Viscous bio-derived solvents for structured organic film (SOF) compositions

Patent metadata

Field	Value
Publication number	US-12258455-B2
Application number	US-202318153836-A
Country	US
Kind code	B2
Filing date	Jan 12, 2023
Priority date	Jan 12, 2023
Publication date	Mar 25, 2025
Grant date	Mar 25, 2025

Abstract

A method of forming a pre-cure solution for a structured organic film (SOF) is described, including contacting at least one type of segment and at least one type of pre-linker with a bio-based solvent. The method also includes dissolving the at least one type of segment and the at least one type of pre-linker within the bio-based solvent. The method also includes where the bio-based solvent has a viscosity above 0.92 MPa-s. A composition including a bio-based solvent is also disclosed.

First claim

What is claimed is:

1. A method of forming a pre-cure solution for a structured organic film (SOF), comprising:
contacting at least one segment and at least one pre-linker comprising a polyol, a diamine, a polyamine, or a combination thereof, with a bio-based solvent; and
dissolving the at least one segment and the at least one pre-linker within the bio-based solvent; and
wherein the bio-based solvent comprises 1-butylpyrrolidin-2-one, methyl-5-(dimethylamino)-2-methyl-5-oxopentanoate, dimethyl isosorbide, glycofurol, triacetin, diethylene glycol monoethyl ether acetate, acetyltributylcitrate, acetyltriethylcitrate, triethyl citrate, or combinations thereof.

2. The method of forming a pre-cure solution for a structured organic film (SOF) of claim 1 , further comprising heating the at least one segment and the at least one pre-linker and the bio-based solvent, wherein heating the at least one segment and the at least one pre-linker and the bio-based solvent is performed before or after dissolving the at least one segment and the at least one pre-linker within the bio-based solvent.

3. The method of forming a pre-cure solution for a structured organic film (SOF) of claim 1 , further comprising contacting a plurality of capping segments with the at least one segment and the at least one pre-linker and the bio-based solvent while forming the pre-cure solution.

4. The method of forming a pre-cure solution for a structured organic film (SOF) of claim 3 , wherein at least one segment and/or at least one or more of the plurality of capping segments comprises at least one ionic species.

5. The method of forming a pre-cure solution for a structured organic film (SOF) of claim 1 , further comprising contacting one or more additives with the pre-cure solution.

6. The method of forming a pre-cure solution for a structured organic film (SOF) of claim 5 , wherein the one or more additives comprise a surfactant, a leveling agent, an adhesion promoter, or a combination thereof.

7. The method of forming a pre-cure solution for a structured organic film (SOF) of claim 1 , further comprising contacting one or more catalysts with the pre-cure solution.

8. The method of forming a pre-cure solution for a structured organic film (SOF) of claim 7 , wherein catalyst is added in an amount from about 0.1 wt % to about 3 wt % based on a total weight of the pre-cure solution.

9. The method of forming a pre-cure solution for a structured organic film (SOF) of claim 1 , wherein a portion of at least one segment comprise an ionic capping segment.

10. The method of forming a pre-cure solution for a structured organic film (SOF) of claim 1 , further comprising allowing the bio-based solvent to evaporate to form the structured organic film (SOF) prior to heating the pre-cure solution.

11. The method of forming a pre-cure solution for a structured organic film (SOF) of claim 1 , wherein the pre-cure solution is heated from about 60° C. to about 90° C.

12. The method of forming a pre-cure solution for a structured organic film (SOF) of claim 1 , wherein the structured organic film (SOF) is cured from about 100° C. to about 200° C. for about 1 hour.

13. The method of forming a pre-cure solution for a structured organic film (SOF) of claim 1 , wherein no catalyst is added to the pre-cure solution or the structured organic film (SOF).

14. The method of forming a pre-cure solution for a structured organic film (SOF) of claim 1 , wherein the bio-based solvent further comprises dihydrolevoglucosenone, ethyl lactate, γ-Valerolactone, or combinations thereof.

15. A method of forming a pre-cure solution for a structured organic film (SOF), comprising:
contacting at least one segment and at least one pre-linker comprising a polyol, a diamine, a polyamine, or a combination thereof, with a bio-based solvent;
heating the at least one segment and the at least one pre-linker with the bio-based solvent; and
dissolving the at least one segment and the at least one pre-linker within the bio-based solvent;
forming a structured organic film (SOF) on a substrate from the pre-cure solution; and
curing the structured organic film (SOF), wherein:
the bio-based solvent comprises 1-butylpyrrolidin-2-one, methyl-5-(dimethylamino)-2-methyl-5-oxopentanoate, dimethyl isosorbide, glycofurol, triacetin, diethylene glycol monoethyl ether acetate, acetyltributylcitrate, acetyltriethylcitrate, triethyl citrate, or combinations thereof; and
heating the at least one segment and the at least one pre-linker and the bio-based solvent is performed before or after dissolving the at least one segment and the at least one pre-linker within the bio-based solvent.

16. The method of forming a pre-cure solution for a structured organic film (SOF) of claim 15 , wherein the bio-based solvent further comprises dihydrolevoglucosenone, ethyl lactate, γ-Valerolactone, or combinations thereof.

17. The method of forming a pre-cure solution for a structured organic film (SOF) of claim 15 , wherein the structured organic film (SOF) comprises a membrane.

18. The method of forming a pre-cure solution for a structured organic film (SOF) of claim 15 , wherein the structured organic film (SOF) is free-standing and thus not adhered to the substrate or a supporting structure after curing.

19. The method of forming a pre-cure solution for a structured organic film (SOF) of claim 18 , wherein the substrate comprises polyetheretherketone (PEEK).

20. A composition, comprising:
a bio-based solvent;
at least one structured organic film (SOF) segment; and
at least one structured organic film (SOF) pre-linker comprising a polyol, a diamine, a polyamine, or a combination thereof; and
wherein the bio-based solvent comprises 1-butylpyrrolidin-2-one, methyl-5-(dimethylamino)-2-methyl-5-oxopentanoate, dimethyl isosorbide, glycofurol, triacetin, diethylene glycol monoethyl ether acetate, acetyltributylcitrate, acetyltriethylcitrate, triethyl citrate, or combinations thereof.

Assignees

• Xerox Corp

Inventors

• Farrugia Valerie M
• Claridge Robert

Classifications

• C08J5/18

  Manufacture of films or sheets · CPC title

• C08J7/08 Primary

  Heat treatment · CPC title

• C08J2461/16

  of ketones with phenols · CPC title

• C08J3/095 Primary

  Oxygen containing compounds · CPC title