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N-ylide compounds as antistatic agents in photography

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US3704128A
US3704128A US3704128DA US3704128A US 3704128 A US3704128 A US 3704128A US 3704128D A US3704128D A US 3704128DA US 3704128 A US3704128 A US 3704128A
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Prior art keywords
light
sensitive
material
group
photographic
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Ken Ichi Koda
Shoji Kikuchi
Tsuneo Wada
Yoshimi Kuwabara
Akira Horikoshi
Kensaku Tanimura
Sadao Sugita
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Konica Corp
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Konica Corp
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic 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
    • C07D213/02Heterocyclic 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
    • C07D213/04Heterocyclic 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
    • C07D213/60Heterocyclic 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 heteroatoms or with carbon atoms having three bonds to hetero atoms, with at the most one to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78Carbon atoms having three bonds to hetero atoms, with at the most one to halogen, e.g. ester or nitrile radicals
    • C07D213/86Hydrazides; Thio or imino analogues thereof
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ELECTROGRAPHY; HOLOGRAPHY
    • G03CPHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00Photosensitive materials
    • G03C1/005Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
    • G03C1/06Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ELECTROGRAPHY; HOLOGRAPHY
    • G03CPHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00Photosensitive materials
    • G03C1/005Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
    • G03C1/06Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
    • G03C1/34Fog-inhibitors; Stabilisers; Agents inhibiting latent image regression
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ELECTROGRAPHY; HOLOGRAPHY
    • G03CPHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00Photosensitive materials
    • G03C1/76Photosensitive materials characterised by the base or auxiliary layers
    • G03C1/85Photosensitive materials characterised by the base or auxiliary layers characterised by antistatic additives or coatings
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ELECTROGRAPHY; HOLOGRAPHY
    • G03CPHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C5/00Photographic processes or agents therefor; Regeneration of such processing agents
    • G03C5/26Processes using silver-salt-containing photosensitive materials or agents therefor
    • G03C5/29Development processes or agents therefor
    • G03C5/305Additives other than developers

Abstract

WHEREIN R1, R2 AND R3 ARE INDIVIDUALLY AN ALKYL GROUP, AN ARALKYL GROUP OR A GROUP DERIVED FOR ANY OF SAID GROUPS, AND R4 IS AN ALKYL GROUP, AN ARYL GROUP OR A HETERO RING.

R1-N(+)(-R2)(-R3)-N(-)-CO-R4

A NEW USE, AS AN ANTISTATIC AGENT FOR LIGHT-SENSITIVE SILVER HALIDE PHOTOGRAPHIC MATERIAL, OR AN N-UYLIDE REPRESENTED BY THE GENERAL FORMULA

Description

United States Patent Int. Cl. G03c 5/26, 1/02 US. Cl. 96-50 5 Claims ABSTRACT OF THE DISCLOSURE A new use, as an antistatic agent for light-sensitive silver halide photographic material, of an N-ylide represented by the general formula 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.

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.

When a light-sensitive silver halide photographic material is developed, undesired images in the form of branched lines and fluffs are frequently observed. These undesired images are the so-called static marks. It is believed that the formation of such static marks is ascribable to the fact that the surface of light-sensitive material is electrostatically charged due to friction and this electrostatic charge is discharged to excite the light-sensitive material. Such electrostatic charge results not only in the formation of static marks but also in the adhesion of dust onto the surface of light-sensitive material. Such electrostatic effects are unavoidably brought about every time light-sensitive materials undergo friction and is seen in almost all stages of production and handling of lightsensitive materials, e.g. in such film production stages as the coating of emulsions and the cutting and packaging of films, and in such film handling stages as the withdrawal of films from boxes, the taking of pictures by use of films, particularly those for movies, and the handling of films before development. Further, such electrostatic trouble is sometimes brought about also in the case of releasing lightsensitive materials. For example, in releasing in succession a light-sensitive material, which has been rolled up, in general, after completion of coating and drying operations, in order to transfer the light-sensitive material to the sub- 3,704,128 Patented Nov. 28, 1972 ice sequent step, or in unrolling in succession a rolled photographic paper in order to subject the photographic paper to printing operation, a static charge is generated between the surface and the reverse side of the peeled or unrolled light-sensitive material when the material is peeled from the roll portion. Further, in removing a photographic paper, which has been subjected to ferrotype drying, there is also generated an electrostatic charge between the drying surface (metal) and the surface of the photographic paper at the moment of separation, so that the paper can not be stacked at once.

In order to overcome such static trouble, a process is used by which hygroscopic materials are incorporated into the layers constituting light-sensitive materials. This process, however, is effective only when humidity is relatively high and is ineffective at dry times when the static trouble most frequently takes place. Further, if the humidity is excessively high, the above-mentioned process brings about troubles in the mutual adhesion between gelatinous layers of separate light-sensitive materials. In addition to the above-mentioned hygroscopic materials, there are a considerable number of compounds which are known as antistatic agents. However, antistatic agents are required to be such that they should not have any detrimental effects on such photographic properties of light-sensitive materials as sensitivity, gradation, fog, stability, etc. Therefore it is extremely diflicult to fin'd excellent antistatic agents applicable to light-sensitive silver halide photographic materials.

As a result of extensive studies on excellent antistatic agents which have no detrimental effects on light-sensitive silver halide photographic materials, it has been found that a compound represented by the general formula 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, is an excellent antistatic agent.

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. Further, 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.

Typical examples of the N-ylide represented by the aforesaid general formula are as shown hereinafter.

\B e RPM-N001! Elementary analysis Calculated Found R; B: R; R H N c H N 1 0H, CH; CH, 0.11" 68.37 12.36 12.27 66. 85 12.55 11.88 11 0H. CH; CH; C11H2: 70.26 12.58 10.93 69.72 12.76 10.61 III 0H, CH; OH; 01511;. 73.01 12.00 8.96 72.12 12. 70 8.20

IV CH 0H. CH Q 67.38 7.92 15.72 66.80 8.19 16.00

v 0H, 0H, CH, C 60.31 7.31 23. 45 50.92 7.22 24.11

VI CHI CH: CzHa ClsHu .56 12.96 8.58 72. 12.76 8.34 v11 CH; on, our! CH1 71.05 12.67 10.36 70.06 12.45 10.15

VIII CH1 CH1 011B" 77.26 11. 41 7.21 76. .37 7.06

IX CHI CHI 051111 55.05 7.08 8. 56 54. 60 7. 28 8.11

C1H| 0111111 71.77 12.76 9.85 70.03 12.53 9.13 01H. 151111 74. 51 13.08 7.90 73. 66 12. 65 7.28 011111 C1Hu 74.42 12.83 9.39 72.55 12.85 9. 42

crnonom- 0,,H,. 67.94 12.07 9.32 68.02 12.33 9.38

C.H1|(|3HCH; C lEhr- 71.29 12.51 7.56 17 31 12.50 7.66

The 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). 40 Alternatively, 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. of N-dimethylN-hexadecanoyl Per the 11 ght'senS1t1ve mater1a1, though the hydrazine in 40 m1 of methyl iodide was fl d for amount varies depending on the kinds of the compound 22 hours. After completion of the reaction, excess methyl and of the layeriodide was removed by distillation under reduced pres- The compounfls of the Present mventlon are apPheable sure, and the residue was recrystallized from methanol for the e Preventwn of films: fibers and molded to obtain 142 of N i h 1 N' d l hydrw articles of cellulose esters, polyesters, polystyrenes polyzinium iodate, yield 963% 1424430 carbonates, polyethylenes, polypropylenes and the like Elementary analysis.-Calculated (for C H ON I) synthenc resmsg (percent): C, 5L5; H, N, 636. Found (percent): The present invention is illustrated 1n further detail C, 5220; H N, 6.61 below with reference to examples. 11 g. of this hydrazinium iodate was suspended in 30 I, EXAMPLE 1 ml. of water, and to the suspension was added with stir- Th d f h f I ring a solution of 1.5 g. of sodium hydroxide in 10 ml. 6 Compoun o t e of water. Subsequently, the liquid was heated over a G9 9 water bath at 50-60 C. for 20 minutes. After cooling, the T liquid was extracted 3 times with 60 ml., 30 ml. and 30 ml. 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. anhydrous sodium sulfate by filtraand then the film Was dried to P p a p The tion, the chloroform was removed by distillation under Same Y h as above s mmersed for 1 minute in reduced pressure, and the resulting crystals were recrysthe ahove-mehtloned Solution and then dried to Prepare tallized from petroleum benzine to obtain 73 g. of N-trianother p on the Other hand, two contfolrsamples methylamine hexadecanimide, yield 93.5%, M.P. 71.5- were P p 1n the Same manner as above, except that the above-mentioned N-ylide compound was not used. Elementary analysis.Calculated (for C H ON The thus prepared 4 kinds of samples were allowed to (percent): C, 73.01; H, 12.90; N, 8.96. Found (percent): stand for 24 hours under conditions of a relative humidity C, 72,12; H, 12,79; N, 8,20. of 30% and a temperature of 25 C. Thereafter, the For the incorporation into any of the layers constitut- 75 samples were abraded on the surfaces with nylon and polyester cloths and then subjected, without exposure, to ordinary development using a developing solution. As the result, considerably marked generation of static marks was observed on both of the control films, whereas no generation of static marks was observed on the films treated with the solution of the N-ylide compound (i.e. the light-sensitive materials of the present invention). On the other hand, 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. Provided that in the above case, 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. As the result, it was observed that 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.

EXAMPLE 4 |1O g. of the cyan coupler l-hydroxy-N-['y-(2,4-diamylphenoxy)propyl]-2-naphthamide was dissolved at an elevated temperature in a mixed liquid comprising 10 g. of dibutyl phthalatc and 30 g. of ethyl acetate. Subsequently, the liquid was charged into cc. of 10% gelatine in the presence of 40 cc. of a 1% solution of dodecylbenzenesulfonic acid, and then the mixture was dispersed by means of a ultrasonic disperser to form a suspension. 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. 0n the other hand, 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:

[the compound of exemplification (VII)]. These two light-sensitive materials were subjected to entirely the same tests as in Example 1 to find that in the case of the light-sensitive material prepared by use of the compound of exemplification (VII), not only the generation of static marks had been completely inhibited but also the coupler had been increased in dispersibility and the developed dye image had been improved in transparency. In the tests, the treatments were carried out according to ordinary color negative treatments.

What we claim is:

1. 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.

2. 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.

3. A process for the antistatic treatment of a lightsensitive silver halide photographic material as claimed in claim 2, wherein said solution further contains a surface active agent.

4. 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.

5. A new use as an antistatic agent for light-sensitive silver halide photographic material, of an N-ylide represented by the general formula 7 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.

References Cited UNITED STATES PATENTS 3,113,026 12/1963 Sprung 96190 3,549,369 12/1970 Koda 96-94 8 FOREIGN PATENTS 864,874 4/1961 Great Britain 96-87 US. Cl. X.R.

US3704128A 1969-03-14 1970-03-11 N-ylide compounds as antistatic agents in photography Expired - Lifetime US3704128A (en)

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Cited By (9)

* Cited by examiner, † Cited by third party
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

Cited By (14)

* Cited by examiner, † Cited by third party
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
US5734082A (en) * 1994-10-20 1998-03-31 Arqule Inc. Hydroxyethyl aminimides
US5892113A (en) * 1994-10-20 1999-04-06 Arqule, Inc. Hydroxyethyl aminimides
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
US5962736A (en) * 1995-01-20 1999-10-05 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

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JPS494853B1 (en) 1974-02-04 grant
GB1268164A (en) 1972-03-22 application
DE2011876A1 (en) 1970-09-24 application

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