IP Library Granted Patent US 8,916,336
Granted Patent B2
US 8,916,336 · App. 14/158,902 · Granted Dec 23, 2014

Patterning method using thiosulfate polymer and metal nanoparticles

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Quick Facts
Patent No.
US 8,916,336
App. No.
14/158,902
Granted
Dec 23, 2014
Kind
B2
Abstract

A thiosulfate polymer composition includes an electron-accepting photosensitizer component, either as a separate compound or as an attachment to the thiosulfate polymer. The thiosulfate polymer composition can be used in methods to form predetermined patterns of metal nanoparticles.

Claims (20)

1. A method comprising:

providing a polymeric layer comprising a non-crosslinked thiosulfate polymer that also comprises pendant organic charged groups,

photochemically reacting the non-crosslinked thiosulfate polymer to provide polymer layer areas comprising a crosslinked polymer having disulfide groups in the polymeric layer,

optionally washing the polymeric layer to remove any non-crosslinked thiosulfate polymer while leaving the crosslinked polymer having disulfide groups in the polymeric layer, and

contacting the polymeric layer with a dispersion of metal nanoparticles to complex the metal nanoparticles with the crosslinked polymer having disulfide groups.

2. The method of claim 1 , comprising contacting the polymeric layer with a dispersion of gold, silver, platinum, palladium, or copper nanoparticles.

3. The method of claim 1 , comprising photochemically reacting the non-crosslinked thiosulfate polymer to provide polymer layer areas in a predetermined pattern that comprise a crosslinked polymer having disulfide groups.

4. The method of claim 1 , wherein the polymeric layer further comprises an electron-accepting photosensitizer component.

5. The method of claim 1 , wherein washing the polymeric layer to remove the non-crosslinked thiosulfate polymer is carried out using an aqueous solution.

6. The method of claim 1 , wherein the polymeric layer further comprises an electron-accepting photosensitizer component that is a covalently-connected component of the non-crosslinked thiosulfate polymer.

7. The method of claim 1 , wherein the non-crosslinked thiosulfate polymer is a copolymer comprising, in random order: (a) recurring units comprising thiosulfate groups, and (b) recurring units comprising an electron-accepting photosensitizer component.

8. The method of claim 7 , wherein the copolymer comprises, in random order, (c) recurring units other than the (a) and (b) recurring units, which (c) recurring units comprise a pendant charged group, the (c) recurring units being present in an amount of at least 0.1 mol %, based on the total recurring units in the copolymer.

9. The method of claim 8 , wherein the (c) recurring units comprise a pendant carboxy, carboxylate, phospho, phosphonate, phosphate, sulfo, sulfonate, or sulfite group.

10. The method of claim 7 , wherein the (c) recurring units are present in an amount of at least 0.1 mol % and up to and including 50 mol %, based on the total recurring units in the copolymer.

11. The method of claim 7 , wherein the (c) recurring units are present in the copolymer in an amount of up to and including 50 mol %, the (a) recurring units are present in the copolymer in an amount of at least 1 mol %, and the copolymer further comprises (d) recurring units that have a total neutral charge and are present in an amount of at least 1 mol % and up to and including 49 mol %, all based on the total recurring units in the copolymer.

12. The method of claim 11 , wherein the molar ratio of the (a) recurring units to the (d) recurring units in the copolymer is from 1:3 to 3:1.

13. The method of claim 1 , wherein the non-crosslinked thiosulfate polymer comprises (a) recurring units comprising thiosulfate groups and (c) recurring units that comprise a pendant charged group in an amount of at least 0.1 mol %, based on the total recurring units in the non-crosslinked thiosulfate polymer.

14. The method of claim 1 , wherein the polymeric layer further comprises an electron-accepting photosensitizer component in an amount of at least 0.1 mol % and up to and including 10 mol %, in relation to the molar amount of thiosulfate groups present in the polymeric layer.

15. The method of claim 1 , wherein the polymeric layer further comprises an electron-accepting photosensitizer component that is a compound separate from the non-crosslinked thiosulfate polymer.

16. The method of claim 1 , wherein the polymeric layer further comprises an electron-accepting photosensitizer component that is an organic photosensitizer N-containing heterocyclic compound.

Assignments (11)
NOTICE OF SECURITY INTERESTS Recorded Mar 4, 2021
From: EASTMAN KODAK COMPANY
To: BANK OF AMERICA, N.A., AS AGENT
Reel/Frame 056984/0001 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Mar 4, 2021
From: EASTMAN KODAK COMPANY
To: ALTER DOMUS (US) LLC
Reel/Frame 056734/0233 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Mar 4, 2021
From: EASTMAN KODAK COMPANY
To: ALTER DOMUS (US) LLC
Reel/Frame 056734/0001 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Mar 4, 2021
From: EASTMAN KODAK COMPANY
To: ALTER DOMUS (US) LLC
Reel/Frame 056733/0681 →
RELEASE OF SECURITY INTEREST Recorded Jan 24, 2020
From: BARCLAYS BANK PLC
To: EASTMAN KODAK COMPANY; FAR EAST DEVELOPMENT LTD.; FPC INC.; KODAK (NEAR EAST) INC.; KODAK AMERICAS LTD.; KODAK REALTY INC.; LASER PACIFIC MEDIA CORPORATION; QUALEX INC.; KODAK PHILIPPINES LTD.; NPEC INC.
Reel/Frame 052773/0001 →
RELEASE OF SECURITY INTEREST Recorded Jul 30, 2019
From: JP MORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: EASTMAN KODAK COMPANY; FAR EAST DEVELOPMENT LTD.; PFC, INC.; KODAK (NEAR EAST), INC.; KODAK AMERICAS, LTD.; KODAK IMAGING NETWORK, INC.; KODAK PORTUGUESA LIMITED; KODAK REALTY, INC.; LASER PACIFIC MEDIA CORPORATION; PAKON, INC.; QUALEX, INC.; KODAK PHILIPPINES, LTD.; NPEC, INC.; CREO MANUFACTURING AMERICA LLC; KODAK AVIATION LEASING LLC
Reel/Frame 049901/0001 →
RELEASE OF SECURITY INTEREST Recorded Jul 22, 2019
From: JP MORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: QUALEX, INC.; EASTMAN KODAK COMPANY; FAR EAST DEVELOPMENT LTD.; FPC, INC.; KODAK (NEAR EAST), INC.; KODAK AMERICAS, LTD.; KODAK IMAGING NETWORK, INC.; KODAK PORTUGUESA LIMITED; KODAK REALTY, INC.; LASER PACIFIC MEDIA CORPORATION; PAKON, INC.; KODAK PHILIPPINES, LTD.; NPEC, INC.; CREO MANUFACTURING AMERICA LLC; KODAK AVIATION LEASING LLC
Reel/Frame 050239/0001 →
SECURITY INTEREST Recorded Mar 28, 2014
From: EASTMAN KODAK COMPANY; FAR EAST DEVELOPMENT LTD.; FPC INC.; KODAK (NEAR EAST), INC.; KODAK AMERICAS, LTD.; KODAK IMAGING NETWORK, INC.; KODAK PORTUGUESA LIMITED; KODAK REALTY, INC.; LASER-PACIFIC MEDIA CORPORATION; QUALEX INC.; KODAK PHILIPPINES, LTD.; NPEC INC.; KODAK AVIATION LEASING LLC
To: BARCLAYS BANK PLC, AS ADMINISTRATIVE AGENT
Reel/Frame 032553/0398 →
SECURITY INTEREST Recorded Mar 28, 2014
From: EASTMAN KODAK COMPANY; FAR EAST DEVELOPMENT LTD.; FPC INC.; KODAK (NEAR EAST), INC.; KODAK AMERICAS, LTD.; KODAK IMAGING NETWORK, INC.; KODAK PORTUGUESA LIMITED; KODAK REALTY, INC.; LASER-PACIFIC MEDIA CORPORATION; QUALEX INC.; KODAK PHILIPPINES, LTD.; NPEC INC.; KODAK AVIATION LEASING LLC
To: BANK OF AMERICA N.A., AS AGENT
Reel/Frame 032553/0152 →
SECURITY INTEREST Recorded Mar 28, 2014
From: EASTMAN KODAK COMPANY; FAR EAST DEVELOPMENT LTD.; FPC INC.; KODAK (NEAR EAST). INC.; KODAK AMERICAS, LTD.; KODAK IMAGING NETWORK, INC.; KODAK PORTUGUESA LIMITED; KODAK REALTY, INC.; LASER-PACIFIC MEDIA CORPORATION; QUALEX INC.; KODAK PHILIPPINES, LTD.; NPEC INC.; KODAK AVIATION LEASING LLC
To: JPMORGAN CHASE BANK, N.A. AS ADMINISTRATIVE AGENT
Reel/Frame 032552/0741 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 20, 2014
From: SHUKLA, DEEPAK; DONOVAN, KEVIN M.; DIRMYER, MATTHEW
To: EASTMAN KODAK COMPANY
Reel/Frame 032002/0001 →