US2697100A - Alpha-acylthio-n(2-benzothiazolyl) succinimides - Google Patents
Alpha-acylthio-n(2-benzothiazolyl) succinimides Download PDFInfo
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- US2697100A US2697100A US291076A US29107652A US2697100A US 2697100 A US2697100 A US 2697100A US 291076 A US291076 A US 291076A US 29107652 A US29107652 A US 29107652A US 2697100 A US2697100 A US 2697100A
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- US
- United States
- Prior art keywords
- benzothiazole
- benzothiazolyl
- group
- acid
- anhydride
- 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.)
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- -1 2-benzothiazolyl Chemical group 0.000 title description 23
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical class O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 title description 18
- 150000001875 compounds Chemical class 0.000 claims description 34
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 40
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 40
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- 239000000839 emulsion Substances 0.000 description 13
- 239000002253 acid Substances 0.000 description 9
- 229960002317 succinimide Drugs 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 229910052709 silver Inorganic materials 0.000 description 8
- 239000004332 silver Substances 0.000 description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- 125000004429 atom Chemical group 0.000 description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
- 229910052794 bromium Inorganic materials 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 125000000623 heterocyclic group Chemical group 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 150000001339 alkali metal compounds Chemical class 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 230000015556 catabolic process Effects 0.000 description 4
- 238000006731 degradation reaction Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 4
- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical group 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229910021607 Silver chloride Inorganic materials 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- CQSAQTFRLUSYSB-UHFFFAOYSA-N 1-(1,3-benzothiazol-2-yl)pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=NC2=CC=CC=C2S1 CQSAQTFRLUSYSB-UHFFFAOYSA-N 0.000 description 1
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 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 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000003287 bathing Methods 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000011081 inoculation Methods 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
- LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical compound CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 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
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- JCBJVAJGLKENNC-UHFFFAOYSA-M potassium ethyl xanthate Chemical compound [K+].CCOC([S-])=S JCBJVAJGLKENNC-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
- G03C1/35—Antiplumming agents, i.e. antibronzing agents; Toners
- G03C1/355—Organic derivatives of bivalent sulfur, selenium or tellurium
Definitions
- This invention relates to improvements in the production of photographic images, especially images on paper supports prepared from silver halide emulsions, and to new chemical compounds.
- Silver halide images are frequently subject to image degradation during processing, that is, during development, fixing, Washing, toning, or other treatment and during the moist heat to which they are subjected on drying, as when prints are subjected to ferrow typing or hot-type glazing. This degradation of the image frequently manifests itself as plumming or bronzing of the image.
- R represents an acyl group, such as acetyl, propionyl, n-butyryl, isobutyryl, benzoyl, etc., or a thiocarbalkoxyl group, such as thiocarbomethoxyl, thiocarbethoxyl, thiocarbo-n-butoxyl, thiocarbo-n-octoxyl, etc.
- Z represents the non-metallic atoms necessary to complete a heterocyclic nucleus of the benzothiazole series, are not only effective anti-plumming agents but show no tendency to gel the emulsion and are readily soluble in organic water-miscible solvents, such as ethanol, acetone, etc.
- an object of my invention to provide a means for preventing image degradation in an exposed silver halide emulsion. Still another object is to provide new chemical compounds. Still another object is to provide methods for making these new compounds. Another object is to provide photographic silver halide emulsions containing these new compounds. Other objects will become apparent from a consideration of the following examples and description.
- Silver halide emulsions in which the carrier is solely polyvinyl alcohol or hydrolyzed cellulose acetate can be used when the compounds are incorporated in the emulsion. They should be used in amounts from 0.5 g. to 10.0 grams per unit of silver halide formed from 1000 grams of silver nitrate. The same concentration of compounds should be present in the emulsion when the compounds are added by bathing the emulsion in a solution containing them. When the emulsion layer is bathed in a solution of the compound, the solution can contain up to about 5 per cent by weight of the compound.
- R1 and R2 each represents a member selected from the group consisting of a hydrogen atom, an acetyl group and a thiocarbalkoxyl group. (e, g. thiocarbomethoxyl, thiocarbethoxyl, thiocarbo-n-butoxyl, thiocarbo-n-octoxyl, etc.) together with a carboxylic anhydride, such as acetic anhydride, propionic anhydride, n-butyric anhydride, isobutyric anhydride, benzoic anhydride, etc.
- a carboxylic anhydride such as acetic anhydride, propionic anhydride, n-butyric anhydride, isobutyric anhydride, benzoic anhydride, etc.
- the carboxylic anhydride also causes acylation in cases wherein R and R2 each represents a hydrogen atom.
- the intermediates represented by Formulas II and III above can be prepared according to the methods described in my copending applications Serial Nos. 285,301 and 285,302, both filed on April 30, 1952.
- the aromatic nucleus of the benzothiazole group represented by Z above can be substituted by various groups, such as chlorine, bromine, methoxy, ethoxy, amino, methyl, ethyl, etc.
- condensations can advantageously be carried out in thepresence of an inert solvent, such asethanol, acetone, etc.
- R3 represents an alkyl group, such as methyl, ethyl, n-propyl, n-propyl, n-butyl, isobutyl, n-octyl, etc.
- M represents an alkali metal atom, such as sodium, potassium, etc. and a sufiicient amount of acid to liberate the free acid of the said alkali metal compound.
- Acids useful for this purpose comprise acetic acid, hydrochloric acid, sulfuric acid, etc., although it is to be understood that other acids can be used, since the purpose of the acid is simply to displace the alkali metal atom of the compounds of Formula V with a hydrogen atom.
- Example l.-m-Acetylthi0-N-(Z-benzothiawlyl) succinimide II oonsoorn 2.0 g. of 2-(fi-carboxy-a-thiolpropionamido)benzothiazole and 10 cc. of acetic anhydride were boiled together until a clear solution was obtained. Slowly cc. of acetic acid were added, followed by the slow addition of 25 cc. of water. Thereupon a light brown oil was; precipitated and this was chilled overnight. The resulting hard solid was collected and washed with water. From ethyl acetate, and then ethanol, it formed flat, colorless needles, M. P. 139l40 C. The yield was 0.8 g.
- Example 1a aAcetylthio-N-(Z-benzothiazolyl) succinimide 0.1 g. of 2-(fi-carboxy-fi-thiopropionamido)benzothiazole was dissolved in 3 cc. of boiling actic anhydride, followed by addition of acetic acid as directed in Example 1. A yield of 0.7 g. of pink flakes, M. P. 139-140 C., was obtained from 2 recrystallizations from ethanol.
- Example 1b -a-Aeetylthi0-N-(Z-benzothiazolyl)- succinimide 2.8 of 2-(a-acetylthio-fi-carboxypropionamido)- benzothiazole and cc. of acetic anhydride were heated together over a free flame for two minutes. The solution was decomposed with acetic acid as described in Example 1 and the product (2.5 g.) recrystallized twice from ethanol as flat butt needles or flakes, M. P. 139 C.
- Example 1c.a-Acteylthi0-N-(Z-benzothiazolyl) succinimide This example was carired out in the same manner as described in Example 1b above, except that 10 cc. of propionic anhydride were employed instead of the 10 cc. of acetic anhydride used in that example.
- the product had M. P. 139-140 C.
- Example 1d a-Acetylthi0-N-(Z-benzothiazolyl) succinimide 3.0 g. of 2-(fl-acetylthioq8-carboxypropionamido)- benzothiazole and 10 cc. of acetic anhydride were boiled together until a clear solution was obtained and the product was treated with acetic acid and water as described in Example 1 above. A yellow oil was obtained which soon crystallized to give 1.4 g. of solid. From ethanol, it formed bufl flakes, M. P. 140 C.
- Example 1e.a-Acetylthio-N-(Z-benzothiazolyl) succinimiae 1.15 g. of N-(Z-benzothiazolyl)maleinimide, 0.4 cc. of I thioacetic acid, and 10 cc. of ethanol were refluxed for five minutes to give a clear solution. The solution was slowly cooled with inoculation to prevent boiling out. A yield of 1.5 g. of bufl flakes, M. P. 138-140 C., from ethanol was obtained.
- Example 2.a-Acetylthio-N-6-ethoxy-2 benzothiazolyl) succinimide 5.0 g. of 2-(a-acetylthio-fi-carboxypropionamido)-6- ethoxybenzothiazole and cc. of acetic anhydride were boiled together until a clear solution was obtained. On chilling, a mass of crystals separated and these were recrystallized from acetic anhydride as almost colorless prisms, M. P. ZOO-202 C. The yield was 3.4 g. Ethanlol was also found to be a satisfactory crystallization so vent.
- Example 2a --u-Acetylzhi0-N-(6-eth0xy-2-benz0thiazolyl) saccinimide 10 g. of 2-(p-acetylthio-p-carboxypropionamido)- 6-ethoxybenzothiazole was dissolved in 5 cc. of boiling acetic anhydride and the solution chilled. The product which crystallized formed almost colorless prisms, M. P. 199201 C.
- Example 2b a-Acethylthio-N-(6-ethoxy-2-benzothiazolyl succinimia'e This example was carried out in exactly the same manner described in Example 2 above, except that propionic anhydride was used instead of the acetic anhydride.
- the product had M. P. ZOO-201 C.
- Example 2c -a-Acetylthio-N-(6-eth0xy-2-benzo thiazolyl succinimia'e 0.7 g. of N-(6-ethoxy-2-benzothiazolyl)maleinimide, 0.2 cc. of thioacetic acid, and 10 cc. of acetic acid were boiled together until dissolution occurred. On chilling, 0.6 g. of bull powder was obtained, forming pink needles, M. P. 199-201 C.
- the 2-(6-ethoxy-2-benzothiazolyl)maleinimide used in the above example was prepared by boiling together 3.2 g. of Z-(B-carboxyacrylamido)-6-ethoxybenzothiazole and 10 cc. of acetic anhydride until dissolution occurred.
- Example 3a a-Tthi0carbeth0xythiol-N-(Z-benzothiazolyl) succinimide 0.4 g. of N-(Z-benzothiazolyl) maleinimide, 1.0 g. of potassium ethylxanthate, and 5 cc. of acetic acid were heated on the steam bath for two minutes, whereupon dissolution occurred. The addition of water gave a brown oil, the aqueous layer was decanted and the residue washed with water and dissolved in a little ethanol. On cooling, the product crystallized, M. P. 130l31 C.
- Example 4 --a-Thiocarbo-n-octoxythiol-N-(Z-benzathiazolyl) succinimide This compound was prepared by heating together 2-(5- carboxy-a-thiocarbo-n octoxythiopropionamido)benzothioazole and acetic anhydride. It was recrystallized from ethanol as fine, colorless needles, M. P. 101 C.
- Example 5 Example 5.a-Prop i0nylthi0-N-(Z-benzthiazolyl) succinimide 1.15 g. of N-(Z-benzthiazolyl) maleinimide, 0.5 cc. of tho propionic acid (B. P. 106-108" C. obtained by the action of H28 on propionic anhydride and catalysed by 1% acetylchloride) and 10 cc. of ethanol were refluxed for 15 minutes. The required substance oiled out then crystallised on chilling. Recrystallised from ethanol a ylc'lelg 0526.45C g. was obtained as fiat, glossy, buflE needles,
- Z represerts the non-metallic atoms necessary to complete a heterocyclic nucleus of the benzothiazole series selected from the group consisting of benzothiazole and benzothiazole having substituted thereon a radical selected from the group consisting of chlorine, bromine, methoxy, ethoxy, amino, methyl and ethyl and R represents an acyl group comprising heating a compound selected from the group consisting of those represented by the following general formulas:
- Z represents the non-metallic atoms necessary to complete a heterocyclic nucleus of the benzothiazole series selected from the group consisting of benzothiazole and benzothiazole having substituted thereon a radical selected from the group consisting of chlorine, bromine, methoxy, ethoxy, amino, methyl and ethyl, together with an anhydride of a monocarboxylic acid containing from 2 to 6 carbon atoms.
- Z represents the non-metallic atoms necessary to complete a heterocyclic nucleus of the benzothiazole series selected from the group consisting of benzothiazole and benzothiazole having substituted thereon a radical selected from the group consisting of chlorine, bromine, methoxy, ethoxy, amino, methyl and ethyl comprising heating a compound selected from those represented by the following general formula:
- Z represents the non-metallic atoms necessary to complete a heterocyclic nucleus of the benzothiazole series selected from the group consisting of benzothiazole and benzothiazole having substituted thereon a radical selected from the group consisting of chlorine, bromine, methoxy, ethoxy, amino, methyl and ethyl together with thioacetic acid.
- R3 represents an alkyl group containing from 1 to 8 carbon atoms and Z represents the non-metallic atoms necessary to complete a heterocyclic nucleus of the benzothiazole series selected from the group consisting of benzothiazole and benzothiazole having substituted thereon a radical selected from the group consisting of chlorine, bromine, methoxy, ethoxy, amino, methyl and ethyl comprising heating a compound selected from those represented by the following general formula:
- Z represents the non-metallic atoms necessary to complete a heterocyclic nucleus of the benzothiazole series selected from the group consisting of benzothiazole and benzothiazole having substituted thereon a radical selected from the group consisting of chlorine, bromine, methoxy, ethoxy, amino, methyl and ethyl together with an alkali metal compound selected from those represented by the following general formula:
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE520287D BE520287A (US08197722-20120612-C00042.png) | 1952-05-31 | ||
| US291076A US2697100A (en) | 1952-05-31 | 1952-05-31 | Alpha-acylthio-n(2-benzothiazolyl) succinimides |
| GB14768/53A GB748144A (en) | 1952-05-31 | 1953-05-27 | Improvements in light sensitive photographic materials and compounds for use therein |
| FR1097213D FR1097213A (fr) | 1952-05-31 | 1953-05-27 | Nouveaux composés de benzothiazole, procédés pour leur préparation et leurs applications, notamment en photographie |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US291076A US2697100A (en) | 1952-05-31 | 1952-05-31 | Alpha-acylthio-n(2-benzothiazolyl) succinimides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2697100A true US2697100A (en) | 1954-12-14 |
Family
ID=23118719
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US291076A Expired - Lifetime US2697100A (en) | 1952-05-31 | 1952-05-31 | Alpha-acylthio-n(2-benzothiazolyl) succinimides |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US2697100A (US08197722-20120612-C00042.png) |
| BE (1) | BE520287A (US08197722-20120612-C00042.png) |
| FR (1) | FR1097213A (US08197722-20120612-C00042.png) |
| GB (1) | GB748144A (US08197722-20120612-C00042.png) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2857274A (en) * | 1953-09-04 | 1958-10-21 | Polaroid Corp | Photographic compositions and processes |
| US3042521A (en) * | 1957-12-26 | 1962-07-03 | Gen Aniline & Film Corp | Antifoggants and stabilizers for photographic silver halide emulsion |
| US3320270A (en) * | 1963-10-08 | 1967-05-16 | Tri Kem Corp | Certain 2-acylimidothiazole compounds |
| US3888677A (en) * | 1972-10-13 | 1975-06-10 | Du Pont | Silver halide photographic material containing antifog agent with protected mercapto group |
-
0
- BE BE520287D patent/BE520287A/xx unknown
-
1952
- 1952-05-31 US US291076A patent/US2697100A/en not_active Expired - Lifetime
-
1953
- 1953-05-27 GB GB14768/53A patent/GB748144A/en not_active Expired
- 1953-05-27 FR FR1097213D patent/FR1097213A/fr not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2857274A (en) * | 1953-09-04 | 1958-10-21 | Polaroid Corp | Photographic compositions and processes |
| US3042521A (en) * | 1957-12-26 | 1962-07-03 | Gen Aniline & Film Corp | Antifoggants and stabilizers for photographic silver halide emulsion |
| US3320270A (en) * | 1963-10-08 | 1967-05-16 | Tri Kem Corp | Certain 2-acylimidothiazole compounds |
| US3888677A (en) * | 1972-10-13 | 1975-06-10 | Du Pont | Silver halide photographic material containing antifog agent with protected mercapto group |
Also Published As
| Publication number | Publication date |
|---|---|
| GB748144A (en) | 1956-04-25 |
| FR1097213A (fr) | 1955-07-01 |
| BE520287A (US08197722-20120612-C00042.png) |
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