GB1112034A - Merocyanine dyes,photographic silver halide emulsions containing them and multilayer photographic elements - Google Patents

Merocyanine dyes,photographic silver halide emulsions containing them and multilayer photographic elements

Info

Publication number
GB1112034A
GB1112034A GB18453/65A GB1845365A GB1112034A GB 1112034 A GB1112034 A GB 1112034A GB 18453/65 A GB18453/65 A GB 18453/65A GB 1845365 A GB1845365 A GB 1845365A GB 1112034 A GB1112034 A GB 1112034A
Authority
GB
United Kingdom
Prior art keywords
formula
alkyl
dyes
aryl
rhodanine
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
Application number
GB18453/65A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Eastman Kodak Co
Original Assignee
Eastman Kodak Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co
Publication of GB1112034A publication Critical patent/GB1112034A/en
Expired legal-status Critical Current

Links

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
    • C09B23/06—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups three >CH- groups, e.g. carbocyanines
    • 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
    • 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
    • C09B23/08—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups more than three >CH- groups, e.g. polycarbocyanines
    • C09B23/083—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups more than three >CH- groups, e.g. polycarbocyanines five >CH- groups
    • 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
    • C09B23/10—The polymethine chain containing an even number of >CH- groups
    • 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
    • C09B23/10—The polymethine chain containing an even number of >CH- groups
    • C09B23/105—The polymethine chain containing an even number of >CH- groups two >CH- groups
    • 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
    • C09B23/10—The polymethine chain containing an even number of >CH- groups
    • C09B23/107—The polymethine chain containing an even number of >CH- groups four >CH- groups
    • 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
    • G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
    • G03C7/392—Additives
    • G03C7/39208—Organic compounds
    • G03C7/39292—Dyes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises merocyanine dyes of the formulae <FORM:1112034/C4-C5/1> <FORM:1112034/C4-C5/2> wherein R is a substituted or unsubstituted alkyl or aryl group, Z completes a 5- or 6-membered heterocyclic nucleus, L is a methine group and one L may be substituted, j is 0 or 1, n is 0, 1, 2, or 3, Q is a <FORM:1112034/C4-C5/3> or <FORM:1112034/C4-C5/4> group, R1 is hydrogen, alkyl, aryl which may substituted, amino or substituted amino, carbonamido, sulphonamido, sulphamyl or carbamyl, W is oxygen or sulphur, at least one of Y and Y1 is a -(CH2)q-N(R2)R3, <FORM:1112034/C4-C5/5> or <FORM:1112034/C4-C5/6> group and, where only one of Y and Y1 is such a group, the other is hydrogen, alkyl or aryl, q is 2, 3 or 4, R2, R3 and R4 are each alkyl, R5, R6 and R7 are each hydrogen, alkyl or aryl, m is 0 or 1 and p is 0, 1 or 2. The dyes of Formula I above are made by condensing a compound of the formula <FORM:1112034/C4-C5/7> either with a compound of the formula <FORM:1112034/C4-C5/8> to give dyes of Formula I where n is 0, or with a compound of the formula <FORM:1112034/C4-C5/9> to give dyes of Formula I where n is 1 to 3, X being an acid anion, R8 being alkyl or aryl either of which may be substituted, J being -N(R9) R10, -SR11 or halogen, R9 being hydrogen, alkyl or carboxylic acyl and R10 being aryl or R9 and R10 together forming a heterocyclic ring, and R11 being alkyl. The dyes of Formula II are made by condensing a compound of the formula <FORM:1112034/C4-C5/100> with a compound of the formula <FORM:1112034/C4-C5/111> R12 being hydrogen or acetyl. The dyes are sensitizing dyes for silver halide emulsions (see Division G2).ALSO:In preparations, (1), 3 - (2 - diethylaminoethyl) - rhodanine, (2), 3 - (2 - morpholinoethyl) rhodanine, (7), 3 - (3 - dimethylaminopropyl) rhodanine, (9) 3 - [3 - (4 - methyl - 1 - piperazinyl)propyl] - rhodanine and 3 - (3 - diethylaminopropyl)rhodanine are made by reacting bis-(carboxymethyl) - trithiocarbonate with, respectively, N : N-diethyl-ethylenediamine, N - (2 - aminoethyl) - morpholine, N,N-dimethyl - 1,3 - propanediamine, 1 - (3 - aminopropyl) - 4 - methylpiperazine and N,N - diethyl - 1,3 - propanediamine and acidifying with HCl to obtain probably an impure hydrochloride; in (1) and (2) this is eluted through alumina to obtain the free bases and in (7), (9) and (10) it is reacted with sodium perchlorate to form the hydroperchlorate. In further preparations, (3), 3-(2-diethylaminoethyl) - 2 - thio - 2,4 - oxazolidenedione and, (4), 3 - (3 - dimethylaminopropyl) - 2 - thio - 2,4 - oxazolidenedione are made by reacting carbamoylmethylthiothiocarbonyl glycolic acid with N : N-diethylethylene diamine and N : N-dimethylpropylene diamine respectively: ethylisocyanate is reacted with N : N - diethyl - ethylene diamine and N - (2 - aminoethyl) morpholine respectively to form, (5), 1 - (2 - diethylaminoethyl) - 3 - ethylurea and, (6), 1 - ethyl - 3 - (2 - morpholinoethyl) urea, which products are then condensed with malonic acid or diethyl malonate to give, (5), 1-(2-diethylaminoethyl) - 3 - ethylbarbituric acid and, (6), 1 - ethyl - 3 - (2 - morpholinoethyl) - bar - bituric acid; (8), potassium N - [(3 - dimethylamino)propyl] thiocarbamyl glycolate is made by reacting carbamoylmethylthiothiocarbonyl glycolic acid with N : N-dimethyl-1,3-propylene diamine.
GB18453/65A 1964-05-04 1965-05-03 Merocyanine dyes,photographic silver halide emulsions containing them and multilayer photographic elements Expired GB1112034A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US364808A US3384486A (en) 1964-05-04 1964-05-04 Merocyanine dyes for photographic elements containing an extracyclic tertiary amino group

Publications (1)

Publication Number Publication Date
GB1112034A true GB1112034A (en) 1968-05-01

Family

ID=23436169

Family Applications (2)

Application Number Title Priority Date Filing Date
GB42105/66A Expired GB1112036A (en) 1964-05-04 1965-05-03 Photographic silver halide emulsions containing colour couplers and merocyanine dyes
GB18453/65A Expired GB1112034A (en) 1964-05-04 1965-05-03 Merocyanine dyes,photographic silver halide emulsions containing them and multilayer photographic elements

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB42105/66A Expired GB1112036A (en) 1964-05-04 1965-05-03 Photographic silver halide emulsions containing colour couplers and merocyanine dyes

Country Status (3)

Country Link
US (1) US3384486A (en)
DE (1) DE1290811B (en)
GB (2) GB1112036A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004063181A1 (en) * 2003-01-03 2004-07-29 Genzyme Corporation Urea derivatives and their use as anti-inflammatory agents
CN107964081A (en) * 2017-12-06 2018-04-27 万华化学集团股份有限公司 One kind is low to distribute response type tertiary amine catalyst and its preparation method and application

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3519430A (en) * 1967-05-29 1970-07-07 Eastman Kodak Co Photographic silver halide emulsions and elements containing merocyanine sensitizing dyes
BE755812A (en) * 1969-09-05 1971-02-15 Fuji Photo Film Co Ltd MULTI-LAYER PHOTOSENSITIVE MATERIALS FOR COLOR PHOTOGRAPHY
US3718476A (en) * 1970-10-23 1973-02-27 Eastman Kodak Co Silver halide element containing merocyanine dyes with a 3-pyrrolinylalkyl group
US3880843A (en) * 1970-10-23 1975-04-29 Eastman Kodak Co Merocyanine dyes
FR2128737B1 (en) * 1971-03-09 1978-03-03 Minnesota Mining & Mfg
US3880844A (en) * 1972-03-13 1975-04-29 Eastman Kodak Co Photographic sensitizing dyes containing a bridgehead nitrogen
JPS5225333B1 (en) * 1974-04-19 1977-07-07
JPS59214030A (en) * 1983-05-19 1984-12-03 Fuji Photo Film Co Ltd Silver halide photographic emulsion
JP2520763B2 (en) * 1990-04-20 1996-07-31 富士写真フイルム株式会社 Water-soluble methine compound and silver halide photographic emulsion containing the compound
US5679795A (en) * 1995-02-28 1997-10-21 Eastman Kodak Company Method of synthesizing dyes and precursor compounds therefor
US5563021A (en) * 1995-03-31 1996-10-08 Eastman Kodak Company Photographic elements with tetra-nuclear merocyanine sensitizers

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2078233A (en) * 1934-09-14 1937-04-27 Eastman Kodak Co Photographic emulsion
US2170805A (en) * 1937-04-24 1939-08-29 Eastman Kodak Co Photographic emulsion containing dyes from benzoxazoles
US2282116A (en) * 1939-04-14 1942-05-05 Eastman Kodak Co Photographic element
US2454629A (en) * 1940-01-27 1948-11-23 Eastman Kodak Co Polymethine dyes
BE551713A (en) * 1955-10-12

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004063181A1 (en) * 2003-01-03 2004-07-29 Genzyme Corporation Urea derivatives and their use as anti-inflammatory agents
US7186725B2 (en) 2003-01-03 2007-03-06 Genzyme Corporation Anti-inflammatory compositions and methods
CN107964081A (en) * 2017-12-06 2018-04-27 万华化学集团股份有限公司 One kind is low to distribute response type tertiary amine catalyst and its preparation method and application

Also Published As

Publication number Publication date
GB1112036A (en) 1968-05-01
US3384486A (en) 1968-05-21
DE1290811B (en) 1969-03-13

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