US2197456A - Light-sensitive material - Google Patents
Light-sensitive material Download PDFInfo
- Publication number
- US2197456A US2197456A US224732A US22473238A US2197456A US 2197456 A US2197456 A US 2197456A US 224732 A US224732 A US 224732A US 22473238 A US22473238 A US 22473238A US 2197456 A US2197456 A US 2197456A
- Authority
- US
- United States
- Prior art keywords
- diazo
- light
- sulphonate
- sulphonates
- groups
- 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
- 239000000463 material Substances 0.000 title description 6
- -1 aliphatic alcohols Chemical class 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 16
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 11
- 125000003277 amino group Chemical group 0.000 description 9
- 230000008878 coupling Effects 0.000 description 9
- 238000010168 coupling process Methods 0.000 description 9
- 238000005859 coupling reaction Methods 0.000 description 9
- 150000001555 benzenes Chemical class 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 7
- 159000000000 sodium salts Chemical class 0.000 description 7
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 150000008049 diazo compounds Chemical class 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 5
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 4
- 239000000084 colloidal system Substances 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 3
- 229960001553 phloroglucinol Drugs 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 235000010265 sodium sulphite Nutrition 0.000 description 3
- 244000215068 Acacia senegal Species 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-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
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 150000001728 carbonyl compounds Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000006266 etherification reaction Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- NUMXHEUHHRTBQT-AATRIKPKSA-N 2,4-dimethoxy-1-[(e)-2-nitroethenyl]benzene Chemical class COC1=CC=C(\C=C\[N+]([O-])=O)C(OC)=C1 NUMXHEUHHRTBQT-AATRIKPKSA-N 0.000 description 1
- 241000790917 Dioxys <bee> Species 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-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
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 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
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000006203 ethylation Effects 0.000 description 1
- 238000006200 ethylation reaction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 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
- 150000002989 phenols Chemical class 0.000 description 1
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- G03C1/56—Diazo sulfonates
Definitions
- the invention relates to light-sensitive materials.
- light-sensitive layers suitable for producing negative diazotype copies can be obtained if there are used as lightsensitive compounds, diazo sulphonates which contain in the nucleus, carrying the diazo sulphonate group, two etherified oxy groups but no amino groups or substituted amino groups.
- the compounds may also contain more than two etherified oxy groups, for example three oxy groups, although it is chiefly the compounds with only two etherified oxy groups which have practical importance.
- the etherification is preferably carried out by low molecular aliphatic alcohols with few carbon atoms, such as methyl 2:; alcohol or ethyl alcohol, as in the presence of high molecular ether residues the solubility of the diazo sulphonates in water decreases.
- the diazo sulphonates should be easily soluble in water.
- the etherification can, however, also take place by means of phenols so far as the diazo sulphonates obtained still show the necessary solubility in water.
- compounds are preferably used which are derived from hydroquinone. It is, however, also possible to use diazo sulphonates which are derived from other aromatic dioxy or polyoxy compounds, particularly those of the benzene series, so long as they are free from amino groups.
- diazo sulphonates which are derived from other aromatic dioxy or polyoxy compounds, particularly those of the benzene series, so long as they are free from amino groups.
- resorcindiether-diazo sulphonates come into question, for example, ethers of 2.4-dioxybenzene-l-diazo sulphonate.
- pyrocatechin-diether-diazo s5 sulphonates are suitable, for example ethers of the 3.4-dioxybenzene-1-diazo sulphonate.
- the position of the diazo sulphonate group or of the two alkoxy groups with respect to each other is preferably such that two but not more than two of the three 5 said groups are adjacent each other.
- the trialkoxy compounds the 2.4.5-trialkoxy-Ldiazo sulphonates are particularly suitable.
- the compounds used according to the invention can also be substituted by other substituents 10 of the kind which are also generally used in normal diazo-type copying.
- substituents 10 which are also generally used in normal diazo-type copying.
- the image dyes produced should preferably be insoluble in water so that the fixing of the pictures can be effected in the usual manner by washing out, substitu- 1 ents which increase the solubility in water to a great extent, such as sulpho groups, are in general unsuitable. It is necessary, as is known, to combine sufilcient water-solubility of the diazosulphonates with water-insolubility of the dye- 20 stuffs produced with the diazo sulphonates.
- alkyls such as methyland 25 ethyl, act favorably as substituents, particularly with regard to the depth of color of the dyes produced with the diazo sulphonates.
- the alkyls should not contain more than four carbon atoms.
- aryls or cyclo- 80 hexyl are suitable as substituents so long as the substituted compounds are still sumciently soluble in water.
- the diazo sulphonates used according to the invention are distinguished by the fact that with the use of the normal azo components, they generally lead to dyes with dark tones, so that the production of easily legible copies is facilitated. Moreover, they are very stable. The printing materials produced with the diazo sulphonates are, therefore, 'very stable.
- the dyes obtained are, in general, resistant to water while the diazo sulphonates themselves have a good solubility in water, so that the copies produced with the new light-sensitive layers can be quickly and easily fixed in the known manner by soaking.
- the coupling intensity of the diazo sulphonates can be considerably increased in the'hnown manner by the addition of carbonyl compounds to the light-sensitive layers.
- carbonyl compounds for example pyroracemic acid
- aliphatic ketonic acids for example pyroracemic acid
- the latter compound acts still more favorably in that it makes possible the production of copies with particularly clear grounds.
- a light grey dyeing sometimes'occurs if the materials are stored for a long time.
- An increase in the coupling intensity can, moreover, be produced by the presence of thiourea or its derivatives in the light-sensitive layer.
- This compound is nitrated in glacial acetic acid whereafter the 2.5-diethoxy-l-chloro-4-nitrobenzene obtained is reduced in the usual manner, for example with iron and hydrochloric acid to 2.5- diethoxy-l-chloro-4-amino-benzene.
- This compound is then diazotized in the usual manner in a hydrochloric solution.
- the diazo compound separated out 'as zinc chloride double salt is converted into the diazo sulphonate by means of sodium sulphite.
- gum arabic are dissolved in 100 c. c. of water. with layers which are produced with the help of this preparatiomthere are obtained from well graded photographic negatives dark blue-violet positive copies rich in detail.
- the production of i the sodium salt of 2-.5-diethoxy-4-methyl-ben zene-diazo-sulphonic acid is eflected by the ethylation of 2.5-dioxytoluene with soda lye and diethyl sulphate, nitration of thefifi-dl h ene obtained, reduction, diazotisation and double 10 -decomposition with sodium sulphite.
- the sodium salt of 2.4.5- triethoxy-benzene-diazo-sulphonic acid can also be used.
- sufliciently easily soluble salts of the said diazo sulphonlc acid may be 15 used, for example the potassium or ammonium salt.
- the triethoxy compound the corresponding trimethoxy compound can also be used.
- Paper is coated with a solution of 6 grams of the sodium salt of 2.4-diethoxy-5-chlorobenzene diazo sulphonic acid, 3 grams of phloroglucine and 4 grams of sodium pyroracemate. With this material brown copies are obtained; as the gradation is fairly flat. If copies rich in hard contrasts are required a cellulose hydrate sheet is placed between the original and copying layer during copying which sheet has been saturated with a solution of .5 gram of the diazo compound 30 of para-aminodiphenylamine and 1.5 grams of tartaric acid in 100 c. c. of water.
- the gradation of the pictures may be made as steep as desired, while the exposure 35 period is lengthened correspondingly. Good results are also obtained if instead of the said diazo sulphonate the 2-chloro-4.5-dimethoxybenzenediazo-sulphonate is used.
- Light-sensitive layer comprising a coupling component and a diazo sulphonate which carries in the nucleus containing the diazo sulphonate group at least two etherified oxy groups and no amino group.
- Light-sensitive layer according to claim 1 characterised in that the said diazo sulphonate belongs to the benzene series.
- Light-sensitive layer comprising a coupling component and a diazo sulphonate of the ben- 5 .zene series which carries in the benzene nucleus containing the diazo sulphonate group at least two alkoxy groups but no amino group.
- Light-sensitive layer according to claim 3 characterised in that the said alkoxy groups con- 55 tain at most two carbon atoms.
- Light-sensitive layer comprising a coupling component and a diazo sulphonate of the benzene series which carries in the benzene nucleus containing the diazo sulphonate group at least two ethoxy groups but no amino group.
- Light-sensitive layer comprising a coupling component and a diazo sulphonate of the benzene series which carries in the benzene nucleus containing the diazo sulphonate group two alkoxy groups but no amino group, the diazo sulphonate group and the two alkoxy groups being positioned with regard to each other in such a way that two but not more than two of the said three groups are adjacent each other.
- Light-sensitive layer comprising a coupling component and a diazo sulphonate of the following general formula:
- R stands for a benzene nucleus
- R1 and R2 for alkyl groups
- Y for a diazo sulphonate group
- Z is a member of the group consisting of hydrogen, chlorine, bromine and alkyl.
- Light-sensitive layer according to claim 8 wherein two but not more than two of the three groups, R1O-, RzO- and Y are ortho to each other in the nucleus R.
- Light-sensitive layer comprising a. coupling component and a diazo sulphonate of the following general formula:
- R1 and R2 stand for alkyl groups
- Y for a diazo sulphonate group
- Z is a member of the group consisting of hydrogen, chlorine, bromine and alkyl.
- Light-sensitive layer comprising a coupling component and a diazo sulphonate of the following general formula:
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)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Color Printing (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE206748X | 1937-08-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2197456A true US2197456A (en) | 1940-04-16 |
Family
ID=5793315
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US224732A Expired - Lifetime US2197456A (en) | 1937-08-20 | 1938-08-13 | Light-sensitive material |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US2197456A (de) |
| CH (1) | CH206748A (de) |
| GB (2) | GB518129A (de) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2613149A (en) * | 1947-10-29 | 1952-10-07 | Gen Aniline & Film Corp | Diazotype photoprinting material |
| US2720467A (en) * | 1951-09-11 | 1955-10-11 | Ozalid Co Ltd | Process for preparing photographic elements |
| US2822271A (en) * | 1953-10-19 | 1958-02-04 | Keuffel & Esser Co | Photosensitive material |
| US2854338A (en) * | 1955-03-18 | 1958-09-30 | Gen Aniline & Film Corp | Negative working diazo sulfonate foils |
| US3607287A (en) * | 1968-12-30 | 1971-09-21 | Keuffel & Esser Co | Negative-working two-component diazosulfonate material |
| US3713825A (en) * | 1970-04-27 | 1973-01-30 | Plastic Coating Corp | Light-activated diazography |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3408234A (en) * | 1966-10-24 | 1968-10-29 | Phillips Petroleum Co | Adjustable jacket for storage batteries |
-
1938
- 1938-07-29 CH CH206748D patent/CH206748A/de unknown
- 1938-08-13 US US224732A patent/US2197456A/en not_active Expired - Lifetime
- 1938-08-15 GB GB24046/38A patent/GB518129A/en not_active Expired
- 1938-08-15 GB GB10010/39A patent/GB518162A/en not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2613149A (en) * | 1947-10-29 | 1952-10-07 | Gen Aniline & Film Corp | Diazotype photoprinting material |
| US2720467A (en) * | 1951-09-11 | 1955-10-11 | Ozalid Co Ltd | Process for preparing photographic elements |
| US2822271A (en) * | 1953-10-19 | 1958-02-04 | Keuffel & Esser Co | Photosensitive material |
| US2854338A (en) * | 1955-03-18 | 1958-09-30 | Gen Aniline & Film Corp | Negative working diazo sulfonate foils |
| US3607287A (en) * | 1968-12-30 | 1971-09-21 | Keuffel & Esser Co | Negative-working two-component diazosulfonate material |
| US3713825A (en) * | 1970-04-27 | 1973-01-30 | Plastic Coating Corp | Light-activated diazography |
Also Published As
| Publication number | Publication date |
|---|---|
| CH206748A (de) | 1939-08-31 |
| GB518162A (en) | 1940-02-19 |
| GB518129A (en) | 1940-02-19 |
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