US4933377A
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Novel sulfonium salts and the use thereof as photoinitiators
Assignee: Eastman Kodak Co
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Filing: 1988-02-29
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Granted: 1990-06-12
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Expires: 2008-02-29
Abstract
Abstract Sulfonium and oxysulfonium salts, useful as photoinitiators, 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 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.
Inventors
- 👤 Franklin D. Saeva
- 👤 David T. Breslin
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 13:28
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: 10
Claim 1
Independent Claim
129 words
A composition of matter comprising a material curable by a Bronsted acid, and a sulfonium or oxysulfonium salt having 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 atom; 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.
Claim 2
Dependent Claim
129 words
A composition of matter comprising a material curable by a Bronsted acid, and a sulfonium or oxysulfonium salt having 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 atom; 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.
Claim 3
Dependent Claim
143 words
A composition of matter comprising a material curable by a Bronsted acid, and a compound having the formula: ##STR2## 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
143 words
A composition of matter comprising a material curable by a Bronsted acid, and a compound having the formula: ##STR2## 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 5
Dependent Claim
130 words
A photocurable composition comprising an epoxy resin polymerizable to a higher molecular weight, and a sulfonium or oxysulfonium salt having 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 atom; 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.
Claim 6
Dependent Claim
130 words
A photocurable composition comprising an epoxy resin polymerizable to a higher molecular weight, and a sulfonium or oxysulfonium salt having 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 atom; 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.
Claim 7
Dependent Claim
144 words
A photocurable composition comprising an epoxy resin polymerisable to a higher molecular weight, and a compound having the formula: ##STR3## wherein: R' represent 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 8
Dependent Claim
144 words
A photocurable composition comprising an epoxy resin polymerisable to a higher molecular weight, and a compound having the formula: ##STR3## wherein: R' represent 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 9
Dependent Claim
17 words
A composition of matter comprising a material curable by a bronsted acid and, as photoinitiator, (9-Anthryl)methyl-p-cyanobenzylsulfonium trifluromethanesulfonate.
Claim 10
Dependent Claim
17 words
A composition of matter comprising a material curable by a bronsted acid and, as photoinitiator, (9-Anthryl)methyl-p-cyanobenzylsulfonium trifluromethanesulfonate.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1993-06-11 | 1993-12-11 | 1994-06-12 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-06-11 | 1997-12-11 | 1998-06-12 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-06-11 | 2001-12-11 | 2002-06-12 | $7700.00 | Window Closed / Lapsed |