US2993791A - Color couplers containing long chain alkylaminoisophthalicester groups - Google Patents

Color couplers containing long chain alkylaminoisophthalicester groups Download PDF

Info

Publication number: US2993791A
Authority: US; United States
Prior art keywords: color; groups; compound; potassium; sodium
Prior art date: 1957-10-31
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 - Lifetime

Application number

US693509A

Other languages

English (en)

Inventor

Robert F Coles

Schulze Heinz

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.)

GAF Chemicals Corp

Original Assignee

General Aniline and Film Corp

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.)

1957-10-31

Filing date

1957-10-31

Publication date

1961-07-25

1957-10-31 Application filed by General Aniline and Film Corp filed Critical General Aniline and Film Corp

1957-10-31 Priority to US693509A priority Critical patent/US2993791A/en

1958-10-15 Priority to GB32973/58A priority patent/GB857213A/en

1958-10-30 Priority to DE1958G0025600 priority patent/DE1073308B/de

1960-10-19 Priority to BE596163A priority patent/BE596163Q/fr

1961-07-25 Application granted granted Critical

1961-07-25 Publication of US2993791A publication Critical patent/US2993791A/en

1978-07-25 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims description 26
239000000839 emulsion Substances 0.000 claims description 23
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
-1 ketomethylene Chemical group 0.000 description 19
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 17
150000003839 salts Chemical class 0.000 description 17
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 15
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 15
229910052700 potassium Inorganic materials 0.000 description 15
239000011591 potassium Substances 0.000 description 15
229910052708 sodium Inorganic materials 0.000 description 15
239000011734 sodium Substances 0.000 description 15
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 14
239000000047 product Substances 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
239000003795 chemical substances by application Substances 0.000 description 9
125000000217 alkyl group Chemical group 0.000 description 8
229910052739 hydrogen Inorganic materials 0.000 description 8
239000003208 petroleum Substances 0.000 description 6
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
150000002431 hydrogen Chemical class 0.000 description 5
239000001257 hydrogen Substances 0.000 description 5
239000000203 mixture Substances 0.000 description 5
230000003647 oxidation Effects 0.000 description 5
238000007254 oxidation reaction Methods 0.000 description 5
238000010992 reflux Methods 0.000 description 5
239000007787 solid Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
239000008096 xylene Substances 0.000 description 5
WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 4
108010010803 Gelatin Proteins 0.000 description 4
239000002253 acid Substances 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
230000008878 coupling Effects 0.000 description 4
238000010168 coupling process Methods 0.000 description 4
238000005859 coupling reaction Methods 0.000 description 4
229920000159 gelatin Polymers 0.000 description 4
239000008273 gelatin Substances 0.000 description 4
235000019322 gelatine Nutrition 0.000 description 4
235000011852 gelatine desserts Nutrition 0.000 description 4
238000000034 method Methods 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
239000003610 charcoal Substances 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
239000006185 dispersion Substances 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 3
229910003446 platinum oxide Inorganic materials 0.000 description 3
229910052709 silver Inorganic materials 0.000 description 3
239000004332 silver Substances 0.000 description 3
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000003513 alkali Substances 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
239000007859 condensation product Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
QQVIHTHCMHWDBS-UHFFFAOYSA-L isophthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC(C([O-])=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-L 0.000 description 2
150000002790 naphthalenes Chemical class 0.000 description 2
150000002828 nitro derivatives Chemical class 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 2
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
125000000542 sulfonic acid group Chemical group 0.000 description 2
CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
MWWNNNAOGWPTQY-UHFFFAOYSA-N 3-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=CC(S(Cl)(=O)=O)=C1 MWWNNNAOGWPTQY-UHFFFAOYSA-N 0.000 description 1
NXTNASSYJUXJDV-UHFFFAOYSA-N 3-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC(C(Cl)=O)=C1 NXTNASSYJUXJDV-UHFFFAOYSA-N 0.000 description 1
XBTWVJKPQPQTDW-UHFFFAOYSA-N 4-n,4-n-diethyl-2-methylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C(C)=C1 XBTWVJKPQPQTDW-UHFFFAOYSA-N 0.000 description 1
QNGVNLMMEQUVQK-UHFFFAOYSA-N 4-n,4-n-diethylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C=C1 QNGVNLMMEQUVQK-UHFFFAOYSA-N 0.000 description 1
SKIBELYSXFYZPS-UHFFFAOYSA-N 4-n-ethylbenzene-1,4-diamine Chemical compound CCNC1=CC=C(N)C=C1 SKIBELYSXFYZPS-UHFFFAOYSA-N 0.000 description 1
JXRGUPLJCCDGKG-UHFFFAOYSA-N 4-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=C(S(Cl)(=O)=O)C=C1 JXRGUPLJCCDGKG-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
GKKZMYDNDDMXSE-UHFFFAOYSA-N Ethyl 3-oxo-3-phenylpropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CC=C1 GKKZMYDNDDMXSE-UHFFFAOYSA-N 0.000 description 1
BZORFPDSXLZWJF-UHFFFAOYSA-N N,N-dimethyl-1,4-phenylenediamine Chemical compound CN(C)C1=CC=C(N)C=C1 BZORFPDSXLZWJF-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
238000013019 agitation Methods 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000002585 base Substances 0.000 description 1
238000004061 bleaching Methods 0.000 description 1
238000009835 boiling Methods 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000004799 bromophenyl group Chemical group 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
125000002843 carboxylic acid group Chemical group 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000012320 chlorinating reagent Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000000068 chlorophenyl group Chemical group 0.000 description 1
239000000084 colloidal system Substances 0.000 description 1
229940125773 compound 10 Drugs 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 1
150000005690 diesters Chemical class 0.000 description 1
238000009792 diffusion process Methods 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
125000005059 halophenyl group Chemical group 0.000 description 1
239000012943 hotmelt Substances 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000006606 n-butoxy group Chemical group 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000004780 naphthols Chemical class 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
QHDYIMWKSCJTIM-UHFFFAOYSA-N phenyl 1-hydroxynaphthalene-2-carboxylate Chemical compound C1=CC2=CC=CC=C2C(O)=C1C(=O)OC1=CC=CC=C1 QHDYIMWKSCJTIM-UHFFFAOYSA-N 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
150000004986 phenylenediamines Chemical class 0.000 description 1
HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000009877 rendering Methods 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
125000001874 trioxidanyl group Chemical group [*]OOO[H] 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- 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
- G03C7/32—Colour coupling substances
- G03C7/3212—Couplers characterised by a group not in coupling site, e.g. ballast group, as far as the coupling rest is not specific
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/006—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length of peptides containing derivatised side chain amino acids

Definitions

the use in color photography of color-forming compounds, which react with the oxidation or development product of primary aromatic amino developing agents to form colored images upon photographic development, is well-known.
the colored compound thus formed is deposited next to the silver grains of the silver image during development.
the coupler compounds as employed above may be added to the color developer solutions or they may be incorporated in the gelatino silver-halide emulsion.
the couplers When used in photographic emulsions, the couplers may be dissolved directly in the gelatin or other hydrophilic colloid. In such case, the couplers must have groups rendering them alkali soluble such as carboxylic acid or sulfonic acid groups.
the couplers may be incorporated in a photographic emulsion by dissolving them in a waterimmiscible or oily organic solvent and dispersing the resulting solutions in the photographic emulsion.
couplers of high purity particularly couplers containing carboxylic or sulfonic acid groups.
problems are experienced in obtaining couplers of sufficient solubility in organic solvents.
couplers have a tendency to diffuse in the medium in which they are incorporated.
many of the couplers mentioned in the prior art give rise to colored photographic images of undesirable spectral characteristics.
a further object is to provide color formers which containing the functional or reactive group which reacts with the oxidation products of the primary amino aromatic developing agents to yield color images, said reactive groups comprising a reactive methylene group, such as ketomethylene, i.e., COCH CO;
CIJH C C e.g., phenols and naphthols, which are reactive in the ortho or para position relative to the hydroxyl group;
X represents a CO- or SO group;
Z represents hydrogen, halogen, e.g., chlorine, bromine and iodine, an
H 1 it i Q --ONOO @omom alkyl group, e.g., methyl, ethyl, n-propyl, n-butyl, isobutyl, n-amyl, n-hexyl, etc., an aryl group, e.g., phenyl, halophenyl, e.g., chlorophenyl, bromophenyl, etc., naphthyl, etc., an alkoxyl group, e.g., methoxy, ethoxy, npropoxy, n-butoxy, etc.; R and R are short chain alkyl groups such as methyl or ethyl and Alk is an alkyl group of at least 10 carbon atom, i.e., decyl, dodecyl, tetradecyl, octadecyl, etc.
I COiCH soluble salts i.e., sodium, potassium, ammonium, etc.
a still further object is to provide color couplers which are fast to diffusion in the emulsion.
A-CONH X-III-Alk wherein A represents that part of the coupler molecule CO2CH3 and the corresponding dicarboxylic acid and its watersoluble salts, i.e., sodium, potassium, ammonium, etc.
CO2CHa and the corresponding dicarboxylic acid and its watersoluble salts i.e., sodium, potassium, ammonium, etc.
dicarboxylic acid and its watersoluble salts i.e., sodium, potassium, ammonium, etc.
dicarboxylic acid and its watersoluble salts i.e., sodium, potassium, ammonium, etc.
dicarboxylic acid and its watersoluble salts i.e., sodium, potassium, ammonium, etc.
H GIEHM H GIEHM and the corresponding dicarboxylic acid and its watersoluble salts, i.e., sodium, potassium, ammonium, etc.
dicarboxylic acid and its watersoluble salts i.e., sodium, potassium, ammonium, etc.
esters are employed, they are dissolved in a suitable solvent such as a mixture of 50 parts phenethyl alcohol, 40 parts of tricresyl phosphate and 10 parts of n-butyl phthalate and the resulting solution incorporated in the emulsion as a fine dispersion. If the acids are employed, they are 5 introduced into the emulsion directly as an alkali metal salt such as the sodium salt.
Example 1 Compound (1) is prepared as follows: Dlmethyl 5-(3-nltro-N-octadecylbenzamtdo)tsophthalate C O O OH: (lliaHw Q II I N02 COUCH-a Dlmethyl B-amtno-N-octadecylbenzamido) tsophthalate C 0 O CH:
Example II Compound (2) was prepared in the same way as Compound (1) while substituting the isomeric p-nitrobenzoy-l chloride for the m-nitrobenzoyl chloride.
Example III I Compound (3) was prepared as follows:
the 4-ch-loro-3-nitrobenzenesulfonyl chloride used above was prepared from the potassium salt of the con-responding acid using phosphorous pentachloride as the chlorinating agent and phosphorous oxychloride as a solvent.
the residual oil was crystallized from about 1200 ml. of petroleum ether; B.P. -100 C.
the resulting product was digested with 1 liter of boiling methanol, cooled and filtered. Yield g., M.P. 93-94 C.
Example VII Compound (11) was prepared by condensing dimethyl 5-(3 aminophenyl-N-octadeeylsulfonamido) isophthalate (10 g., 0.016 mole) with ethyl benzoylacetate (3.8 g., 0.02 mole) in 100 ml. of dry xylene, following the procedure used to prepare Compound (8).
the primary aromatic amino developing agents are generally suitable including the phenylenediamines and aminophenols.
Suitable compounds are 4-aminoaniline, 4-ethylaminoaniline, 4-dialkylaminoaniline, e.g., 4-dimethylaminoaniline, 4-diethylaminoaniline, 4-[N-(p-hydroxyethyD-N- ethyl] aminoaniline, 4 amino N-ethyl-N-(fi-methanesulfonamidoethyl)-2-methylaniline sulfate, and the like.
the above developing agents are preferably used in the form of their salts such as the hydrochloride or hydro sulfate as they are more soluble and stable than the free bases. All of these compounds have a primary amino group which enables the oxidation product of the developer to couple with the color compounds to form dye images. After removal of the silver image by bleaching and fixing in a manner well-known to the art, the color image remains in the emulsion.
a suitable developing solution can be prepared as follows:
the exposed silver-halide emulsions containing the color formers are developed in the above solution in the usual manner.
A-CONH ROOC COOR wherein A is an organic color forming residue of the type capable of color coupling with the oxidation products of a primary aromatic amino silver halide developing agent, said color forming residue having a grouping selected from the class consisting of a l-hydroxy-Z-phenyl group, 1-hydroxy-2-naphthyl group and a benzoylmethylene group;
X is selected from the class consisting of CO-- and
--SO Z is selected from the class consisting of hydrogen, halogen, lower alkyl, lower alkoxyl and an arcmatic hydrocarbon radical of the benzene and naphthalene series;
R and R are selected from the class consisting of hydrogen, lower alkyl, an alkali metal, ammonium and Alk is an alkyl group of from to 18 carbon atoms.
a silver-halide emulsion containing a coupling compound of the following formula is a silver-halide emulsion containing a coupling compound of the following formula.
A-CONH ROOC COOR' wherein A is an organic color forming residue of the type capable of color coupling with the oxidation products of a primary aromatic amino silver halide developing agent, said color forming residue having a grouping selected from the class consisting of a l-hydroxy-Z-phenyl group, l-hydroxy-Z-naphthyl group and a benzoylmethylene group;
X is selected from the class consisting of CO- and -SO Z is selected from the class consisting of hydrogen, halogen, lower alkyl, lower alkoxyl and an aromatic hydrocarbon radical of the benzene and naphthalene series;
a photographic emulsion for forming colored images comprising a gelatino silver-halide emulsion having incorporated therein a coupling compound of the following formula:
a photographic emulsion for forming colored images comprising a gelatino silver-halide emulsion hav- 1'1? 7' 12 Mg incorporated 'therein-a' coupliiagcompound o'f the fdl- RfrencesrCite-drin thezfile'of this patent lowmg formula UNITED STATES PATENTS 0 018B" fi 2,186,849 Wilmanns et a1 Jan. 9, 19,40 n 1, 2,498,466 Thompson Feb. 21, 19 50: 7 2,652,329 McCrossen et a1 Sept. 15, 1953 2,657,134 Graham et a1. Oct. 27, 1953. OOOH:

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US693509A 1957-10-31 1957-10-31 Color couplers containing long chain alkylaminoisophthalicester groups Expired - Lifetime US2993791A (en)

Priority Applications (4)

Application Number	Priority Date	Filing Date	Title
US693509A US2993791A (en)	1957-10-31	1957-10-31	Color couplers containing long chain alkylaminoisophthalicester groups
GB32973/58A GB857213A (en)	1957-10-31	1958-10-15	Color couplers containing long chain alkylamino-isophthalic-ester groups
DE1958G0025600 DE1073308B (de)	1957-10-31	1958-10-30	Verfahren zur Herstellung eines photographischen Farbbildes in einer Halogensilberemulsionsschicht mit hilfe von Farbkupplern und Farbentwicklung sowie Halogensilber-Emulsionen, die diese Farbkuppler enthalten
BE596163A BE596163Q (fr)	1957-10-31	1960-10-19	Coupleurs de couleur contenant des groupes ester alcoylaminoisophtalique à chaïne longue.

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US693509A US2993791A (en)	1957-10-31	1957-10-31	Color couplers containing long chain alkylaminoisophthalicester groups

Publications (1)

Publication Number	Publication Date
US2993791A true US2993791A (en)	1961-07-25

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Application Number	Title	Priority Date	Filing Date
US693509A Expired - Lifetime US2993791A (en)	1957-10-31	1957-10-31	Color couplers containing long chain alkylaminoisophthalicester groups

Country Status (4)

Country	Link
US (1)	US2993791A (fr)
BE (1)	BE596163Q (fr)
DE (1)	DE1073308B (fr)
GB (1)	GB857213A (fr)

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US3226230A (en) *	1960-02-12	1965-12-28	Gevaert Photo Prod Nv	Light-sensitive emulsions containing non-migratory n-substituted 1-hydroxy-2-naphthamide color couplers
US3419564A (en) *	1963-04-05	1968-12-31	Basf Ag	Production of bis(1-arylureido)-benzene-p- or m-dicarboxylic acid dialkyl esters
US4250251A (en) *	1978-07-27	1981-02-10	Eastman Kodak Company	Phenylsulfamoyl couplers, coupler compositions and photographic elements suited to forming integral sound tracks
US20060004188A1 (en) *	2000-09-29	2006-01-05	Wai-Yee Leung	Intermediates and the synthesis of modified carbocyanine dyes and their conjugates

Families Citing this family (1)

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BE621719A (fr) *	1962-01-18

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US2498466A (en) *	1946-05-09	1950-02-21	Gen Aniline & Film Corp	Phenolic color formers
US2652329A (en) *	1952-07-31	1953-09-15	Eastman Kodak Co	Color couplers containing isophthalic acid radicals
US2657134A (en) *	1951-12-05	1953-10-27	Eastman Kodak Co	Photographic emulsion with colored couplers containing isophthalic ester groups

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DE725872C (de) *	1935-08-07	1942-10-01	Ig Farbenindustrie Ag	Verfahren zur Herstellung von Halogensilberemulsionsschichten fuer farbenphotographisches Ein- oder Mehrschichtenmaterial
DE733407C (de) *	1935-08-07	1943-03-26	Ig Farbenindustrie Ag	Verfahren zur Herstellung von Halogensilberemulsionsschichten fuer Farbenphotographie
US2688544A (en) *	1952-07-31	1954-09-07	Eastman Kodak Co	Silver halide photographic emulsion containing dialkyl-5-(carboxyfatty acid amido) isophthalates

1957
- 1957-10-31 US US693509A patent/US2993791A/en not_active Expired - Lifetime
1958
- 1958-10-15 GB GB32973/58A patent/GB857213A/en not_active Expired
- 1958-10-30 DE DE1958G0025600 patent/DE1073308B/de active Pending
1960
- 1960-10-19 BE BE596163A patent/BE596163Q/fr active

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US2498466A (en) *	1946-05-09	1950-02-21	Gen Aniline & Film Corp	Phenolic color formers
US2657134A (en) *	1951-12-05	1953-10-27	Eastman Kodak Co	Photographic emulsion with colored couplers containing isophthalic ester groups
US2652329A (en) *	1952-07-31	1953-09-15	Eastman Kodak Co	Color couplers containing isophthalic acid radicals

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US3226230A (en) *	1960-02-12	1965-12-28	Gevaert Photo Prod Nv	Light-sensitive emulsions containing non-migratory n-substituted 1-hydroxy-2-naphthamide color couplers
US3419564A (en) *	1963-04-05	1968-12-31	Basf Ag	Production of bis(1-arylureido)-benzene-p- or m-dicarboxylic acid dialkyl esters
US4250251A (en) *	1978-07-27	1981-02-10	Eastman Kodak Company	Phenylsulfamoyl couplers, coupler compositions and photographic elements suited to forming integral sound tracks
US20060004188A1 (en) *	2000-09-29	2006-01-05	Wai-Yee Leung	Intermediates and the synthesis of modified carbocyanine dyes and their conjugates
US20060099638A1 (en) *	2000-09-29	2006-05-11	Wai-Yee Leung	Modified carbocyanine dyes and their conjugates
US20070178511A1 (en) *	2000-09-29	2007-08-02	Invitrogen Corporation	Modified carbocyanine dyes and their conjugates
US20070178512A1 (en) *	2000-09-29	2007-08-02	Invitrogen Corporation	Modified carbocyanine dyes and their conjugates
US20070232805A1 (en) *	2000-09-29	2007-10-04	Invitrogen Corporation	Modified carbocyanine dyes and their conjugates
US20090035810A1 (en) *	2000-09-29	2009-02-05	Invitrogen Corporation	Modified carbocyanine dyes and their conjugates
US20090035809A1 (en) *	2000-09-29	2009-02-05	Invitrogen Corporation	Modified Carbocyanine Dyes and Their Conjugates
US7566790B2 (en)	2000-09-29	2009-07-28	Life Technologies Corporation	Intermediates and the synthesis of modified carbocyanine dyes and their conjugates
US7671214B2 (en)	2000-09-29	2010-03-02	Molecular Probes, Inc.	Modified carbocyanine dyes and their conjugates
US7790893B2 (en) *	2000-09-29	2010-09-07	Life Technologies Corporation	Modified carbocyanine dyes and their conjugates
US7820824B2 (en) *	2000-09-29	2010-10-26	Life Technologies Corporation	Modified carbocyanine dyes and their conjugates
US7927830B2 (en)	2000-09-29	2011-04-19	Life Technologies Corporation	Modified carbocyanine dyes and their conjugates
US20110171678A1 (en) *	2000-09-29	2011-07-14	Life Technologies Corporation	Modified carbocyanine dyes and their conjugates
US8252932B2 (en)	2000-09-29	2012-08-28	Life Technologies Corporation	Modified carbocyanine dyes and their conjugates
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US9423323B2 (en)	2000-09-29	2016-08-23	Life Technologies Corporation	Modified carbocyanine dyes and their conjugates

Also Published As

Publication number	Publication date
GB857213A (en)	1960-12-29
DE1073308B (de)	1960-01-14
BE596163Q (fr)	1961-02-15

Publication	Publication Date	Title
US3644498A (en)	1972-02-22	Yellow dye forming couplers for color photography
US2566271A (en)	1951-08-28	Photographic developer containing substituted sulfonamide groups
US4009035A (en)	1977-02-22	Process for forming cyan dye photographic images
US2412700A (en)	1946-12-17	Thioglycolic amides
US2312040A (en)	1943-02-23	Production of colored photographic images by color development and composition therefor
US3615505A (en)	1971-10-26	Silver halide emulsion containing 2-pyrazolin-5-one color coupler
US2846307A (en)	1958-08-05	Isoxazolone couplers in color photography
US2330291A (en)	1943-09-28	Dye intermediate
US2993791A (en)	1961-07-25	Color couplers containing long chain alkylaminoisophthalicester groups
US2829975A (en)	1958-04-08	3-alpha-sulfo acylamino pyrazolone color formers in which the acyl group contains a long aliphatic chain
US2592363A (en)	1952-04-08	P-phenylenediamine developer containing nu-alkylacetamido ethyl substituent
US3222176A (en)	1965-12-07	Photographic colour images from amino substituted phenols
US3056674A (en)	1962-10-02	Color formers for producing yellow dye images by color development
US2448939A (en)	1948-09-07	Thioglycolic amide couplers
US3337344A (en)	1967-08-22	Color photographic silver halide emulsion
US2979405A (en)	1961-04-11	Light-sensitive photographic element containing a 1-hydroxy-2-naphthoic acid anilidecolor coupler
US2333106A (en)	1943-11-02	Color photography
US2269481A (en)	1942-01-13	Production of colored photographic images
US2359274A (en)	1944-09-26	Processes of color photography using azole color formers
US3676124A (en)	1972-07-11	Photographic negative material for color diffusion transfer process
US2756149A (en)	1956-07-24	Mordanting basic dyes in photography
US3135609A (en)	1964-06-02	1-hydroxy-2-naphthamide couplers for color photography
US2728660A (en)	1955-12-27	Salicylic acid ester and amide photographic coupler compounds
US2500487A (en)	1950-03-14	Yellow diffusion-fast color formers of the benzimidazole class
US3622337A (en)	1971-11-23	Cyan color formers for color photography