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US4126468A Expired / Lapsed US ⏱️ 0.0 years remaining

Radiation sensitive compositions of quaternary ammonium salt and carboxylic acid sensitizer

Assignee: EIDP Inc
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Filing: 1977-04-18
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Granted: 1978-11-21
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Expires: 1997-04-18
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Abstract

Abstract A radiation sensitive composition comprises a quaternary ammonium salt and a chemical sensitiser of the formula ##STR1## wherein R 21 is aryl, arylakenyl or arylalkyl, R 22 is aryl, alkyl, arylalkenyl, arylalkyl, carboxylic acid or salt, or hydrogen and X is carboxylic acid or salt. The quaternary ammonium salt is of the type which will accept at least one electron on exposure to radiation to form a substance capable of causing metal to be deposited onto said substance from an electroless plating solution in contact with said substance and comprising a salt of said metal and a reducing agent. A radiation sensitive plate comprises a metallic substrate coated with a radiation sensitive layer comprising a quaternary ammonium salt. The layer may be formed of the above composition. A lithographic printing plate is produced by image-wise exposing the plate, contacting the plate with an electroless plating solution and, if necessary, rendering the resultant image areas more oleophilic and the resultant non-image areas more hydrophilic.

Inventors

  • 👤 John M. Kitteridge
  • 👤 Robert J. Armstrong

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-29 17:22
CPC Classifications
G; G03; G03C; G03C5/00; G03C5/58; G03C1/00; G03C1/72; G03C1/73; G03F; G03F7/00; G03F7/004

Claims Analysis

Total Claims: 21
Claim 1
Independent Claim 262 words
A radiation sensitive composition comprising (i) a quaternary ammonium salt of the type which will accept at least one electron on exposure to radiation to form a substance capable of causing metal to be deposited onto said substance from an electroless plating solution in contact with said substance and comprising a salt of said metal and a reducing agent, said quaternary ammonium salt having the general formula ##STR5## wherein R 1 to R 10 are hydrogen or halogen atoms or organic substituents; R 11 and R 12 , if present, are each halogen atoms or organic substituents or together represent a divalent organic substituent; Z is zero or an integer; X - is an anion; m=1 or 2; and at least one of the nitrogen atoms is quaternary; provided that R 11 and R 12 are not each --CH 3 groups or are not together a --CH 2 CH 2 -- group when each of R 1 to R 10 is a hydrogen atom and Z is zero, and (ii) a chemical sensitiser for improving the speed of photoreduction of the quaternary ammonium salt, said sensitiser having the general formula ##STR6## wherein R 21 is substituted or unsubstituted aryl group, an arylalkenyl group, or an arylalkyl group; R 22 is a substituted or unsubstituted aryl group, an alkyl group, an arylalkyl group, an arylalkenyl group, a carboxylic acid group, a carboxylic acid salt group, or a hydrogen atom; or R 21 and R 22 together represent a bivalent species; and X represents a carboxylic acid group or a carboxylic acid salt group.
Claim 2
Dependent Claim 262 words
A radiation sensitive composition comprising (i) a quaternary ammonium salt of the type which will accept at least one electron on exposure to radiation to form a substance capable of causing metal to be deposited onto said substance from an electroless plating solution in contact with said substance and comprising a salt of said metal and a reducing agent, said quaternary ammonium salt having the general formula ##STR5## wherein R 1 to R 10 are hydrogen or halogen atoms or organic substituents; R 11 and R 12 , if present, are each halogen atoms or organic substituents or together represent a divalent organic substituent; Z is zero or an integer; X - is an anion; m=1 or 2; and at least one of the nitrogen atoms is quaternary; provided that R 11 and R 12 are not each --CH 3 groups or are not together a --CH 2 CH 2 -- group when each of R 1 to R 10 is a hydrogen atom and Z is zero, and (ii) a chemical sensitiser for improving the speed of photoreduction of the quaternary ammonium salt, said sensitiser having the general formula ##STR6## wherein R 21 is substituted or unsubstituted aryl group, an arylalkenyl group, or an arylalkyl group; R 22 is a substituted or unsubstituted aryl group, an alkyl group, an arylalkyl group, an arylalkenyl group, a carboxylic acid group, a carboxylic acid salt group, or a hydrogen atom; or R 21 and R 22 together represent a bivalent species; and X represents a carboxylic acid group or a carboxylic acid salt group.
Claim 3
Dependent Claim 15 words
A composition according to claim 1 wherein the quaternary ammonium salt is N,N'-bis-(paracyano phenyl)-,4,4'-bipyridylium salt.
Claim 4
Dependent Claim 14 words
A composition according to claim 1 in which the chemical sensitiser is mandelic acid.
Claim 5
Dependent Claim 16 words
A composition according to claim 1 in which the chemical sensitiser is a mandelic acid derivative.
Claim 6
Dependent Claim 17 words
A composition according to claim 4 in which the derivative is p-bromo mandelic acid or ammonium mandelate.
Claim 7
Dependent Claim 38 words
A composition according to claim 4 in which the derivative is p-chloro mandelic acid, p-fluoromandelic acid, m-methoxy mandelic acid, o-methoxy mandelic acid, p-methoxy mandelic acid, m-nitro mandelic acid, sodium mandelate, tetramethyl ammonium p-fluoro mandelate, or hexamethylene tetramine mandelate.
Claim 8
Dependent Claim 14 words
A composition according to claim 1 in which the chemical sensitiser is benzilic acid.
Claim 9
Dependent Claim 17 words
A composition according to claim 1 in which the chemical sensitiser is a derivative of benzilic acid.
Claim 10
Dependent Claim 18 words
A composition according to claim 8 wherein the derivative is 3,4-dimethoxy 2'-chloro benzilic acid or di-p-methoxy benzilic acid.
Claim 11
Dependent Claim 29 words
A composition according to claim 1 wherein the chemical sensitiser is 3-phenyl lactic acid, atrolactic acid, potassium atrolactate, 9-hydroxy fluorene -9-carboxylic acid, styryl glycollic acid, or 1-naphthyl glycollic acid
Claim 12
Dependent Claim 228 words
A radiation sensitive composition comprising (i) a quaternary ammonium salt of the type which will accept at least one electron on exposure to radiation to form a substance capable of causing metal to be deposited onto said substance from an electroless plating solution in contact with said substance and comprising a salt of said metal and reducing agent, said quaternary ammonium salt having the general formula: ##STR7## wherein R 1 to R 10 are hydrogen or halogen atoms or organic substitutents; R 11 and R 12 , if present, are each halogen atoms or organic substituents or together represent a divalent organic substituent; Z is zero or an integer; X - is an anion; m=1 or 2; and at least one of the nitrogen atoms is quaternary, and (ii) a chemical sensitiser having the general formula ##STR8## wherein R 21 is a substituted or unsubstituted aryl group, an arylalkenyl group or an aryl alkyl group; R 22 is a substituted or unsubstituted aryl group, an alkyl group, an aryl alkyl group, an aryl alkenyl group, a carboxylic acid group, a carboxylic acid salt group, or a hydrogen atom provided that R 21 is not a phenyl group when R 22 is a phenyl group; or R 21 and R 22 together represent a bivalent species; and X represents a carboxylic acid group, or a carboxylic acid salt group.
Claim 13
Dependent Claim 228 words
A radiation sensitive composition comprising (i) a quaternary ammonium salt of the type which will accept at least one electron on exposure to radiation to form a substance capable of causing metal to be deposited onto said substance from an electroless plating solution in contact with said substance and comprising a salt of said metal and reducing agent, said quaternary ammonium salt having the general formula: ##STR7## wherein R 1 to R 10 are hydrogen or halogen atoms or organic substitutents; R 11 and R 12 , if present, are each halogen atoms or organic substituents or together represent a divalent organic substituent; Z is zero or an integer; X - is an anion; m=1 or 2; and at least one of the nitrogen atoms is quaternary, and (ii) a chemical sensitiser having the general formula ##STR8## wherein R 21 is a substituted or unsubstituted aryl group, an arylalkenyl group or an aryl alkyl group; R 22 is a substituted or unsubstituted aryl group, an alkyl group, an aryl alkyl group, an aryl alkenyl group, a carboxylic acid group, a carboxylic acid salt group, or a hydrogen atom provided that R 21 is not a phenyl group when R 22 is a phenyl group; or R 21 and R 22 together represent a bivalent species; and X represents a carboxylic acid group, or a carboxylic acid salt group.
Claim 14
Dependent Claim 14 words
A composition according to claim 11 in which the chemical sensitiser is mandelic acid.
Claim 15
Dependent Claim 16 words
A composition according to claim 11 in which the chemical sensitiser is a mandelic acid derivative.
Claim 16
Dependent Claim 17 words
A composition according to claim 13 in which the derivative is p-bromo mandelic acid or ammonium mandelate.
Claim 17
Dependent Claim 37 words
A composition according to claim 13 in which the derivative is p-chloro mandelic acid, p-fluoromandelic acid, m-methoxy mandelic acid, o-methoxy mandelic acid, p-methoxy mandelic acid, m-nitro, mandelic acid, sodium mandelate, tetramethyl ammonium p-fluoromandelate or hexamethylene tetramine mandelate.
Claim 18
Dependent Claim 19 words
A composition according to claim 11 in which the sensitiser is 3,4-dimethoxy 2'-chloro benzilic acid or di-p-methoxy benzilic acid.
Claim 19
Dependent Claim 29 words
A composition according to claim 11 in which the chemical sensitiser is 3-phenyl lactic acid, atrolactic acid, potassium atrolactate, 9-hydroxy fluorene-9-carboxylic acid, styryl glycollic acid, or 1-naphthyl glycollic acid.
Claim 20
Dependent Claim 77 words
A composition according to claim 11 in which the quaternary ammonium salt has the general formula: ##STR9## wherein R 1 to R 10 are hydrogen or halogen atoms or organic substituents; R 11 and R 12 , if present, are each halogen atoms or organic substituents or together represent a divalent organic substituent; z is zero or an integer; X - is an anion; m=1 or 2; and at least one of the nitrogen atoms is quaternary.
Claim 21
Dependent Claim 24 words
A composition according to claim 18 wherein the quaternary ammonium salt is selected from the group consisting of paraquat, diquat, and an N,N'-bis-(paracyanophenyl)-4,4'-bipyridilium salt.

References Cited (Backward Citations)

US3316093A Cited
US3671250A Cited
US3954471A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1981-11-20 1982-05-22 1982-11-21 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1985-11-20 1986-05-22 1986-11-21 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1989-11-20 1990-05-22 1990-11-21 $7700.00 Window Closed / Lapsed

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