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Periodic structured organic films

a structured organic film and film technology, applied in the direction of polyamide coating, transportation and packaging, coatings, etc., can solve the problem that the nature of polymer chemistry offers poor control over the molecular-level structure of formed materials

Inactive Publication Date: 2017-01-26
XEROX CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patent describes a special type of film made up of repeating segments and linkers that form a covalent organic framework. This film has an ordered structure and can be used in various applications. Its technical effect is the creation of a new type of ordered film that can be used in various applications.

Problems solved by technology

Polymer chemistry processes can allow for polymerized chains to, in turn, or concomitantly, become ‘cross-linked.’ The nature of polymer chemistry offers poor control over the molecular-level structure of the formed material, i.e. the organization of polymer chains and the patterning of molecular monomers between chains is mostly random.

Method used

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  • Periodic structured organic films
  • Periodic structured organic films
  • Periodic structured organic films

Examples

Experimental program
Comparison scheme
Effect test

example 1

Type 2 SOF

[0151](Action A) Preparation of the Liquid Containing Reaction Mixture.

[0152]The following were combined: the building block benzene-1,4-dimethanol [segment=p-xylyl; Fg=hydroxyl (—OH); (0.47 g, 3.4 mmol)] and a second building block N4,N4,N4′,N4′-tetrakis(4-(methoxymethyl)phenyl)biphenyl-4,4′-diamine [segment=N4,N4,N4′,N4′-tetra-p-tolylbiphenyl-4,4′-diamine; Fg=methoxy ether (—OCH3); (1.12 g, 1.7 mmol)], and 17.9 g of 1-methoxy-2-propanol. The mixture was shaken and heated to 60° C. until a homogenous solution resulted. Upon cooling to room temperature, the solution was filtered through a 0.45 micron PTFE membrane. To the filtered solution was added an acid catalyst delivered as 0.31 g of a 10 wt % solution of p-toluenesulfonic acid in 1-methoxy-2-propanol to yield the liquid containing reaction mixture.

[0153](Action B) Deposition of Reaction Mixture as a Wet Film.

[0154]The reaction mixture was applied to the reflective side of a metalized (TiZr) MYLAR™ substrate using a c...

example 2

Control Experiment Wherein the Building Block Benzene-1,4-Dimethanol was not Included

[0162](Action A) Preparation of the Liquid Containing Reaction Mixture.

[0163]The following were combined: the building block N4,N4,N4′,N4′-tetrakis(4-(methoxymethyl)phenyl)biphenyl-4,4′-diamine [segment=N4,N4,N4′,N4′-tetra-p-tolylbiphenyl-4,4′-diamine; Fg=methoxy ether (—OCH3); (1.12 g, 1.7 mmol)], and 17.9 g of 1-methoxy-2-propanol. The mixture was shaken and heated to 60° C. until a homogenous solution resulted. Upon cooling to room temperature, the solution was filtered through a 0.45 micron PTFE membrane. To the filtered solution was added an acid catalyst delivered as 0.31 g of a 10 wt % solution of p-toluenesulfonic acid in 1-methoxy-2-propanol to yield the liquid containing reaction mixture.

[0164](Action B) Deposition of Reaction Mixture as a Wet Film.

[0165]The reaction mixture was applied to the reflective side of a metalized (TiZr) MYLAR™ substrate using a constant velocity draw down coater...

example 3

(Control Experiment Wherein the Building Block N4,N4,N4′,N4′-Tetrakis(4-(Methoxymethyl)Phenyl)Biphenyl-4,4′-Diamine was not Included)

[0168](Action A) Preparation of the Liquid Containing Reaction Mixture.

[0169]The following were combined: the building block benzene-1,4-dimethanol [segment=p-xylyl; Fg=hydroxyl (—OH); (0.47 g, 3.4 mmol)] and 17.9 g of 1-methoxy-2-propanol. The mixture was shaken and heated to 60° C. until a homogenous solution resulted. Upon cooling to room temperature, the solution was filtered through a 0.45 micron PTFE membrane. To the filtered solution was added an acid catalyst delivered as 0.31 g of a 10 wt % solution of p-toluenesulfonic acid in 1-methoxy-2-propanol to yield the liquid containing reaction mixture.

[0170](Action B) Deposition of Reaction Mixture as a Wet Film.

[0171]The reaction mixture was applied to the reflective side of a metalized (TiZr) MYLAR™ substrate using a constant velocity draw down coater outfitted with a bird bar having an 8 mil gap....

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Abstract

An ordered structured organic film comprising a plurality of segments and a plurality of linkers arranged as a covalent organic framework, wherein the structured organic film may be a multi-segment thick structured organic film.

Description

[0001]This application is a divisional application of U.S. patent application Ser. No. 12 / 815,688, the disclosure of which is totally incorporated herein by reference in its entirety.CROSS-REFERENCE TO RELATED APPLICATIONS[0002]Commonly assigned U.S. patent application Ser. Nos. 12 / 716,524; 12 / 716,449; 12 / 716,706; 12 / 716,324; 12 / 716,686; and Ser. No. 12 / 716,571, entitled “Structured Organic Films,”“Structured Organic Films Having an Added Functionality,”“Mixed Solvent Process for Preparing Structured Organic Films,”“Composite Structured Organic Films,”“Process For Preparing Structured Organic Films (SOFs) Via a Pre-SOF,”“Electronic Devices Comprising Structured Organic Films,” respectively, the disclosures of which are totally incorporated herein by reference in their entireties, describe structured organic films, methods for preparing structured organic films and applications of structured organic films.BACKGROUND OF THE INVENTION[0003]Materials whose chemical structures are compri...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C08J5/18C09D169/00B05D3/06C09D167/00C09D177/06C09D175/04C09D179/02C09D177/00
CPCC08J5/18C09D179/02C09D169/00C09D177/00C09D167/00C09D177/06C08J2375/00B05D3/065C08J2379/02C08J2369/00C08J2377/00C08J2367/00C08J2377/06C09D175/04C08G18/751C08G18/3281C08G18/329C08G18/7614Y10T428/24777
Inventor COTE, ADRIEN P.HEUFT, MATTHEW A.
Owner XEROX CORP