JPS6140977B2 - - Google Patents
Info
- Publication number
- JPS6140977B2 JPS6140977B2 JP9559777A JP9559777A JPS6140977B2 JP S6140977 B2 JPS6140977 B2 JP S6140977B2 JP 9559777 A JP9559777 A JP 9559777A JP 9559777 A JP9559777 A JP 9559777A JP S6140977 B2 JPS6140977 B2 JP S6140977B2
- Authority
- JP
- Japan
- Prior art keywords
- diazo
- formula
- hydroxy
- compound
- component
- 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
- 230000008878 coupling Effects 0.000 claims description 20
- 238000010168 coupling process Methods 0.000 claims description 20
- 238000005859 coupling reaction Methods 0.000 claims description 20
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000001174 sulfone group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 239000000463 material Substances 0.000 description 16
- 239000000975 dye Substances 0.000 description 15
- -1 2,4-dihydroxy-3-methylbenzaldehyde phenylhydrazone Chemical compound 0.000 description 13
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 239000000987 azo dye Substances 0.000 description 8
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 7
- 150000008049 diazo compounds Chemical class 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 238000000034 method Methods 0.000 description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 5
- 229930182490 saponin Natural products 0.000 description 5
- 150000007949 saponins Chemical class 0.000 description 5
- ZTMADXFOCUXMJE-UHFFFAOYSA-N 2-methylbenzene-1,3-diol Chemical compound CC1=C(O)C=CC=C1O ZTMADXFOCUXMJE-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 4
- 229960001948 caffeine Drugs 0.000 description 4
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 4
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000032683 aging Effects 0.000 description 3
- LOJVMPWEUHXTBY-UHFFFAOYSA-N chembl1734596 Chemical compound OC1=CC(O)=CC=C1C=NNC1=NC2=CC=CC=C2S1 LOJVMPWEUHXTBY-UHFFFAOYSA-N 0.000 description 3
- 238000005562 fading Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
- OEIQOKPNLCRCFM-UHFFFAOYSA-N 1-[(1,3-benzothiazol-2-ylhydrazinylidene)methyl]naphthalen-2-ol Chemical compound Oc1ccc2ccccc2c1C=NNc1nc2ccccc2s1 OEIQOKPNLCRCFM-UHFFFAOYSA-N 0.000 description 2
- WXHLLJAMBQLULT-UHFFFAOYSA-N 2-[[6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-yl]amino]-n-(2-methyl-6-sulfanylphenyl)-1,3-thiazole-5-carboxamide;hydrate Chemical compound O.C=1C(N2CCN(CCO)CC2)=NC(C)=NC=1NC(S1)=NC=C1C(=O)NC1=C(C)C=CC=C1S WXHLLJAMBQLULT-UHFFFAOYSA-N 0.000 description 2
- 239000001431 2-methylbenzaldehyde Substances 0.000 description 2
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 2
- VYHNSPUVKZPCDZ-UHFFFAOYSA-N 3-hydroxy-n-(2-hydroxyethyl)naphthalene-2-carboxamide Chemical compound C1=CC=C2C=C(O)C(C(=O)NCCO)=CC2=C1 VYHNSPUVKZPCDZ-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 235000011090 malic acid Nutrition 0.000 description 2
- 150000004780 naphthols Chemical class 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229960000278 theophylline Drugs 0.000 description 2
- NJPKYOIXTSGVAN-UHFFFAOYSA-K trisodium;naphthalene-1,3,6-trisulfonate Chemical compound [Na+].[Na+].[Na+].[O-]S(=O)(=O)C1=CC(S([O-])(=O)=O)=CC2=CC(S(=O)(=O)[O-])=CC=C21 NJPKYOIXTSGVAN-UHFFFAOYSA-K 0.000 description 2
- 150000005207 1,3-dihydroxybenzenes Chemical class 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HOIGMVLXDOFNKW-UHFFFAOYSA-N 1-(2,5-dibutoxy-4-diazocyclohexa-1,5-dien-1-yl)piperidine Chemical compound C1=C(OCCCC)C(=[N+]=[N-])CC(OCCCC)=C1N1CCCCC1 HOIGMVLXDOFNKW-UHFFFAOYSA-N 0.000 description 1
- FIBIJMTYLGTSQB-UHFFFAOYSA-N 1-(4-diazo-2,5-diethoxycyclohexa-1,5-dien-1-yl)pyrrolidine Chemical compound C1=C(OCC)C(=[N+]=[N-])CC(OCC)=C1N1CCCC1 FIBIJMTYLGTSQB-UHFFFAOYSA-N 0.000 description 1
- RWCAXNBYPKHDBR-UHFFFAOYSA-N 1-(4-diazocyclohexa-1,5-dien-1-yl)pyrrolidine Chemical compound C1=CC(=[N+]=[N-])CC=C1N1CCCC1 RWCAXNBYPKHDBR-UHFFFAOYSA-N 0.000 description 1
- FHDQFPCQZMLBFE-UHFFFAOYSA-N 1-[(4e)-4-diazo-2-methylcyclohexa-1,5-dien-1-yl]pyrrolidine Chemical compound C1=CC(=[N+]=[N-])CC(C)=C1N1CCCC1 FHDQFPCQZMLBFE-UHFFFAOYSA-N 0.000 description 1
- CEPBCMLPAGAVDY-UHFFFAOYSA-N 2,5-dibutoxy-n,n-dibutyl-4-diazocyclohexa-1,5-dien-1-amine Chemical compound CCCCOC1=C(N(CCCC)CCCC)C=C(OCCCC)C(=[N+]=[N-])C1 CEPBCMLPAGAVDY-UHFFFAOYSA-N 0.000 description 1
- HRVASZFVRTZSFO-UHFFFAOYSA-N 2-[(4-diazocyclohexa-1,5-dien-1-yl)-ethylamino]ethanol Chemical compound OCCN(CC)C1=CCC(=[N+]=[N-])C=C1 HRVASZFVRTZSFO-UHFFFAOYSA-N 0.000 description 1
- NTCCNERMXRIPTR-UHFFFAOYSA-N 2-hydroxy-1-naphthaldehyde Chemical compound C1=CC=CC2=C(C=O)C(O)=CC=C21 NTCCNERMXRIPTR-UHFFFAOYSA-N 0.000 description 1
- UIKUBYKUYUSRSM-UHFFFAOYSA-N 3-morpholinopropylamine Chemical compound NCCCN1CCOCC1 UIKUBYKUYUSRSM-UHFFFAOYSA-N 0.000 description 1
- VVKHPAIJUBQTMQ-UHFFFAOYSA-N 4-(2,5-dibutoxy-4-diazocyclohexa-1,5-dien-1-yl)morpholine Chemical compound C1=C(OCCCC)C(=[N+]=[N-])CC(OCCCC)=C1N1CCOCC1 VVKHPAIJUBQTMQ-UHFFFAOYSA-N 0.000 description 1
- LRUJNDUWNJTRHJ-UHFFFAOYSA-N 4-(4-diazo-2,5-diethoxycyclohexa-1,5-dien-1-yl)morpholine Chemical compound C1=C(OCC)C(=[N+]=[N-])CC(OCC)=C1N1CCOCC1 LRUJNDUWNJTRHJ-UHFFFAOYSA-N 0.000 description 1
- YMYLGFCECMUHHI-UHFFFAOYSA-N 4-(4-diazo-2,5-dimethoxycyclohexa-1,5-dien-1-yl)morpholine Chemical compound C1=C(OC)C(=[N+]=[N-])CC(OC)=C1N1CCOCC1 YMYLGFCECMUHHI-UHFFFAOYSA-N 0.000 description 1
- SCETWWDGKCBPMK-UHFFFAOYSA-N 4-[(4e)-4-diazocyclohexa-1,5-dien-1-yl]morpholine Chemical compound C1=CC(=[N+]=[N-])CC=C1N1CCOCC1 SCETWWDGKCBPMK-UHFFFAOYSA-N 0.000 description 1
- ZNNMXRMLLZVIRS-UHFFFAOYSA-N 4-[(phenylhydrazinylidene)methyl]benzene-1,3-diol Chemical compound OC1=CC(O)=CC=C1C=NNC1=CC=CC=C1 ZNNMXRMLLZVIRS-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FEWJPZIEWOKRBE-XIXRPRMCSA-N Mesotartaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-XIXRPRMCSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- DPTJJWNFQHUYCX-UHFFFAOYSA-N Oc1ccc(C=NNc2ccc3ccccc3c2)c(O)c1 Chemical compound Oc1ccc(C=NNc2ccc3ccccc3c2)c(O)c1 DPTJJWNFQHUYCX-UHFFFAOYSA-N 0.000 description 1
- 239000004288 Sodium dehydroacetate Substances 0.000 description 1
- 235000005811 Viola adunca Nutrition 0.000 description 1
- 240000009038 Viola odorata Species 0.000 description 1
- 235000013487 Viola odorata Nutrition 0.000 description 1
- 235000002254 Viola papilionacea Nutrition 0.000 description 1
- PXTVLXYDSJINFF-UHFFFAOYSA-N [N+](=[N-])=C1CC(=C(C=C1OCCC)N1CCOCC1)OCCC Chemical compound [N+](=[N-])=C1CC(=C(C=C1OCCC)N1CCOCC1)OCCC PXTVLXYDSJINFF-UHFFFAOYSA-N 0.000 description 1
- SMHMZISJETWZKT-UHFFFAOYSA-N [N+](=[N-])=C1CC(=C(N(CCO)CC2=CC=CC=C2)C=C1OCCCC)OCCCC Chemical compound [N+](=[N-])=C1CC(=C(N(CCO)CC2=CC=CC=C2)C=C1OCCCC)OCCCC SMHMZISJETWZKT-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- WWIIENGSINYUES-LDADJPATSA-N chembl1990184 Chemical compound OC1=CC=C2C=CC=CC2=C1\C=N\NC1=CC=CC=C1 WWIIENGSINYUES-LDADJPATSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- VEBVLEHQOPUIBH-UHFFFAOYSA-N n-benzyl-2,5-dibutoxy-4-diazo-n-ethylcyclohexa-1,5-dien-1-amine Chemical compound C1=C(OCCCC)C(=[N+]=[N-])CC(OCCCC)=C1N(CC)CC1=CC=CC=C1 VEBVLEHQOPUIBH-UHFFFAOYSA-N 0.000 description 1
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical compound [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 1
- URXNVXOMQQCBHS-UHFFFAOYSA-N naphthalene;sodium Chemical compound [Na].C1=CC=CC2=CC=CC=C21 URXNVXOMQQCBHS-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- JVUYWILPYBCNNG-UHFFFAOYSA-N potassium;oxido(oxo)borane Chemical compound [K+].[O-]B=O JVUYWILPYBCNNG-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229940079839 sodium dehydroacetate Drugs 0.000 description 1
- 235000019259 sodium dehydroacetate Nutrition 0.000 description 1
- DSOWAKKSGYUMTF-GZOLSCHFSA-M sodium;(1e)-1-(6-methyl-2,4-dioxopyran-3-ylidene)ethanolate Chemical compound [Na+].C\C([O-])=C1/C(=O)OC(C)=CC1=O DSOWAKKSGYUMTF-GZOLSCHFSA-M 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 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
- G03C1/58—Coupling substances therefor
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9559777A JPS5430023A (en) | 1977-08-11 | 1977-08-11 | Diazo copying method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9559777A JPS5430023A (en) | 1977-08-11 | 1977-08-11 | Diazo copying method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5430023A JPS5430023A (en) | 1979-03-06 |
| JPS6140977B2 true JPS6140977B2 (enrdf_load_stackoverflow) | 1986-09-12 |
Family
ID=14141964
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9559777A Granted JPS5430023A (en) | 1977-08-11 | 1977-08-11 | Diazo copying method |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5430023A (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5953833A (ja) * | 1982-09-22 | 1984-03-28 | Ricoh Co Ltd | 画像形成組成物 |
| US5753700A (en) * | 1994-12-28 | 1998-05-19 | Ono Pharmaceutical Co., Ltd. | Naphthyloxyacetic acid derivatives |
-
1977
- 1977-08-11 JP JP9559777A patent/JPS5430023A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5430023A (en) | 1979-03-06 |
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