Classifications

• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
  • C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
  • C09B23/04—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups one >CH- group, e.g. cyanines, isocyanines, pseudocyanines

Definitions

• Z represents a member from the group consisting of a sulfur atom or a selenium atom
• A represents a member from the group consisting of a hydrogen atom, a lower alkyl group or a hydroxyl group
• B represents a member from the group consisting of a hydrogen atom or a lower alkyl group
• R and R represent a member from the group consisting of a dye is an intramolecul ar salt.
• a photographic light-sensitive element comprising the i above emulsion on a support is also claimed.
• the present invention relates to a silver halide photographic emulsion containing a sensitizing dye, and more particularly to a silver halide photographic emulsion containing a thia-2'- cyanin sensitizing dye or a selena-2-cyanin sensitizing dye which has a hydroxyl group in the 5-position of the benzothiazole nucleus or the benzoselena zole nucleus, and in which a nucleus nitrogen atom in either of the heterocyclic rings is substituted by a sulfoalkyl group or carboxyalkyl group.
• the spectral sensitizing technique of addingcertain sensitizing dyes to a silver halide emulsion-to further enlarge its light sensitive wavelength range has been well known in the manufacturing technique of silver halide photographic emulsion.
• the sensitizing dye to be contained in the silver halide photographic emulsion should be such as to provide the desired spectral sensitivity without having a bad influence upon the photographic sensitive materials.
• a silver halide photographic emulsion which is spectrally sensitized often brings about a color-stain caused by the sensitizing dye after the conventional treatments of development, fixing, washing with water, etc.
• the color-stain derived from this dye will act to impede visible judgment ofthe image during printing by virtue of short wavelength lightor platemaking.
• 2 represents a member from the group consisting of a sulfur atom or a selenium atom
• A represents a member from the group consisting of a hydrogen atom, alower alkyl group or a hydroxyl group
• B represents a member from the group consisting of a hydrogen atom or a lower alkyl group
• R andR' represent a member from the group consisting of a lower alkyl group or a substituted alkyl group, and at least one ofR and-R represent a member from the groupconsistingof a sulfoalkyl group or a carboxyalkyl group
• X representsan anion
• n represents 0 or I, n being ()when the sensitizing dye is an intramolecular salt.
• the above emulsion finds particularuse in a photographic light-sensitive element, wherein the emulsion iscarried on a support.
• an object of the present invention is to provide a silver halide photographic emulsion having lower color-stain caused by the sensitizing dye, which is produced after carrying out the conventional treatments of development, fixing, washingwith water, etc. Further, the emulsion will have a high sensitivity in the green sensitive range.
• Another object of the present invention is to provide a silver halide photographic emulsion having a high sensitivity in the green sensitive range used for a printing or duplication orthofilm, cinema recording film, and indirect photography Roentgen film for medical treatment, etc.
• the above objects of the present invention havebeen accomplished by incorporating at least one S-hydroxythia- 2'- cyanin or 5-hydroxyselena- 2'-cyanin sensitizing dyes represented by the fonnula T x-).. r't' (I) wherein Z represents a sulfur atom or a selenium atom; A represents a hydrogen atom, a lower alkyl group, -i.e., one-four carbon atoms, (for example, methyl group. ethyl group, etc.), or a hydroxyl group; B represents a hydrogen atom, or a.
• R and R represent an alkyl group (for example, methyl group, ethyl group, propyl group, etc.) or a substituted alkyl group (for'example.
• the sulfosubstituted alkyl group can have from one to six carbon atoms and the carboxy substituted alkyl group can have from one to ID carbon atoms. Further.
• alkyl group which may be component R or R are carboxyl groups, hydroxyl groups, alkoxyl groups. a sulfogroup, an aralkyl groupora vinylgroup.
• X represents ananiom suchas a halogen ion (Cl, Br. I), a p-toluene sulfonate ion. -C H O -SO etc.
• R, X, and n 1 have the same meaning as-in formula (I); and.R"' representsa methyl group, an ethyl group, or a phenyl .group. etc'.,.and:a*
• the sensitizing dye represented by formula (I) can be obtained by the hydrolysis of a sensitizing dye having an alkoxy group in the 5-position of the benzothiazole nucleus, or of a benzoselenazole nucleus with a mineral acid.
• the sensitizing dye of formula (I) used in the present invention as A is a hydroxyl group may be obtained by the hydrolysis of a sensitizing dye of formula (l) wherein group A is replaced with an alkoxy groupfor wherein group A is replaced with an alkoxy group and the 5-position of the benzothiazole nucleus or the benzoselenazole nucleus has an alkoxy group, with a mineral acid.
• Dye(7) 5 Anhydro l-ethyl-5-hydroxy-6'-methyl-3-(8-sulfobutyl thia-2'-cyanin hydroxide HC s I 10 CH- V-on l CgHs l5 (cmnso;
• Dye 1 Anhydro 5,6'-dihydroxy-l '-ethyl-3-(6-sulfopropyl)-thia-2'- cyanin hydroxide
• Other sensitizing dyes used in the present invention may be prepared in a similar manner to the aforesaid procedure. and typical dyes are illustrated in the following table, together with the above-prepared dyes.
• nit-on suitable solvent such as methanol, ethanol. etc. is added to the emulsion.
• the amount of sensitizing dye to be added to the emulsion can be varied over the broad range ofS to I50 mg. per 1 kg. of emulsion. according to the desired final objects.
• the photographic emulsion of the presentinvention can be hypersensitized. and supersensitized. in the preparation of the photographic emulsion of the present invention.
• additives conventionally used such as, a sensitizer. a stabilizer. a toning agent. a hardening agent. a surface active agent. an antifogging agent. a plasticizer. a developing promotor, a coupier. and a fluorescent whitening agent. may further be added to the emulsion by any conventional method.
• the photographic emulsion can be applied to a suitable support.
• a suitable support such as a glass, a film of cellulose derivative. a film of synthetic resin. or a baryta paper by any conventional method.
• the emulsion wascoated on a film base of cellulose triacetate and, after drying. exposed to a "day light" of 64 lux (corresponding to 5400 K) through a Fuji No. 17 filter (a green filter, transparent maximum at 525 to 530 u, manufactured by Fuji Photographic Film Co.. Ltd.) and developed.
• the developing solution of the composition shown in table 1 was employed at 20 C. for the development temperature.
• the silver halide to be used in the emulsion of the present TIER-f1 550 3. 640 invention can be various silver salts such as silver chloride. Ag 22; silver bromide, silver iodobromide. silver chlorobromide, and 0.08 2min 55%560 3. 7 0 silver chloroiodobromide. Agltli 292 g???
• the sensitized photographic emulsion of the present inven- 2K3) Hi0 2.800 tion may be prepared by adding one or more kinds of sensitiz- 3: 8g g i ⁇ : mg dye to the photographic emulsion by the conventional -0 211E761 55x: M 00 7 method. Most practically.
• the color-stain value shows the density through a Fuji No. 17 filter(transparent maximum 525 to 530 mu. manufactured by Fuji Photographic Film Co.. Ltd.)
• n 0 or l, n being 0 when the sensitizing dye is an intramolecular salt.
• a photographic light-sensitive element comprising a support having thereon the photographic silver halide emulsion layer as set forth in claim 1.

Landscapes

• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Silver Salt Photography Or Processing Solution Therefor (AREA)
• Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
• Thiazole And Isothizaole Compounds (AREA)

Applications Claiming Priority (1)

Publications (1)

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ID=12849608

Family Applications (1)

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Citations (2)

• 1969
  • 1969-06-30 BE BE735402D patent/BE735402A/xx unknown
  • 1969-07-16 US US842361A patent/US3619197A/en not_active Expired - Lifetime
  • 1969-07-16 GB GB1238785D patent/GB1238785A/en not_active Expired
  • 1969-07-16 DE DE1936262A patent/DE1936262C3/de not_active Expired

Patent Citations (2)

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