GB726755A - Improvements in or relating to photographic diazotype materials - Google Patents
Improvements in or relating to photographic diazotype materialsInfo
- Publication number
- GB726755A GB726755A GB21183/53A GB2118353A GB726755A GB 726755 A GB726755 A GB 726755A GB 21183/53 A GB21183/53 A GB 21183/53A GB 2118353 A GB2118353 A GB 2118353A GB 726755 A GB726755 A GB 726755A
- Authority
- GB
- United Kingdom
- Prior art keywords
- diazo
- type
- compounds
- chlorobenzene
- rays
- 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
Links
- 239000000463 material Substances 0.000 title abstract 8
- 150000008049 diazo compounds Chemical class 0.000 abstract 24
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 abstract 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 5
- 150000003839 salts Chemical class 0.000 abstract 5
- 239000011592 zinc chloride Substances 0.000 abstract 4
- 235000005074 zinc chloride Nutrition 0.000 abstract 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 abstract 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 abstract 2
- 159000000000 sodium salts Chemical class 0.000 abstract 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 abstract 2
- DHJKHOVAFCEJMP-UHFFFAOYSA-N (4e)-2-chloro-4-diazo-n,n-diethylcyclohexa-1,5-dien-1-amine Chemical compound CCN(CC)C1=C(Cl)CC(=[N+]=[N-])C=C1 DHJKHOVAFCEJMP-UHFFFAOYSA-N 0.000 abstract 1
- YYZRXNIZXRJETP-UHFFFAOYSA-N (4e)-4-diazo-n-phenylcyclohexa-1,5-dien-1-amine Chemical compound C1=CC(=[N+]=[N-])CC=C1NC1=CC=CC=C1 YYZRXNIZXRJETP-UHFFFAOYSA-N 0.000 abstract 1
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 abstract 1
- IKQCSJBQLWJEPU-UHFFFAOYSA-N 2,5-dihydroxybenzenesulfonic acid Chemical compound OC1=CC=C(O)C(S(O)(=O)=O)=C1 IKQCSJBQLWJEPU-UHFFFAOYSA-N 0.000 abstract 1
- OFUXYBDYXIXULD-UHFFFAOYSA-N 2-chloro-4-diazo-N-ethylcyclohexa-1,5-dien-1-amine Chemical class [N+](=[N-])=C1CC(=C(C=C1)NCC)Cl OFUXYBDYXIXULD-UHFFFAOYSA-N 0.000 abstract 1
- YRYHSOVHYUPBHZ-UHFFFAOYSA-N 2-chloro-N-cyclohexyl-4-diazocyclohexa-1,5-dien-1-amine Chemical compound [N+](=[N-])=C1CC(=C(C=C1)NC1CCCCC1)Cl YRYHSOVHYUPBHZ-UHFFFAOYSA-N 0.000 abstract 1
- ZTFYJIXFKGPCHV-UHFFFAOYSA-N 2-propan-2-ylnaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(C(C)C)=CC=C21 ZTFYJIXFKGPCHV-UHFFFAOYSA-N 0.000 abstract 1
- AMEFXYVDFUUOMG-UHFFFAOYSA-N 4-diazo-N,N-diethyl-2-iodocyclohexa-1,5-dien-1-amine Chemical compound [N+](=[N-])=C1CC(=C(N(CC)CC)C=C1)I AMEFXYVDFUUOMG-UHFFFAOYSA-N 0.000 abstract 1
- XCKSVXOZXKLPGS-UHFFFAOYSA-N 4-diazo-N-ethyl-2-(trifluoromethyl)cyclohexa-1,5-dien-1-amine Chemical class [N+](=[N-])=C1CC(=C(C=C1)NCC)C(F)(F)F XCKSVXOZXKLPGS-UHFFFAOYSA-N 0.000 abstract 1
- FZLSTQYXGUDVAL-UHFFFAOYSA-N 4-diazo-n,n-diethyl-2-methylcyclohexa-1,5-dien-1-amine Chemical compound CCN(CC)C1=C(C)CC(=[N+]=[N-])C=C1 FZLSTQYXGUDVAL-UHFFFAOYSA-N 0.000 abstract 1
- YZYFPMLAGIGAJJ-UHFFFAOYSA-N 4-diazo-n,n-diethylcyclohexa-1,5-dien-1-amine Chemical compound CCN(CC)C1=CCC(=[N+]=[N-])C=C1 YZYFPMLAGIGAJJ-UHFFFAOYSA-N 0.000 abstract 1
- HVLAFPUUUISBRV-UHFFFAOYSA-N 4-diazo-n-ethyl-2-methylcyclohexa-1,5-dien-1-amine Chemical compound CCNC1=C(C)CC(=[N+]=[N-])C=C1 HVLAFPUUUISBRV-UHFFFAOYSA-N 0.000 abstract 1
- VKHOVLYIOYFOPD-UHFFFAOYSA-N 6-diazo-n,n-diethylcyclohexa-2,4-dien-1-amine Chemical compound CCN(CC)C1C=CC=CC1=[N+]=[N-] VKHOVLYIOYFOPD-UHFFFAOYSA-N 0.000 abstract 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 abstract 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 abstract 1
- PZWFZJVVWCXOFE-UHFFFAOYSA-N N,N-dibutyl-2-chloro-4-diazocyclohexa-1,5-dien-1-amine Chemical compound [N+](=[N-])=C1CC(=C(C=C1)N(CCCC)CCCC)Cl PZWFZJVVWCXOFE-UHFFFAOYSA-N 0.000 abstract 1
- ROGOAQTWKUPPPT-UHFFFAOYSA-N N-[5-diazo-2-(diethylamino)cyclohexa-1,3-dien-1-yl]benzamide Chemical compound [N+](=[N-])=C1CC(=C(C=C1)N(CC)CC)NC(C1=CC=CC=C1)=O ROGOAQTWKUPPPT-UHFFFAOYSA-N 0.000 abstract 1
- PWQSSKCMYLGPDP-UHFFFAOYSA-N N-benzyl-2-chloro-4-diazocyclohexa-1,5-dien-1-amine Chemical compound [N+](=[N-])=C1CC(=C(C=C1)NCC1=CC=CC=C1)Cl PWQSSKCMYLGPDP-UHFFFAOYSA-N 0.000 abstract 1
- GDCPABOBRZJPPK-UHFFFAOYSA-N N-cyclohexyl-4-diazo-2-(trifluoromethyl)cyclohexa-1,5-dien-1-amine Chemical compound [N+](=[N-])=C1CC(=C(C=C1)NC1CCCCC1)C(F)(F)F GDCPABOBRZJPPK-UHFFFAOYSA-N 0.000 abstract 1
- ODAIAUIHDNVGLV-UHFFFAOYSA-N O.O.O.O.O.[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[O-]B([O-])[O-].[O-]B([O-])[O-].[O-]B([O-])[O-].[O-]B([O-])[O-] Chemical compound O.O.O.O.O.[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[O-]B([O-])[O-].[O-]B([O-])[O-].[O-]B([O-])[O-].[O-]B([O-])[O-] ODAIAUIHDNVGLV-UHFFFAOYSA-N 0.000 abstract 1
- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 abstract 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical group [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- -1 alkyl radical Chemical class 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- 230000008033 biological extinction Effects 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000008878 coupling Effects 0.000 abstract 1
- 238000010168 coupling process Methods 0.000 abstract 1
- 238000005859 coupling reaction Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 229920000609 methyl cellulose Polymers 0.000 abstract 1
- 239000001923 methylcellulose Substances 0.000 abstract 1
- 235000010981 methylcellulose Nutrition 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 abstract 1
- 229960001553 phloroglucinol Drugs 0.000 abstract 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 abstract 1
- 230000001235 sensitizing effect Effects 0.000 abstract 1
- 239000000600 sorbitol Substances 0.000 abstract 1
- 239000010902 straw Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 239000010409 thin film Substances 0.000 abstract 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 abstract 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
- G03C1/54—Diazonium salts or diazo anhydrides
Landscapes
- 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)
Abstract
726,755. Photographic diazotype material. CHEMISCHE FABRIEK L. VAN DER GRINTEN N.V. July 30, 1953 [Aug. 13, 1952], No. 21183/53. Class 98 (2). One component diazotype material contains at least two different types (type I and II) of light-sensitive diazo compounds and has a total content of diazo compound of at least 0.3 millimol. diazo compound per m<SP>2</SP>. The novelty of this material consists in the following: it contains at least one diazo compound of type I of the following structure: wherein R 1 and R 2 represent an alkyl radical, X an anion and Y a substituent, which has, for rays of 4050 Š, an Epsilon value greater than 1.5 Î 10<SP>4</SP> and, for rays of 3650 Š, an Epsilon value lower than that for rays of 4050 Š; it contains at least one diazo compound of type II (described below) having, for rays of 3650 Š, an Epsilon value greater than 1.5 Î 10<SP>4</SP> and, for rays of 4050 ‰, an Epsilon value lower than for rays of 3650 Š, for rays of 4050 Š the Epsilon value of the diazo compound(s) of type I minus the Epsilon value of the diazo compound(s) of type II is at least 1.0 x 10<SP>4</SP>; for rays of 3650 Š the Epsilon value of the diazo compound(s) of type II minus the Epsilon value of the diazo compound(s) of type I is at least 1.0 Î 10<SP>4</SP>; the gamma value of the mixture of the diazo compounds of type I and II is less than that of material with the diazo compound(s) of type I or type II (whichever of these types has the lower gamma value) and the diazo compounds couple more rapidly than p-diazodiethyl-aniline. By " total content " of diazo compounds is to be understood the content of all the diazo compounds present in the diazotype material, i.e. the one or more diazo compounds of type I plus the one or more diazo compounds of type II, plus possibly other diazo compounds present in the diazo layer. The term " Epsilon " indicates the molar extinction coefficient, as measured in a layer of one centimetre thickness of an aqueous molar solution of the diazo compound. A method of determining the Epsilon values is described in the Specification. The diazo compounds of type II are not restricted to specific formulµ; but results of practical value are obtained with type II compounds of structure where R represents a cyclohexyl radical. The material is particularly valuable for copying from artistic tracings as of furniture or architectural subjects drawn in lead pencil and crayon, and may be used for copying from continuous tone dispositives. Semi-wet or thin film development with coupling components in the developer yields good prints. In example 1 the diazo compound of type I, the zinc chloride double salt of 1-diazo-4-diethylamino-3 chlorobenzene; and that of type II, the zinc chloride double salt of 1-diazo-4-monocyclohexylamino- 3-chlorobenzene, are separately dissolved in aqueous methyl cellulose solution containing the sodium salt of naphthalene-1: 3 : 6-trisulphonic acid and the solutions both separately and admixed are coated on to straw pulp paper, exposed under a neutral stopwedge, and developed by surface application of a solution containing potassium tetraborate pentahydrate, potassium hydroxide, thiourea, phloroglucinol, resorcinol, the potassium salt of hydroquinone monosulphonic acid, sorbitol and the sodium salt of isopropylnaphthalene sulphonic acid; to show gamma values of 2.3 and 2.4 respectively for papers treated with type I and type II solutions only, and the desirable gamma value of 1.9 for paper treated with an equal mixture of such solutions. In fourteen further examples the diazo compounds are, type I the zinc chloride double salts of 1-diazo-4-(N-methyl-N- cyclohexyl) amino-3-chlorobenzene, 1-diazo-4- diethylamino - 3 - iodo - benzene, 1 - diazo - 4 - diethylamino - 3 - benzoylamino benzene, 1 - diazo - 4 - diethylamino - 3 - methylbenzene, 1 - diazo - 4 - di - n - butylamino - 3 - chlorobenzene; 1 - diazo - diisobutylamino - 3 - sulphobenzene chloride and the stannic chloride double salt of 1-diazo-4-ethylethanolamino-3- chlorobenzene; and, type II, the zinc chloride double salts of 1-diazo-4-monoethylamino-3- trifluoromethyl benzene, 1-diazo-4-monoethylamino - 3 - chlorobenzene, 1 - diazo - 4 - mono - (4<SP>1</SP> - methylcyclohexyl) amino - 3 - chlorobenzene, 1 - diazo - 4 - monobenzylamino - 3 - chlorobenzene, 1 - diazo - 4 - monocyclohexylamino - 3 - trifluoromethylbenzene, 1 - diazo - 4 - monoethylamino - 3 - methylbenzene, 1 - diazo - 4 - ethyl - benzylaminobenzene, 1 - diazo - 4 - diethyl - amino - 2 - chlorobenzene. All examples provide full quantitative details of the sensitizing and developing solutions and Epsilon values of the diazo compounds used therein. More than one of either of the two types of diazo compounds may be used in the material, and the diazo mixture may include diazo compounds of neither of the two types, such as 1-diazo-2: 5- diethoxy - 4 - benzoylaminobenzene, 1 - diazo - 2 : 5 - dibenzyloxy - 4 - benzoylaminobenzene, 1 - diazo - 2: 5 - dibutoxy - 4 - acetylaminobenzene, 1 - diazo - 2 : 5 - diethoxy - 4 - ethylmercaptobenzene, 1 - diazo - 2 : 5 - diethoxy - 4 - (4<SP>1</SP> - ethoxyphenyl) benzene, 1 - diazo - 2 - diethylaminobenzene, 1 - diazo - 4 - phenylaminobenzene and 1-diazo-4-(4<SP>1</SP>-ethoxyphenylamino)- benzene.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL171784 | 1952-08-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB726755A true GB726755A (en) | 1955-03-23 |
Family
ID=19750576
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB21183/53A Expired GB726755A (en) | 1952-08-13 | 1953-07-30 | Improvements in or relating to photographic diazotype materials |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US2793118A (en) |
| BE (1) | BE521426A (en) |
| CH (1) | CH327756A (en) |
| DE (1) | DE1015679B (en) |
| FR (1) | FR1090494A (en) |
| GB (1) | GB726755A (en) |
| NL (2) | NL80603C (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4427500A (en) | 1982-03-15 | 1984-01-24 | American Hoechst Corporation | Method for producing an aluminum support useful for lithography |
| US4540648A (en) * | 1983-03-02 | 1985-09-10 | Hoechst Aktiengesellschaft | Two-component diazotype material with ultraviolet light-absorbing dye salt of a benzothiazole |
| US4581996A (en) * | 1982-03-15 | 1986-04-15 | American Hoechst Corporation | Aluminum support useful for lithography |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE543608A (en) * | 1954-12-15 | |||
| BE561008A (en) * | 1956-09-26 | |||
| US3450536A (en) * | 1961-03-24 | 1969-06-17 | Eg & G Inc | Silver halide photographic film having increased exposure-response characteristics |
| BE629466A (en) * | 1962-03-14 | |||
| SE335474B (en) * | 1963-04-18 | 1971-05-24 | R Landau | |
| NL299034A (en) * | 1963-10-09 | |||
| US3382070A (en) * | 1964-01-02 | 1968-05-07 | Gen Aniline & Film Corp | Black-line moist diazotype process |
| US3331690A (en) * | 1964-06-08 | 1967-07-18 | Ibm | Development of diazotype papers without a coupler |
| US3484241A (en) * | 1967-01-16 | 1969-12-16 | Ibm | Diazo type films with extended linear latitude |
| ZA6801453B (en) * | 1967-03-08 | |||
| US3622325A (en) * | 1968-03-07 | 1971-11-23 | Ricoh Kk | Diazotype photographic copying material adapted for wet development and for producing copied image in black color |
| JPS5280118A (en) * | 1975-12-26 | 1977-07-05 | Mitsubishi Paper Mills Ltd | Diazo photosensitive material for intermediates |
| JPS5297725A (en) * | 1976-02-13 | 1977-08-16 | Mitsubishi Paper Mills Ltd | Diazo photosensitive material for intermediates |
| US4148646A (en) * | 1977-06-13 | 1979-04-10 | Trans World Technology Laboratories, Inc. | Continuous tone diazotype process |
| US4224397A (en) * | 1979-01-26 | 1980-09-23 | Trans World Technology Laboratories Inc. (Twt Labs, Inc.) | Continuous tone diazo material |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1967371A (en) * | 1931-03-28 | 1934-07-24 | Kalle & Co Ag | Process of preparing copies |
| BE474743A (en) * | 1946-07-23 | |||
| US2532126A (en) * | 1946-12-16 | 1950-11-28 | Gen Aniline & Film Corp | Diazotype photographic material |
| GB644493A (en) * | 1948-01-09 | 1950-10-11 | Hall Harding Ltd | Improvements relating to the production of diazotype photo printing materials |
-
0
- NL NLAANVRAGE7710330,A patent/NL171784B/en unknown
- NL NL80603D patent/NL80603C/xx active
- BE BE521426D patent/BE521426A/xx unknown
-
1953
- 1953-07-29 US US371022A patent/US2793118A/en not_active Expired - Lifetime
- 1953-07-30 CH CH327756D patent/CH327756A/en unknown
- 1953-07-30 GB GB21183/53A patent/GB726755A/en not_active Expired
- 1953-08-01 DE DEC7988A patent/DE1015679B/en active Pending
- 1953-08-06 FR FR1090494D patent/FR1090494A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4427500A (en) | 1982-03-15 | 1984-01-24 | American Hoechst Corporation | Method for producing an aluminum support useful for lithography |
| US4581996A (en) * | 1982-03-15 | 1986-04-15 | American Hoechst Corporation | Aluminum support useful for lithography |
| US4540648A (en) * | 1983-03-02 | 1985-09-10 | Hoechst Aktiengesellschaft | Two-component diazotype material with ultraviolet light-absorbing dye salt of a benzothiazole |
| EP0118086A3 (en) * | 1983-03-02 | 1987-05-27 | Hoechst Aktiengesellschaft | Two-component diazo type material |
Also Published As
| Publication number | Publication date |
|---|---|
| NL171784B (en) | |
| US2793118A (en) | 1957-05-21 |
| BE521426A (en) | |
| FR1090494A (en) | 1955-03-30 |
| DE1015679B (en) | 1957-09-12 |
| NL80603C (en) | |
| CH327756A (en) | 1958-02-15 |
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