EP0331413A1
Expired / Lapsed
EP
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Novel sulfonium salts and the use thereof as photoinitiators
Assignee: Eastman Kodak Co
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Filing: 1989-02-28
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Granted: —
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Expires: 2009-02-28
Abstract
Abstract Sulfonium and oxysulfonium salts, useful as photoinitiators, are disclosed which have directly attached to the sulfur atom thereof: at least one aromatic or heterocyclic aromatic substituent containing at least 14 aromatic atoms and having a removable positive hydrogen ion, said substituent exhibiting a higher energy occupied molecular orbital than at least one other substituent directly attached to said sulfur atom; and at least one substituent comprising an electron withdrawing group and exhibiting a lower energy unoccupied molecular orbital than at least one other substituent directly attached to said sulfur atoms; said salts being capable, upon exposure to visible radiation, of undergoing irreversible intramolecular rearrangement to form a Bronsted acid comprising the anion of said salt and said removable positive hydrogen ion.
Inventors
- 👤 Franklin Donald Eastman Kodak Company Saeva
- 👤 David Thomas Eastman Kodak Company Breslin
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-10-31 04:15
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/027; G03F7/028; G03F7/029; C; C07; C07C; C07C381/00; C07C381/12; C07C2603/00; C07C2603/02; C07C2603/04; C07C2603/22; C07C2603/24; C07C2603/40; C07C2603/42; C07C2603/44; Y; Y10; Y10S; Y10S430/00; Y10S430/1053; Y10S430/1055; Y10S430/114; Y10S430/115; Y10S430/122; Y10S430/123
Claims Analysis
Total Claims: 8
Claim 1
Independent Claim
117 words
A sulfonium or oxysulfonium salt photoinitiator having directly attached to the sulfur atom thereof at least one aromatic or heterocyclic aromatic substituent containing a least 14 aromatic atoms and having a removable positive hydrogen ion, said substituent exhibiting a higher energy occupied molecular orbital than at least one other substituent directly attached to said sulfur atom; and at least one substituent comprising an electron withdrawing group and exhibiting a lower energy unoccupied molecular orbital than at least one other substituent directly attached to said sulfur atom; said salt being capable, upon exposure to visible radiation, of undergoing irreversible intramolecular rearrangement to form a Bronsted acid comprising the anion of said salt and said removable positive hydrogen ion.
Claim 2
Dependent Claim
117 words
A sulfonium or oxysulfonium salt photoinitiator having directly attached to the sulfur atom thereof at least one aromatic or heterocyclic aromatic substituent containing a least 14 aromatic atoms and having a removable positive hydrogen ion, said substituent exhibiting a higher energy occupied molecular orbital than at least one other substituent directly attached to said sulfur atom; and at least one substituent comprising an electron withdrawing group and exhibiting a lower energy unoccupied molecular orbital than at least one other substituent directly attached to said sulfur atom; said salt being capable, upon exposure to visible radiation, of undergoing irreversible intramolecular rearrangement to form a Bronsted acid comprising the anion of said salt and said removable positive hydrogen ion.
Claim 3
Dependent Claim
133 words
A photoinitiator according to claim 1 having the formula: wherein R′ represents an electron donating aromatic or heterocyclic aromatic substituent having at least 14 atoms in the aromatic ring and having a removable positive hydrogen ion bonded to one of the aromatic atoms; R˝ represents the same substituent as R′ or R‴, or an optionally substituted phenyl group, naphthyl group or alkyl group having from 1 to 18 carbon atoms; R‴ represents an electron withdrawing alkyl, aryl or heterocyclic group; R′′′′ represents an electron pair or oxygen; W- 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 undergoing irreversible intramolecular rearrangement to form a Bronsted acid comprising W- and said removable positive hydrogen ion of R′.
Claim 4
Dependent Claim
35 words
A photoinitiator according to claim 2 in which W- is chosen from the group consisting of BF₄-, ClO₄-, AsF₆-, PF₆-, CH₃SO₃-, CF₃SO₃-, FeCl₄-, BiCl ², SnCl₆-, AlF ³, GaCl₄-, InF₄-, TiF₆-, ZrF₆-, SbF₆-, and p-toluenesulfonate.
Claim 5
Dependent Claim
45 words
A photoinitiator according to claim 1 or 2 chosen from among 9-anthrylmethyl-p-cyanobenzylsulfonium trifluoromethanesulfonate, 9-anthrylmethyl-p-cyanobenzyl sulfonium hexafluorophosphate, 9-(10-methoxyanthryl)methyl-p-cyanobenzyl sulfonium hexafluoroantimonate, 9-anthrylmethyl-2,3,4,5,6,-pentafluorobenzyl sulfonium trifluoromethanesulfonate, 9-(10-methylanthryl)methyl-p-cyanobenzyl sulfonium hexafluorophosphate, 5-naphthacenylmethyl-cyanomethyl sulfonium trifluoromethanesulfonate, 5-naphthacenylmethyl-fluoromethyl sulfonium hexafluoroantimonate, 9-(10-chloroanthryl)methyl-p-fluorobenzyl sulfonium p-toluenesulfonate, 9-anthrylmethyl-p-cyanobenzyl sulfonium tetrafluoroborate, 9-anthrylmethyl-2,4-dicyanobenzyl sulfonium hexafluorophosphate, and 9-(10-methoxyanthryl)ethyl-2,3,4,5,6 ,-pentafluorobenzyl sulfonium perchlorate.
Claim 6
Dependent Claim
25 words
A photocurable composition comprising a material curable by a Bronsted acid and a photoinitiator according to any one of claims 1, 2, 3 and 4.
Claim 7
Dependent Claim
25 words
A photocurable composition according to claim 5 wherein the material curable by a Bronsted acid is an epoxy resin polymerizable to a higher molecular weight.
Claim 8
Dependent Claim
31 words
A method of forming images which comprises exposing to visible radiation having a wavelength larger than 400 nm a material curable by a Bronsted acid according to claim 5 or 6.
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