JPS6140978B2 - - Google Patents
Info
- Publication number
- JPS6140978B2 JPS6140978B2 JP10200477A JP10200477A JPS6140978B2 JP S6140978 B2 JPS6140978 B2 JP S6140978B2 JP 10200477 A JP10200477 A JP 10200477A JP 10200477 A JP10200477 A JP 10200477A JP S6140978 B2 JPS6140978 B2 JP S6140978B2
- Authority
- JP
- Japan
- Prior art keywords
- diazo
- copying
- coupling component
- component
- compound
- 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 16
- 238000010168 coupling process Methods 0.000 claims description 16
- 238000005859 coupling reaction Methods 0.000 claims description 16
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl 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
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000000463 material Substances 0.000 description 14
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 10
- 150000008049 diazo compounds Chemical class 0.000 description 7
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 5
- 239000000987 azo dye Substances 0.000 description 5
- 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-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
- -1 4-diazo-3-methoxyphenylpiperidine Chemical compound 0.000 description 3
- 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 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 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
- 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 2
- FEWJPZIEWOKRBE-XIXRPRMCSA-N Mesotartaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-XIXRPRMCSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-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
- 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
- VWYSHPVBENQCRM-UHFFFAOYSA-N 4-(4-diazo-2,5-diethoxycyclohexa-1,5-dien-1-yl)morpholine hydrochloride Chemical compound Cl.C1=C(OCC)C(=[N+]=[N-])CC(OCC)=C1N1CCOCC1 VWYSHPVBENQCRM-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
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- UIYIOASTUYGLAE-UHFFFAOYSA-N CCCOC(CC(C(OCCC)=C1)=[N+]=[N-])=C1N1CCOCC1.Cl Chemical compound CCCOC(CC(C(OCCC)=C1)=[N+]=[N-])=C1N1CCOCC1.Cl UIYIOASTUYGLAE-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 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
- 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
- 230000000996 additive effect Effects 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- YWLOOQUHDGZHNH-UHFFFAOYSA-L disodium;naphthalene-1,3-disulfonate Chemical compound [Na+].[Na+].C1=CC=CC2=CC(S(=O)(=O)[O-])=CC(S([O-])(=O)=O)=C21 YWLOOQUHDGZHNH-UHFFFAOYSA-L 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 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
- 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
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 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 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 |
|---|---|---|---|
| JP10200477A JPS5435723A (en) | 1977-08-25 | 1977-08-25 | Diazo copying method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10200477A JPS5435723A (en) | 1977-08-25 | 1977-08-25 | Diazo copying method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5435723A JPS5435723A (en) | 1979-03-16 |
| JPS6140978B2 true JPS6140978B2 (enrdf_load_stackoverflow) | 1986-09-12 |
Family
ID=14315631
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10200477A Granted JPS5435723A (en) | 1977-08-25 | 1977-08-25 | Diazo copying method |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5435723A (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 |
| JPS60132789A (ja) * | 1983-12-22 | 1985-07-15 | Ricoh Co Ltd | ジアゾ系感熱記録材料 |
-
1977
- 1977-08-25 JP JP10200477A patent/JPS5435723A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5435723A (en) | 1979-03-16 |
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