Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Mixing of two or more solid polymers; mixing of solid...
Reexamination Certificate
1995-02-10
2003-10-07
Moran, Marjorie (Department: 1631)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Mixing of two or more solid polymers; mixing of solid...
Reexamination Certificate
active
06630539
ABSTRACT:
BACKGROUND OF THE INVENTION
U.S. Pat. No. 5,310,808 to R. A. Grey describes various vinyl phosphonate derivatives which are useful in the manufacture of flame retarded thermoplastic copolymers. Various aryl group-containing vinylphosphonate species are embraced by a formula depicted at col. 3, lines 14-26 of this patent in which a linear or branched divalent hydrocarbyl radical, B, is depicted as being bonded at either end thereof to the two oxygen atoms of the moiety
with the structures —CH
2
—CH
2
— and —CH(CH
3
) —CH
2
— being given as examples of preferred groups for B.
SUMMARY OF THE INVENTION
The present invention are certain novel neopentylene phosphonate compounds containing, as the type of divalent group B shown in both the compounds of U.S. Pat. No. 5,310,808 and intermediates thereof, the novel divalent linkage —CH
2
—C(CH
3
)
2
—CH
2
—.
DESCRIPTION OF PREFERRED EMBODIMENTS
The compounds of the present invention are, for example, embraced by the formula
where: Ar is substituted or unsubstituted phenyl;
A is selected from the group consisting of hydrogen and, if conjoint with B, CH
2
; and
B is selected from the group consisting of hydroxy, oxyacyl, and, if conjoint with A, CH
2
. It will be appreciated that having A and B conjoint as CH
2
makes the entire grouping C<A(B) a vinyl group.
A particularly preferred embodiment of the present invention relates to final compounds where the group C<A(B) does form a vinyl structure having A and B being conjoint as the moiety CH
2
. This type of compound class is exemplified by the compound neopentylene 1-phenylvinylphosphonate which has the formula:
Another embodiment of the present invention is exemplified by the class of novel intermediates for the previously described vinyl group-containing compound. One specific compound of this type is neopentylene 1-acetoxy-1-phenylethylphosphonate which is of the formula:
Yet another embodiment of the present invention is the novel intermediate compounds for the previously described 1-acetoxy containing compounds. These compounds are exemplified by the compound neopentylene 1-hydroxy-1-phenylethylphosphonate which is of the formula:
The process for forming the desired final products of the type exemplified by (I) involves the reaction of neopentylene hydrogen phosphonate with acetophenone to yield compounds as exemplified by (III) followed by acetylation with acetic anhydride to form the type of compound exemplified by (II) followed by acid-catalyzed deacetylation of (II) to form the final desired compound (I).
REFERENCES:
patent: 4255324 (1981-03-01), Granzow et al.
patent: 5310808 (1994-05-01), Grey
White, “Chemical Patent Practice”, (1991), pp. 144-147.*
Edmundson, R.S. Cyclic organophosphorus compounds. Part XVI mass spectrometric fragmentation of some 5,5-dimethyl-1,3,2-dioxaphosphorinan 2-oxides and 2-sulphides. (1981) Phosphorus and Sulfur. vol. 9, pp. 307-314.
Telschow Jeffrey E.
Tomko John
AKZO Nobel N.V.
Fennelly Richard P.
Moran Marjorie
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