US5401607A
Expired / Lapsed
US
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Processes and compositions for photogeneration of acid
Assignee: Intellectual Ventures I LLC
•
Filing: 1993-06-29
•
Granted: 1995-03-28
•
Expires: 2013-06-29
Abstract
Abstract An infra-red sensitive acid-generating medium comprises a binder, an iodonium salt; and a squarylium dye capable of absorbing infra-red radiation having a wavelength within the range of about 700 to about 1200 nm, the dye having a squarylium ring the 1- and 3-positions of which are each connected, via a single sp2 carbon atom, to a pyrylium, thiopyrylium, benzpyrylium or benzthiopyrylium nucleus, at least one of the sp2 carbon atoms having a hydrogen atom attached thereto, and the 2-position of the squarylium ring bearing an O-, amino or substituted amino, or sulfonamido group.
Inventors
- 👤 Larry C. Takiff
- 👤 Stephen J. Telfer
- 👤 Kenneth C. Waterman
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 21:27
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/039; G03F7/26; G03F7/34; G03F7/346
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
92 words
An acid-generating medium comprising: a diaryl iodonium salt; and a squarylium dye capable of absorbing infra-red radiation having a wavelength within the range of 700 to 1200 nm, the dye having a squarylium ring the 1- and 3-positions of which are each connected, via a single sp 2 carbon atom, to a pyrylium, thiopyrylium, benzpyrylium or benzthiopyrylium moiety, at least one of the sp 2 carbon atoms having a hydrogen atom attached thereto, and the 2-position of the squarylium ring bearing an O - , amino or substituted amino, or sulfonamido group.
Claim 2
Dependent Claim
92 words
An acid-generating medium comprising: a diaryl iodonium salt; and a squarylium dye capable of absorbing infra-red radiation having a wavelength within the range of 700 to 1200 nm, the dye having a squarylium ring the 1- and 3-positions of which are each connected, via a single sp 2 carbon atom, to a pyrylium, thiopyrylium, benzpyrylium or benzthiopyrylium moiety, at least one of the sp 2 carbon atoms having a hydrogen atom attached thereto, and the 2-position of the squarylium ring bearing an O - , amino or substituted amino, or sulfonamido group.
Claim 3
Dependent Claim
37 words
A medium according to claim 1 wherein the 2-position of the squarylium ring bears an amino or substituted amino group, and at least one of the pyrylium, thiopyrylium, benzpyrylium or benzthiopyrylium moieties bears at least electron-donating substituent.
Claim 4
Dependent Claim
28 words
A medium according to claim 1 wherein the infra-red dye has an oxidation potential in dichloromethane not greater than about 500 mV relative to a standard calomel electrode.
Claim 5
Dependent Claim
17 words
A medium according to claim 1 wherein the diaryl iodonium salt is an alkoxyphenyl phenyl iodonium salt.
Claim 6
Dependent Claim
17 words
A medium according to claim 4 wherein the alkoxyphenyl phenyl iodonium salt is octyloxyphenyl phenyl iodonium hexafluoroantimonate.
Claim 7
Dependent Claim
21 words
A medium according to claim 1 further comprising a binder selected from the group consisting of polystyrene, poly(α-methylstyrene) and poly(vinyl chloride).
Claim 8
Dependent Claim
24 words
A medium according to claim 1 wherein, in the infra-red dye, one of said sp 2 carbon atoms does not bear a hydrogen atom.
Claim 9
Dependent Claim
20 words
A medium according to claim 1 wherein the two pyrylium, thiopyrylium, benzpyrylium or benzthiopyrylium moieties are different from one another.
Claim 10
Dependent Claim
46 words
A medium according to claim 1 wherein at least one of the pyrylium, thiopyrylium, benzpyrylium or benzthiopyrylium moieties is a 2-substituted or 2,6-disubstituted pyrylium or thiopyrylium group, or a 2-substituted benzpyrylium or benzthiopyrylium group, wherein the or each substituent comprises an alkyl, cycloalkyl or alkoxyphenyl group.
Claim 11
Dependent Claim
111 words
A medium according to claim 1 wherein at least one of the pyrylium, thiopyrylium, benzpyrylium or benzthiopyrylium moieties is a 7-substituted benzpyrylium or benzthiopyrylium group wherein the 7-substituent is a morpholino group or a disubstituted amino group, in which each of the substituents is an alkyl or cycloalkyl group, or the two substituents on the amino group together form a polymethylene chain which, together with the nitrogen atom of the amino group, forms a heterocyclic ring, or the two substituents on the amino group are two polymethylene chains, the ends of which remote from the nitrogen atom are connected to the 6- and 8-carbon atoms of the benzpyrylium or benzthiopyrylium group.
Claim 12
Dependent Claim
106 words
A medium according to claim 1 having a first layer containing the binder, infra-red dye and diaryl iodonium salt, the first layer also comprising a depolymerizable polymer which at least partially depolymerizes in the presence of acid, the medium further comprising a layer of a porous or particulate imaging material superposed on the first layer, the layer of the imaging material having a cohesive strength greater than the adhesive strength between the imaging material and the first layer prior to depolymerization of the polymer, but less than the adhesive strength between the imaging material and the first layer after at least partial depolymerization of the polymer.
Claim 13
Dependent Claim
15 words
A medium according to claim 1 wherein the infra-red dye is of the formula: ##STR16##
Claim 14
Dependent Claim
43 words
A medium according to claim 1 further comprising a secondary acid generator capable of being thermally decomposed to form a second acid, the thermal decomposition of the secondary acid generator being catalyzed by the superacid produced by decomposition of the diaryl iodonium salt.
Claim 15
Dependent Claim
135 words
A process for generating acid, which process comprises: providing a mixture of a diaryl iodonium salt and a squarylium dye capable of absorbing infra-red radiation having a wavelength within the range of 700 to 1200 nm, the dye having a squarylium ring the 1- and 3-positions of which are each connected, via a single sp 2 carbon atom, to a pyrylium, thiopyrylium, benzpyrylium or benzthiopyrylium moiety, at least one of the sp 2 carbon atoms having a hydrogen atom attached thereto, and the 2-position of the squarylium ring bearing an O - , amino or substituted amino, or sulfonamido group; and irradiating the mixture with infra-red radiation having a wavelength within the range of 700 to 1200 nm, thereby causing absorption of the radiation by the squarylium dye and formation of acid in the mixture.
Claim 16
Dependent Claim
135 words
A process for generating acid, which process comprises: providing a mixture of a diaryl iodonium salt and a squarylium dye capable of absorbing infra-red radiation having a wavelength within the range of 700 to 1200 nm, the dye having a squarylium ring the 1- and 3-positions of which are each connected, via a single sp 2 carbon atom, to a pyrylium, thiopyrylium, benzpyrylium or benzthiopyrylium moiety, at least one of the sp 2 carbon atoms having a hydrogen atom attached thereto, and the 2-position of the squarylium ring bearing an O - , amino or substituted amino, or sulfonamido group; and irradiating the mixture with infra-red radiation having a wavelength within the range of 700 to 1200 nm, thereby causing absorption of the radiation by the squarylium dye and formation of acid in the mixture.
Claim 17
Dependent Claim
28 words
A process according to claim 14 wherein the squarylium dye has an oxidation potential in dichloromethane not greater than about 500 mV relative to a standard calomel electrode.
Claim 18
Dependent Claim
17 words
A process according to claim 14 wherein the diaryl iodonium salt is an alkoxyphenyl phenyl iodonium salt.
Claim 19
Dependent Claim
22 words
A process according to claim 14 wherein the squarylium dye and the diaryl iodonium salt are dispersed in a solid polymeric binder.
Claim 20
Dependent Claim
15 words
A process according to claim 17 wherein the binder is polystyrene, poly(α-methylstyrene) or poly(vinyl chloride).
Claim 21
Dependent Claim
21 words
A process according to claim 14 wherein, in the squarylium dye, the two pyrylium, thiopyrylium, benzpyrylium or benzthiopyrylium moleties are different.
Claim 22
Dependent Claim
50 words
A process according to claim 14 wherein, in the squarylium dye, at least one of the pyrylium, thiopyrylium, benzpyrylium or benzthiopyrylium moleties is a 2-substituted or 2,6-disubstituted pyrylium or thiopyrylium group, or a 2-substituted benzpyrylium or benzthiopyrylium group, wherein the or each substituent comprises an alkyl, cycloalkyl or alkoxyphenyl group.
Claim 23
Dependent Claim
115 words
A process according to claim 14 wherein, in the squarylium dye, at least one of the pyrylium, thiopyrylium, benzpyrylium or benzthiopyrylium moleties is a 7-substituted benzpyrylium or benzthiopyrylium group wherein the 7-substituent is a morpholino group or a disubstituted amino group in which each of the substituents is an alkyl or cycloalkyl group, or the two substituents on the amino group together form a polymethylene chain which, together with the nitrogen atom of the amino group, forms a heterocyclic ring, or the two substituents on the amino group are two polymethylene chains, the ends of which remote from the nitrogen atom are connected to the 6- and 8-carbon atoms of the benzpyrylium or benzthiopyrylium group.
Claim 24
Dependent Claim
194 words
A process according to claim 14 wherein the mixture further comprises a depolymerizable polymer which at least partially depolymerizes in the presence of acid, the mixture forming the first layer of an imaging medium, this medium, this medium further comprising a layer of a porous or particulate imaging material superposed on the first layer, the layer of the imaging material having a cohesive strength greater than the adhesive strength between the imaging material and the first layer prior to depolymerization of the polymer, the process comprising imagewise exposing the imaging medium to infra-red radiation having a wavelength of 700 to 1200 nm, thereby causing absorption of the infra-red radiation by the squarylium dye, generation of acid by the diaryl iodonium salt and at least partial depolymerization of the polymer in the exposed areas of the first layer, rendering these exposed areas tacky and firmly attaching exposed portions of the imaging material layer to the first layer; and removing from the first layer the portions of the imaging material in the unexposed areas, but leaving the portions of the imaging material in the exposed areas adhered to the first layer, and thereby forming an image.
Claim 25
Dependent Claim
106 words
A process according to claim 14 wherein the medium further comprises a secondary acid generator capable of being thermally decomposed to form a secondary acid, the thermal decomposition of the secondary acid generator being catalyzed by the superacid produced by decomposition of the diaryl iodonium salt, and wherein, following the imagewise irradiation with infra-red radiation, the whole medium is irradiated with actinic radiation of a wavelength shorter than the wavelength of the infra-red radiation and capable of decomposing the diaryl iodonium salt, thereby causing decomposition of part of the remaining diaryl iodonium salt, with formation of free superacid in the areas exposed to the infra-red radiation.
Claim 26
Dependent Claim
15 words
A process according to claim 14 wherein the squarylium dye is of the formula: ##STR17##
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1998-03-27 | 1998-09-26 | 1999-03-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2002-03-27 | 2002-09-26 | 2003-03-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2006-03-27 | 2006-09-26 | 2007-03-28 | $7700.00 | Window Closed / Lapsed |