Patent GB-700734-A (GB)
Title: Improvements in sensitized photographic emulsions and in sensitizing dyes therefor
IPC: G03C1/22
Filed: 1952-02-15
Abstract: N-Dithiocarbo-n-octoxyglycine is prepared by adding an ethanol solution of n-octyl bromide to a solution of glycine and carbon disulphide in aqueous potassium hydroxide, heating, adding water, extracting with ether, and acidifying the aqueous layer. N-Dithiocarbo-n - hexoxyglycine, - n - heptoxyglycine, - n - decoxyglycine, - n - dodecoxyglycine, and g  - phenylpropoxyglycine are similarly prepared.ALSO:Merocyanine dyes of the general formula <FORM:0700734/IV(c)/1> wherein R and R1 are alkyl or substituted alkyl, L is methine or substituted methine, n is 1 or 2, d is 1, 2, or 3, and Z represents the non-metallic atoms necessary to complete a heterocyclic nucleus containing 5 or 6 atoms in the heterocyclic ring, are prepared, wherein d is 1, by condensing a compound of the general formula <FORM:0700734/IV(c)/2> with a cyclammonium quaternary salt of the general formula <FORM:0700734/IV(c)/3> wherein Y is an electronegative atom or group, e.g. Cl, Br, alkoxy, or -S-R2 (wherein R2 is alkyl or aryl) and X is an anion, and, wherein d is 2 or 3, by condensing a compound of the general formula II with a cyclammonium-quaternary salt of the general formula <FORM:0700734/IV(c)/4> wherein R3 is acyl, R4 is H or aryl, p is 1 or 2 and X is an anion [2-(3-Ethylbenzoxazole)]-[4-(2-ethylthio-5-thiazolone) ]-dimethinemerocyanine is prepared by refluxing 2-ethylthio-4-ethoxymethylene-5-thiazolone (obtained by heating together N-dithiocarbethoxyglycine, acetic anhydride, and ethyl orthoformate) with 2-methylbenzoxazole ethiodide, ethanol, and triethylamine.  [2-(1-Ethylquinoline)] [4-(2-ethylthio-5-thiazolone)]-dimethinemerocyanine, [2-(3-ethylbenzselenazole)] [4-(2-ethylthio-5-thiazolone)]-dimethinemerocyanine, [2-(3-methylthiazoline) [4-(2-ethylthio-5-thiazolone)]-dimethinemerocyanine, [2-(3-ethyl-4-methylthiazole] [4-(2-ethylthio-5-thiazolone)]-dimethinemerocyanine, [4-(1-ethylquinoline)] [4-(2-ethylthio-5-thiazolone)]-dimethinemerocyanine, [2-3-ethylbenzthiazole)] [4-(2-ethylthio-5-thiazolone)]-dimethinemerocyanine, [2-(3-ethyl-4-tolylthiazole)] [4-(2-ethylthio-5-thiazolone)]-dimethinemerocyanine, (2-(1-ethyl-b -naphthathiazole)] [4-(2-ethylthio-5-thiazolone)]-dimethinemerocyanine, [2-(3-ethylbenzoxazole)] [4-(2-ethylthio-5-thiazolone)]-b -methyldimethinemerocyanine, [2-(3-ethylbenzthiazole)] [4-(2-ethylthio-5-thiazolone)]-b -methyldimethinemerocyanine, [2-(3-ethylbenzselenazole)] [4-2-ethylthio-5-thiazolone)]-b -methyldimethinemerocyanine, [2-(3-methylthiazoline] [4-(2-ethylthio-5-thiazolone)]-b -methyldimethinemerocyanine, [2-(1-ethylquinoline)] [4-(2-ethylthio-5-thiazolone)]-b -methyldimethinemerocyanine, [2-(3-ethyl-4-methylthiazole)] [4-(2-ethylthio-5-thiazolone)]-b -methyldimethinemerocyanine, [2-(1-ethylquinoline)] [4-(2-benzylthio-5-thiazolone)]-dimethinemerocyanine, [2-(3-ethylbenzthiazole)] [4-2-benzylthio - 5 - thiazolone)] - dimethinemerocyanine, [2 - (3 - ethylbenzselenazole)] [4 - (2 - benzylthio - 5 - thiazolone)] - dimethinemerocyanine, [2 - (3 - ethylbenzoxazole)] [4-(2 - benzylthio - 5 - thiazolone)] - dimethinemerocyanine, [2 - (1 - ethylpyridine)] [4 - (2 - benzylthio - 5 - thiazolone)]-dimethinemerocyanine, [4 - (1 - ethylquinoline)] [4 - (2 - benzylthio - 5 - thiazolone)] - dimethinemerocyanine, [2 - (3 - methylthiazoline)] [4 - (2 - benzylthio-5-thiazolone)]-dimethinemerocyanine, [2 - (1 - ethyl - b - naphthathiazole)] [4-(2-benzylthio-5-thiazolone)]-dimethinemerocyanine, [4-(1-methylpyridine)] [4-(2-benzylthio-5-thiazolone)]-dimethinemerocyanine, [2-3-methylthiazolone)] [4-(2-n-octylthio-5-thiazolone)]-dimethinemerocyanine, [2-(3-ethylthiazoline)] [4-(2-n-octylthio-5-thiazolone)]-dimethinemerocyanine, [2-(3-ethylbenzoxazole)] [4-(2-n-octylthio-5-thiazolone)]-dimethinemerocyanine, [2-(5-chloro-3-ethylbenzthiazole)] [4-(2-n-octylthio-5-thiazolone)]-dimethinemerocyanine, [2-(3-ethylbenzthiazole)] [4-(2-n-[octylthio-5-thiazolone)]-dimethinemerocyanine, [2-(3-ethylbenzselenazole)] [4-(2-n-octylthio-5-thiazolone)]-dimethinemerocyanine, [2-(3-ethylthiazoline)] [4-(2-ethylthio-5-thiazolone)]-dimethinemerocyanine, [2-(3-ethylbenzoxazole)] [4-(2-n-dodecylthio-5-thiazolone)]-dimethinemerocyanine, [2-(3-ethylbenzoxazole)] [4-(2-n-hexylthio-5-thiazolone)]-dimethinemerocyanine, [2-(3-ethylbenzoxazole)] [4-(2-n-heptylthio-5-thiazolone)]-dimethinemerocyanine, [2-(3-ethylbenzoxazole)] [4-(2-#c-phenylpropylthio-5-thiazolone)]-dimethinemerocyanine, [2-(1-ethyl-b -naphthathiazole)] [4-(2-ethylthio-5-thiazolone)]-b -methyldimethinemerocyanine, [2-(3-ethylbenzoxazole)] [4-(2-n-decylthio-5-thiazolone)]-dimethinemerocyanine, [2-(3-ethylbenzoxazole)] [4-(2-n-decylthio-5-thiazolone)]-b -methyldimethinemerocyanine, [2-(3-ethylbenzoxazole)] [4-2-n-decylthio-5-thiazolone)]-b -ethyldimethinemerocyanine, [2-(3-ethylbenzselazole)] [4-(2-n-heptylthio-5-thiazolone)]-dimethinemerocyanine, [2-(3-ethylbenzthiazole)] [4-(2-ethylthio-5-thiazolone)]-tetramethinemerocyanine and [2-(3-ethylbenzthiazole)] [4-(2-ethylthio-5-thiazolone)]-merocyanine are similarly prepared.  Specifications 133,034, [Class 98(2)], 369,616, 408,991, 447,092, 500,611, 500,826, 541,510, 541,511, 541,512, 541,513, 541,514, 541,515 and 552,368, [all in Group XX], are referred to.