Non-isocyanate polyurethanes and methods of making and using the same
Polyurethane compositions are disclosed herein, as well as methods of making and using such polyesters. In some embodiments, the polyurethanes are formed from monomers derived from natural oils. In some embodiments, the polyurethanes are formed without the use of monomers bearing isocyanate groups.
1. A polymer, which comprises constitutional units formed from one of more compounds of Formula (I):
and constitutional units formed from one or more compounds for Formula (II):
wherein:
R 1 is —OH or —OR 2 ;
R 2 is C 1-6 alkyl or C 1-6 oxyalkyl;
X 1 is C 4-10 alkylene; and
X 2 is C 4-24 alkylene or C 4-24 heteroalkylene.
2. The polymer of claim 1 , wherein R 1 is —OH.
3. The polymer of claim 1 , wherein R 1 is —OR 2 .
4. The polymer of claim 3 , wherein R 2 is methyl, ethyl, or isopropyl.
5. The polymer of claim 3 , wherein R 2 is methyl.
6. The polymer of claim 1 , wherein R 2 is methyl, ethyl, or n-propyl.
7. The polymer of claim 1 , wherein X 1 is —(CH 2 ) 7 —.
8. The polymer of claim 1 , wherein X 2 is C 4-24 alkylene.
9. The polymer of claim 8 , wherein X 2 is —(CH 2 ) 4 —, —(CH 2 ) 6 —, —(CH 2 ) 8 —, —(CH 2 ) 10 —, —(CH 2 ) 12 —, —(CH 2 ) 14 —, —(CH 2 ) 16 —, —(CH 2 ) 18 —.
10. The polymer of claim 9 , wherein X 2 is —(CH 2 ) 12 —.
11. The polymer of claim 1 , wherein X 2 is C 4-24 heteroalkylene.
12. The polymer of claim 11 , wherein X 2 is
wherein
X 3 is C 1-6 alkylene;
X 4 is C 1-6 alkylene;
n is an integer from 1 to 500.
13. The polymer of claim 12 , wherein X 3 is —(CH 2 )—, —(CH 2 ) 2 —, —(CH 2 ) 3 —, —(CH 2 ) 4 —, —(CH 2 ) 5 —, —(CH 2 ) 6 —, —CH 2 —CH(CH 3 )—, or —CH(CH 3 )—CH 2 —.
14. The polymer of claim 13 , wherein X 3 is —(CH 2 ) 4 —.
15. The polymer of claim 12 , wherein X 4 is —(CH 2 )—, —(CH 2 ) 2 —, —(CH 2 ) 3 —, —(CH 2 ) 4 —, —(CH 2 ) 5 —, —(CH 2 ) 6 —, —CH 2 —CH(CH 3 )—, or —CH(CH 3 )—CH 2 —.
16. The polymer of claim 15 , wherein X 4 is —(CH 2 ) 4 —.
17. The polymer of claim 12 , wherein n is an integer from 80 to 120.
18. The polymer of claim 1 , wherein the one or more compounds of Formula (II) comprises:
one or more first diamine compounds wherein X 2 is —(CH 2 ) 4 —, —(CH 2 ) 6 —, —(CH 2 ) 8 —, —(CH 2 ) 10 —, —(CH 2 ) 12 —, —(CH 2 ) 14 , —(CH 2 ) 16 —, —(CH 2 ) 18 —; and
one or more second diamine compounds wherein X 2 is
wherein X 3 , X 4 , and n have the definitions recited above.
19. The polymer of claim 18 , wherein the molar ratio of constitutional units formed from the first diamine compounds to the constitutional units formed from the second diamine compound ranges from 1:100 to 100:1.
20. The polymer of claim 19 , wherein the molar ratio of constitutional units formed from the first diamine compounds to the constitutional units formed from the second diamine compound ranges from 1:10 to 10:1.