US3359105A - Speed-increasing agents for an nu-vinyl amine and organic halogen dye former system - Google Patents
Speed-increasing agents for an nu-vinyl amine and organic halogen dye former system Download PDFInfo
- Publication number
- US3359105A US3359105A US438760A US43876065A US3359105A US 3359105 A US3359105 A US 3359105A US 438760 A US438760 A US 438760A US 43876065 A US43876065 A US 43876065A US 3359105 A US3359105 A US 3359105A
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- US
- United States
- Prior art keywords
- compounds
- compound
- sulfur
- organic halogen
- density
- 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
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- 229920002554 vinyl polymer Polymers 0.000 title claims description 11
- 229910052736 halogen Inorganic materials 0.000 title claims description 5
- 150000002367 halogens Chemical class 0.000 title claims description 5
- 239000000203 mixture Substances 0.000 claims description 54
- -1 MERCAPTO COMPOUNDS Chemical class 0.000 claims description 16
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 239000011593 sulfur Substances 0.000 claims description 12
- 150000002894 organic compounds Chemical class 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 150000002019 disulfides Chemical class 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 claims description 3
- 239000011630 iodine Substances 0.000 claims description 2
- 150000003464 sulfur compounds Chemical class 0.000 claims description 2
- 150000001721 carbon Chemical class 0.000 claims 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 15
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 15
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 13
- 238000007792 addition Methods 0.000 description 12
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 11
- 150000002896 organic halogen compounds Chemical class 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 230000005855 radiation Effects 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- HVYVMSPIJIWUNA-UHFFFAOYSA-N triphenylstibine Chemical compound C1=CC=CC=C1[Sb](C=1C=CC=CC=1)C1=CC=CC=C1 HVYVMSPIJIWUNA-UHFFFAOYSA-N 0.000 description 6
- 238000009472 formulation Methods 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 230000006872 improvement Effects 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 4
- 229910001864 baryta Inorganic materials 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- CBFCDTFDPHXCNY-UHFFFAOYSA-N icosane Chemical compound CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 description 4
- OKJPEAGHQZHRQV-UHFFFAOYSA-N iodoform Chemical compound IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000005864 Sulphur Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 229920000915 polyvinyl chloride Polymers 0.000 description 3
- 239000004800 polyvinyl chloride Substances 0.000 description 3
- OGVPXEPSTZMAFF-UHFFFAOYSA-N 1,1,1,2,2-pentabromoethane Chemical compound BrC(Br)C(Br)(Br)Br OGVPXEPSTZMAFF-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- GUUVPOWQJOLRAS-UHFFFAOYSA-N Diphenyl disulfide Chemical compound C=1C=CC=CC=1SSC1=CC=CC=C1 GUUVPOWQJOLRAS-UHFFFAOYSA-N 0.000 description 2
- 229920003345 Elvax® Polymers 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 125000003435 aroyl group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 150000002898 organic sulfur compounds Chemical class 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- KIWUVOGUEXMXSV-UHFFFAOYSA-N rhodanine Chemical compound O=C1CSC(=S)N1 KIWUVOGUEXMXSV-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 150000003536 tetrazoles Chemical class 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 description 1
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Substances C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 1
- JAAIPIWKKXCNOC-UHFFFAOYSA-N 1h-tetrazol-1-ium-5-thiolate Chemical class SC1=NN=NN1 JAAIPIWKKXCNOC-UHFFFAOYSA-N 0.000 description 1
- FLFWJIBUZQARMD-UHFFFAOYSA-N 2-mercapto-1,3-benzoxazole Chemical compound C1=CC=C2OC(S)=NC2=C1 FLFWJIBUZQARMD-UHFFFAOYSA-N 0.000 description 1
- NSYKYZBOQLCIHR-UHFFFAOYSA-N 2-nitro-1,3-benzothiazole Chemical compound C1=CC=C2SC([N+](=O)[O-])=NC2=C1 NSYKYZBOQLCIHR-UHFFFAOYSA-N 0.000 description 1
- OOMNEOSPLONJPF-UHFFFAOYSA-N 3-phenyl-2-[(3-phenyl-1h-indol-2-yl)disulfanyl]-1h-indole Chemical compound N1C2=CC=CC=C2C(C=2C=CC=CC=2)=C1SSC=1NC2=CC=CC=C2C=1C1=CC=CC=C1 OOMNEOSPLONJPF-UHFFFAOYSA-N 0.000 description 1
- CYCKHTAVNBPQDB-UHFFFAOYSA-N 4-phenyl-3H-thiazole-2-thione Chemical compound S1C(S)=NC(C=2C=CC=CC=2)=C1 CYCKHTAVNBPQDB-UHFFFAOYSA-N 0.000 description 1
- IDPNFKLUBIKHSW-UHFFFAOYSA-N 6-amino-3h-1,3-benzothiazole-2-thione Chemical compound NC1=CC=C2N=C(S)SC2=C1 IDPNFKLUBIKHSW-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
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000003467 diminishing effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 229910021478 group 5 element Inorganic materials 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- SQEHCNOBYLQFTG-UHFFFAOYSA-M lithium;thiophene-2-carboxylate Chemical compound [Li+].[O-]C(=O)C1=CC=CS1 SQEHCNOBYLQFTG-UHFFFAOYSA-M 0.000 description 1
- 150000002829 nitrogen Chemical class 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- 125000001741 organic sulfur group Chemical group 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000000452 restraining effect Effects 0.000 description 1
- 239000010979 ruby Substances 0.000 description 1
- 229910001750 ruby Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- BPLUKJNHPBNVQL-UHFFFAOYSA-N triphenylarsine Chemical compound C1=CC=CC=C1[As](C=1C=CC=CC=1)C1=CC=CC=C1 BPLUKJNHPBNVQL-UHFFFAOYSA-N 0.000 description 1
- ZHXAZZQXWJJBHA-UHFFFAOYSA-N triphenylbismuthane Chemical compound C1=CC=CC=C1[Bi](C=1C=CC=CC=1)C1=CC=CC=C1 ZHXAZZQXWJJBHA-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
- G03C1/00—Photosensitive materials
- G03C1/675—Compositions containing polyhalogenated compounds as photosensitive substances
Definitions
- This invention relates to light sensitive compositions such as those described in United States Patent 3,042,517 issued July 3, 1962. More particularly, it relates to the addition of certain classes of nitrogen and/ or sulfur containing organic compounds to photosensitive compositions based on N-vinylcarbazole and CBr
- light sensitive compositions consisting essentially of suitable N-vinyl com-pounds and suitable organic halogen compounds, which compositions when exposed photographically yielded a latent image which was rendered visible by means of either heat or infrared.
- the resulting formulation was coated on gm. baryta paper in the manner described in the above noted patent to 0.003 inch wet thickness.
- the coatings were exposed in four different Ways as follows:
- Exposures were made to a sunlamp for l, 5, 30 and 60 seconds without a negative (step wedge) or glass plate both of which will absorb ultraviolet radiation from the sunlamp and pass only visible radiation.
- mercapto compounds selected from the group consisting of mercapto benzothiazoles, and mercaptotetrazoles are effective in significantly increasing the response of N-vinylcarbazole, car bon tetrabromide compositions upon exposure to light and subsequent heat development.
- the amount of the mercaptobenzothiazole or mercaptotetrazole compound which yield significantly improved results may be varied between 5 and 150 milligrams of this type of addition for the specific base formula given and optimum amounts are in the range of 40 to 75 milligrams in the base composition given.
- the improvement begins to be noticeable at a 5 milligram addition and begins to reach a maximum in the range of 40 to 75 after which further additions yield no large improvement on the increase in speed and increase in density at equivalent exposures.
- compositions of the instant invention are not confined to those described in the foregoing example as will be apparent from the data which follows and it is to be understood that each and any one or more of the constituents utilized in the example may be replaced by equivalent or similar materials.
- CBr organic halo-gen compounds
- pentabromoethane, iodoform and other compounds such as pentabromoethane, iodoform and other compounds such a those specifically described in United States Patent 3,147,117 issued Sept. 1, 1964 and represented by the general formula RC-X wherein each X represents a chlorine, bromine or iodine atom and not all of the Xs need be the same, and R represents alkyl, aryl, aralkyl, haloalkyl, aroyl, Cl, Br, I or H.
- RC-X wherein each X represents a chlorine, bromine or iodine atom and not all of the Xs need be the same, and R represents alkyl, aryl, aralkyl, haloalkyl, aroyl, Cl, Br, I or H.
- film forming binder material the presence of which is optional since when it is absent the composition can be applied to paper or other absorbent substrates and utilized when carried on such supports.
- polystyrene or polvvinylchloride utilized in the preceding examples, other homopolymers or copolymers or mixtures of film forming materials may be utilized.
- some film forming materials appear to'intluence the photosensitivity TABLE I.RESULTS OF EXPOSURES TO U.V. AND
- No Mercapto Compound (control) 8 1.0 1.10 1 .18 1 .16 5 21 5 19 30 60 30 44 60 1.52 60 .80 ltlercapto-benzothiazole 9 1. 24 14 2. 04 l 35 1 28 5 2.13 5 1.17 30 2.46 30 2.10 60 2. 42 60 2.01 Phenylmercapto tetrazole. 8 1- 14 6 0.90 1 .18 1 32 5 58 5 78 30 1.38 30 2.15 60 1. 52 60 2. 22 Methylmercapto tetrazole 10 1.26 11 1. 08 1 .17 1 .195
- Density is white light reflection density using a Photovolt densitometer.
- Suitable sulfur-containing compounds include the following sulfur-containing organic compounds:
- compositions of this invention may contain other substances added for a specific purpose.
- One particularly preferred group of compounds which may be included in the compositions of this invention are the triaryl compounds of Group V elements particularly the triphenyl compounds of antimony, phosphorus, arsenic and bismuth each of which has been found to be effective in the diminishing or total elimination of the fogging occurring as a result of the thermal development step.
- a base composition was made up as follows:
- Elvax is a copolymer of polyethylene and polyvinylacetatc manufactured by the duPont company.
- this formulation was coated under a Wratten 1 series safelight at a 0.003" wet thickness on pound baryta paper and after which was allowed to dry in the dark for 30 minutes before exposure. Comparisons were made between exposure results obtained on this control and the composition with the various sulphur compounds added to this formulation as listed in Table II.
- the designated weight of the sulphur compound listed in Table II was added to the base composition just described, thoroughly stirred until dissolved, and again coated in a 3 mil wet thickness on baryta paper.
- compositions were then exposed to a 500 watt photofiood reflector type lamp, placed at a distance of 12" and the exposure time in each case was 5 seconds. The exposure was made behind a mask so that a sharp demarcation between exposed and unexposed conditions could be established.
- the sample was developed with an infrared lamp fitted with a ruby glass envelope which filtered out all radiation below 6500 A. The specimen was maintained at a distance of approximately 3 to 4" from the infrared lamp and moved continuously during thermal and infrared development to prevent localized overheating. A time period of development of 1 minute exposure to the inrfared lamp was utilized in each case.
- the image portions of this composition were developed to a net density of between 2.5 and 3 in the image exposed areas after 60 seconds development to the infrared lamp described previously. Fog levels remained regularly below 0.05 unit of density under such conditions. Continuing the infrared development for a period of 5 minutes longer raises the fog level from 0.05 to about 0.07, whereas in the absence of the triphenylstibine composition continuing the infrared lamp development for 2 minutes rather than the 1 minute recommended previously raises the background fog level to 0.32 units of density and as the infrared development is continued for a period of 5 minutes the background fog level rises above a density of 1.5 making the result effectively useless under such exposure conditions for practical purposes.
- the relative proportions of N-vinyl compound to organic halogen compound should be between 5 and 0.5 part by weight of N-vinyl compound for each part by weight of organic halogen compound; the amount of organic sulfur containing compound should be between about 2.5 and 100 parts by weight for each 1000 parts by weight of organic halogen compound; and when present, the aryl Group Vb compound should be between 5 and 50 parts by weight for each 1000 parts by weight of organic halogen compound.
- a photosensitive composition comprising:
- a photographic film comprising a composition according to claim 1 coated on a support.
- composition according to claim 1 dispersed uniformly throughout a support.
- N-vinyl compound is N-vinyl carbazole.
- composition according to claim 5 wherein the organic halogen compound is a halogen containing hydrocarbon.
- composition according to claim 5 wherein the organic sulfur compound is a mercapto compound.
- composition according to claim 7 wherein the mercapto compound is a mercapto benzothiazole.
- composition of claim 1 containing in addition a triaryl compound selected from the group consisting of triphenylstibine, triphenylbismuthine, triphenylarsine and triphenylphosphine as an antifoggant.
- a triaryl compound selected from the group consisting of triphenylstibine, triphenylbismuthine, triphenylarsine and triphenylphosphine as an antifoggant.
- a method of photographically producing a visible image which comprises preparing a film containing the composition of claim 1, photographically exposing the film to light thereby producing a latent image in said film, and developing a visible image thereof by applying thermal radiation to said latent image bearing film whereby said visible image is simultaneously developed and fixed.
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US438760A US3359105A (en) | 1965-03-10 | 1965-03-10 | Speed-increasing agents for an nu-vinyl amine and organic halogen dye former system |
| DE19661547942 DE1547942A1 (de) | 1965-03-10 | 1966-02-24 | Lichtempfindliche Praeparate |
| BE677396D BE677396A (en)van) | 1965-03-10 | 1966-03-04 | |
| FR52091A FR1470701A (fr) | 1965-03-10 | 1966-03-04 | Composition photosensible activée |
| GB9929/66A GB1107279A (en) | 1965-03-10 | 1966-03-07 | Photosensitive compositions |
| NL6602979A NL6602979A (en)van) | 1965-03-10 | 1966-03-08 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US438760A US3359105A (en) | 1965-03-10 | 1965-03-10 | Speed-increasing agents for an nu-vinyl amine and organic halogen dye former system |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3359105A true US3359105A (en) | 1967-12-19 |
Family
ID=23741896
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US438760A Expired - Lifetime US3359105A (en) | 1965-03-10 | 1965-03-10 | Speed-increasing agents for an nu-vinyl amine and organic halogen dye former system |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3359105A (en)van) |
| BE (1) | BE677396A (en)van) |
| DE (1) | DE1547942A1 (en)van) |
| GB (1) | GB1107279A (en)van) |
| NL (1) | NL6602979A (en)van) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3495987A (en) * | 1965-09-03 | 1970-02-17 | Du Pont | Photopolymerizable products |
| US3512975A (en) * | 1964-12-30 | 1970-05-19 | Kalle Ag | Process for the preparation of positive copies and material for performing the process |
| US3887808A (en) * | 1972-06-26 | 1975-06-03 | Agfa Gevaert | Thermoimaging process utilizing a photochromic material containing a spiropyran, a polyhalogenated hydrocarbon, a thiol compound and a polyvinylcarbazole |
| US3980480A (en) * | 1970-09-01 | 1976-09-14 | Urbain Leopold Laridon | Photographic recording and reproduction of information photochromic composition containing polyhalogenated hydrocarbon, spiropyran compound and heterocyclic mercapto compound and the use thereof |
| US4036648A (en) * | 1975-06-30 | 1977-07-19 | International Business Machines Corporation | Highly conductive printing medium containing a halogenated hydrocarbon photoactivator and a tetrathiafulvalene or a related compound thereof |
| WO1982000782A1 (en) * | 1980-09-10 | 1982-03-18 | Corp Panelgraphic | Abrasion resistant coating composition |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3042518A (en) * | 1960-01-08 | 1962-07-03 | Horizons Inc | Light sensitive photographic compositions |
| US3042516A (en) * | 1959-09-22 | 1962-07-03 | Horizons Inc | Print-out compositions for photographic purposes and process of using same |
| US3046125A (en) * | 1960-04-19 | 1962-07-24 | Horizons Inc | Print-out photoresists and method of making same |
| US3275443A (en) * | 1963-08-14 | 1966-09-27 | Horizons Inc | Anti-fogging agents for an n-vinyl, organic halogen, dye former system |
| US3285744A (en) * | 1963-04-04 | 1966-11-15 | Horizons Inc | Photography |
-
1965
- 1965-03-10 US US438760A patent/US3359105A/en not_active Expired - Lifetime
-
1966
- 1966-02-24 DE DE19661547942 patent/DE1547942A1/de active Pending
- 1966-03-04 BE BE677396D patent/BE677396A/xx unknown
- 1966-03-07 GB GB9929/66A patent/GB1107279A/en not_active Expired
- 1966-03-08 NL NL6602979A patent/NL6602979A/xx unknown
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3042516A (en) * | 1959-09-22 | 1962-07-03 | Horizons Inc | Print-out compositions for photographic purposes and process of using same |
| US3042518A (en) * | 1960-01-08 | 1962-07-03 | Horizons Inc | Light sensitive photographic compositions |
| US3046125A (en) * | 1960-04-19 | 1962-07-24 | Horizons Inc | Print-out photoresists and method of making same |
| US3285744A (en) * | 1963-04-04 | 1966-11-15 | Horizons Inc | Photography |
| US3275443A (en) * | 1963-08-14 | 1966-09-27 | Horizons Inc | Anti-fogging agents for an n-vinyl, organic halogen, dye former system |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3512975A (en) * | 1964-12-30 | 1970-05-19 | Kalle Ag | Process for the preparation of positive copies and material for performing the process |
| US3495987A (en) * | 1965-09-03 | 1970-02-17 | Du Pont | Photopolymerizable products |
| US3980480A (en) * | 1970-09-01 | 1976-09-14 | Urbain Leopold Laridon | Photographic recording and reproduction of information photochromic composition containing polyhalogenated hydrocarbon, spiropyran compound and heterocyclic mercapto compound and the use thereof |
| US3887808A (en) * | 1972-06-26 | 1975-06-03 | Agfa Gevaert | Thermoimaging process utilizing a photochromic material containing a spiropyran, a polyhalogenated hydrocarbon, a thiol compound and a polyvinylcarbazole |
| US4036648A (en) * | 1975-06-30 | 1977-07-19 | International Business Machines Corporation | Highly conductive printing medium containing a halogenated hydrocarbon photoactivator and a tetrathiafulvalene or a related compound thereof |
| US4082552A (en) * | 1975-06-30 | 1978-04-04 | International Business Machines Corporation | Process of optically printing highly conductive character utilizing a medium containing a halogenated hydrocarbon photoactivator and a tetrathiafulvalene or a related compound thereof |
| WO1982000782A1 (en) * | 1980-09-10 | 1982-03-18 | Corp Panelgraphic | Abrasion resistant coating composition |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1547942A1 (de) | 1969-12-11 |
| BE677396A (en)van) | 1966-08-01 |
| NL6602979A (en)van) | 1966-09-12 |
| GB1107279A (en) | 1968-03-27 |
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