IP Library Granted Patent US 7,413,849
Granted Patent B2
US 7,413,849 · App. 10/937,386 · Granted Aug 19, 2008

Substituted benzene developing solvent for photopolymerizable printing plates

Assignee: Nupro Technologies
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Quick Facts
Patent No.
US 7,413,849
App. No.
10/937,386
Granted
Aug 19, 2008
Kind
B2
Abstract

Flexographic printing plates are produced by exposing the photopolymer plates to a light source and washing out (developing) the masked out, non-exposed areas with a solvent. The invention provides substituted benzene solvents suitable for use in the development of photopolymer printing plates. The solvents, which include substituted benzene alone or mixed with co-solvents and/or non-solvents, are effective in developing a large number of different photopolymer printing plates and can produce images superior to those obtained with commercially available solvents currently used in such applications.

Claims (46)

1. A method for the development of photopolymerizable flexographic relief printing plates comprising

a) selecting a developing solvent, said developing solvent comprising at least one substituted benzene selected from the group consisting of

i) compound (I)

where R 1 -R 5 are the same or different, and denotes a hydrogen, hydroxyl, alkyl, alkenyl, aryl, amine/amide, ester, carboxylic acid, and aldehyde,

ii) di-sec-butyl benzene, and

iii) di-n-butyl benzene; and

b) washing an exposed flexographic relief printing plate with said developing solvent.

2. The method of claim 1 , wherein the compound (I) is selected from the group consisting of tert-butyl benzene, tert-butyl xylene, di-ten-butyl benzene, tert-butyl toluene, di-tert-butyl toluene, di-tent-butyl xylene, 1 -tert-butyl-3,5-dimethylbenzene, and combinations thereof.

3. The method of claim 1 , wherein the photopolymerizable flexographic relief printing plates is selected from the group consisting of block co-polymers of styrene and butadiene, block co-polymers of styrene and isoprene, co-polymers of butadiene and acrylonitrile, terpolymers of butadiene, acrylonitrile, and acrylic acid.

4. The method of claim 1 , wherein the developing solvent further comprising a co-solvent.

5. The method of claim 4 , wherein the co-solvent is selected from the group consisting of n-butanol, 2-ethoxyethanol, benzyl alcohol, ethanol, methanol, propanol, isopropanol, alpha terpineol, dipropylene glycol methyl ether, 2-butoxyethanol, isopropyl alcohol, and 2-(2-butoxyethoxy) ethanol, cyclopentanol, cyclohexanol, cycloheptanol, substituted cyclopentanol, substituted cyclohexanol, substituted cycloheptanol, cyclopentyl substituted alcohol, cyclohexyl substituted alcohol, and cycloheptyl substituted alcohol.

6. The method of claim 5 , wherein the substituted cyclohexanol is 4-ethycyclohexanol.

7. The method of claim 5 , wherein the substituted cyclopentanol is 2,3 dimethylcyclopentanol.

8. The method of claim 5 , wherein the cyclohexyl substituted alcohol is cyclohexylpropanol.

9. The method of claim 5 , wherein the cyclopentyl substituted alcohol is 4-cyclopentylpentanol.

10. The method of claim 1 , wherein the developing solvent further comprising a non-solvent.

11. The method of claim 10 , wherein the non-solvent is selected from the group consisting of aliphatic petroleum distillates, naphthas, paraffinic solvents, hydro-treated petroleum distillates, mineral oil, mineral spirits, ligroin, decane, octane, and hexane.

12. The method of claim 11 , wherein the paraffinic solvents are isoparafins.

13. The method of claim 1 , wherein the developing solvent further comprising a co- solvent and a non-solvent.

14. The method of claim 1 , wherein the co-solvent is selected from the group consisting of n-butanol, 2-ethoxyethanol, benzyl alcohol, ethanol, methanol, propanol, isopropanol, alpha terpineol, dipropylene glycol methyl ether, 2-butoxyethanol, isopropyl alcohol, and 2-(2-butoxyethoxy) ethanol, cyclopentanol, cyclohexanol, cycloheptanol, substituted cyclopentanol, substituted cyclohexanol, substituted cycloheptanol, cyclopentyl substituted alcohol, cyclohexyl substituted alcohol, and cycloheptyl substituted alcohol.

15. The method of claim 13 , wherein the non-solvent is selected from the group consisting of aliphatic petroleum distillates, naphthas, paraffinic solvents, hydro-treated petroleum distillates, mineral oil, mineral spirits, ligroin, decane, octane, and hexane.

16. The method of claim 15 wherein the paraffinic solvents are isoparaffins.

17. The method of claim 13 , wherein the substitute benzene is present in an amount of about 40-70% by volume, the co-solvent is present in an amount of about 20-50% by volume, and the non-solvent is present in an amount of about 10-30% by volume.

18. The method of claim 1 , further comprising the step of drying the flexographic relief printing plate to remove the developing solvent.

19. A developing solvent for the development of photopolymerizable flexographic relief printing plates comprising at least one substituted benzene selected from the group consisting of

a) compound (I)

where R 1 -R 5 are the same or different, and denotes a hydrogen, hydroxyl, alkyl, alkenyl, aryl, amine/amide, ester, carboxylic acid, and aldehyde,

b) di-sec-butyl benzene, and

c) di-n-butyl benzene.

20. The developing solvent of claim 19 , wherein the compound (I) is selected from the group consisting of tert-butyl benzene, tert-butyl xylene, di-tert-butyl benzene, tert-butyl toluene, di-tert-butyl toluene, di-tert-butyl xyiene, 1-tert-butyl-3,5-dimethylbenzene, and combinations thereof.

21. The developing solvent of claim 19 , wherein the photopolymerizable flexographic relief printing plates is selected from the group consisting of block co-polymers of styrene and butadiene, block co-polymers of styrene and isoprene, co-polymers of butadiene and acrylonitrile, terpolymers of butadiene, acrylonitrile, and acrylic acid.

22. The developing solvent of claim 19 , wherein the developing solvent further comprising a co-solvent.

23. The developing solvent of claim 22 , wherein the co-solvent is selected from the group consisting of n-butanol, 2-ethoxyethanol, benzyl alcohol, ethanol, methanol, propanol, isopropanol, alpha terpineol, dipropylene glycol methyl ether, 2-butoxyethanol, isopropyl alcohol, and 2-(2-butoxyethoxy) ethanol, cyclopentanol, cyclohexanol, cycloheptanol, substituted cyclopentanol, substituted cyclohexanol, substituted cycloheptanol, cyclopentyl substituted alcohol, cyclohexyl substituted alcohol, and cycloheptyl substituted alcohol.

24. The developing solvent of claim 23 . wherein the substituted cyclohexanol is 4-ethycyclohexanol.

25. The developing solvent of claim 23 , wherein the substituted cyclopentanol is 2,3 dimethylcyclopentanol.

26. The developing solvent of claim 23 , wherein the cyclohexyl substituted alcohol is cyclohexylpropanol.

27. The developing solvent of claim 23 , wherein the cyclopentyl substituted alcohol is 4-cyclopentylpentanol.

28. The developing solvent of claim 19 , wherein the developing solvent further comprising a non-solvent.

29. The developing solvent of claim 28 , wherein the non-solvent is selected from the group consisting of aliphatic petroleum distillates, naphthas, paraffinic solvents, hydro-treated petroleum distillates, mineral oil, mineral spirits, ligroin, decane, octane, and hexane.

30. The developing solvent of claim 29 , wherein the paraffinic solvents are isoparafins.

31. The developing solvent of claim 19 , wherein the developing solvent further comprising a co-solvent and a non-solvent.

32. The developing solvent of claim 31 , wherein the co-solvent is selected from the group consisting of n-butanol, 2-ethoxyethanol, benzyl alcohol, ethanol, methanol, propanol, isopropanol, alpha terpineol, dipropylene glycol methyl ether, 2-butoxyethanol, isopropyl alcohol, and 2-(2-butoxyethoxy) ethanol, cyclopentanol, cyclohexanol, cycloheptanol, substituted cyclopentanol, substituted cyclohexanol, substituted cycloheptanol, cyclopentyl substituted alcohol, cyclohexyl substituted alcohol, and cycloheptyl substituted alcohol.

33. The developing solvent of claim 31 , wherein the non-solvent is selected from the group consisting of aliphatic petroleum distillates, naphthas, paraffinic solvents, hydro-treated petroleum distillates, mineral oil, mineral spirits, ligroin, decane, octane, and hexane.

34. The developing solvent of claim 33 , wherein the paraffinic solvents are isoparaffins.

35. The developing solvent of claim 31 , wherein the substitute benzene is present in an amount of about 40-70% by volume, the co-solvent is present in an amount of about 20-50% by volume, and the non-solvent is present in an amount of about 10-30% by volume.

36. The method of claim 4 , wherein the co-solvent stabilizes the developing solvent.

Assignments (11)
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: 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.; QUALEX, INC.; KODAK PHILIPPINES, LTD.; NPEC, INC.; CREO MANUFACTURING AMERICA LLC; KODAK AVIATION LEASING LLC
Reel/Frame 050239/0001 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT (FIRST LIEN) Recorded Sep 5, 2013
From: QUALEX INC.; EASTMAN KODAK COMPANY; FAR EAST DEVELOPMENT LTD.; FPC INC.; KODAK (NEAR EAST), INC.; 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; KODAK AMERICAS, LTD.
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE
Reel/Frame 031158/0001 →
RELEASE OF SECURITY INTEREST IN PATENTS Recorded Sep 5, 2013
From: CITICORP NORTH AMERICA, INC., AS SENIOR DIP AGENT; WILMINGTON TRUST, NATIONAL ASSOCIATION, AS JUNIOR DIP AGENT
To: EASTMAN KODAK COMPANY; PAKON, INC.
Reel/Frame 031157/0451 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT (SECOND LIEN) Recorded Sep 5, 2013
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; PAKON, INC.; QUALEX INC.; KODAK PHILIPPINES, LTD.; NPEC INC.; CREO MANUFACTURING AMERICA LLC; KODAK AVIATION LEASING LLC
To: BARCLAYS BANK PLC, AS ADMINISTRATIVE AGENT
Reel/Frame 031159/0001 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT (ABL) Recorded Sep 5, 2013
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; PAKON, INC.; QUALEX INC.; KODAK PHILIPPINES, LTD.; NPEC INC.; CREO MANUFACTURING AMERICA LLC; KODAK AVIATION LEASING LLC
To: BANK OF AMERICA N.A., AS AGENT
Reel/Frame 031162/0117 →
PATENT SECURITY AGREEMENT Recorded Apr 1, 2013
From: EASTMAN KODAK COMPANY; PAKON, INC.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS AGENT
Reel/Frame 030122/0235 →
SECURITY INTEREST Recorded Feb 21, 2012
From: EASTMAN KODAK COMPANY; PAKON, INC.
To: CITICORP NORTH AMERICA, INC., AS AGENT
Reel/Frame 028201/0420 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 10, 2009
From: NUPRO TECHNOLOGIES, INC.
To: EASTMAN KODAK COMPANY
Reel/Frame 022231/0931 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 12, 2006
From: HENDRICKSON, CONSTANCE M.; BRADFORD, DAVID C.
To: NUPRO TECHNOLOGIES
Reel/Frame 018093/0953 →
Continuity (1)
Related Publication 20060057498A1 · Mar 16, 2006