GB1045183A - New phosphate esters useful as sensitizers for photographic emulsions - Google Patents
New phosphate esters useful as sensitizers for photographic emulsionsInfo
- Publication number
- GB1045183A GB1045183A GB28321/63A GB2832163A GB1045183A GB 1045183 A GB1045183 A GB 1045183A GB 28321/63 A GB28321/63 A GB 28321/63A GB 2832163 A GB2832163 A GB 2832163A GB 1045183 A GB1045183 A GB 1045183A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- glycol
- sensitizers
- reacting
- photographic emulsions
- 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
- 239000000839 emulsion Substances 0.000 title abstract 3
- 150000003014 phosphoric acid esters Chemical class 0.000 title 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 4
- 239000007859 condensation product Substances 0.000 abstract 4
- 150000004820 halides Chemical class 0.000 abstract 4
- 229920001223 polyethylene glycol Polymers 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 3
- 239000002202 Polyethylene glycol Substances 0.000 abstract 2
- 239000007788 liquid Substances 0.000 abstract 2
- 125000006353 oxyethylene group Chemical group 0.000 abstract 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- 229920000151 polyglycol Polymers 0.000 abstract 2
- 239000010695 polyglycol Substances 0.000 abstract 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 2
- 150000003512 tertiary amines Chemical class 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- 229910019213 POCl3 Inorganic materials 0.000 abstract 1
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 1
- ITVPBBDAZKBMRP-UHFFFAOYSA-N chloro-dioxido-oxo-$l^{5}-phosphane;hydron Chemical compound OP(O)(Cl)=O ITVPBBDAZKBMRP-UHFFFAOYSA-N 0.000 abstract 1
- 230000000052 comparative effect Effects 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 238000007865 diluting Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 230000003472 neutralizing effect Effects 0.000 abstract 1
- YZUUTMGDONTGTN-UHFFFAOYSA-N nonaethylene glycol Chemical class OCCOCCOCCOCCOCCOCCOCCOCCOCCO YZUUTMGDONTGTN-UHFFFAOYSA-N 0.000 abstract 1
- 229920000847 nonoxynol Polymers 0.000 abstract 1
- GLZWNFNQMJAZGY-UHFFFAOYSA-N octaethylene glycol Chemical compound OCCOCCOCCOCCOCCOCCOCCOCCO GLZWNFNQMJAZGY-UHFFFAOYSA-N 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/6574—Esters of oxyacids of phosphorus
- C07F9/65746—Esters of oxyacids of phosphorus the molecule containing more than one cyclic phosphorus atom
-
- 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
- G03C1/04—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with macromolecular additives; with layer-forming substances
- G03C1/043—Polyalkylene oxides; Polyalkylene sulfides; Polyalkylene selenides; Polyalkylene tellurides
-
- 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
- G03C5/00—Photographic processes or agents therefor; Regeneration of such processing agents
- G03C5/26—Processes using silver-salt-containing photosensitive materials or agents therefor
- G03C5/29—Development processes or agents therefor
- G03C5/305—Additives other than developers
- G03C5/3056—Macromolecular additives
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/15—Lithographic emulsion
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Polyethers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
The invention comprises condensation products having the formul <FORM:1045183/C2/1> in which R is hydrogen or a radical of the formula -(CH2-CH2-O-)nH, n is an integer of at least 3 and x is a number of at least 1, e.g. 1 to 100, preferably 1 to 10. They may be obtained by reacting compounds of the formula <FORM:1045183/C2/2> or other corresponding halides with polyglycols of the formula H-(O-CH2-CH2)n-OH if desired in a liquid alkaline medium, e.g. pyri dine, triethylamine or other tertiary amine, at 0 DEG to 80 DEG C., preferably 10 DEG to 50 DEG C. The glycol is preferably used in an amount of 1 to 2 moles per mole of the halide. Specified polyethylene glycols are tetra-, hexa-, octa- and nona-ethylene glycols and a polyethylene glycol with 34 oxyethylene units. Compounds in which R is hydrogen are obtained by hydrolysing with water an initial condensation product containing a P-Cl group. The spirocyclic pentaerythritol di(phosphoric acid monochloride) used as starting material may be obtained by reacting pentaerythritol with POCl3. The condensation products are useful as sensitizers for photographic emulsions. The compound of the formula <FORM:1045183/C2/3> in which X is 2 referred to for comparative purposes and is obtained by reacting a compound of the formula <FORM:1045183/C2/4> with octaethylene glycol in the presence of NaOCH3 and then diluting with water and neutralizing with HCl.ALSO:The invention comprises condensation products having the formula <FORM:1045183/C3/1> in which R is hydrogen or a radical of the formula -(CH2-CH2-O-)nH, n is an integer of at least 3 and x is a number of at least 1. They may be obtained by reacting compounds of the formula <FORM:1045183/C3/2> or other corresponding halides with polyglycols of the formula H-(O-CH2-CH2)n-OH and the condensation may be carried out in a liquid alkaline medium, e.g. pyridine, triethylamine or other tertiary amine, at 0 DEG to 80 DEG C., preferably 10 DEG to 50 DEG C. The degree of polymerization n of the glycol may be 3 or more, e.g. 3 to 100, preferably 4 to 50 and x may be from 1 to 100, preferably 1 to 10. The glycol is preferably used in an amount of 1 to 2 moles per mole of the halide. Specified polyethylene glycols are tetra-, hexa-, octa- and nonaethylene glycols and a polyethylene glycol with 34 oxyethylene units. The products are useful as sensitizers for photographic emulsions.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEA40784A DE1246403B (en) | 1962-07-21 | 1962-07-21 | Process for making photographic images |
| DEA43236A DE1178297B (en) | 1962-07-21 | 1963-05-31 | Process for increasing the general sensitivity of photographic silver halide emulsions and photographic materials for carrying out the process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1045183A true GB1045183A (en) | 1966-10-12 |
Family
ID=25963785
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB28321/63A Expired GB1045183A (en) | 1962-07-21 | 1963-07-17 | New phosphate esters useful as sensitizers for photographic emulsions |
| GB22523/64A Expired GB1045184A (en) | 1962-07-21 | 1964-06-01 | Sensitisation of photographic silver halide emulsions |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB22523/64A Expired GB1045184A (en) | 1962-07-21 | 1964-06-01 | Sensitisation of photographic silver halide emulsions |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US3169863A (en) |
| BE (2) | BE648588A (en) |
| CH (2) | CH433977A (en) |
| DE (2) | DE1246403B (en) |
| FR (2) | FR1364351A (en) |
| GB (2) | GB1045183A (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE635167A (en) * | 1962-07-21 | |||
| BE666066A (en) * | 1964-07-02 | 1965-12-29 | ||
| US3532501A (en) * | 1967-02-10 | 1970-10-06 | Gaf Corp | Water-soluble acid esters of polyoxyalkylenated pentaerythritol in silver halide emulsions |
| DE3264151D1 (en) * | 1981-01-20 | 1985-07-25 | Ciba Geigy Ag | Photographic recording material and process for its preparation |
| US4436811A (en) * | 1981-07-10 | 1984-03-13 | Ciba-Geigy Ag | Photographic material |
| CN100400542C (en) * | 2006-03-30 | 2008-07-09 | 上海大学 | Synthetic method for phosphate ester |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2531832A (en) * | 1947-06-12 | 1950-11-28 | Du Pont | Silver halide developers containing polyethylene glycols |
| US2974158A (en) * | 1953-04-02 | 1961-03-07 | Union Carbide Corp | Preparation of bi-heterocyclic phosphorus containing compounds |
| GB840384A (en) * | 1957-03-12 | 1960-07-06 | Ilford Ltd | Improvements in or relating to hemicyanine dyestuffs |
| US2961317A (en) * | 1958-06-19 | 1960-11-22 | Eastman Kodak Co | Holopolar dyes derived from 3-indazolinone |
| US3005007A (en) * | 1959-01-19 | 1961-10-17 | Pure Oil Co | Preparation of organophosphorus compounds from glycerol and phosphorus oxyhalides |
| DE1155901B (en) * | 1959-11-17 | 1963-10-17 | Agfa Ag | Softeners for cellulose derivatives |
| DE1122834B (en) * | 1960-07-01 | 1962-01-25 | Perutz Photowerke G M B H | Process for the partial desensitization and steepening of the gradation of halogen silver emulsions |
| BE635167A (en) * | 1962-07-21 |
-
0
- BE BE635167D patent/BE635167A/xx unknown
-
1962
- 1962-07-21 DE DEA40784A patent/DE1246403B/en active Pending
-
1963
- 1963-05-31 DE DEA43236A patent/DE1178297B/en active Pending
- 1963-06-11 US US286924A patent/US3169863A/en not_active Expired - Lifetime
- 1963-06-28 CH CH800363A patent/CH433977A/en unknown
- 1963-07-17 GB GB28321/63A patent/GB1045183A/en not_active Expired
- 1963-07-22 FR FR942158A patent/FR1364351A/en not_active Expired
-
1964
- 1964-05-19 US US368714A patent/US3385708A/en not_active Expired - Lifetime
- 1964-05-29 BE BE648588D patent/BE648588A/xx unknown
- 1964-05-29 FR FR976351A patent/FR1396860A/en not_active Expired
- 1964-05-29 CH CH703464A patent/CH450156A/en unknown
- 1964-06-01 GB GB22523/64A patent/GB1045184A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE648588A (en) | 1964-11-30 |
| US3385708A (en) | 1968-05-28 |
| US3169863A (en) | 1965-02-16 |
| GB1045184A (en) | 1966-10-12 |
| CH433977A (en) | 1967-04-15 |
| DE1246403B (en) | 1967-08-03 |
| FR1396860A (en) | 1965-04-23 |
| DE1178297B (en) | 1964-09-17 |
| CH450156A (en) | 1968-01-15 |
| FR1364351A (en) | 1964-06-19 |
| BE635167A (en) |
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