Patent GB-675654-A (GB)
Title: Improvements in and relating to the manufacture of light-sensitive emulsions
Inventor: DORMAEL ANDRE EMILE VAN
IPC: G03C1/12
Filed: 1947-10-16
Abstract: 41 - Methoxy - 3 - amino - 4 - hydroxydiphenyl is prepared by reducing 41-methoxy-3-nitro-4-hydroxydiphenyl with stannous chloride and HCl at boiling temperature.  2 - Methyl - 5 - p - methoxyphenylbenzoxazole is prepared by refluxing 41-methoxy-3-amino-4-hydroxydiphenyl with acetic anhydride. 2-methyl-5-b -naphthylbenzoxazole is similarly prepared.  2 - (b  - ethyl : b  - anilinovinyl) - 5 - p - methoxybenzoxazole dimethylsulphate is prepared by fusing 2 - methyl - 5 - p - methoxyphenylbenzoxazole dimethylsulphate with S-methyl-isothiopropionanilide.  2 - Nitro - 5 - (b  - naphthyl) - phenol is prepared by nitrating p-(b -naphthyl)-phenol in acetic acid. 4-Methyl-31-nitro-41-hydroxydiphenyl is similarly prepared. 2-Amino-4-(b -naphthyl)-phenol is prepared by reducing 2 - nitro - 4 - (b  - naphthyl) - phenol with stannous chloride and HCl. 4-Methyl-31-amino-4-hydroxydiphenyl is similarly prepared.  2 - b  - Anilinovinyl - 5 - b  - naphthylbenzoxazole benzyl bromide is prepared by fusing 2-methyl - 5 - b  - naphthylbenzoxazole benzyl bromide with diphenylformamidine. 2-b -anilinovinyl - 5 - p - methoxyphenylbenzoxazole benzyl bromide is similarly prepared.  2 - Methyl - 5 - p - tolylbenzoxazole is prepared by heating 4 - methyl - 31 - amino - 41 - hydroxydiphenyl with acetyl chloride in benzene.  2 - (b  - Propyl : b  - anilinovinyl) - 5 - p - tolylbenzoxazole diethylsulphate is prepared by fusing 2 - methyl - 5 - p - tolylbenzoxazole diethylsulphate with ethylthiobutyrylisoanilide.  2 - Mercapto - 5 - b  - naphthylbenzoxazole is prepared by refluxing 2-amino-4-b -naphthylphenol with CS2 in alcohol containing KOH.  2 - Methylmercapto - 5 - b  - naphthylbenzoxazole is prepared by reacting 2-mercapto-5-b -naphthylbenzoxazole with dimethyl sulphate in alcoholic NaOH.ALSO:3 : 31 - Dimethyl - 9 - ethyl - 5 : 51 - di - p - methoxyphenyloxacarbocyanine iodide is prepared by condensing together in pyridine 2-(b -ethyl : b  - anilinovinyl) - 5 - p - methoxyphenylbenzoxazole dimethylsulphate and 2-methyl-5-p-methoxyphenylbenzoxazole dimethylsulphate and treating with aqueous KI solution.  3 : 31 - Dibenzyl - 5 : 51 - di - p - methoxyphenyloxacarbocyanine bromide is prepared by reacting 2 - methyl - 5 - p - methoxyphenylbenzoxazole benzyl bromide with ethyl orthoformate in acetic anhydride.  3 - Benzyl - 31 - ethyl - 5 - b  - naphthyloxathiazolinocarbocyanine iodide is prepared by condensing 2 - (b  - anilinovinyl) - 5 - b  - naphthylbenzoxazole benzyl bromide with 2-methylthiazoline ethyl bromide in pyridine, and treating with aqueous KI solution. 3 : 31-Dibenzyl - 41 - methyl - 5 - b  - naphthyloxathiazolocarbocyanine bromide is similarly prepared.  3 : 31 - Diethyl - 9 - n - propyl - 5 : 51 - di - p - tolyloxacarbocyanine ethylsulphate is prepared by condensing 2-(b -n-propyl : b -anilinovinyl)-5-p-tolylbenzoxazole diethylsulphate and 2-methyl-5-p-tolylbenzoxazole diethylsulphate in pyridine.  11 : 3 - Diethyl - 5 - p - tolyloxa - 21 - cyanine iodide is prepared by condensing 2-methyl-5-p-tolylbenzoxazole diethylsulphate and 2-methyl-mercaptoquinoline ethyl iodide in pyridine.  A hemicyanine dye is prepared by fusing together 2-methyl-5-p-tolylbenzoxazole diethylsulphate, ethyl orthoformate, and p-phenylenediamine, and converting to the iodide.  A complex merocyanine dye is prepared by fusing together 5-[(1-ethylquinolylidene)-ethylidene] - 3 - allylrhodanine, 2 - methyl - 5 - p - methoxyphenylbenzoxazole, and methyl p-toluenesulphonate and converting to the iodide.  3 - Benzyl - 5 - p - methoxyphenyl - 41 - p - tolyl - 10 - acetyloxaoxodiazolocarbocyanine base is prepared by condensing 2-b -anilinovinyl-5-p-methoxyphenylbenzoxazole benzyl bromide and 2-acetylmethyl-4-p-tolyl-1 : 3 : 5-oxodiazole in acetic anhydride containing triethylamine.  5 - [(3 - Benzyl - 5 - b  - naphthylbenzoxazolylidene) - ethylidene] - 3 - allylrhodanine is prepared by refluxing together 2-(b -anilinovinyl)-5-(b -naphthyl)-benzoxazole benzyl bromide, 3-allylrhodanine, acetic anhydride, and sodium acetate.  2 - p - Dimethylaminostyryl - 3 - ethyl - 5 - b  - naphthylbenzoxazole ethylsulphate is prepared by boiling together 2-methyl-5-(b -naphthyl)-benzoxazole diethylsulphate and p-dimethylaminobenzaldehyde in acetic anhydride.  3 : 31 - Dibenzyl - 5 - b  - naphthyl - 9 - ethoxyoxathiacarbocyanine bromide is prepared by heating together 2-(b -ethoxy : b -vinyl)-benzthiazole benzylethyl sulphate, 2 - methylmercapto - 5 - b  - naphthylbenzoxazole benzyl p-toluenesulphonate, acetic anhydride, and triethylamine, and treating with aqueous KBr solution.