Polyimide polymer with oligomeric silsesquioxane
View Patent ↗A soluble polyimide polymer with tethered oligomeric silsesquioxane compounds is produced using efficient, gentle reactions. A carboxylic acid attachment point on the polymer backbone is used to connect the oligomeric silsesquioxane. The oligomeric silsesquioxane compound includes an amine or an alcohol on an organic tether, which reacts with the carboxylic acid attachment point to produce either an amide or an ester bond. The amide or ester bond includes a carbonyl carbon directly connected to a phenyl group in the polymer backbone. The resultant polyimide polymer has many beneficial properties.
1. A method of producing a polyimide polymer comprising:
(a) reacting at least one acid monomer with at least one diamino monomer to form a polyimide polymer backbone such that the polymer backbone includes at least-one non-terminal attachment point, wherein the attachment point is comprised of a carboxylic acid;
(b) after step a), reacting a functional group selected from the group consisting of an amine and an alcohol with the polymer backbone attachment point, wherein the functional group is connected to an oligomeric silsesquioxane (OS) compound.
2. The method of claim 1 wherein the polyimide polymer is soluble.
3. The method of claim 1 wherein the polymer backbone is isolated a maximum of one time.
4. The method of claim 1 wherein the OS is in the form of a polyhedron.
5. The method of claim 4 wherein the acid monomer is 4-4′-(hexafluoroisopropylidene) diphthalic anhydride (6-FDA), and wherein the diamino monomer is both diamino benzoic acid (DBA) and para phenylene diamine (p-PDA).
6. A method of producing a polyimide polymer comprising:
(a) reacting at least one acid monomer with at least one diamino monomer to form a polymer backbone, wherein the monomers are selected such that the polymer backbone includes a non-terminal attachment point;
(b) imidizing the polymer from step (a) to form a soluble polyimide polymer backbone,
(c) after step (b), reacting an oligomeric silsesquioxane (OS) compound to the attachment point on the polyimide polymer backbone, such that the OS compound is connected to the polyimide polymer backbone; and
(d) isolating the polymer backbone a maximum of one time.
7. The method of claim 6 wherein the OS is polyhedral and the OS has the general formula (RSi) n-1 (R′A) 1 (O 1.5 ) n wherein R and R′ are organic substituents, A is an element, n is an natural number, 1 represents the number one, and wherein R′ is connected to the polymer backbone.
8. The method of claim 7 wherein A is selected from the group consisting of Si, Al, B, Ge, Sn, Ti and Sb.
9. The method of claim 7 wherein the acid monomer is 4-4′-(hexafluoroisopropylidene) diphthalic anhydride (6-FDA), wherein the diamino monomer is both diamino benzoic acid (DBA) and para phenylene diamine (p-PDA), and wherein A is silicon.
10. The method of claim 6 wherein step (b) further comprises removing water from the imidization reaction by vaporizing and removing the water.
11. The method of claim 10 wherein step (c) further comprises removing water from the OS attachment reaction by vaporizing and removing the water.
12. The method of claim 6 wherein the attachment point is a carboxylic acid, and the OS compound includes at least one functional group selected from the group consisting of an amine and an alcohol, wherein the function group reacts with the carboxylic acid attachment point to connect the OS compound to the polymer backbone.