Patent GB-971907-A (GB)
Title: Ionic organic compounds containing boron or aluminium
IPC: C08F2/24
Filed: 1960-11-15
Abstract: <FORM:0971907/C1/1> The invention comprises condensed organometallic betaine esters of the formula <FORM:0971907/C1/2> wherein a is quaternary nitrogen or phosphorus, M is tetracovalent boron or aluminium, n is 1 to 6, m is 1 to 25, R is an aliphatic radical with 1 to 20 carbon atoms, phenyl, benzyl, (Cm H2nO)mM\sKR13 or [(CnH2nO)mHR13]\sKY\sJ where Y is a cation, R1 is hydrogen, alkoxy with 1 to 6 carbon atoms, a phenyl, phenoxy, (Cn H2nO)mCl\sJR3 or [(CnH2nO)mAR3]\sJX\sK where X is an anion, or one or more pairs of the R and R1 radicals together with the Cl and M atoms are represented by the general formulae <FORM:0971907/C1/3> The invention also comprises 2,2-dimethoxy-6-methyl -6- octadecyl-1, 3-dioxa -2- bora -6- aracyl co-octaine betaine, 2-(benzyl-"coco" -b - hydroxymethylammonio) ethoxy-tri -2- propoxy aluminate betaine and 2-(tris-(2-hydroxylethyl)-ammonio) ethoxy dimethoxy-hydroborate betaine. These betaines are prepared by reacting a compound of formula <FORM:0971907/C1/4> with a compound of formula <FORM:0971907/C1/5> the symbols being the same as above, to form an unstable metathesis product ((3) on the drawing) which gives a simple condensation product (4) or its salt adduct (5). Inter- and intra-molecular condensation may occur to give a linear polymer (6) or a product (10) repectively. On further condensation, linear polymer (6) is converted into a branched polymer (7) or (8) or a macrocycle (9). Product (10) on further condensation may give products (11), (12) and (13) or may form salt adducts (14) and (15). However, salt adducts (5), (14) and (15) are only formed when the salt is not separated from the metathesis product (3), but otherwise there appears to be no reliable guide as to the nature of the product formed. The preferred reactants are the onium compounds listed in Table A and the metalate compounds listed in Table B. X\sK is preferably halide, nitrate, phosphate or trifluoroacetate and Y\sJ is alkali or alkaline earth metal. The preferred reaction medium is an alcohol with 1 to 6 carbon atoms.ALSO:<FORM:0971907/C3/1> Various condensation polymers of nitrogen or phosphorus and boron or aluminium (cf e.g. (6)-(9) (12) and (16)-(24) of the drawings) are obtained by reacting an onium salt of formula <FORM:0971907/C3/2> with a metalate salt of formula <FORM:0971907/C3/3> wherein Q is quaternary nitrogen or phosphorus, M is tetracovalent boron or aluminium, n is 1-6, m is 1-25, R is an aliphatic radical with 1 to 20 carbon atoms, phenyl or benzyl, R1 is hydrogen, alkoxy with 1-6 carbon atoms, phenyl or phenoxy, X- is an anion and Y+ is a cation to give a metathesis product (3) which condenses to (4). If this product (4) or another simple condensation product (6), (10) or (11) is heated to constant weight from 125-250 DEG C. one of the above-mentioned polymers is obtained. Polymerized 2,2-dimethoxy-6, 6-bis-(2-hydroxyethyl) -2- bora-6-1, 3 dioxacyclo-octane betaine (10) and polymerized 1-hydroxymethyl -4- methoxy -1-phospha -4- bora-3, 5, 8-trioxabicyclo [2,2,2] octaine betaine are claimed per se. Various polymers are prepared in Examples III, VI, XI, XIV, XXI, XXIX, XXXII, XXXIII, XXXVII, XXXIX, XL and XLII.ALSO:Aqueous solutions of the various condensation polymers of boron or aluminium and nitrogen or phosphorus (cf. e.g. (6)-(9), 12 and (16)-(24) of the drawing), obtained by reacting an onium salt with a metalate salt and heating to 125-250  DEG C., are used as protective coatings for metal, e.g. pipes and nails.  In Example 43, nails are dipped in an aqueous polymer solution of formula:  <FORM:0971907/B1-B2/1> <FORM:0971907/B1-B2/2> <FORM:0971907/B1-B2/3>ALSO:<FORM:0971907/A5-A6/1> Condensation products of ammonium salts with borate salts (of products (6) and (10) of the drawing) are used in insecticide compositions.  In Example 45, the condensate of formula <FORM:0971907/A5-A6/2> is admixed with diatomaceous earth, pyrophylite and a dispersant and used as an aqueous suspension.