Patent GB-811125-A (GB)
Title: Improvements in or relating to chelates and compositions containing them
IPC: C14C9/00
Filed: 1956-04-05
Abstract: Compositions for providing water-repellent coatings on porous or non-porous surfaces comprise alkoxy aluminium chelates of formula Al(R)x(OR1)y in which R1 represents a C1-4 alkyl group and R represents the anion of a bidentate chelating agent having its donor groups so situated with respect to each other that formation of a 5- or 6-membered chelate ring is possible, and containing at least one alkyl group in the form of a chain, preferably straight, of at least 12 carbon atoms and one acidic hydrogen, said anion being attached to aluminium through at least one oxygen atom and in which x and y each have a value not less than 0.5 and together total 3. Preferably one donor atom is oxygen and the other oxygen, nitrogen or sulphur. Suitable donor groups include phenolic and alcoholic hydroxyl, carbonyl, alkoxycarbonyl, primary amino, mercapto and thiocarbonyl. Suitable bidentate groups include b -diketo, b -keto-acyloxy, o-hydroxyaroyl, salicylideneimino, <FORM:0811125/III/1> or groups derived from o-aminophenols, esters of mercaptoacetic acid, and 8 - hydroxyquinolines.  b -Keto-esters, especially of long chain alkanols are preferred.  Specific examples of bidentate chelating agents are: octadecyl and dodecyl acetoacetate; ethyl stearoylacetate; the b -ketoacylates of long chain saturated fatty acid partial esters of polyhydric alcohols, e.g. the acetoacetic or benzoylacetic esters of distearin; dodecylglyoxal; salicylideneimines from long chain amines, e.g. N-dodecylsalicylaldimine; long chain salicylates, e.g. octadecyl salicylate; long chain diketones, e.g. stearoylacetone; and long chain esters of acetone dicarboxylic acid, e.g. dioctadecyl acetonedicarboxylate.  The chelates are preferably employed in conjunction with vehicles in the form of solutions or dispersions in organic media, e.g. toluene.  They may be blended with conventional film-forming clear and pigmented coating compositions, e.g. drying oil alkyd resin compositions, to form coating compositions which after baking or air drying give water-repellent coatings on porous or non-porous surfaces, e.g. wood or steel.  In Example (8) brick is treated with solutions of (octadecyl acetoacetato) aluminium diisopropoxide, (octadecyl benzoylacetato)0,5 aluminium (isopropoxide)2,5 and (octadecyl benzoylacetato)2,5 aluminium (isopropoxide)0,5, a paint prepared by ball-milling a toluene solution of (distearin acetoacetato)1,5 aluminium (isopropoxide)1,5 with titanium dioxide is used to treat brick; and cracks in concrete floors are filled with a composition comprising TiO2, a toluene solution of (distearin acetoacetato)1,5 aluminium (isopropoxide)1,5 and carbon black.  Specification 789,983, [Group IV (a)], is referred to.ALSO:The invention comprises alkoxy aluminium chelates of formula Al(R)x(OR1)y in which R1 represents a C1-4 alkyl group and R represents the anion of a bidentate chelating agent having its donor groups so situated with respect to each other that formation of a 5- or 6-membered chelate ring is possible, and containing at least one alkyl group in the form of a chain, preferably straight, of at least 12 carbon atoms and one acidic hydrogen, said anion being attached to aluminium through at least one oxygen atom and in which x and y each have a value not less than 0.5 and together total 3.  Preferably one donor atom is oxygen and the other oxygen, nitrogen or sulphur. Suitable donor groups include phenolic and alcoholic hydroxyl, carbonyl, alkoxycarbonyl, primary amino, mercapto and thiocarbonyl. Suitable bidentate groups include b -diketo, b -keto-acyloxy, o-hydroxyaroyl, salicylideneimino, <FORM:0811125/IV (b)/1> or groups derived from o-aminophenols, esters of mercaptoacetic acid, and 8-hydroxyquinolines.  b -keto-esters, especially of long chain alkanols, are preferred.  Specific examples of bidentate chelating agents are: octadecyl and dodecyl acetoacetate; ethyl stearoylacetate; the b -ketoacylates of long chain saturated fatty acid partial esters of polyhydric alcohols, e.g. the acetoacetic or benzoylacetic esters of distearin; dodecylglyoxal; salicylineneimines from long chain amines, e.g. N-dodecylsalicylaldimine; long chain salicylates, e.g. octadecyl salicylate; long chain diketones, e.g. stearoylacetone; and long chain esters of acetone dicarboxylic acid, e.g. dioctadecyl acetondicarboxylate.  The chelates are formed by heatin the aluminium alkoxide and the chelating agent at temperatures of at least 60 DEG  C., the specific temperature used being that required to remove the volatile alcohol formed from the reaction mixture possibly as a binary with the inert solvent which is preferably used, e.g. benzene, toluene, xylene, aliphatic petroleum fractions or dioxan.  The products have waterrepellent properties (see Groups III and VIII).  Examples describe the preparation of (octadecyl acetoacetato) aluminium diisopropoxide, N-(C16-18 alkyl) salicylaldimine aluminium diisopropoxide, (distearin acetoacetato) aluminium diisopropoxide, (octadecyl benzoylacetato) aluminium diisopropoxide, (octadecyl benzoylacetato)0.5 aluminium (isopropoxide)2.5, (octadecyl benzoylacetato)2.5 aluminium (isopropoxide)0.5, and (distearin acetoacetato)1.5 aluminium (isopropoxide)1.5.  Starting materials prepared are: octadecyl acetoacetate by ester interchange between octadecyl alcohol and ethyl acetoacetate; N - (C16-18 alkyl) salicylalddimine from a mixture of C16-18 alkyl fatty amines and salicylaldehyde; and distearin acetoacetate from distearin and ethyl acetoacetate.  Specification 789,983 is referred to.