US4873169A
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Process for the preparation of an o-naphthoquinonediazide sulfonic acid ester and photosensitive mixture containing same
Assignee: CLARIANT AZ (DEUTSCHLAND) AG
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Filing: 1987-08-20
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Granted: 1989-10-10
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Expires: 2007-08-20
Abstract
Abstract A process for the preparation of an o-naphthoquinonediazide sulfonic acid ester is disclosed. Esterification of an o-naphthoquinonediazide sulfonic acid halide with a mono- or polyvalent phenolic compound in a solvent is performed in the presence of ammonia, of ammonium salts of weak acids or of aliphatic derivatives of ammonia having 1 to 3 carbon atoms, at a pH within the range from about 1.5 to about 8.5 and a temperature within the range from about 15° C. to about 40° C. The esters of o-naphthoquinonediazide sulfonic acid which are obtained by this process contain only small amounts of metal ions and can be used in photosensitive mixtures satisfying high requirements of the microelectronics industry.
Inventors
- 👤 Fritz Erdmann
- 👤 Horst-Dieter Thamm
- 👤 Hans-Joachim Staudt
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 11:49
CPC Classifications
C; C07; C07C; C07C309/00; C07C309/63; C07C309/72; C07C303/00; C07C303/26; C07C303/28; G; G03; G03F; G03F7/00; G03F7/004; G03F7/022
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
117 words
A process for the preparation of an o-naphthoquinone diazide sulfonic acid ester comprising the steps of: mixing an o-naphthoquinone diazide sulfonic acid halide with a mono- or polyvalent phenolic compound in a solvent; adding a basic component selected from the group consisting of ammonia, ammonium salts of weak acids and monohydroxy aliphatic amine with 1 to 3 carbon atoms or dihydroxy aliphatic amine with 1 to 3 carbon atoms; controlling the pH within the range from about 1.5 to about 8.5 and the temperature within the range from about 15° C. to about 40° C. to carry out an esterification reaction producing an o-naphthoquinone diazide sulfonic acid ester; and precipitating the o-naphthoquinone diazide sulfonic acid ester produced.
Claim 2
Dependent Claim
117 words
A process for the preparation of an o-naphthoquinone diazide sulfonic acid ester comprising the steps of: mixing an o-naphthoquinone diazide sulfonic acid halide with a mono- or polyvalent phenolic compound in a solvent; adding a basic component selected from the group consisting of ammonia, ammonium salts of weak acids and monohydroxy aliphatic amine with 1 to 3 carbon atoms or dihydroxy aliphatic amine with 1 to 3 carbon atoms; controlling the pH within the range from about 1.5 to about 8.5 and the temperature within the range from about 15° C. to about 40° C. to carry out an esterification reaction producing an o-naphthoquinone diazide sulfonic acid ester; and precipitating the o-naphthoquinone diazide sulfonic acid ester produced.
Claim 3
Dependent Claim
24 words
An o-naphthoquinoe diazide sulfonic acid ester having less than about 1 p.p.m. of any metal ion, prepared by the process according to claim 1.
Claim 4
Dependent Claim
40 words
A photosensitive mixture comprising a photosensitive o-naphthoquinone diazide sulfonic acid ester prepared by the process according to claim 1 in admixture with from about 50 to 90% of a binder which is insoluble in water and soluble in aqueous-alkaline solutions.
Claim 5
Dependent Claim
18 words
A process as claimed in claim 1, wherein the esterification is performed in the presence of aqueous ammonia.
Claim 6
Dependent Claim
24 words
A process as claimed in claim 1, wherein the esterification is performed in the presence of ammonium salts of a carbonic or carboxylic acid.
Claim 7
Dependent Claim
19 words
A process as claimed in claim 1, wherein the esterification is performed in the presence of monoethanolamine or diethanolamine.
Claim 8
Dependent Claim
24 words
A process as claimed in claim 1, wherein the esterification is performed at a pH within the range from about 6 to about 8.
Claim 9
Dependent Claim
26 words
A process as claimed in claim 1, wherein the esterification is performed at a temperature within the range from about 20° C. to about 35° C.
Claim 10
Dependent Claim
14 words
A process as claimed in claim 5, wherein the carboxylic acid comprises acetic acid.
Claim 11
Dependent Claim
30 words
A process as claimed in claim 1, wherein the phenolic compound is a low molecular weight phenol having at least two benzene nuclei and at least two phenolic hydroxy groups.
Claim 12
Dependent Claim
161 words
A process as claimed in claim 1, wherein the phenolic compound is represented by the formula ##STR2## in which R denotes a single bond or one of the groups CO, S, O, SO 2 or CR 6 R 7 , preferably CO or CR 6 R 7 , R 1 , R 2 , R 3 denote hydrogen or halogen atoms, R 4 and R 5 denote hydroxy groups, or alkyl or alkoxy groups having 1 to 4 carbon atoms, and R 6 and R 7 denote hydrogen atoms or alkyl groups having 1 to 4 carbon atoms, preferably hydrogen atoms or methyl groups, or in which two of the radicals R 3 , R 4 and R 5 and the radicals R 1 und R 2 together each denote an aromatic ring, whereby in all cases at least one of the radicals R 1 , R 2 , R 3 , R 4 and R 5 denotes a hydroxy group.
Claim 13
Dependent Claim
17 words
A process as claimed in claim 1, wherein the o-naphthoquinone diazide sulfonic acid halide comprises a chloride.
Claim 14
Dependent Claim
21 words
A process as claimed in claim 1, wherein the phenolic compound comprises at least one polymeric compound having phenolic hydroxy groups.
Claim 15
Dependent Claim
22 words
A process as claimed in claim 13, wherein the polymeric compound comprises a condensation resin of a phenol and a carbonyl compound.
Claim 16
Dependent Claim
21 words
A process as claimed in claim 13, wherein the condensation resin is selected from the group consisting of cresol/formaldehyde and phenol/formaldehyde.
Claim 17
Dependent Claim
21 words
A process as claimed in claim 14, wherein the condensation resin is selected from the group consisting of pyrogallol/acetone and polyhydroxybenzophenone/formaldehyde.
Claim 18
Dependent Claim
18 words
A process as claimed in claim 1, wherein easily-separated, water-soluble alkaline hydrochlorides are produced during said esterification reaction.
Claim 19
Dependent Claim
13 words
A process as claimed in claim 1, consisting essentially of the recited steps.
References Cited (Backward Citations)
US3046120A
Cited
US3130048A
Cited
GB1113759A
Cited
US3647443A
Cited
GB1330932A
Cited
US4115128A
Cited
US4266001A
Cited
US4275139A
Cited
US4424270A
Cited
US4397937A
Cited
US4610953A
Cited
US4681923A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1992-10-09 | 1993-04-10 | 1993-10-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1996-10-09 | 1997-04-10 | 1997-10-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2000-10-09 | 2001-04-10 | 2001-10-10 | $7700.00 | Window Closed / Lapsed |