Patent GB-793292-A (GB)
Title: Photographic elements containing ultraviolet absorbing compounds
IPC: C08F8/14
Filed: 1956-05-16
Abstract: Compounds of the general formula <FORM:0793292/IV (b)/1> wherein R and R1 are alkyl, aryl or substituted aryl groups and R6 is an amino-acyl group, are prepared by condensing a hydrazine of the formula H2N-NRR1 with the appropriate aromatic aldehyde.  The preparations of the a -methyl-a -phenylhydrazones of p-b -hydroxyethoxybenzaldehyde and p-aminobenzaldehyde are described, the latter by reduction of the first-formed corresponding nitro compound. Compounds of the general formula <FORM:0793292/IV (b)/2> wherein R2 is an acyl group are prepared by heating a dihydroxybenzophenone such as 1-benzoyl-2,4-dihydroxybenzene with ethylenechlorohydrin. Compounds having one of the general formul  <FORM:0793292/IV (b)/3> or <FORM:0793292/IV (b)/4> wherein R3 and R4 are aryl or substituted aryl groups or R4 is alkyl, provided that at least one of R3 and R4 is aryl containing a hydroxyalkyl radical, and R5 is an aryl group, are prepared by the method of Specification 770,494, by reacting an aldehyde (R3CHO or R5CHO) with the appropriate thiazolidone having 2 hydrogen atoms in the 5-position.  5-Benzal-3-(p-b -hydroxyethylphenyl) - 2 - phenylimino - 4 - thiazolidone is so prepared.  5-p- and m-(b -Hydroxyethoxy) benzal - 3 - phenyl - 2 - phenylimino - 4 - thiazolidone and the corresponding 3-ethyl-5-p-compound are referred to.  3 - (p - b  - Hydroxyethylphenyl) - 2 - phenylimino - 4 - thiazolidone is prepared by refluxing 1 - p - b  - hydroxyethylphenyl - 3 - phenylthiourea with ethyl chloroacetate.  1 - p - b  - Hydroxyethylphenyl - 3 - phenylthiourea is prepared by treating p-b -hydroxyethylaniline in benzene with phenyl isothiocyanate. Specifications 351,508 and 376,479, [both in Group IV], are also referred to.ALSO:Polymerized mono-ethylenically unsaturated compounds having free carboxylic acid halide or anhydride groups, are reacted with compounds containing hydroxyalkyl or aminoaryl groups, which compounds have one of the following formul  <FORM:0793292/IV (a)/1> and <FORM:0793292/IV (a)/2> wherein R, R1 and R4 are alkyl, aryl o substituted aryl groups, R2 and R5 are aryl groups, R3 is an aryl or substituted aryl group (provided that at least one of R3 or R4 contains a hydroxyalkyl radical) and R6 is an amino-aryl group.  Suitable polymers are interpolymers of maleic anhydride with styrene, vinyl acetate, vinyl chloride, alkyl vinyl ethers, acrylic acid or methacrylic acid, and the corresponding interpolymers of maleyl and fumaryl halides with such vinyl compounds, and polyacrylyl halides and anhydrides including polymethacrylyl chloride and polymethacrylic anhydride. The interpolymers of maleic anhydride, citraconic anhydride, phenyl maleic anhydride, fumaryl halides or maleyl halides with vinyl compounds as described in Specification 376,479, [Group IV], and polymers of acrylic or a -methacrylic halides and copolymers of these with vinyl acetate, styrene, ethyl acrylate or acrylonitrile, as described in Specification 351,508, [Group IV], may be used. Examples are given of the reaction of styrene/maleic anhydride interpolymer with p-b -hydroxyethoxybenzaldehyde-a -methyl - a  - phenylhydrazone, 2 - hydroxy - 4 - b -hydroxyethoxybenzophenone or 5-benzal-3-p - b  - (ydroxyethoxyphenyl - 2 - phenylimino - 4-thiazolidone, and of the reaction of polyacrylic anhydride with 3-ethyl (or 3-phenyl)-5 - p - (b  - hydroxyethoxy) benzal - 2 - phenylimino - 4 - thiazolidone, 5 - m - (b  - hydroxyethoxy) benzal - 3 - phenyl - 2 - phenylimino - 4 - thiazolidone, 5 - benzal - 3 - p - b  - hydroxyethoxyphenyl - 2 - phenylimino - 4 - thiazolidone, p - aminobenzaldehyde - a  - methyl - a  - phenylhydrazone or 3 - b  - aminoethyl - 5 - benzal - thiazolidine - 2:4 - dione.  In one example a copolymer of acrylic acid and 3-(b -acrylamidoethyl) - 5 - anisalthiazolidine - 2:4 - dione is prepared by reacting polyacrylic anhydride with 3-aminoethyl-thiazolidine-2:4-dione and condensing the product with anisaldehyde.  Specification 770,494, [Group IV (b)], also is referred to.