US2717832A - Diazotype materials for black line images containing diresorcyl sulfide or sulfoxide as a subsitiute for resorcinol - Google Patents
Diazotype materials for black line images containing diresorcyl sulfide or sulfoxide as a subsitiute for resorcinol Download PDFInfo
- Publication number
- US2717832A US2717832A US454837A US45483754A US2717832A US 2717832 A US2717832 A US 2717832A US 454837 A US454837 A US 454837A US 45483754 A US45483754 A US 45483754A US 2717832 A US2717832 A US 2717832A
- Authority
- US
- United States
- Prior art keywords
- diresorcyl
- sulfoxide
- resorcinol
- sulfide
- subsitiute
- 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
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 title claims description 15
- 239000000463 material Substances 0.000 title claims description 12
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 title description 22
- 150000003462 sulfoxides Chemical class 0.000 title description 4
- 150000001989 diazonium salts Chemical class 0.000 claims description 10
- 230000008878 coupling Effects 0.000 claims description 9
- 238000010168 coupling process Methods 0.000 claims description 9
- 238000005859 coupling reaction Methods 0.000 claims description 9
- WUDPYTUCYMDYKB-UHFFFAOYSA-N 2-(2,6-dihydroxyphenyl)sulfinylbenzene-1,3-diol Chemical compound OC1=CC=CC(O)=C1S(=O)C1=C(O)C=CC=C1O WUDPYTUCYMDYKB-UHFFFAOYSA-N 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 5
- DKJVSIITPZVTRO-UHFFFAOYSA-N 6,7-dihydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(O)C(O)=CC2=C1 DKJVSIITPZVTRO-UHFFFAOYSA-N 0.000 claims description 3
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 239000002585 base Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 4
- 235000005074 zinc chloride Nutrition 0.000 description 4
- 239000011592 zinc chloride Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical compound CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 description 2
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical compound CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 0.000 description 1
- AHAKNNFVXPHIHB-UHFFFAOYSA-N 4-phenylcyclohexa-3,5-diene-1,1,3-triol Chemical group C1(=C(CC(C=C1)(O)O)O)C1=CC=CC=C1 AHAKNNFVXPHIHB-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 241000238370 Sepia Species 0.000 description 1
- 229920002472 Starch Polymers 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
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- HTKFORQRBXIQHD-UHFFFAOYSA-N allylthiourea Chemical compound NC(=S)NCC=C HTKFORQRBXIQHD-UHFFFAOYSA-N 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
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- -1 as the case may be Chemical compound 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000003230 hygroscopic agent Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- GPUMPJNVOBTUFM-UHFFFAOYSA-N naphthalene-1,2,3-trisulfonic acid Chemical compound C1=CC=C2C(S(O)(=O)=O)=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC2=C1 GPUMPJNVOBTUFM-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
- LGQLOGILCSXPEA-UHFFFAOYSA-L nickel sulfate Chemical compound [Ni+2].[O-]S([O-])(=O)=O LGQLOGILCSXPEA-UHFFFAOYSA-L 0.000 description 1
- 229910000363 nickel(II) sulfate Inorganic materials 0.000 description 1
- FATBGEAMYMYZAF-KTKRTIGZSA-N oleamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(N)=O FATBGEAMYMYZAF-KTKRTIGZSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
- 229960001553 phloroglucinol Drugs 0.000 description 1
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 229930182490 saponin Natural products 0.000 description 1
- 150000007949 saponins Chemical class 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 239000000080 wetting agent 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
Definitions
- diazotype materials which are capable of being processed to black images.
- all such materials contain at least three coupling components, i. e., one which yields a yellow-green image, another whlch yields a blue image, and a third, normally considered a shading component, which yields a yellow-brown image.
- Diresorcyl Sulfide Diresorcyl Sulfoxz'de OH OH OH OH OH carbonate, stripping the ether from the organic layer and crystallizing the sulfide from water.
- the sulfoxide In the event that the sulfoxide is to be employed, it may be prepared from the water-wet sulfide by suspending the same in water at C., and oxidizing the suifide with an excess of hydrogen peroxide at 65-75 C.
- Resorcinol to complement the shading action of the diresorcyl comsitive diazonium compounds are those from N-diethyl-pphenylenediamine; N-dimethyl-p-phenylenediamine; N- dipropyl-p-phenylenediamine; N-ethyl-N-B-hydroxyethylp-phenylenediamine; N-methyl-fi-hydroxyethyl-p-phenylenediamine and the like.
- a metal halide such as zinc chloride, aluminum chloride, tin tetrachloride and the like.
- the coating solution in addition to the coupling components and the light sensitive diazonium compound, may also contain the various adjuncts usual in the manufacture of light sensitive diazotype materials. These include metal salts for intensification of the dyestuff image, such as ammonium sulfate, nickel sulfate,. zinc chloride and the like; stabilizing. agents such asthiourea, thiosinamine, naphthalene trisulfonic acid and the like; acids acting to retard precoupling such.
- metal salts for intensification of the dyestuff image such as ammonium sulfate, nickel sulfate,. zinc chloride and the like
- stabilizing. agents such asthiourea, thiosinamine, naphthalene trisulfonic acid and the like
- acids acting to retard precoupling such.
- acetic acid boric acid, tartaric acid and the like
- hygroscopic agents such as glycol, glycerin and the like
- wetting agents such as saponin, lauryl sulfonate, keryl benzene sulfonate, the oleic acid amide of N-methyl taurine and the like.
- the base to which the coatingv solution is applied may be any fibrous base which has been previously suggested for employment in the diazotype field.
- Examples of such bases are high grade all-sulfite bond paper, rayon or cotton cloth, starch filled cloth and the like.
- Example I An all sulfite bond paper was coated with the following solution and dried:
- Example II The procedure is the same as in Example I, excepting that the diresorcyl sulfoxide is replaced by an equimolecular quantity of diresorcyl sulfide.
- Example III The procedure is the same as in Example I, excepting that the light sensitive diazonium compound is the zinc chloride double salt of the diazonium compound from N-ethyl-N-B-hydroxyethyl-p-phenylenediamine which is employed in an amount equivalent to the sensitizer in Example I.
- the light sensitive diazonium compound is the zinc chloride double salt of the diazonium compound from N-ethyl-N-B-hydroxyethyl-p-phenylenediamine which is employed in an amount equivalent to the sensitizer in Example I.
- the product obtained is comparable in properties to the product of the preceding examples.
- Example IV The procedure is the same as in Example I, excepting that there is used one gram of diresorcyl sulfide and 0.8 gram of resorcinol.
- the paper compounded in this fashion yielded prints of a neutral black even after storage for a considerable period in a humid atmosphere.
- Example V 75 minus the figures given in the examples, particularlywhen the absorbency of the paper coated is taken into consideration.
- a storage stable light sensitive diazotype material capable of producing black azo dye images upon printing and development comprising a fibrous base coated With a light sensitive diazonium compound of the pphenylenediamine class and a mixture of coupling components comprising acetoacetanilide, 2,3-dihydroxy naphthalene-6-sulfonic acid and a diresorcyl derivative selected from the class of diresorcyl sulfide and diresorcyl sulfoxide.
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)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE539176D BE539176A (de) | 1954-09-08 | ||
| US454837A US2717832A (en) | 1954-09-08 | 1954-09-08 | Diazotype materials for black line images containing diresorcyl sulfide or sulfoxide as a subsitiute for resorcinol |
| DEG17507A DE1004919B (de) | 1954-09-08 | 1955-07-02 | Schwarz entwickelbares Diazotypiematerial |
| FR1129578D FR1129578A (fr) | 1954-09-08 | 1955-07-08 | Matériel diazotype photosensible pour images en traits noirs |
| CH338091D CH338091A (de) | 1954-09-08 | 1955-07-27 | Schwarzzeichnendes Diazotypiematerial |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US454837A US2717832A (en) | 1954-09-08 | 1954-09-08 | Diazotype materials for black line images containing diresorcyl sulfide or sulfoxide as a subsitiute for resorcinol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2717832A true US2717832A (en) | 1955-09-13 |
Family
ID=23806310
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US454837A Expired - Lifetime US2717832A (en) | 1954-09-08 | 1954-09-08 | Diazotype materials for black line images containing diresorcyl sulfide or sulfoxide as a subsitiute for resorcinol |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US2717832A (de) |
| BE (1) | BE539176A (de) |
| CH (1) | CH338091A (de) |
| DE (1) | DE1004919B (de) |
| FR (1) | FR1129578A (de) |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3184310A (en) * | 1959-01-21 | 1965-05-18 | Azoplate Corp | Reproduction layers for printing plates |
| US3200135A (en) * | 1959-07-29 | 1965-08-10 | Sterling Drug Inc | Copper, cadmium, and zinc salts of halo-2, 2'-dihydroxydiphenyl sulfides and sulfoxides |
| US3429814A (en) * | 1966-04-05 | 1969-02-25 | Mobil Oil Corp | Grease compositions |
| US3499763A (en) * | 1967-05-01 | 1970-03-10 | Ibm | Bis phenols as high opacity diazotype couplers |
| US3619191A (en) * | 1967-09-13 | 1971-11-09 | Tecnifax Corp The | Diazo-type materials |
| US3836369A (en) * | 1972-09-05 | 1974-09-17 | Du Pont | Diazo photosensitive composition |
| US3857896A (en) * | 1967-09-13 | 1974-12-31 | R Desjarlais | Substituted diresorcyl sulfide and sulfoxide compounds |
| US3867147A (en) * | 1969-05-20 | 1975-02-18 | Hoechst Co American | Light-sensitive diazo compounds and reproduction material employing the same |
| US3881931A (en) * | 1972-05-22 | 1975-05-06 | Fuji Photo Film Co Ltd | Method for developing black diazotype photographic light-sensitive materials |
| US4207110A (en) * | 1977-10-17 | 1980-06-10 | Hoechst Aktiengesellschaft | Diazotype material |
| US4304831A (en) * | 1978-08-08 | 1981-12-08 | Ricoh Co., Ltd. | Black-color forming two-component type diazo copying material |
| US4642383A (en) * | 1982-09-30 | 1987-02-10 | James River Graphics, Inc. | Fast coupling lemon-yellow phenolic couplers |
-
0
- BE BE539176D patent/BE539176A/xx unknown
-
1954
- 1954-09-08 US US454837A patent/US2717832A/en not_active Expired - Lifetime
-
1955
- 1955-07-02 DE DEG17507A patent/DE1004919B/de active Pending
- 1955-07-08 FR FR1129578D patent/FR1129578A/fr not_active Expired
- 1955-07-27 CH CH338091D patent/CH338091A/de unknown
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3184310A (en) * | 1959-01-21 | 1965-05-18 | Azoplate Corp | Reproduction layers for printing plates |
| US3200135A (en) * | 1959-07-29 | 1965-08-10 | Sterling Drug Inc | Copper, cadmium, and zinc salts of halo-2, 2'-dihydroxydiphenyl sulfides and sulfoxides |
| US3429814A (en) * | 1966-04-05 | 1969-02-25 | Mobil Oil Corp | Grease compositions |
| US3499763A (en) * | 1967-05-01 | 1970-03-10 | Ibm | Bis phenols as high opacity diazotype couplers |
| US3619191A (en) * | 1967-09-13 | 1971-11-09 | Tecnifax Corp The | Diazo-type materials |
| US3857896A (en) * | 1967-09-13 | 1974-12-31 | R Desjarlais | Substituted diresorcyl sulfide and sulfoxide compounds |
| US3867147A (en) * | 1969-05-20 | 1975-02-18 | Hoechst Co American | Light-sensitive diazo compounds and reproduction material employing the same |
| US3881931A (en) * | 1972-05-22 | 1975-05-06 | Fuji Photo Film Co Ltd | Method for developing black diazotype photographic light-sensitive materials |
| US3836369A (en) * | 1972-09-05 | 1974-09-17 | Du Pont | Diazo photosensitive composition |
| US4207110A (en) * | 1977-10-17 | 1980-06-10 | Hoechst Aktiengesellschaft | Diazotype material |
| US4304831A (en) * | 1978-08-08 | 1981-12-08 | Ricoh Co., Ltd. | Black-color forming two-component type diazo copying material |
| US4642383A (en) * | 1982-09-30 | 1987-02-10 | James River Graphics, Inc. | Fast coupling lemon-yellow phenolic couplers |
Also Published As
| Publication number | Publication date |
|---|---|
| BE539176A (de) | |
| DE1004919B (de) | 1957-03-21 |
| CH338091A (de) | 1959-04-30 |
| FR1129578A (fr) | 1957-01-23 |
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