US3704128A - N-ylide compounds as antistatic agents in photography - Google Patents
N-ylide compounds as antistatic agents in photography Download PDFInfo
- Publication number
- US3704128A US3704128A US18714A US3704128DA US3704128A US 3704128 A US3704128 A US 3704128A US 18714 A US18714 A US 18714A US 3704128D A US3704128D A US 3704128DA US 3704128 A US3704128 A US 3704128A
- Authority
- US
- United States
- Prior art keywords
- light
- sensitive
- solution
- compound
- silver halide
- 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
- 239000002216 antistatic agent Substances 0.000 title abstract description 9
- 150000001875 compounds Chemical class 0.000 title description 24
- 239000000463 material Substances 0.000 abstract description 53
- -1 SILVER HALIDE Chemical class 0.000 abstract description 22
- 229910052709 silver Inorganic materials 0.000 abstract description 22
- 239000004332 silver Substances 0.000 abstract description 22
- 239000000243 solution Substances 0.000 description 24
- 125000000217 alkyl group Chemical group 0.000 description 12
- 230000003068 static effect Effects 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000839 emulsion Substances 0.000 description 9
- 239000010410 layer Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000003710 aryl alkyl group Chemical group 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 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
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 230000001627 detrimental effect Effects 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 239000011241 protective layer Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000001828 Gelatine Substances 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 1
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- 244000046038 Ehretia acuminata Species 0.000 description 1
- 235000009300 Ehretia acuminata Nutrition 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- HEBRMUGNTGBIDY-UHFFFAOYSA-N I(=O)(=O)[O-].[NH3+]N Chemical class I(=O)(=O)[O-].[NH3+]N HEBRMUGNTGBIDY-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229940126208 compound 22 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 238000010981 drying operation Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- ICIWUVCWSCSTAQ-UHFFFAOYSA-M iodate Chemical compound [O-]I(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-M 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- SYXUBXTYGFJFEH-UHFFFAOYSA-N oat triterpenoid saponin Chemical compound CNC1=CC=CC=C1C(=O)OC1C(C=O)(C)CC2C3(C(O3)CC3C4(CCC5C(C)(CO)C(OC6C(C(O)C(OC7C(C(O)C(O)C(CO)O7)O)CO6)OC6C(C(O)C(O)C(CO)O6)O)CCC53C)C)C4(C)CC(O)C2(C)C1 SYXUBXTYGFJFEH-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/86—Hydrazides; Thio or imino analogues thereof
-
- 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
- G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
- G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
-
- 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
- G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
- G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
- G03C1/34—Fog-inhibitors; Stabilisers; Agents inhibiting latent image regression
-
- 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
- G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
- G03C1/85—Photosensitive materials characterised by the base or auxiliary layers characterised by antistatic additives or coatings
-
- 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
- G03C5/26—Processes using silver-salt-containing photosensitive materials or agents therefor
- G03C5/29—Development processes or agents therefor
- G03C5/305—Additives other than developers
Definitions
- This invention relates to a light-sensitive silver halide photographic material characterized by containing in at least one of the layers constituting the photographic material an N-ylide represented by the general formula shown hereinafter.
- a principal object of the present invention is to provide a light-sensitive silver halide photographic material having fewer drawbacks due to electrostatic charge.
- Another object of the invention is to provide a lightsensitive material resulting in an improved tone of developed silver image and a light-sensitive color photographic material which is excellent in image resolution and graimness.
- the above-mentioned compound When the above-mentioned compound is incorporated into at least one of the silver halide emulsion, subbing, inter, filter, anti-halation, protective and backing layers which constitute a light-sensitive silver halide photographic material, it is possible to obtain a light-sensitive silver halide photographic material markedly improved with respect to static trouble.
- the above-mentioned compound not only has no detrimental effects on such characteristics of a light-sensitive photographic material as speed, gradation, fog, and so forth but also displays, depending on the kind of light-sensitive material, such desirable effects as to inhibit fog and to enhance stability.
- the compound when the compound is applied to a light-sensitive black-and-white photographic material, there is attained, in addition to the prevention of electrostatic trouble, such advantage that the color tone of the developed silver image can be made bluish black and, when it is applied to a color photographic emulsion, having a color former incorporated therein, the dispersibility of the color former is improved to make it possible to obtain a light-sensitive color photographic material which is excellent in image resolution and graininess.
- N-ylide compounds 'of the aforesaid general for- 3? ing a light-sensitive silver halide photographic material, mula can be prepared according to any of the processes o the compound of the aforesaid general formula may be disclosed W. H. Berry & P. Brocklchurst in Journal of brought into the form of a solution in a suitable solvent the Chemical Society, 2264 (1964); R. H. I-linman in such as water or an alcohol, or the solution may be Journal of Organic Chemistry, 24 660 (1969); and R. C. sprayed onto the surface of the light-sensitive material. Slagel in Journal of Organic Chemistry, 33 1374 (1968).
- the light-sensitive material may be im-
- the preparation of a typical compound is set forth mersed in the solution of the compound. Further, the below with reference to a synthesis example.
- compound of the present invention may be added to a treating bath of developing solution, stopping solution, Syl 1thesls exafnp 1e fixing solution, water drop-preventing solution or the like. Synthesis of N-tnmethylamme h xad a d
- the amount of the compound to be incorporated into the [Exemphficatlon D] layer of a light-sensitive material is about 0.1 mg. to 1 A solution of 10 g.
- wmpound of x p fic was formed m of chloroform in this order, and the chloroform layer was a 1% aqueous Thls Soll-ltlon was p y Onto washed with an aqueous saturated sodium chloride soluthe Surface of a hlgh Speed Y film 80 that the amount tion and then dehydrated with anhydrous sodium sulfate. of the Compound became 10 g- P of the film, After separating the.
- these 4 kinds of films weresubjected to sensitometry according to the method specified in 118 K7609 whereby the light-sensitive silver halide photographic materials of the present invention gave such favorable results that not only no change was observed in speed, gradation and fog, but also the developed silver image tone changed to bluish black. Further, these films were developed after storing them for 3 days in a thermostat at 55 C., and under the conditions of a temperature of 50 C. and a relative humidity of 80%, respectively. In this case also, the light-sensitive silver halide photographic materials of the present invention gave desirable results.
- EXAMPLE 2 The compound of the formula 89 6 (C Ha) aN-NC O CuHst [the compound of exemplification (III)] was prepared in a 2% aqueous solution. To this solution was added cc. per liter of said solution of an 8% aqueous gelatine solution used as protective layer. Further, 2 cc. of a 5% saponine solution was added as a coating aid. The mixed solution thus formed was coated as a protective layer onto a high speed X-ray film, followed by drying. The resulting light-sensitive material was subjected, together with a light-sensitive material in which the above-mentioned compound had not been incorporated into the protective layer, to the same tests as in Example 1 to obtain the same results as in Example 1.
- EXAMPLE 3 30 cc. of a 3% methanol solution of the compound of the formula [the compound of exemplification (VIII)] was added to one liter of a green light-sensitive high speed silver iodobromide color photographic emulsion. To this emulsion was added a solution of 15 g. of 1-(4-carboxyphe'nyl)-3 (4-palmitoylaminobenzoylamino)-5-pyrazolone (magenta coupler) in a 1 N caustic soda solution, and the emulsion was adjusted to pH 6.8 by addition of citric acid.
- the thus prepared emulsion was coated onto a cellulose triacetate base, followed by drying, to obtain a light-sensitive silver halide photographic material.
- This light-sensitive material was subjected, together with a control prepared in the same manner as above except that the abovementioned N-ylide compound was not added, to entirely the same tests as in Example 1.
- the processing was effected in such a manner that each sample was subjected to ordinary color development using a color developing solution containing diethyl-pphenylenediamine as a main ingredient and then to waterwashing, bleaching, water-washing, fixing, water-washing and drying.
- the lightsensitive material of the present invention had been completely inhibited from generation of static marks and, in addition, had been enhanced in dispersibility of the coupler.
- This suspension was added to one liter of a red light-sensitive high speed silver iodobromide color photographic emulsion, which was then coated onto a polyester film base, followed by drying, to prepare a light-sensitive material.
- another lightsensitive material was prepared by repeating the above operation, except that to one liter of the emulsion was added 50 cc. of a 2% methanol solution of the compound of the formula 69 9 N-NCOCH:
- a light-sensitive silver halide photographic material comprising a plurality of layers and in at least one of the layers an N-ylide represented by the general formula Eg -900R R: wherein R R and R are individually an alkyl group, and aralkyl group or a group derived from any of said groups, and R is an alkyl group, an aryl group or a hetero ring.
- a process for the antistatic treatment of a lightsensitive silver halide photographic material comprising treating said photographic material with an aqueous or organic solvent solution containing an ylide represented by the general formula 69 9 Ra NNCOR4 wherein R R and R are individually an alkyl group, an aralkyl group or a group derived from any of said groups, and R is an alkyl group, an aryl group or a hetero ring.
- a developingsolution for light-sensitive silver halide photographic materials comprising an N-ylide represented by the general formula Ra-N-NCOR4 RI wherein R R and R are individually an alkyl group, an aralkyl group or a group derived from any of said groups, and R is an alkyl group, an aryl group or a hetero ring.
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP44018909A JPS494853B1 (enrdf_load_stackoverflow) | 1969-03-14 | 1969-03-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3704128A true US3704128A (en) | 1972-11-28 |
Family
ID=11984712
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US18714A Expired - Lifetime US3704128A (en) | 1969-03-14 | 1970-03-11 | N-ylide compounds as antistatic agents in photography |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3704128A (enrdf_load_stackoverflow) |
| JP (1) | JPS494853B1 (enrdf_load_stackoverflow) |
| DE (1) | DE2011876A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1268164A (enrdf_load_stackoverflow) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3951662A (en) * | 1972-11-20 | 1976-04-20 | Konishiroku Photo Industry Co., Ltd. | Method of antistatic treatment for silver halide photosensitive materials |
| US4080206A (en) * | 1974-12-30 | 1978-03-21 | Polaroid Corporation | Photographic processing composition containing polyvinyl aminimide |
| US5670480A (en) * | 1994-01-05 | 1997-09-23 | Arqule, Inc. | Method of making polymers having specific properties |
| US5712171A (en) * | 1995-01-20 | 1998-01-27 | Arqule, Inc. | Method of generating a plurality of chemical compounds in a spatially arranged array |
| US5734082A (en) * | 1994-10-20 | 1998-03-31 | Arqule Inc. | Hydroxyethyl aminimides |
| US5766481A (en) * | 1995-04-06 | 1998-06-16 | Arqule, Inc. | Method for rapid purification, analysis and characterizations of collections of chemical compounds |
| US5962412A (en) * | 1996-06-10 | 1999-10-05 | Arqule, Inc. | Method of making polymers having specific properties |
| US5981467A (en) * | 1995-03-27 | 1999-11-09 | Arqule, Inc. | Aminimide-containing molecules and materials as molecular recognition agents |
| US7034110B2 (en) | 1994-01-05 | 2006-04-25 | Arqule, Inc. | Method of identifying chemical compounds having selected properties for a particular application |
-
1969
- 1969-03-14 JP JP44018909A patent/JPS494853B1/ja active Pending
-
1970
- 1970-03-11 US US18714A patent/US3704128A/en not_active Expired - Lifetime
- 1970-03-13 GB GB02344/70A patent/GB1268164A/en not_active Expired
- 1970-03-13 DE DE19702011876 patent/DE2011876A1/de active Pending
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3951662A (en) * | 1972-11-20 | 1976-04-20 | Konishiroku Photo Industry Co., Ltd. | Method of antistatic treatment for silver halide photosensitive materials |
| US4080206A (en) * | 1974-12-30 | 1978-03-21 | Polaroid Corporation | Photographic processing composition containing polyvinyl aminimide |
| US6271195B1 (en) | 1992-06-30 | 2001-08-07 | Arqule, Inc. | Aminimide-containing molecules and materials as molecular recognition agents |
| US5670480A (en) * | 1994-01-05 | 1997-09-23 | Arqule, Inc. | Method of making polymers having specific properties |
| US7034110B2 (en) | 1994-01-05 | 2006-04-25 | Arqule, Inc. | Method of identifying chemical compounds having selected properties for a particular application |
| US5892113A (en) * | 1994-10-20 | 1999-04-06 | Arqule, Inc. | Hydroxyethyl aminimides |
| US5734082A (en) * | 1994-10-20 | 1998-03-31 | Arqule Inc. | Hydroxyethyl aminimides |
| US5962736A (en) * | 1995-01-20 | 1999-10-05 | Arqule, Inc. | Logically ordered arrays of compounds and methods of making and using the same |
| US5736412A (en) * | 1995-01-20 | 1998-04-07 | Arqule, Inc. | Method of generating a plurality of chemical compounds in a spatially arranged array |
| US6878557B1 (en) | 1995-01-20 | 2005-04-12 | Arqule, Inc. | Logically ordered arrays of compounds and methods of making and using the same |
| US5712171A (en) * | 1995-01-20 | 1998-01-27 | Arqule, Inc. | Method of generating a plurality of chemical compounds in a spatially arranged array |
| US5981467A (en) * | 1995-03-27 | 1999-11-09 | Arqule, Inc. | Aminimide-containing molecules and materials as molecular recognition agents |
| US5766481A (en) * | 1995-04-06 | 1998-06-16 | Arqule, Inc. | Method for rapid purification, analysis and characterizations of collections of chemical compounds |
| US5962412A (en) * | 1996-06-10 | 1999-10-05 | Arqule, Inc. | Method of making polymers having specific properties |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1268164A (en) | 1972-03-22 |
| JPS494853B1 (enrdf_load_stackoverflow) | 1974-02-04 |
| DE2011876A1 (de) | 1970-09-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3811887A (en) | Photographic material comprising bisacylhydrazinium compounds | |
| EP0585679A1 (en) | Method for forming a photographic color image | |
| US4950586A (en) | Solid particle dispersions of filter dyes for photographic elements | |
| US3704128A (en) | N-ylide compounds as antistatic agents in photography | |
| US4499179A (en) | Silver halide photographic light-sensitive material | |
| US3794495A (en) | Prevention of static in light-sensitive photographic materials using bisaminimide compounds | |
| US3843368A (en) | Silver halide photographic light-sensitive element | |
| US4038075A (en) | Development of photographic silver halide material | |
| US3237008A (en) | Roomlight handling radiographic element including an x-ray sensitive layer overcoated with a dye desensitized silver halide emulsion | |
| US3161506A (en) | Photographic multicolor diffusion transfer process using dye developers | |
| US2982651A (en) | Anti-static photographic film | |
| US4954429A (en) | Silver halide color photographic material for laser recording | |
| EP0378236A1 (en) | Silver halide color photographic light-sensitive material | |
| US2808330A (en) | Photographic elements containing thiazolidine derivatives | |
| GB1598421A (en) | Method for the addition of photographic addenda | |
| US3938999A (en) | Antistatic photographic sensitive materials | |
| US2551134A (en) | Process of color developing with 2-thiohydantoin derivatives | |
| US3549369A (en) | Antistatic acylhydrazinium salt | |
| US3775128A (en) | Silver halide emulsion containing a triazine as antifoggant | |
| US3756828A (en) | Es photographic light sensitive material having good antistatic properti | |
| US3582340A (en) | Process for the antistatic treatment of light-sensitive silver halide photographic materials with phosphine oxide | |
| US3582338A (en) | Film elements and process of preparing same using electron bombardment | |
| EP0535999B1 (en) | Method for hardening gelatin | |
| GB2047418A (en) | Silver halide photographic materials | |
| US2685512A (en) | Photographic element containing arylidene derivative of fluorene |