JPS61184534A - 感光性樹脂水溶液の製造方法 - Google Patents
感光性樹脂水溶液の製造方法Info
- Publication number
- JPS61184534A JPS61184534A JP2450085A JP2450085A JPS61184534A JP S61184534 A JPS61184534 A JP S61184534A JP 2450085 A JP2450085 A JP 2450085A JP 2450085 A JP2450085 A JP 2450085A JP S61184534 A JPS61184534 A JP S61184534A
- Authority
- JP
- Japan
- Prior art keywords
- ion exchange
- reaction
- exchange resin
- polyvinyl alcohol
- photosensitive resin
- 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.)
- Granted
Links
- 239000011347 resin Substances 0.000 title claims abstract description 43
- 229920005989 resin Polymers 0.000 title claims abstract description 43
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 239000007864 aqueous solution Substances 0.000 title description 23
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims abstract description 32
- 239000003456 ion exchange resin Substances 0.000 claims abstract description 32
- 229920003303 ion-exchange polymer Polymers 0.000 claims abstract description 32
- 229920002451 polyvinyl alcohol Polymers 0.000 claims abstract description 27
- 239000004372 Polyvinyl alcohol Substances 0.000 claims abstract description 24
- 238000006243 chemical reaction Methods 0.000 claims abstract description 24
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims abstract description 15
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims abstract description 15
- 239000012736 aqueous medium Substances 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 238000006359 acetalization reaction Methods 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 2
- 125000005504 styryl group Chemical group 0.000 abstract description 20
- -1 styryl compound Chemical class 0.000 abstract description 18
- 230000002378 acidificating effect Effects 0.000 abstract description 17
- 150000001875 compounds Chemical class 0.000 abstract description 12
- 239000003054 catalyst Substances 0.000 abstract description 7
- 238000005342 ion exchange Methods 0.000 abstract description 7
- 239000000203 mixture Substances 0.000 abstract description 7
- 230000007935 neutral effect Effects 0.000 abstract description 2
- 238000005755 formation reaction Methods 0.000 abstract 2
- PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 23
- 238000000034 method Methods 0.000 description 16
- 239000000243 solution Substances 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 230000035945 sensitivity Effects 0.000 description 6
- 238000011161 development Methods 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000007865 diluting Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- YVXDRFYHWWPSOA-BQYQJAHWSA-N 1-methyl-4-[(e)-2-phenylethenyl]pyridin-1-ium Chemical compound C1=C[N+](C)=CC=C1\C=C\C1=CC=CC=C1 YVXDRFYHWWPSOA-BQYQJAHWSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- ZPFAVCIQZKRBGF-UHFFFAOYSA-N 1,3,2-dioxathiolane 2,2-dioxide Chemical compound O=S1(=O)OCCO1 ZPFAVCIQZKRBGF-UHFFFAOYSA-N 0.000 description 1
- YHWQNYJRIDKJOD-UHFFFAOYSA-O 2-[2-[2-(4-formylphenyl)ethenyl]pyridin-1-ium-1-yl]acetamide Chemical compound NC(=O)C[N+]1=CC=CC=C1C=CC1=CC=C(C=O)C=C1 YHWQNYJRIDKJOD-UHFFFAOYSA-O 0.000 description 1
- BQTGZDOWLHAXPI-UHFFFAOYSA-O 2-[4-[2-(4-formylphenyl)ethenyl]pyridin-1-ium-1-yl]acetamide Chemical compound C1=C[N+](CC(=O)N)=CC=C1C=CC1=CC=C(C=O)C=C1 BQTGZDOWLHAXPI-UHFFFAOYSA-O 0.000 description 1
- PCUPSMXBHNADJG-UHFFFAOYSA-N 3-[2-(1-methylpyridin-1-ium-2-yl)ethenyl]benzaldehyde Chemical compound C[N+]1=CC=CC=C1C=CC1=CC=CC(C=O)=C1 PCUPSMXBHNADJG-UHFFFAOYSA-N 0.000 description 1
- HIZVNNYJSVZBEI-UHFFFAOYSA-N 4-[2-(1-benzylpyridin-1-ium-2-yl)ethenyl]benzaldehyde Chemical compound C1=CC(C=O)=CC=C1C=CC1=CC=CC=[N+]1CC1=CC=CC=C1 HIZVNNYJSVZBEI-UHFFFAOYSA-N 0.000 description 1
- PIZINBUKAIYHQX-UHFFFAOYSA-N 4-[2-(1-benzylpyridin-1-ium-4-yl)ethenyl]benzaldehyde Chemical compound C1=CC(C=O)=CC=C1C=CC(C=C1)=CC=[N+]1CC1=CC=CC=C1 PIZINBUKAIYHQX-UHFFFAOYSA-N 0.000 description 1
- OJAQJUMWXAAWFQ-UHFFFAOYSA-N 4-[2-(1-ethylpyridin-1-ium-4-yl)ethenyl]benzaldehyde Chemical compound C1=C[N+](CC)=CC=C1C=CC1=CC=C(C=O)C=C1 OJAQJUMWXAAWFQ-UHFFFAOYSA-N 0.000 description 1
- UYLFDGWVBBDGSS-UHFFFAOYSA-N 4-[2-(1-ethylquinolin-1-ium-2-yl)ethenyl]benzaldehyde Chemical compound C1=CC2=CC=CC=C2[N+](CC)=C1C=CC1=CC=C(C=O)C=C1 UYLFDGWVBBDGSS-UHFFFAOYSA-N 0.000 description 1
- KCWZBAGKKWMNAI-UHFFFAOYSA-N 4-[2-(1-ethylquinolin-1-ium-4-yl)ethenyl]benzaldehyde Chemical compound C12=CC=CC=C2[N+](CC)=CC=C1C=CC1=CC=C(C=O)C=C1 KCWZBAGKKWMNAI-UHFFFAOYSA-N 0.000 description 1
- MTOZJUDAPRQZML-UHFFFAOYSA-N 4-[2-(1-methylpyridin-1-ium-2-yl)ethenyl]benzaldehyde Chemical compound C[N+]1=CC=CC=C1C=CC1=CC=C(C=O)C=C1 MTOZJUDAPRQZML-UHFFFAOYSA-N 0.000 description 1
- RYLOLRAYISQACV-UHFFFAOYSA-N 4-[2-(1-methylpyridin-1-ium-4-yl)ethenyl]benzaldehyde Chemical compound C1=C[N+](C)=CC=C1C=CC1=CC=C(C=O)C=C1 RYLOLRAYISQACV-UHFFFAOYSA-N 0.000 description 1
- CJPBOQVYIQSEPF-UHFFFAOYSA-N 4-[2-(1-methylquinolin-1-ium-2-yl)ethenyl]benzaldehyde Chemical compound C1=CC2=CC=CC=C2[N+](C)=C1C=CC1=CC=C(C=O)C=C1 CJPBOQVYIQSEPF-UHFFFAOYSA-N 0.000 description 1
- MPPXKIPCXOSEMW-UHFFFAOYSA-N 4-[2-[1-(2-hydroxyethyl)pyridin-1-ium-2-yl]ethenyl]benzaldehyde Chemical compound OCC[N+]1=CC=CC=C1C=CC1=CC=C(C=O)C=C1 MPPXKIPCXOSEMW-UHFFFAOYSA-N 0.000 description 1
- DWOIJHIIADRLSE-UHFFFAOYSA-N 4-[2-[1-(2-hydroxyethyl)pyridin-1-ium-4-yl]ethenyl]benzaldehyde Chemical compound C1=C[N+](CCO)=CC=C1C=CC1=CC=C(C=O)C=C1 DWOIJHIIADRLSE-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- LAIYXAHJVBOSGZ-UHFFFAOYSA-N C[S+]1C(C=CC=C2)=C2N=C1C=CC1=CC=C(C=O)C=C1 Chemical compound C[S+]1C(C=CC=C2)=C2N=C1C=CC1=CC=C(C=O)C=C1 LAIYXAHJVBOSGZ-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical group N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- JOPOVCBBYLSVDA-UHFFFAOYSA-N chromium(6+) Chemical compound [Cr+6] JOPOVCBBYLSVDA-UHFFFAOYSA-N 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0388—Macromolecular compounds which are rendered insoluble or differentially wettable with ethylenic or acetylenic bands in the side chains of the photopolymer
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2450085A JPS61184534A (ja) | 1985-02-13 | 1985-02-13 | 感光性樹脂水溶液の製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2450085A JPS61184534A (ja) | 1985-02-13 | 1985-02-13 | 感光性樹脂水溶液の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61184534A true JPS61184534A (ja) | 1986-08-18 |
| JPH0369100B2 JPH0369100B2 (enExample) | 1991-10-30 |
Family
ID=12139904
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2450085A Granted JPS61184534A (ja) | 1985-02-13 | 1985-02-13 | 感光性樹脂水溶液の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61184534A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63236031A (ja) * | 1987-03-25 | 1988-09-30 | Japan Synthetic Rubber Co Ltd | 感放射線性樹脂の製造方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4024159A (en) * | 1974-08-07 | 1977-05-17 | E. I. Du Pont De Nemours And Company | Process for the production of liquid acetals |
| JPS5832838A (ja) * | 1981-08-24 | 1983-02-25 | Daicel Chem Ind Ltd | メチルビニルエ−テルの連続的製造法 |
| JPS59102232A (ja) * | 1982-12-03 | 1984-06-13 | Agency Of Ind Science & Technol | スクリーン印刷版製造用感光性材料 |
-
1985
- 1985-02-13 JP JP2450085A patent/JPS61184534A/ja active Granted
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4024159A (en) * | 1974-08-07 | 1977-05-17 | E. I. Du Pont De Nemours And Company | Process for the production of liquid acetals |
| JPS5832838A (ja) * | 1981-08-24 | 1983-02-25 | Daicel Chem Ind Ltd | メチルビニルエ−テルの連続的製造法 |
| JPS59102232A (ja) * | 1982-12-03 | 1984-06-13 | Agency Of Ind Science & Technol | スクリーン印刷版製造用感光性材料 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63236031A (ja) * | 1987-03-25 | 1988-09-30 | Japan Synthetic Rubber Co Ltd | 感放射線性樹脂の製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0369100B2 (enExample) | 1991-10-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP3211039B2 (ja) | アルキルビスアシルホスフインオキシド | |
| DE69412684T2 (de) | Reaktive, polymere Farbstoffe | |
| JP2001049231A (ja) | 有機反射防止重合体およびその製造方法 | |
| JPH10500169A (ja) | ビニルベンジルチミン単量体およびそれから造られた重合体および製品 | |
| US4891300A (en) | Saponified polyvinyl acetate derivatives which are photosensitive resin compositions | |
| JPS61230138A (ja) | 感光性樹脂組成物 | |
| JPS6117141A (ja) | スクリーン製版用感光性樹脂組成物 | |
| US8916336B2 (en) | Patterning method using thiosulfate polymer and metal nanoparticles | |
| US4209581A (en) | Soluble photosensitive resin composition | |
| US5334485A (en) | Acid soluble photo-resist comprising a photosensitive polymer | |
| JPH02160807A (ja) | 感光性ポリビニルアルコール誘導体 | |
| JPS59102232A (ja) | スクリーン印刷版製造用感光性材料 | |
| US4048146A (en) | Radiation sensitive polymers of oxygen-substituted maleimides and elements containing same | |
| JPS61184534A (ja) | 感光性樹脂水溶液の製造方法 | |
| JP7472917B2 (ja) | パターン形成方法、感放射線性組成物及び包摂化合物 | |
| JPH03219249A (ja) | 高速スクリーン印刷組成物 | |
| JPS62277364A (ja) | フエナントロイミダゾ−ル化合物、その製造方法及びこれを使用した光重合性被覆材料乃至記録材料 | |
| JPS59176303A (ja) | 感光性樹脂水溶液の精製方法 | |
| JPS63172154A (ja) | 感光性組成物及びこれを含有する感光性記録材料 | |
| JPH09328482A (ja) | クマリン化合物およびその用途 | |
| JPS6281403A (ja) | 光重合開始剤組成物 | |
| JPH04502521A (ja) | コバルト（３）化合物および酸化還元移行性配位子を含有するフォトレジスト組成物 | |
| JPS62288829A (ja) | 感光性混合物及び感光性記録材料 | |
| JPH1017604A (ja) | 可視光感光性樹脂組成物およびその用途 | |
| US3471294A (en) | Photosensitive polyvinyl butyral lacquer containing water-insoluble chromates or bichromates |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |