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US4294911A Expired / Lapsed US ⏱️ 0.0 years remaining

Development of light-sensitive quinone diazide compositions using sulfite stabilizer

Assignee: Kodak Graphics Holding Inc
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Filing: 1979-06-18
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Granted: 1981-10-13
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Expires: 1999-06-18
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Abstract

Abstract Light-sensitive compositions containing a quinone diazide which are useful in positive-working photoresists and positive-working lithographic printing plates are developed with a developing composition comprising a quaternary alkanol ammonium hydroxide developing agent and a stabilizing concentration of a sulfite.

Inventors

  • 👤 John R. Guild

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-26 10:45
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/26; G03F7/30; G03F7/32; G03F7/322

Claims Analysis

Total Claims: 26
Claim 1
Independent Claim 62 words
A method of developing an image-wise-exposed layer of a light-sensitive quinone diazide composition comprising contacting said layer with an alkaline developing composition to remove exposed areas of said layer, said developing composition comprising an aqueous solution containing a quaternary alkanol ammonium hydroxide developing agent, in a sufficient concentration to remove exposed areas of said layer, and a stabilizing concentration of a sulfite.
Claim 2
Independent Claim 62 words
A method of developing an image-wise-exposed layer of a light-sensitive quinone diazide composition comprising contacting said layer with an alkaline developing composition to remove exposed areas of said layer, said developing composition comprising an aqueous solution containing a quaternary alkanol ammonium hydroxide developing agent, in a sufficient concentration to remove exposed areas of said layer, and a stabilizing concentration of a sulfite.
Claim 3
Dependent Claim 50 words
The method as claimed in claim 1 wherein said quaternary alkanol ammonium hydroxide developing agent has the formula: ##STR13## wherein R 1 is a hydroxyalkyl radical and each of R 2 , R 3 and R 4 is independently selected from the group consisting of hydrocarbyl radicals and hydroxyalkyl radicals.
Claim 4
Dependent Claim 89 words
The method as claimed in claim 1 wherein said quaternary alkanol ammonium hydroxide developing agent has the formula: ##STR14## wherein R 1 is a hydroxyalkyl radical of 2 to 8 carbon atoms, R 2 is a hydrocarbyl radical of 1 to 10 carbon atoms, R 3 is a hydroxyalkyl radical of 2 to 8 carbon atoms or a hydrocarbyl radical of 1 to 10 carbon atoms, and R 4 is a hydroxyalkyl radical of 2 to 8 carbon atoms or a hydrocarbyl radical of 1 to 10 carbon atoms.
Claim 5
Dependent Claim 37 words
The method as claimed in claim 1 wherein said quaternary alkanol ammonium hydroxide developing agent is selected from the group consisting of: tetraalkanolammonium hydroxides, monoalkyltrialkanolammonium hydroxides, dialkyldialkanolammonium hydroxides, trialkylmonoalkanolammonium hydroxides, monoalkylmonoaryldialkanolammonium hydroxides, dialkylmonoarylmonoalkanolammonium hydroxides, and monoarytrialkanolammonium hydroxides.
Claim 6
Dependent Claim 42 words
The method as claimed in claim 1 wherein said sulfite is selected from the group consisting of sodium sulfite, potassium sulfite, lithium sulfite, ammonium sulfite, sodium bisulfite, potassium bisulfite, lithium bisulfite, ammonium bisulfite, sodium metabisulfite, potassium metabisulfite, lithium metabisulfite, and ammonium metabisulfite.
Claim 7
Dependent Claim 23 words
The method as claimed in claim 1 wherein said developing composition consists essentially of an aqueous solution of methyltriethanolammonium hydroxide and ammonium sulfite.
Claim 8
Dependent Claim 69 words
In a process for forming a resist image which comprises developing an imagewise-exposed layer of a light-sensitive quinone diazide composition with an alkaline developing composition to remove exposed areas of said layer, the improvement wherein said alkaline developing composition comprises an aqueous solution containing a quaternary alkanol ammonium hydroxide developing agent, in a sufficient concentration to remove exposed areas of said layer, and a stabilizing concentration of a sulfite.
Claim 9
Dependent Claim 69 words
In a process for forming a resist image which comprises developing an imagewise-exposed layer of a light-sensitive quinone diazide composition with an alkaline developing composition to remove exposed areas of said layer, the improvement wherein said alkaline developing composition comprises an aqueous solution containing a quaternary alkanol ammonium hydroxide developing agent, in a sufficient concentration to remove exposed areas of said layer, and a stabilizing concentration of a sulfite.
Claim 10
Dependent Claim 50 words
The process as claimed in claim 7 wherein said quaternary alkanol ammonium hydroxide developing agent has the formula: ##STR15## wherein R 1 is a hydroxyalkyl radical and each of R 2 , R 3 and R 4 is independently selected from the group consisting of hydrocarbyl radicals and hydroxyalkyl radicals.
Claim 11
Dependent Claim 89 words
The process as claimed in claim 7 wherein said quaternary alkanol ammonium hydroxide developing agent has the formula: ##STR16## wherein R 1 is a hydroxyalkyl radical of 2 to 8 carbon atoms, R 2 is a hydrocarbyl radical of 1 to 10 carbon atoms, R 3 is a hydroxyalkyl radical of 2 to 8 carbon atoms or a hydrocarbyl radical of 1 to 10 carbon atoms, and R 4 is a hydroxyalkyl radical of 2 to 8 carbon atoms or a hydrocarbyl radical of 1 to 10 carbon atoms.
Claim 12
Dependent Claim 37 words
The process as claimed in claim 7 wherein said quaternary alkanol ammonium hydroxide developing agent is selected from the group consisting of: tetraalkanolammonium hydroxides, monoalkyltrialkanolammonium hydroxides, dialkyldialkanolammonium hydroxides, trialkylmonoalkanolammonium hydroxides, monoalkylmonoaryldialkanolammonium hydroxides, dialkylmonoarylmonoalkanolammonium hydroxides, and monoaryltrialkanolammonium hydroxides.
Claim 13
Dependent Claim 89 words
The process as claimed in claim 7 wherein said quaternary alkanol ammonium hydroxide developing agent has the formula: ##STR17## wherein R 1 is a hydroxyalkyl radical of 2 to 4 carbon atoms, R 2 is an alkyl radical of 1 to 4 carbon atoms, R 3 is a hydroxyalkyl radical of 2 to 4 carbon atoms or an alkyl radical of 1 to 4 carbon atoms, and R 4 is a hydroxyalkyl radical of 2 to 4 carbon atoms or an alkyl radical of 1 to 4 carbon atoms.
Claim 14
Dependent Claim 134 words
The process as claimed in claim 7 wherein said developing composition is an aqueous composition that is substantially free of metal ions and comprises: (1) from about 3 to about 25 percent by weight of a quaternary alkanol ammonium hydroxide developing agent of the formula: ##STR18## wherein R 1 is a hydroxyalkyl radical of 2 to 4 carbon atoms, R 2 is an alkyl radical of 1 to 4 carbon atoms, R 3 is a hydroxyalkyl radical of 2 to 4 carbon atoms or an alkyl radical of 1 to 4 carbon atoms, and R 4 is a hydroxyalkyl radical of 2 to 4 carbon atoms or an alkyl radical of 1 to 4 carbon atoms, and (2) from about 0.02 to about 0.2 moles of a sulfite per mole of said developing agent.
Claim 15
Dependent Claim 42 words
The process as claimed in claim 1 wherein said sulfite is selected from the group consisting of sodium sulfite, potassium sulfite, lithium sulfite, ammonium sulfite, sodium bisulfite, potassium bisulfite, lithium bisulfite, ammonium bisulfite, sodium metabisulfite, potassium metabisulfite, lithium metabisulfite, and ammonium metabisulfite.
Claim 16
Dependent Claim 23 words
The process as claimed in claim 1 wherein said developing composition consists essentially of an aqueous solution of methyltriethanolammonium hydroxide and ammonium sulfite.
Claim 17
Dependent Claim 25 words
The process as claimed in claim 1 wherein said quinone diazide composition is comprised of a monomeric quinone diazide incorporated in an alkali-soluble resinous binder.
Claim 18
Dependent Claim 28 words
The process as claimed in claim 1 wherein said quinone diazide composition is comprised of a monomeric quinone diazide that has been reacted with an alkali-soluble resinous material.
Claim 19
Dependent Claim 29 words
The process as claimed in claim 1 wherein said quinone diazide composition comprises a polymeric compound formed from the condensation reaction of a quinone diazide with a phenol-formaldehyde resin.
Claim 20
Dependent Claim 29 words
The process as claimed in claim 1 wherein said quinone diazide composition comprises a polymeric compound formed from the condensation reaction of a naphthoquinone diazide with a phenol-formaldehyde resin.
Claim 21
Dependent Claim 25 words
The process as claimed in claim 1 wherein said quinone diazide has a linkage selected from the group consisting of sulfonyl, carbonyl, carbonyloxy and sulfinyloxy.
Claim 22
Dependent Claim 28 words
The process as claimed in claim 1 wherein said quinone diazide composition comprises a polymeric compound formed from the condensation reaction of 1,2-naphthoquinone-2-diazide-5-sulfonyl chloride with a phenol-formaldehyde resin.
Claim 23
Dependent Claim 35 words
The process as claimed in claim 1 wherein said quinone diazide composition comprises a non-light-sensitive film-forming polymeric binder and a polymeric compound formed from the condensation reaction of a quinone diazide with a phenol-formaldehyde resin.
Claim 24
Dependent Claim 22 words
The process as claimed in claim 1 wherein said layer of light-sensitive quinone diazide composition is a coating on a silicon wafer.
Claim 25
Dependent Claim 85 words
In a process for forming a resist image which comprises developing an imagewise-exposed layer of a light-sensitive quinone diazide composition with an alkaline developing composition to remove exposed areas of said layer, the improvement wherein said alkaline developing composition is an aqueous solution which is substantially free of metal ions, and contains a sufficient concentration of methyltriethanolammonium hydroxide to remove the exposed areas of said layer of light-sensitive quinone diazide composition without substantial removal of the unexposed areas, and a stabilizing concentration of a sulfite.
Claim 26
Dependent Claim 85 words
In a process for forming a resist image which comprises developing an imagewise-exposed layer of a light-sensitive quinone diazide composition with an alkaline developing composition to remove exposed areas of said layer, the improvement wherein said alkaline developing composition is an aqueous solution which is substantially free of metal ions, and contains a sufficient concentration of methyltriethanolammonium hydroxide to remove the exposed areas of said layer of light-sensitive quinone diazide composition without substantial removal of the unexposed areas, and a stabilizing concentration of a sulfite.

References Cited (Backward Citations)

US2606118A Cited
US3549370A Cited
GB1328967A Cited
US3669660A Cited
US3713826A Cited
GB1367830A Cited
JPS5156226A Cited
US4239661A Cited
US4141733A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1984-10-12 1985-04-13 1985-10-13 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1988-10-12 1989-04-13 1989-10-13 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1992-10-12 1993-04-13 1993-10-13 $7700.00 Window Closed / Lapsed

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