US2350843A - Diazotype photographic material - Google Patents

Diazotype photographic material Download PDF

Info

Publication number: US2350843A
Authority: US; United States
Prior art keywords: light; diazotype; pyrrolidine; sensitive; solution
Prior art date: 1943-08-05
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

Application number

US497546A

Other languages

English (en)

Inventor

Vanselow Waldemar

Weissberger Arnold

Dudley B Glass

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Eastman Kodak Co

Original Assignee

Eastman Kodak Co

Priority date (The priority date 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 date listed.)

1943-08-05

Filing date

1943-08-05

Publication date

1944-06-06

Priority to FR955352D priority Critical patent/FR955352A/fr

1943-08-05 Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co

1943-08-05 Priority to US497546A priority patent/US2350843A/en

1944-06-06 Application granted granted Critical

1944-06-06 Publication of US2350843A publication Critical patent/US2350843A/en

1961-06-06 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000000463 material Substances 0.000 title description 11
150000001875 compounds Chemical class 0.000 description 13
239000000243 solution Substances 0.000 description 12
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 10
230000008878 coupling Effects 0.000 description 8
238000010168 coupling process Methods 0.000 description 8
238000005859 coupling reaction Methods 0.000 description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
238000000034 method Methods 0.000 description 5
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
150000008049 diazo compounds Chemical class 0.000 description 3
-1 methoxy, ethoxy, propoxy Chemical group 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
230000001235 sensitizing effect Effects 0.000 description 3
239000003381 stabilizer Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
VRJYOMHGXWVGNA-UHFFFAOYSA-N 2-methyl-4-pyrrolidin-1-ylaniline Chemical compound C1=C(N)C(C)=CC(N2CCCC2)=C1 VRJYOMHGXWVGNA-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
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 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
239000003513 alkali Substances 0.000 description 2
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
239000004327 boric acid Substances 0.000 description 2
239000011248 coating agent Substances 0.000 description 2
238000000576 coating method Methods 0.000 description 2
150000001989 diazonium salts Chemical class 0.000 description 2
239000000047 product Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
235000002906 tartaric acid Nutrition 0.000 description 2
239000011975 tartaric acid Substances 0.000 description 2
UPSPVRUBINSVBS-UHFFFAOYSA-N 1-(3-methyl-4-nitrophenyl)pyrrolidine Chemical compound C1=C([N+]([O-])=O)C(C)=CC(N2CCCC2)=C1 UPSPVRUBINSVBS-UHFFFAOYSA-N 0.000 description 1
RMQVXHUYDMSNIF-UHFFFAOYSA-N 1-phenylpyrrolidin-2-amine Chemical compound NC1CCCN1C1=CC=CC=C1 RMQVXHUYDMSNIF-UHFFFAOYSA-N 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
229920000623 Cellulose acetate phthalate Polymers 0.000 description 1
229920008347 Cellulose acetate propionate Polymers 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
108010010803 Gelatin Proteins 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
239000004372 Polyvinyl alcohol Substances 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000000987 azo dye Substances 0.000 description 1
239000002585 base Substances 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
230000001680 brushing effect Effects 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
HOPSCVCBEOCPJZ-UHFFFAOYSA-N carboxymethyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC(O)=O HOPSCVCBEOCPJZ-UHFFFAOYSA-N 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
HKQOBOMRSSHSTC-UHFFFAOYSA-N cellulose acetate Chemical compound OC1C(O)C(O)C(CO)OC1OC1C(CO)OC(O)C(O)C1O.CC(=O)OCC1OC(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(COC(C)=O)O1.CCC(=O)OCC1OC(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C1OC1C(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C(COC(=O)CC)O1 HKQOBOMRSSHSTC-UHFFFAOYSA-N 0.000 description 1
229920002301 cellulose acetate Polymers 0.000 description 1
229940081734 cellulose acetate phthalate Drugs 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000012954 diazonium Substances 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
238000007598 dipping method Methods 0.000 description 1
238000010410 dusting Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000004744 fabric Substances 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000011521 glass Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
230000006872 improvement Effects 0.000 description 1
238000011534 incubation Methods 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
229920001220 nitrocellulos Polymers 0.000 description 1
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000004627 regenerated cellulose Substances 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
238000005507 spraying Methods 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
ZLSOEGVSXYPCHL-UHFFFAOYSA-N sulfuric acid;tetrahydrate Chemical compound O.O.O.O.OS(O)(=O)=O ZLSOEGVSXYPCHL-UHFFFAOYSA-N 0.000 description 1
230000008719 thickening Effects 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

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

Definitions

This invention relates to diazotype photographic materials. More particularly, it relates to diazotype copying materials wherein the light-sensitive compound is a diazo derivative ofan aminophenyl pyrrolidine having the general formula:
R can also be substituted in one or more positions not occupied by the amino groups by monovalent s'ubstituents such as an alkyl group represented by methyl, ethyl, propyl, or butyl, for example, an alkon group represented by methoxy, ethoxy, propoxy, or butoiw, for example, a halogen, such as chlorine, bromine, or a sulphonic acid radical.
monovalent s'ubstituents such as an alkyl group represented by methyl, ethyl, propyl, or butyl, for example, an alkon group represented by methoxy, ethoxy, propoxy, or butoiw, for example, a halogen, such as chlorine, bromine, or a sulphonic acid radical.
diazo derivatives of the above described compounds are stable under all ordinary conditions, but decompose more or less completely on exposure to light. Since they are also capable of condensing with certain aromatic coupling components, as well as with their own decomposition products, in the presence of alkaline substances, to form fast azo dyes, we have found that'our diazovderivatives are excellent light-sensitive components in diazoWP P otographic copying materials. In the presence of selected coupling components on a suitable support, they have excellent keeping qualities under all ordinary conditions of storage.
the alkaline processing consists ordinarily of subjecting the exposed diazotype sheet to an atmosphere of ammonia vapors but it is also 1 possible to develop the image by means of dilute aqueous solutions of weak alkalies or alkylolamines such as triethanolamine or by means of steam in which case the sensitized coating must contain a suitable alkali incorporated therein.
the base or support carrying or containing the light-sensitive compound or compounds 5 can be paper, cloth or a film such as prepared from cellulose nitrate, cellulose acetate, cellulose acetate-propionate, regenerated cellulose, and.
the sensitizing substance being applied by coating. dipping, brushing, spraying, dusting or by any other means known to one skilled in the art and in accordance with the requirements of the particular support employed. 7
the sensitizing compounds can be applied from asolution containing one or more of our diazo compounds together with one or more selected coupling components and may also have present one or more stabilizing compoundsselected from the group including hydrochloric 2o acid, boric acid, tartaric acid, thiourea, and the like.
the light-sensitive compounds and the coupling compounds are dissolved in separate solutions and applied to the sheet material to be sensitized in sequence.
the stabilizers are usually incorporated in th diazo salt solution. After each application, the sheet may be dried, if desired.
Another modification is to add a thickening or emulsifying agent to the solution or solutions such as gelatin, polyvinyl alcohol, polyvinyl phthalate, cellulose acetate phthalate, gum tragacanth, a higher fatty acid 'glyceryl sulfate or other similar kind of substance.
the solution concentrations of the sensitizing compounds can be varied within fairly wide limits, the preferred range "being up to 2% by weight of the diazo compound and about the same concentration of the coupling compound. Good results have also been obtained with concentrations as high as- 4% by 40 weight of the respective components.
the stabilizers can also be varied within fairly wide limits of concentration.
diazotype copying materials which combine the advantages of good stability, high degree of sensitivity to light and produce prints which are characterized by excellent keeping qualities, good sharpness and contrast. 7 a
heterocyclic intermediates and sensitive 5o diazo compounds were prepared by the following methods.
the reaction mixture was cooled, filtered from the catalyst and treatedwith a solution of 3 cc. of concentrated sulfuric acidin cc. of water.
the precipitate was removed by filtration and dried in air. There resulted 9.7 g. (75 per cent) of the desired product which can be purified further by recrystallization from 100 cc. of 75 per cent aqueous acetic acid.
roduct was purified by recrystallization from 80 per cent ethanol.
CHr-CHg was diazotized in the usual manner.
the final volume of the diazonium compound solution was 100cc.
the white paper was bathed or coated with the above solution and then with-a 1 per cent solution of p-naphthol. dried, exposed, and processed dry in ammonia in the customary manner. A reddish-brown image on a very pale tan or nearly white field was obtained.
Example 2 exposed sensitized paper and the prints obtained therefrom showed considerable improvement over those of Example 1.
diazonium salt solution was added a 10 cc. portion of a stabilizer stock solution consisting of 2 cc. of concentrated I-lCl, 2.0 grams of boric acid, 4.0 grams of tartaric acid and 0.2 gram of thiourea per 100 cc. volume.
the white paper was bathed or coated with the above solution and then with a 1 percent solution of fi-naphthol, dried, exposed and processed dry in ammonia in the customar manner. A pale purple image on a nearly white field was obtained.
a light-sensitive diazotype material comprising a light-sensitive diazo derivative of a compound having-the general formula:
a light-sensitive diazotype material comprising a light-sensitive diazo derivative of a compound having the general formula:

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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)

US497546A 1943-08-05 1943-08-05 Diazotype photographic material Expired - Lifetime US2350843A (en)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
FR955352D FR955352A (de)	1943-08-05
US497546A US2350843A (en)	1943-08-05	1943-08-05	Diazotype photographic material

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US497546A US2350843A (en)	1943-08-05	1943-08-05	Diazotype photographic material

Publications (1)

Publication Number	Publication Date
US2350843A true US2350843A (en)	1944-06-06

Family

ID=23977301

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
US497546A Expired - Lifetime US2350843A (en)	1943-08-05	1943-08-05	Diazotype photographic material

Country Status (2)

Country	Link
US (1)	US2350843A (de)
FR (1)	FR955352A (de)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2537097A (en) *	1945-08-18	1951-01-09	Gen Aniline & Film Corp	Dyeing of textile materials by the use of light-sensitive diazo salts
US2544823A (en) *	1949-02-08	1951-03-13	Universal Oil Prod Co	N-(hydroxy aryl) pyrrolines and pyrrolidines
US2659672A (en) *	1948-01-09	1953-11-17	Hall Harding Ltd	Diazotype photoprinting materials
US2703756A (en) *	1951-12-12	1955-03-08	Gen Aniline & Film Corp	Vesicular prints and process of making same
US3281245A (en) *	1962-03-09	1966-10-25	Keuffel & Esser Co	Diazotype material
US4149888A (en) *	1972-06-26	1979-04-17	Gaf Corporation	Transparent photographic masks
US5278034A (en) *	1990-04-27	1994-01-11	Fuji Photo Film Co., Ltd.	Process for forming color image

0
- FR FR955352D patent/FR955352A/fr not_active Expired
1943
- 1943-08-05 US US497546A patent/US2350843A/en not_active Expired - Lifetime

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2537097A (en) *	1945-08-18	1951-01-09	Gen Aniline & Film Corp	Dyeing of textile materials by the use of light-sensitive diazo salts
US2541178A (en) *	1945-08-18	1951-02-13	Gen Aniline & Film Corp	Photographic process for dyeing of textile materials
US2659672A (en) *	1948-01-09	1953-11-17	Hall Harding Ltd	Diazotype photoprinting materials
US2544823A (en) *	1949-02-08	1951-03-13	Universal Oil Prod Co	N-(hydroxy aryl) pyrrolines and pyrrolidines
US2703756A (en) *	1951-12-12	1955-03-08	Gen Aniline & Film Corp	Vesicular prints and process of making same
US3281245A (en) *	1962-03-09	1966-10-25	Keuffel & Esser Co	Diazotype material
US4149888A (en) *	1972-06-26	1979-04-17	Gaf Corporation	Transparent photographic masks
US5278034A (en) *	1990-04-27	1994-01-11	Fuji Photo Film Co., Ltd.	Process for forming color image

Also Published As

Publication number	Publication date
FR955352A (de)	1950-01-14

Publication	Publication Date	Title
US2298444A (en)	1942-10-13	Light sensitive diazotype material
US2245628A (en)	1941-06-17	Reflex copying process
US3248220A (en)	1966-04-26	Two-component diazotype material
US2593911A (en)	1952-04-22	Diazotypes containing a condensation product of dicyandiamide with formaldehyde and a salt of ammonia or an aromatic amine
US2350843A (en)	1944-06-06	Diazotype photographic material
US2336309A (en)	1943-12-07	Diazotype photographic material
US3140180A (en)	1964-07-07	Heat developable diazotype reproduction coatings comprising thermolabile carboxylic tertiary alkyl esters
US2429249A (en)	1947-10-21	Stabilized aryl diazo-n-sulfonate light-sensitive material
US2994608A (en)	1961-08-01	Reproduction material
CA1146172A (en)	1983-05-10	Derivatives of 2-hydroxy-naphtalene and use thereof as coupling components in diazotype materials
US2548845A (en)	1951-04-10	4-hydroxy-2-alkylbenzimidazoles as azo coupling components in diazotypes
US3910794A (en)	1975-10-07	Imidazole couplers for two component diazotype systems
US3169869A (en)	1965-02-16	Diazotype material
US2532126A (en)	1950-11-28	Diazotype photographic material
US3294542A (en)	1966-12-27	Photosensitive diazo compositions
US2432593A (en)	1947-12-16	Phloroglucide containing diazo photoprinting material
US3281245A (en)	1966-10-25	Diazotype material
US3615578A (en)	1971-10-26	Light-sensitive diazo compounds and light-sensitive material containing them
US2552354A (en)	1951-05-08	Diazotype layers containing diazos of n-(2-hydroxypropyl)-phenylenediamines
US2432549A (en)	1947-12-16	Diazotype layers containing thiourea derivatives of hydroxy benzene
US2946684A (en)	1960-07-26	Diazotype copying processes
US3619191A (en)	1971-11-09	Diazo-type materials
US3379531A (en)	1968-04-23	Two-component heat developing diazotypes
US3406071A (en)	1968-10-15	Naphthol sulfonamides as coupling components for light-sensitive diazotype materials
US3539345A (en)	1970-11-10	Thermal diazotype papers