US2163146A - Taurides - Google Patents
Taurides Download PDFInfo
- Publication number
- US2163146A US2163146A US164500A US16450037A US2163146A US 2163146 A US2163146 A US 2163146A US 164500 A US164500 A US 164500A US 16450037 A US16450037 A US 16450037A US 2163146 A US2163146 A US 2163146A
- Authority
- US
- United States
- Prior art keywords
- anthraquinone
- taurides
- sulfomethyltauride
- tauride
- water
- 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 - Lifetime
Links
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 229940090898 Desensitizer Drugs 0.000 description 4
- POPBYCBXVLHSKO-UHFFFAOYSA-N 9,10-dioxoanthracene-1-carboxylic acid Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(=O)O POPBYCBXVLHSKO-UHFFFAOYSA-N 0.000 description 3
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 3
- 150000004056 anthraquinones Chemical class 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 235000011941 Tilia x europaea Nutrition 0.000 description 2
- 229940101006 anhydrous sodium sulfite Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000004571 lime Substances 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 229940001482 sodium sulfite Drugs 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- HDGMAACKJSBLMW-UHFFFAOYSA-N 4-amino-2-methylphenol Chemical compound CC1=CC(N)=CC=C1O HDGMAACKJSBLMW-UHFFFAOYSA-N 0.000 description 1
- ZVNPWFOVUDMGRP-UHFFFAOYSA-N 4-methylaminophenol sulfate Chemical compound OS(O)(=O)=O.CNC1=CC=C(O)C=C1.CNC1=CC=C(O)C=C1 ZVNPWFOVUDMGRP-UHFFFAOYSA-N 0.000 description 1
- JAJIPIAHCFBEPI-UHFFFAOYSA-N 9,10-dioxoanthracene-1-sulfonic acid Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)O JAJIPIAHCFBEPI-UHFFFAOYSA-N 0.000 description 1
- YYVYAPXYZVYDHN-UHFFFAOYSA-N 9,10-phenanthroquinone Chemical compound C1=CC=C2C(=O)C(=O)C3=CC=CC=C3C2=C1 YYVYAPXYZVYDHN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical compound CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
Definitions
- Thisinvention is based' on the observation that the taurides of anthraquinone-carboxylic acids and sulfonic acids have a pronounced desensitizing capacity and are free from the foregoing objections. Their desensitizing effect exceeds considerably that of the hitherto known best desensitizer, namely pinacryptol green.
- the taurides do not form sparingly soluble lime salts and are colorless. Owing to the combination of these favorable properties, the taurides may be regarded 5 as ideal desensitizers. They may be used either in a preliminary bath or as an addition to the developer. Where a preliminary bath is used its desensitizing effect may be considerably enhanced by addition of sodium sulfite.
- Suitable compounds are for instance anthraquinone-sulfotauride, anthraquinone-l-sulfomethyl-tauride, anthraquinone-Z-sulfomethyltauride, anthraquinone-Z-chloro-3-sulfomethyl-tauride, anthraquinone-2, G-disulfomethyl-tauride, anthraquinone-2-carbonylmethyltauride and anthraquinone-2-chloro-3-carbonyl-methyltauride.
- methyltauride salt may be produced as follows (parts being by weight) 2 To 30 parts of anthraquinone-l sulfochloride' -.5 (obtainable by condensing potassium antharqulnone-l-sulfonate with phosphorus pentachloride) mixed with 300 parts of water there are added 30 parts of methyltaurine. The whole is heated at about C. with stirring until the chloride 10 is completely dissolved, and filteredif necessary. To the solution sodium chloride isadded whereby the sodium salt of anthraquinone-l-sulfomethyltauride is precipitated.
- the development may be first for 1 minute in the dark and then continued in a bright green 35 or yellow light.
- An anthraquinone tauride corresponding with the general formula X stands for a member of the group consisting of CO and S02; Y stands for a member of the group consisting of H and alkyl.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Patented June 20, 1939 UNITED STATES PATENT F F'lCE 'TAURIDES of Delaware No Drawing.
Original application October '7,
1936, Serial .No. 104,442, Patent No. 2,131,742. Divided and this application September 18, 1937, Serial'No. 164,500. In Germany October 11,
Our present invention relates to taurides. This application is a division of our application Ser. No. 104,442, filed October 7, 1936, now Patent No. 2,131,742.
.5 One ofits objects isto provide a tauride of a compound selected from the group consisting of anthraquinone carboxylic acids and anthraquinone sulfonic acids. Another object are new desensitizers. Further objects will be seen from the detailed specification following hereafter.
It has been proposed to use water-soluble derivatives of anthraquinone or phenanthrenequinone, particularly anthraquinone carboxylic acids and-anthraquinone sulfonic acids for desensitiz- 1'15 ing light-sensitive, particularly panchromatic, silpinacryptol green. Some of the said compounds are also open to the objection that they form precipitates in water containing lime compounds, and others that they are colored. Both of these properties -are undesirable in a desensitizer.
Thisinvention is based' on the observation that the taurides of anthraquinone-carboxylic acids and sulfonic acids have a pronounced desensitizing capacity and are free from the foregoing objections. Their desensitizing effect exceeds considerably that of the hitherto known best desensitizer, namely pinacryptol green. The taurides do not form sparingly soluble lime salts and are colorless. Owing to the combination of these favorable properties, the taurides may be regarded 5 as ideal desensitizers. They may be used either in a preliminary bath or as an addition to the developer. Where a preliminary bath is used its desensitizing effect may be considerably enhanced by addition of sodium sulfite. Corre- 40 spondingly when used in the developer their eifect is the stronger the more sodium sulfite the developer contains. Suitable compounds are for instance anthraquinone-sulfotauride, anthraquinone-l-sulfomethyl-tauride, anthraquinone-Z-sulfomethyltauride, anthraquinone-Z-chloro-3-sulfomethyl-tauride, anthraquinone-2, G-disulfomethyl-tauride, anthraquinone-2-carbonylmethyltauride and anthraquinone-2-chloro-3-carbonyl-methyltauride.
The following examples illustrate the invention:
1. 1 gram of the sodium salt of anthraquinone- 1-sulfo-methyltauride is dissolved in 1 litre of water and in this solution orthochromatic or panchromatic photographic layers are bathed for 2 5 Claims. (01. 2 0-371) minutes. Development may then follow, for example in a bright green light. The methyltauride salt may be produced as follows (parts being by weight) 2 To 30 parts of anthraquinone-l sulfochloride' -.5 (obtainable by condensing potassium antharqulnone-l-sulfonate with phosphorus pentachloride) mixed with 300 parts of water there are added 30 parts of methyltaurine. The whole is heated at about C. with stirring until the chloride 10 is completely dissolved, and filteredif necessary. To the solution sodium chloride isadded whereby the sodium salt of anthraquinone-l-sulfomethyltauride is precipitated.
2. 1 gram of the soduim salt of anthraquinonez-sulfo-methyltauride obtained in an analogous manner to that described in Example 1, the-parent material being anthraquinone 2-sulfochloride, is dissolved in 1 litre of water, together with '25 gramsof anhydrous sodiumsulfite. In this solution photographic layers are bathed for 2 minutes and may then be developed inabrightgreen light.
3. Orthochromati'c and panchromatic photographic layers --are developed in one litre of a developer of the following composition: Water litre 1 Metol (mono-methyl-p-aminophenol) grams 8 Anhydrous sodium sulfite do Anhydrous sodium carbonate do 5.8 30 Potassium bromide do 2. 5 The sodium salt of anthraquinone-Z-sulfomethyltauride do 0.5
The development may be first for 1 minute in the dark and then continued in a bright green 35 or yellow light.
The simplest compounds of the class of substances to which the invention relates may be represented by the following formulae:
(c) Anthraquinone-2-sulfomethyltauride s OrIfi-OHrCHr-SOsH (d) Anthraquinone-2-carbonylmethyltauride O II C ON-CHzCH2SOaH (e) Anthraquinone-2-ch1oro-3-sulfomethyltauride acids in which the nucleus is substituted by halogen.
2. An anthraquinone tauride corresponding with the general formula X stands for a member of the group consisting of CO and S02; Y stands for a member of the group consisting of H and alkyl.
3. Anthraquinone-2-carbonylmethyltauride corresponding with the formula 4. Anthraquinone-2-sulfomethy1tauride corresponding with the formula 5. Anthraquinone-Z-chloro-3-sulfomethyltauride corresponding with the formula KARL KUMETAT. SEBASTIAN GASSNER.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US164500A US2163146A (en) | 1936-10-07 | 1937-09-18 | Taurides |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US104442A US2131742A (en) | 1935-10-11 | 1936-10-07 | Photographic desensitizing |
| US164500A US2163146A (en) | 1936-10-07 | 1937-09-18 | Taurides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2163146A true US2163146A (en) | 1939-06-20 |
Family
ID=26801546
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US164500A Expired - Lifetime US2163146A (en) | 1936-10-07 | 1937-09-18 | Taurides |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2163146A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3179663A (en) * | 1961-05-26 | 1965-04-20 | Ciba Ltd | New sulfuric acid leuco esters |
| US4276224A (en) * | 1978-06-07 | 1981-06-30 | Ciba-Geigy Corporation | Anthraquinone sulphonamide compounds and preparation |
-
1937
- 1937-09-18 US US164500A patent/US2163146A/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3179663A (en) * | 1961-05-26 | 1965-04-20 | Ciba Ltd | New sulfuric acid leuco esters |
| US4276224A (en) * | 1978-06-07 | 1981-06-30 | Ciba-Geigy Corporation | Anthraquinone sulphonamide compounds and preparation |
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