GB378870A - Improvements in and relating to the manufacture of light-sensitive photographic materials - Google Patents
Improvements in and relating to the manufacture of light-sensitive photographic materialsInfo
- Publication number
- GB378870A GB378870A GB9448/32A GB944832A GB378870A GB 378870 A GB378870 A GB 378870A GB 9448/32 A GB9448/32 A GB 9448/32A GB 944832 A GB944832 A GB 944832A GB 378870 A GB378870 A GB 378870A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- naphthothiazole
- trimethyl
- condensed
- dry
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
- C09B23/06—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups three >CH- groups, e.g. carbocyanines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Thiocarbocyanines are prepared by condensing a quaternary salt of a 2-methyl-b -naphthothiazole or a 1-methyl-a -naphthothiazole with an orthocarboxylic acid ester having an alkyl, aralkyl, or aryl group linked directly to the carboxy carbon atom. The preparation of 8-methyl-2.2<1> - dialkyl - 5.6 : 5<1>.6<1> - dibenzothio - carbocyanine by condensation of a 1-methyl-a -naphthothiazole quaternary salt with an ester of orthoacetic acid ester is excluded. An excess of the orthocarboxylic acid ester is preferably employed. In examples, (1) 2-methyl-b -naphthothiazole is condensed with ethyl-p-toluenesulphonate and the resulting quaternary salt condensed with two mols. of triethyl orthoacetate in pyridine; ammonium bromide is then added to give 8-methyl-2.2<1>-diethyl-3.4 : 3<1>.4<1>-dibenzothiocarbocyanine bromide; if methyl-p-toluenesulphonate be employed instead of the corresponding ethyl body 2.2<1>.8-trimethyl - 3.4 : 3<1>.4<1> - dibenzothiocarbocyanine bromide results; the acid radicle can also be changed: (2) 2-methyl-b -naphthothiazole ethyl-p-toluenesulphonate is condensed with 2 mols. of trimethyl orthopropionate in dry pyridine and a hot solution of potassium iodide added to give 2.2<1>.8-triethyl-3.4 : 3<1>.4<1> dibenzothiocarbocyanine iodide: (3) 2-methyl-b -naphthothiazole methyl p-toluenesulphonate is condensed with 2 mols. of methyldiethyl orthoisocaproate in dry pyridine, and potassium iodide added to give 2.2<1>-dimethyl-8-isoamyl-3.4 : 3<1>.4<1>-dibenzothiocarbocyanine iodide. The preparation of other 8-substituted derivatives and of the corresponding dyes from 1-methyl-a -naphthothiazole proceeds on similar lines. The thiazoles may be substituted in the fused-on benzene ring; thus 1-amino-4-ethoxynaphthalene, 1-amino-4-methoxynaphthalene, or 2-amino-7-methoxynaphthalene or acetyl derivatives of these may be treated in the known manner to produce a m -methylnaphthothiazole, and a quaternary salt of the latter, for example of a m -methyl-4-ethoxynaphthothiazole, is then condensed with an orthocarboxylic acid ester. Dyes in which the alkyl groups in the 2.2<1>-positions are dissimilar are obtained by treating a mixture of two quaternary salts of the m -methylnaphthothiazole whereby a mixture of products is obtained, one constituent of which contains the desired dissimilar alkyl substituents. Orthocarboxylic acid esters other than orthoformic esters are prepared by dissolving the corresponding acid nitrile in dry ethyl ether together with a dry alcohol, such as methyl or ethyl alcohol, and passing in dry hydrochloric acid gas. The imino-ether hydrochloride separates, and is washed and dried prior to treatment with more dry alcohol. The orthocarboxylic acid ester so formed is distilled over under reduced pressure. Thus trimethyl orthopropionate is derived from propionitrile by using methyl alcohol in each stage, trimethyl orthophenylacetate from benzyl cyanide, trimethyl-ortho-g -phenoxybutyrate from g -phenoxybutyronitrile, triethyl-orthobenzoate from benzonitrile, trimethyl ortho-p-toluate from p-tolunitrile. Mixed esters may be obtained by employing two different alcohols in the two stages of the preparation; thus isocapronitrile may first be converted to isocaproiminomethylether hydrochloride by the joint action of methyl alcohol and hydrochloric acid gas, and then by further treatment with ethyl alcohol methyldiethyl orthoisocaproate is obtained. Specification 378,885 also is referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US378870XA | 1930-03-12 | 1930-03-12 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB378870A true GB378870A (en) | 1932-08-12 |
Family
ID=21896891
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB9448/32A Expired GB378870A (en) | 1930-03-12 | 1931-03-12 | Improvements in and relating to the manufacture of light-sensitive photographic materials |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB378870A (en) |
-
1931
- 1931-03-12 GB GB9448/32A patent/GB378870A/en not_active Expired
Similar Documents
Publication | Publication Date | Title |
---|---|---|
ES391299A1 (en) | 2-(n-allyl-phenylamino)-imidazolines-(2)and salts thereof | |
GB378870A (en) | Improvements in and relating to the manufacture of light-sensitive photographic materials | |
GB862445A (en) | Cyanine dyes and photographic emulsions containing them | |
GB968396A (en) | Improvements in dye sensitized photographic emulsions | |
GB615205A (en) | Improvements in and relating to the manufacture of dyes and photographic emulsions sensitised therewith | |
SU415868A3 (en) | METHOD OF OBTAINING BENZOLSULPHONYLMOLOVA | |
US2644003A (en) | Quaternary ammonium compounds and their manufacture | |
ES446700A1 (en) | Biphenyl derivatives and pharmaceutical compositions thereof | |
US2468577A (en) | Process of preparing omega ketones usable as intermediate products for the manufacture of polymethine dyes | |
GB415949A (en) | Process for sensitising photographic silver halide emulsions | |
GB631757A (en) | Improvements in or relating to a method of preparing triacylmelamines | |
GB571174A (en) | Improvements in or relating to the production of photographic light-sensitive emulsions | |
SE8003874L (en) | PROCEDURE FOR PREPARING BROMHEXINE AND AGENTS FOR USING THE PROCEDURE | |
GB617137A (en) | Manufacture of common salt from brine | |
GB392410A (en) | Manufacture of carbocyanine dyes and intermediate products | |
GB593023A (en) | Improvements in photographic emulsions and in the manufacture of dyes therefor | |
SU110969A1 (en) | Method for sensitizing photographic chloro-silver emulsions | |
SU410068A1 (en) | Method of producing phosphorus-containing polymethine dyes | |
ES406367A1 (en) | Thiazolino-pyrimidin-5-one derivatives, process for their preparation and applications thereof | |
GB639218A (en) | Process for the preparation of diaminotriazines | |
GB344409A (en) | Improvements in and relating to the manufacture of intermediates and dyes from heterocyclic nitrogen compounds | |
GB511940A (en) | Improvements in and relating to the production of carbocyanine-like dyestuffs and tothe sensitising of photographic silver halide emulsions | |
GB641452A (en) | Improvements in or relating to the preparation of derivatives of phenthiazine | |
GB599631A (en) | Polymethin dyes and photographic emulsions containing them | |
GB779065A (en) | Photographic emulsions |