US4090877A
Expired / Lapsed
US
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Photosensitive imageable composition containing a hexaaromaticbimidazole, a leuco dye and an oxygen-sensitizing compound
Assignee: 3M Co
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Filing: 1977-08-15
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Granted: 1978-05-23
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Expires: 1997-08-15
Abstract
Abstract An imageable composition comprising (a) a leuco form of dye, (b) a hexaaromaticbiimidazole that effects the conversion of said dye to a differently colored compound when exposed to electromagnetic radiation at a wavelength of from about 250 to 400 nanometers, and (c) an oxygen sensitizing compound in an amount such that, upon exposure to electromagnetic radiation at a wavelength of from about 400 to 700 nanometers in the presence of oxygen, said dye is stabilized in its leuco form.
Inventors
- 👤 Richard D. Streeper
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 02:15
CPC Classifications
G; G03; G03C; G03C1/00; G03C1/72; G03C1/73; G03C1/732
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
346 words
In an imageable composition of the type including (a) a dye in the leuco form, and (b) a hexaaromaticbiimidazole that, upon exposure to electromagnetic radiation at a wavelength of from about 250 to 400 nanometers, effects a conversion of said dye to a differently colored compound; the improvement comprising: including in said composition an oxygen-sensitizing compound which, when exposed to radiation of from 400 to 700 nanometers in the presence of oxygen, brings about the formation of singlet oxygen and exhibits a linear photolysis characteristic wherein said sensitizing compound causes 1,3-diphenylisobenzofuran to disappear linearly and smoothly with a zero order rate plot when a solution comprising 0.125 grams of said oxygen sensitizing compound, 0.01 mole of 1,3-diphenylisobenzofuran and 1 liter of acetone is irradiated with light from two 150 watt flood lamps focused on said solution; wherein said oxygen sensitizing compound is selected from the group consisting of porphyrins, and polycyclic aromatic compounds comprising from 2 to 3 moieties in conjugate relationship as a part of a single chromophore, each of said moieties comprising three linearly kata condensed, 6-membered carbocycles, an --OZ group being attached to the meso position on each of said moieties, wherein Z is a stable monovalent radical, the --OZ group being a stabilizing group for said polycyclic aromatic compound, wherein at least one auxochromic group comprising an atom having an atomic weight of at least 31 is bonded to said chromophore by means of the atom and wherein said moieties are joined together by means selected from bonding said moieties in the peri fashion and bonding said moieties through a linking moiety selected from the group consisting of (a) atoms which are at least trivalent and are capable of forming covalent bonds, (b) ligands having two or more atoms which are at least bidentate, and (c) covalent single and double bonds; wherein said oxygen sensitizer is present in an amount such that, upon exposure of said composition to electromagnetic radiation at a wavelength of about 400 to 700 nanometers in the presence of oxygen, said dye is stabilized in the leuco form.
Claim 2
Dependent Claim
346 words
In an imageable composition of the type including (a) a dye in the leuco form, and (b) a hexaaromaticbiimidazole that, upon exposure to electromagnetic radiation at a wavelength of from about 250 to 400 nanometers, effects a conversion of said dye to a differently colored compound; the improvement comprising: including in said composition an oxygen-sensitizing compound which, when exposed to radiation of from 400 to 700 nanometers in the presence of oxygen, brings about the formation of singlet oxygen and exhibits a linear photolysis characteristic wherein said sensitizing compound causes 1,3-diphenylisobenzofuran to disappear linearly and smoothly with a zero order rate plot when a solution comprising 0.125 grams of said oxygen sensitizing compound, 0.01 mole of 1,3-diphenylisobenzofuran and 1 liter of acetone is irradiated with light from two 150 watt flood lamps focused on said solution; wherein said oxygen sensitizing compound is selected from the group consisting of porphyrins, and polycyclic aromatic compounds comprising from 2 to 3 moieties in conjugate relationship as a part of a single chromophore, each of said moieties comprising three linearly kata condensed, 6-membered carbocycles, an --OZ group being attached to the meso position on each of said moieties, wherein Z is a stable monovalent radical, the --OZ group being a stabilizing group for said polycyclic aromatic compound, wherein at least one auxochromic group comprising an atom having an atomic weight of at least 31 is bonded to said chromophore by means of the atom and wherein said moieties are joined together by means selected from bonding said moieties in the peri fashion and bonding said moieties through a linking moiety selected from the group consisting of (a) atoms which are at least trivalent and are capable of forming covalent bonds, (b) ligands having two or more atoms which are at least bidentate, and (c) covalent single and double bonds; wherein said oxygen sensitizer is present in an amount such that, upon exposure of said composition to electromagnetic radiation at a wavelength of about 400 to 700 nanometers in the presence of oxygen, said dye is stabilized in the leuco form.
Claim 3
Dependent Claim
50 words
An imageable composition according to claim 1 wherein said leuco form of dye is selected from the group consisting of sulfoaminotriarylmethane salts; aminotriarylmethanes; aminoxanthenes; aminothioxanthanes; amino-9,10-dihydroacridines; aminophenoxazines; aminophenothiazines; aminodihydrophenazines; aminodiphenylmethanes; leuco indamines; aminohydrocinnamic acids; hydrazines; leuco indigoid dyes; amino-2,3-dihydroanthraquinones; tetrahalo-4,4'-bisphenols; phenethylanilines; 10-acylaminophenothiazines; 10-acylaminophenoxazines; 10-acylaminodihydrophenazines; oxoarylideneimidazoles; and N-hydrocarbyl substituted dihydroheterocyclic amines.
Claim 4
Dependent Claim
17 words
An imageable composition according to claim 2 wherein said dye in the leuco form comprises an aminotriarylmethane.
Claim 5
Dependent Claim
12 words
An imageable composition according to claim 3 wherein said aminotriarylmethane is tris(4-diethylamino-2-tolyl)methane.
Claim 6
Dependent Claim
19 words
An imageable composition according to claim 2 wherein said dye in the leuco form comprises a sulfo aminotriarylmethane salt.
Claim 7
Dependent Claim
24 words
An imageable composition according to claim 5 wherein the sulfo salt group is oriented ortho to the methane carbon atom of the sulfoaminotriarylmethane salt.
Claim 8
Dependent Claim
16 words
An imageable composition according to claim 6 wherein said leuco dye is 1-(2-sulfophenyl)-bis(4-diethylamino-2-tolyl) methane sodium salt.
Claim 9
Dependent Claim
12 words
An imageable composition according to claim 1 wherein said hexaaromaticbiimidazole is asymmetric.
Claim 10
Dependent Claim
12 words
An imageable composition according to claim 8 wherein said hexaaromaticbiimidazole is 2-phenyl-2'-(2-tolyl)-4,4'-5,5'-tetraphenylbiimidazole.
Claim 11
Dependent Claim
12 words
An imageable composition according to claim 1 wherein said hexaaromaticbiimidazole is symmetric.
Claim 12
Dependent Claim
12 words
An imageable composition according to claim 10 wherein said hexaaromaticbiimidazole is 2,2'-bis(2-tolyl)-4,4',5,5'-tetraphenylbiimidazole.
Claim 13
Dependent Claim
17 words
An imageable composition according to claim 1 wherein said oxygen sensitizing compound is said polycyclic aromatic compound.
Claim 14
Dependent Claim
15 words
An imageable composition according to claim 12 wherein said oxygen sensitizing compound is ethylated trichloroviolanthrone.
Claim 15
Dependent Claim
55 words
An imageable composition according to claim 1 wherein said oxygen sensitizing compound is a porphyrin of the formula ##STR6## wherein X is selected from carbon and nitrogen wherein the carbon may have attached thereto hydrogen, alkyl containing from about 1 to 14 carbon atoms, aryl groups, and heterocyclic groups containing carbon, oxygen, nitrogen and sulfur.
Claim 16
Dependent Claim
17 words
An imageable composition according to claim 14 wherein said oxygen sensitizer is selected from tetraarylporphyrin and octaaryltetraazaporphyrin.
Claim 17
Dependent Claim
12 words
An imageable composition according to claim 15 wherein said sensitizer is tetraarylporphyrin.
Claim 18
Dependent Claim
13 words
An imageable composition according to claim 16 wherein said tetraarylporphyrin is α,β,γ,δ tetraphenylporphyrin.
Claim 19
Dependent Claim
12 words
An imageable composition according to claim 15 wherein said sensitizer is octaaryltetraazaporphyrin.
Claim 20
Dependent Claim
12 words
An imageable composition according to claim 18 wherein said octaaryltetraazaphorphyrin is octaphenyltetraazaporphyrin.
Claim 21
Dependent Claim
67 words
An imageable composition according to claim 1 wherein said oxygen sensitizing compound is a prophyrin of the formula ##STR7## wherein X is selected from carbon and nitrogen wherein the carbon may have attached thereto hydrogen, alkyl containing from about 1 to 14 carbon atoms, aryl groups, and heterocyclic groups containing carbon, oxygen, nitrogen and sulfur and M is a metal which forms chelates with the pyrole nitrogens.
Claim 22
Dependent Claim
23 words
An imageable composition according to claim 1 wherein there is further included a film forming binder that is transmissive to said electromagnetic radiations.
Claim 23
Dependent Claim
14 words
An imageable composition according to claim 21 wherein there is further included a plasticizer.
Claim 24
Dependent Claim
17 words
A dimensionally stable sheet having applied to a surface thereof an imageable composition according to claim 1.
Claim 25
Dependent Claim
10 words
A film of an imageable composition according to claim 1.
Claim 26
Dependent Claim
104 words
A method of forming images comprising the steps of (a) providing a substrate having coated on at least one surface thereof an imageable composition according to claim 1; and (b) irradiating said imageable composition, in any order, to (i) electromagnetic radiation having wavelengths of from about 250 to 400 nanometers so as to effect the formation of color in the areas so irradiated and (ii) electromagnetic radiation having wavelengths of from about 400 to 700 nanometers so as to stabilize said leuco dye in the leuco form in the areas so irradiated, provided that the first of said irradiations is in an imagewise fashion.
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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) | 1981-05-22 | 1981-11-21 | 1982-05-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-05-22 | 1985-11-21 | 1986-05-23 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-05-22 | 1989-11-21 | 1990-05-23 | $7700.00 | Window Closed / Lapsed |