Patent GB-1113264-A (GB)
Title: Production and use of polyhalopolyhydropolycyclicdi-carboxylic acid-alkanolamine-phosphorus compound reaction product
Inventor: CYBA HENRYK ANTONI
IPC: C07F9/32
Filed: 1965-07-16
Abstract: A phosphorus-containing polycondensate is obtained by reacting (i) an acid ester of orthophosphoric, pyrophosporic or thiophosphoric acid; or a mono- or dialkane or mono- or diaromatic phosphinic acid; or an alkane or aromatic phosphonic acid or acid ester thereof, with (ii) a polymer derived from (a) a polyhalopolyhydropolycycli dicarboxylic acid of the formula <FORM:1113264/C3/1> or <FORM:1113264/C3/2> wherein X is halogen, hydrogen or a C1-10 alkyl group, at least two X's being halogen; Y is halogen, hydrogen or a C1-10 alkyl group; m is 1-4, p is 0 or 1, and n is 1-4, or an anhydride or ester thereof, and (b) an alkanolamine having at least two hydroxy groups or at least two amino groups.  Preferred compounds (i) include acid orthophosphates, pyrophosphates and dithiophosphates of C6-20 alkanols or of oxyethylenated alcohols or alkylphenols. Suitable acids (a) may be obtained by Diels-Alder reaction between e.g. maleic, fumaric, itaconic, citraconic or glutaconic acid and e.g. hexachlorocyclopentadiene or the 1:2-, 1:5-, 1:2:3-, 1:2:3:4 and 1:2:3:4:5 polychlorocyclopentadienes or any conjugated diene followed by a second Diels-Alder reaction with a polyhalocycloalkadiene. Suitable alkanolamines (b) include N-alkyl-dialkanolamines.  In examples the reactants used are: bis-(pentaoxyethylenated nonyl phenol) orthophosphate, bis-(octaoxyethylenated nonyl phenol) orthophosphate, a mixed mono- and di-tridecyl orthophosphate, bis-(trioxypropylenated octylphenol) orthophosphate, bis - (pentaoxypropylenated dodecanol) orthophosphate, O-capryl-O-hexyl dithiophosphate, benzene phosphonic acid and monobenzene phosphonic acid; 5:6:7:8:9: 9 - hexachloro - 1:2:3:4:4a:5:8:8a-octahydro octahydro - 5:8 - methano - 2:3 - naphthalene dicarboxylic anhydride, chlorendic anhydride and the octyl ester of 5:6:7:8:9:9-hexachloro - 1:2:3:4:4a:5:8:8a - octahydro - 1:4:5:8 - dimethano - 2:3 - naphthalene dicarboxylic acid; and N-tallow-diethanolamine, N:N1 - dioctyl - N - hydroxyethylaminoethylethanolamine, N - decylaminopropyl - propanolamine and N - soya - diethanolamine. Uses: Lubricant additives, acting as extreme pressure additives, viscosity index improvers, pour point depressants, detergents, dispersants, peroxide decomposers, corrosion inhibitors; fire-resistant additives, anti-fouling paint additives, and oxidative and thermal stabilizers for organic compounds, including natural and synthetic oils and greases, plastics, coatings, paints, drying oils and textiles; insecticides.ALSO:Oils, fuels and greases may contain 0.01-20 wt. per cent of an additive obtained by reacting (i) an acid ester of orthophosphoric, pyrophosphoric or thiophosphoric acid, or a mono- or di-alkane- or aromatic phosphinic acid, or an alkane- or aromatic phosphonic acid or acid ester thereof with (ii) a polycondensate of (a) a polyhalopolyhydropolycyclic dicarboxylic acid of the formula <FORM:1113264/C4-C5/1> or <FORM:1113264/C4-C5/2> wherein each X and Y is halogen, hydrogen or a Cl-10 alkyl group, at least 2 X's being halogen. m is 1-4, p is 0 or 1 and n is 1-4 and (b) an alkanolamine having at least two hydroxy groups and/or at least two amino groups (see Division C3).  The additive functions as an extreme pressure additive, oxidation and corrosion inhibitor, antiwear agent, viscosity index improver, pour point depressant and dispersant. Suitable substrates include mineral, animal, marine and vegetable oils and synthetic oils, e.g. gasoline, naphtha, kerosene, jet fuel, diesel fuel, fuel oil, mineral lubricating oil, aliphatic esters, polyalkylene oxides, silicones, phosphoric and silicic acid esters and fluorocarbons, and also greases, e.g. metal base synthetic greases, whale grease, wool grease and greases from inedible fats, tallow and butchers' waste. The product compositions may be lubricating oils, transmission, hydraulic or industrial fluids, cutting, rolling, soluble or slushing oils, or drawing compounds.  In examples such additives are incorporated into a transmission oil, dioctyl sebacate lubricating oil, a white mineral lubricating oil, and a grease containing lithium stearate in a Mid-Continent lubricating oil.ALSO:Insecticide compositions contain as the active ingredient a reaction product of (i) an acid ester of orthophosphoric, pyrophosphoric or thiophosphoric acid, or a mono- or di-alkane- or aromatic phosphinic acid, or an alkane- or aromatic phosphomic acid or acid ester thereof with (ii) a polycondensate derived from (a) a polyhalopolyhydropolycyclic dicarboxylic acid of the formula <FORM:1113264/A5-A6/1> or <FORM:1113264/A5-A6/2> wherein each X and Y is halogen, hydrogen or a C1-10 alkyl group, at least 2 X's being halogen, m is 1-4, p is 0 or 1 and n is 1-4 and (b) an alkanolamine having at least 2 hydroxy groups and/or at least 2 amino groups.