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Photopolymerizable recording materials containing a triazole sensitizer and photoresist layers and lithographic printing plates based thereon

Assignee: Agfa Gevaert AG
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Filing: 1988-05-17
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Granted: 1990-10-09
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Expires: 2008-05-17
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Abstract

Abstract Novel photopolymerizable recording materials suitable in particular for producing photoresist layers and lithographic printing plates are composed of one or more photopolymerizable, olefinically unsaturated organic compounds, optionally a polymeric binder, a photopolymerization initiator, a color-forming system composed of a color former and a photooxidant, a certain benzotriazole compound as a sensitizer and optionally further additive and/or auxiliary substances.

Inventors

  • 👤 Reinhard Aldag
  • 👤 Peter Neumann
  • 👤 Andreas Boettcher
  • 👤 Thomas Bluemel
  • 👤 Friedrich Seitz

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-03 23:22
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/027; G03F7/028; G03F7/031

Claims Analysis

Total Claims: 17
Claim 1
Independent Claim 568 words
A photopolymerizable recording material composed of one or more photopolymerizable olefinically unsaturated organic compounds, a polymeric binder, one or more photopolymerization initiators, a color-forming system which on irradiation with actinic light causes an increase in the color intensity of the recording material, a sensitizer and further auxiliary substances, wherein the sensitizer comprises one or more compounds of the formula I ##STR22## where A is one of the radicals of the formulae (II) to (IV) ##STR23## R is hydrogen or C 1 -C 8 R 1 is C 1 -C 12 -alkyl, C 1 -C 12 -alkoxy, phenyl or an NR 5 R 6 group where R 5 and R 6 are identical to or different from each other and each is C 1 -C 12 -alkyl; allyl; phenylalkyl having 1 to 4 carbon atoms in the alkyl group; phenyl; phenyl substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or halogen; C 1 -C 12 -alkyl substituted by OH--, halogen-, CN--, --O--CO-alkyl having 1 to 6 carbon atoms in the alkyl group or --CO--O-alkyl having 1 to 6 carbons in the alkyl group; oxaalkyl of 3 to 12 carbon atoms and 1 to 5 oxygen atoms; or R 5 and R 6 carbon atoms and 1 to 5 oxygen atoms; or R 5 and R 6 together form a julolidine, carbazole, morpholine, piperidine or N-alkyl-piperidine radical, R 2 is hydrogen, C 1 -C 12 -alkyl, C 1 -C 12 -alkoxy, halogen or trialkylsilyl, n is 1 or 2, R 3 and R 4 are identical to or different from each other and each is C 1 -C 8 -alkyl, cycloalkyl, CO 2 R 7 where R 7 is C 1 -C 8 -alkyl, cycloalkyl, CO 2 R 7 where R 7 is C 1 -C 12 -alkyl; aryl; phenyl; or phenyl substituted by halogen, C 1 -C 12 -alkyl- or C 1 -C 4 -alkoxy; or R 3 and R 4 together form a carbocyclic or heterocyclic saturated or unsaturated fused ring system which is monosubstituted or polysubstituted by halogen; OH; CN; --O--CO-alkyl having 1 to 6 carbon atoms in the alkyl group; --CO--O-alkyl having 1 to 8 carbon atoms in the alkyl groupl trifluoromethyl; C 3 -C 6 -cycloalkyl; C 1 -C 8 -alkoxy; phenylalkyl having 1 to 4 carbon atoms in the alkyl gorup; C 1 -C 12 -alkyl; C 1 -C 12 -alkyl substituted by OH-, halogen-, CN--, --O--CO-alkyl- having 1 to 6 carbon atoms in the alkyl group, or --CO--O-alkyl having 1 to 6 carbon atoms in the alkyl group; oxaalkyl containing 2 to 12 carbon atoms and 1 to 6 oxygen atoms; trialkylsilyl having 1-4 carbons in the alkyl groups; or NR 8 R 9 , where R 8 and R 9 are identical to or different from each other and each is C 1 -C 8 -alkyl; C 1 -C 8 -alkyl substituted by OH, halogen-, CN--, --O--CO-alkyl having 1 to 6 carbon atoms in the alkyl group or --CO--O-alkyl having 1 to 6 carbon atoms in the alkyl group; oxaalkyl containing 3 to 12 carbon atoms and 1 to 5 oxygen atoms; phenylalkyl having 1 to 4 carbon atoms in the alkyl group; phenyl; or phenyl substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy- or halogen, with the proviso that the maximum of the long-wave absorption band of these compounds is below 420 nm.
Claim 2
Dependent Claim 568 words
A photopolymerizable recording material composed of one or more photopolymerizable olefinically unsaturated organic compounds, a polymeric binder, one or more photopolymerization initiators, a color-forming system which on irradiation with actinic light causes an increase in the color intensity of the recording material, a sensitizer and further auxiliary substances, wherein the sensitizer comprises one or more compounds of the formula I ##STR22## where A is one of the radicals of the formulae (II) to (IV) ##STR23## R is hydrogen or C 1 -C 8 R 1 is C 1 -C 12 -alkyl, C 1 -C 12 -alkoxy, phenyl or an NR 5 R 6 group where R 5 and R 6 are identical to or different from each other and each is C 1 -C 12 -alkyl; allyl; phenylalkyl having 1 to 4 carbon atoms in the alkyl group; phenyl; phenyl substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or halogen; C 1 -C 12 -alkyl substituted by OH--, halogen-, CN--, --O--CO-alkyl having 1 to 6 carbon atoms in the alkyl group or --CO--O-alkyl having 1 to 6 carbons in the alkyl group; oxaalkyl of 3 to 12 carbon atoms and 1 to 5 oxygen atoms; or R 5 and R 6 carbon atoms and 1 to 5 oxygen atoms; or R 5 and R 6 together form a julolidine, carbazole, morpholine, piperidine or N-alkyl-piperidine radical, R 2 is hydrogen, C 1 -C 12 -alkyl, C 1 -C 12 -alkoxy, halogen or trialkylsilyl, n is 1 or 2, R 3 and R 4 are identical to or different from each other and each is C 1 -C 8 -alkyl, cycloalkyl, CO 2 R 7 where R 7 is C 1 -C 8 -alkyl, cycloalkyl, CO 2 R 7 where R 7 is C 1 -C 12 -alkyl; aryl; phenyl; or phenyl substituted by halogen, C 1 -C 12 -alkyl- or C 1 -C 4 -alkoxy; or R 3 and R 4 together form a carbocyclic or heterocyclic saturated or unsaturated fused ring system which is monosubstituted or polysubstituted by halogen; OH; CN; --O--CO-alkyl having 1 to 6 carbon atoms in the alkyl group; --CO--O-alkyl having 1 to 8 carbon atoms in the alkyl groupl trifluoromethyl; C 3 -C 6 -cycloalkyl; C 1 -C 8 -alkoxy; phenylalkyl having 1 to 4 carbon atoms in the alkyl gorup; C 1 -C 12 -alkyl; C 1 -C 12 -alkyl substituted by OH-, halogen-, CN--, --O--CO-alkyl- having 1 to 6 carbon atoms in the alkyl group, or --CO--O-alkyl having 1 to 6 carbon atoms in the alkyl group; oxaalkyl containing 2 to 12 carbon atoms and 1 to 6 oxygen atoms; trialkylsilyl having 1-4 carbons in the alkyl groups; or NR 8 R 9 , where R 8 and R 9 are identical to or different from each other and each is C 1 -C 8 -alkyl; C 1 -C 8 -alkyl substituted by OH, halogen-, CN--, --O--CO-alkyl having 1 to 6 carbon atoms in the alkyl group or --CO--O-alkyl having 1 to 6 carbon atoms in the alkyl group; oxaalkyl containing 3 to 12 carbon atoms and 1 to 5 oxygen atoms; phenylalkyl having 1 to 4 carbon atoms in the alkyl group; phenyl; or phenyl substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy- or halogen, with the proviso that the maximum of the long-wave absorption band of these compounds is below 420 nm.
Claim 3
Dependent Claim 45 words
A photopolymerizable recording material as defined in claim 1, wherein the sensitizer comprises a compound of the formula (I) where A is a radical of the formula (II), R 1 is para relative to the linkage site with the triazole ring, and n is 1.
Claim 4
Dependent Claim 63 words
A photopolymerizable recording material as defined in claim 1, wherein the sensitizer comprises a compound of the formula (I) where A is the radical of the formula (II) and R 1 is --NR 5 R 6 where R 5 and R 6 are as defined in claim 1 and R 3 and R 4 together form a substituted or unsubstituted aromatic ring system.
Claim 5
Dependent Claim 37 words
A photopolymerizable recording material as defined in claim 1, wherein the sensitizer comprises a compound of the formula (V) ##STR24## where R 5 and R 6 are as defined in claim 1 and R 10 is halogen.
Claim 6
Dependent Claim 60 words
A photopolymerizable recording material as defined in claim 1, wherein the color-forming system which on irradiation with actinic light causes an increase in the color intensity of the recording material comprises (a) one or more colorless or virtually colorless organic compounds which are oxidizable to colored compounds, and (b) a photooxidant for the colorless or virtually colorless organic compound(s) (a).
Claim 7
Dependent Claim 20 words
A photopolymerizable recording material as defined in claim 5, wherein the photopolymerization initiator or photooxidant comprises one or more hexaarylbisimidazolyls.
Claim 8
Dependent Claim 18 words
A photopolymerizable recording material as defined in claim 5, where photooxidant (b) comprises one or more N-alkoxypyridinium salts.
Claim 9
Dependent Claim 37 words
A photopolymerizable recording material as defined in claim 1, wherein the colorless or virtually colorless organic compound which is oxidizable to a colored compound comprises a leuco dye, in particular a triarylmethane dye in its leuco form.
Claim 10
Dependent Claim 37 words
A photopolymerizable recording material as defined in claim 5, wherein the colorless or virtually colorless organic compound which is oxidizable to a colored compound comprises a leuco dye, in particular a triarylmethane dye in its leuco form.
Claim 11
Dependent Claim 14 words
A photoresist layer based on a photopolymerizable recording material as defined in claim 1.
Claim 12
Dependent Claim 14 words
A photoresist layer based on a photopolymerizable recording material as claimed in claim 5.
Claim 13
Dependent Claim 14 words
A photoresist layer based on a photopolymerizable recording material as defined in claim 6.
Claim 14
Dependent Claim 14 words
A photoresist layer based on a photopolymerizable recording material as defined in claim 7.
Claim 15
Dependent Claim 15 words
A lithographic printing plate based on a photopolymerizable recording material as claimed in claim 1.
Claim 16
Dependent Claim 15 words
A lithographic printing plate based on a photopolymerizable recording material as defined in claim 5.
Claim 17
Dependent Claim 24 words
A photopolymerizable recording material as defined in claim 1, wherein the maximum of the longwave absorption band of the compounds is below 400 nm.

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1993-10-08 1994-04-09 1994-10-09 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1997-10-08 1998-04-09 1998-10-09 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2001-10-08 2002-04-09 2002-10-09 $7700.00 Window Closed / Lapsed

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