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US4954414A Expired / Lapsed US ⏱️ 0.0 years remaining

Photosensitive composition containing a transition metal coordination complex cation and a borate anion and photosensitive materials employing the same

Assignee: Eastman Kodak Co
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Filing: 1988-11-08
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Granted: 1990-09-04
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Expires: 2008-11-08
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Abstract

Abstract A composition including a cationic transition metal coordination complex and a borate anion, wherein said composition is capable of absorbing actinic radiation and producing free radicals which can initiate free radical addition polymerization of a free radical addition polymerizable or crosslinkable monomer is disclosed. The compositions are particularly useful as visible light photoinitiators.

Inventors

  • 👤 Paul C. Adair
  • 👤 Peter Gottschalk

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-29 14:35
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/027; G03F7/028; G03F7/029; Y; Y10; Y10S; Y10S430/00; Y10S430/1053; Y10S430/1055; Y10S430/114; Y10S430/115; Y10S430/118; Y10S430/137

Claims Analysis

Total Claims: 40
Claim 1
Independent Claim 74 words
A photoinitiator including a cationic transition metal coordination complex and a borate anion wherein said borate anion is represented by the following formula: ##STR3## wherein R 1 , R 2 , R 3 and R 4 are the same or different and are selected from the group consisting of alkyl, aryl, aralkyl, alkaryl, alkenyl, alkynyl, alicyclic, heterocyclic, and allyl groups, and wherein said photoinitiator is capable of absorbing actinic radiation and producing free radicals.
Claim 2
Dependent Claim 74 words
A photoinitiator including a cationic transition metal coordination complex and a borate anion wherein said borate anion is represented by the following formula: ##STR3## wherein R 1 , R 2 , R 3 and R 4 are the same or different and are selected from the group consisting of alkyl, aryl, aralkyl, alkaryl, alkenyl, alkynyl, alicyclic, heterocyclic, and allyl groups, and wherein said photoinitiator is capable of absorbing actinic radiation and producing free radicals.
Claim 3
Dependent Claim 42 words
The photoinitiator according to claim 1 wherein three of said R 1 , R 2 , R 3 and R 4 groups are aryl and one of said R 1 , R 2 , R 3 and R 4 groups is alkyl.
Claim 4
Dependent Claim 54 words
The photoinitiator according to claim 2 wherein said cationic transition metal coordination complex is a complex of a transition metal atom having a d 6 orbital configuration and one or more ligands covalently bonded to said transition metal atom so that said complex is capable of underdoing metal to ligand charge transfer upon photoexcitation.
Claim 5
Dependent Claim 30 words
The photoinitiator according to claim 3 wherein said cationic transition metal coordination complex includes a transition metal selected from the group consisting of Re(I), Fe(II), Ru(II), Os(II), Co(III) and Ir(III).
Claim 6
Dependent Claim 23 words
The photoinitiator according to claim 4 wherein said cationic transition metal coordination complex and said borate anion are present as an ion pair.
Claim 7
Dependent Claim 21 words
The photoinitiator according to claim 5 wherein at least one of said ligands includes a heterocyclic group containing a nitrogen atom.
Claim 8
Dependent Claim 37 words
The photoinitiator according to claim 6 wherein at least one of said ligands is selected from the group consisting of pyridine, 2,2'-bipyridine, 4,4'-dimethyl-2,2'-bipyridine, 1,10-phenanthroline, 3,4,7,8-tetramethyl-1,10-phenanthroline, 2,2',2"-terpyridine, 5,6-dimethyl-1,10-phenanthroline, 5-methyl-1,10-phenanthroline, 5-chloro-1,10-phenanthroline, 5-nitro-1,10-phenanthroline, 4,7-dimethyl-1,10-phenanthroline and 2,4,6-tri(2-pyridyl-s-triazine and substituted derivatives thereof.
Claim 9
Dependent Claim 19 words
The photoinitiator according to claim 5 wherein one or more of said ligands is a bidentate or tridentate ligand.
Claim 10
Dependent Claim 35 words
The photoinitiator according to claim 1 wherein said photoinitiator is capable of absorbing actinic radiation and producing free radicals as a result of exposure to light emitted from a visible or near ultraviolet light source.
Claim 11
Dependent Claim 99 words
A photoresist material comprising a free radical addition polymerizable or crosslinkable compound and a photoinitiator including a cationic transition metal coordination complex and a borate anion wherein said borate anion is represented by the following formula: ##STR4## wherein R 1 , R 2 , R 3 and R 4 are the same or different and are selected from the group consisting of alkyl, aryl, aralkyl, alkaryl, alkenyl, alkynyl, alicyclic, heterocyclic, and allyl groups, and wherein said photoinitiator is capable of absorbing actinic radiation and producing free radicals which can initiate free radical polymerization of said polymerizable or crosslinkable compound.
Claim 12
Dependent Claim 99 words
A photoresist material comprising a free radical addition polymerizable or crosslinkable compound and a photoinitiator including a cationic transition metal coordination complex and a borate anion wherein said borate anion is represented by the following formula: ##STR4## wherein R 1 , R 2 , R 3 and R 4 are the same or different and are selected from the group consisting of alkyl, aryl, aralkyl, alkaryl, alkenyl, alkynyl, alicyclic, heterocyclic, and allyl groups, and wherein said photoinitiator is capable of absorbing actinic radiation and producing free radicals which can initiate free radical polymerization of said polymerizable or crosslinkable compound.
Claim 13
Dependent Claim 43 words
The material composition according to claim 10 wherein three of said R 1 , R 2 , R 3 and R 4 groups are aryl and one of said R 1 , R 2 , R 3 and R 4 groups is alkyl.
Claim 14
Dependent Claim 54 words
The material according to claim 10 wherein said cationic transition metal coordination complex is a complex of a transition metal atom having a d 6 orbital configuration and one or more ligands covalently bonded to said transition metal atom so that said complex is capable of undergoing metal to ligand charge transfer upon photoexcitation..
Claim 15
Dependent Claim 31 words
The material according to claim 12 wherein said cationic transition metal coordination complex includes a transition metal atom selected from the group consisting of Re(I), Fe(II), Ru(II), Os(II), Co(III) and Ir(III).
Claim 16
Dependent Claim 23 words
The material according to claim 13 wherein said cationic transition metal coordination complex and said borate anion are present as an ion pair.
Claim 17
Dependent Claim 21 words
The material according to claim 14 wherein at least one of said ligands includes a hetercyclic group containing a nitrogen atom.
Claim 18
Dependent Claim 37 words
The material according to claim 15 wherein at least one of said ligands is selected from the group consisting of pyridine, 2,2'-bipyridine, 4,4'-dimethyl-2,2'-bipyridine, 1,10-phenanthroline, 3,4,7,8-tetramethyl-1,10-phenanthroline, 2,2',2"-terpyridine, 5,6-dimethyl-1,10-phenanthroline, 5-methyl-1,10-phenanthroline, 5-chloro-1,10-phenanthroline, 5-nitro-1,10-phenanthroline, 4,7-dimethyl-1,10-phenanthroline and 2,4,6-tri(2-pyridyl-s-triazine) and substituted derivatives thereof.
Claim 19
Dependent Claim 19 words
The material according to claim 14 wherein at least one of said ligands is a bidentate or tridentate ligand.
Claim 20
Dependent Claim 32 words
The material according to claim 10 wherein said photoinitiator is capable of absorbing actinic radiation and producing free radicals as a result of exposure to light emitted from a visible light source.
Claim 21
Dependent Claim 14 words
The material according to claim 10 wherein said compound is an ethylenically unsaturated compound.
Claim 22
Dependent Claim 11 words
The material according to claim 10 wherein said composition is microencapsulated.
Claim 23
Dependent Claim 13 words
The material according to claim 20 wherein said photoinitiator additionally comprises an autoxidizer.
Claim 24
Dependent Claim 115 words
A photosensitive material comprising a support having a layer of a photohardenable composition on the surface thereof, said composition comprising a free radical addition polymerizable or crosslinkable compound and a photoinitiator including a cationic transition metal coordination complex and a borate anion wherein said borate anion is represented by the following formula: ##STR5## where R 1 , R 2 , R 3 and R 4 are the same or different and are selected from the group consisting of alkyl, aryl, aralkyl, alkaryl, alkenyl, alkynyl, alicyclic, heterocyclic, and allyl groups, and wherein said photoinitiator is capable of absorbing actinic radiation and producing free radicals which can initiate free radical polymerization of said polymerizable or crosslinkable compound.
Claim 25
Dependent Claim 115 words
A photosensitive material comprising a support having a layer of a photohardenable composition on the surface thereof, said composition comprising a free radical addition polymerizable or crosslinkable compound and a photoinitiator including a cationic transition metal coordination complex and a borate anion wherein said borate anion is represented by the following formula: ##STR5## where R 1 , R 2 , R 3 and R 4 are the same or different and are selected from the group consisting of alkyl, aryl, aralkyl, alkaryl, alkenyl, alkynyl, alicyclic, heterocyclic, and allyl groups, and wherein said photoinitiator is capable of absorbing actinic radiation and producing free radicals which can initiate free radical polymerization of said polymerizable or crosslinkable compound.
Claim 26
Dependent Claim 11 words
The material according to claim 22 wherein said composition is microencapsulated.
Claim 27
Dependent Claim 42 words
The material according to claim 22 wherein three of said R 1 , R 2 , R 3 and R 4 groups are aryl and one of said R 1 , R 2 , R 3 and R 4 groups is alkyl.
Claim 28
Dependent Claim 54 words
The material according to claim 25 wherein said cationic transition metal coordination complex is a complex of a transition metal atom having a d 6 orbital configuration and one or more ligands covalently bonded to said transition metal atom so that said complex is capable of undergoing metal to ligand charge transfer upon photoexcitation.
Claim 29
Dependent Claim 34 words
The material according to claim 25 wherein said cationic transition metal coordination complex is a complex of a transition metal atom selected from the group consisting of Re(I), Fe(II), Ru(II), Os(II), Co(III), and Ir(III).
Claim 30
Dependent Claim 23 words
The material according to claim 26 wherein said cationic transition metal coordination complex and said borate anion are present as an ion pair.
Claim 31
Dependent Claim 21 words
The material according to claim 26 wherein at least one of said ligands includes a heterocyclic group containing a nitrogen atom.
Claim 32
Dependent Claim 33 words
The material according to claim 26 wherein at least one of said ligands is selected from the group consisting of pyridine, 2,2'-bipyridine, 4,4'-dimethyl-2,2'-bipyridine, 1,10-phenanthroline, 3,4,7,8-tetramethyl-1,10-phenanthroline, 2,2',2"-terpyridine, 5,6-dimethyl-1,10-phenanthroline, 5-methyl-1,10-phenanthroline, 5-chloro-1,10-phenanthroline, 5-nitro-1,10-phenanthroline, 4,7-dimethyl-1,10-phenanthroline and 2,4,6-tri(2-pyridyl-s-triazine).
Claim 33
Dependent Claim 19 words
The material according to claim 26 wherein at least one of said ligands is a bidentate or tridentate ligand.
Claim 34
Dependent Claim 32 words
The material according to claim 22 wherein said photoinitiator is capable of absorbing actinic radiation and producing free radicals as a result of exposure to light emitted from a visible light source.
Claim 35
Dependent Claim 14 words
The material according to claim 23 wherein said composition additionally comprises an image-forming agent.
Claim 36
Dependent Claim 25 words
The material according to claim 32 wherein said image-forming agent comprises a colorless color-forming agent which forms an image upon contact with a developer material.
Claim 37
Dependent Claim 14 words
The material according to claim 33 wherein said compound comprises an ethylenically unsaturated compound.
Claim 38
Dependent Claim 74 words
The material according to claim 34 wherein said microcapsules include a first set of microcapsules having a cyan image-forming agent associated therewith, a second set of microcapsules having a magenta image-forming agent associated therewith and a third set of microcapsules having a yellow image-forming agent associated therewith, wherein at least one of said first, second and third sets of microcapsules contains said photoinitiator including said cationic transition metal coordination complex and said borate anion.
Claim 39
Dependent Claim 43 words
The material according to claim 35 wherein said microcapsules upon imagewise exposure to three distinct wavelengths of actinic radiation which respectively image-wise harden said first, second and third sets of microcapsules are capable of forming a full color image on a developer material.
Claim 40
Dependent Claim 18 words
The photosensitive material of claim 36 wherein said three distinct wavelengths correspond to red, green and blue light.

References Cited (Backward Citations)

EP0126712A1 Cited
EP0152377A2 Cited
US4707432A Cited
US4842980A Cited
US4772530A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1993-09-03 1994-03-05 1994-09-04 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1997-09-03 1998-03-05 1998-09-04 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2001-09-03 2002-03-05 2002-09-04 $7700.00 Window Closed / Lapsed

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