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US 10,240,001 B2Granted
O-hydroxy-functionalized diamines, polyimides, methods of making each, and methods of use
AssigneeKing Abdullah University of Science and Technology
InventorsXiaohua Ma, Bader S. Ghanem, Ingo Pinnau
Life of this patent
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Abstract
Embodiments of the present disclosure provide for an ortho (o)-hydroxy-functionalized diamine, a method of making an o-hydroxy-functionalized diamine, an o-hydroxy-functionalized diamine-based polyimide, a method of making an o-hydroxy-functionalized diamine imide, methods of gas separation, and the like.
Claims19
A composition, comprising:
- an o-hydroxy-functionalized diamine having the following structure:
- wherein R is selected from the following structures:
- wherein R1 is H or a substituted or unsubstituted linear alkyl group, wherein each R2 and R4 are independently selected from the group consisting of:
- H and a linear or branched, substituted or unsubstituted, alkyl group, wherein Ar2 is selected from the group consisting of:
- an aryl group and a heteroaryl group where each are substituted or unsubstituted.
2 more elements
A composition, comprising:
- a polyimide having the following structure:
- wherein Ar3 is an aryl group or a heteroaryl group, wherein x is 1 to 100,000, wherein R is selected from the following structures:
- wherein R1 is H or a substituted or unsubstituted linear alkyl group wherein, each of R2 and R4 are independently selected from the group consisting of:
- H and a linear or branched, substituted or unsubstituted, alkyl group, wherein Ar2 is selected from the group consisting of:
- an aryl group and a heteroaryl group where each are substituted or unsubstituted.
2 more elements
A method of making an aromatic diamine, comprising:
- wherein A includes acetylation of the bulky starting structures by Friedel-Crafts reaction, wherein B includes transferring the diacetyl intermediate to diester via Baeyer-Villiger oxidation reaction, wherein C includes the hydrolysis of the diester, wherein D includes the nitration of the diphenol intermediate, wherein E includes the reduction of the ortho-diphenol-dinitrol intermediate to the corresponding ortho-hydroxy-functionalized diamine, wherein R is selected from the following structures:
- wherein R1, R2, and R4 are independently a linear or branched, substituted or unsubstituted alkyl group, wherein Ar2 is selected from the group consisting of:
- an aryl group and a heteroaryl group where each is substituted or unsubstituted.
A method for making a polyimide, comprising:
- reacting a dianhydride with an o-hydroxy-functionalized diamine to form a polyimide, wherein the o-hydroxy-functionalized diamine has the following structure:
- wherein R is selected from the following structures:
- wherein R1 is H or a substituted or unsubstituted linear alkyl group, wherein each of R2 and R4 are independently selected from the group consisting of:
- H and a linear or branched, substituted or unsubstituted, alkyl group, wherein Ar2 is selected from the group consisting of:
- an aryl group and a heteroaryl group where each are substituted or unsubstituted.
2 more elements
A membrane, comprising:
- a polyimide having the following structure:
- wherein Ar3 is selected from an aryl group or a heteroaryl group, wherein x is 1 to 100,000, wherein R is selected from the following structures:
- wherein R1 is H or a substituted or unsubstituted linear alkyl group wherein, each of R2 and R4 are independently selected from the group consisting of:
- H and a linear or branched, substituted or unsubstituted, alkyl group, wherein Ar2 is selected from the group consisting of:
- an aryl group and a heteroaryl group where each can be substituted or unsubstituted.
2 more elements
A method of separating a gas from a gas mixture, comprising:
- separating a first gas from a first gas mixture containing at least a second gas with a membrane to form a second gas mixture that is enriched in at least one gas component of the first mixture, wherein the membrane includes a polyimide having the following structure:
- wherein Ar3 is selected from an aryl group or a heteroaryl group, wherein x is 1 to 100,000, wherein R is selected from the following structures:
- wherein R1 is H or a substituted or unsubstituted linear alkyl group wherein, each of R2 and R4 are independently selected from the group consisting of:
- H and a linear or branched, substituted or unsubstituted, alkyl group, wherein Ar2 is selected from the group consisting of:
- an aryl group and a heteroaryl group where each are substituted or unsubstituted.
2 more elements
Dependencies are inferred from the claim text.