Phosphorus-containing polymers, and methods of producing thereof
Provided are methods of producing sulfur- and phosphorus-containing polymers from beta-lactones. The sulfur- and phosphorus-containing polymers include bio-based sulfur- and phosphorus-containing polymers that may be obtained from renewable sources.
1. A method, comprising:
combining a beta-lactone with a diol compound to produce an alkanoate compound having two terminal hydroxy groups; and
combining the alkanoate compound with a phosphanediamine compound or a phosphanetriamine compound to produce a phosphorus-containing polyester.
2. The method of claim 1 , wherein the beta-lactone is beta-propiolactone, beta-butyrolactone, or beta-valerolactone, and wherein the diol is ethylene glycol.
3. A method according to claim 1 , wherein
the beta-lactone corresponds to formula (1)
wherein the diol corresponds to formula (4) HO—R 4 —OH, wherein R 4 is -alkyl-, -cycloalkyl-, -aryl-, -heteroaryl-, -ether-, or -arylalkyl-; and
wherein the alkanoate compound having two terminal hydroxy groups corresponds to formula (7)
wherein R 1a , R 1b , R 1c , and R 1d is as defined for formula (1), and wherein R 4 is as defined above for formula (4);
wherein the phosphanediamine compound corresponds to the formula (C-1)
and
wherein the phosphanetriamine compound is a compound of formula (C-2)
wherein R y is alkyl or OR y1 , and wherein R y1 is alkyl; and
wherein the polymer comprises repeating units of formula
wherein each R 1a , R 1b , R 1c and R 1d is independently H or alkyl, R 4 is independently in each occurrence-alkyl-, -cycloalkyl-, -aryl-, -heteroaryl-, -ether-, or -arylalkyl-, each R z1 , R z2 , R z3 , R z4 , R z5 and R z6 is independently in each occurrence alkyl, R y is independently in each occurrence alkyl or —OR y1 ; and R y1 is alkyl.
4. The method of claim 3 , wherein R 1a is H or alkyl, R 1b , R 1c , and R 1d are all H, and R 4 is -alkyl.
5. A polymer produced according to the method of claim 1 .