Non-isocyanate polyurethanes and methods of making and using the same
View Patent ↗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 copolymer comprising a first block and a second block, wherein the first block comprises a polymer, wherein said polymer 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 copolymer of claim 1 , wherein the second block comprises a polyester.
3. The copolymer of claim 1 , wherein the second block comprises a polyether.
4. The copolymer of claim 1 , wherein R 1 is —OH.
5. The polymer of claim 1 , wherein R 1 is —OR 2 .
6. The polymer of claim 5 , wherein R 2 is methyl, ethyl, or isopropyl.
7. The polymer of claim 5 , wherein R 2 is methyl.
8. The polymer of claim 1 , wherein R 2 is methyl, ethyl, or n-propyl.
9. The polymer of claim 1 , wherein X 1 is —(CH 2 ) 7 —.
10. The polymer of claim 1 , wherein X 2 is C 4-24 alkylene.
11. The polymer of claim 10 , 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 —.
12. The polymer of claim 11 , wherein X 2 is —(CH 2 ) 12 —.
13. The polymer of claim 1 , wherein X 2 is C 4-24 heteroalkylene.
14. The polymer of claim 13 , 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.
15. The polymer of claim 14 , 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 —.
16. The polymer of claim 15 , wherein X 3 is —(CH 2 ) 4 —.
17. The polymer of claim 14 , 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 —.
18. The polymer of claim 17 , wherein X 4 is —(CH 2 ) 4 —.
19. The polymer of claim 14 , wherein n is an integer from 80 to 120.
20. 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.