GB1506848A - Stabilised ester group-containing compositions - Google Patents

Abstract

1506848 Isourea derivatives IMPERIAL CHEMICAL INDUSTRIES Ltd 16 June 1975 [29 July 1974] 33326/74 Heading C2C [Also in Division C3] An isourea or an isocyanate adduct thereof, e.g. of the formula R<SP>1</SP>-N(T)-C(OR<SP>3</SP>) =N-R<SP>2</SP>, wherein T represents hydrogen or a group of the formula R<SP>4</SP>NHCO and R<SP>1</SP>-R<SP>4</SP> each represents an optionally substituted hydrocarbyl radical, e.g. alkyl, cycloalkyl or aryl, may be prepared either by reacting a carbodiimide of the formula R<SP>1</SP>-N=C=N-R<SP>2</SP> with a compound of the formula R<SP>3</SP>OH and optionally reacting the product with an isocyanate of the formula R<SP>4</SP>NCO; or by phosgenating the corresponding (thio)urea and reacting the resulting chloroformamidine and/or carbonyl chloride with a metal alkoxide. Preferably R<SP>1</SP>, R<SP>2</SP> and R<SP>4</SP> are optionally substituted aryl radicals and R<SP>3</SP> is a C 1-4 alkyl radical optionally substituted with halogen, hydroxy, mercapto and amino groups, or an aryl radical optionally substituted with one or more electron withdrawing groups, e.g. NO 2 , CN, carboalkoxy, halogen and CF 3 . The compound may contain more than 1 isourea residue per molecule, e.g. R 3 may be a radical of the formula where X is an aliphatic residue and n is 1-7. In Examples 1 and 2 isoureas are prepared by reacting di-p-tolylcarbodiimide with either pnitrophenol, methanol or n- or t-butanol. In Examples 3-5 isoureas and isocyanate adducts of isoureas are prepared either (1) by first preparing 1,3-di-p-tolyl-2-methylisourea by heating p-tolyl isocyanate in the presence of 1 - phenyl - 3 - methylphospholene oxide and reacting the resulting carbodiimide with anhydrous CH 3 OH in the presence of Na; and reacting the resulting isourea with 4,4<SP>1</SP>-diisocyanatodiphenylmethane; or (2) by first reacting tolylene diisocyanate with either, methanol, benzyl alcohol, cyclohexanol or lauryl alcohol, then converting the NCO residues to carbodiimide groups using 1-phenyl-3-methylphospholene oxide, followed by reaction with anhydrous methanol in the presence of Na; or (3) by reacting bis-(3-isocyanato-4-methylphenyl)carbodiimide with anhydrous methanol and then adding Na and reacting the resulting isourea with 80/20 2,4-/2,6-tolylene diisocyanate.