Stauffer Chemical Company

Akzo Nobel N.v.

Akzo America Inc.

Fred Jaffe

Edward N Walsh

Silvio L Giolito

Thomas A Hardy

John Tomko

Alan M Aaronson

Edward D Weil

Jeffrey E Telschow

Kyung S Shim

Mervin E Brokke

Milton L Honig

Arthur D Toy

Theodore A Marolewski

Johannes Hermanus Boelee

A process for the synthesis of a hydrocarbylvinyl-1-phosphonic acid hydrocarbyl ester, such as a 1-phenylvinylphosphonic acid dialkyl ester, which utilizes: (a) the base catalyzed addition (preferably using a nonnucleophilic strong organic base) of a hydrocarbyl phosphite, such as a dialkyl phosphite containing no more than about eight carbon atoms in either of its alkyl groups, to an aldehyde or methyl ketone, such as a phenyl ketone, as exemplified by acetophenone, to form a hydrocarbyl 1-hydroxy-1-hydrocarbylphosphonate, such as a dialkyl 1-hydroxy-1-phenylalkylphosphonate compound; (b) the acid-catalyzed esterification (preferably acetylation) of the compound from (a) with an acid anhydride to form an acylated intermediate; and (c) the removal of carboxylic acid (preferably at a temperature of from about 50&deg; C. to about 215&deg; C. under reduced or atmospheric pressure) from the intermediate from (b) to form the desired hydrocarbylvinylphosphonic acid hydrocarbyl ester, such as a 1-phenylvinylphosphonic acid dialkyl ester.

Synthesis of a hydrocarbylvinylphosphonic acid hydrocarbyl ester

Diethyl ethylphosphonate is formed by the catalytic rearrangement of triethyl phosphite in a reaction medium at elevated temperature, preferably using an ethyl iodide as the rearrangement catalyst, employing a heel of diethyl ethylphosphonate in the reaction medium when the reaction is begun with maintaining of the reaction medium at a temperature above the boiling point of the triethyl phosphite (for example, a temperature of from about 175.degree. C. to about 185.degree. C.) and addition of the triethyl phosphite to the reaction medium at a rate slow enough to maintain that temperature.

Process for the synthesis of diethyl ethylphosphonate

Epoxy resins can be cured by the use of a curing agent formed by the reaction of phosphorus pentoxide with a trialkyl phosphate or phosphonate.

Epoxy resin compositions containing a polyphosphoric/polyphosphonic

Destabilized elemental phosphorus, for example resulting from fire involvement due to exposure with air, can be treated by placing the destabilized elemental phosphorus in the presence of a weakly basic aqueous solution of an alkali metal hypochlorite as a blanketing agent. Sodium hypochlorite is preferred.

Method for treating destabilized, fire-involved elemental phosphorus

Liquid mixed triaryl thiophosphate mixtures can be prepared by forming a mixture of phenol and substituted phenols, forming a phosphite from that mixture and sulfurizing the phosphite, washing the thiophosphate with aqueous base, and drying the so washed thiophosphate under mild conditions. The products are liquid while containing at least 25 percent symmetrical triaryl thiophosphate. Colorless and odorless products are prepared.

Process for preparing liquid triaryl thiophosphate mixtures

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

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

A process of producing diethyl phosphite by reacting an excess of triethyl phosphite with phosphorous acid. The improved process results in a high quality diethyl phosphite product having low acidity that is suitable as an intermediate for most uses requiring a low acidity diethyl phosphite.

Process for producing diethyl phosphite

A composition and method for inhibiting damage in a functional fluid by incorporating therein a damage inhibiting amount of an ammonium salt of a phosphorus acid in accordance with the formula: ##STR1## wherein R, R', R', R''' can be the same or different and wherein R and R' can be conjoint and contain oxygen, nitrogen, and mixtures thereof; and represent alkyl, aralkyl, and alkenyl groups containing from 1 to about 30 carbon atoms, X represents oxygen or sulfur, Y' and Y'' represent lower alkoxy, lower thioalkoxy, alkenyloxy, thioalkenyloxy, lower alkyl, carboalkoxyalkyl, phenyl lower alkyl, thiophenoxy, aryloxy, alkaryloxy, aralkoxy and lower alkylthiophenoxy, Z represents oxygen or sulfur, and m equals 1 or 2.

Functional fluids containing ammonium salts of phosphorus acids

The neutralization of products which are phosphorus containing oligomers having ##STR1## linkages between phosphorus atoms and which are obtained by the self-condensation of .beta.-halo-alkyl esters of pentavalent phosphorus acids or by the condensation of these esters with an alkyl ester of a pentavalent phosphorus acid is accomplished by reaction with an alkylene oxide, either alone or in combination with water or an alcohol having the formula ROH where R is a C.sub.1 -C.sub.20 alkyl group, and is enhanced by heating the products with a Lewis acid to promote alcoholysis reactions between labile groups contained therein and structures formed by alkylene oxide neutralization of free acid groups. The stabilized product formed by this process gives a better cure when incorporated in a polyurethane foam.

Method of preparing stable condensation products using a Lewis acid

A method for decolorizing and stabilizing alkylphenyl esters of phosphoric acid which comprises contacting the esters with an effective amount of a sodium salt selected from the group consisting of sodium dithionite and sodium formaldehyde sulfoxylate for a sufficient length of time to decolorize and stabilize the esters against subsequent color formation.

Color improvement of phosphate esters

A method for decolorizing and stabilizing alkylphenyl esters of phosphoric acid which comprises contacting the esters with an effective amount of an oxidizable nitrogenous compound for a sufficient length of time to decolorize and stabilize the esters against subsequent color formation.

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Ossining, NY, United States of America

Fred Jaffe