Patent GB-1056230-A (GB)
Title: Organic polyisocyanates and polyurethanes prepared therefrom
Inventor: HUDSON GEORGE ALLEN
IPC: C08G18/00
Filed: 1964-12-22
Abstract: The invention comprises mixtures of polyaryl polyalkylene polyisocyanates, the molecules of which contain alternate aryl and alkylene groups terminating in aryl groups, the isocyanate groups present being bonded to aryl groups, and some of them being reacted with a monofunctional compound containing at least 2 carbon atoms and only one active hydrogen atom.  Of particular interest are compounds of the Formula <FORM:1056230/C2/1> in which m is 1-3, n is 0.5 to 2.0, X is hydrogen, C1-C18 alkyl, C1-C18 alkoxy, halogen or nitro and R is alkylene, and in which 2-50% of the -NCO groups have been reacted with a monohydric alcohol having 2-20 carbon atoms. Other monofunctional compounds which may be used are monocarboxylic acids. The starting mixtures of polyaryl polyalkylene polyisocyanates may be prepared by reacting an aromatic amine with an aldehyde or ketone and reacting the products with phosgene to give the corresponding isocyanates. Suitable aryl amines are, for example, aniline, chloro- or bromo-aniline, o-, m- and p-toluidine, o-, m-and p-xylidine, o-, m- and p-xenylamines, methoxyaniline, nitroaniline, 2,4 - tolylenediamine and 2,6-tolylene diamine.  Suitable aldehydes and ketones are, for example, form-aldehyde, acetaldehyde, propionaldehyde, butyr-aldehyde, benzaldehyde, cyclohexanealdehyde, acetone, methyl ethyl ketone, methyl-n-propyl ketone, diethyl ketone, hexanone-2, hexanone-3, di-n-propyl ketone and cyclohexanone.ALSO:Polyaryl polyalkylene polyisocyanates, the molecules of which contain alternate aryl and alkylene groups terminating in aryl groups, the -NCO groups present in the molecule being bonded to aryl groups, and in which some of the -NCO groups are reacted with a monofunctional compound containing at least 2 carbon atoms are used in the formation of polyurethanes. Of particular use as starting materials for producing the urethanes are the polyarylpolyalkylene polyisocyanates of <FORM:1056230/C3/1> in which m is 1-3, n is 0.5-2.0, X is hydrogen, C1-C18 alkyl, C1-C18 alkoxy, halogen or nitro and R is alkylene and in which 2-50% of the -NCO groups have been reacted with a monofunctional compound, especially a C2-C20 monohydric alcohol.  Instead of an alcohol a monocarboxylic acid may be used.  The polyisocyanates so obtained are reacted with compounds containing at least two active hydrogen-containing groups, e.g. hydroxyl polyesters; polyhydric polyalkylene ethers; polyhydric polythioethers; polyacetals, aliphatic polyols, including alkane, alkene and alkyne diols, triols and tetrols, aliphatic polythiols and polyamines. The polyhydric polyalkylene ethers used may be the condensation products of an alkylene oxide using a suitable initiator, e.g. water, a polyhydric alcohol; an amine preferably having 2-8 amino groups and phosphorous acids.  The compounds obtained by condensing a mixture of phosphorous pentoxide, water and an alkylene oxide are advantageous since they impart a flame-retarding effect to the product.  The phosphorous compounds may also contain nitrogen and typical of such compounds are those of formula <FORM:1056230/C3/2> in which R is alkyl or phenyl and R1 is alkylene. Any of the compounds containing at least two active hydrogen-containing groups may be additionally substituted by halogen, nitro, alkoxy, carbalkoxy, dialkylamino, mercapto, carbonyl, thiocarbonyl, phosphoryl and phosphato groups.  Any other isocyanate may be mixed with the polyisocyanates used as starting materials, the preferred material being the commercially available mixture of toluylene diisocyanates.  Cellular polyurethanes may be obtained by reacting the polyisocyanate with the active hydrogen-containing compound in the presence of a blowing agent.  In the preparation of cellular polyurethanes other additives, e.g. emulsifiers, foam stabilizers, colouring agents and fillers may be present. Suitable emulsifiers are, for example, sulphonated castor oil and preferred foam stabilizers are silicone oils.