US4312934A
Expired / Lapsed
US
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Photosensitive compositions
Assignee: Bard Laboratories Inc
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Filing: 1980-05-29
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Granted: 1982-01-26
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Expires: 2000-05-29
Abstract
Abstract Photosensitive compositions containing nitrate ester chain polymers, such as nitrocellulose, molecularly intimately admixed with at least one compound having a free basic amine group, preferably a primary amine group, directly attached to an aromatic ring carbon. On suitable exposure to ultraviolet light, such compositions will print out a useful image directly, or, should a much lesser light exposure be preferred, they can be developed and fixed to an image intensified to useful strength by either heat alone, for amines that are sufficiently volatile at ingredient reaction temperatures, or by solvent selective removal of ingredients from unexposed areas, and subsequently intensified either by heat or overall ultraviolet exposure. Exposed areas of such compositions are more resistant both to volatilization of the amines and to solvent removal than the non-exposed areas. High optical density is attainable using very thin coatings, permitting high resolution grainless images. If developed by solvent selective removal of all ingredients from unexposed areas, the composition is useful as a photoresist material.
Inventors
- 👤 John F. Rice
- 👤 Albert P. Yundt
- 👤 Kenneth J. Quast
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 12:41
CPC Classifications
G; G03; G03C; G03C1/00; G03C1/72; G03C1/73; G03C1/733; G03F; G03F7/00; G03F7/004; G03F7/038
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
130 words
A method for forming an image, said method comprising imagewise exposing a photosensitive composition to electromagnetic radiation in the range of ultraviolet to visible light, wherein said photosensitive composition comprises a molecularly intimate admixture of at least one basic, aromatic amine and a polymer polynitrate ester, the aromatic amine comprising a compound of the following formula: ##STR6## wherein R is an aromatic nucleus substituted either directly or by nitrogen or oxygen bonds with members of the group of hydrogen, halogen, alkyl, aryl and alkaryl groups, and X and Y are selected from the group of hydrogen, hydroxyl, alkyl, aryl and alkaryl groups, provided that X and Y are not both hydroxyl, such that said aromatic amine is relatively basic, such basicity not being substantially nullified by salt or amide formation.
Claim 2
Independent Claim
130 words
A method for forming an image, said method comprising imagewise exposing a photosensitive composition to electromagnetic radiation in the range of ultraviolet to visible light, wherein said photosensitive composition comprises a molecularly intimate admixture of at least one basic, aromatic amine and a polymer polynitrate ester, the aromatic amine comprising a compound of the following formula: ##STR6## wherein R is an aromatic nucleus substituted either directly or by nitrogen or oxygen bonds with members of the group of hydrogen, halogen, alkyl, aryl and alkaryl groups, and X and Y are selected from the group of hydrogen, hydroxyl, alkyl, aryl and alkaryl groups, provided that X and Y are not both hydroxyl, such that said aromatic amine is relatively basic, such basicity not being substantially nullified by salt or amide formation.
Claim 3
Dependent Claim
19 words
The method of claim 1, wherein the aromatic nucleus is selected from the group of benzene, naphthalene and anthracene.
Claim 4
Dependent Claim
22 words
The method of claim 1, wherein the polymer is a member of the group of nitrocellulose, nitrostarch or poly(vinylnitrate) and mixtures thereof.
Claim 5
Dependent Claim
23 words
The method of claim 1, wherein the polymer has at least one amine-accessible nitrate ester group per eight atoms in the polymer chain.
Claim 6
Dependent Claim
11 words
The method of claim 1, wherein the amine comprises 1,8-diamino naphthalene.
Claim 7
Dependent Claim
10 words
The method of claim 5, wherein the polymer comprises nitrocellulose.
Claim 8
Dependent Claim
28 words
The method of claim 6, wherein the nitrocellulose comprises from about 10 to 13.5% nitrogen content and has a viscosity of from about 0.1 to about 5,000 seconds.
Claim 9
Dependent Claim
26 words
The method of claim 7, wherein the nitrocellulose comprises from about 11.7 to 12% nitrogen and has a viscosity of from about 0.25 to 10 seconds.
Claim 10
Dependent Claim
41 words
The method of claim 1, wherein the aromatic amine is selected from the group of 1-naphthylamine, 2-naphthylamine, 4-chloro-1,3-phenylenediamine, 3-amino-9 -ethylcarbazole,o-toluidine, m-phenylenediamine, p-anilinophenol, 2,5-dimethoxy aniline, 3,3'-dimethyoxybenzidene, 1,5-diaminonaphthalene, 1,8-diaminonaphthalene, diphenylamine, triphenylamine, 6-dimethylaminoquinaldine, tris 4-(N,N-dimethylanilino) methane, 4-methoxyphenylhydroxylamine, diphenylhydroxylamine, indole, carbazole, N-vinyl carbazole, and p-dimethylaminobenzaldehyde.
Claim 11
Dependent Claim
12 words
The method of claim 1, wherein the amine is a primary amine.
Claim 12
Dependent Claim
21 words
The method of claim 1, further comprising the step of developing the image produced by said exposing step to useful intensity.
Claim 13
Independent Claim
134 words
A method for forming an image, said method comprising: forming a photosensitive layer consisting essentially of a molecularly intimate admixture of at least one polymer polynitrate ester with at least one basic aromatic amine; and selectively exposing said photosensitive layer to light whereupon said layer becomes selectively solvent removable, wherein said aromatic amine comprises a compound of the following formula: ##STR7## wherein R is an aromatic nucleus substituted either directly or by nitrogen or oxygen bonds with members of the group of hydrogen, halogen, alkyl, aryl, and aralkyl groups, and X and Y are selected from the group of hydrogen, hydroxyl, alkyl, aryl and alkaryl groups provided that X and Y are not both hydroxyl, such that said aromatic amine is relatively basic, such basicity not being substantially nullified by salt or amide formation.
Claim 14
Independent Claim
134 words
A method for forming an image, said method comprising: forming a photosensitive layer consisting essentially of a molecularly intimate admixture of at least one polymer polynitrate ester with at least one basic aromatic amine; and selectively exposing said photosensitive layer to light whereupon said layer becomes selectively solvent removable, wherein said aromatic amine comprises a compound of the following formula: ##STR7## wherein R is an aromatic nucleus substituted either directly or by nitrogen or oxygen bonds with members of the group of hydrogen, halogen, alkyl, aryl, and aralkyl groups, and X and Y are selected from the group of hydrogen, hydroxyl, alkyl, aryl and alkaryl groups provided that X and Y are not both hydroxyl, such that said aromatic amine is relatively basic, such basicity not being substantially nullified by salt or amide formation.
Claim 15
Dependent Claim
19 words
The method of claim 12, wherein the aromatic nucleus is selected from the group of benzene, naphthalene and anthracene.
Claim 16
Dependent Claim
25 words
The method of claim 12, wherein the polymer nitrate ester is a member of the group of nitrocellulose nitrostarch and poly(vinyl nitrate) and mixtures thereof.
Claim 17
Dependent Claim
12 words
The method of claim 12, wherein the polymer polynitrate ester comprises nitrocellulose.
Claim 18
Dependent Claim
11 words
The method of claim 15, wherein the amine comprises 1,8-diamino naphthalene.
Claim 19
Dependent Claim
35 words
The method of claim 12, wherein upon exposure to light the polymer polynitrate ester and amine react to form a composition which is not solvent removable by solvents which swell or dissolve the non-exposed system.
Claim 20
Dependent Claim
21 words
The method of claim 12, wherein the exposed part of the layer is insoluble in solvents for the polymer polynitrate ester.
Claim 21
Dependent Claim
24 words
The method of claim 18, wherein the exposed part of the layer is insoluble in solvents selected from the group of esters and ketones.
Claim 22
Dependent Claim
34 words
The method of claim 12 wherein upon selective exposure to light the compositions becomes only selectively solvent removable by a solvent comprising a member of the group of methyl ethyl ketone and diisobutyl ketone.
Claim 23
Dependent Claim
146 words
A photoresist imaging process comprising: selectively exposing to light a substrate having thereon a layer of a photosensitive composition comprising a molecularly intimate admixture of at least one basic, aromatic amine and a polymer polynitrate ester, the aromatic amine comprising a compound of the following formula: ##STR8## wherein R is an aromatic nucleus substituted either directly or by nitrogen or oxygen bonds with members of the group of hydrogen, halogen, alkyl, aryl and alkaryl groups, and X and Y are selected from the group of hydrogen, hydroxyl, alkyl, aryl and alkaryl groups, provided that X and Y are not both hydroxyl, such that said aromatic amine is relatively basic, such basicity not being substantially nullified by salt or amide formation; dissolving the unexposed portion of said layer with a suitable solvent; and treating the substrate in the areas where the unexposed composition had been selectively removed.
Claim 24
Dependent Claim
146 words
A photoresist imaging process comprising: selectively exposing to light a substrate having thereon a layer of a photosensitive composition comprising a molecularly intimate admixture of at least one basic, aromatic amine and a polymer polynitrate ester, the aromatic amine comprising a compound of the following formula: ##STR8## wherein R is an aromatic nucleus substituted either directly or by nitrogen or oxygen bonds with members of the group of hydrogen, halogen, alkyl, aryl and alkaryl groups, and X and Y are selected from the group of hydrogen, hydroxyl, alkyl, aryl and alkaryl groups, provided that X and Y are not both hydroxyl, such that said aromatic amine is relatively basic, such basicity not being substantially nullified by salt or amide formation; dissolving the unexposed portion of said layer with a suitable solvent; and treating the substrate in the areas where the unexposed composition had been selectively removed.
Claim 25
Dependent Claim
16 words
The process of claim 21 further comprising the step of removing the portion of exposed composition.
Claim 26
Dependent Claim
34 words
The method of claim 11 wherein said developing step comprises (1) heating or (2) solvent selective removal of ingredients from unexposed portion of said layer and, subsequently, heating or exposing to overall ultraviolet radiation.
References Cited (Backward Citations)
US3042515A
Cited
US3884697A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-01-25 | 1985-07-27 | 1986-01-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-01-25 | 1989-07-27 | 1990-01-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-01-25 | 1993-07-27 | 1994-01-26 | $7700.00 | Window Closed / Lapsed |