JPH0319535B2 - - Google Patents
Info
- Publication number
- JPH0319535B2 JPH0319535B2 JP8571981A JP8571981A JPH0319535B2 JP H0319535 B2 JPH0319535 B2 JP H0319535B2 JP 8571981 A JP8571981 A JP 8571981A JP 8571981 A JP8571981 A JP 8571981A JP H0319535 B2 JPH0319535 B2 JP H0319535B2
- Authority
- JP
- Japan
- Prior art keywords
- general formula
- photosensitive composition
- salt
- dimethyl
- dimethylaniline
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 56
- 150000003839 salts Chemical class 0.000 claims description 46
- -1 aromatic diazonium salt Chemical class 0.000 claims description 29
- 239000011592 zinc chloride Substances 0.000 claims description 28
- 235000005074 zinc chloride Nutrition 0.000 claims description 28
- 239000012954 diazonium Substances 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 22
- 239000000843 powder Substances 0.000 claims description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
- 239000010410 layer Substances 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 229920000620 organic polymer Polymers 0.000 claims description 7
- 235000010443 alginic acid Nutrition 0.000 claims description 6
- 229920000615 alginic acid Polymers 0.000 claims description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- 239000002245 particle Substances 0.000 claims description 6
- 239000000783 alginic acid Substances 0.000 claims description 5
- 229960001126 alginic acid Drugs 0.000 claims description 5
- 239000000758 substrate Substances 0.000 claims description 5
- 150000004781 alginic acids Chemical class 0.000 claims description 4
- XMLKXSOLLPJOKY-UHFFFAOYSA-N 3-methoxy-n,n,2,6-tetramethylaniline Chemical compound COC1=CC=C(C)C(N(C)C)=C1C XMLKXSOLLPJOKY-UHFFFAOYSA-N 0.000 claims description 3
- JCEXIYBOKLOJKX-UHFFFAOYSA-N 4-ethoxy-n,n,2,6-tetramethylaniline Chemical compound CCOC1=CC(C)=C(N(C)C)C(C)=C1 JCEXIYBOKLOJKX-UHFFFAOYSA-N 0.000 claims description 3
- SSJJXGZKZZUROB-UHFFFAOYSA-N 4-methoxy-n,n,2,6-tetramethylaniline Chemical compound COC1=CC(C)=C(N(C)C)C(C)=C1 SSJJXGZKZZUROB-UHFFFAOYSA-N 0.000 claims description 3
- 239000011247 coating layer Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 2
- 229920000084 Gum arabic Polymers 0.000 claims description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 2
- 241000978776 Senegalia senegal Species 0.000 claims description 2
- 239000000205 acacia gum Substances 0.000 claims description 2
- 235000010489 acacia gum Nutrition 0.000 claims description 2
- 229920006322 acrylamide copolymer Polymers 0.000 claims description 2
- 229920001577 copolymer Polymers 0.000 claims description 2
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 2
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 2
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 2
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 claims description 2
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 claims description 2
- OMNKZBIFPJNNIO-UHFFFAOYSA-N n-(2-methyl-4-oxopentan-2-yl)prop-2-enamide Chemical compound CC(=O)CC(C)(C)NC(=O)C=C OMNKZBIFPJNNIO-UHFFFAOYSA-N 0.000 claims description 2
- 229920002401 polyacrylamide Polymers 0.000 claims description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 2
- 235000013772 propylene glycol Nutrition 0.000 claims description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 230000001568 sexual effect Effects 0.000 claims 1
- 239000000654 additive Substances 0.000 description 18
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical class [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 17
- 239000011248 coating agent Substances 0.000 description 15
- 238000000576 coating method Methods 0.000 description 15
- 230000000996 additive effect Effects 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000001989 diazonium salts Chemical class 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000011701 zinc Substances 0.000 description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 4
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 4
- 238000006303 photolysis reaction Methods 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- CCIAVEMREXZXAK-UHFFFAOYSA-M 4-(dimethylamino)benzenediazonium;chloride Chemical compound [Cl-].CN(C)C1=CC=C([N+]#N)C=C1 CCIAVEMREXZXAK-UHFFFAOYSA-M 0.000 description 3
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 3
- 239000013522 chelant Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 3
- 238000004448 titration Methods 0.000 description 3
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 2
- ZVUJMNCTXGSXSQ-UHFFFAOYSA-N 3,5-dimethyl-4-nitrosophenol Chemical compound CC1=CC(O)=CC(C)=C1N=O ZVUJMNCTXGSXSQ-UHFFFAOYSA-N 0.000 description 2
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 description 2
- PWRDKGULBIYXQH-UHFFFAOYSA-N 3-methoxy-N,N,2,6-tetramethylaniline hydrochloride Chemical compound Cl.COC=1C(=C(N(C)C)C(=CC1)C)C PWRDKGULBIYXQH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 2
- 229940008406 diethyl sulfate Drugs 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- SCVRZFQSPISLTD-UHFFFAOYSA-N n,n,2,6-tetramethylaniline Chemical compound CN(C)C1=C(C)C=CC=C1C SCVRZFQSPISLTD-UHFFFAOYSA-N 0.000 description 2
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 230000001235 sensitizing effect Effects 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- PZDSMFLJSCJUHJ-UHFFFAOYSA-M 2-(dimethylamino)benzenediazonium;chloride Chemical compound [Cl-].CN(C)C1=CC=CC=C1[N+]#N PZDSMFLJSCJUHJ-UHFFFAOYSA-M 0.000 description 1
- WVGMYVWWJSIIFJ-UHFFFAOYSA-N 2-methoxybenzenediazonium Chemical compound COC1=CC=CC=C1[N+]#N WVGMYVWWJSIIFJ-UHFFFAOYSA-N 0.000 description 1
- NAXOYKLRIQCXJR-UHFFFAOYSA-N 3-ethoxy-n,n,2,6-tetramethylaniline Chemical compound CCOC1=CC=C(C)C(N(C)C)=C1C NAXOYKLRIQCXJR-UHFFFAOYSA-N 0.000 description 1
- YFCXTPKUVYRXFI-UHFFFAOYSA-M 4-(diethylamino)benzenediazonium;chloride Chemical compound [Cl-].CCN(CC)C1=CC=C([N+]#N)C=C1 YFCXTPKUVYRXFI-UHFFFAOYSA-M 0.000 description 1
- UCYWXQOGYOCALN-UHFFFAOYSA-M 4-(dimethylamino)-2-methylbenzenediazonium chloride Chemical compound [Cl-].CN(C)C1=CC(C)=C(C=C1)[N+]#N UCYWXQOGYOCALN-UHFFFAOYSA-M 0.000 description 1
- MOXBCYIWIODTKI-UHFFFAOYSA-N 4-(dimethylamino)benzenediazonium Chemical compound CN(C)C1=CC=C([N+]#N)C=C1 MOXBCYIWIODTKI-UHFFFAOYSA-N 0.000 description 1
- DEBLFAIODZFPHG-UHFFFAOYSA-L 4-(dimethylamino)benzenediazonium;sulfate Chemical compound [O-]S([O-])(=O)=O.CN(C)C1=CC=C([N+]#N)C=C1.CN(C)C1=CC=C([N+]#N)C=C1 DEBLFAIODZFPHG-UHFFFAOYSA-L 0.000 description 1
- LFKVCVGVGODJQN-UHFFFAOYSA-M 4-[ethyl(2-hydroxyethyl)amino]benzenediazonium;chloride Chemical compound [Cl-].OCCN(CC)C1=CC=C([N+]#N)C=C1 LFKVCVGVGODJQN-UHFFFAOYSA-M 0.000 description 1
- KIKNVHOQRRODNE-UHFFFAOYSA-N 4-ethoxy-n,n,2,6-tetramethylaniline;hydrochloride Chemical compound Cl.CCOC1=CC(C)=C(N(C)C)C(C)=C1 KIKNVHOQRRODNE-UHFFFAOYSA-N 0.000 description 1
- XFMUCDRJXZLSNE-UHFFFAOYSA-N 4-methoxy-2,6-dimethylaniline Chemical compound COC1=CC(C)=C(N)C(C)=C1 XFMUCDRJXZLSNE-UHFFFAOYSA-N 0.000 description 1
- KHXUUPPXJWVTHH-UHFFFAOYSA-M 4-methoxybenzenediazonium;chloride Chemical compound [Cl-].COC1=CC=C([N+]#N)C=C1 KHXUUPPXJWVTHH-UHFFFAOYSA-M 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- CIZVQWNPBGYCGK-UHFFFAOYSA-N benzenediazonium Chemical compound N#[N+]C1=CC=CC=C1 CIZVQWNPBGYCGK-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 159000000014 iron salts Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- XLUDCYVRAHZAGL-UHFFFAOYSA-N n,n,2,6-tetramethyl-3-nitroaniline Chemical compound CN(C)C1=C(C)C=CC([N+]([O-])=O)=C1C XLUDCYVRAHZAGL-UHFFFAOYSA-N 0.000 description 1
- KECFTDQVRIBMCH-UHFFFAOYSA-N n,n-diethyl-2,6-dimethylaniline Chemical compound CCN(CC)C1=C(C)C=CC=C1C KECFTDQVRIBMCH-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 150000002832 nitroso derivatives Chemical class 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 238000001782 photodegradation Methods 0.000 description 1
- 230000015843 photosynthesis, light reaction Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- HVTHJRMZXBWFNE-UHFFFAOYSA-J sodium zincate Chemical compound [OH-].[OH-].[OH-].[OH-].[Na+].[Na+].[Zn+2] HVTHJRMZXBWFNE-UHFFFAOYSA-J 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/52—Compositions containing diazo compounds as photosensitive substances
- G03C1/60—Compositions containing diazo compounds as photosensitive substances with macromolecular additives
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Formation Of Various Coating Films On Cathode Ray Tubes And Lamps (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8571981A JPS57201230A (en) | 1981-06-05 | 1981-06-05 | Photosensitive composition and formation of pattern using said composition |
| KR1019810002279A KR850001415B1 (ko) | 1980-07-04 | 1981-06-23 | 감광성 조성물(感光性組成物) |
| US06/279,849 US4377630A (en) | 1980-07-04 | 1981-07-02 | Photosensitive composition |
| DE8181303053T DE3169809D1 (en) | 1980-07-04 | 1981-07-03 | Photosensitive composition and pattern forming process using same |
| EP81303053A EP0043716B1 (fr) | 1980-07-04 | 1981-07-03 | Composition photosensible et procédé de formation d'images avec cette composition |
| US06/427,586 US4409313A (en) | 1980-07-04 | 1982-09-29 | Powder deposition to form pattern on light imaged photosensitive diazonium salt coating having salt of aromatic amine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8571981A JPS57201230A (en) | 1981-06-05 | 1981-06-05 | Photosensitive composition and formation of pattern using said composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57201230A JPS57201230A (en) | 1982-12-09 |
| JPH0319535B2 true JPH0319535B2 (fr) | 1991-03-15 |
Family
ID=13866640
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8571981A Granted JPS57201230A (en) | 1980-07-04 | 1981-06-05 | Photosensitive composition and formation of pattern using said composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57201230A (fr) |
-
1981
- 1981-06-05 JP JP8571981A patent/JPS57201230A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57201230A (en) | 1982-12-09 |
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