DE1230669B - Lichtempfindliche Diazoschicht - Google Patents
Lichtempfindliche DiazoschichtInfo
- Publication number
- DE1230669B DE1230669B DEK39385A DEK0039385A DE1230669B DE 1230669 B DE1230669 B DE 1230669B DE K39385 A DEK39385 A DE K39385A DE K0039385 A DEK0039385 A DE K0039385A DE 1230669 B DE1230669 B DE 1230669B
- Authority
- DE
- Germany
- Prior art keywords
- parts
- weight
- bis
- hydroxy
- dimethyl
- 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.)
- Pending
Links
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 9
- -1 N-substituted dibenzylamine Chemical class 0.000 claims description 17
- 150000008049 diazo compounds Chemical class 0.000 claims description 11
- 230000008878 coupling Effects 0.000 claims description 8
- 238000010168 coupling process Methods 0.000 claims description 8
- 238000005859 coupling reaction Methods 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 5
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 5
- 239000004327 boric acid Substances 0.000 description 5
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- XALSANSIWAVFDL-UHFFFAOYSA-N 2-[[ethyl-[(2-hydroxy-4,6-dimethylphenyl)methyl]amino]methyl]-3,5-dimethylphenol Chemical compound CC1=C(CN(CC2=C(C=C(C=C2O)C)C)CC)C(=CC(=C1)C)O XALSANSIWAVFDL-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 235000005074 zinc chloride Nutrition 0.000 description 3
- 239000011592 zinc chloride Substances 0.000 description 3
- NKTOLZVEWDHZMU-UHFFFAOYSA-N 2,5-xylenol Chemical compound CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 2
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 2
- NNPHFTYBYSTZIV-UHFFFAOYSA-N 2-[[(2-hydroxy-4,6-dimethylphenyl)methyl-methylamino]methyl]-3,5-dimethylphenol Chemical compound CC1=C(CN(CC2=C(C=C(C=C2O)C)C)C)C(=CC(=C1)C)O NNPHFTYBYSTZIV-UHFFFAOYSA-N 0.000 description 2
- XOUQAVYLRNOXDO-UHFFFAOYSA-N 2-tert-butyl-5-methylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1 XOUQAVYLRNOXDO-UHFFFAOYSA-N 0.000 description 2
- YCOXTKKNXUZSKD-UHFFFAOYSA-N 3,4-xylenol Chemical compound CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
- AXSQNZVCJBHIOP-UHFFFAOYSA-N CC1=C(CN(CC2=C(C=C(C(=C2)C)O)C)C)C=C(C(=C1)O)C Chemical compound CC1=C(CN(CC2=C(C=C(C(=C2)C)O)C)C)C=C(C(=C1)O)C AXSQNZVCJBHIOP-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
- 239000000987 azo dye Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- XTCHLXABLZQNNN-UHFFFAOYSA-N 3-ethyl-5-methylphenol Chemical compound CCC1=CC(C)=CC(O)=C1 XTCHLXABLZQNNN-UHFFFAOYSA-N 0.000 description 1
- USWINTIHFQKJTR-UHFFFAOYSA-N 3-hydroxynaphthalene-2,7-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(O)=CC2=C1 USWINTIHFQKJTR-UHFFFAOYSA-N 0.000 description 1
- ZDUIHRJGDMTBEX-UHFFFAOYSA-N 3-methyl-5-propan-2-ylphenol Chemical compound CC(C)C1=CC(C)=CC(O)=C1 ZDUIHRJGDMTBEX-UHFFFAOYSA-N 0.000 description 1
- SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 1
- 229940081735 acetylcellulose Drugs 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000006228 supernatant 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
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 (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL258888D NL258888A (enEXAMPLES) | 1959-12-09 | ||
| BE596995D BE596995A (enEXAMPLES) | 1959-12-09 | ||
| NL128748D NL128748C (enEXAMPLES) | 1959-12-09 | ||
| DEK39385A DE1230669B (de) | 1959-12-09 | 1959-12-09 | Lichtempfindliche Diazoschicht |
| CH1303660A CH385630A (de) | 1959-12-09 | 1960-11-21 | Lichtempfindliche Diazotypieschicht |
| GB41582/60A GB948965A (en) | 1959-12-09 | 1960-12-02 | Light-sensitive diazotype coatings |
| SE11885/60A SE306664B (enEXAMPLES) | 1959-12-09 | 1960-12-08 | |
| FR846458A FR1320008A (fr) | 1959-12-09 | 1960-12-09 | Couches photosensibles aux diazoïques |
| US268587A US3183093A (en) | 1959-12-09 | 1963-03-28 | Light sensitive diazotype material containing dibenzyl alkylamine coupling agents |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK39385A DE1230669B (de) | 1959-12-09 | 1959-12-09 | Lichtempfindliche Diazoschicht |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1230669B true DE1230669B (de) | 1966-12-15 |
Family
ID=7221692
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEK39385A Pending DE1230669B (de) | 1959-12-09 | 1959-12-09 | Lichtempfindliche Diazoschicht |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3183093A (enEXAMPLES) |
| BE (1) | BE596995A (enEXAMPLES) |
| CH (1) | CH385630A (enEXAMPLES) |
| DE (1) | DE1230669B (enEXAMPLES) |
| GB (1) | GB948965A (enEXAMPLES) |
| NL (2) | NL258888A (enEXAMPLES) |
| SE (1) | SE306664B (enEXAMPLES) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL120105C (enEXAMPLES) * | 1962-11-15 | |||
| US3499763A (en) * | 1967-05-01 | 1970-03-10 | Ibm | Bis phenols as high opacity diazotype couplers |
| US4790878A (en) * | 1987-01-20 | 1988-12-13 | Ford Motor Company | Corrosion inhibiting aqueous compositions comprising metal-chelating diphenolamine compounds |
| US4830680A (en) * | 1987-01-20 | 1989-05-16 | Ford Motor Company | Corrosion inhibiting aqueous compositions comprising metal-chelating diphenolamine compounds |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2650925A (en) * | 1948-05-03 | 1953-09-01 | Laaketehdas Orion Oy | N, n'-piperazine dicarbamate of 2, 4-di-hydroxyphenylthiol |
| DE1014432B (de) * | 1955-01-26 | 1957-08-22 | Kalle & Co Ag | Zweikomponentenmaterial fuer die Diazotypie |
| US2926193A (en) * | 1956-04-23 | 1960-02-23 | Dow Chemical Co | 4-chloro-alpha-dimethylamino-6-phenyl-o-cresol |
| US3064149A (en) * | 1957-02-01 | 1962-11-13 | Baermann Max | Controllable flux permanent magnet systems, especially for eddy current brakes or couplings for power propelled vehicles |
| NL97385C (enEXAMPLES) * | 1957-02-19 | |||
| BE576459A (enEXAMPLES) * | 1958-03-07 |
-
0
- NL NL128748D patent/NL128748C/xx active
- BE BE596995D patent/BE596995A/xx unknown
- NL NL258888D patent/NL258888A/xx unknown
-
1959
- 1959-12-09 DE DEK39385A patent/DE1230669B/de active Pending
-
1960
- 1960-11-21 CH CH1303660A patent/CH385630A/de unknown
- 1960-12-02 GB GB41582/60A patent/GB948965A/en not_active Expired
- 1960-12-08 SE SE11885/60A patent/SE306664B/xx unknown
-
1963
- 1963-03-28 US US268587A patent/US3183093A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| GB948965A (en) | 1964-02-05 |
| SE306664B (enEXAMPLES) | 1968-12-02 |
| NL258888A (enEXAMPLES) | |
| US3183093A (en) | 1965-05-11 |
| NL128748C (enEXAMPLES) | |
| BE596995A (enEXAMPLES) | |
| CH385630A (de) | 1964-12-15 |
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