US3377167A - Fixing agents for photosensitive compositions containing leucotriphenyl methane derivatives; leuco xanthene compounds or leuco anthracene compounds - Google Patents
Fixing agents for photosensitive compositions containing leucotriphenyl methane derivatives; leuco xanthene compounds or leuco anthracene compounds Download PDFInfo
- Publication number
- US3377167A US3377167A US445273A US44527365A US3377167A US 3377167 A US3377167 A US 3377167A US 445273 A US445273 A US 445273A US 44527365 A US44527365 A US 44527365A US 3377167 A US3377167 A US 3377167A
- Authority
- US
- United States
- Prior art keywords
- leuco
- compounds
- leucotriphenyl
- anthracene
- photosensitive compositions
- 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
- 239000000203 mixture Substances 0.000 title description 25
- 150000001454 anthracenes Chemical class 0.000 title description 5
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 title description 2
- 125000001834 xanthenyl group Chemical class C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 description 29
- 238000010438 heat treatment Methods 0.000 description 13
- 239000012190 activator Substances 0.000 description 12
- -1 ANTHRACENE COM- POUNDS Chemical class 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 229910052740 iodine Inorganic materials 0.000 description 6
- 239000000470 constituent Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 238000007792 addition Methods 0.000 description 4
- 229910052787 antimony Inorganic materials 0.000 description 4
- 229910052785 arsenic Inorganic materials 0.000 description 4
- 229910052797 bismuth Inorganic materials 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 150000002896 organic halogen compounds Chemical class 0.000 description 4
- 239000000123 paper Substances 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 150000003732 xanthenes Chemical class 0.000 description 4
- 125000003435 aroyl group Chemical group 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
- 229910001864 baryta Inorganic materials 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- 229910021478 group 5 element Inorganic materials 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 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
- JXRGUPLJCCDGKG-UHFFFAOYSA-N 4-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=C(S(Cl)(=O)=O)C=C1 JXRGUPLJCCDGKG-UHFFFAOYSA-N 0.000 description 1
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical class C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 150000004961 triphenylmethanes Chemical class 0.000 description 1
- 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 1
- 238000005406 washing Methods 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
-
- 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
- G03C1/72—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705
- G03C1/73—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705 containing organic compounds
- G03C1/732—Leuco dyes
Definitions
- ABSTRACT OF THE DISCLOSURE Fixing of photosensitive compositions by gentle heating is facilitated by the addition of suitable amounts of triaryl compounds of Sb, P, As or Bi to photosensitive compositions containing leucotriphenylmethane derivatives or leuco xanthene compounds or leuco anthracene compounds, plus an activator which enhances a color forming reaction when the leuco compound is exposed to a suitable dose of radiation.
- the fixing of print-out images obtained with such compositions is accomplished by removal of unreacted constituents from the composition.
- Two methods of fixing were described therein: fixing by heating suificiently to remove any residual unreacted CBr or other active constituent from the composition and fixing of the print-out image by solvent washing or rinsing of the same in a solvent whereby the CB1; or
- a principal object of the present invention is to render photosensitive compositions of the type described above more amenable to fixing by gentleheating.
- a principal object of the present invention is to render photosensitive compositions of the type described above more amenable to heat-fixation 'by the addition of compounds which will prevent the oxidation of the unreacted leuco compound, i.e., that which remains after imaging takes place.
- Such compounds may be oxidized themselves to some colorless product-said oxidation being preferential to the oxidation of the leuco base.
- Such compounds may react with the unreacted leuco compound upon mild heating to form a. colorless product which is no longer photographically active and which will no longer be oxidizabIe to form colored background fog.
- volatile organic halogen compounds are used as activators these will be driven off and no longer be available for activation by light.
- leuco compounds Typical leuco compounds include the following: Leuco triphenyl methane derivatives, represented by the wherein each R represents either H or group.
- Leuco xanthene derivatives represented by the formula an alkyl or aryl I'm H v wherein each R represents either H or an alkyl or aryl group; 1
- Leuco anthracene derivatives represented by the formula wherein each R represents either H or an alkyl or aryl group and each R represents either H or an alkyl group.
- activator compounds Suitable activator compounds for the photosensitive compositions based on the combination of the above identified leuco compounds include any of the following:
- the fixing agents of this invention are the triaryl compounds of the following Group V elements: Sb, Bi, As and P, and particularly the triphenyl compounds of those elements, namely:
- Triphenylphosphine Triphenylarsine Triphenylstibine Triphenylbismuthine The fixing agent may be incorporated in otherwise known compositions at the time they are prepared or it may be added to them just prior to their use, e.g. just prior to their application to a suitable support such as paper, plastic or cloth or any other base material.
- a suitable support such as paper, plastic or cloth or any other base material.
- Example 1 One hundred milligrams of the leuco anthracene compound 2,7-bis (dimethylamino)--p-dimethylaminophenyl-9,10-dihydro-9,9-dimethylanthracene and seven hundred milligrams of carbon tetrabromide were dissolved in two cc. of a 2.5% polystyrene (Dow-Styron 700) solution in benzene followed by additions of two cc. of acetone and one cc. of a 4% solution of triphenylstibene in acetone. This mixture was coated .0015 inch wet thickness on baryta paper whose surface contained a polyvinyl alcohol surface sealing layer. The coating was applied by means of a Bird applicator blade and a vacuum plate was used for holding the paper flat while the coating was applied. Photographic safelight conditions were used during the coating procedure.
- the photosensitive surface was exposed to a fifteen time (15X) enlargement of a microfilm negative using a standard amateur slide projector with a 500 watt bulb.
- the exposure time was ten seconds which was sufficient to give a good quality print-out positive rendition of the projected negative.
- the exposed print was placed in an oven with moving air at 100 C. for sixty seconds after which the print was fully fixed and no longer sensitive to light.
- Example 2 The same procedure as used in Example 1 except that the one cc. of 4% triphenylstibene was replaced by one cc. of 2% solution of triphenylarsine in acetone. After sixty seconds heating in moving air at 100 C., the print was fully fixed and no longer sensitive to light.
- Example 3 The same procedure as used in Example 1 except that the one cc. of 4% triphenylstibene was replaced with one cc. of 1% triphenylbismuthine in acetone. After sixty seconds heating in moving air at 100 C, the print was fully fixed and no longer sensitive to light.
- Example 4 The same procedure as used in Example 1 except that the leuco anthracene compound was replaced with 50 milligrams of the leuco xanthene compound 3,6-bis(dimethylamino) 9 (p-dimethylamino)phenylxanthene. After ten seconds exposure to the projected image described in Example 1 and sixty seconds heating in moving air at 100 C. the print was fully fixed and no longer sensitive to light.
- the invention is applicable to other activators than those described in Examples 1 to 5, as shown by the following example:
- Example 6 One hundred milligrams of the leuco anthracene compound 2,7 bis(dimethylamino) 10-p dimethylaminophenyl-9,10-dihydro-9,9-dimethylanthracene and one hundred milligrams of p-nitrobenzenesulfonyl chloride were dissolved in two cc. of a 10% solution of polystyrene in benzene containing 10 milligrams of triphenylstibene and two cc. of acetone. The coating was applied to baryta paper in the manner described in Example 1. The dried coating was exposed to the 15X projection for 60 seconds followed by 60 seconds heating in 100 C. air. The heated print was fully fixed and no longer sensitive to light.
- composition which prints out a visible image directly as a result of exposure to a sufiicient dosage of .visible radiation and which consists essentially of at least one leuco compound selected from the group consisting of leucotriphenyl-methane compounds, leuco anthracene compounds and leuco xanthene compounds and at least one activator for said leuco compound, the improvement which consists in incorporating an amount of triaryl compound of an element selected from the group consisting of Sb, As, Bi and P sufiicient to permit fixing by gently heating any visible image resulting from exposure of said composition to visible light.
- composition of claim 1 wherein the triaryl compound is a triphenyl compound.
- composition of claim 1 wherein the leuco compound is a leuco anthracene represented by the general formula wherein each R represents a monovalent radical selected from the group consisting of H, alkyl and aryl and each R is a monovalent radical selected from the group consisting of H and alkyl.
- composition of claim 1 wherein the activator is a compound represented by the formula ACX wherein A represents a monovalent member selected from the group consisting of H, Cl, Br, I, alkyl, aryl and aroyl and each X represents a halogen atom selected from the group consisting of Cl, Br and I.
- a method of fixing visible images printed out from a composition consisting essentially of at least one leuco compound selected from the group consisting of leucotriphenyl-methane compounds, leuco anthracene compounds and leuco xanthene compounds and at least one activator or sensitizer for said leuco compound the improvement which comprises including a triaryl compound in said composition selected from the group consisting of triaryl compounds of P, As, Sb and Bi, exposing the composition to sufiicient light of a suitable wavelength to produce a colored photoreaction production, and fixing the resulting product by heating to a temperature up to about 120 C.
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)
- Heat Sensitive Colour Forming Recording (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US445273A US3377167A (en) | 1965-04-02 | 1965-04-02 | Fixing agents for photosensitive compositions containing leucotriphenyl methane derivatives; leuco xanthene compounds or leuco anthracene compounds |
| DEH58653A DE1293021B (de) | 1965-04-02 | 1966-02-25 | Lichtempfindliche auskopierende Schicht |
| GB11404/66A GB1086762A (en) | 1965-04-02 | 1966-03-15 | Fixing photosensitive compositions |
| FR55092A FR1472635A (fr) | 1965-04-02 | 1966-03-25 | Perfectionnements aux compositions photosensibles activées |
| NL6603912A NL6603912A (enrdf_load_stackoverflow) | 1965-04-02 | 1966-03-25 | |
| BE678519D BE678519A (enrdf_load_stackoverflow) | 1965-04-02 | 1966-03-25 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US445273A US3377167A (en) | 1965-04-02 | 1965-04-02 | Fixing agents for photosensitive compositions containing leucotriphenyl methane derivatives; leuco xanthene compounds or leuco anthracene compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3377167A true US3377167A (en) | 1968-04-09 |
Family
ID=23768250
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US445273A Expired - Lifetime US3377167A (en) | 1965-04-02 | 1965-04-02 | Fixing agents for photosensitive compositions containing leucotriphenyl methane derivatives; leuco xanthene compounds or leuco anthracene compounds |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3377167A (enrdf_load_stackoverflow) |
| BE (1) | BE678519A (enrdf_load_stackoverflow) |
| DE (1) | DE1293021B (enrdf_load_stackoverflow) |
| GB (1) | GB1086762A (enrdf_load_stackoverflow) |
| NL (1) | NL6603912A (enrdf_load_stackoverflow) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3630735A (en) * | 1966-08-24 | 1971-12-28 | Keuffel & Esser Co | Method for fixing light-sensitive free radical photographic materials with heavy metal salts |
| EP0073619A1 (en) * | 1981-08-21 | 1983-03-09 | Konica Corporation | A process for preventing dye images from discoloring and fading |
| US4634657A (en) * | 1984-08-23 | 1987-01-06 | E. I. Du Pont De Nemours And Company | Photoimaging compositions containing substituted 1,2-dibromoethanes |
| US4794069A (en) * | 1986-07-15 | 1988-12-27 | Shin Nisso Kako Co., Ltd. | Spirobenzanthracene phthalide compounds, processes for preparing same and color forming recording materials containing said compounds |
| WO2001029837A1 (en) * | 1999-10-15 | 2001-04-26 | Trid Store Ip, Llc | Medium for fluorescent read-only multilayer optical information carrier and its manufacturing method |
| JP2007314721A (ja) * | 2006-05-29 | 2007-12-06 | Funai Electric Advanced Applied Technology Research Institute Inc | 組成物 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3042515A (en) * | 1959-01-16 | 1962-07-03 | Horizons Inc | Print-out compositions for photographic purposes and process of using same |
| US3140948A (en) * | 1961-10-18 | 1964-07-14 | 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 |
| US3322542A (en) * | 1963-11-14 | 1967-05-30 | American Cyanamid Co | Stabilization additives for photochromic compounds |
-
1965
- 1965-04-02 US US445273A patent/US3377167A/en not_active Expired - Lifetime
-
1966
- 1966-02-25 DE DEH58653A patent/DE1293021B/de active Pending
- 1966-03-15 GB GB11404/66A patent/GB1086762A/en not_active Expired
- 1966-03-25 BE BE678519D patent/BE678519A/xx unknown
- 1966-03-25 NL NL6603912A patent/NL6603912A/xx unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3042515A (en) * | 1959-01-16 | 1962-07-03 | Horizons Inc | Print-out compositions for photographic purposes and process of using same |
| US3140948A (en) * | 1961-10-18 | 1964-07-14 | 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 |
| US3322542A (en) * | 1963-11-14 | 1967-05-30 | American Cyanamid Co | Stabilization additives for photochromic compounds |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3630735A (en) * | 1966-08-24 | 1971-12-28 | Keuffel & Esser Co | Method for fixing light-sensitive free radical photographic materials with heavy metal salts |
| EP0073619A1 (en) * | 1981-08-21 | 1983-03-09 | Konica Corporation | A process for preventing dye images from discoloring and fading |
| US4634657A (en) * | 1984-08-23 | 1987-01-06 | E. I. Du Pont De Nemours And Company | Photoimaging compositions containing substituted 1,2-dibromoethanes |
| US4794069A (en) * | 1986-07-15 | 1988-12-27 | Shin Nisso Kako Co., Ltd. | Spirobenzanthracene phthalide compounds, processes for preparing same and color forming recording materials containing said compounds |
| WO2001029837A1 (en) * | 1999-10-15 | 2001-04-26 | Trid Store Ip, Llc | Medium for fluorescent read-only multilayer optical information carrier and its manufacturing method |
| JP2007314721A (ja) * | 2006-05-29 | 2007-12-06 | Funai Electric Advanced Applied Technology Research Institute Inc | 組成物 |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6603912A (enrdf_load_stackoverflow) | 1966-10-03 |
| BE678519A (enrdf_load_stackoverflow) | 1966-09-01 |
| GB1086762A (en) | 1967-10-11 |
| DE1293021B (de) | 1969-04-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3140948A (en) | Photography | |
| US3305361A (en) | Information recording | |
| US3284205A (en) | Benzotriazole and heterocyclic ketimide activators for leuco compounds | |
| US3300314A (en) | Nonsilver, light-sensitive photographic elements | |
| US3147117A (en) | Process of forming print-out images from light sensitive organic amine compositions | |
| US3042516A (en) | Print-out compositions for photographic purposes and process of using same | |
| US1976302A (en) | Photothermographic composition | |
| US3527639A (en) | Light-sensitive composition utilizing anthraquinone derivatives as optical sensitizers | |
| GB959035A (en) | Photographic process and composition | |
| US3377167A (en) | Fixing agents for photosensitive compositions containing leucotriphenyl methane derivatives; leuco xanthene compounds or leuco anthracene compounds | |
| US3620748A (en) | N-vinyl amine/halogen liberating composition sensitized with 9-vinyl carbazoles or polyacenes, or transannular peroxides of polyacenes | |
| US3615478A (en) | Method of fixing photographic material containing a free radial producing compound | |
| US2324060A (en) | Photographic copying paper | |
| US3846131A (en) | Recording material containing a polyhalogenated hydrocarbon photoactivator and a dye forming combination of an indolizine derivative and an aldehyde and the use thereof | |
| US3736139A (en) | Heat and light stabilization of photosensitive elements containing poly-halogenated hydrocarbons,n-vinylcarbazoles and difurfurylidene pentaerythritols | |
| US3082086A (en) | Fixing of print-out images | |
| US3275443A (en) | Anti-fogging agents for an n-vinyl, organic halogen, dye former system | |
| USRE29748E (en) | Dry working black image compositions comprising organic halogen compounds and ethylene compounds | |
| US3272635A (en) | Compositions containing leuco xanthene dyes and suitable activators | |
| US4066459A (en) | Free radical photosensitive compositions with improved sensitivity and shelf life stability | |
| US3102029A (en) | Print-out process with aryl amine and polyphenylmethane carbinols | |
| US3164467A (en) | Ultraviolet sensitive print-out compositions and process for image-wise exposure and fixing of same | |
| US3887808A (en) | Thermoimaging process utilizing a photochromic material containing a spiropyran, a polyhalogenated hydrocarbon, a thiol compound and a polyvinylcarbazole | |
| US3510309A (en) | Phenolic stabilizer in non-silver photosensitive composition | |
| US3493376A (en) | Dry working black image compositions |