Patent GB-919267-A (GB)
Title: Improvements in or relating to the manufacture of substituted organic phosphine derivatives
Inventor: COATES HAROLD
IPC: C08G79/02
Filed: 1958-07-15
Abstract: A condensation product containing one or more <FORM:0919267/IV(a)/1> linkages is obtained by reacting a phosphine RnPH3-n with formaldehyde and an amido compound containing at least one of the groups: <FORM:0919267/IV(a)/2> or with a methylol derivative of such an amido compound, R being an alkyl, aralkyl, aryl or heterocyclic radical and n being 0, 1 or 2.  Specified amido compounds are urea, dicyandiamide, guanidine, biuret, semi-carbazide and melamine. Specified phosphines are phosphine itself and methyl-, ethyl-, butyl-, dibutyl-, and phenylphosphines.  When n is 0 or 1 the products may be polymeric depending on the reactants and reaction conditions.  The reaction may be effected at room temperature and suitably under an inert atmosphere, e.g. N2 or CO2. Water or other inert solvent may be used as reaction medium and a tertiary organic base may also be added.  The pH value may be adjusted by adding an acid or base.  Examples are given for the production of viscous liquids by reacting phosphine with formaldehyde and urea, guanidine sulphate and dicyandiamide respectively and by reacting di-n-butyl phosphine with formaldehyde and hexamethylol melamine.  The products are useful in the manufacture of thermosetting resins and in the flame-proofing of textiles, and in an example the product obtained from phosphine, formaldehyde and urea is dissolved in water and a solution of a partially methylated trimethylol melamine containing mono ammonium phosphate as curing catalyst is added. A piece of white cotton denim cloth is padded in the solution and the treated cloth dried at 95 DEG -100 DEG C. for 10 minutes and the resin on the cloth cured by baking the cloth at 145 DEG C. for 5 minutes. The cloth is finally washed with dilute hot soda ash solution containing a little hydrogen peroxide and then rinsed in cold water, the treated cloth being flame resistant.  Specification 854,182 is referred to.ALSO:A condensation product containing one or more <FORM:0919267/IV (b)/1> linkages is obtained by reacting a phosphine RnPH3-n with formaldehyde and an amido compound containing at least one of the groups:- <FORM:0919267/IV (b)/2> or with a methylol derivative of such an amido compound, R being an alkyl, aralkyl, aryl or heterocyclic radical and n being 0, 1 or 2.  Specified amido compounds are urea, dicyandiamide, guanidine, biuret, semicarbazide and melamine.  The reactio may be carried out at room temperature and may be represented as follows:- <FORM:0919267/IV (b)/3> where N is an amido nitrogen and n is 0, 1 or 2.  When n is 2 the products are in general monomeric whereas when n is 0 or 1 the products may be polymeric depending on the reactants and reaction conditions.  The reaction may be effected by adding the phosphine gradually, through a gas distributer if gaseous, to a vigorously stirred solution of the amido compound and formaldehyde, or of the methylolamido compound, under an inert atmosphere such as nitrogen or carbon dioxide and the pH value may be adjusted by adding an acid or base.  Water or other inert solvent may be used as reaction medium and a tertiary organic base may be added to the reaction mixture.  Specified phosphines are phosphine itself and methyl-, ethyl-, butyl-, dibutyl-, and phenyl-phosphines. Examples are given for the reaction of phosphine with formaldehyde and urea, guanidine sulphate, and dicyandiamide respectively and of di-n-butyl phosphine with formaldehyde and hexamethylolmelamine, the product in each case being a viscous liquid.  The products are useful in the manufacture of thermosetting resins and in the flame-proofing of textiles (see Groups IV(a) and VIII).  Specification 854,182 is referred to.