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Crosslinkable polymers

a reactive polymer and crosslinking technology, applied in the field of crosslinkable reactive polymers, can solve the problems of affecting the fidelity or correspondence of the material, the use of ito coatings, and the inability to meet the requirements of the material, and achieves the effects of high electrical conductivity, easy production, and high fidelity or corresponden

Active Publication Date: 2016-02-18
EASTMAN KODAK CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patent describes a new type of reactive polymer that can be used to create highly conductive metal patterns without using expensive semiconductor fabrication methods. The polymer can be exposed to strong acid to create sulfonic acid or sulfonate groups that can bind with metal ions, while other parts of the polymer can provide crosslinking capability. These polymers can be water-insoluble in certain regions and water-permeable in other regions, allowing for precise patterning. The polymer can be easily washed away in non-patterned regions and then treated with a catalytic metal ion bath to form metal particles suitable for electroless metal plating. The resulting metal patterns have high fidelity to the pattern created by UV radiation and exhibit low resistivity. Overall, this new technology offers a cost-effective solution for creating highly conductive metal patterns.

Problems solved by technology

As the increase in the use of such devices has exploded in frequency and necessity by displacing older technologies, there has been a concern that electromagnetic radiation emission from such devices may cause harm to the human body or neighboring devices or instruments over time.
However, the use of ITO coatings has a number of disadvantages.
Indium is an expensive rare earth metal and is available in limited supply.
Moreover, ITO is a ceramic material and is not easily bent or flexed and such coatings require expensive vacuum deposition methods and equipment.
In addition, ITO conductivity is relatively low, requiring short line lengths to achieve desired response rates (upon touch).
These smaller segments require additional driving and sensing electronics, further adding to the cost of the devices.
However, all of these technologies are expensive, tedious, or extremely complicated so that the relevant industries are spending considerable resources to design improved means for forming conductive patterns for various devices especially touch screen displays.
However, the “protection” of sulfonate groups is known to be a problem because of the tendency for sulfonate esters to be very reactive, making any “protecting” group unstable to a wide variety of chemical reagents and conditions and thus ineffective.
Some limited success has been reported from use of hindered alcohols such as neopentyl, cyclopentyl, methyl tetrahydropyranyl alcohols.

Method used

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  • Crosslinkable polymers
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Examples

Experimental program
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Effect test

invention example 1

active Polymer A from 3-f(4-t-butoxycarbonyloxy)-α-trifluoromethylbenzylsulfolpropyl methacrylate and glycidyl methacrylate in an 85:15 mol ratio

[0345]3 -[(4-t-Butoxycarbonyloxy)-α-trifluoromethylbenzylsulfo]propyl methacrylate monomer prepared above (2.05 g) and 0.11 g of glycidyl methacrylate were weighed out in a 100 ml single-neck round bottom flask and then dissolved in THF and chloroform to obtain a 20 weight % solids solution. With solution still cloudy, 0.03 g of 2,2′-azodi(2-methylbutyronitrile) (AMBN) initiator was added and the reaction solution was purged with nitrogen for about 30 minutes, capped with a septum, and placed in a preheated oil bath at 65° C. overnight. The reaction solution cleared during heating and was cooled and precipitated into ethanol, filtered, and dried. The resulting white solid was then dissolved in THF, precipitated into ethanol, filtered, and dried in a high vacuum oven at room temperature overnight. The resulting Reactive Polymer A had a weigh...

invention example 2

tion Polymer B from 3-[(4-t-butoxycarbonyloxy)-α-trifluoromethylbenzylsulfo]propyl methacrylate, glycidyl methacrylate, and t-butyl methacrylate (64:15:21 mol ratio)

[0349]3- [(4-t-Butoxycarbonyloxy)-α-trifluoromethylbenzylsulfo]propyl methacrylate monomer prepared above (3.85 g), 0.37 g of (-butyl methacrylate, and 0.27 g of glycidyl methacrylate were weighed out in a 100 ml single-neck round bottom flask and then dissolved in THF to obtain a 25 weight % solids solution. Then, 0.061 g of 2,2′-azodi(2-methylbutyronitrile) (AMBN) initiator was added and the reaction solution was purged with nitrogen for about 30 minutes, capped with a septum, and placed in a preheated oil bath at 65° C. overnight. The reaction solution cleared during heating and was cooled and precipitated into ethanol, filtered, and dried. The resulting white solid was then dissolved in THF, precipitated into ethanol, filtered, and dried in a high vacuum oven at room temperature overnight. The resulting Reactive Poly...

use examples 1 and 2

ive Composition Films and Electrically-Conductive Copper Patterns

[0350]Reactive Polymers A (for Invention Example 3) and B (for Invention Example 4) described above were dissolved in MEK to form 5 weight % reactive compositions along with 0.2 weight % of (methylphenyl)-diphenylsulfonium triflate salt (a monomer unit to onium salt molar ratio of 25:1). Each of the resulting reactive compositions was filtered and spin coated at 1200 RPM onto a substrate formed from poly(ethylene terephthalate) film with a polymeric adhesion layer of a polymer derived from glycidyl methacrylate and butyl acrylate that was applied before stretching as previously described, to form polymeric films on the substrate.

[0351]Each of the resulting precursor articles was exposed to short ultraviolet light through a chrome-on-quartz contact mask for 30 seconds, followed by contact with a vacuum hotplate at 110° C. for 1 to 2 minutes. Each resulting intermediate article was then immersed in a 0.4 molar silver nit...

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Abstract

Crosslinkable polymers comprise recurring units represented by:wherein R, R′, and R″ are independently hydrogen or an alkyl, cyano, or halo group; R1 is hydrogen or a halo, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, cyano, hydroxy, alkoxy, carboxy, or ester group; L is an organic linking group; EWG represents an electron withdrawing group having a Hammett-sigma value greater than or equal to 0.35 such that the oxygen-carbon bond in O—C(EWG)(R1) is cleavable in the presence of a cleaving acid having a pKa of 2 or less as measured in water; Ar is a substituted or unsubstituted arylene group; X is NR2 or oxygen; R2 is hydrogen or an alkyl group; t-alkyl represents a tertiary alkyl group having 4 to 6 carbon atoms, and m represents at least 1 mol % and up to and including 100 mol %, based on the total recurring units in the polymer.

Description

RELATED APPLICATIONS[0001]Reference is made to the following copending and commonly assigned patent applications, the disclosures of which are incorporated herein by reference:[0002]U.S. Ser. No. 14 / 084,675 that was filed Nov. 20, 2013 by Wexler, Bennett, and Lindner;[0003]U.S. Ser. No. 14 / 084,693 that was filed Nov. 20, 2013 by Irving, Wexler, Bennett, and Lindner;[0004]U.S. Ser. No. 14 / 084,711 that was filed Nov. 20, 2013 by Wexler, Bennett, and Lindner;[0005]U.S. Ser. No. 14 / 071,765 that was filed Nov. 5, 2013 by Brust, Irving, and Falkner; U.S. Ser. No. 14 / 071,879 that was filed Nov. 5, 2013 by[0006]Brust, Irving, Falkner, and Wyand; and[0007]U.S. Ser. No. 14 / ______ filed on even date herewith by Brust, Bennett, and Irving and entitled “Forming Electrically-Conductive Patterns Using Crosslinkable Reactive Polymers” (Attorney Docket No. K001788 / JLT).FIELD OF THE INVENTION[0008]This invention relates to crosslinkable reactive polymers that can be used a method for forming patterns...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C08F220/68
CPCC08F220/68C08F20/38C08F28/02C08F120/38C08F128/02C08F220/382C08F220/385C08F220/387C08F122/24
Inventor BRUST, THOMAS B.BENNETT, GRACE ANNIRVING, MARK EDWARD
Owner EASTMAN KODAK CO