US2494906A - Cyan component for diazotype color process - Google Patents
Cyan component for diazotype color process Download PDFInfo
- Publication number
- US2494906A US2494906A US753036A US75303647A US2494906A US 2494906 A US2494906 A US 2494906A US 753036 A US753036 A US 753036A US 75303647 A US75303647 A US 75303647A US 2494906 A US2494906 A US 2494906A
- Authority
- US
- United States
- Prior art keywords
- diazotype
- cyan
- color process
- naphthalene
- acid
- 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
- 238000000034 method Methods 0.000 title claims description 12
- -1 AMINO GROUPS Chemical group 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 6
- 150000008049 diazo compounds Chemical class 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- ADQAFJJAAZDWCY-UHFFFAOYSA-N 4-ethoxy-1-n,1-n-diethylbenzene-1,3-diamine Chemical compound CCOC1=CC=C(N(CC)CC)C=C1N ADQAFJJAAZDWCY-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 230000001235 sensitizing effect Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 235000005074 zinc chloride Nutrition 0.000 description 3
- 239000011592 zinc chloride Substances 0.000 description 3
- NKJAYTHAELPXCQ-UHFFFAOYSA-N 8-amino-1-hydroxy-2h-naphthalene-1-sulfonic acid Chemical class C1=CCC(O)(S(O)(=O)=O)C2=C1C=CC=C2N NKJAYTHAELPXCQ-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 241000974482 Aricia saepiolus Species 0.000 description 2
- 125000004442 acylamino group Chemical group 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 125000001769 aryl amino group Chemical group 0.000 description 2
- 238000006149 azo coupling reaction Methods 0.000 description 2
- YKYOUMDCQGMQQO-UHFFFAOYSA-L cadmium dichloride Chemical compound Cl[Cd]Cl YKYOUMDCQGMQQO-UHFFFAOYSA-L 0.000 description 2
- 229920002301 cellulose acetate Polymers 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- OGNVQLDIPUXYDH-ZPKKHLQPSA-N (2R,3R,4S)-3-(2-methylpropanoylamino)-4-(4-phenyltriazol-1-yl)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid Chemical compound CC(C)C(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)OC(C(O)=O)=C[C@@H]1N1N=NC(C=2C=CC=CC=2)=C1 OGNVQLDIPUXYDH-ZPKKHLQPSA-N 0.000 description 1
- OGSZAQASQUXQOD-UHFFFAOYSA-N 2,3-dihydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(O)(=O)=O)=C(O)C(O)=CC2=C1 OGSZAQASQUXQOD-UHFFFAOYSA-N 0.000 description 1
- YGNDWDUEMICDLW-UHFFFAOYSA-N 7-anilino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C=1C=C2C(O)=CC(S(O)(=O)=O)=CC2=CC=1NC1=CC=CC=C1 YGNDWDUEMICDLW-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- OODCFCAUIVIKTC-UHFFFAOYSA-N CNC1=CC=CC2=CC=CC(=C12)O Chemical compound CNC1=CC=CC2=CC=CC(=C12)O OODCFCAUIVIKTC-UHFFFAOYSA-N 0.000 description 1
- 229920008347 Cellulose acetate propionate Polymers 0.000 description 1
- DQEFEBPAPFSJLV-UHFFFAOYSA-N Cellulose propionate Chemical compound CCC(=O)OCC1OC(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C1OC1C(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C(COC(=O)CC)O1 DQEFEBPAPFSJLV-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000005228 aryl sulfonate group Chemical group 0.000 description 1
- 238000006254 arylation reaction Methods 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229920006218 cellulose propionate Polymers 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000004989 p-phenylenediamines Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 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
Definitions
- the present invention relates to sensitized diazotype materials'for the diazotype color process which when exposed through a cyan separation positive and developed yield greenish blue images of high intensity.
- the diazotype process be utilized for the purpose of manufacturing natural color prints.
- the method suggested involved printing separation positives in the primary colors on separate transparent plastic film layers, dryedeveloping the layers and transposing the layers in register to produce a color print.
- R is hydroxyl, amino, acylamino, such as, acetylamino, propionylamino, butyrylamino, benzoylamino, and the like, alkylamino, such as,
- acyl derivatives mentioned above may be prepared by treatment of the 1-hydroxy-8-amino-naphthalene sulfonic acids with the anhydrides of the acids involved just as in the preparation of, for instance, acetyl J acid;
- the l-hydroXy-B-amino-naphthalene sulfonic acids in which the amino groupie substituted by alkyl or aryl may be prepared by alkylation and arylation, just as in the preparation of, for instance, dimethyl-2-amino-8-naphthol 6-su1fonic acid or of phenyl J acid.
- diazos which we have found to yield excellent results are those derived from the following compounds:
- p-amino-N-diethyl-o-toluidine 4-diethylamino-o-phenetidine p- (N-ethyl-N-hydroxyethylamino) -o-to1uidine water or mixtures of water and a low molecular weight alcohol, 1. e., methyl alcohol, ethyl alcohol, and the like.
- the base to which the sensitizing compositions are applied may be a sheet, film, or the like, of any transparent film-forming material preferably a cellulose ester, such as, cellulose acetate, cellulose propionate, cellulose acetate propionate, and the like.
- a cellulose ester such as, cellulose acetate, cellulose propionate, cellulose acetate propionate, and the like.
- the sensitized base is utilized in the manner outlined above, that is, by exposure under a desired cyan separation positive by U. V. light and development by ammonia fumes.
- Emample I A cellulose acetate film is coated with a solution of the following components:
- Example II Example III The procedure is the same as in Example I excepting that 1-hydroxy-8-acetylamino-naph- 55 thalene-4- sulf'onic acid is substituted for the dihydroxy-naphthalene sulfonic acid.
- the processing of the resulting film leads to greenish-blue positives of high density.
- R is a member selected from the class consisting of hydroxyl, amino, acylamino, alkylamino, and arylamino.
- the light sensitive diazo compound is the zinc chloride double salt of the diazo from 4-diethylaminoo-phenetidine and the azo coupling component is 1.8-dihydroxy-naphthalene-4-sulfonic acid.
- the process of producing cyan diazotype prints capable of transmitting both green and blue light comprises sensitizing a transparent base with a composition containing as a light sensitive diazo compound a diazotized p-phenylene-diamine in which one of the amino groups is di-substituted by members selected from the class consisting of alkyl and hydroxyalkyl and as a coupling component a compound of the following 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)
- Color Printing (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
Description
Patented Jan. 17,1950
'ATENT. .OFFICE CYAN COMPONENT FOR DIAZOTYPE COLOR PROCESS seal 6. siiikin and Thaddeus a. Trojnar, Binghamton, N. Y., assignors to General Aniline & Film Corporation, New York, N. 'Y., a corporation of Delaware No. Drawing. Application June 6, 194 7,
. Serial No. 753,036
4 Claims.
The present invention relates to sensitized diazotype materials'for the diazotype color process which when exposed through a cyan separation positive and developed yield greenish blue images of high intensity.
It has been suggested that the diazotype process be utilized for the purpose of manufacturing natural color prints. The method suggested involved printing separation positives in the primary colors on separate transparent plastic film layers, dryedeveloping the layers and transposing the layers in register to produce a color print.
This process, howeven'was found to be unsatisfactory primarily because the sensitized compositions used for producing the cyan records yielded images too blue in color. Inasmuch as the cyan record is the key image record just as in color photography the decided blue nature of this record led to color distortion. This phenomenon which also manifests itself in three-color photography as may be seen from Frohlich et al. U. S. Patent No. 2,357,394; militated against the adoption of the aforementioned process despite the simplicity inherent therein.
We have now discovered that the objections referred to above can be completely avoided and cyan records blue-green in color and of high intensity can beobtained if there can be used as A the coupling component for the layer in which the cyan separation is to be recorded a l-hydroxy-naphthalene sulfonic acid containing in the 8-position a hydroxyl group or an aminoor substituted amino group. The employment of such coupling components in the sensitizingcompositions used to produce the cyan records in the diazotype color process and the processing of carriers bearing such com-positions constitute the purposes and. objects of thepresent invention.
The coupling components contemplated herein are typified by the following structural formula:
R OH
SOBH
in which R is hydroxyl, amino, acylamino, such as, acetylamino, propionylamino, butyrylamino, benzoylamino, and the like, alkylamino, such as,
2 methylamino, dimethylamino, ethylamino, diethylamino, and the like, or arylamino, such as, phenylamino, di-phenylamino, and the like.
Examples of compounds embraced by this formula and which we have found to be satisfactory for our purposes are:
acid acid acid 1 ydroxy n q qn e fl naphthalene i sulfonic acid ,1 hydroxy 3 benaoylamino naphthalene 'lsulfonic acid 1 hydroxy 8 methylamino naphthalene 5- sul-fonic acid 1 hydroxy 8 dimethylethylamino e naphthalene-G-sulfonic acid 1 hydroxy 8 butyrylamino naphthalene 5 sulfonic acid 1 hydroxy 8 phenylamino naphthalene 4- sulfonic acid The 1.S-dihydroxy-naphthalene sulfonic acids and the 1-hydroxy-8-aminonaphthalene sulfonic acids are well known compounds. The acyl derivatives mentioned above may be prepared by treatment of the 1-hydroxy-8-amino-naphthalene sulfonic acids with the anhydrides of the acids involved just as in the preparation of, for instance, acetyl J acid; Generally, the l-hydroXy-B-amino-naphthalene sulfonic acids in which the amino groupie substituted by alkyl or aryl may be prepared by alkylation and arylation, just as in the preparation of, for instance, dimethyl-2-amino-8-naphthol 6-su1fonic acid or of phenyl J acid.
The diazo component which is utilized in the sensitizing composition may be any of those generally employed in the diazo-type art although we prefer the N=substituted p-phenylenediamines. While the diazos are preferably employed in the form of the zinc chloride double salts they may likewise be utilized as such or in the form of their double salts with cadmium chloride, tin chloride or the like, or in the form of the fiuoro-borates or the alkyl or aryl sulfonates, such as, the methyl, ethyl, propyl, phenyl and the like sulfonates.
Examples of diazos which we have found to yield excellent results are those derived from the following compounds:
p-amino-N-diethyl-o-toluidine 4-diethylamino-o-phenetidine p- (N-ethyl-N-hydroxyethylamino) -o-to1uidine water or mixtures of water and a low molecular weight alcohol, 1. e., methyl alcohol, ethyl alcohol, and the like.
The base to which the sensitizing compositions are applied may be a sheet, film, or the like, of any transparent film-forming material preferably a cellulose ester, such as, cellulose acetate, cellulose propionate, cellulose acetate propionate, and the like.
The sensitized base is utilized in the manner outlined above, that is, by exposure under a desired cyan separation positive by U. V. light and development by ammonia fumes.
The following examples serve to illustrate the invention but it is to be understood that the invention is not restricted thereto:
Emample I A cellulose acetate film is coated with a solution of the following components:
Water 50 Alcohol 50 Citric acid grams Thiourea do 2 1.8-dihydroxy-naphthalene-4-sulfonic acid grams 2 The zinc chloride double salt of the diazo from 4-diethylamino-o-phenetidine grams 4 When dried and exposed to U. V. light under a selected cyan separation positive and developed in the usual way with ammonia vapor, a greenishblue positive reproduction of high density is obtained.
Example II Example III The procedure is the same as in Example I excepting that 1-hydroxy-8-acetylamino-naph- 55 thalene-4- sulf'onic acid is substituted for the dihydroxy-naphthalene sulfonic acid. Here again, the processing of the resulting film leads to greenish-blue positives of high density.
We claim:
1. Light sensitive diazotype material for use in producing a cyan record in the diazotype color process comprising a transparent base carrying as a light sensitive diazo compound a diazotized p-phenylene-diamine in which one of the amino groups is di-substituted by members selected from the class consisting of alkyl and hydroxyalkyl and as the azo component a compound of the following formula:
R OH
wherein R is a member selected from the class consisting of hydroxyl, amino, acylamino, alkylamino, and arylamino.
2. The article as defined in claim 1 in which the azo coupling component is 1.8-dihydroxynaphthalene-4-sulfonic acid.
3. The article as defined in claim 1 wherein the light sensitive diazo compound is the zinc chloride double salt of the diazo from 4-diethylaminoo-phenetidine and the azo coupling component is 1.8-dihydroxy-naphthalene-4-sulfonic acid.
4. The process of producing cyan diazotype prints capable of transmitting both green and blue light which comprises sensitizing a transparent base with a composition containing as a light sensitive diazo compound a diazotized p-phenylene-diamine in which one of the amino groups is di-substituted by members selected from the class consisting of alkyl and hydroxyalkyl and as a coupling component a compound of the following formula:
R OH
ammonia vapor.
SAM C. SLlFKlN. THADDEUS J. TROJNAR.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS Number Name Date 1,710,455 Langguth et al Apr. 23, 1929 2,375,366 Jacobus May 8, 1945
Claims (1)
1. LIGHT SENSITIVE DIAZOTYPE MATERIAL FOR USE IN PRODUCING A CYAN RECORD IN THE DIAZOTYPE COLOR PROCESS COMPRISING A TRANSPARENT BASE CARRYING AS A LIGHT SENSITIVE DIAZO COMPOUND A DIAZOTIZED P-PHENYLENE-DIAMINE IN WHICH ONE OF THE AMINO GROUPS IS DI-SUBSTITUTED BY MEMBERS SELECTED FROM THE CLASS CONSISTING OF ALKYL AND HYDROXYALKYL AND AS THE AZO COMPONENT A COMPOUND OF THE FOLLOWING FORMULA:
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL69307D NL69307C (en) | 1947-06-06 | ||
| NL62286500A NL140419B (en) | 1947-06-06 | PROCESS FOR PREPARING AT LEAST TWO COMPONENTS WITH DIFFERENT VAPOR PRESSURES CONTAINING VAPOR. | |
| US753036A US2494906A (en) | 1947-06-06 | 1947-06-06 | Cyan component for diazotype color process |
| GB9137/48A GB635120A (en) | 1947-06-06 | 1948-03-31 | Cyan azo-coupling component for diazotype color process |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US753036A US2494906A (en) | 1947-06-06 | 1947-06-06 | Cyan component for diazotype color process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2494906A true US2494906A (en) | 1950-01-17 |
Family
ID=25028879
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US753036A Expired - Lifetime US2494906A (en) | 1947-06-06 | 1947-06-06 | Cyan component for diazotype color process |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US2494906A (en) |
| GB (1) | GB635120A (en) |
| NL (2) | NL140419B (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2694009A (en) * | 1948-10-01 | 1954-11-09 | Keuffel & Esser Co | Diazo-n-sulfonate light-sensitive material |
| DE1035474B (en) * | 1951-11-30 | 1958-07-31 | American Optical Corp | Process for the production of multicolor photographic images by applying a polyvinyl alcohol film with diazo compounds and copying on the partial color images |
| US3406071A (en) * | 1963-09-14 | 1968-10-15 | Keuffel & Esser Co | Naphthol sulfonamides as coupling components for light-sensitive diazotype materials |
| US3480437A (en) * | 1965-11-30 | 1969-11-25 | Gaf Corp | Two component diazo sensitizing compositions containing a xanthine compound |
| US3536490A (en) * | 1964-04-28 | 1970-10-27 | Pitney Bowes Inc | Novel diazotype copying process |
| US3769013A (en) * | 1968-08-07 | 1973-10-30 | Mita Industrial Co Ltd | Wet type diazotype developer |
| US3849138A (en) * | 1961-03-24 | 1974-11-19 | Applied Photo Sciences | Color photography |
| CN110670074A (en) * | 2019-11-05 | 2020-01-10 | 朱玉军 | Environment-friendly deformed steel bar surface antirust treating agent and preparation method thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1710455A (en) * | 1926-07-09 | 1929-04-23 | Langguth Werner | Process for producing photographs in natural colors |
| US2375366A (en) * | 1941-10-16 | 1945-05-08 | Keuffel & Esser Co | Photosensitive materials |
-
0
- NL NL69307D patent/NL69307C/xx active
- NL NL62286500A patent/NL140419B/en unknown
-
1947
- 1947-06-06 US US753036A patent/US2494906A/en not_active Expired - Lifetime
-
1948
- 1948-03-31 GB GB9137/48A patent/GB635120A/en not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1710455A (en) * | 1926-07-09 | 1929-04-23 | Langguth Werner | Process for producing photographs in natural colors |
| US2375366A (en) * | 1941-10-16 | 1945-05-08 | Keuffel & Esser Co | Photosensitive materials |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2694009A (en) * | 1948-10-01 | 1954-11-09 | Keuffel & Esser Co | Diazo-n-sulfonate light-sensitive material |
| DE1035474B (en) * | 1951-11-30 | 1958-07-31 | American Optical Corp | Process for the production of multicolor photographic images by applying a polyvinyl alcohol film with diazo compounds and copying on the partial color images |
| US3849138A (en) * | 1961-03-24 | 1974-11-19 | Applied Photo Sciences | Color photography |
| US3406071A (en) * | 1963-09-14 | 1968-10-15 | Keuffel & Esser Co | Naphthol sulfonamides as coupling components for light-sensitive diazotype materials |
| US3536490A (en) * | 1964-04-28 | 1970-10-27 | Pitney Bowes Inc | Novel diazotype copying process |
| US3480437A (en) * | 1965-11-30 | 1969-11-25 | Gaf Corp | Two component diazo sensitizing compositions containing a xanthine compound |
| US3769013A (en) * | 1968-08-07 | 1973-10-30 | Mita Industrial Co Ltd | Wet type diazotype developer |
| CN110670074A (en) * | 2019-11-05 | 2020-01-10 | 朱玉军 | Environment-friendly deformed steel bar surface antirust treating agent and preparation method thereof |
| CN110670074B (en) * | 2019-11-05 | 2021-11-16 | 北美防锈技术（上海）有限公司 | Environment-friendly deformed steel bar surface antirust treating agent and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| NL140419B (en) | |
| NL69307C (en) | |
| GB635120A (en) | 1950-04-05 |
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