US3695885A - Heat developable diazotype copying material - Google Patents
Heat developable diazotype copying material Download PDFInfo
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- US3695885A US3695885A US43968A US3695885DA US3695885A US 3695885 A US3695885 A US 3695885A US 43968 A US43968 A US 43968A US 3695885D A US3695885D A US 3695885DA US 3695885 A US3695885 A US 3695885A
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- United States
- Prior art keywords
- copying material
- coupler
- group
- carbon atoms
- aqueous solution
- Prior art date
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- Expired - Lifetime
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- 239000000463 material Substances 0.000 title abstract description 76
- 150000001989 diazonium salts Chemical class 0.000 abstract description 31
- 239000000987 azo dye Substances 0.000 abstract description 8
- 238000006243 chemical reaction Methods 0.000 abstract description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 45
- 239000007864 aqueous solution Substances 0.000 description 40
- -1 alkyl radicals Chemical class 0.000 description 38
- 150000003254 radicals Chemical class 0.000 description 35
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 21
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 19
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 15
- 229930182490 saponin Natural products 0.000 description 15
- 150000007949 saponins Chemical class 0.000 description 15
- 238000005859 coupling reaction Methods 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 13
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 12
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 11
- 229910052739 hydrogen Inorganic materials 0.000 description 11
- 239000001257 hydrogen Substances 0.000 description 11
- 230000008878 coupling Effects 0.000 description 9
- 238000010168 coupling process Methods 0.000 description 9
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 6
- ZZTURJAZCMUWEP-UHFFFAOYSA-N diaminomethylideneazanium;hydrogen sulfate Chemical compound NC(N)=N.OS(O)(=O)=O ZZTURJAZCMUWEP-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- 229910052740 iodine Inorganic materials 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- 125000001874 trioxidanyl group Chemical group [*]OOO[H] 0.000 description 5
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 4
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 229960001948 caffeine Drugs 0.000 description 4
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 4
- FNAQSUUGMSOBHW-UHFFFAOYSA-H calcium citrate Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O FNAQSUUGMSOBHW-UHFFFAOYSA-H 0.000 description 4
- 239000001354 calcium citrate Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000004337 magnesium citrate Substances 0.000 description 4
- 229960005336 magnesium citrate Drugs 0.000 description 4
- 235000002538 magnesium citrate Nutrition 0.000 description 4
- HELHAJAZNSDZJO-OLXYHTOASA-L sodium L-tartrate Chemical compound [Na+].[Na+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O HELHAJAZNSDZJO-OLXYHTOASA-L 0.000 description 4
- 239000001509 sodium citrate Substances 0.000 description 4
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 4
- 239000001433 sodium tartrate Substances 0.000 description 4
- 229960002167 sodium tartrate Drugs 0.000 description 4
- 235000011004 sodium tartrates Nutrition 0.000 description 4
- 235000013337 tricalcium citrate Nutrition 0.000 description 4
- PLSARIKBYIPYPF-UHFFFAOYSA-H trimagnesium dicitrate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O PLSARIKBYIPYPF-UHFFFAOYSA-H 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 239000004227 calcium gluconate Substances 0.000 description 3
- 229960004494 calcium gluconate Drugs 0.000 description 3
- 235000013927 calcium gluconate Nutrition 0.000 description 3
- NEEHYRZPVYRGPP-UHFFFAOYSA-L calcium;2,3,4,5,6-pentahydroxyhexanoate Chemical compound [Ca+2].OCC(O)C(O)C(O)C(O)C([O-])=O.OCC(O)C(O)C(O)C(O)C([O-])=O NEEHYRZPVYRGPP-UHFFFAOYSA-L 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 239000011975 tartaric acid Substances 0.000 description 3
- 235000002906 tartaric acid Nutrition 0.000 description 3
- IBHWREHFNDMRPR-UHFFFAOYSA-N 2,4,6-Trihydroxybenzoic acid Chemical compound OC(=O)C1=C(O)C=C(O)C=C1O IBHWREHFNDMRPR-UHFFFAOYSA-N 0.000 description 2
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 2
- SQSPRWMERUQXNE-UHFFFAOYSA-N Guanylurea Chemical compound NC(=N)NC(N)=O SQSPRWMERUQXNE-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229960004256 calcium citrate Drugs 0.000 description 2
- JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 description 2
- 229960001790 sodium citrate Drugs 0.000 description 2
- 235000011083 sodium citrates Nutrition 0.000 description 2
- KKFDJZZADQONDE-UHFFFAOYSA-N (hydridonitrato)hydroxidocarbon(.) Chemical compound O[C]=N KKFDJZZADQONDE-UHFFFAOYSA-N 0.000 description 1
- AKEUNCKRJATALU-UHFFFAOYSA-N 2,6-dihydroxybenzoic acid Chemical compound OC(=O)C1=C(O)C=CC=C1O AKEUNCKRJATALU-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical group NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 235000005459 Digitaria exilis Nutrition 0.000 description 1
- 240000008570 Digitaria exilis Species 0.000 description 1
- 235000010575 Pueraria lobata Nutrition 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 230000003113 alkalizing effect Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- GUPPESBEIQALOS-UHFFFAOYSA-L calcium tartrate Chemical compound [Ca+2].[O-]C(=O)C(O)C(O)C([O-])=O GUPPESBEIQALOS-UHFFFAOYSA-L 0.000 description 1
- 239000001427 calcium tartrate Substances 0.000 description 1
- 235000011035 calcium tartrate Nutrition 0.000 description 1
- GUPPESBEIQALOS-ZVGUSBNCSA-L calcium;(2r,3r)-2,3-dihydroxybutanedioate Chemical compound [Ca+2].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O GUPPESBEIQALOS-ZVGUSBNCSA-L 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 201000008675 chorea-acanthocytosis Diseases 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-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
- G03C1/58—Coupling substances therefor
- G03C1/585—Precursors
Definitions
- a heat developable diazotype copying material comprising a support and a light-sensitive layer formed onto one surface of said support, said layer containing a coupler which activated during the heat development of the copying material and at least two kinds of diazonium compounds forming a black azo dye as a result of a reaction between said coupler and said idazonium compounds.
- the present invention relates to a diazotype copying material capable of forming a desired black copied-image through heat development.
- the conventional heat developable diazotype copying materials may be divided broadly into three categories as follows by the components of the light-sensitive layer thereof and the pattern of the heat development process applicable thereto.
- the object of the present invention is to provide a heat developable diazotype copying material of the foregoing category (c), and particularly materials which are capable of effecting the coupling of a copied image in black color tone.
- the coupler constituting one component of the lightsensitive layer applicable in the present invention includes such compounds as expressed by the following general formula:
- R and R each is a radical selected from the group consisting of hydrogen, alkyl radicals having 1 to 6 carbon atoms, benzyl, bromine, chlorine, iodine, acetyl, and w-carboxyalkyl radicals having 1 to 4 carbon atoms; and R is a radical selected from the group consisting of hydrogen, hydroxyl radical alkyl radical having 1 to 2 carbon atoms, alkyl-sulfonyloxy (--0--SO -alkyl) radicals in which the alkyl group has 1 to 4 carbon atoms, carboalkoxyoxy radicals in which the alkyl group has 1 to 4 carbon atoms, acylacyoxy o (-OO-acyl)t radicals having 7 to 9 carbon atoms, alkylacyloxy radicals having 2 to 12 carbon atoms, w-hydroxyalkyl radicals having 1 to 3 carbon atoms, w-hydroxyalkyloxy radicals having 1 to 3 carbon atoms and alkoxy
- R is a radical selected from the group consisting of hydrogen, hydroxyl radical, alkyl radicals having 1 to 2 carbon atoms, alkoxyl radicals having 1 to 4 carbon atoms, sulfonyloxy (-O-SO radical, alky1-sulfonyloxy (OSO -alky1) radical in which the alkyl group has 1 to 4 carbon atoms, carbamoyl radical, carbamoyloxy radical, carboalkoxyloxy radicals in which the alkoxyl group has 1 to 4 carbon atoms, acyloxyl radicals in which the acyl group has 2 to 9 carbon atoms, alkyl-acyloxyl radicals having 2 to 12 carbon atoms, w-hydroxyalkyl radicals having 1 to 3 carbon atoms and w-hydroxyalkyloxy radicals having 1 to 3 carbon atoms.
- C O O H Y is a member selected from the group consisting of wherein:
- R represents a radical selected from the group consisting of hydrogen, alkyl radicals having 1 to 4 carbon atoms, hydroxyethyl radical, hydroxypropyl radical and acetyl radical
- X is a member selected from the group consisting of Cl-' /2ZnCl wherein:
- R" is a radical selected from the group consisting of hydrogen, cyclohexyl radical, alkyl radicals having 1 to 4 carbon atoms, hydroxyalkyl radicals having 2 to 4 carbon atoms, cyano radical and aralkyl radicals hav- 5 ing 7 to 11 carbon atoms, such as R' is a radical selected from the group consisting of alkyl radicals having 1 to 4 carbon atoms, aralkyl radicals having 7 to 11 carbon atoms, such as cyclohexyl radical, hydroxyalkyl radicals having 2 to 4 carbon atoms and benzoyl radical; and X is the radical identical with that of said X expressed in the general Formula I.
- R" and R""' each is a radical selected from the group consisting of alkyl radicals having 1 to 4 carbon atoms, hydroxylalkyl radical having 2 to 3 carbon atoms and benzyl radical;
- X is the radical identical with that of X expressed in the general Formula I.
- X" and Y are the radicals identical with that of X and Y, respectively, expressed in the general Formula I;
- R and R each is a radical selected from the group consisting of alkoxyl radicals having 1 to 4 carbon atoms, halogens and hydrogen.
- Diazonium compounds of benzoyl amide group expressed by the following general Formula 1V:
- R and R each is a radical selected from the group consisting of alkoxyl radicals having 1 to 4 carbon atoms, halogens and hydrogen;
- R is a radical selected from the group consisting of hydrogen and alkyl radicals having 1 to 3 carbon atoms; and X" is the radical identical with that of X expressed in the general Formula I.
- a coupler expressed by the above-mentioned general formula usually forms a purple azo dye or a blue azo dye as a result of a coupling reaction between said coupler and a diazonium compound generally employed for conventional diazotype copying materials, but in case where a coupling reaction is effected between said coupler and a member selected from the group consisting of diazonium compounds expressed by the foregoing general Formulas I and I along with a member selected from the group consisting of diazonium compounds expressed by the foregoing general Formulas II, III or IV, there is formed a black azo dye. And, in case where a coupling reaction is effected between said coupler and a single member selected from the group consisting of diazonium compounds expressed by said general Formula I or general Formula I, there is formed a yellow azo dye.
- the present invention stems from the knowedge obtained through observation and study of the coupling reaction effected by means of varieties of combinations of diazonium compounds and coupler. At least one member as illustrated by Formulas I and I must be contained in the light-sensitive layer of the copying material. Diazonium compounds expressed by the general Formulas II through IV represent the optimum examples,
- any other diazonium compound generally employed in this field of art and capable of forming a blue azo dye or a purple azo dye as a result of coupling reaction between a coupler expressed by the foregoing general formula and said diazonium compound is also applicable in the present invention.
- an organic acid such as citric acid, tartaric acid, etc. as the acid component contributing to the preservability of the copying material
- thiourea contributing to the prevention of fading as well as the preservability of the copying material
- so-called coupling assistant such as guanidine sulfate, pentaerythritol, O- methyl-isothiourea, guanylurea, etc. contributing to accelerating the coupling
- guanidine sulfate pentaerythritol, O- methyl-isothiourea, guanylurea, etc. contributing to accelerating the coupling
- alkali metal or alkaline earth metal salt of an organic acid such as sodium citrate, calcium citrate, magnesium citrate, sodium tartrate, calcium tartarate, calcium gluconate, etc. may be employed as a assistant dissolving agent to accelerate dissolution of the foregoing coupler in preparing a solution for use in forming the light-sensitive layer.
- the intended copying material By applying an aqueous solution comprising the above mentioned components dissolved therein onto one surface of a support such as paper, an acetate film, a polyester film, a synthetic paper, etc. and drying thereafter, the intended copying material can be obtained.
- the thus obtained heat developable diazotype copying material of the present invention is characterized not only by the production of a distinct black-color image when employed for actual copying but also by the fact that the light-sensitive layer has a satisfactory heat-resisting property.
- the decomposition temperatures of diazonium compounds expressed by the general Formula I or I' are comparatively higher than those of conventional diazonium compounds and are in the range of from 150 to 200 C.
- the decomposition loss of the diazonium compound at the time of heat development is relatively small and a highly concentrated color development can be obtained. That is, since the copying material of the present invention employs a specifically selected diazonium compound as set forth above, even if the coupling is effected at a temperature in the range of from 150 to 200 (3., there will occur no loss of the diazonium compound due to heating, and a highly concentrated color development can be expected. Moreover, the copied image formed by the copying material of the present invention, that is, the dye produced thereby has excellent interceptive property for ultarviolet rays.
- n N -morgmon An aqueous solution comprising the foregoing components was applied onto the surface of a support consisting of paper precoated with silica, starch, polyvinyl acetate emulsion, etc. and dried at. a temperature in the range of from 100 to C. After superposing the original thereon, the thus treated support was exposed by means of a mercury lamp or a fluorescent lamp in conventional method and subsequently developed by heating at 170 Crfor 5 seconds. As a result, there was obtained a distince yellow-color image formed on a white background.
- COMPARATIVE EXAMPLE 3 The below-mentioned aqueous solution (A) and aqueous solution (B) were respectively treated in the same manner as in Comparative Example 1, and subsequently by treating the resultant two kinds of copying materials in the same way as in Comparative Example 1, heat development was effected. As a result, there was obtained a yellow-color image formed on a White background in both cases.
- Aqueous solution (A) Aqueous solution (8) Components:
- EXAMPLE 3 Aqueous solution (a) 1 Formula C O O H 9 Formula Subsequent to applying the foregoing aqueous solution (a) onto a support consisting of paper pre-coated in the same manner as in Comparative Example 1, and drying, the coated surface was further coated with the foregoing aqueous solution (b) and dried again, whereby a heat developable diazotype copying material was prepared. The image-forming property and the color of image of this copying material proved equal to that of Example 1. In those cases where the coupler employed for the foregoing aqueous solution (a) was replaced by a member selected from the below-mentioned Group-B of couplers, the effect was the same as in the present example.
- Aqueous solution (b) Components:
- Aqueous solution (b) Components:
- Aqueous solution (b) Components:
- the total molar quantity of diazonium compounds in the compositions of this invention is normally from about 0.2 to 1, based on the molar quantity of coupling compound, and the ratio of blue or purple color-producing diazonium compound to yellow color-producing diazonium compound is in the range of from about 0.2 to 2.0 mols per 1 mol of yellow color-producing diazonium compound.
- a black line heat developable diazotype copying material comprising a support and a light-sensitive layer formed onto one surface of said support wherein said layer contains:
- Coupler As the only coupler present a coupler selected from the group consisting of compounds having the general formula radicals in which the alkyl group has 1 to 4 carbon atoms, arylacyoxy radicals having 7 to 9 carbon atoms, lalkylacyloxy radicals having 2 to 12 carbon atoms, w-hydroxylalkyl radicals having 1 to 3 carbon atoms,
- R" is a radical selected from the group consisting of hydrogen, cyclohexyl radical, alkyl radicals having 1 to 4 carbon atoms, hydroxyalkyl radicals having 2 to 4 carbon atoms, cyano radical and aralkyl radicals having 7 to 11 carbon atoms;
- R' is a radical selected from the group consisting of alkyl radicals having 1 to 4 carbon atoms, aralkyl radicals having 7' to 11 carbon atoms, cyclohexyl radical, hydroxyalkyl radicals having 2 to 4 carbon atoms and benzoyl radical; and
- X is the radical identical with that of said X expressed in the general Formula I;
- X" is the radical identical with that of said X expressed in the general Formula I; and general Formula III V1! wherein R and R each is a radical selected from the 15 group consisting of alkoxyl radicals having 1 to 4 carbon atoms, halogens and hydrogen; R is a radical selected from the group consisting of hydrogen and alkyl radicals having 1 to 3 carbon atoms; and X' is the radical identical with that of said X expressed in the general Formula I.
- a diazotype copying material according to claim 1, wherein said light-sensitive layer further contains an organic acid, thiourea and a member selected from the group consisting of guanidine sulfate, pentaerythritol, O-methyl-isothiourea and guanylurea.
- a diazotype copying material according to claim 1, wherein said light-sensitive layer further contains a small amount of a salt selected from the group consisting of sodium citrate, calcium citrate, magnesium citrate, sodium tartrate, calcium tartrate and calcium gluconate.
- a heat developable diazotype copying material of claim 1 wherein the coupler is a compound of the group C OOH COOH HO- OH HO- OH Br- -C2H Ol- (CHz)3CH3 C O OH O OH C O OH 5.
- a heat developable diazotype copying material of claim 1 wherein the coupler is HO OH Br- C2 5 6.
- a heat developable diazotype copying material of claim 1 wherein the coupler is COOH HO OH C1- (CH2)aCHa 7.
- a heat developable diazotype copying material of claim 1 wherein the coupler is COOH HO OH 8.
- a heat developable diazotype copying material of claim 1 wherein the coupler is COOH HO OH 9.
- a heat developable diazotype copying material of claim 1 wherein the coupler is COOH HO- OH 10.
- a heat developable diazotype copying material of claim 1 wherein the coupler is HO OH CHQCHQCOOH 12.
- a heat developable diazotype copying material of claim 1 wherein the coupler is a compound of the group coon coon coon no on no on no on I I Br Cl CH:
- a heat developable diazotype copying material of claim 1 wherein the coupler is coon 00011 no or: no 011 I Br arm 01 Br 5 17.
- a heat developable diazotype copying material of claim 1 wherein the coupler is COOH COOH
- a heat developable diazotype copying material of claim 1 wherein the coupler is OOOH HO- OH Cl Br 22.
- a heat developable diazotype copying material of claim 1 wherein the coupler is a compound of the group C O OH ('30 OH O O OH HO OH HO OH HO- OH I 9 Br Br 01- (J1 Br Br CH: 47H: H;
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4474569 | 1969-06-07 | ||
| JP1747570A JPS4917291B1 (enExample) | 1970-02-28 | 1970-02-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3695885A true US3695885A (en) | 1972-10-03 |
Family
ID=26353997
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US43968A Expired - Lifetime US3695885A (en) | 1969-06-07 | 1970-06-05 | Heat developable diazotype copying material |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3695885A (enExample) |
| DE (1) | DE2018908C3 (enExample) |
| FR (1) | FR2056231A5 (enExample) |
| GB (1) | GB1307314A (enExample) |
| NL (1) | NL7006018A (enExample) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4252884A (en) * | 1979-08-14 | 1981-02-24 | James River Graphics, Inc. | Negative-working diazotype photoreproduction |
| US4289839A (en) * | 1976-10-22 | 1981-09-15 | James River Graphics, Inc. | Negative image diazography formulation with acid labile coupler, diazonium compound and carboxylic acid anhydride |
| US4411979A (en) * | 1981-01-28 | 1983-10-25 | Ricoh Company, Ltd. | Diazo type thermosensitive recording material |
| US4421839A (en) * | 1979-08-03 | 1983-12-20 | Dai Nippon Printing Co., Ltd. | Heat-sensitive and photofixing recording sheet with diazosulfonate and acidic coupling agent therefore |
| US4659644A (en) * | 1983-12-22 | 1987-04-21 | Ricoh Company, Ltd. | Diazo-type thermosensitive recording material with hydrazone coupler and chelating metal compound |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2495343B1 (fr) * | 1980-12-02 | 1987-02-20 | Regma | Materiaux diazotypes thermodeveloppables contenant un precurseur d'activateur liberant lors du chauffage une base forte. procede de diazotypie mettant en oeuvre ces materiaux |
-
1970
- 1970-04-16 GB GB1822670A patent/GB1307314A/en not_active Expired
- 1970-04-20 DE DE2018908A patent/DE2018908C3/de not_active Expired
- 1970-04-24 NL NL7006018A patent/NL7006018A/xx unknown
- 1970-06-02 FR FR7020228A patent/FR2056231A5/fr not_active Expired
- 1970-06-05 US US43968A patent/US3695885A/en not_active Expired - Lifetime
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4289839A (en) * | 1976-10-22 | 1981-09-15 | James River Graphics, Inc. | Negative image diazography formulation with acid labile coupler, diazonium compound and carboxylic acid anhydride |
| US4421839A (en) * | 1979-08-03 | 1983-12-20 | Dai Nippon Printing Co., Ltd. | Heat-sensitive and photofixing recording sheet with diazosulfonate and acidic coupling agent therefore |
| US4252884A (en) * | 1979-08-14 | 1981-02-24 | James River Graphics, Inc. | Negative-working diazotype photoreproduction |
| US4411979A (en) * | 1981-01-28 | 1983-10-25 | Ricoh Company, Ltd. | Diazo type thermosensitive recording material |
| US4659644A (en) * | 1983-12-22 | 1987-04-21 | Ricoh Company, Ltd. | Diazo-type thermosensitive recording material with hydrazone coupler and chelating metal compound |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2018908A1 (de) | 1970-12-17 |
| FR2056231A5 (enExample) | 1971-05-14 |
| NL7006018A (enExample) | 1970-12-09 |
| GB1307314A (en) | 1973-02-21 |
| DE2018908C3 (de) | 1975-10-16 |
| DE2018908B2 (de) | 1975-03-13 |
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