Patent GB-942199-A (GB)
Title: Improvements in or relating to light-sensitive materials comprising polymeric azido or diazo compounds
IPC: G03F7/012
Filed: 1960-02-18
Abstract: The invention comprises compounds of general formulae:-<FORM:0942199/C2/1> <FORM:0942199/C2/2> wherein R1 and R2 represent hydrogen or alkyl, alkoxy, or carbalkoxy groups, D represents an azido group or a residue of a diazonium salt or diazosulphonate, X represents hydrogen or a methyl group and n represents a whole number greater than 1, which are prepared by reacting aromatic amines of the benzene or diphenylamine series substituted by at least one nitro group in the p-position with acrylic or methacrylic acid chloride, polymerising, reducing the nitro compounds to amine compounds and diazotising the amine groups to diazo compounds which may be in the salt form such as diazonium chloride, the zinc chloride double salt, boron fluoride or sulphonate. Alternatively, the aromatic amines of the benzene series are reacted with acrylic and methacrylic acid chlorides and nitro groups then introduced in the p position to the former amine group by nitric acid, and the compounds then polymerised, reduced and diazotised. The polymerisation may be in solution with free radical catalysts, and the reduction in the presence of Raney nickel. Examples describe the preparation of polymers of 2 - acroylamino hydroquinone - diethyl ether - 5 - diazonium chloride zinc double salt and diazo sulphonate 2 - acroylamino - 1 - methoxy - 4 - methyl phenyl - 5 - diazonium chloride, 3 - acroyl - amino - 1 - methylphenyl - 6 - diazonium chloride, 4 - acroyl amino - diphenylamine - 41 - diazonium chloride, 4 - and 3 - acroylamino-diphenylamine - 21 - carboxylic acid methyl ester - 41 - diazonium chloride, the azide from poly - 2 - acroylamino - hydroquinone - diethylether - 5 - diazonium chloride, 2 - methacroyl - amino - hydroquinone - diethyl ether - 5 - diazonium chloride - cadmium chloride double salt, and 2 - methacrylamino - hydroquinone - dimethylether - 5 - diazonium chloride.  The products are light-sensitive and may be coated from stabilised solution on supports such as foils of paper, metal, hydrolysed cellulose acetate, and polyamides for photomechanical reproduction.ALSO:Polymeric azido or diazo compounds of general formula: <FORM:0942199/C3/1> <FORM:0942199/C3/2> wherein R1 and R2 represent hydrogen, or alkyl, alkoxy or carbalkoxy groups; D represents an azido group or a residue of a diazonium salt or of a diazo-sulphonate; X represents hydrogen or a methyl group; n represents a whole number greater than 1 are prepared by reacting aromatic amines of the benzene or diphenylamine series substituted by at least one nitro group in the p-position with acrylic or methacrylic acid chloride, polymerizing, reducing the nitro compounds to amine compounds and diazotising the amine groups to diazo compounds which may be in the salt form such as diazonium chloride, the zinc chloride double salt, boron fluoride or sulphonate.  Alternatively the aromatic amines of the benzene series are reacted with acrylic and methacrylic acid chlorides and nitro groups then introduced in the p-position to the former amine group by nitric acid, and the compounds then polymerized reduced and diazotised.  The polymerization may be in a solution with catalysts such as, dibenzoyl and di-t-butyl peroxide, dicumene hydroperoxide or azobutyric acid dinitrile, and the reduction in the presence of a Raney nickel catalyst. Examples describe the preparation of polymers of 2-acroylamino hydroquinone-diethyl ether -5- diazonium chloride zinc double salt and diazo sulphonate, 2- acroylamino -1- methoxy -4- methylphenyl -5- diazonium chloride, 3-acroyl amino -1- methylphenyl -6- diazonium chloride, 4-acroyl amino - diphenylamine -4- diazonium chloride, 4- and 3- acroylamino-diphenylamine -21- carboxylic acid methyl ester -41- diazonium chloride, the azide from poly -2- acroylamino-hydroquinone - diethylether -5- diazonium chloride, 2-methacroyl-amino hydroquinone-diethyl ether -5- diazonium chloride-cadmium chloride double salt, and 2-methacroylamino-hydroquinone-dimethylether -5- diazonium chloride. The products are light-sensitive and may be coated from a stabilised solution on supports such as foils of paper, metal, hydrolysed cellulose acetate and polyamides for photo-mechanical reproduction. The solution may be based on water or an organic solvent, and may contain, as additional ingredients, gelatine, polyvinyl alcohol, polyvinyl pyrrolidone, methyl-cellulose, tragacanth, citric acid, aluminium sulphate, glycerol and triglycol.