DE1772980B2 - Mehrkomponenten-Diazotypiematerial - Google Patents
Mehrkomponenten-DiazotypiematerialInfo
- Publication number
- DE1772980B2 DE1772980B2 DE1772980A DE1772980A DE1772980B2 DE 1772980 B2 DE1772980 B2 DE 1772980B2 DE 1772980 A DE1772980 A DE 1772980A DE 1772980 A DE1772980 A DE 1772980A DE 1772980 B2 DE1772980 B2 DE 1772980B2
- Authority
- DE
- Germany
- Prior art keywords
- coupling component
- hydroxy
- component
- naphthamide
- yellow
- 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
- 239000000463 material Substances 0.000 title claims description 47
- 230000008878 coupling Effects 0.000 claims description 50
- 238000010168 coupling process Methods 0.000 claims description 50
- 238000005859 coupling reaction Methods 0.000 claims description 50
- 239000012954 diazonium Substances 0.000 claims description 26
- 150000001989 diazonium salts Chemical class 0.000 claims description 26
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 19
- -1 5-chlorophenyl Chemical group 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 10
- AQYMRQUYPFCXDM-UHFFFAOYSA-N 3-hydroxy-n-(2-methoxyphenyl)naphthalene-2-carboxamide Chemical compound COC1=CC=CC=C1NC(=O)C1=CC2=CC=CC=C2C=C1O AQYMRQUYPFCXDM-UHFFFAOYSA-N 0.000 claims description 5
- RMHJJUOPOWPRBP-UHFFFAOYSA-N naphthalene-1-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=CC=CC2=C1 RMHJJUOPOWPRBP-UHFFFAOYSA-N 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 3
- RGCITEKHKXPDDH-UHFFFAOYSA-N 4-(diethylamino)benzenediazonium Chemical compound CCN(CC)C1=CC=C([N+]#N)C=C1 RGCITEKHKXPDDH-UHFFFAOYSA-N 0.000 claims description 2
- FHQRDEDZJIFJAL-UHFFFAOYSA-N 4-phenylmorpholine Chemical compound C1COCCN1C1=CC=CC=C1 FHQRDEDZJIFJAL-UHFFFAOYSA-N 0.000 claims description 2
- HTVPAACTHAQQAS-UHFFFAOYSA-N n-(2-hydroxy-4-methylphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(C)C=C1O HTVPAACTHAQQAS-UHFFFAOYSA-N 0.000 claims description 2
- XDWATWCCUTYUDE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-hydroxynaphthalene-2-carboxamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=O)C1=CC2=CC=CC=C2C=C1O XDWATWCCUTYUDE-UHFFFAOYSA-N 0.000 claims description 2
- ZTXWIKHKNGFJAX-UHFFFAOYSA-N 1-hydroxynaphthalene-2-carboxamide Chemical compound C1=CC=CC2=C(O)C(C(=O)N)=CC=C21 ZTXWIKHKNGFJAX-UHFFFAOYSA-N 0.000 claims 1
- CIZVQWNPBGYCGK-UHFFFAOYSA-N benzenediazonium Chemical class N#[N+]C1=CC=CC=C1 CIZVQWNPBGYCGK-UHFFFAOYSA-N 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 239000010410 layer Substances 0.000 description 14
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000011877 solvent mixture Substances 0.000 description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
- YCPXWRQRBFJBPZ-UHFFFAOYSA-N 5-sulfosalicylic acid Chemical compound OC(=O)C1=CC(S(O)(=O)=O)=CC=C1O YCPXWRQRBFJBPZ-UHFFFAOYSA-N 0.000 description 5
- 150000001450 anions Chemical class 0.000 description 5
- 239000011230 binding agent Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 230000033458 reproduction Effects 0.000 description 5
- 229910052709 silver Inorganic materials 0.000 description 5
- 239000004332 silver Substances 0.000 description 5
- 229920002301 cellulose acetate Polymers 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 235000005074 zinc chloride Nutrition 0.000 description 3
- 239000011592 zinc chloride Substances 0.000 description 3
- PHXLONCQBNATSL-UHFFFAOYSA-N 2-[[2-hydroxy-5-methyl-3-(1-methylcyclohexyl)phenyl]methyl]-4-methyl-6-(1-methylcyclohexyl)phenol Chemical compound OC=1C(C2(C)CCCCC2)=CC(C)=CC=1CC(C=1O)=CC(C)=CC=1C1(C)CCCCC1 PHXLONCQBNATSL-UHFFFAOYSA-N 0.000 description 2
- ZLVFYUORUHNMBO-UHFFFAOYSA-N 4-bromo-2,6-dimethylphenol Chemical compound CC1=CC(Br)=CC(C)=C1O ZLVFYUORUHNMBO-UHFFFAOYSA-N 0.000 description 2
- NJYDJNRTEZIUBS-UHFFFAOYSA-N 4-morpholin-4-ylbenzenediazonium Chemical compound C1=CC([N+]#N)=CC=C1N1CCOCC1 NJYDJNRTEZIUBS-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000001045 blue dye Substances 0.000 description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Substances SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 2
- VOLGAXAGEUPBDM-UHFFFAOYSA-N $l^{1}-oxidanylethane Chemical compound CC[O] VOLGAXAGEUPBDM-UHFFFAOYSA-N 0.000 description 1
- HRWJUSVKPYSOSI-UHFFFAOYSA-N 2,5-diethoxy-4-morpholin-4-ylbenzenediazonium Chemical compound C1=C([N+]#N)C(OCC)=CC(N2CCOCC2)=C1OCC HRWJUSVKPYSOSI-UHFFFAOYSA-N 0.000 description 1
- 125000003341 7 membered heterocyclic group Chemical group 0.000 description 1
- IRVXJSBATNRECV-UHFFFAOYSA-N 7-tert-butyl-2,2-dimethyl-4-propan-2-yl-3,4-dihydrochromen-6-ol Chemical compound CC(C)(C)C1=C(O)C=C2C(C(C)C)CC(C)(C)OC2=C1 IRVXJSBATNRECV-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- CIPVVROJHKLHJI-UHFFFAOYSA-N n,n-diethyl-3-methylaniline Chemical compound CCN(CC)C1=CC=CC(C)=C1 CIPVVROJHKLHJI-UHFFFAOYSA-N 0.000 description 1
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
- JRNGUTKWMSBIBF-UHFFFAOYSA-N naphthalene-2,3-diol Chemical compound C1=CC=C2C=C(O)C(O)=CC2=C1 JRNGUTKWMSBIBF-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000001043 yellow dye Substances 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S534/00—Organic compounds -- part of the class 532-570 series
- Y10S534/01—Mixtures of azo compounds
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)
- Heat Sensitive Colour Forming Recording (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US65707767A | 1967-07-31 | 1967-07-31 | |
| US7423070A | 1970-09-21 | 1970-09-21 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1772980A1 DE1772980A1 (de) | 1971-11-25 |
| DE1772980B2 true DE1772980B2 (de) | 1974-06-20 |
| DE1772980C3 DE1772980C3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-02-06 |
Family
ID=26755394
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1772980A Granted DE1772980B2 (de) | 1967-07-31 | 1968-07-30 | Mehrkomponenten-Diazotypiematerial |
Country Status (5)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL165568C (nl) * | 1970-05-13 | 1981-04-15 | Oce Van Der Grinten Nv | Twee componenten diazotypmateriaal. |
| US3765895A (en) * | 1971-11-22 | 1973-10-16 | Eastman Kodak Co | Photographic print-out composition containing a colorless stable-free radical precursor and a photoactivator |
| US4054456A (en) * | 1972-04-21 | 1977-10-18 | Fuji Photo Film Co., Ltd. | Diazo photographic materials containing 2-hydroxy 3-naphthanilide coupler |
| US3836369A (en) * | 1972-09-05 | 1974-09-17 | Du Pont | Diazo photosensitive composition |
| DE2746551A1 (de) * | 1977-10-17 | 1979-04-26 | Hoechst Ag | Diazotypiematerial |
| AU3665199A (en) * | 1998-04-29 | 1999-11-16 | Vertex Pharmaceuticals Incorporated | Inhibitors of impdh enzyme |
| US6653309B1 (en) | 1999-04-26 | 2003-11-25 | Vertex Pharmaceuticals Incorporated | Inhibitors of IMPDH enzyme technical field of the invention |
-
1967
- 1967-07-31 US US657077A patent/US3573051A/en not_active Expired - Lifetime
-
1968
- 1968-07-25 GB GB1231269D patent/GB1231269A/en not_active Expired
- 1968-07-30 FR FR1584606D patent/FR1584606A/fr not_active Expired
- 1968-07-30 BE BE718809D patent/BE718809A/xx unknown
- 1968-07-30 DE DE1772980A patent/DE1772980B2/de active Granted
-
1970
- 1970-09-21 US US74230A patent/US3679413A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US3679413A (en) | 1972-07-25 |
| DE1772980C3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-02-06 |
| DE1772980A1 (de) | 1971-11-25 |
| US3573051A (en) | 1971-03-30 |
| FR1584606A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1969-12-26 |
| GB1231269A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-05-12 |
| BE718809A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1968-12-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |