The United States of America As Represented by the Secretary of

Arlen W Frank

Donald J Daigle

Russell M Kullman

George L Drake

The title compounds, having the formula (RO.sub.2 CNHCH.sub.2).sub.3 PY where Y=oxygen or sulfur, are prepared by reacting a tetrakis(N-carbalkoxylaminomethyl)phosphonium salt having the formula (RO.sub.2 CNHCH.sub.2).sub.4 P.sup.+ X.sup.- with ammonia or a primary or secondary amine, followed by an oxidizing or sulfurizing agent. The products, after methylolation with formaldehyde, are useful as finishing agents for imparting flame retardant properties to cotton fabrics.

Process for the preparation of tris(N-carbalkoxylaminomethyl)phosphine

The title compounds, having the formula (RO.sub.2 CNHCH.sub.2).sub.3 PY where Y=oxygen or sulfur, are prepared by reacting a tris(N-carbalkoxylaminomethyl)phosphine, having the formula (RO.sub.2 CNHCH.sub.2).sub.3 P, with an oxidizing or sulfurizing agent. The products, after methylolation with formaldehyde, are useful as finishing agents for imparting flame retardant properties to cotton fabrics.

Tris(N-carbalkoxylaminomethyl)phosphine oxides and sulfides

Tris(aminomethyl)phosphine oxide and its ternary salts, useful as catalysts for the chemical finishing of cotton, are prepared by the hydrolysis of tris(N-carbalkoxylaminomethyl)-phosphine oxides having the formula (RO.sub.2 CNHCH.sub.2).sub.3 PO with an alkali or alkaline earth in the presence of water, followed optionally by acidification.

Process for the preparation of tris(aminomethyl)phosphine oxide and its

Novel quaternary ureidomethyl phosphonium salts having the general formula ##STR1## are prepared by condensing a urea having the formula RNHC(O)NR'R' with a quaternary hydroxymethyl phosphonium salt having the formula (HOCH.sub.2).sub.4 P.sup.+ X.sup.- in a molar ratio of at least 2:1. The products, which are characterized by the absence of residual hydroxymethyl groups, are useful as finishing agents for imparting flame retardant properties to cotton fabrics.

Quaternary ureidomethyl phosphonium salts

Novel ternary salts of tris(aminomethyl) phosphines and their oxides having the formula (R.sub.2 NH.sup.+ CH.sub.2).sub.3 P(0).sub.n 3X.sup.-, wherein R is hydrogen, an alkylradical having from 1 to 6 carbon atoms, or an aryl radical n is an integer from 0 to 1, and X is a halogen, are prepared by the reaction of a hydrohalic acid, HX, with various nitrogen- and phosphorus-containing compounds including tris(aminomethyl)phosphines and their oxides, tris(N-carbalkoxylaminomethyl)phosphines oxides, and 1,3,5-triaza-7-phosphaadamantane and its 7-oxide.

Ternary salts of tris(aminomethyl)phosphines and their oxides

Novel ternary salts of tris(aminomethyl)phosphines and their oxides having the formula (R.sub.2 NH.sup.+ CH.sub.2).sub.3 P(O).sub.n 3X.sup.-, wherein R is hydrogen, an alkyl radical having from 1 to 6 carbon atoms or an aryl radical, n is an integer from 0 to 1, and X is a halogen, are prepared by the reaction of a hydrohalic acid, HX, with various nitrogen- and phosphorus-containing compounds including tris(aminomethyl)phosphines and their oxides, tris(N-carbalkoxylaminomethyl)phosphines oxides, and 1,3,5-triaza-7-phosphaadamantane and its 7-oxide.

Ternary salts of tris(aminomethyl)phosphines and their oxides prepared

The title compounds, having the formula (RO.sub.2 CNHCH.sub.2).sub.3 P, are prepared by reacting a quaternary phosphonium salt, having the formula (RO.sub.2 CNHCH.sub.2).sub.4 P.sup.+ X.sup.-, with a base, preferably one that is capable of reacting with and thereby inactivating the by-product formaldehyde or formaldehyde derivative. The products are useful as intermediates for the preparation of finishing agents that impart flame retardant properties to cotton fabrics.

Tris(N-carbalkoxylaminomethyl)phosphines

Novel quaternary phosphonium salts, bearing one or more carbamate groups attached through nitrogen, are prepared by condensing a hydroxymethyl phosphonium salt having the formula [R.sub.4-n P(CH.sub.2 OH).sub.n ].sup.+ X.sup.- with an alkyl carbamate having the formula NH.sub.2 CO.sub.2 R'. The products, which have the general formula [R.sub.4-n P(CH.sub.2 NHCO.sub.2 R').sub.n ].sup.+ X.sup.-, are useful as finishing agents for imparting flame retardant or durable press properties to cotton fabrics.

Quaternary phosphonium salts bearing carbamate groups

Novel ternary salts of tris(aminomethyl)phosphines and their oxides having the formula (R.sub.2 NH.sup.+ CH.sub.2).sub.3 P(0).sub.n 3X.sup.-, wherein R is hydrogen, an alkyl radical having from 1 to 6 carbon atoms or an aryl radical, n is an integer from 0 to 1, and X is a halogen, are prepared by the reaction of a hydrohalic acid, HX, with various nitrogen- and phosphorus-containing compounds including tris(aminomethyl)phosphines and their oxides, tris(N-carbalkoxylaminomethyl)phosphines oxides, and 1,3,5-triaza-7-phposphaadamantane and its 7-oxide.

Novel quaternary arylaminoalkyl phosphonium salts having the formula [(ArNHCHR).sub.4 P].sup.+X.sup.-, where R is a radical selected from the group consisting of hydrogen, alkyl and aryl, Ar is aryl, and X is halogen, are prepared by the reaction of primary aromatic amines with quaternary hydroxyalkyl phosphonium salts having the formula [(HOCHR).sub.4 P].sup.+X.sup.-, where R and X are similarly defined. The compounds of this invention are useful as flame retardant for cotton, plasticizers, lubricant additives, and surface-active agents.

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Slidell, LA, United States of America

Arlen W Frank