US2494906A - Cyan component for diazotype color process - Google Patents
Cyan component for diazotype color process Download PDFInfo
- Publication number
- US2494906A US2494906A US753036A US75303647A US2494906A US 2494906 A US2494906 A US 2494906A US 753036 A US753036 A US 753036A US 75303647 A US75303647 A US 75303647A US 2494906 A US2494906 A US 2494906A
- Authority
- US
- United States
- Prior art keywords
- diazotype
- cyan
- color process
- naphthalene
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims description 12
- -1 AMINO GROUPS Chemical group 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 6
- 150000008049 diazo compounds Chemical class 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- ADQAFJJAAZDWCY-UHFFFAOYSA-N 4-ethoxy-1-n,1-n-diethylbenzene-1,3-diamine Chemical compound CCOC1=CC=C(N(CC)CC)C=C1N ADQAFJJAAZDWCY-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 229910021529 ammonia Inorganic materials 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
- 235000019441 ethanol Nutrition 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 230000001235 sensitizing effect Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 235000005074 zinc chloride Nutrition 0.000 description 3
- 239000011592 zinc chloride Substances 0.000 description 3
- NKJAYTHAELPXCQ-UHFFFAOYSA-N 8-amino-1-hydroxy-2h-naphthalene-1-sulfonic acid Chemical class C1=CCC(O)(S(O)(=O)=O)C2=C1C=CC=C2N NKJAYTHAELPXCQ-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 241000974482 Aricia saepiolus Species 0.000 description 2
- 125000004442 acylamino group Chemical group 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 125000001769 aryl amino group Chemical group 0.000 description 2
- 238000006149 azo coupling reaction Methods 0.000 description 2
- YKYOUMDCQGMQQO-UHFFFAOYSA-L cadmium dichloride Chemical compound Cl[Cd]Cl YKYOUMDCQGMQQO-UHFFFAOYSA-L 0.000 description 2
- 229920002301 cellulose acetate Polymers 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- OGNVQLDIPUXYDH-ZPKKHLQPSA-N (2R,3R,4S)-3-(2-methylpropanoylamino)-4-(4-phenyltriazol-1-yl)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid Chemical compound CC(C)C(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)OC(C(O)=O)=C[C@@H]1N1N=NC(C=2C=CC=CC=2)=C1 OGNVQLDIPUXYDH-ZPKKHLQPSA-N 0.000 description 1
- OGSZAQASQUXQOD-UHFFFAOYSA-N 2,3-dihydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(O)(=O)=O)=C(O)C(O)=CC2=C1 OGSZAQASQUXQOD-UHFFFAOYSA-N 0.000 description 1
- YGNDWDUEMICDLW-UHFFFAOYSA-N 7-anilino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C=1C=C2C(O)=CC(S(O)(=O)=O)=CC2=CC=1NC1=CC=CC=C1 YGNDWDUEMICDLW-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- OODCFCAUIVIKTC-UHFFFAOYSA-N CNC1=CC=CC2=CC=CC(=C12)O Chemical compound CNC1=CC=CC2=CC=CC(=C12)O OODCFCAUIVIKTC-UHFFFAOYSA-N 0.000 description 1
- 229920008347 Cellulose acetate propionate Polymers 0.000 description 1
- DQEFEBPAPFSJLV-UHFFFAOYSA-N Cellulose propionate Chemical compound 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 DQEFEBPAPFSJLV-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000005228 aryl sulfonate group Chemical group 0.000 description 1
- 238000006254 arylation reaction Methods 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229920006218 cellulose propionate Polymers 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000004989 p-phenylenediamines Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 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
Definitions
- the present invention relates to sensitized diazotype materials'for the diazotype color process which when exposed through a cyan separation positive and developed yield greenish blue images of high intensity.
- the diazotype process be utilized for the purpose of manufacturing natural color prints.
- the method suggested involved printing separation positives in the primary colors on separate transparent plastic film layers, dryedeveloping the layers and transposing the layers in register to produce a color print.
- R is hydroxyl, amino, acylamino, such as, acetylamino, propionylamino, butyrylamino, benzoylamino, and the like, alkylamino, such as,
- acyl derivatives mentioned above may be prepared by treatment of the 1-hydroxy-8-amino-naphthalene sulfonic acids with the anhydrides of the acids involved just as in the preparation of, for instance, acetyl J acid;
- the l-hydroXy-B-amino-naphthalene sulfonic acids in which the amino groupie substituted by alkyl or aryl may be prepared by alkylation and arylation, just as in the preparation of, for instance, dimethyl-2-amino-8-naphthol 6-su1fonic acid or of phenyl J acid.
- diazos which we have found to yield excellent results are those derived from the following compounds:
- p-amino-N-diethyl-o-toluidine 4-diethylamino-o-phenetidine p- (N-ethyl-N-hydroxyethylamino) -o-to1uidine water or mixtures of water and a low molecular weight alcohol, 1. e., methyl alcohol, ethyl alcohol, and the like.
- the base to which the sensitizing compositions are applied may be a sheet, film, or the like, of any transparent film-forming material preferably a cellulose ester, such as, cellulose acetate, cellulose propionate, cellulose acetate propionate, and the like.
- a cellulose ester such as, cellulose acetate, cellulose propionate, cellulose acetate propionate, and the like.
- the sensitized base is utilized in the manner outlined above, that is, by exposure under a desired cyan separation positive by U. V. light and development by ammonia fumes.
- Emample I A cellulose acetate film is coated with a solution of the following components:
- Example II Example III The procedure is the same as in Example I excepting that 1-hydroxy-8-acetylamino-naph- 55 thalene-4- sulf'onic acid is substituted for the dihydroxy-naphthalene sulfonic acid.
- the processing of the resulting film leads to greenish-blue positives of high density.
- R is a member selected from the class consisting of hydroxyl, amino, acylamino, alkylamino, and arylamino.
- the light sensitive diazo compound is the zinc chloride double salt of the diazo from 4-diethylaminoo-phenetidine and the azo coupling component is 1.8-dihydroxy-naphthalene-4-sulfonic acid.
- the process of producing cyan diazotype prints capable of transmitting both green and blue light comprises sensitizing a transparent base with a composition containing as a light sensitive diazo compound a diazotized p-phenylene-diamine in which one of the amino groups is di-substituted by members selected from the class consisting of alkyl and hydroxyalkyl and as a coupling component a compound of the following formula:
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)
- Color Printing (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL62286500A NL140419B (nl) | 1947-06-06 | Werkwijze voor het bereiden van een minstens twee componenten met verschillende dampspanningen bevattende damp. | |
| NL69307D NL69307C (enrdf_load_stackoverflow) | 1947-06-06 | ||
| US753036A US2494906A (en) | 1947-06-06 | 1947-06-06 | Cyan component for diazotype color process |
| GB9137/48A GB635120A (en) | 1947-06-06 | 1948-03-31 | Cyan azo-coupling component for diazotype color process |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US753036A US2494906A (en) | 1947-06-06 | 1947-06-06 | Cyan component for diazotype color process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2494906A true US2494906A (en) | 1950-01-17 |
Family
ID=25028879
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US753036A Expired - Lifetime US2494906A (en) | 1947-06-06 | 1947-06-06 | Cyan component for diazotype color process |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US2494906A (enrdf_load_stackoverflow) |
| GB (1) | GB635120A (enrdf_load_stackoverflow) |
| NL (2) | NL140419B (enrdf_load_stackoverflow) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2694009A (en) * | 1948-10-01 | 1954-11-09 | Keuffel & Esser Co | Diazo-n-sulfonate light-sensitive material |
| DE1035474B (de) * | 1951-11-30 | 1958-07-31 | American Optical Corp | Verfahren zur Herstellung von photographischen Mehrfarbenbildern durch Traenken eines Polyvinylalkoholfilms mit Diazoverbindungen und Aufkopieren der Teilfarbenbilder |
| US3406071A (en) * | 1963-09-14 | 1968-10-15 | Keuffel & Esser Co | Naphthol sulfonamides as coupling components for light-sensitive diazotype materials |
| US3480437A (en) * | 1965-11-30 | 1969-11-25 | Gaf Corp | Two component diazo sensitizing compositions containing a xanthine compound |
| US3536490A (en) * | 1964-04-28 | 1970-10-27 | Pitney Bowes Inc | Novel diazotype copying process |
| US3769013A (en) * | 1968-08-07 | 1973-10-30 | Mita Industrial Co Ltd | Wet type diazotype developer |
| US3849138A (en) * | 1961-03-24 | 1974-11-19 | Applied Photo Sciences | Color photography |
| CN110670074A (zh) * | 2019-11-05 | 2020-01-10 | 朱玉军 | 一种环保型螺纹钢表面防锈处理剂及其制备方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1710455A (en) * | 1926-07-09 | 1929-04-23 | Langguth Werner | Process for producing photographs in natural colors |
| US2375366A (en) * | 1941-10-16 | 1945-05-08 | Keuffel & Esser Co | Photosensitive materials |
-
0
- NL NL69307D patent/NL69307C/xx active
- NL NL62286500A patent/NL140419B/xx unknown
-
1947
- 1947-06-06 US US753036A patent/US2494906A/en not_active Expired - Lifetime
-
1948
- 1948-03-31 GB GB9137/48A patent/GB635120A/en not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1710455A (en) * | 1926-07-09 | 1929-04-23 | Langguth Werner | Process for producing photographs in natural colors |
| US2375366A (en) * | 1941-10-16 | 1945-05-08 | Keuffel & Esser Co | Photosensitive materials |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2694009A (en) * | 1948-10-01 | 1954-11-09 | Keuffel & Esser Co | Diazo-n-sulfonate light-sensitive material |
| DE1035474B (de) * | 1951-11-30 | 1958-07-31 | American Optical Corp | Verfahren zur Herstellung von photographischen Mehrfarbenbildern durch Traenken eines Polyvinylalkoholfilms mit Diazoverbindungen und Aufkopieren der Teilfarbenbilder |
| US3849138A (en) * | 1961-03-24 | 1974-11-19 | Applied Photo Sciences | Color photography |
| US3406071A (en) * | 1963-09-14 | 1968-10-15 | Keuffel & Esser Co | Naphthol sulfonamides as coupling components for light-sensitive diazotype materials |
| US3536490A (en) * | 1964-04-28 | 1970-10-27 | Pitney Bowes Inc | Novel diazotype copying process |
| US3480437A (en) * | 1965-11-30 | 1969-11-25 | Gaf Corp | Two component diazo sensitizing compositions containing a xanthine compound |
| US3769013A (en) * | 1968-08-07 | 1973-10-30 | Mita Industrial Co Ltd | Wet type diazotype developer |
| CN110670074A (zh) * | 2019-11-05 | 2020-01-10 | 朱玉军 | 一种环保型螺纹钢表面防锈处理剂及其制备方法 |
| CN110670074B (zh) * | 2019-11-05 | 2021-11-16 | 北美防锈技术（上海）有限公司 | 一种环保型螺纹钢表面防锈处理剂及其制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| GB635120A (en) | 1950-04-05 |
| NL140419B (nl) | |
| NL69307C (enrdf_load_stackoverflow) |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2793118A (en) | One component diazotype material containing at least two light sensitive diazocompounds | |
| US2494906A (en) | Cyan component for diazotype color process | |
| US3113025A (en) | Diazotype materials for the production of black images | |
| US3964911A (en) | Photographic reproduction processes using diazonium salts and substituted spiro[benzopyrane] | |
| US2552354A (en) | Diazotype layers containing diazos of n-(2-hydroxypropyl)-phenylenediamines | |
| US2432549A (en) | Diazotype layers containing thiourea derivatives of hydroxy benzene | |
| US2537106A (en) | Poly-acetoacetyl derivatives of polyamines as azo components in diazotype photoprinting material | |
| GB274129A (en) | Process for producing photographs in natural colours | |
| US2946684A (en) | Diazotype copying processes | |
| US2672418A (en) | Light-sensitive diazotype material | |
| US3622326A (en) | Diazotype light-sensitive copying papers intended for wet development and for use in the preparation of intermediates | |
| US2536398A (en) | Pyrazolone diazotype couplers | |
| US2516931A (en) | Diazotype layers containing resorcinol mono-ethers | |
| US2542716A (en) | Multicolor diazotype layers | |
| US2432593A (en) | Phloroglucide containing diazo photoprinting material | |
| US2552355A (en) | Diazotype layers having organic esters and nitriles containing an active methylene group as azo components | |
| US2542560A (en) | Diazotypes on plastic surfaced carrier containing 5,5' diresorcinol | |
| US3081166A (en) | Process for making positive diazotype copies by exposure to light of a mercury vaporlamp and light-sensitive material suited for this process | |
| US2437868A (en) | Diazotype layers containing resorcinol monoesters | |
| US2560137A (en) | Diazotype photoprinting material | |
| US3653903A (en) | Diazo-type multicolor reproduction process | |
| US2411811A (en) | Light-sensitive materials | |
| US2542849A (en) | Diazotypes containing pyronones | |
| US2467358A (en) | Preparation of diazo prints utilizing resorcinol carbonamides as coupling components | |
| US2442061A (en) | Acid stabilized light-sensitive diazotype coating |