilide, 2. Naphthol, 3-carboxylic acid-2'-methoxyanilide, 2-naphthol-3-carboxylic acid-2-ethoxyanilide, 2-naphthol-3-carboxylic acid 4'
-Chloranilide, 2-naphthol-3-carboxylic acid-
3'N-morpholino-propylamide, 2-naphthol-3-carboxylic acid-ethanolamide, 2-naphthol-3-carboxylic acid-jetanolamide, 2-naphthol-3-carboxylic acid-naphthanilide, 2-naphthol- 3-carboxylic acid-〇-naphthanilide, 2-naphthol-3-carboxylic acid-2-methylanilide, 2-naphthol-3-carboxylic acid-3'-nitroanilide, 2-
Examples include naphthol-3-carboxylic acid-2',5'-dimethoxyanilide.
同じく、この発明で用いられるジアゾ化合物も、上記の
青色カップリング成分と組み合わせて青色発色するもの
であれば特に制約されない。例えば４−ジメチルアミノ
ベンゼンジアゾニウム、４−ジエチルアミノベンゼンジ
アゾニウム、４−ジイソプロピルアミノベンゼンジアゾ
ニウム、４−ジベンジルアミノベンゼンジアゾニウム、
４−メチルベンジルアミノベンゼンジアゾニウム、４−
モルホリノ−２，５−ジェトキシベンゼンジアゾニウム
、４−モルホリノ−２，５−ジイソプロポキシベンゼン
ジアゾニウム、４−モルホリノ−２，５−ジブトキシベ
ンゼンジアゾニウム、４−ピロリジノ−３−メトキシベ
ンゼンジアゾニウム、４−モルホリノベンゼンジアゾニ
ウム、４−アニリノベンゼンジアゾニウム、本トルイル
メルカプト−２，５−ジエトキシベンゼンジアゾニウム
などのジアゾ化合物の強酸塩（例えば硫酸、４フツカ化
ホウ素、６フツカ化リン酸など）や、またはこれらのジ
アゾ化合物と金属ハロゲン化物の複塩（例えば塩化亜鉛
、塩化錫、塩化カドミウムなど）が挙げられるが、勿論
これらに限定されるものでは無い。Similarly, the diazo compound used in the present invention is not particularly limited as long as it develops a blue color in combination with the above-mentioned blue coupling component. For example, 4-dimethylaminobenzenediazonium, 4-diethylaminobenzenediazonium, 4-diisopropylaminobenzenediazonium, 4-dibenzylaminobenzenediazonium,
4-methylbenzylaminobenzenediazonium, 4-
Morpholino-2,5-jethoxybenzenediazonium, 4-morpholino-2,5-diisopropoxybenzenediazonium, 4-morpholino-2,5-dibutoxybenzenediazonium, 4-pyrrolidino-3-methoxybenzenediazonium, 4- Strong acid salts of diazo compounds such as morpholinobenzenediazonium, 4-anilinobenzenediazonium, and toluylmercapto-2,5-diethoxybenzenediazonium (e.g., sulfuric acid, boron tetrafluoride, phosphoric acid hexafluoride, etc.), or these Examples include double salts of diazo compounds and metal halides (for example, zinc chloride, tin chloride, cadmium chloride, etc.), but are not limited to these, of course.
この発明に用いられる支持体は、一般に用いられるもの
で、例えばポリエステルフィルム、ポリエチレンフィル
ム、ポリカーボネイトフィルム、アセテートフィルム及
び紙などが挙げられる。The support used in this invention is commonly used, and includes, for example, polyester film, polyethylene film, polycarbonate film, acetate film, and paper.
この発明では、以上の素材の他に、通常のジアゾ複写材
に添加される各種材料、例えばプレカップリング防止剤
としてスルホサリチル酸・パラトルエンスルホン酸・硫
酸・塩酸・クエン酸などの各種のプロトン酸や、塩化亜
鉛・硫酸カドミウム・塩化カドミウム・３フツ化ホウ素
などのルイス酸が使用できる。また酸化防止剤として、
チオ尿素・尿素・アリールチオ尿素などが使用できる。In addition to the above-mentioned materials, this invention uses various materials added to ordinary diazo copying materials, such as various protonic acids such as sulfosalicylic acid, para-toluenesulfonic acid, sulfuric acid, hydrochloric acid, and citric acid as pre-coupling inhibitors. Lewis acids such as zinc chloride, cadmium sulfate, cadmium chloride, and boron trifluoride can be used. Also, as an antioxidant,
Thiourea, urea, arylthiourea, etc. can be used.
さらに分散剤としてサポニンなどが、溶解剤としてカフ
ェイン・テオフィリンなどが使用できる。バインダー樹
脂として澱粉・ガゼイン・ポリ酢酸ビニル・ポリアクリ
ル酸またはポリアクリル酸ソーダ・セルロース誘導体な
どのポリマーが使用できる。さらにつや消し剤としてシ
リカ微粉末を入れることも出来る。必要に応じてスチレ
ン系・塩化ビニリデン系などのアンダーコートを施して
もよい。Furthermore, saponin or the like can be used as a dispersing agent, and caffeine, theophylline, etc. can be used as a solubilizing agent. As the binder resin, polymers such as starch, casein, polyvinyl acetate, polyacrylic acid or sodium polyacrylate, and cellulose derivatives can be used. Furthermore, fine silica powder can be added as a matting agent. If necessary, a styrene-based, vinylidene chloride-based, etc. undercoat may be applied.
この発明のジアゾ複写材料を作成するには、上 −記成
分を水またはメチルエチルケトンなどの適当な溶剤に溶
解もしくは分散し、しかる後にポリエステル、酢酸セル
ロースフィルムや紙等の適当な支持体上に、この液を塗
布し乾燥する。この際、カップリング成分とジアゾ成分
のモル比は、１：０．１〜１０が望ましく、好ましくは
１：０．５〜３である。To prepare the diazo copying material of this invention, the above components are dissolved or dispersed in a suitable solvent such as water or methyl ethyl ketone, and then this is deposited on a suitable support such as polyester, cellulose acetate film or paper. Apply the liquid and let it dry. At this time, the molar ratio of the coupling component to the diazo component is desirably 1:0.1-10, preferably 1:0.5-3.
また青色カップリング成分と他方のカップリング成分の
モル比は、１：０．５〜１０が望ましく、好ましくは１
：１〜３である。The molar ratio of the blue coupling component to the other coupling component is desirably 1:0.5 to 10, preferably 1:0.5 to 10.
:1 to 3.
このようにして作成されたフィルム上に、アゾ染料画像
を発色させるには、一般のジアゾ複写材料と同様に、蛍
光灯や紫外線水銀灯を用いて画像を焼き付け、その後ア
ンモニアガスまたはアルカリ現像液を用いてアゾ染料画
像を形成させる。To develop an azo dye image on the film produced in this way, the image is printed using a fluorescent lamp or an ultraviolet mercury lamp, and then an ammonia gas or alkaline developer is used, as with general diazo copying materials. to form an azo dye image.
（ホ）作用
本発明の黒発色ジアゾ複写材料は前記構成であるため、
経時安定性、耐光堅牢性が改侍される。(E) Effect Since the black coloring diazo copying material of the present invention has the above-mentioned structure,
Improved stability over time and light fastness.
（へ）実施例 以下本発明を実施例により詳細に説明する。(f) Example The present invention will be explained in detail below using examples.
実施例１ 下記組成にて感光液を調製する。Example 1 A photosensitive solution is prepared with the following composition.
メチルエチルケトン ４０．０ｇメチ
ルセロソルブ ４０．０ｇ酢酸セル
ロース １５．０ｇシリカ微粉
末 １．０ｇスルホサリチル酸
１．５ｇ４−モルホリノ−２，
５−ジブトキシベンゼンジアゾニウム・ＢＦ４
２．０ｇ２−ナフトール−３−カルボン酸
一部−ナフチルアニリド ０．４ｇ
ｔｅｒｔ−ブチル−１−ヒドロキシ
−２−ナフチルアミド ２．５ｇ
上記感光液を、１０％モノクロル酢酸水溶液で表面処理
したポリエステルフィルム（厚味７５μ）上に、ワイヤ
ーバーを用いて塗布後、乾燥し厚味１０１１の感光層を
有する黒発色ジアゾ複写材料を得た。Methyl ethyl ketone 40.0g Methyl cellosolve 40.0g Cellulose acetate 15.0g Silica fine powder 1.0g Sulfosalicylic acid 1.5g 4-morpholino-2,
5-dibutoxybenzenediazonium・BF4
2.0g 2-naphthol-3-carboxylic acid part-naphthylanilide 0.4g
tert-butyl-1-hydroxy-2-naphthylamide 2.5g
The photosensitive solution was applied using a wire bar onto a polyester film (thickness: 75 μm) whose surface had been treated with a 10% monochloroacetic acid aqueous solution, and then dried to obtain a black coloring diazo copying material having a photosensitive layer with a thickness of 1011 mm. .
実施例２ 下記組成にて感光液を調製する。Example 2 A photosensitive solution is prepared with the following composition.
メチルエチルケトン ４０．０ｇメチ
ルセロソルブ ４０．０ｇ酢酸セル
ロース １５．０ｇスルホサリ
チル酸 １．５ｇ４−モルホリノ
−２，５−ジブトキシベンゼンジアゾニウム−ＰＦ５
２．２ｇ２−ヒドロキシナフタレ
ン−３−カルボン酸−〇−ナフチルアミド
０．８ｇｔｅｒｔ−ブチル−１−ヒドロキシ
−２−ナフチルアミド １．７ｇ
上記感光液を、１０％モノクロル酢酸水溶液で表面処理
したポリエステルフィルム（厚味７５ｐ）上ニ、ワイヤ
ーバーを用いて塗布後、乾燥し厚味１０μの感光層を有
する黒発色ジアゾ複写材料を得た。Methyl ethyl ketone 40.0g Methyl cellosolve 40.0g Cellulose acetate 15.0g Sulfosalicylic acid 1.5g 4-morpholino-2,5-dibutoxybenzenediazonium-PF5
2.2g 2-hydroxynaphthalene-3-carboxylic acid-〇-naphthylamide
0.8g tert-butyl-1-hydroxy-2-naphthylamide 1.7g
The above photosensitive solution was applied using a wire bar onto a polyester film (thickness: 75p) whose surface had been treated with a 10% monochloroacetic acid aqueous solution, and then dried to obtain a black coloring diazo copying material having a photosensitive layer with a thickness of 10μ. .
実施例３ 下記組成にて感光液を調製する。Example 3 A photosensitive solution is prepared with the following composition.
メチルエチルケトン ４０．０ｇメチ
ルセロソルブ ４０．０ｇ酢酸セル
ロース １５．０ｇパラトルエ
ンスルホン酸１．２ｇ
４−トルイルメルカプト−２，５−ジェトキシベンゼン
ジアゾニウム、ＰＦ（３２，３ｇ２−ナフトール−３−
カルボン酸
−２′−メトキシアニリド ０．６ｇ
トチ゛シルー１−ヒドロキシ
−２−ナフチルアミド ２．０ｇ
上記感光液を、１０％モノクロル酢酸水溶液で表面処理
したポリエステルフィルム（厚味７５１１）上に、ワイ
ヤーバーを用いて塗布後、乾燥し厚味１０１１の感光層
を有する黒発色ジアゾ複写材料を得た。Methyl ethyl ketone 40.0g Methyl cellosolve 40.0g Cellulose acetate 15.0g Para-toluenesulfonic acid 1.2g 4-Toluylmercapto-2,5-jethoxybenzenediazonium, PF (32,3g 2-naphthol-3-
Carboxylic acid-2'-methoxyanilide 0.6g
Tochisilyl 1-hydroxy-2-naphthylamide 2.0g
The above photosensitive solution was applied using a wire bar onto a polyester film (thickness: 7511) whose surface had been treated with a 10% monochloroacetic acid aqueous solution, and then dried to obtain a black colored diazo copying material having a photosensitive layer with a thickness of 1011. .
実施例４ 下記組成にて感光液を調製する。Example 4 A photosensitive solution is prepared with the following composition.
アセトン ４０．０ｇメチ
ルセロソルブアセテ−） ４０．０ｇセルロ
ースアセテートプチレー） １５．０ｇパラトル
エンスルホン酸 ０．５ｇ４−モルホリノ
−２，５−ジイソプロポキシベンゼンジアゾニウム・Ｐ
Ｆ（３１，８ｇ２−ナフトール−３−カルボン酸
−エタノールアミド ０．４ｇド
デシル−１−ヒドロキシ
−２−ナフチルアミド １．２ｇ
上記感光液を、１０％モノクロル酢酸水溶液で表面処理
したポリエステルフィルム（厚味７５１１）上に、ワイ
ヤーバーを用いて塗布後、乾燥し厚味１０１１の感光層
を有する黒発色ジアゾ複写材料を得た。Acetone 40.0g methyl cellosolve acetate) 40.0g cellulose acetate petite) 15.0g para-toluenesulfonic acid 0.5g 4-morpholino-2,5-diisopropoxybenzenediazonium.P
F (31,8g 2-naphthol-3-carboxylic acid-ethanolamide 0.4g dodecyl-1-hydroxy-2-naphthylamide 1.2g
The above photosensitive solution was applied using a wire bar onto a polyester film (thickness: 7511) whose surface had been treated with a 10% monochloroacetic acid aqueous solution, and then dried to obtain a black colored diazo copying material having a photosensitive layer with a thickness of 1011. .
比較例１ 下記組成にて感光液を調製する。Comparative example 1 A photosensitive solution is prepared with the following composition.
メチルエチルケトン ４０．０ｇメチ
ルセロソルブ ４０．０ｇ酢酸セル
ロース １５．０ｇスルホサリ
チル酸 １．４ｇ４−ジメチルア
ミノベンゼン
ジアゾニウムＢＦ４ ０．７ｇ２
−ナフトール−３−カルボン酸
−２−エトキシアニリド ０．９ｇジ
レゾルシノールスルフィド ０．３ｇ上記感
光液を、１０％モノクロル酢酸水溶液で表面処理したポ
リエステルフィルム（厚味７５１１）上に、ワイヤーバ
ーを用いて塗布後、乾燥し厚味１０１１の感光層を有す
る黒発色ジアゾ複写材料を得た。Methyl ethyl ketone 40.0g Methyl cellosolve 40.0g Cellulose acetate 15.0g Sulfosalicylic acid 1.4g 4-Dimethylaminobenzenediazonium BF4 0.7g2
- Naphthol-3-carboxylic acid-2-ethoxyanilide 0.9 g Diresorcinol sulfide 0.3 g The above photosensitive solution was placed on a polyester film (thickness 7511) whose surface had been treated with a 10% monochloroacetic acid aqueous solution using a wire bar. After coating, a black coloring diazo copying material having a photosensitive layer with a thickness of 1011 mm was obtained by drying.
比較例２ 下記組成にて感光液を調製する。Comparative example 2 A photosensitive solution is prepared with the following composition.
メチルエチルケトン ４０．０ｇメチ
ルセロソルブ ４０．０ｇ酢酸セル
ロース １５．０ｇスルホサリ
チル酸 １．４ｇ４−モルホリノ
−２，５−ジブトキシベンゼンジアゾニウム・ＢＦ４
２．０ｇ２−ナフトール−３−カル
ボン酸
−ジェタノールアミド ０．９ｇレ
ゾルシン ０．３ｇ上記感
光液を、１０％モノクロル酢酸水溶液で表面処理したポ
リエステルフィルム（厚味７５１１）上に、ワイヤーバ
ーを用いて塗布後、乾燥し厚味１ｏｌｌの感光層を有す
る黒発色ジアゾ複写材料を得た。Methyl ethyl ketone 40.0g Methyl cellosolve 40.0g Cellulose acetate 15.0g Sulfosalicylic acid 1.4g 4-morpholino-2,5-dibutoxybenzenediazonium BF4
2.0 g 2-naphthol-3-carboxylic acid-jetanolamide 0.9 g Resorcinol 0.3 g The above photosensitive solution was placed on a polyester film (thickness 7511) whose surface had been treated with a 10% monochloroacetic acid aqueous solution using a wire bar. After coating, it was dried to obtain a black coloring diazo copying material having a photosensitive layer with a thickness of 1 ol.
以上のように作成した試験フィルム実施例１〜４及び比
較例１・２について、下記の試験を行った。試験方法並
びにその結果を以下に示す。The following tests were conducted on the test films Examples 1 to 4 and Comparative Examples 1 and 2 prepared as described above. The test method and results are shown below.
１、耐熱・耐湿度試験
各試験片を６０°Ｃ・相対湿度９０％にて７２時間加熱
放置し、その後水銀灯により画像を焼き付け、アンモニ
ア現像機（ダイセル化学工業株式会社アクロス自動現像
機ＡＰ−２６Ｄ）で完全に発色させ、透過濃度計（マク
ベス透過濃度計ＴＤ−９０４．可視フィルター使用）で
、画像部及び非画像部の濃度を測定する。測定結果を次
に示す。1. Heat resistance/humidity resistance test Each test piece was heated at 60°C and relative humidity of 90% for 72 hours, and then the image was printed using a mercury lamp using an ammonia developing machine (Daicel Chemical Industries, Ltd. Across automatic developing machine AP-26D). ) to completely develop the color, and measure the density of the image area and non-image area using a transmission densitometer (Macbeth transmission densitometer TD-904, using a visible filter). The measurement results are shown below.
濃度測定結果
以上より明らかなように、比較例１・２とも画像部の退
色と非画像部の濃度上昇が観察されるのに対し、実施例
ではほとんど濃度の変化が無く、この発明の目的が達成
されているのが判る。As is clear from the density measurement results above, in Comparative Examples 1 and 2, fading of color in the image area and increase in density in the non-image area were observed, whereas in the example, there was almost no change in density, and the purpose of this invention was achieved. It appears that this has been achieved.
２、退色試験
各試験片を水銀灯により画像を焼き付け、アンモニア現
像機（ダイセル化学工業株式会社アクロス自動現像機Ａ
Ｐ−２６Ｄ）で完全に発色させ、透過濃度計（マクベス
透過濃度計ＴＤ−９０４．可視フィルター使用）で、画
像部及び非画像部の濃度を測定する。その後快晴の日を
選び、７日間日光暴露試験を行った。濃度測定結果を次
に示す。2. Fading test: Burn an image on each test piece using a mercury lamp, and use an ammonia developer (Daicel Chemical Industries, Ltd. Across automatic developer A).
P-26D) to completely develop the color, and measure the density of the image area and non-image area using a transmission densitometer (Macbeth transmission densitometer TD-904, using a visible filter). Thereafter, a sunny day was selected and a sunlight exposure test was conducted for 7 days. The concentration measurement results are shown below.
濃度測定結果
濃度測定結果より明らかなように、比較例１・２とも染
料の昇華または分解による画像部の退色が観察されるの
に対し、実施例では濃度の変化が少なく、この発明の目
的が達成されているのが判る。Density Measurement Results As is clear from the density measurement results, in both Comparative Examples 1 and 2, fading of color in the image area due to sublimation or decomposition of the dye was observed, whereas in the Examples, there was little change in density, and the purpose of the present invention was achieved. It appears that this has been achieved.
Claims (1)
一般式（ I ）： ▲数式、化学式、表等があります▼（ I ） （式中Ｒは炭素数４〜２０のアルキル基） で表される化合物の少なくとも１種類を含むことを特徴
とする黒発色ジアゾ複写材料。[Claims] On the support, there are a diazo compound, a blue coupling component, and the general formula (I): ▲Mathematical formula, chemical formula, table, etc.▼(I) (In the formula, R is an alkyl having 4 to 20 carbon atoms. A black coloring diazo copying material characterized by containing at least one compound represented by the following group.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8705986A JPS62247352A (en) | 1986-04-17 | 1986-04-17 | Black color developing diazo copying material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8705986A JPS62247352A (en) | 1986-04-17 | 1986-04-17 | Black color developing diazo copying material |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62247352A true JPS62247352A (en) | 1987-10-28 |
| JPH0549209B2 JPH0549209B2 (en) | 1993-07-23 |
Family
ID=13904366
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8705986A Granted JPS62247352A (en) | 1986-04-17 | 1986-04-17 | Black color developing diazo copying material |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62247352A (en) |
-
1986
- 1986-04-17 JP JP8705986A patent/JPS62247352A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0549209B2 (en) | 1993-07-23 |
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