Patent GB-759409-A (GB)
Title: Improvements in photographic emulsions containing colour couplers
IPC: G03C7/388
Filed: 1954-04-20
Abstract: A mixture of 58.8 per cent n-butyl acrylate, 25.2 per cent styrene and 16 per cent methacrylamide is emulsion polymerized using a persulphate catalyst and sodium lauryl sulphate as the dispersing agent to give a hydrosol.  Reference is made also to copolymers of acrylic or methacrylic acid esters of aliphatic alcohols having up to 10 carbon atoms (e.g. methyl, ethyl, n-propyl, iso-propyl and n-butyl acrylates and methyl and ethyl methacrylates) with acrylonitrile, or styrene or substituted styrene such as o-methyl styrene, 2 : 4-dimethyl styrene, 2 : 4 : 5-trimethyl styrene or o-ethyl styrene, and to three component copolymers of acrylic or methacrylic acid esters with nitriles or styrene and acrylamide or methacrylamide or alkyl substituted derivatives of acrylamide or methacrylamide. Copolymers containing 70 per cent butyl acrylate and 30 per cent styrene or 70 per cent ethyl acrylate and 30 per cent acrylonitrile are specified.  Specifications 2562/13, [Class 98 (ii)], 524,154, 524,554, 524,555, 541,589, 547,064, 562,205, 733,119, 745,545 and 757,368, [all in Group XX], are referred to.  Reference has been directed by the Comptroller to Specification 674,752, [Group XX].ALSO:1 - Hydroxy - [21 - (211,411 - di - tert amylphenoxy) - 51 - carboxy] - 2 - naphthanilide is prepared by heating phenyl 1-hydroxy-2-naphthoate with 3-amino-4-(21,41-di-tert. amylphenoxy) benzoic acid.  1 - Hydroxy - 4 - [411 - (carboxymethyl)phenylazo] - [21 - (2111,4111 - di - tert. amylphenoxy - 5- carboxy] - 2 - naphthanilide is prepared by coupling the above hydroxynaphthanilide with diazotized p-aminophenylacetic acid.  2;4 - Dichloro - 3 - methyl - 6 - [31 - nitro - 61- (211;411 - di - tert. amylphenoxy)benzamido] phenol is prepared by heating a mixture of 2- amino - 4;6 - dichloro - 5 - methylphenol hydrochloride and 2-(21;41-di-tert. amylphenoxy)-5-nitrobenzoyl chloride in acetic acid with anhydrous sodium acetate.  This is then reduced to the corresponding amino compound with iron and acetic acid.  The resulting amine is added to 3;5-dichlorosulphonylbenzoyl chloride in dioxane to give 2;4 - dichloro - 3 - methyl - 6- {21 - [211;411 - di - tert. amylphenoxy] - 51 - [3111;5111 - (dichlorosulphonyl) benzamido]benzamido} phenol or the amine is stirred in a mixture of glacial acetic acid and anhydrous sodium acetate and 3;5-dicarbomethoxyphenylcarbamylvaleryl chloride added to give 2;4-dichloro3 - methyl - 6 - {21 - (211;411 - di - tert. amylphenoxy) - 51 - [o  - (3111;5111 - dicarbomethoxy phenylcarbamyl)valerylamido]benzamido}phenol.  3;5 - Dicarbomethoxyphenylcarbamylvaleric acid is prepared by refluxing a mixture of 5-amino-iso-phthalate and adipic anhydride in benzene. The corresponding acid chloride is made by treating the acid with thionyl chloride.  1 - Hydroxy - N - (p - nitro phenethyl) - 4- chloro - 2 - naphthamide is prepared by condensing p-nitro phenethylamine with phenyl 1- hydroxy - 4 - chloro - 2 - naphthoate. It is reduced with hydrogen and Raney nickel to the corresponding amine, which is then condensed in acetic acid and sodium acetate with 2-(21;41-di-tert. amyl phenoxy)-5-nitro benzoyl chloride to yield 1 - hydroxy - N - {41 - [211 - (2111;4111 - di-tert. amylphenoxy) - 511 - nitrobenzamido] phenethyl} - 4 - chloro - 2 - naphthamide. This is reduced with hydrogen and Raney nickel to the corresponding amine which is then condensed either with 3;5-dichlorosulphobenzoyl chloride to yield 1 - hydroxy - 4 - chloro - N - {p - [51- 311;511 - dichlorosulphobenzamido) - 21 -(2111;4111- di - tert. amylphenoxy)benzamido]phenethyl} - 2- 2 - naphthamide or with 3 - chlorosulphobenzoyl chloride to yield 1 - hydroxy - 4 - chloro - N- {p - [51 - (311 - chlorosulphobenzamido) - 21 - (2111; 4111 - di - tert. amylphenoxy)benzamido]phenethyl} - 2 - naphthamide.  1 - Phenyl - 3 - {31[211 - (2111;4111 - di - tert.- amylphenoxy) - 511 - (21111 - sulphobenzamido) benzamido]benzamido} - 5 - pyrazolone is prepared by reacting o-sulphobenzoic anhydride with 1 - phenyl - 3 - {31 - [211 - (2111;4111 - ditert. amylphenoxy) - 511 - aminobenzamido] benzamido}-5-pyrazolone in hot dry xylene.  1 - Phenyl - 3 - {31 - [211 - (2111;4111 - di - tert. amylphenoxy) - 511 - nitrobenzamido]benzamido}-5-pyrazolone is prepared by reacting 2-(21;41-di-tert. amylphenoxy) - 5 - nitrobenzoyl chloride with 1 - phenyl - 3 - (31 - aminobenzamido) - 5-pyrazolone in acetic acid and anhydrous sodium acetate.  The product may be reduced to the corresponding amine using iron and acetic acid.  1 - Phenyl - 3 - m - nitrobenzamido - 5 - pyrazolone is prepared by heating 1-phenyl-3-amino-5-pyrazolone with m-nitrobenzoyl chloride and ethyl oxalate on the steam bath.  The nitrogroup is reduced to an amino group using iron and acetic acid.  2 - (21;41 - Di - tert. amylphenoxy) - 5 - nitrobenzoic acid is prepared by reacting 2-chloro-5-nitrobenzoic acid with di-tert. amylphenol and potassium hydroxide pellets, and acidifying the reaction mixture with hydrochloric acid.  The acid chloride is obtained by treating the acid with thionyl chloride.  Specifications 2562/13, [Class 98 (ii)], 524,154, 524,554, 524,555, 541,589, 547,064, 562,205, [all in Group XX], 733,119, 745,545 and 757,368 are referred to.  Reference has been directed by the Comptroller to Specification 674,752, [Group XX].