US2531091A - N-acetonyl-pyridinium chloride as an azo coupling component in diazotypes - Google Patents
N-acetonyl-pyridinium chloride as an azo coupling component in diazotypes Download PDFInfo
- Publication number
- US2531091A US2531091A US686951A US68695146A US2531091A US 2531091 A US2531091 A US 2531091A US 686951 A US686951 A US 686951A US 68695146 A US68695146 A US 68695146A US 2531091 A US2531091 A US 2531091A
- Authority
- US
- United States
- Prior art keywords
- diazotypes
- acetonyl
- pyridinium chloride
- coupling component
- azo coupling
- 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
- JHYYWKUENNZTMD-UHFFFAOYSA-M 1-pyridin-1-ium-1-ylpropan-2-one;chloride Chemical compound [Cl-].CC(=O)C[N+]1=CC=CC=C1 JHYYWKUENNZTMD-UHFFFAOYSA-M 0.000 title description 4
- 238000006149 azo coupling reaction Methods 0.000 title 1
- 238000010168 coupling process Methods 0.000 description 11
- 230000008878 coupling Effects 0.000 description 10
- 238000005859 coupling reaction Methods 0.000 description 10
- 150000008049 diazo compounds Chemical class 0.000 description 6
- 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 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 3
- 229960001553 phloroglucinol Drugs 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- QNGVNLMMEQUVQK-UHFFFAOYSA-N 4-n,4-n-diethylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C=C1 QNGVNLMMEQUVQK-UHFFFAOYSA-N 0.000 description 1
- 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 1
- BUACSMWVFUNQET-UHFFFAOYSA-H dialuminum;trisulfate;hydrate Chemical compound O.[Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O BUACSMWVFUNQET-UHFFFAOYSA-H 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 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
- G03C1/58—Coupling substances therefor
Definitions
- This invention relates to a process for preparing diazotypes.
- the primary object of this invention is to provide a color coupler to be used in the preparation of diazotypes which is of great effectiveness.
- R represents aryl, alkyl or aralkyl
- X represents H, aryl, alkyl, aralkyl, acyl or a hydroaromatic residue
- Y represents H, aryl, alkyl, aralkyl, acyl or a hydroaromatic residue.
- I employ N- acetonyl-pyridinium chloride as a coupler.
- my new coupling component is its great solubility and its quality of rapidly coupling and giving very intense dyestuffs with the usual diazo compounds.
- the coupling element of my invention may be used singly or in any combination. Whenused in mixtures, diazotypes of very intense neutral color are obtained whereas, for instance, the use of phloroglucinol alone produces only a brown violet color.
- EwampZe.-To a suitable paper is applied a solution of 1.5 g. of diazonium compound from p-diethylamino aniline, 1 g. of tartaric acid, 0.8 g. of aluminum sulphate, 0.15 g. of phloroglucinol and 0.08 g. of N-acetonylpyridinium chloride in cm. of water.
- the paper is exposed through a diapositive and developed in an ammoniacal atmosphere.
- the paper is exposed through a diapositive and developed in an ammoniacal atmosphere. A dark magenta print is obtained.
- My new coupling component may be added either to the developer when the half-wet process is used, or to a solution which contains one or more diazo compounds and which is applied as light-sensitive layer to an adapted paper.
- the method which comprises selectively exposing a lightsensitive material containing a light-sensitive diazo compound, and coupling the diazo compound retained in the unexposed areas with N- acetonyl-pyridinium chloride.
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE266905X | 1945-08-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2531091A true US2531091A (en) | 1950-11-21 |
Family
ID=3866827
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US686951A Expired - Lifetime US2531091A (en) | 1945-08-03 | 1946-07-29 | N-acetonyl-pyridinium chloride as an azo coupling component in diazotypes |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US2531091A (en(2012)) |
| BE (1) | BE459543A (en(2012)) |
| CH (1) | CH266905A (en(2012)) |
| ES (1) | ES176413A1 (en(2012)) |
| FR (1) | FR931187A (en(2012)) |
| GB (1) | GB617115A (en(2012)) |
| NL (1) | NL62542C (en(2012)) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3307952A (en) * | 1963-11-20 | 1967-03-07 | Ibm | Formation of diazo couplers in situ |
| US4130426A (en) * | 1974-04-22 | 1978-12-19 | Fuji Photo Film Co., Ltd. | Heat developable light-sensitive diazotype materials and process of use |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE489248A (en(2012)) * | 1948-11-05 | |||
| DE966201C (de) * | 1953-08-14 | 1957-07-18 | Bayer Ag | Verfahren zur Herstellung von Cyclohexanonoxim durch katalytische Hydrierung von Nitrocyclohexansalzen |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1822065A (en) * | 1928-10-19 | 1931-09-08 | Kalle & Co Ag | Azo dyestuff components and process of preparing them |
| US2027229A (en) * | 1931-07-08 | 1936-01-07 | Frederick Post Company | Accelerated diazo printing and materials therefor |
| US2154918A (en) * | 1937-07-30 | 1939-04-18 | Agfa Ansco Corp | Coupling compounds for color forming development |
| US2217189A (en) * | 1938-12-05 | 1940-10-08 | Kalle & Co Ag | Process of preparing photographic prints |
| US2331326A (en) * | 1939-07-22 | 1943-10-12 | Ilford Ltd | Production of colored photographic images |
| US2405523A (en) * | 1944-08-09 | 1946-08-06 | Du Pont | Light-sensitive photographic compositions and elements |
-
0
- NL NL62542D patent/NL62542C/xx active
-
1945
- 1945-08-03 BE BE459543D patent/BE459543A/xx unknown
-
1946
- 1946-07-24 FR FR931187D patent/FR931187A/fr not_active Expired
- 1946-07-29 US US686951A patent/US2531091A/en not_active Expired - Lifetime
- 1946-08-01 GB GB22906/46A patent/GB617115A/en not_active Expired
- 1946-08-02 CH CH266905D patent/CH266905A/fr unknown
-
1947
- 1947-01-03 ES ES176413A patent/ES176413A1/es not_active Expired
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1822065A (en) * | 1928-10-19 | 1931-09-08 | Kalle & Co Ag | Azo dyestuff components and process of preparing them |
| US2027229A (en) * | 1931-07-08 | 1936-01-07 | Frederick Post Company | Accelerated diazo printing and materials therefor |
| US2154918A (en) * | 1937-07-30 | 1939-04-18 | Agfa Ansco Corp | Coupling compounds for color forming development |
| US2217189A (en) * | 1938-12-05 | 1940-10-08 | Kalle & Co Ag | Process of preparing photographic prints |
| US2331326A (en) * | 1939-07-22 | 1943-10-12 | Ilford Ltd | Production of colored photographic images |
| US2405523A (en) * | 1944-08-09 | 1946-08-06 | Du Pont | Light-sensitive photographic compositions and elements |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3307952A (en) * | 1963-11-20 | 1967-03-07 | Ibm | Formation of diazo couplers in situ |
| US4130426A (en) * | 1974-04-22 | 1978-12-19 | Fuji Photo Film Co., Ltd. | Heat developable light-sensitive diazotype materials and process of use |
Also Published As
| Publication number | Publication date |
|---|---|
| FR931187A (fr) | 1948-02-16 |
| CH266905A (fr) | 1950-02-28 |
| GB617115A (en) | 1949-02-01 |
| BE459543A (en(2012)) | 1900-01-01 |
| ES176413A1 (es) | 1948-07-01 |
| NL62542C (en(2012)) |
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