Aqueous monomer compositions and methods of making and using the same
Aqueous compositions of carboxylic acids, carboxylate esters, and carboxylate salts are generally disclosed, including methods of using such compounds to make various polymers, including, but not limited to, polyesters, polyamides, and polycarbamates. In certain embodiments, the carboxylic acids, carboxylate esters, and carboxylate salts are derived from a renewable source, such as a natural oil.
1. A method of forming a polymer, the method comprising:
(a) providing a composition comprising: water and a compound of formula (I)
wherein:
X 1 is C 12-20 alkylene, optionally substituted one or more times with substituents selected independently from —OH and C 1-6 oxyalkyl;
R 1 and R 2 are independently —OH, —O—R 4 , or —O − Z + ;
R 4 is C 1-6 alkyl or C 2-24 heteroalkyl, each of which is optionally substituted one or more times by —OH; and
Z + is a positively charged counterion;
provided that at least one of R 1 and R 2 is not —OH; and
(b) reacting one or more compounds of formula (I) with one or more monomers to form a polymer.
2. The method of claim 1 , wherein the one or more monomers are polyols and the formed polymer is a polyester.
3. The method of claim 1 , wherein the one or more monomers are polyamines and the formed polymer is a polyamide.
4. The method of claim 1 , wherein the one or more monomers are polyisocyanates and the formed polymer is a polycarbamate.
5. The method of claim 2 , wherein the polyols are diols.
6. The method of claim 3 , wherein the polyamines are diamines.
7. The method of claim 4 , wherein the polyisocyanates are diisocyanates.
8. The method of claim 1 , wherein X 1 is —(CH 2 )12-, —(CH 2 )14-, —(CH 2 )16-, —(CH 2 )18-, —(CH 2 )20-, or —(CH 2 )22-.
9. The method of claim 8 , wherein X 1 is —(CH 2 )16-.
10. The method of claim 1 , wherein R 1 is —OH.
11. The method of claim 1 , wherein R 1 is —O − Z + .
12. The method of claim 1 , wherein R 1 is —O—R 4 .
13. The method of claim 11 , wherein R 2 is —O − Z + .
14. The method of claim 12 , wherein R 2 is —O—R 4 .
15. The method of claim 13 , wherein Z + is the conjugate acid of a Lewis base.
16. The method of claim 15 , wherein Z + is an ammonium compound.
17. The method of claim 16 , wherein the ammonium compound is a compound of formula (III):
wherein:
R 5 , R 6 , R 7 , and R 8 are independently a hydrogen atom or a C 1-10 alkyl, where the alkyl group is optionally substituted one or more times with substituents selected independently from the group consisting of a halogen atom, —OH, —NH 2 , and C 1-6 heteroalkyl.
18. The method of claim 17 , wherein R 5 , R 6 , R 7 , and R 8 are independently a hydrogen atom or a C 1-6 alkyl, where the alkyl group is optionally substituted one or more times with substituents selected independently from the group consisting of a halogen atom, —OH, and —O(C 1-6 alkyl).
19. The method of claim 18 , wherein Z + is selected from the group consisting of:
ammonium cation, triethylammonium cation, and N,N-dimethylethanolammonium cation.
20. The method of claim 14 , wherein R 4 is C 2-24 oxyalkyl, which is optionally substituted one or more times by —OH.
21. The method of claim 20 , wherein R 4 is —CH 2 CH 2 —(O—CH 2 —CH 2 ) p —O—R 9 , wherein p is an integer from 0 to 10, and R 9 is a hydrogen atom, methyl, or ethyl.