US5055376A
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Curable compositions containing onium salt photoinitiators which have a chromophore linked to the onium salt moiety through the 3-position and method of use
Assignee: Eastman Kodak Co
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Filing: 1990-11-13
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Granted: 1991-10-08
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Expires: 2010-11-13
Abstract
Abstract Compositions of matter are provided which comprise a material curable by a Bronsted acid, and a photoinitiator salt having the formula: ##STR1## wherein: R 1 represents an electron-donating chromophore group which absorbs visible radiation and which exhibits a higher energy occupied molecular orbital than at least one of R", R'" and R""; R" represents the same substituent as R' or R'", an optionally substituted aryl group or an optionally substituted alkyl group having from 1 to 18 carbon atoms; R'" represents an electron-withdrawing alkyl, aryl or heterocyclic group; R 1 and R 2 each, independently, represents hydrogen or an electron-donating group; J represents an S, Se, As, N or P atom; and when J represents As, N or P, R"" represents the same substituent as R', R" or R'", and when J represents an S or Se atom, R"" represents O or an electron pair; and W.sup.Θ represents an anion capable of forming a Bronsted acid having a pKa of less than 7, said photoinitiator salt being capable, upon exposure to visible radiation of a wavelength absorbed by said chromophore, of forming a Bronsted acid. The invention also relates to the use of said compositions.
Inventors
- 👤 Franklin D. Saeva
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 15:10
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
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
181 words
A composition of matter comprising a material curable by a Bronsted acid, and a salt having the following formula: ##STR9## wherein: R' represents an electron-donating chromophore group which absorbs visible radiation, and which exhibits a higher energy occupied molecular orbital than at least one of R", R'" and R""; R" represents the same substituent as R' or R'", an optionally substituted aryl group or an optionally substituted alkyl group having from 1 to 18 carbon atoms; R'" represents an electron-withdrawing alkyl, aryl or heterocyclic group; R 1 and R 2 each, independently, represents hydrogen or an electron-donating group; J represents an S, Se, As, N or P atom; and when J represent As, N or P, R"" represents the same substituent as R', R" or R'" and, when J represents a S or Se atom, R"" represents O or an electron pair; and, W.sup.Θ represents an anion capable of forming a Bronsted acid having a pKa of less than 7, said compound being capable, upon exposure to visible radiation of a wavelength absorbed by said chromophore, of forming a Bronsted acid.
Claim 2
Dependent Claim
181 words
A composition of matter comprising a material curable by a Bronsted acid, and a salt having the following formula: ##STR9## wherein: R' represents an electron-donating chromophore group which absorbs visible radiation, and which exhibits a higher energy occupied molecular orbital than at least one of R", R'" and R""; R" represents the same substituent as R' or R'", an optionally substituted aryl group or an optionally substituted alkyl group having from 1 to 18 carbon atoms; R'" represents an electron-withdrawing alkyl, aryl or heterocyclic group; R 1 and R 2 each, independently, represents hydrogen or an electron-donating group; J represents an S, Se, As, N or P atom; and when J represent As, N or P, R"" represents the same substituent as R', R" or R'" and, when J represents a S or Se atom, R"" represents O or an electron pair; and, W.sup.Θ represents an anion capable of forming a Bronsted acid having a pKa of less than 7, said compound being capable, upon exposure to visible radiation of a wavelength absorbed by said chromophore, of forming a Bronsted acid.
Claim 3
Dependent Claim
18 words
A composition of matter as defined in claim 1 wherein, in said formula, J represents an S atom.
Claim 4
Dependent Claim
83 words
A composition of matter as defined in claim 1 wherein, in said structural formula, R' represents one of the following chromophores: ##STR10## J, R", R'" and R"", taken together, represent one of the following groups: ##STR11## wherein Ar represents an optionally substituent aryl group; and W represents BF 4 , ClO 4 , AsF 6 , PF 6 , CF 3 SO 3 , CH 3 SO 3 , SnCl 4 , FeCl 4 , BiCl 4 or SbF 6 , or p-toluenesulfonate.
Claim 5
Dependent Claim
22 words
A material useful for forming printed circuit boards comprising a conductive substrate leaving coated thereon a composition as defined in claim 1.
Claim 6
Dependent Claim
35 words
A material useful for forming printed circuit boards as defined in claim 4 which comprises a copper substrate having thereon a layer containing about 90% by weight poly(4-t-butylphenylcarbonate) and about 10% by weight 4-cyanobenzyl-3-[5-naphthacenyl]phenylmethylsulfonium trifluoromethanesulfonate.
Claim 7
Dependent Claim
19 words
A composition of matter comprising about 10% by weight of 4-cyanobenzyl-3-[5-naphthacenyl]-phenylmethylsulfonium hexafluorophosphate and about 90% by weight polyvinyl(4-t-butylphenyl carbonate).
Claim 8
Dependent Claim
19 words
A composition of matter comprising about 10% by weight of 4-cyanobenzyl-3-[5-naphthacenyl]-phenylmethylsulfonium hexafluorophosphate and about 90% by weight polyvinyl(4-t-butylphenyl carbonate).
Claim 9
Independent Claim
209 words
A method of forming images which comprises: A) exposing to visible radiation (1) a material curable by a Bronsted acid and (2) a compound having the formula: ##STR12## wherein: R' represents an electron-donating chromophore group which absorbs said visible radiation, and which exhibits a higher energy occupied molecular orbital than at least one of R", R'" and R""; R" represents the same substituent as R' or R'", an optionally substituted aryl group or an optionally substituted alkyl group having from 1 to 18 carbon atoms; R'" represents an electron-withdrawing alkyl, aryl or heterocyclic group; R 1 and R 2 each, independently, represents hydrogen or an electron-donating group; J represents an S, Se, As, N or P atom; and when J represents As, N or P, R"" represents the same substituent as R', R" or R'" and, when J represents an S or Se atom, R"" represents O or an electron pair; and, W.sup.Θ represents an anion capable of forming a Bronsted acid having a pKa of less than 7, said compound being capable, upon exposure to visible said radiation, of forming a Bronsted acid; B) curing said material in the area exposed to said radiation; and C) selectively removing the uncured material in the areas not exposed to radiation.
Claim 10
Independent Claim
209 words
A method of forming images which comprises: A) exposing to visible radiation (1) a material curable by a Bronsted acid and (2) a compound having the formula: ##STR12## wherein: R' represents an electron-donating chromophore group which absorbs said visible radiation, and which exhibits a higher energy occupied molecular orbital than at least one of R", R'" and R""; R" represents the same substituent as R' or R'", an optionally substituted aryl group or an optionally substituted alkyl group having from 1 to 18 carbon atoms; R'" represents an electron-withdrawing alkyl, aryl or heterocyclic group; R 1 and R 2 each, independently, represents hydrogen or an electron-donating group; J represents an S, Se, As, N or P atom; and when J represents As, N or P, R"" represents the same substituent as R', R" or R'" and, when J represents an S or Se atom, R"" represents O or an electron pair; and, W.sup.Θ represents an anion capable of forming a Bronsted acid having a pKa of less than 7, said compound being capable, upon exposure to visible said radiation, of forming a Bronsted acid; B) curing said material in the area exposed to said radiation; and C) selectively removing the uncured material in the areas not exposed to radiation.
Claim 11
Dependent Claim
20 words
A method of forming images as defined in claim 7 wherein, in said structural formula, J represents an S atom.
Claim 12
Independent Claim
34 words
A method of forming images which comprises exposing to visible laser radiation having a wavelength of about 488-515 nm a composition comprising about 90% by weight poly(4-t-butylphenyl-carbonate) and about 10% by weight 4-cyanobenzyl-3-[5-naphthacenyl]phenyl-n-butylsulfonium hexafluorophosphate.
Claim 13
Independent Claim
34 words
A method of forming images which comprises exposing to visible laser radiation having a wavelength of about 488-515 nm a composition comprising about 90% by weight poly(4-t-butylphenyl-carbonate) and about 10% by weight 4-cyanobenzyl-3-[5-naphthacenyl]phenyl-n-butylsulfonium hexafluorophosphate.
Claim 14
Dependent Claim
204 words
A printing plate comprising a substrate having coated thereon a layer comprising: a material (1) curable by a Bronsted acid, (2) capable of being inked and (3) capable of transferring ink to a substrate; and a compound having the formula: ##STR13## wherein: R' represents an electron-donating chromophore group which absorbs visible radiation, has a removable positive hydrogen ion, and exhibits a higher energy occupied molecular orbital than at least one of R", R'" and R""; R" represents the same substituent as R' or R'", an optionally substituted aryl group or an optionally substituted alkyl group; R'" represents an electron withdrawing alkyl, aryl or heterocyclic group; R 1 and R 2 each, independently, represents hydrogen or an electron-donating group; J represents a sulfur or arsenic atom; when J represents As, R"" represents the same substituent as R', R" or R'" and, when J represents a sulfur atom, R"" represent O or an electron pair; and, W.sup.Θ represents an anion capable of forming a Bronsted acid having a pKa of less than 7; said compound being capable, upon exposure to visible radiation of a wavelength absorbed by said chromophore, of forming, by intramolecular rearrangement, a Bronsted acid comprising W and said removable positive hydrogen of R'.
Claim 15
Dependent Claim
204 words
A printing plate comprising a substrate having coated thereon a layer comprising: a material (1) curable by a Bronsted acid, (2) capable of being inked and (3) capable of transferring ink to a substrate; and a compound having the formula: ##STR13## wherein: R' represents an electron-donating chromophore group which absorbs visible radiation, has a removable positive hydrogen ion, and exhibits a higher energy occupied molecular orbital than at least one of R", R'" and R""; R" represents the same substituent as R' or R'", an optionally substituted aryl group or an optionally substituted alkyl group; R'" represents an electron withdrawing alkyl, aryl or heterocyclic group; R 1 and R 2 each, independently, represents hydrogen or an electron-donating group; J represents a sulfur or arsenic atom; when J represents As, R"" represents the same substituent as R', R" or R'" and, when J represents a sulfur atom, R"" represent O or an electron pair; and, W.sup.Θ represents an anion capable of forming a Bronsted acid having a pKa of less than 7; said compound being capable, upon exposure to visible radiation of a wavelength absorbed by said chromophore, of forming, by intramolecular rearrangement, a Bronsted acid comprising W and said removable positive hydrogen of R'.
Claim 16
Dependent Claim
31 words
A printing plate as defined in claim 10 which comprises an aluminum substrate having coated thereon a film comprising about 10% by weight 4-cyanobenzyl-3-[5-naphthacenyl]benzylphenyl trifluoromethanesulfonate and about 90% by weight polyvinyl-(4-t-butylphenylcarbonate).
References Cited (Backward Citations)
US4933377A
Cited
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1994-10-07 | 1995-04-08 | 1995-10-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1998-10-07 | 1999-04-08 | 1999-10-08 | $3760.00 | Window Closed / Lapsed |
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