Stauffer Chemical Company

Akzo America Inc.

Thomas A Hardy

Edward N Walsh

Fred Jaffe

Sophia Y Liu

There are disclosed multiphosphorus-containing compounds comprising phosphonate-containing or phosphate-containing phosphate esters. The compounds can be prepared by: (a) reacting a phosphonate-containing or phosphate-containing alcohol with phosphorus pentoxide following by reaction with an epoxide, (b) reacting a phosphonate-containing or phosphate-containing alcohol with a phosphorus oxyhalide, hydrolyzing any phosphorus halogen bonds and then reacting with the resulting phosphoric acid derivative with an epoxide, (c) transesterifying a phosphonate-containing or phosphate-containing alcohol with a dialkyl phosphite, oxidizing the resulting compound to yield a phosphoric acid derivative and reacting the phosphoric acid derivative with an epoxide. The compounds are useful as flame retardant additives for polyurethanes and textiles.

Phosphate-containing and phosphonate-containing phosphate esters

There are disclosed novel phosphorus-containing compounds including and derived from hydrogen phosphonates. The compounds of the present invention can be prepared by reacting a hydrogen phosphonate with: (a) an ethylene derivative in a Michael reaction, (b) an amine or amide and formaldehyde in a Mannich reaction, (c) an aldehyde or ketone, (d) a halogen, (e) carbon tetrachloride and an alkylamine, and (f) carbon tetrachloride and a hydroxyphosphonate. Halophosphonates produced according to procedure (d) can also be used in reactions with (a) alkylamines and (b) hydroxyphosphonates or epoxides to produce the compounds of the present invention.

Phosphate and phosphonate compounds including and derived from phosphate

There are disclosed multiphosphorus-containing compounds comprising phosphonate-containing or phosphate-containing phosphate esters. The compounds can be prepared by: (a) reacting a phosphonate-containing or phosphate-containing alcohol with phosphorus pentoxide following by reaction with an epoxide, (b) reacting a phosphonate-containing or phosphate-containing alcohol with a phosphorus oxyhalide, hydrolyzing any phosphorus halogen bonds and then reacting the resulting phosphoric acid derivative with an epoxide, (c) transesterifying a phosphonate-containing or phosphate-containing alcohol with a dialkyl phosphite, oxidizing the resulting compound to yield a phosphoric acid derivative and reacting the phosphoric acid derivative with an epoxide. The compounds are useful as flame retardant additives for polyurethanes and textiles.

There are disclosed novel phosphorous-containing compounds including and derived from hydrogen phosphonates. The compounds of the present invention can be prepared by reacting a hydrogen phosphonate with: (a) an ethylene derivative in a Michael reaction, (b) an amine or amide and formaldehyde in a Mannich reaction, (c) an aldehyde or ketone, (d) a halogen, (e) carbon tetrachloride and an alkylamine, and (f) carbon tetrachloride and a hydroxyphosphate. Halophosphonates produced according to procedure (d) can also be used in reactions with (a) alkylamines and (b) hydroxyphosphonates or epoxides to produce the compounds of the present invention.

Phosphate and phosphonate compounds

There are disclosed novel phosphorous-containing compounds including and derived from hydrogen phosphonates. The compounds of the present invention can be prepared by reacting a hydrogen phosphonate with: (a) an ethylene derivative in a Michael reaction, (b) an amine or amide and formaldehyde in a Mannich reaction, (c) an aldehyde or ketone, (d) a halogen, (e) carbon tetrachloride and an alkylamine, and (f) carbon tetrachloride and a hydroxyphosphonate. Halophosphonates produced according to procedure (d) can also be used in reactions with (a) alkylamines and (b) hydroxyphosphonates or epoxides to produce the compounds of the present invention.

Phosphonate containing phosphonates

Flame retardant oligomeric phosphate ester compositions having the structural formula: ##STR1## are prepared, wherein R is C.sub.1 -C.sub.10 alkyl or haloalkyl, R.sup.1 and R.sup.2 can be the same or different and are hydrogen, C.sub.1 -C.sub.10 alkyl or haloalkyl and n is an integer from zero to about 10. The method of preparing the compositions comprises reacting P.sub.2 O.sub.5 with a trialkyl or tris(haloalkyl)phosphate in the presence of about 0.01% to about 5% of a phosphite at a temperature from about 0.degree.-200.degree. C. A polyphosphate ester having P--O--P bonds is formed which is then reacted with an epoxide to yield the oligomeric phosphate ester flame retardant compositions. Alternatively, a method of preparing similar compositions comprises reacting P.sub.2 O.sub.5 with a trialkyl or tris (haloalkyl)phosphite at a temperature from about 0.degree. C. to about 200.degree. C. A mixed polyphosphate-polyphosphite ester having P--O--P bonds is formed which is then oxidized to yield a polyphosphate having P--O--P bonds; which is then reacted with an epoxide to yield the oligomeric phosphate ester flame retardant compositions.

Polyurethane foam having a flame retardant oligomeric phosphate ester

A process for the preparation of organic phosphate-phosphonates comprises the steps of reacting an organic acylating agent with an organophosphite triester to form an intermediate followed by reacting the intermediate with an organophosphite diester. Typically benzoyl chloride is the acylating agent, triethyl phosphite and bis (.beta.-chloroethyl) phosphite the sequential reactants, and the second step is carried out in the presence of a catalytic amount of a tertiary amine. A solvent such as methylene dichloride may be employed. Organic phosphate-phosphonates are useful as flame retardants, especially in urethane foams.

Synthesis of organic phosphate-phosphonates

Flame retardant phosphonate derivatives of polyalkylene polyamines are prepared having the structural formula: ##STR1## wherein R.sup.1, R.sup.2 and R.sup.5 can be the same or different substituted or nonsubstituted lower alkylene groups of about 2-10 carbons, or aryl groups of about 6-14 carbons; and R.sup.5 can also be haloalkyl of about 1-10 carbons;

Phosphonate derivatives of polyalkylene polyamines as flame retardants

Flame retardant oligomeric phosphate ester compositions having the structural formula: ##STR1## are prepared, wherein R is C.sub.1 -C.sub.10 alkyl or haloalkyl, R.sup.1 and R.sup.2 can be the same or different and are hydrogen, C.sub.1 -C.sub.10 alkyl or haloalkyl and n is an integer from zero to about 10. The method of preparing the compositions comprises reacting P.sub.2 O.sub.5 with a trialkyl or tris(haloalkyl)phosphate in the presence of about 0.01% to about 5% of a phosphite at a temperature from about 0.degree.-200.degree. C. A polyphosphate ester having P--O--P bonds is formed which is then reacted with an epoxide to yield the oligomeric phosphate ester flame retardant compositions. Alternatively, a method of preparing similar compositions comprises reacting P.sub.2 O.sub.5 with a trialkyl or tris(haloalkyl)phosphite at a temperature from about 0.degree. C. to about 200.degree. C. A mixed polyphosphate-polyphosphite ester having P--O--P bonds is formed which is then oxidized to yield a polyphosphate having P--O--P bonds; which is then reacted with an epoxide to yield the oligomeric phosphate ester flame retardant compositions.

Method of preparing oligomeric phosphate esters

Flame retardance is imparted to textile materials by impregnating them with a flame retardant composition comprising

Process for imparting flame retardance to textile materials

N-Alkylated aminoalkylphosphonates having the structural formula: ##STR1## where R.sup.1,R.sup.4 and R.sup.5 are straight or branched lower alkyl having one to five carbon atoms; R.sup.2 and R.sup.3 are selected from the group consisting of straight or branched lower alkyl having one to five carbon atoms and hydrogen and n is the integer 1 or 2, are prepared with acid numbers from about 5 to about 15 by contacting an amine and a phosphite and then adding this to an aqueous solution of an aldehyde or ketone. The reaction temperature is kept below about 70.degree. C. and water is removed under reduced pressure.

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Thousand Oaks, CA, United States of America

Thomas A Hardy