Process of making poly(glycidyl azide) product and compounds useful therein

A method of making a product comprising poly(glycidyl azide) polymer the method comprising the steps of:

• (A) Preparing a mixture comprising:
• (1) alkali metal and/or alkaline earth metal azides;
• (2) an effective amount of a quaternary amine compound which compound is selected from the group consisting of compounds having the following representative formulas:
• (R.sup.1).sub.a (R.sup.2).sub.(4-a)N.sup.(+) X.sup.(-), (I)
• (R.sup.3).sub.2 NC.sub.5 H.sub.4 N.sup.(+) R.sup.1 X.sup.(-), (II)
• (R.sup.3).sub.2 NC.sub.6 H.sub.4 R.sup.4.dbd. R.sup.4 C.sub.5 H.sub.4 N.sup.(+) R.sup.1 X.sup.(-) (III)
• [(R.sup.2).sub.3 N.sup.(+) ].sub.2 R.sup.8 X.sup.(-).sub.2 (IV)
• [(R.sup.3).sub.2 NC.sub.5 H.sub.4 N.sup.+ ].sub.2 R.sup.8 X.sup.(-).sub.2 (V)
• and blends of compounds having the representative formula (I), (II), (III), (IV) and (V), wherein:
• (a) R.sup.1 can be the same or different and selected from:
• {[R.sup.5 (OR.sup.6).sub.b ].sub.(2-c) (R.sup.5).sub.c N[C(R.sup.7).sub.2 ].sub.d }.sub.e C(R.sup.7).sub.(3-e)CH.sub.2 --, or {R.sup.5 (OR.sup.6).sub.f O[C(R.sup.7).sub.12 ].sub.d }.sub.e C(R.sup.7).sub.(3-e) CH.sub.2 --, or {R.sup.5 (OR.sup.6).sub.b Q[C(R.sup.7).sub.2 ].sub.d }.sub.e C(R.sup.7).sub.(3-e) CH.sub.2 --, wherein
• R.sup.5 groups can be the same or different and are selected from hydrogen or a C.sub.1 to C.sub.10, alkyl group,
• R.sup.6 groups can be the same and different and are divalent organic groups,
• R.sup.7 groups can be the same or different and are selected from hydrogen and C.sub.1 to C.sub.10 alkyl groups
• Q is selected from alkylene, arylene and combinations thereof, and may be substituted with aryl or alkyl groups, oxygen, nitrogen, carbonyl, urylene, carbamato and imino groups, and combinations thereof,
• (b) R.sup.2 groups are the same or different and are selected from C.sub.1 to C.sub.10 alkyl groups, and
• (c) R.sup.3 groups can be the same or different and are selected from C.sub.1 to C.sub.8 alkyl groups containing oxygen or nitrogen hetero atoms, provided that such hetero atoms are attached only to carbon atoms, and the two R.sup.6 groups together with adjacent nitrogen atom shown in formula (II) can form a heterocyclic ring containing 3 to 7 atoms,
• (d) R.sup.4 groups can be the same or different and are selected from --CH.dbd., --CR.sup.2 .dbd. and --N.dbd..
• (e) R.sup.8 groups are defined as --CH.sub.2 [C(R.sup.7).sub.2 ].sub.(d+1) (OR.sup.6).sub.b Q[C(R.sup.7).sub.2 ].sub.(d+1) CH.sub.2 --
• (f) a is a number from 1 to 3,
• (g) b is a number from 1 to 50,
• (h) c is a number from 0 to 1,
• (i) d is a number from 1 to 15,
• (j) e is a number from 1 to 3,
• (k) f is a number from 0 to 50,
• (l) X is a suitable anion.
• (B) reacting the mixture prepared in step (A) with polyepichlorohydrin polymer to produce a reaction product, and
• (C) recovering from the reaction product a product comprising poly(glycidyl azide) polymer.