GB1469696A - Diffusionfast couplers for colour photographic materials with light stability - Google Patents
Diffusionfast couplers for colour photographic materials with light stabilityInfo
- Publication number
- GB1469696A GB1469696A GB2173874A GB2173874A GB1469696A GB 1469696 A GB1469696 A GB 1469696A GB 2173874 A GB2173874 A GB 2173874A GB 2173874 A GB2173874 A GB 2173874A GB 1469696 A GB1469696 A GB 1469696A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pyrazolone
- group
- couplers
- preparation
- reacted
- 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
Links
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 abstract 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N 1,4-Benzenediol Natural products OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000002947 alkylene group Chemical group 0.000 abstract 3
- -1 hydroquinone ethers Chemical class 0.000 abstract 3
- 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 abstract 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 abstract 2
- JAAJQSRLGAYGKZ-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalen-1-ol Chemical compound C1=CC=C2C(O)CCCC2=C1 JAAJQSRLGAYGKZ-UHFFFAOYSA-N 0.000 abstract 1
- PBLNBZIONSLZBU-UHFFFAOYSA-N 1-bromododecane Chemical compound CCCCCCCCCCCCBr PBLNBZIONSLZBU-UHFFFAOYSA-N 0.000 abstract 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 abstract 1
- RQNUGFUIGCOMFK-UHFFFAOYSA-N 2-(4-dodecoxyphenoxy)acetic acid Chemical compound CCCCCCCCCCCCOC1=CC=C(OCC(O)=O)C=C1 RQNUGFUIGCOMFK-UHFFFAOYSA-N 0.000 abstract 1
- NNNQEWUAMZEVBM-UHFFFAOYSA-N 2-(4-methoxyphenoxy)tetradecanoic acid Chemical compound CCCCCCCCCCCCC(C(O)=O)OC1=CC=C(OC)C=C1 NNNQEWUAMZEVBM-UHFFFAOYSA-N 0.000 abstract 1
- FHXJDKPJCDJBEM-UHFFFAOYSA-N 4-dodecoxyphenol Chemical compound CCCCCCCCCCCCOC1=CC=C(O)C=C1 FHXJDKPJCDJBEM-UHFFFAOYSA-N 0.000 abstract 1
- 241001479434 Agfa Species 0.000 abstract 1
- 101100188552 Arabidopsis thaliana OCT3 gene Proteins 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 125000003435 aroyl group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 230000008878 coupling Effects 0.000 abstract 1
- 238000010168 coupling process Methods 0.000 abstract 1
- 238000005859 coupling reaction Methods 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- JQQZIRFEGUUJBP-UHFFFAOYSA-N ethyl 2-bromotetradecanoate Chemical compound CCCCCCCCCCCCC(Br)C(=O)OCC JQQZIRFEGUUJBP-UHFFFAOYSA-N 0.000 abstract 1
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- LOCAIGRSOJUCTB-UHFFFAOYSA-N indazol-3-one Chemical compound C1=CC=C2C(=O)N=NC2=C1 LOCAIGRSOJUCTB-UHFFFAOYSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
- C07C59/70—Ethers of hydroxy-acetic acid, e.g. substitutes on the ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
- C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
- C07D231/26—1-Phenyl-3-methyl-5- pyrazolones, unsubstituted or substituted on the phenyl ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/28—Two oxygen or sulfur atoms
- C07D231/30—Two oxygen or sulfur atoms attached in positions 3 and 5
- C07D231/32—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
- C07D231/52—Oxygen atom in position 3 and nitrogen atom in position 5, or vice versa
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Abstract
1469696 Substituted hydroquinone ethers AGFA GEVAERT AG 16 May 1974 [19 May 1973 3 Oct 1973] 21738/74 Heading C2C [Also in Division G2] The preparation is described of colour couplers of the formula in which A represents a colour coupler group of the alkoylacetamide, aroylacetamide, phenol, naphthol, tetrahydronaphthol, indazolone or pyrazolone series which is attached to the connecting member X in a non-coupling position either directly or through a substituent; X represents -O-, -CONH-, -NHCO-, -NHCONH-, -COO or -OCONH-; R 2 represents an alkylene group in which one hydrogen atom may be substituted by an alkyl group and in the cases where R2 is attached to a magenta coupler group of the pyrazolone series through the connecting member -OCONH- the number of carbon atoms in the alkylene group is even and in the case where R 2 is attached through X to the alkoyl or aroyl moiety of a yellow alkoyl- or aroylacetamide coupler the alkylene group has the formula -CH 2 CH 2 -; R represents an alkyl or cycloalkyl group and R 1 represents hydrogen or an alkyl group. In typical examples of the preparation of magenta couplers hydroquinone and dodecyl bromide are reacted in alcohol in the presence of KOH to give 4-dodecyloxyphenol reaction of which with ethyl chloroacetate gives 4-dodecyloxyphenoxyacetic acid. The latter is converted to the acid chloride and reacted with the appropriate pyrazolone derivative to give 1 - (2,4,6 - trichlorophenyl) - 3 - [3 - (4 - dodecyloxy - phenoxyacetamido) - anilino - pyrazolone- (5). α - (4 - Methoxyphenoxy)myristic acid (from 4-methoxyphenol and α-bromomyristic acid ethyl ester) is converted to the acid chloride and reacted with the corresponding pyrazolone derivative to give 1-(2,4,6-trichlorophenyl)-3-(2- chloro - 5 - [α - (4 - methoxyphenoxy)myristoylamido]-anilino)-pyrazolone-(5). The preparation is described of analogous methods for the preparation of couplers containing pyrazolone groups and also those containing phenolic and aroylacetamido colour coupler groups at A in Formula I.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2325461A DE2325461A1 (en) | 1973-05-19 | 1973-05-19 | DIFFUSION-RESISTANT PYRAZOLONE COUPLERS FOR COLOR PHOTOGRAPHIC MATERIALS |
| DE19732349562 DE2349562A1 (en) | 1973-10-03 | 1973-10-03 | Colour-formers of hydroquinone diether series - for photographic matls., stable to light, heat, moisture, oxidn. and redn. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1469696A true GB1469696A (en) | 1977-04-06 |
Family
ID=25765178
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2173874A Expired GB1469696A (en) | 1973-05-19 | 1974-05-16 | Diffusionfast couplers for colour photographic materials with light stability |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS5020723A (en) |
| CA (1) | CA1033979A (en) |
| CH (1) | CH600387A5 (en) |
| FR (1) | FR2229998B1 (en) |
| GB (1) | GB1469696A (en) |
| IT (1) | IT1013190B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS557702A (en) * | 1978-06-01 | 1980-01-19 | Konishiroku Photo Ind Co Ltd | Silver halide color photographic material |
| DE3272352D1 (en) * | 1981-11-12 | 1986-09-04 | Agfa Gevaert Nv | Photographic elements containing ballasted compounds |
-
1974
- 1974-05-16 GB GB2173874A patent/GB1469696A/en not_active Expired
- 1974-05-17 FR FR7417377A patent/FR2229998B1/fr not_active Expired
- 1974-05-17 CH CH684274A patent/CH600387A5/xx not_active IP Right Cessation
- 1974-05-17 IT IT5106774A patent/IT1013190B/en active
- 1974-05-17 CA CA200,251A patent/CA1033979A/en not_active Expired
- 1974-05-18 JP JP5502574A patent/JPS5020723A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CA1033979A (en) | 1978-07-04 |
| IT1013190B (en) | 1977-03-30 |
| FR2229998A1 (en) | 1974-12-13 |
| CH600387A5 (en) | 1978-06-15 |
| JPS5020723A (en) | 1975-03-05 |
| FR2229998B1 (en) | 1978-09-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| 746 | Register noted 'licences of right' (sect. 46/1977) | ||
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19920516 |