US2656351A - Trinuclear dyes containing a 5-thiazolidone nucleus - Google Patents

Trinuclear dyes containing a 5-thiazolidone nucleus Download PDF

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US2656351A
US2656351A US220332A US22033251A US2656351A US 2656351 A US2656351 A US 2656351A US 220332 A US220332 A US 220332A US 22033251 A US22033251 A US 22033251A US 2656351 A US2656351 A US 2656351A
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those
series
nucleus
emulsion
dyes
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Aubert Per
Roy A Jeffreys
Edward B Knott
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Eastman Kodak Co
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Eastman Kodak Co
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    • 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
    • C09B23/0075—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain being part of an heterocyclic ring
    • C09B23/0083—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain being part of an heterocyclic ring the heteroring being rhodanine in the chain
    • 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
    • G03C1/08—Sensitivity-increasing substances
    • G03C1/10—Organic substances
    • G03C1/12—Methine and polymethine dyes
    • G03C1/26—Polymethine chain forming part of a heterocyclic ring

Definitions

  • This invention relates to trinuclear dyes concarbon atoms in the cycloalkyl ring), e and n taining a 5-thiazolidone nucleus and to methods each represents a positive integer from 1 to 2, for preparing them. More particularly, this in- (1 represents a positive integer from 1 to 3, X vention relates to trinuclear dyes useful in alter- H represents an anion, such as Cl, Br", I-, C104", ing the sensitivity of photographic silver halide p-CH3-C6H4--SO3, C6E5-SO3", CHSCOC", emulsions. SCN-.
  • L represents a methine group
  • Z and Trinuclear dyes obtained from merocyanine Z1 each represents the non-metallic atoms necesdyes containing a rhodanine nucleus have presary to complete a heterocyclic nucleus containviously been described.
  • Such dyes, h) ring such as those selected from the group conin certain cases, can advantageously be employed sisting of those of the thiazole series (e. g.
  • chlorobenzothiazole, 6-chlorobenzothiazole, '7- provide new trinuclear dyes.
  • a further object chlorobenzothiazole, 4-methylbenzothiazole, 5- is to provide methods for preparing these dyes.
  • Still another object is to provide photographic bromobenzothiazole, 6 -bromobenzothiazo1e, 4- silver halide emulsions containing these new dyes, phenylbenzothiazole, 5 phenylbenzothiazole, 4 and methods for preparing these emulsions.
  • R, R1, and R2 each represents an alkyl 4-methyloxazo1e, 5-methyloxazole, 4-pheny1oxgroup, such as methyl, et y sop y -propy azole, 4,5-diphenyloxazole, 4-ethyloxazo1e, 4,5-din-butyl, isobutyl, n-amyl, n-heptyl, n-octyl, ⁇ 3- methyloxazole, 5-phenyloxazole, etc.), those of hydroxyethm, p-acetoxyethyl, etc. groups (e. g.
  • benzoxazole series e. g. benzoxazole, 5-chloan alkyl group of the formula CmH2m+1 wherein 4-5 robenzoxazole, 5-methylbenzoxazole, S-phenylm represents a positive integer from 1 to 8
  • benzoxazole,'G-methylbenzoxazole, 5,6-dimethy1- and R1 can, in addition, represent alkyl groups, benzoxazole, 4,6 dimethylbenzoxazole, 5 methh as the cycloalkyl groups, e. g.
  • benzoselenazole series e. g. benzoselenazole, 5 chlorobenzoselenazole, 5 methoxybenzoselenazole, 5 hydroxybenzoselenazole, tetrahydrobenzoselenazole, etc.
  • naphthoselenazole series e. g. anaphthoselenazole, fl-naphthose
  • dine series e. g. pyridine, 5-methylpyridine, ctc.
  • Q represents the non-metallic atoms necessary to complete a heterocyclic nucleus containing from five to six atoms in the heterocyclic ring, such as those selected from the group consisting of a thiazolone nucleus, for example, a 2,4(3,5)-thiazoledione nucleus, such as 2,4(3,5) thiazoledione, 3-ethyl-2,4(-3,5)-thiazoledione, 3- phenyl-2,4(3,5) -thiazoledione or 3-naphthyl-2,-4 (3,5)-thiazoledione nuclei, a -2-thio-2-,4(3,5) -thiazoledione (a rhodanine) nucleus, such as 3-alkyl- 2-thio-2,4(3,5) -thiazoledione (3-alkylrhodanine) 3 phenyl-2-thio-2,4(3,5) thiazoledione (3 phenylrh
  • 3,4-dihydro-2 l) -quinclone nucleus such as 3,4-dihydro-2(1)-quinolone (dihydrocarbostyril) a 3,4 dihydro-2(1)- quinoxalone nucleus, such as 3,4-dihydro-2(1)- quinoxalone (oxydihydroquinoxaline) 3-phenomorpholone (l,4,2-benzoxazine-3(4)-one or benzo-fl-morpholone) nuclei; 1,4,2-benzothiazine-3 (4)-one (ketodihydrobenzoparathiazine) nuclei, and the like six-membered heterocyclic nuclei.
  • the dyes wherein Q represents the non-metallic atoms necessary to complete a heterocyclic nucleus containing five atoms in the heterocyclic ring, three of said atoms being carbon atoms, one of said atoms being a nitrogen atom, and the other of said atoms being a sulfur atom, a nitrogen atom, or an oxygen atom, have been found to be especially well adapted to the manufacture of photographic emulsions, we have found.
  • R, R1, L, n, d, and Z have the values set forth above
  • R3 represents an alkyl group, such as methyl, ethyl, n-hexyl, etc. groups
  • X1 represents an anion, such as those represented by X above, for example, with a compound selected from those represented by the following general formula:
  • R2, Z1, X, and e have the values set forth above.
  • the condensations can advantageously be carried out in the presence of a basic condensing agent, such as the trialkylamines, e. g. triethylamine, tri-n-propylamine, tri-n-butylamine etc., dialkylanilines, e. g. N,N-dimethylaniline, N,N- diethylaniline, etc., N-alkylpiperidines, e. g. N- methylpiperidine, N-ethylpiperidine, etc., heterocyclic amines. e. g. pyridine, quinoline, isoquinoline, etc., N-alkylpyrroles, e. g. N-methylpyrrole, etc.
  • a basic condensing agent such as the trialkylamines, e. g. triethylamine, tri-n-propylamine, tri-n-butylamine etc., dialkylanilines, e. g.
  • The-condensations can also be carried out in the presence of an inert solvent, such as the lower aliphatic alcohols, e. g. ethyl, n-propyl, isopropyl, n-butyl, isobutyl, etc. alcohols, diethyl ether, .1,4-dioxane,'benzene, n-hexane, etc. Heat accelcrates the condensations, and temperatures varying from about 25 C. to the reflux temperature of the reaction mixture can be used.
  • an inert solvent such as the lower aliphatic alcohols, e. g. ethyl, n-propyl, isopropyl, n-butyl, isobutyl, etc. alcohols, diethyl ether, .1,4-dioxane,'benzene, n-hexane, etc. Heat accelcrates the condensations, and temperatures varying from about 25
  • R, R1, n, d, L, and Z have the values given above, with an alkyl salt, such as those represented by the following general formula:
  • the reaction mixture set to a solid, and it was then ground to a powder and washed with dry benzene. It was recrystallized from an ethanol-diethyl ether mixture as red prisms with a blue reflex having a melting point of 222 C. It sensitized a gelatino silver chloride emulsion with a maximum at 510 ma and a gelatino silver bromide emulsion with a maximum at 530 ma.
  • Example 3 [2-(3-ethylbenzomazole) l [4-(2-eth ylthio 5(4) thiazoloneH dimethinemerocyanine ethiodide 2.0 g. of [2-(3-ethylbenzoxazole)][4-(2-ethylthio 5(4)-thiazolone)] dimethinemerocyanine and 10 cc. of ethyl iodide were fused together in a sealed tube at C. for 24 hours. The tube was then openedand the excess ethyl iodide driven off. The residue was recrystallized from ethanol as soft, rust-colored needles having a melting point of 136 C.
  • Example 5 [4-(1-ethylquinoline) [4 (Z-methylthzo 5(4) thiazolone) ldz'methinemerocya-
  • Example 6. [2 (B-ethylbenzoxazoleH [4 (2- methyZthio-S (4) -thiazolone) dimethinemerocyanine n-hepto-pt0luensalfonate zHl 1.0 g. of [2-(3-ethylbenzoxazole)l heptyl-2-thio-2,5 (3,4) -thiazoledione) [4- (3-ndimethinemerocyanine and 0.5 g. of methyl p-toluenel sulfonate were heated together at 120 C. for 30 minutes. The red solid obtained was ground to a powder, heated under reflux with benzene, and the benzene removed by decantation.
  • Example 1 0 .?--[2:-(S ethglbenzothiaaole)1: Lei-(.2; methyLthio-fifl)--thiazolone%l; dimetmnmem cyanine metho-p-toluenesulfanmte' 4.3 g. of EZ-(B-ethylbenzothiazolell [4-(3- methy1-2-thio-2,5(3,4) -thiazo1edione) dimethi-nemerocyanine and 2.9 g. of methyl p-toluene sulfonate wereheated together at 130 62..
  • This dye was prepared in the same manner as m nut
  • the Solid product w ground to a the dye of Example l-3 by replacing theZ-methylowder, washed.
  • the mixture, it was obtained asmaroomleaflets me fi desired product was: obtained as. maroon. needles ing at 182-? C. (6.2". g.)
  • the dye was recrystallized from a pyridine-diethyl ether mixture as small bluish needles melting at 310 C. It sensitized a gelatino silver chloride emulsion with maxima at 540 and 570 ml and a gelatino silver bromide emulsion with a maximum at 610 m
  • the reaction mixture was then chilled, and the precipitate collected on a filter. After recrystallization from aniline, the dye was obtained as a dark olive-green powder having a melting point of 234 C.
  • Example 20 [2- (1 -ethylquinoline) ] ⁇ 2- [4- (2- [3 ethylbenzoxazolinylidenel ethylidene) -3-n-heptyl-5 (4) -thiazolonel ⁇ methinecryanine iodide
  • Example 21 --[4-(1-ethylquinoline)] ⁇ 2-[4-(2- [3-ethylbenzoxazolinylidenel ethylidene)-3-nhepiyl 5(4) thiazolonel ⁇ methinecyanine iodide 0.5 g. of the quaternary salt obtained in Example 6 above, 0.26 g.
  • Example 2.3 [2-(3a6thZ/Zb3722011l20l3) 1 ⁇ 4- ⁇ 2- (5-omo-2-n-octg thzo 4 thiazolz'nylidene)-.3- .cyclohemyl-5-thz'azolidone] ⁇ dimethz'nemerocycame 01115 aHn ethylamine, and cc. of-ethanol, and the resulting solution was heated on a steam bath for 30 minutes and then chilled. The precipitate was collected on a filter and recrystallized from ligroin as yellow-green prisms melting at 150 C. It sensitized a gelatino silver chloride emulsion" with maxima at 400 and 590 m and a gelatino silver bromiodide emulsion with a maximum at 610 mu.
  • Example 24 [.2 .(3 a methylbenzothiazolefl ⁇ 2- [4 (.2 l3 ethylbeneomaaolinylidene] ethyl idene) -.3-.ethyl 5 .thz'azolidoneil ⁇ azamethinecyamne p-toluenesulfonate maxima at 400 and 560 m and a gelat-ino silver bromiodide emulsion with a maximum 9.17 530 me- 12 Example 2 5.
  • Example 28 ⁇ 4 (1 ethylquinoline) ⁇ 2 [4- (2-[ 3 ethylbenzoxazolinylidene]ethylidene)- 3 ethyl 5 thiazolidone] ⁇ methinecyanine iodide 0.488 g. of the quaternary salt obtained in Example 3 above, 0.299 g. of lepldine ethiodide, 0.2 cc. of triethylamine, and cc. of ethanol were refluxed for 30 minutes, and the solution then chilled.
  • the precipitate (0.4 g.) was collected on a filter and recrystallized from a methanol-diethyl ether mixture as glittering blue-black crystals melting at 272 C. It sensitized a gelatino silver chloride emulsion with a maximum at 6'70 m
  • Example 36 It sensitized a gelatino silver bromiodide emulsion with a maximum at 650 my"
  • Example 36 - ⁇ 2-(3-ethylbenzothiaeole) ⁇ 4-[2- (Z-n-heptylthz'o 5-oxo-4-thiazolinylidene)-3- methyl .5 thz'aolidonc] ⁇ dimethinemerocyanine 0.7 g. of N-(dithiocarbo-n-heptoxy) glycine and 7 cc. of acetic anhydride were heated for minutes on a steam bath, and the unreacted acetic anhydride and acetic acid formed during the reaction removed under a vacuum.
  • N-(dithiocarbo-n-octoxy)glycine used in Example 23 above was prepared as follows:
  • Example 37 --N-(.dithiocarbo-n-octowy)glycine 22.4 g. of potassium hydroxide were dissolved in cc. of water and the solution chilled. There were then added 15.0 g. of glycine and 15.2 g. of carbondisulfide, and the whole shaken mechanically until a clear orange solution resulted. A solution of 38.6 g. of n-octylamine in 50 cc. of ethanol was added, and the mixture heated for 30 minutes on a steam bath. To the resulting one-phase solution there were added 100 cc. of water, and the cloudiness resulting removed by extraction with diethyl ether.
  • the aqueous layer was warmed gently under reduced pressure to expel any dissolved ether, the solution chilled, and acidified with concentrated hydrochloric acid.
  • the precipitate was collected on a filter. washed with water, air-dried, and. recrystallized from petroleum ether (13. P. -80" C.) as glistennsp'lates melting at 100 o.
  • Example 27 The ,N-Lthiocarbo-n-octoxy) glycine used in Example 27 above was prepared as follows:
  • d represents a positice
  • X represents an anion
  • Q represents the non-metallic atoms necessary solvent.
  • Methanol or acetone has proved satisto complete a heterocyclic nucleus containing 5 factory as a solvent for most of our new dyes. atoms in the heterocyclic ring, 3 of said atoms.
  • the dyes are quite insoluble in methyl being carbon atoms, 1 of said atoms being a alcohol, a mixture of acetone and pyridine is nitrogen atom, and the other of said atoms being advantageously employed as a solvent.
  • the dyes selected from the group consisting of an oxygen are advantageously incorporated in the finished, atom, a sulfur atom, and a nitrogen atom, and Zv washed emulsionsand should be uniformly disand Z1 each represents the non-metallic atoms tributed throughout the emulsions.
  • the parnecessary to complete a heterocyclic nucleus seticular solvent used Will, of course, depend on the lected from the group consisting of those of the solubility properties of the'particular dye.
  • the concentration of the dyes in the emulsions those of the naphthothiazole series, those of the can vary widely, e. g. from 5 to 100 mg. per liter oxazole series, those of the benzoxazole series, of flowable emulsion.
  • concentration of the those of the napththoxazole series, those of the dyes will vary according to the type of emulsion selenazole series, those of the benzoselenazole' and according to the effect desired.
  • the trinuclear dye represented by the m1- dispersed in the emulsion. lowmg formula! With most of our dyes, from 10 to 20 mg.
  • N N s A trinuclear dye selected from the group 6, 4111;
  • R-, R1, and E3 eachrepresents arr alkyl group ofthe formula; ,QmHzmerr wherein m-representsa positive-integer from 1 to 8; X1 represents" agranion; n represents a; positive integer-from If to 2; 11:- represents a positive integer-"from 1* to 3'; and" Z; represents the non-metallicatoms necessary to complete a heterocyolie nucleus selected from thegroup consisting of-those of the thiazole series, thoseof the benzothiazole series; those of the naphthothiazole series, those of theoxazoleseries; thoseof the 'benzoxazole series, those of' the naphthoxazoleseries,- those of?
  • m6 b wherein- Q- represents the non-metallic atoms necessary to completea heterocyoliolnucleus containing -atoms in the heterocyclic ring; 3of said atome-bein icarhoniatoms, 1* f; said; etomebein at nitrogeni atom. and the; otherofi said: atoms e ng; sel atedfrom; the group consistin of; an: oxy e atom a sulfun atom: andsanitmgsm atom; and cyolammoniumaquaternary salt; seleotedsimm, thoise: represented by. the; followinggeneral; 103- mu a;
  • R2 represent an alkyl group of the formula CmHZuH-l wherein m represents a positive integer from 1 to 8, X represents an anion, e represents, a; positi-te integerfrom; 1 to 21 and Z1, represents the: non-metallic, atoms necessary to, complete.- a heterocyolic nueleus selected from the. groupconsisting: of, those; of the thiazole; series, thoseeof the benzot-hiazole series, thoseoh the-naphthothiazole: series, thoseoi the oxazole:

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US220332A 1951-03-02 1951-03-02 Trinuclear dyes containing a 5-thiazolidone nucleus Expired - Lifetime US2656351A (en)

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FR1086259D FR1086259A (fr) 1951-03-02 1952-02-29 Nouveaux composés trincléaires, procédé pour leur préparation et leurs applications notamment en photographie

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2743272A (en) * 1952-03-28 1956-04-24 Eastman Kodak Co Sensitizing dyes containing a 4-aryl-5-aryloxy- or 5-arylthiothiazole nucleus
US3094418A (en) * 1960-03-10 1963-06-18 Eastman Kodak Co Silver halide meulsions containing cationic oxonol and benzylidene dyes
US3930869A (en) * 1973-01-12 1976-01-06 Mitsubishi Paper Mills, Ltd. Photographic silver halide photosensitive materials

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2170804A (en) * 1937-04-24 1939-08-29 Eastman Kodak Co Merocyanine dyes from benzoxazoles
US2388962A (en) * 1938-01-24 1945-11-13 Allied Chem & Dye Corp Dry cleaning composition

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2170804A (en) * 1937-04-24 1939-08-29 Eastman Kodak Co Merocyanine dyes from benzoxazoles
US2388962A (en) * 1938-01-24 1945-11-13 Allied Chem & Dye Corp Dry cleaning composition

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2743272A (en) * 1952-03-28 1956-04-24 Eastman Kodak Co Sensitizing dyes containing a 4-aryl-5-aryloxy- or 5-arylthiothiazole nucleus
US3094418A (en) * 1960-03-10 1963-06-18 Eastman Kodak Co Silver halide meulsions containing cationic oxonol and benzylidene dyes
US3930869A (en) * 1973-01-12 1976-01-06 Mitsubishi Paper Mills, Ltd. Photographic silver halide photosensitive materials

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BE509612A (is")

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