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US4123281A
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Photographic silver halide color material containing fast-acting hardener and 2-pyrazolin-5-one coupler precursors
Assignee: Agfa Gevaert NV
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Filing: 1976-08-17
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Granted: 1978-10-31
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Expires: 1996-08-17
Abstract
Abstract Color photographic material containing a fast-acting hardener, which acts by activating carboxyl groups, wherein said material contains a 2-pyrazolin-5-one coupler precursor corresponding to one of the following general formulae I or II: ##STR1## wherein EACH OF R 1 , R and Y are substituents of the type used in 2-pyrazolin-5-one color couplers, and Z represents acyl, alkoxycarbonyl, aryloxycarbonyl, Or ##STR2## in which R 1 , R, and Y have the above-defined significance, and A represents an alkylene group or an arylene group.
Inventors
- 👤 Marcel J. Monbaliu
- 👤 Hans-Heinrich Credner
- 👤 Wolfgang Himmelmann
- 👤 Ernst Meier
- 👤 Gaston J. Benoy
- 👤 Raphael K. Van Poucke
- 👤 Karl-Wilhelm Schranz
- 👤 George F. Van Veelen
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 09:50
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/06; C07D213/16; C07D213/20; C07D213/24; C07D213/28; C07D213/30; C07D213/32; C07D213/34; C07D213/36; C07D213/40; C07D213/60; C07D213/62; C07D213/70; C07D213/71; C07D213/72; C07D213/75; C07D213/78; C07D213/81; C07D213/82; C07D213/89; C07D215/00; C07D215/02; C07D215/16; C07D215/20; C07D215/22; C07D215/24; C07D215/26; C07D215/36; C07D217/00; C07D217/02; C07D217/10; C07D231/00; C07D231/02; C07D231/10; C07D231/12; C07D231/14; C07D231/44; C07D233/00; C07D233/54; C07D233/56; C07D249/00; C07D249/02; C07D249/08; C07D277/00; C07D277/02; C07D277/20; C07D277/22; G; G03; G03C; G03C7/00; G03C7/30; G03C7/32; G03C7/36; G03C7/38; G03C7/384; Y; Y10; Y10S; Y10S430/00; Y10S430/156
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
159 words
Colour photographic silver halide material containing a fast-acting hardener selected from the group consisting of carbodiimides, dihydroquinolines, carbamoyl pyridiniums and carbamoyloxy pyridiniums wherein said material contains a 2-pyrazolin-5-one coupler precursor corresponding to one of the following general formulae I or II: ##STR90## in which R 1 represents an alkyl group or an aryl group, R represents an alkyl group, an aryl group, an anilino group, or an acylamino group derived from a carboxylic or sulphonic acid, Y represents hydrogen, a group that can be split off during the colour development for the formation of colour-forming coloured or colourless 2-pyrazolin-5-one couplers, or a group that cannot be split off for the formation of 2-pyrazolin-5-one competing coupler, and Z represents an acyl group deriving from an organic carboxylic acid, an alkoxy-carbonyl group, an aryloxycarbonyl group, or the group ##STR91## in which R 1 , R, and Y have the above-defined significance, and A represents an alkylene group or an arylene group.
Claim 2
Dependent Claim
159 words
Colour photographic silver halide material containing a fast-acting hardener selected from the group consisting of carbodiimides, dihydroquinolines, carbamoyl pyridiniums and carbamoyloxy pyridiniums wherein said material contains a 2-pyrazolin-5-one coupler precursor corresponding to one of the following general formulae I or II: ##STR90## in which R 1 represents an alkyl group or an aryl group, R represents an alkyl group, an aryl group, an anilino group, or an acylamino group derived from a carboxylic or sulphonic acid, Y represents hydrogen, a group that can be split off during the colour development for the formation of colour-forming coloured or colourless 2-pyrazolin-5-one couplers, or a group that cannot be split off for the formation of 2-pyrazolin-5-one competing coupler, and Z represents an acyl group deriving from an organic carboxylic acid, an alkoxy-carbonyl group, an aryloxycarbonyl group, or the group ##STR91## in which R 1 , R, and Y have the above-defined significance, and A represents an alkylene group or an arylene group.
Claim 3
Dependent Claim
29 words
Colour photographic material according to claim 1, wherein the 2-pyrazolin-5-one coupler precursor corresponds to formulae I or II, in which R represents an anilino group or a carboxylic acylamino.
Claim 4
Dependent Claim
288 words
Colour photographic material according to claim 1, wherein the fast-acting hardener is a carbamoyl pyridinium hardener corresponding to the following formula: ##STR92## in which R 2 represents an alkyl, aryl, or aralkyl group R 3 represents (1) an alkyl, aryl, or aralkyl group, and the same meaning as R 2 , or (2) an alkyl, aryl, aralkyl, or alkylarylalkyl group substituted with a further carbamoylammonium group of the following formula: ##STR93## or R 2 and R 3 together represent the atoms required to complete a heterocyclic ring, R 4 represents hydrogen, alkyl, or the group --A--.sub.α, in which A represents a vinyl group of a polymerizable vinyl compound or of a copolymer with other copolymerizable monomers and α represents a number such that the molecular weight of the compound is greater than 1000, R 5 hydrogen or alkyl or, when Z denotes the atomic group required for completing a pyridinium ring and R 4 is absent, R 5 denotes a formylamino, acylamino, or ureido group, an alkyl group substituted with acylamino or ureido groups, an amido group, or alkyl, which is substituted with an amido group, a straight chain or branched chain alkyl substituted with hydroxyl, alkyl, formyloxy, acyloxy or a carbamoyloxy, a straight chain or branched chain alkyl substituted with an amino, alkylamino, formylamino, acylamino, or ureido group, R 6 represents alkyl, aryl, or aralkyl, but R 6 is absent, if the nitrogen atom, to which R 6 is attached, carries a double bond in the heterocyclic aromatic ring formed by Z, Z represents the group of atoms required for completing a 5-membered or 6membered heterocyclic aromatic ring, including a condensed ring system, which group may include 1 or more additional heteroatoms, and X represents an anion.
Claim 5
Dependent Claim
116 words
Colour photographic material according to claim 1, wherein the hardener is a carbamoyl pyridinium hardener corresponding to the following general formula: ##STR94## in which R 23 represents an alkyl, aryl, or aralkyl group, R 24 represents (1) an alkyl, aryl, or aralkyl group, and the same meaning as R 23 or (2) an alkyl, aryl, aralkyl, or alkylarylalkyl group substituted with a further carbamoylammonium group of the following formula ##STR95## or R 23 and R 24 together represent the atoms required to complete a heterocyclic ring R 25 represents hydrogen, methyl, or ethyl, R 26 represents methylene, ethylene, propylene, or a simple chemical bond, Me + represents an alkali metal cation, X - represents an anion.
Claim 6
Dependent Claim
221 words
Colour photographic material according to claim 1, wherein the hardener is a carbamoyl pyridinium hardener corresponding to the following general formula: ##STR96## in which R 2 represents an alkyl, aryl, or aralkyl group, R 3 represents (1) an alkyl, aryl, or aralkyl group, and the same meaning as R 2 , or (2) an alkyl, aryl, aralkyl, or alkylarylalkyl group substituted with a further carbamoylammonium group of the following formula: ##STR97## or R 2 and R 3 together represent the atoms required to complete a heterocyclic ring, X represents an anion, R 5 represents hydrogen or one of the following groups: ______________________________________
NR.sup.7COR.sup.8
R.sup.7 = H, Alkyl (C.sub.1C.sub.4)
R.sup.8 = H, Alkyl (C.sub.1C.sub.4), NR.sup.9 R.sup.10
R.sup.9,R.sup.10 = (similar or different) H, Alkyl
(C.sub.1C.sub.4)
(CH.sub.2).sub.mNR.sup.11 R.sup.12
R.sup.11 = COR.sup.13
R.sup.12 = H, Alkyl (C.sub.1C.sub.4)
R.sup.13 = H, Alkyl (C.sub.1C.sub.4), NR.sup.14 R.sup.15
R.sup.14 = Alkyl (C.sub.1C.sub.4), Aryl
R.sup.15 = H, Alkyl, Aryl
m = 1-3
(CH.sub.2).sub.nCONR.sup.16 R.sup.17
R.sup.16 = H, Alkyl (C.sub.1C.sub.4), Aryl
R.sup.17 = H, Alkyl (C.sub.1C.sub.4) or
R.sup.16 and R.sup.17 together represent the
atoms required to complete a
5-membered or
6-membered aliphatic ring
n = 0-3
##STR98## R.sup.18 = H, Alkyl (C.sub.1C.sub.4), which may
be substituted by halogen Y = O, NR.sup.20 R.sup.19 = H,
Alkyl, COR.sup.21, CONHR.sup.22 R.sup.20, R.sup.21,
R.sup.22 = (similar or different) H, Alkyl (C.sub.1C.sub.4)
= 2-3
______________________________________
Claim 7
Dependent Claim
133 words
Colour photographic material according to claim 1, wherein the hardener is a carbamoyl oxypyridinium hardener corresponding to the general formula: ##STR99## in which R 27 represents alkyl or aryl R 28 represents alkyl or the group ##STR100## R 31 represents hydrogen or alkyl, and R 32 represents alkyl, R 27 and R 28 together represent the atoms required to complete a heterocyclic ring system e.g. a pyrrolidine, morpholine, piperidine, perhydroazepine, 1,2,3,4,-tetrahydroquinoline, or imidazoline-2-OH ring, or R 27 and R 28 together represent the atoms required to complete a piperazine ring, in which the second nitrogen atom establishes the connection to a second similar molecular grouping corresponding to the general formulae, R 29 represents hydrogen halogen, alkyl, oxyalkyl, cyano, --CONH 2 , or --NH-CO-O-alkyl, R 30 represents hydrogen or alkyl, X represents an anion.
Claim 8
Dependent Claim
116 words
Colour photographic material according to claim 1, wherein the hardener is a carbodiimide hardener corresponding to the following general formula: R.sup.31 --N═C═N-R.sup.32 in which: R 31 and R 32 represents (similar or different) alkyl, alkoxyalkyl, an aryl group or a 5-membered heterocyclic ring, or R 31 represents alkyl having 1 to 5 carbon atoms, and R 32 represents the group ##STR101## in which R 33 represents alkyl having 1 to 5 carbon atoms, R 34 and R 35 represent alkyl having 1 to 3 carbon atoms, or R 34 and R 35 together represent a 6-membered heterocyclic ring having 1 to 2 hetero atoms, R 36 represents hydrogen or lower alkyl, and X represents an anion.
Claim 9
Dependent Claim
63 words
Colour photographic material according to claim 1, wherein the hardener is a dihydroquinoline hardener corresponding to one of the following general formulae: ##STR102## in which R 37 represents an alkyl group, R 38 represents an alkyl or aralkyl group, or if R 39 represents hydrogen, the group ##STR103## R 39 represents hydrogen, halogen, alkyl, or alkoxy, and R 40 represents an alkyl group.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-10-30 | 1982-05-01 | 1982-10-31 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-10-30 | 1986-05-01 | 1986-10-31 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-10-30 | 1990-05-01 | 1990-10-31 | $7700.00 | Window Closed / Lapsed |