GB554921A - Improvements in photographic light sensitive diazotype materials - Google Patents
Improvements in photographic light sensitive diazotype materialsInfo
- Publication number
- GB554921A GB554921A GB13285/41A GB1328541A GB554921A GB 554921 A GB554921 A GB 554921A GB 13285/41 A GB13285/41 A GB 13285/41A GB 1328541 A GB1328541 A GB 1328541A GB 554921 A GB554921 A GB 554921A
- Authority
- GB
- United Kingdom
- Prior art keywords
- naphthol
- prepared
- amino
- condensing
- chloride
- 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
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)
- Heat Sensitive Colour Forming Recording (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
554,921. Naphthalene derivatives. KODAK, Ltd. Oct. 15, 1941, No. 13285. Convention date, Oct. 15, 1940. [Class 2 (iii)] [Also in Group XX] Methyl 1-naphthol-5-sulphonate is prepared by heating 1-acetoxynaphthalene-5-sulphonyl chloride with excess of methyl alcohol. 5-Benzylamino-1-naphthol is prepared by condensing 5-amino-1-naphthol with benzaldehyde and reducing the Schiff base catalytically or chemically. 5- Acylamino-1-naphthols are prepared (a) by condensing 2 moles of 5-amino-1-naphthol or 2 moles of a 5-alkylamino-1-naphthol with 1 mole of XC1 (where X represents an acyl group) or (b) by condensing 1 mole of the naphthol compound with 1 mole of XC1 in the presence of sodium acetate and acetic acid. The following compounds are prepared by method (a): 2 : 4 - dibromo - 5 - (N - benzyl - N - - naphthalene - # - sulphon) - amino - 1 naphthol, 2 : 4 - dichloro - 5 - (N - benzyl : N - α - naphthoyl) - amino 1 - naphthol, 2 : 4 - dichloro - 5 - (N - benzyl : N - # - naphthoyl) - amino - 1 - naphthol, 2 : 4 - dichloro - 5 - palmitylamino - 1 - naphthol, (halogenation being effected in these four examples by treatment with sulphuryl chloride or bromine), 5 - (N - benzyl - N - n - amylnaphthalene - α (or #) - sulphon) - amino - 1 - naphthol, 5 - (N - benzyl - N - naphthalene - x - sulphon) - amino - 1 - naphthol, 5 - (N - benzyl N - p - - tert. - amylbenzenesulphon) - amino - 1 - naphthol, 5 - (N - benzyl : N - n - valeryl) - amino - 1 - naphthol, and 5 - (p - sulphamylbenzamido) - 1 - naphthol. The following compounds are prepared by method (b) : 5 - (m : m<SP>1</SP> - dinitrobenzoylamino - 1 - naphthol, 5 - lauroylamino - 1 - naphthol, 5 - methylsulphonylamino - 1 - naphthol, and 5 -(p - - nitrobenzamido) - 1 - naphthol. 1 - - Hydroxy 2 - naphthamides are prepared by condensing 1 mole of 1-hydroxy-2-naphthoyl chloride with 2 moles of a compound of formula R-NH-R<SP>1</SP>, (where R and R<SP>1</SP> may be hydrogen, alkyl, or aryl). Examples are 1-hydroxy-2- (N - iso - amyl - N -, phenyl) - naphthamide, 1 - hydroxy - 2 - (N - ethyl : N - α - naphthyl) - naphthamide, 1 - hydroxy - 2 - (N - methyl) - naphthanilide and 1 - hydroxy - 2 - naphthanilide. 5 - (p - - Acylaminobenzamido) - 1 - - naphthols are prepared by condensing a 5-amino-1- naphthol with p-nitrobenzoyl chloride, reducing the nitro group, and then reacting with sodium acetate and XC1 (where X is an acyl group). Halogenation may be effected with sulphuryl chloride or bromine in a suitable solvent. Examples specified are 5 - [p - (p - acetaminobenzenesulphonamido) - benzamido] - 1 - naphthol, and 2 : 4 - dichloro - 5 - [p - - (p - benzamido) - benzamido] - 1 - naphthol. Dipiperidinomethyl - 1 : 5 - dihydroxynaphthalene is prepared by treating 1:5-dihydroxynaphthalene with formaldehyde and piperidine. 1-Naphthol - 3 : 6 di - (sulphon - N - methylanilide) is prepared by condensing 1- naphthol-3:6-disulphonic acid with sodium acetate and acetic anhydride, treating the product with PC1 5 , and the latter product with methylaniline and sodium acetate, and then hydrolysing with sodium hydroxide. 1 - - Naphthol 4 - - sulphon - ( N - ethyl - α- naphthalide) is prepared by condensing 4- propionyloxynaphthalenesulphonyl chloride with α-ethylnaphthylamine and sodium acetate and hydrolysing with sodium hydroxide. 2 - n valeryl - 1 - naphthol is prepared by heating α-naphthol with valeric anhydride and zinc chloride. 4 - n - valeryl - 1 - naphthol is prepared by condensing α-methoxynaphthalene with valeryl chloride and aluminium chloride.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US361263A US2298444A (en) | 1940-10-15 | 1940-10-15 | Light sensitive diazotype material |
Publications (1)
Publication Number | Publication Date |
---|---|
GB554921A true GB554921A (en) | 1943-07-26 |
Family
ID=23421319
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB11332/43A Expired GB554998A (en) | 1940-10-15 | 1941-10-15 | Improvements in photographic light sensitive diazotype materials |
GB13285/41A Expired GB554921A (en) | 1940-10-15 | 1941-10-15 | Improvements in photographic light sensitive diazotype materials |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB11332/43A Expired GB554998A (en) | 1940-10-15 | 1941-10-15 | Improvements in photographic light sensitive diazotype materials |
Country Status (3)
Country | Link |
---|---|
US (1) | US2298444A (en) |
FR (1) | FR907964A (en) |
GB (2) | GB554998A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3791832A (en) * | 1968-05-15 | 1974-02-12 | Ricoh Kk | Diazotype photoprinting material |
Families Citing this family (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2537098A (en) * | 1946-04-12 | 1951-01-09 | Gen Aniline & Film Corp | Sulfonamide azo coupling components used in diazo types |
BE473113A (en) * | 1946-05-08 | |||
US2490605A (en) * | 1946-05-24 | 1949-12-06 | Gen Aniline & Film Corp | Diazotype light-sensitive layers containing 4-bromoresorcinol |
US2431190A (en) * | 1946-06-12 | 1947-11-18 | Gen Aniline & Film Corp | Diazotype prints with hydroxy pyridone couplers |
US2545057A (en) * | 1946-06-12 | 1951-03-13 | Gen Aniline & Film Corp | Diazotypes containing resorcinol sulfonic acids as coupling components |
US2551570A (en) * | 1946-10-24 | 1951-05-01 | Gen Aniline & Film Corp | Azo dye components of the amino naphthol series for diazotypes |
GB644493A (en) * | 1948-01-09 | 1950-10-11 | Hall Harding Ltd | Improvements relating to the production of diazotype photo printing materials |
US2616803A (en) * | 1948-03-11 | 1952-11-04 | Leonard E Ravich | Diazotype dyeing and printing of web or sheet material |
BE546008A (en) * | 1955-03-17 | |||
DE1068555B (en) * | 1957-02-04 | 1959-11-05 | ||
US2948613A (en) * | 1957-07-26 | 1960-08-09 | Gen Aniline & Film Corp | Diazotype materials sensitized with n-hetero-p-aminobenzenediazonium salts |
GB867432A (en) * | 1958-09-22 | 1961-05-10 | Gen Aniline & Film Corp | Two-component diazotype materials yielding prints with substantially no background discoloration and being free from sulfur stabilizers |
NL248308A (en) * | 1958-09-30 | |||
NL296260A (en) * | 1962-08-15 | |||
US3480437A (en) * | 1965-11-30 | 1969-11-25 | Gaf Corp | Two component diazo sensitizing compositions containing a xanthine compound |
US3497355A (en) * | 1968-01-11 | 1970-02-24 | Gaf Corp | Diazotype reproduction material comprising a diazonium compound and method of use |
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 |
US4054456A (en) * | 1972-04-21 | 1977-10-18 | Fuji Photo Film Co., Ltd. | Diazo photographic materials containing 2-hydroxy 3-naphthanilide coupler |
DE2903342A1 (en) * | 1979-01-29 | 1980-07-31 | Hoechst Ag | DERIVATIVES OF 2-HYDROXY NAPHTHALINE |
-
1940
- 1940-10-15 US US361263A patent/US2298444A/en not_active Expired - Lifetime
-
1941
- 1941-10-15 GB GB11332/43A patent/GB554998A/en not_active Expired
- 1941-10-15 GB GB13285/41A patent/GB554921A/en not_active Expired
-
1943
- 1943-10-07 FR FR907964D patent/FR907964A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3791832A (en) * | 1968-05-15 | 1974-02-12 | Ricoh Kk | Diazotype photoprinting material |
Also Published As
Publication number | Publication date |
---|---|
US2298444A (en) | 1942-10-13 |
FR907964A (en) | 1946-03-27 |
GB554998A (en) | 1943-07-28 |
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