Halogen-free cyclic phosphorus-containing flame retardant compounds
AssigneeMonsanto Company
InventorsFrank E. Paulik, Carol R. Weiss
Life of this patent
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Abstract
Certain (1,3,2-dioxaphosohorinanemethan) amine compounds, which are useful as halogen-free flame retardant compounds, are disclosed. The compounds are particularly useful in polyurethane compositions.
Claims15
A compound having the formula:
- ##STR11## wherein A is:
- ##STR12## R is any one of R.sub.1 to R.sub.6, and R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, and R.sub.6 are independently selected from the group consisting of hydrogen, alkyl groups having from 1 to 4 carbon atoms and aryl and substituted aryl groups having from 6 to 8 carbon atoms and wherein the compound is a solid at ambient temperature.
The compound 5,5,5',5',5",5"-hexamethyl tris(1,3,2-dioxaphosphorinanemethan)amine 2,2',2"-trioxide having the formula:
- ##STR13## wherein A is:
- ##STR14## and wherein the compound is a solid at ambient temperature.
A composition of matter comprising an organic polymeric material and a fire retardant amount of a compound having the formula:
- ##STR15## wherein A is:
- ##STR16## R is any one of R.sub.1 to R.sub.6, and R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, and R.sub.6 are independently selected from the group consisting of hydrogen, alkyl groups having from 1 to 4 carbon atoms and aryl and substituted aryl groups having from 6 to 8 carbon atoms and wherein the compound is a solid at ambient temperature.
A composition of matter comprising a polyurethane foam and a fire retardant amount of 5,5,5',5',5",5"-hexamethyl tris(1,3,2-dioxaphosphorinanemethan) amine 2,2',2"-trioxide having the formula:
- ##STR17## wherein A is:
- ##STR18## wherein the 5,5,5',5',5",5"-hexamethyl tris(1,3,2-dioxaphosphorinanemethan) amine 2,2',2"-trioxide is a solid at ambient temperature.
A process for the production of compounds having the formula:
- ##STR19## wherein A is:
- ##STR20## R is any one of R.sub.1 to R.sub.6, and R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, and R.sub.6 are independently selected from the group consisting of hydrogen, alkyl groups having from 1 to 4 carbon atoms and aryl and substituted aryl groups having from 6 to 8 carbon atoms, comprising the steps of:
- (a) reacting a normal alcohol having from 4 to about 8 carbon atoms and paraformaldehyde with hexamethylenetetramine in the presence of a catalyst comprising an organic aliphatic carboxylic acid having from 2 to about 7 carbon atoms to produce a tris-alkoxymethanamine having the general formula:
- [C.sub.x H.sub.2x+1 --O--CH.sub.2 ].sub.3 --N
- wherein X is a number from 4 to about 8;
- (b) purifying the tris-alkoxymethanamine;
- (c) adding phosphorus trichloride to a mixture of a 1,3-diol derivative and water and an organic solvent at a temperature of from about 10.degree. C. to about 60.degree. C. to produce a 5,5-di-substituted 1,3,2-dioxaphosphorinane-2-oxide having the general formula:
- ##STR21## wherein R.sub.1 and R.sub.2 are independently selected from the group consisting of hydrogen, alkyl groups having from 1 to 4 carbon atoms and aryl and substituted aryl groups having from 6 to 8 carbon atoms;
- (d) purifying the 5,5-di-substituted 1,3,2-dioxaphosphorinane-2-oxide;
- (e) reacting the tris-alkoxymethanamine and the 5,5-disubstituted 1,3,2-dioxaphosphorinane-2-oxide in an organic solvent with an acid catalyst to produce 5,5,5',5',5",5"-substituted tris(1,3,2-dioxaphosphorinanemethan) amine 2,2',2"-trioxide having the general formula:
- ##STR22## wherein A is:
- ##STR23## R is any one of R.sub.1 to R.sub.6, and R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, and R.sub.6 are independently selected from the group consisting of hydrogen, alkyl groups having from 1 to 4 carbon atoms and aryl and substituted aryl groups having from 6 to 8 carbon atoms;
- and
- (f) purifying and drying the 5,5,5',5',5",5"-substituted tris(1,3,2-dioxaphosphorinanemethan) amine 2,2',2"-trioxide.
Dependencies are inferred from the claim text.