Patent GB-852646-A (GB)
Title: Dyed polyester resins and processes for their manufacture
IPC: C08G63/68
Filed: 1957-12-17
Abstract: Dyed polyester resins are made by incorporating into the polyesterification mixture a dyestuff containing one or more carboxylic and/or hydroxylic and/or amino groups.  In examples, lacquers, some of which may be admixed with melamine or urea resins, are made by reacting together in the presence of xylene (a) phthalic anhydride (b) glycerol or a mixture thereof with pentaerythritol, (c) coconut oil fatty acids, distilled C10-C18 fatty acids, lacquer soya oil or distilled linseed fatty acids (d) a dyestuff as specified below and, optionally, (e) bezoic acid; the dyestuff being (1) <FORM:0852646/IV(a)/1> (2) the reaction product of epichlorhydrin and <FORM:0852646/IV(a)/2> (3) and (4) the product obtained by reacting a metal complex wool dyestuff with epichlorhydrin or ethylene chlorohydrin to connect the sulphonamide group into the grouping <FORM:0852646/IV(a)/3> or <FORM:0852646/IV(a)/4> (5) <FORM:0852646/IV(a)/5> (6) <FORM:0852646/IV(a)/6> (7) and (8) <FORM:0852646/IV(a)/7) (11) <FORM:0852646/IV(a)/8> (12) <FORM:0852646/IV(a)/9> (14) <FORM:0852646/IV(a)/100) (15) <FORM:0852646/IV(a)/111> (16) <FORM:0852646/IV(a)/122> (18) <FORM:0852646/IV(a)/133> (19) <FORM:0852646/IV(a)/144> (21) <FORM:0852646/IV(a)/155> (22) <FORM:0852646/IV(a)/166> (23) <FORM:0852646/IV(a)/177> (24) <FORM:0852646/IV(a)/188> (25) <FORM:0852646/IV(a)/199> (26) A product made by converting an ester containing free hydroxyl groups and prepared from 2 mols of 3-nitrophthalic acid and 8 mols of glycerine into a nigrosine carboxylic acid esterified with glycerine;  (27) <FORM:0852646/IV(a)/200> (28) <FORM:0852646/IV(a)/211> (29) Bismark brown.  In further examples (9), (10), (13) and (17), unsaturated polyesters were made by reacting maleic anhydride, phthalic anhydride, the diazo dyestuff of Examples 7 or 16, propylene glycol and, optionally, ethylene glycol; the unsaturated polyesters were dissolved in styrene and the solutions hardened with a peroxide catalyst, possible with the addition of cobalt naphthenate as an accelerator.  In Example (20) a polyester for use in admixture with dibutyl phthalate for plasticizing polyvinyl chloride, was made by reacting adipic acid, diethylene glycol and the dyestuff of Example 7.ALSO:Dyestuffs containing reactive carboxylic, amino and/or hydroxyl groups are chemically incorporated into polyester resins. In examples such dyestuffs are prepared as follows: (1) p-oxyazo benzene is reacted with epichlorhydrin in the presence of Na OH to give:  <FORM:0852646/IV (c)/1> (2) diazotized p-anisidine is coupled with a -naphthol to give:  <FORM:0852646/IV (c)/2> which is reacted with epichlorhydrin in the presence of Na OH; (3) a yellowish brown neutraldyeing 2 : 1 metal complex wool dyestuff is reacted with epichlorhydrin to convert the sulphonamide group into the grouping: <FORM:0852646/IV (c)/3> (4) a scarlet red neutral-dyeing 2 : 1 metal complex is heated with ethylene chlorhydrin and soda solution to convert the sulphonamide group into the grouping:  <FORM:0852646/IV (c)/4> (5) 1-oxy- 4- benzoylaminoanthraquinone is reacted with epichlorhydrin to give: (12) Tetrazotized benzidine is coupled with 2, 3- oxynaphthoic aci to give:  <FORM:0852646/IV (c)/5> (6) 1, 4-diaminoanthraquinone is reacted with ethylene chlorhydrin in the presence of aqueous alkali carbonate to give:  <FORM:0852646/IV (c)/6> (7) Diazotized anthranilic acid is coupled with b -oxynaphthoic acid to give:  <FORM:0852646/IV (c)/7> (11) Diazotized anthranilic acid is coupled with salicylic acid to give: <FORM:0852646/IV (c)/8> (14) Diazotized anthranilic acid is coupled with b -naphthol to give:  <FORM:0852646/IV (c)/9> (15) The dyestuff obtained by coupling diazotized aniline with salicylic acid is reacted with sodium chloroacetate to give:  <FORM:0852646/IV (c)/100> (16) The dyestuff of Example 14 is reacted with sodium chloroacetate to give:  <FORM:0852646/IV (c)/111> (18) Diazotized p-aminobenzoic acid is coupled with phenol and the product reacted in alkaline medium with chloroacetic acid to give:  <FORM:0852646/IV (c)/122> (21) Diazotized 4- chloro -2- nitroaniline is coupled with salicyclic acid to give:  <FORM:0852646/IV (c)/133> (24) 4- Chloro -2- nitraniline, 3- aminophthalic and quinone are heated to give: <FORM:0852646/IV (c)/144> (26) An ester containing free hydroxyl prepared from 2 mols. of 3- nitrophthalic acid and 8 mols. of glycerine, was converted into a nigrosine carboxylic acid esterified with glycerine by means of 4 mols of aniline, 1 mol of aniline hydrochloride and iron powder; (27) 1 : 4- Diaminoanthraquinone is reacted with phthalic anhydride to give:  <FORM:0852646/IV (c)/155> (28) 1: 4- Diamino -2- methoxyanthraquinone is reacted with phthalic anhydride to give:  <FORM:0852646/IV (c)/166>