US2037542A - Light sensitive materials containing light sensitive diazo compounds - Google Patents
Light sensitive materials containing light sensitive diazo compounds Download PDFInfo
- Publication number
- US2037542A US2037542A US710724A US71072434A US2037542A US 2037542 A US2037542 A US 2037542A US 710724 A US710724 A US 710724A US 71072434 A US71072434 A US 71072434A US 2037542 A US2037542 A US 2037542A
- Authority
- US
- United States
- Prior art keywords
- light sensitive
- diazo
- amino
- benzyl
- compounds
- 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 - Lifetime
Links
- 150000008049 diazo compounds Chemical class 0.000 title description 42
- 239000000463 material Substances 0.000 title description 12
- 150000001875 compounds Chemical class 0.000 description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 11
- 239000000243 solution Substances 0.000 description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 7
- 229960001553 phloroglucinol Drugs 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 150000004982 aromatic amines Chemical class 0.000 description 6
- 150000001555 benzenes Chemical class 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 230000008878 coupling Effects 0.000 description 6
- 238000010168 coupling process Methods 0.000 description 6
- 238000005859 coupling reaction Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- 229910021538 borax Inorganic materials 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 239000004328 sodium tetraborate Substances 0.000 description 4
- 235000010339 sodium tetraborate Nutrition 0.000 description 4
- 229910021653 sulphate ion Inorganic materials 0.000 description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
- SQMOOVFBFVTTGF-UHFFFAOYSA-N 1-benzyl-1-phenylhydrazine Chemical compound C=1C=CC=CC=1N(N)CC1=CC=CC=C1 SQMOOVFBFVTTGF-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- 239000012670 alkaline solution Substances 0.000 description 3
- 239000001164 aluminium sulphate Substances 0.000 description 3
- 235000011128 aluminium sulphate Nutrition 0.000 description 3
- -1 amino diazo compounds Chemical class 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 3
- 239000004327 boric acid Substances 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- BUACSMWVFUNQET-UHFFFAOYSA-H dialuminum;trisulfate;hydrate Chemical compound O.[Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O BUACSMWVFUNQET-UHFFFAOYSA-H 0.000 description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- XEMRAKSQROQPBR-UHFFFAOYSA-N (trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=CC=C1 XEMRAKSQROQPBR-UHFFFAOYSA-N 0.000 description 2
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- ZRDSGWXWQNSQAN-UHFFFAOYSA-N 6-diazo-n-phenylcyclohexa-2,4-dien-1-amine Chemical compound [N-]=[N+]=C1C=CC=CC1NC1=CC=CC=C1 ZRDSGWXWQNSQAN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000010421 pencil drawing Methods 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 229960001755 resorcinol Drugs 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000004513 sizing Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000001488 sodium phosphate Substances 0.000 description 2
- 229950000244 sulfanilic acid Drugs 0.000 description 2
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 2
- 235000019801 trisodium phosphate Nutrition 0.000 description 2
- 238000004383 yellowing Methods 0.000 description 2
- LSPMKHNOVLDBOX-UHFFFAOYSA-N 1-N-benzyl-1-N,2-dichlorobenzene-1,4-diamine Chemical compound NC1=CC(=C(N(CC2=CC=CC=C2)Cl)C=C1)Cl LSPMKHNOVLDBOX-UHFFFAOYSA-N 0.000 description 1
- YJKJAYFKPIUBAW-UHFFFAOYSA-N 9h-carbazol-1-amine Chemical compound N1C2=CC=CC=C2C2=C1C(N)=CC=C2 YJKJAYFKPIUBAW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 239000001166 ammonium sulphate Substances 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- YKYOUMDCQGMQQO-UHFFFAOYSA-L cadmium dichloride Chemical compound Cl[Cd]Cl YKYOUMDCQGMQQO-UHFFFAOYSA-L 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- VNEBWJSWMVTSHK-UHFFFAOYSA-L disodium;3-hydroxynaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(O)=CC2=C1 VNEBWJSWMVTSHK-UHFFFAOYSA-L 0.000 description 1
- ACIQMERAJKPQSD-UHFFFAOYSA-L disodium;acetate;chloride Chemical compound [Na+].[Na+].[Cl-].CC([O-])=O ACIQMERAJKPQSD-UHFFFAOYSA-L 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-N dithionous acid Chemical compound OS(=O)S(O)=O GRWZHXKQBITJKP-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- ATGUVEKSASEFFO-UHFFFAOYSA-N p-aminodiphenylamine Chemical compound C1=CC(N)=CC=C1NC1=CC=CC=C1 ATGUVEKSASEFFO-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride 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
- G03C1/54—Diazonium salts or diazo anhydrides
Definitions
- the present invention relates to light sensitive materials containing light sensitive diazo compounds.
- diazo compounds which contain at least one halogen atom in the ortho position to the OH: group of the benzyl residue are particularly useful.
- 1- diazo-Z'.4'-dichlorbenzyl-4-aniline and particularly also 1-diazo-2'.6'-dichlorbenzyl-4-aniline have proved very advantageous.
- the compounds may also contain in the aniline and benzyl residue further substituents such as alkyl, halogen, cyan and alkoxy or aryloxy groups, whereby small variations in the colour of the copies can be obtained.
- the diazo compounds used may be emother light sensitive more coloured diazo compound for colouring the layer more strongly whereby it is facilitated to distinguish the bleaching out of the layer during exposure.
- the compounds used according to the-invention offer the further advantage of possessing a greater degreeof light sensitiveness and a very high speed of coupling. .This latter property is of particular importance in practice, particularly for the so-called wet process, inasmuch as the necessary developing Naturalsolution only needs to be very slightly alkaline and in spite of this a rapid and complete coupling is obtained. In addition to this the destruction of the sizing of the paper is no longer to be feared.
- the diazo compounds can be prepared in the usual way.
- diazotized sulphanilic acid may be coupled with 2.6-dichlorbenzylaniline obtained by the condensation of dichlorbenzylchloride with aniline, in a strong acetic acid solution so as to form an azo dyestufl'.
- the dyestuff is then reduced by means of hydrosulphite and the resulting p-amino-dichlorbenzylaniline is diazotized in a strong hydrochloric acid solution.
- the diazo compound is there- Parts by weight upon separated preferably in the form of the zinc chloride double salt.
- Example 4 If the diazo compound set forth in Example 4 is replaced by 16 parts by weight of the sulphate of the diazo compound of 1-amino-2-chlor-4- [dichlorbenzyl (2',6' ,)l aminobenzene, prepared from 2.6 dichlorbenzylchloride and 4-amino-2- chloracetanilide with subsequent saponiflcation of the acetyl group and diazotation of the resulting compound, then extremely rapidly coupling paper is likewise obtained.
- the development is carried out by means of a developer as specified in Example 4' or by means of a developer which is still more weakly alkaline and which may be of approximately the following constitution:
- Light sensitive materials containing as light sensitive matter a diazotized benzyl-amino-phenylamine containing at least one halogen atom in the benzyl residue.
- R. is a phenyl residue which is substituted by halogen, an alkyl residue, an alkoxy group or a phenoxy group, and R a phenyl residue containing at least'one chlorine or bromine atom.
- Light sensitive material containing as light sensitive matter the diazo compound of l-amino- 3 phenoxy-4-(dichlor-z'fii-benzyl) amino-benzene yielding, after exposure, a diazotype with deep black or dull blue-gray shades, when developed with an alkaline solution of phloroglucine.
- Light sensitive material containing as light sensitive matter a diazotized benzyl-aminophenylamine containing at least one chlorine atom in the benzyl residue.
- Lightsensitive material containing as light I sensitive matter a diazotized benzyl-amino phenylamine containing at least one chlorine atom in the benzyl residue in the ortho-position to the CHz-group.
- Light sensitive material containing as light sensitive matter a diazotized benzyi-amino-arylamine containing at least one chlorine atom in the benzyl residue, said arylamine being. an arylamine of the benzene series.
- Light sensitive material containing as light sensitive matter a diazotized benzyl-aminoarylamine containing at least one chlorine atom in the benzyl residue in the ortho-positionto the cHr-group, said arylamine being an'arylamine of the benzene series.
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK0129120 | 1933-02-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2037542A true US2037542A (en) | 1936-04-14 |
Family
ID=7246781
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US710724A Expired - Lifetime US2037542A (en) | 1933-02-18 | 1934-02-10 | Light sensitive materials containing light sensitive diazo compounds |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US2037542A (en, 2012) |
| BE (1) | BE401394A (en, 2012) |
| FR (1) | FR768539A (en, 2012) |
| GB (1) | GB415081A (en, 2012) |
| NL (1) | NL36214C (en, 2012) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2537919A (en) * | 1948-05-05 | 1951-01-09 | Gen Aniline & Film Corp | Diazotype layer containing three coupling components for neutral black shades |
| US2542715A (en) * | 1945-07-16 | 1951-02-20 | Gen Aniline & Film Corp | Multicolor diazotype layers |
| US2542716A (en) * | 1945-07-16 | 1951-02-20 | Gen Aniline & Film Corp | Multicolor diazotype layers |
| US2616803A (en) * | 1948-03-11 | 1952-11-04 | Leonard E Ravich | Diazotype dyeing and printing of web or sheet material |
| US2657141A (en) * | 1947-07-14 | 1953-10-27 | Grinten Chem L V D | Diazotype developer composition containing a potassium borate and process of using same |
| US2659672A (en) * | 1948-01-09 | 1953-11-17 | Hall Harding Ltd | Diazotype photoprinting materials |
| US2792303A (en) * | 1951-09-19 | 1957-05-14 | Grinten Chem L V D | Process for the production of diazotype copies |
| US2970909A (en) * | 1957-02-04 | 1961-02-07 | Gen Aniline & Film Corp | Diazotype materials containing coupling components for high opacity ultraviolet yellows and visually dense sepias |
| US3169869A (en) * | 1958-06-04 | 1965-02-16 | Grinten Chem L V D | Diazotype material |
| US3261684A (en) * | 1961-08-31 | 1966-07-19 | Grinten Chem L V D | Process and developer for developing exposed one-component diazotype materials |
| US4132553A (en) * | 1977-03-24 | 1979-01-02 | Polychrome Corporation | Color proofing guide |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL218185A (en, 2012) * | 1957-06-17 |
-
0
- BE BE401394D patent/BE401394A/xx unknown
- NL NL36214D patent/NL36214C/xx active
-
1934
- 1934-02-10 US US710724A patent/US2037542A/en not_active Expired - Lifetime
- 1934-02-12 FR FR768539D patent/FR768539A/fr not_active Expired
- 1934-02-16 GB GB5254/34A patent/GB415081A/en not_active Expired
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2542715A (en) * | 1945-07-16 | 1951-02-20 | Gen Aniline & Film Corp | Multicolor diazotype layers |
| US2542716A (en) * | 1945-07-16 | 1951-02-20 | Gen Aniline & Film Corp | Multicolor diazotype layers |
| US2657141A (en) * | 1947-07-14 | 1953-10-27 | Grinten Chem L V D | Diazotype developer composition containing a potassium borate and process of using same |
| US2659672A (en) * | 1948-01-09 | 1953-11-17 | Hall Harding Ltd | Diazotype photoprinting materials |
| US2616803A (en) * | 1948-03-11 | 1952-11-04 | Leonard E Ravich | Diazotype dyeing and printing of web or sheet material |
| US2537919A (en) * | 1948-05-05 | 1951-01-09 | Gen Aniline & Film Corp | Diazotype layer containing three coupling components for neutral black shades |
| US2792303A (en) * | 1951-09-19 | 1957-05-14 | Grinten Chem L V D | Process for the production of diazotype copies |
| US2970909A (en) * | 1957-02-04 | 1961-02-07 | Gen Aniline & Film Corp | Diazotype materials containing coupling components for high opacity ultraviolet yellows and visually dense sepias |
| US3169869A (en) * | 1958-06-04 | 1965-02-16 | Grinten Chem L V D | Diazotype material |
| US3261684A (en) * | 1961-08-31 | 1966-07-19 | Grinten Chem L V D | Process and developer for developing exposed one-component diazotype materials |
| US4132553A (en) * | 1977-03-24 | 1979-01-02 | Polychrome Corporation | Color proofing guide |
Also Published As
| Publication number | Publication date |
|---|---|
| FR768539A (fr) | 1934-08-07 |
| NL36214C (en, 2012) | |
| BE401394A (en, 2012) | |
| GB415081A (en) | 1934-08-16 |
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