Methods of making polyboronic compounds and compositions related thereto
View Patent ↗Polyboronic compounds and methods of making them are provided. The polyboronic compounds are useful as crosslinking agents. The polyboronic compounds are produced by contacting a polymeric amine with a trialkylborate in the presence of a solvent so that the resulting molecule has more than one B—N bond.
1. A method of making a polyboronic compound comprising contacting a polymeric amine with a trialkylborate in the presence of a solvent to produce the polyboronic compound having more than one B—N bond.
2. The method of claim 1 , wherein the polyboronic compound comprises
3. The method of claim 1 , wherein the polyboronic compound comprises
or combinations thereof,
wherein R 1 -R 8 is hydrogen, alkyl group, alkenyl group, alkynyl group, aryl group, or combinations thereof;
X is nitrogen;
Y is a straight chain of —(CH 2 )—, a straight chain with pendant(s), a straight chain with branching, aromatic ring(s) directly connected, aromatic ring(s) indirectly connected, fused aromatic rings, heterocyclic ring(s) directly connected, heterocyclic ring(s) indirectly connected, fused heterocyclic rings, aliphatic ring(s) directly connected, aliphatic ring(s) indirectly connected, fused aliphatic rings, or combinations thereof; and
Z is carbon, silicon, oxygen, nitrogen, alkyl group, alkenyl group, alkynyl group, aromatic ring(s), aliphatic ring(s), heterocyclic ring(s), a metal atom, or combinations thereof.
4. The method of claim 1 , wherein the polymeric amine comprises ethylenediamine, diethylene triamine (DETA), triethylenetetramine (TETA), tetraethylenepentamine (TEPA), 1,2-, 1,3-propylenediamine, dipropylenetriamine, tripropylenetetramine, tetrapropylenepentamine, ethylene propylene triamine, ethylene dipropylene tetramine, diethylene propylene tetramine, ethylene tripropylene pentamine, diethylene dipropylene pentamine, triethylene propylene pentamine, or combinations thereof.
5. The method of claim 1 , wherein the trialkylborate comprises trimethylborate, triethylborate, tripropylborate, triisopropyl borate, tributyl borate, tri(tert-butyl)borate, or combinations thereof.
6. The method of claim 1 , wherein the solvent comprises methanol, ethanol, propanol, 2-propanol, butanol, 2-butanol, tert-butanol, or combinations thereof.
7. The method of claim 1 , wherein the step of contacting the polymeric amine with the trialkylborate includes contacting the polymeric amine with an excess amount of trialkylborate or an insufficient amount of trialkylborate.
8. The method of claim 1 , wherein the polyboronic compound comprises at least two B—N bonds.
9. The method of claim 1 , wherein the polyboronic compound comprises as many B—N bonds as there are N atoms in the polymeric amine.
10. A method of making a polyboronic compound comprising contacting a polymeric amine with a trialkylborate in the presence of a solvent to produce the polyboronic compound, wherein the polymeric amine comprises ethylenediamine, diethylene triamine (DETA), triethylenetetramine (TETA), tetraethylenepentamine (TEPA), 1,2-, 1,3-propylenediamine, dipropylenetriamine, tripropylenetetramine, tetrapropylenepentamine, ethylene propylene triamine, ethylene dipropylene tetramine, diethylene propylene tetramine, ethylene tripropylene pentamine, diethylene dipropylene pentamine, triethylene propylene pentamine, or combinations thereof.
11. The method of claim 10 , wherein the polyboronic compound comprises:
or combinations thereof.
12. The method of claim 10 , wherein the trialkylborate comprises trimethylborate, triethylborate, tripropylborate, triisopropyl borate, tributyl borate, tri(tert-butyl)borate, or combinations thereof.
13. The method of claim 10 , wherein the solvent comprises methanol, ethanol, propanol, 2-propanol, butanol, 2-butanol, tert-butanol, or combinations thereof.
14. The method of claim 10 , wherein the polyboronic compound has as many B—N bonds as an alkyl group of the trialkylborate has carbon molecules.
15. The method of claim 10 , wherein the step of contacting the polymeric amine with the trialkylborate includes contacting the polymeric amine with excess or an insufficient amount of trialkylborate.
16. A polyboronic compound having more than one B—N bond that provides more than one borate reaction crosslinking site.
17. The polyboronic compound of claim 16 comprising:
or combinations thereof, wherein R 1 -R 8 is hydrogen, alkyl group, alkenyl group, alkynyl group, aryl group, or combinations thereof;
X is nitrogen;
Y is a straight chain of —(CH 2 )—, a straight chain with pendant(s), a straight chain with branching, aromatic ring(s) directly connected, aromatic ring(s) indirectly connected, fused aromatic rings, heterocyclic ring(s) directly connected, heterocyclic ring(s) indirectly connected, fused heterocyclic rings, aliphatic ring(s) directly connected, aliphatic ring(s) indirectly connected, fused aliphatic rings, or combinations thereof; and
Z is carbon, silicon, oxygen, nitrogen, alkyl group, alkenyl group, alkynyl group, aromatic ring(s), aliphatic ring(s), heterocyclic ring(s), a metal atom, or combinations thereof.
18. The polyboronic compound of claim 16 produced by contacting a polymeric amine with a trialkylborate in the presences of a solvent.
19. The polyboronic compound of claim 16 , wherein the polymeric amine is ethylenediamine, diethylene triamine (DETA), triethylenetetramine (TETA), tetraethylenepentamine (TEPA), 1,2-, 1,3-propylenediamine, dipropylenetriamine, tripropylenetetramine, tetrapropylenepentamine, ethylene propylene triamine, ethylene dipropylene tetramine, diethylene propylene tetramine, ethylene tripropylene pentamine, diethylene dipropylene pentamine, triethylene propylene pentamine, or combinations thereof.
20. The polyboronic compound of claim 16 , wherein the trialkylborate is trimethylborate, triethylborate, tripropylborate, triisopropyl borate, tributyl borate, tri(tert-butyl)borate, or combinations thereof.