JPS6254802B2 - - Google Patents
Info
- Publication number
- JPS6254802B2 JPS6254802B2 JP8763779A JP8763779A JPS6254802B2 JP S6254802 B2 JPS6254802 B2 JP S6254802B2 JP 8763779 A JP8763779 A JP 8763779A JP 8763779 A JP8763779 A JP 8763779A JP S6254802 B2 JPS6254802 B2 JP S6254802B2
- Authority
- JP
- Japan
- Prior art keywords
- quinolinium
- ion
- structural unit
- group
- water
- 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
- -1 halogen ion Chemical class 0.000 claims description 24
- 239000000463 material Substances 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 150000001450 anions Chemical class 0.000 claims description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 3
- 229940085991 phosphate ion Drugs 0.000 claims description 2
- 239000011347 resin Substances 0.000 description 27
- 229920005989 resin Polymers 0.000 description 27
- 239000000243 solution Substances 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 230000035945 sensitivity Effects 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 10
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 8
- 229920002554 vinyl polymer Polymers 0.000 description 8
- CUARLQDWYSRQDF-UHFFFAOYSA-N 5-Nitroacenaphthene Chemical compound C1CC2=CC=CC3=C2C1=CC=C3[N+](=O)[O-] CUARLQDWYSRQDF-UHFFFAOYSA-N 0.000 description 7
- 229940114081 cinnamate Drugs 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- 229920002689 polyvinyl acetate Polymers 0.000 description 7
- 239000011118 polyvinyl acetate Substances 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 102000004190 Enzymes Human genes 0.000 description 6
- 108090000790 Enzymes Proteins 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- YVXDRFYHWWPSOA-BQYQJAHWSA-N 1-methyl-4-[(e)-2-phenylethenyl]pyridin-1-ium Chemical group C1=C[N+](C)=CC=C1\C=C\C1=CC=CC=C1 YVXDRFYHWWPSOA-BQYQJAHWSA-N 0.000 description 5
- SPAGXWZCVRGWDO-UHFFFAOYSA-N 4-(2-quinolin-2-ylethenyl)benzaldehyde Chemical compound C1=CC(C=O)=CC=C1C=CC1=CC=C(C=CC=C2)C2=N1 SPAGXWZCVRGWDO-UHFFFAOYSA-N 0.000 description 5
- 239000004372 Polyvinyl alcohol Substances 0.000 description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229920002451 polyvinyl alcohol Polymers 0.000 description 5
- QJNKRLXEVGOXGC-UHFFFAOYSA-N 4-[2-(1-methylquinolin-1-ium-4-yl)ethenyl]benzaldehyde Chemical compound C12=CC=CC=C2[N+](C)=CC=C1C=CC1=CC=C(C=O)C=C1 QJNKRLXEVGOXGC-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 229920002120 photoresistant polymer Polymers 0.000 description 4
- SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical compound C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 description 4
- 125000005504 styryl group Chemical group 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- 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 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- REEBWSYYNPPSKV-UHFFFAOYSA-N 3-[(4-formylphenoxy)methyl]thiophene-2-carbonitrile Chemical compound C1=CC(C=O)=CC=C1OCC1=C(C#N)SC=C1 REEBWSYYNPPSKV-UHFFFAOYSA-N 0.000 description 2
- IKCKWWARXSGENG-UHFFFAOYSA-N 4-(2-quinolin-4-ylethenyl)benzaldehyde Chemical compound C1=CC(C=O)=CC=C1C=CC1=CC=NC2=CC=CC=C12 IKCKWWARXSGENG-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical group OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 206010034972 Photosensitivity reaction Diseases 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical class N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000006359 acetalization reaction Methods 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 230000003100 immobilizing effect Effects 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 230000036211 photosensitivity Effects 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- UCFSULAKAYDAAE-UHFFFAOYSA-N quinolin-1-ium;iodide Chemical compound I.N1=CC=CC2=CC=CC=C21 UCFSULAKAYDAAE-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XXCFMHCLWHXDAV-UHFFFAOYSA-M 1,2-dimethylquinolin-1-ium;iodide Chemical compound [I-].C1=CC=CC2=[N+](C)C(C)=CC=C21 XXCFMHCLWHXDAV-UHFFFAOYSA-M 0.000 description 1
- OHQGKTJQWANGLW-UHFFFAOYSA-N 1,4-dimethylquinolin-1-ium Chemical compound C1=CC=C2C(C)=CC=[N+](C)C2=C1 OHQGKTJQWANGLW-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- GJTITKGFCXYHQX-UHFFFAOYSA-N 4-(2,2-dimethoxyethoxy)benzaldehyde Chemical compound COC(OC)COC1=CC=C(C=O)C=C1 GJTITKGFCXYHQX-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
- 238000000862 absorption spectrum Methods 0.000 description 1
- 125000004036 acetal group Chemical group 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 1
- 150000003935 benzaldehydes Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-O hydron;quinoline Chemical compound [NH+]1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-O 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 238000001259 photo etching Methods 0.000 description 1
- 238000011907 photodimerization Methods 0.000 description 1
- JVQPSLMSWPIJKT-UHFFFAOYSA-N quinoline styrene Chemical group C=Cc1ccccc1.c1ccc2ncccc2c1 JVQPSLMSWPIJKT-UHFFFAOYSA-N 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP8763779A JPS5611906A (en) | 1979-07-11 | 1979-07-11 | Photo-insolubilizable polyvinyl alcohol derivative and its preparation |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP8763779A JPS5611906A (en) | 1979-07-11 | 1979-07-11 | Photo-insolubilizable polyvinyl alcohol derivative and its preparation |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP20797382A Division JPS59521B2 (ja) | 1982-11-26 | 1982-11-26 | 光不溶化性感光材料の製造方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5611906A JPS5611906A (en) | 1981-02-05 |
JPS6254802B2 true JPS6254802B2 (en, 2012) | 1987-11-17 |
Family
ID=13920487
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP8763779A Granted JPS5611906A (en) | 1979-07-11 | 1979-07-11 | Photo-insolubilizable polyvinyl alcohol derivative and its preparation |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS5611906A (en, 2012) |
Families Citing this family (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4444868A (en) * | 1981-08-06 | 1984-04-24 | Agency Of Industrial Science & Technology | Photosensitive composition |
JPS58129976A (ja) * | 1982-01-27 | 1983-08-03 | Agency Of Ind Science & Technol | 微生物菌体の固定化法 |
JPS59113007A (ja) * | 1982-12-18 | 1984-06-29 | Mitsui Toatsu Chem Inc | オレフインの共重合方法 |
JPS59154442A (ja) * | 1983-02-22 | 1984-09-03 | Oji Paper Co Ltd | 画像形成用感光性フイルム |
JPS59185332A (ja) * | 1983-04-06 | 1984-10-20 | Agency Of Ind Science & Technol | 感光性樹脂組成物 |
JPS59211037A (ja) * | 1983-05-17 | 1984-11-29 | Agency Of Ind Science & Technol | 感光性樹脂組成物 |
JPS6187153A (ja) * | 1984-09-11 | 1986-05-02 | Agency Of Ind Science & Technol | 感光性樹脂組成物 |
JPS62109040A (ja) * | 1985-11-08 | 1987-05-20 | Nippon Kayaku Co Ltd | 感光性樹脂組成物 |
JPH0644151B2 (ja) * | 1986-10-17 | 1994-06-08 | 日本化薬株式会社 | 可染性樹脂膜のパタ−ン形成法 |
JPH0713099B2 (ja) | 1988-12-14 | 1995-02-15 | 工業技術院長 | 感光性ポリビニルアルコール誘導体 |
JP3561061B2 (ja) * | 1995-12-11 | 2004-09-02 | 東洋合成工業株式会社 | ポリビニルアルコール系感光性樹脂および感光性樹脂組成物並びにそれを用いたパターン形成方法 |
JPH10301272A (ja) * | 1997-04-30 | 1998-11-13 | Toyo Gosei Kogyo Kk | 感光性組成物及びパターン形成方法 |
JP3771705B2 (ja) * | 1998-03-12 | 2006-04-26 | 互応化学工業株式会社 | 感光性樹脂組成物及びプリント配線板製造用フォトレジストインク |
JP3771714B2 (ja) | 1998-05-12 | 2006-04-26 | 互応化学工業株式会社 | 感光性樹脂組成物及びプリント配線板製造用フォトソルダーレジストインク |
US6020093A (en) * | 1998-05-13 | 2000-02-01 | Toyo Gosei Kogyo, Ltd. | Photosensitive compounds, photosensitive resin compositions, and pattern formation method making use of the compounds or compositions |
TWI224715B (en) * | 1998-08-05 | 2004-12-01 | Toyo Gosei Kogyo Kk | Photosensitive resin derived from saponified poly(vinyl acetate) |
US6444391B2 (en) | 1998-09-24 | 2002-09-03 | Toyo Gosei Kogyo Co., Ltd. | Photosensitive compositions and pattern formation method |
US6797452B2 (en) | 1999-06-04 | 2004-09-28 | Toyo Gosei Kogyo Co., Ltd. | Photosensitive composition comprising photosensitive saponified poly(vinyl acetate) and pattern formation method making use of the composition |
EP1058154A1 (en) * | 1999-06-04 | 2000-12-06 | Toyo Gosei Kogyo Co., Ltd. | Composition comprising photosensitive saponified poly(vinyl acetate) and pattern formation method making use of the composition |
JP4390237B2 (ja) | 2000-02-14 | 2009-12-24 | 東洋合成工業株式会社 | 感光性化合物及び感光性樹脂 |
KR20010107288A (ko) * | 2000-05-26 | 2001-12-07 | 박이순 | 감광성 수지의 제조 방법 |
-
1979
- 1979-07-11 JP JP8763779A patent/JPS5611906A/ja active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS5611906A (en) | 1981-02-05 |
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