US3881929A - Stabilizing a photosensitive composition containing an n-vinyl heterocyclic compound and an organic halogen compound with an azabicycloene compound - Google Patents
Stabilizing a photosensitive composition containing an n-vinyl heterocyclic compound and an organic halogen compound with an azabicycloene compound Download PDFInfo
- Publication number
- US3881929A US3881929A US364315A US36431573A US3881929A US 3881929 A US3881929 A US 3881929A US 364315 A US364315 A US 364315A US 36431573 A US36431573 A US 36431573A US 3881929 A US3881929 A US 3881929A
- Authority
- US
- United States
- Prior art keywords
- compound
- group
- azabicycloene
- weight
- heavy metal
- 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
- 150000001875 compounds Chemical class 0.000 title claims abstract description 25
- 239000000203 mixture Substances 0.000 title claims abstract description 19
- 150000002896 organic halogen compounds Chemical class 0.000 title claims abstract description 9
- 230000000087 stabilizing effect Effects 0.000 title claims abstract description 8
- 229920002554 vinyl polymer Polymers 0.000 title claims abstract description 8
- 229910001385 heavy metal Inorganic materials 0.000 claims abstract description 14
- 239000004094 surface-active agent Substances 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims description 13
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 8
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 8
- 235000019422 polyvinyl alcohol Nutrition 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 7
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 7
- 108010010803 Gelatin Proteins 0.000 claims description 5
- 229910019142 PO4 Inorganic materials 0.000 claims description 5
- 229920000159 gelatin Polymers 0.000 claims description 5
- 239000008273 gelatin Substances 0.000 claims description 5
- 235000019322 gelatine Nutrition 0.000 claims description 5
- 235000011852 gelatine desserts Nutrition 0.000 claims description 5
- 239000011347 resin Substances 0.000 claims description 5
- 229920005989 resin Polymers 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 4
- 239000010452 phosphate Substances 0.000 claims description 4
- 229920001817 Agar Polymers 0.000 claims description 3
- 241000206672 Gelidium Species 0.000 claims description 3
- 239000002202 Polyethylene glycol Substances 0.000 claims description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 235000010419 agar Nutrition 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- 229920002401 polyacrylamide Polymers 0.000 claims description 3
- 229920001223 polyethylene glycol Polymers 0.000 claims description 3
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 3
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 3
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 3
- 239000011135 tin Substances 0.000 claims description 3
- 229910052718 tin Inorganic materials 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- 239000011701 zinc Substances 0.000 claims description 3
- LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical compound CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 0.000 claims description 2
- HVWGGPRWKSHASF-UHFFFAOYSA-N Sulfuric acid, monooctadecyl ester Chemical class CCCCCCCCCCCCCCCCCCOS(O)(=O)=O HVWGGPRWKSHASF-UHFFFAOYSA-N 0.000 claims description 2
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical class CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 claims description 2
- TVACALAUIQMRDF-UHFFFAOYSA-N dodecyl dihydrogen phosphate Chemical class CCCCCCCCCCCCOP(O)(O)=O TVACALAUIQMRDF-UHFFFAOYSA-N 0.000 claims description 2
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical class CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- KWPQTFXULUUCGD-UHFFFAOYSA-N 3,4,5,7,8,9,10,10a-octahydropyrido[1,2-a][1,4]diazepine Chemical compound C1CCN=CC2CCCCN21 KWPQTFXULUUCGD-UHFFFAOYSA-N 0.000 claims 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 claims 1
- 150000001409 amidines Chemical class 0.000 claims 1
- WENNKWXPAWNIOO-UHFFFAOYSA-N undecan-5-one Chemical compound CCCCCCC(=O)CCCC WENNKWXPAWNIOO-UHFFFAOYSA-N 0.000 abstract 1
- 239000003381 stabilizer Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000000470 constituent Substances 0.000 description 7
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 6
- 229910001864 baryta Inorganic materials 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000000654 additive Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 230000005855 radiation Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 235000021317 phosphate Nutrition 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- -1 vinyl heterocyclic Chemical class 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical compound CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229910003310 Ni-Al Inorganic materials 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ZUBJEHHGZYTRPH-KTKRTIGZSA-N [(z)-octadec-9-enyl] hydrogen sulfate Chemical compound CCCCCCCC\C=C/CCCCCCCCOS(O)(=O)=O ZUBJEHHGZYTRPH-KTKRTIGZSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 229940043264 dodecyl sulfate Drugs 0.000 description 1
- 229940071161 dodecylbenzenesulfonate Drugs 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 150000002505 iron Chemical class 0.000 description 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- NGCRXXLKJAAUQQ-UHFFFAOYSA-N undec-5-ene Chemical compound CCCCCC=CCCCC NGCRXXLKJAAUQQ-UHFFFAOYSA-N 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 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
- G03C5/00—Photographic processes or agents therefor; Regeneration of such processing agents
- G03C5/56—Processes using photosensitive compositions covered by the groups G03C1/64 - G03C1/72 or agents therefor
-
- 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
- G03C1/675—Compositions containing polyhalogenated compounds as photosensitive substances
Definitions
- This invention relates generally to a photographic composition. More particularly, it relates to a photographic image stabilizer used for stabilizing images obtained with organic photosensitive compositions comprising N-vinyl heterocyclic and organic halogen compounds.
- Photographic images produced in an organic photosensitive coating on baryta paper are liable to color change when subjected to daylight exposure for a period of 3 to 7 days. During this period, a yellow-tobrown color change would take place in the lightstruck areas, and a further exposure to daylight would turn the whole areas to brown. Such color change is detrimental to the preservation of photographic images for an extended period of time.
- Color change may be attributable to a number of factors which include photo-oxidization of dyes p'roduced upon exposure to light, subsequent photoreaction of the unexposed areas, and a subsequent photo-reaction of unreacted substances which may be present in the dyes. Color change may also depend on the amount of organic halogen compounds present in the lightexposed areas.
- additives and stabilizers For purposes of stabilizing images, additives and stabilizers have been proposed which include peroxides (U.S. Pat. No. 3,544,320), aldehyde-NaHSO (U.S. Pat. No. 3,503,742), Na SO and NaHSO (U.S. Pat. No. 3,512,976) and various mixtures thereof (U.S. Pat. No. 3,544,322).
- peroxides U.S. Pat. No. 3,544,320
- aldehyde-NaHSO U.S. Pat. No. 3,503,742
- Na SO and NaHSO U.S. Pat. No. 3,512,976
- various mixtures thereof U.S. Pat. No. 3,544,322
- the image stabilizer comprises as its main constituent an azabicycloene compound ofa cyclic amidine expressed generally by the following formula:
- the image stabilizer according to the invention is obtained by dissolving 0.5 to 20% by weight of the azabicycloene compound into an aqueous solution of, for example, about 20% polyvinyl alcohol.
- a preferred value of the azabicycloene content in the solution is from 4 to l% by weight.
- the azabicycloene compounds employed in the practice of the present invention are l,5-diazabicyclo [5,4,0] undecane-S ene and 1,5- diazabicyclo [4,3,0] nonene-S.
- These azabicycloene compounds may be dissolved either in water, in an aqueous solution containing a water-soluble resin or a polymer dissolving organic solvent organic.
- the lightexposed film may be dipped into the solution or it may be sprayed or wiped with the solution and the solvent is then removed by drying the film in the ambient atmosphere.
- These azabicycloene compounds are strongly alkaline and therefore they serve to decompose organic halogen compounds present in the light-exposed areas as intermediates of a photo-reaction to thereby stabilize the images formed.
- the desensitizing compounds would allow the whiteness of background areas to increase, which would otherwise turn to light yellowgreen. This could result in an increase in the image contrast.
- azabicycloene compounds also have a desensitizing effect on this background areas by increasing their whiteness while penetrating deeply into the photosensitive composition with the aid of a heavy metal salt of a surface active agent which will be described hereinbelow.
- the desensitizing effect is enhanced by heating the film at a temperature of about 50C for a period of about 30 seconds.
- the aforementioned water soluble resin may be natural high polymers such as gelation and agar-agar, or polyvinyl alcohol, polyethylene glycol, polyacrylamide, polyvinylpyrrolidone and polyacryl acid.
- the organic solvent may be, for example, alcohol, acetone, tetrahydrofuran, dimethylformamide, etc.
- polymers dissolved in one of the above-stated organic solvents such substances as polyacrylate, polyvinyl compounds, polycondensated compounds including polyamid derivatives may be used.
- the present invention contemplates the use of other compounds as additives to the azabicycloene compounds such as a heavy metal salt of a surface active agent such as sulfate, sulfonate, or phosphate.
- a surface active agent such as sulfate, sulfonate, or phosphate.
- the surface active agent usually a sodium salt
- the desensitizing effect can be further enhanced by the use of a heavy metal salt such as, for example, a zinc, tin or an iron salt.
- the additive to the azabicycloene compounds may preferably be heavy metal laurylsulfate, oleylsulfate, stearylsulfate, laurylsulfonate, dibutylnaphtalenesulfonate, dodecylbenzenesulfonate, oleyletherphosphate and laurylphosphate. More preferably, the additive may be Zn-dibutyl-naphthalenesulfonate or stannous sulfonate. These additives are used in a concentration of about 0.5 to 20 weight percent in the solvent.
- pyrrolidone is reacted with acrylonitrile by heating in the presence of potassium hydroxide and hydroquinone.
- the product is acidified with hydrochloric acid and then concentrated under a reduced pressure to give I-( 2-cyanoethyl )-pyrrolidone.
- the thus obtained nitrile is dissolved in a mixture of methanol and ammonia and subjected to catalytic reduction by the use of a Ni-Al catalyst, followed by filtration, vacuum concentration and vacuum distillation.
- the distilled product which is l-( 3-aminopropyl)-pyrrolidone, is then dissolved in xylol and admixed with p-toluenesulfonic acid, followed by reflux for a dehydration reaction.
- the final reaction product is subjected to filtration and vacuum distillation.
- All the above sulfates, sulfonates and phosphates are well known and are commercially available surface active agents as their respective sodium salts.
- the heavy metal salts for the stabilizer of the invention are known and can be easily obtained by usual replacement reactions of such sodium salts with, e.g., chlorides of the preferred heavy metals, which reactions require no detailed description for one skilled in general chemistry.
- a sheet of baryta paper was coated with the thus obtained composition.
- the photosensitive film thus formed on the baryta paper had a wet thickness of microns.
- the coated sheet After the coated sheet had been dried, it was subjected to an imagewise exposure by a 250 watt xenon lamp from a distance of about I meter for 1 second through a suitable image pattern placed in an intermediate position between the lamp and the film.
- a second exposure was made by subjecting the film to light of wavelengths above 5300 A from a 100 watt tungsten lamp through an optical filter for a period of 5 seconds.
- a negative image was produced in the film when it was left under the influence of ambient light radiation.
- a stabilizer was prepared by mixing the following constituents and the image produced on the baryta paper was coated with the mixture:
- the stabilizer coated film was heated to, and kept at 50C for 30 seconds: For purposes of comparison, a separate negative image without the stabilizer coating was also produced in the same manner as described above and exposed to the radiation of a 40 watt fluorescent light from a distance of 30cm. The light-exposed areas started to change their color to yellow in 3 days and turned totally brown within one week. In contrast, the stabilizer-coated image did not appreciably change in color even after a one-week exposure to the same fluorescent radiation.
- a sheet of baryta paper was coated with the thus obtained composition.
- the photosensitive film was subjected to light exposures as described in Example I to develop a negative image.
- a stabilizer was prepared by mixing the following constituents and the image produced on the baryta paper was coated with the mixture:
- Example 1 A similar desensitizing effect was observed as in Example 1 when the film was subjected to a one-week exposure to the 40 watt fluorescent light.
- n and n are each an integer ranging from 2 to 6; and drying the wet image and background areas at a temperature ranging from room temperature to 50C.
- said aqueous solution further contains up to 50% by weight of a water-soluble resin selected from the group consisting of gelatin, agar-agar, polyvinyl alcohol, polyethylene glycol, polyacrylamide, polyvinylpyrrolidone and polyacryl acid.
- a water-soluble resin selected from the group consisting of gelatin, agar-agar, polyvinyl alcohol, polyethylene glycol, polyacrylamide, polyvinylpyrrolidone and polyacryl acid.
- said aqueous solution further contains 0.5 to by weight of a heavy metal salt of a surface active agent selected from the group consisting of a sulfate, sulfonate and phosphate, said heavy metal being selected from the group consisting of zinc, tin and iron.
- azabicycloene compound is selected from the group consisting of l,5-diazabicyclo( 4,3,0)nonene-5 and 1,5-
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP47054670A JPS5218021B2 (enrdf_load_stackoverflow) | 1972-05-31 | 1972-05-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3881929A true US3881929A (en) | 1975-05-06 |
Family
ID=12977200
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US364315A Expired - Lifetime US3881929A (en) | 1972-05-31 | 1973-05-29 | Stabilizing a photosensitive composition containing an n-vinyl heterocyclic compound and an organic halogen compound with an azabicycloene compound |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US3881929A (enrdf_load_stackoverflow) |
| JP (1) | JPS5218021B2 (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1987003387A1 (en) * | 1985-11-27 | 1987-06-04 | Macdermid, Incorporated | Thermally stabilized photoresist images |
| US20130230929A1 (en) * | 2010-06-29 | 2013-09-05 | National Institute Of Advanced Industrial Science And Technology | Agent for detecting halide, method for detecting halide, and detection sensor |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4877104A (enrdf_load_stackoverflow) * | 1972-01-25 | 1973-10-17 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3512976A (en) * | 1966-07-21 | 1970-05-19 | Bell & Howell Co | Ammonium and metal sulfites as stabilizers of light sensitive systems |
-
1972
- 1972-05-31 JP JP47054670A patent/JPS5218021B2/ja not_active Expired
-
1973
- 1973-05-29 US US364315A patent/US3881929A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3512976A (en) * | 1966-07-21 | 1970-05-19 | Bell & Howell Co | Ammonium and metal sulfites as stabilizers of light sensitive systems |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1987003387A1 (en) * | 1985-11-27 | 1987-06-04 | Macdermid, Incorporated | Thermally stabilized photoresist images |
| US20130230929A1 (en) * | 2010-06-29 | 2013-09-05 | National Institute Of Advanced Industrial Science And Technology | Agent for detecting halide, method for detecting halide, and detection sensor |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5218021B2 (enrdf_load_stackoverflow) | 1977-05-19 |
| JPS4911321A (enrdf_load_stackoverflow) | 1974-01-31 |
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