WO1982002258A1 - Derives (alpha)-diazoacetyle de nitrures aromatiques heterocyliques et materiau sensible a la lumiere - Google Patents

Derives (alpha)-diazoacetyle de nitrures aromatiques heterocyliques et materiau sensible a la lumiere Download PDF

Info

Publication number
WO1982002258A1
WO1982002258A1 PCT/SU1981/000079 SU8100079W WO8202258A1 WO 1982002258 A1 WO1982002258 A1 WO 1982002258A1 SU 8100079 W SU8100079 W SU 8100079W WO 8202258 A1 WO8202258 A1 WO 8202258A1
Authority
WO
WIPO (PCT)
Prior art keywords
represent
light
group
atom
diazoacetyl
Prior art date
Application number
PCT/SU1981/000079
Other languages
English (en)
French (fr)
Russian (ru)
Inventor
Khimi Fiz An Sssr Inst
Original Assignee
Emanuel Nikolai Markovich
Kartsev Viktor Georgievich
Pokidova Tamara Sergeevna
Kirkovsky Leonid Ivanovich
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from SU803217545A external-priority patent/SU1232666A1/ru
Application filed by Emanuel Nikolai Markovich, Kartsev Viktor Georgievich, Pokidova Tamara Sergeevna, Kirkovsky Leonid Ivanovich filed Critical Emanuel Nikolai Markovich
Priority to JP82500892A priority Critical patent/JPS57502259A/ja
Priority to NL8120511A priority patent/NL8120511A/nl
Publication of WO1982002258A1 publication Critical patent/WO1982002258A1/ru

Links

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
    • G03C1/695—Compositions containing azides as the photosensitive substances

Definitions

  • the total invention is related to new chemical compounds, namely, to ⁇ -diazoacetyl derivatives of heterocycle ⁇ v, as well as to the light-sensitive material made on the basis of the named new compounds.
  • structural analogues of the proposed new compounds can be considered: ⁇ and ⁇ l-diaz ⁇ acetylpyridines ⁇ mules: ⁇ 2
  • diazo-type compounds sensitive to ultraviolet light, form a simple image, requiring the process of ammonia ts ⁇ phenomena. ⁇ ashennaya ⁇ ma spirepi ⁇ an ⁇ v s ⁇
  • the spectral luminosity of salicylideneaniline is ⁇ 0.6 J/ ⁇ . 15
  • a significant disadvantage of the indicated light-sensitive materials is the fragility of the stitching process - the most fading fading the coloration in the dark is ⁇ 30 hours, while the discoloration of the grown ph ⁇ my is significantly intensified in the light, which significantly limits the time of ⁇ réelle the application and use of for ⁇ shsanny information.
  • the task is to create new compounds that have light sensitivity both in ultraviolet and in the visible 25 In the field of spectrum, on the basis of ⁇ g ⁇ , it would be possible to create non-ferrous light-sensitive materials that provide stable, high ⁇ - ⁇ .
  • ⁇ and ⁇ d-can have the same or different meanings and represent the elements of the input, groups
  • ⁇ 7 ⁇ 9 and represent with ⁇ b ⁇ y atom in ⁇ d ⁇ da pr ⁇ i r- - representing the group ⁇ 0 2 or ⁇ 3 ,
  • ⁇ d ⁇ d and represent the presence of an atom in the water, possessing light-sensitiveness, both in the ultra- and
  • a light-sensitive material which is made of soft and light ⁇ sensitively ⁇ g ⁇ poly ⁇ stallic ⁇ g ⁇ layer, ⁇ braz ⁇ -bath ⁇ g ⁇ ⁇ -diaz ⁇ acetyl color
  • ⁇ a
  • I?- ⁇ 3' ⁇ 4 represent with ⁇ m ⁇ d ⁇ - ⁇ da or the group ⁇ 0 2 » ⁇ -,, ⁇ and - can have
  • photosensitive material photosensitive polyetallic
  • photosensitive material for the storage of optical information with the help of lasers, sources of UV radiation and visible radiation ( ⁇ 450 nm) with the receipt of stable, diverse images using comfort, according to the present invention, photosensitive material, photosensitive polycrystalline layer of glass - acetylic pr ⁇ dnshli aromatic nitrogen heterocycles in ⁇ mules:
  • a light-sensitive material is used, photosensitive ⁇ Poly ⁇ g ⁇ ⁇ br ⁇ van Z- ⁇ enyl-4-diaz ⁇ acetylsidn ⁇ m ⁇ g ⁇ :
  • the luminosity of the materials, according to the invention is ⁇ ⁇ 0.1 J / em ⁇ (p ⁇ and R - 300 nm), ⁇ is 6 times 15 higher than that of analogs on the basis of anil c.
  • ⁇ ⁇ , ⁇ , * and ⁇ represent with ⁇ ⁇ m v ⁇ d ⁇ da or grugash ⁇ , ⁇ ⁇ ⁇ , ⁇ and ⁇ may have ⁇ din ⁇ ye or different values and preds s ⁇ b ⁇ y atom ⁇ l ⁇ réelle, groups 0 ⁇ , ⁇ , ⁇ Operations, ⁇ -piperidyl, ⁇ ⁇ ⁇ I, ⁇ ⁇ u003d ⁇ b, ⁇ b,
  • the compounds proposed in the present invention can be prepared in known ways, such as, for example, 2-diazoacetyl hin ⁇ lines of the general ⁇ mula:.
  • ⁇ ⁇ - piperidil, 8-me ⁇ réelle ⁇ in ⁇ lil, 2-mer ⁇ réelle ⁇ in ⁇ lil, and ⁇ i % ⁇ ⁇ represent the 0 ⁇ or ⁇ group using different methods (see U.S. Patent 4025515, class 260-256.4, published 1977 ) through the interaction of 2,4-di ⁇ l ⁇ -6-diaz ⁇ acetylpyrimi- ⁇ dyne with nucleophylline reagents of the general ⁇ mula:
  • ⁇ g ⁇ ⁇ for example, METAN ⁇ L
  • ⁇ r without neg ⁇ in 2-5 ⁇ m excess zero ⁇ il-nog ⁇ reagent in the presence of 2-3 ⁇ atn ⁇ excess of ⁇ i-° ethylamine (or without it ) at a temperature of ⁇ 0 to 80°C for a time of ⁇ 30 min to 10 hours depending on
  • the most expedient in terms of technical and economic indicators is the use of the proposed new substances as your photosensitive components in the materials
  • the proposed photosensitive materials with a polycrystalline layer based on the proposed new compounds have a number of advantages in comparison with the known ones: ⁇ I.
  • the proposed new connections allow images to be stable in the dark. As shown by the experimental data, a decrease in the frequency of images in the dark was not observed for 6 months.
  • the weakening of the ⁇ n ⁇ ast-n ⁇ sti is on average ⁇ 2 d ⁇ 40 days, which ⁇ ⁇ z- allows you to use the recorded information for a long time without a noticeable decrease in its quality.
  • Diaziasid is in the same way of lighting, the number of revealed in the a ⁇ inommexation in the ⁇ -radiation, ⁇ -eaten, the ⁇ distances for naughty. , ⁇ the increase of radiation
  • the resolving power of the layers on the basis of the proposed daaz ⁇ réelle ⁇ b ⁇ nil'nyh connections was determined by ⁇ l ⁇ l ⁇ r ⁇ lv ⁇ gle ⁇ e with the following study of ⁇ radiation products ⁇ d mi ⁇ s ⁇ Brass ⁇ m. For all the materials studied, K. ⁇ 900 mm.
  • the proposed compounds are also visual, polymerization, free radical,
  • the proposed light-sensitive materials produce various ⁇ classes of known chemical silver-free photosensitive systems.
  • Example I 2-diaz ⁇ acetyl ⁇ in ⁇ line . ⁇ ethereal distribution of diaz ⁇ methane, received pr ⁇ and ⁇ alkaline decomposition of 12 g of ni ⁇ z ⁇ methylurea pr ⁇ and intensive stirring and cooling for temperature temperatures -15°, drip for 20 minutes.
  • etheric solution 4.5 g (0.024 mole) At the end of the infusion, the reaction mixture is stirred for another 30 minutes without cooling, bringing the temperature to U ⁇ U D ⁇ 0 ° 0, the ether is evaporated and the crystallized garden ⁇ re-crystallize from hexane.
  • Example 2 4-methyl-2-diaz ⁇ cetyl ⁇ in ⁇ line the connection ⁇ ray ⁇ in the conditions of ⁇ analogous to . 0 indicated in Example I. Sample 72 . T.sh ⁇ .68° ⁇ . Found %:
  • Example 3 4- ⁇ and ⁇ -2-diaz ⁇ acetyl ⁇ in ⁇ line - naldine acid in 40 ml of abs.ether for 20 min. ⁇ mu from 20 g of ni ⁇ z ⁇ - • 30 methylurea, with intensive stirring. After that, the reaction mixture is cooled to a temperature of -3 ⁇ -40°C and maintained at this temperature for one hour.
  • Example 15 is indicated in Example 3 from 8-nitrodi acid chloranhydride and diazomethane. ⁇ y ⁇ d 58%. ⁇ .pl. 155- ⁇ 57°C (with ⁇ decomp.) . Daily calculation: C 54.55, ⁇ benz ⁇ l-ethyl acetate, 6:1) strength ⁇ l U -254. 0 Example 6. 2-diaz ⁇ ac
  • Stage I Obtaining ⁇ l ⁇ ide with ⁇ -pi ⁇ lin ⁇ in ⁇ ⁇ ta. 0.5 ml dimethyl ⁇ ma yes for 10 hours. izbyt ⁇ n 5 yut. ⁇ stat ⁇ extract twice with 40 ml of hexane. Hesan is evaporated and the stat is overheated, collecting the ⁇ share of ⁇ .boil. 76-82°C (10 mm ⁇ .st. ) . ⁇ d ⁇ l ⁇ anhydride 15.7 g (69%).
  • Stage I Di ⁇ l ⁇ anhydride of 2,6-pyridine dikarb ⁇ n ⁇ y in ⁇ y ⁇ yym ⁇ réellem 6. ⁇ y ⁇ d 75 .
  • Step 2 2,6-bisdiaz ⁇ acetylpyridine is obtained under conditions similar to those indicated in Example 6, from 8 g of di- ⁇ l ⁇ ayahyd ⁇ ide 2,6-pyridium ⁇ ab ⁇ ya ⁇ in acidic you and ethereal solution diaz ⁇ metayaa, obtained from 40 g of urea ni ⁇ z ⁇ meta. The falling crystal plant is filtered and
  • Stage I Obtaining 3-ni ⁇ -2,6-pyridium carb ⁇ ya ⁇ - voi ⁇ ta.
  • 83 g of permayagayaata potassium dissolve in - 1.4 liters of water during heating and add 17.6 g of 3-yaipr ⁇ -5-2,6-lutidine.
  • the mixture is boiled for 2 hours, the mixture is filtered, and the mother solution is evaporated to 150 ml, acidification is added to the center and ⁇ vanya and sour 2, they fertilize and the fallen-out crystalline garden of the brown color is filtered and dried.
  • the emerging plant is filtered, washed with soil and dried on the filter.
  • Example 13 30 To dissolve 1.08 g of sodium methylate in 20 ml of methanol, add 1.08 g (5 mm ⁇ l 2, 4-di ⁇ l ⁇ -6-diazoacetylpyrsh. temperature of the reaction mixture 0-5 ° C. After 4 hours The fluffy garden is filtered, washed with methanol, dried on the filter and 35 steelized from benzol. il ⁇ sh ⁇ shlid ⁇ for 0.33 g ($ 75) ⁇ .pl. ⁇ 38- ⁇ 40 ° C. ⁇ aG ⁇ . . . - 28 - money C 39, 67; ⁇ 2.29. C 7 ⁇ 5 C 4 0 2 C ⁇ . Calculated $: From 39.53; ⁇ 2.35.
  • Example 16 ehlhydraz ⁇ -6-diaz ⁇ -acetylshrimidine, obtained in example 15, is boiled in 10 ml of benz ⁇ l in the presence of active bath ⁇ sh ⁇ -
  • P ⁇ she ⁇ 20 A polycrystalline layer of 8-str ⁇ -2-diazacetyl ⁇ in ⁇ line is applied over barite paper at a concentration of 1.6 mg/sg.
  • Stability and image coloring are similar to those indicated in Example 19.
  • Barite paper is coated with a photosensitive layer containing 2-diazacetylquinine at a concentration of 3.5 MU/S ⁇ .
  • Example 23 Between two quartz layers, a polycrystalline layer of 2,4-bis-diacetylshridine with a thickness of 1.5-2.5 m is applied from the solution.
  • the resulting images are black in color on a faint yellow background.
  • the image is stable when stored in the dark - density decline for 6 months is not observed - 31 - gave.
  • the half-life of the incidence of occultness is 5 days.
  • Example 26 A polycrystalline layer of 2,6-bis-diazoacetyl-3-sh ⁇ -pyridine pr ⁇ and a concentration of 2.5 mg / s ⁇ is applied to a plate of ⁇ £ and ⁇ € W ⁇ -254.
  • Example 27 Between two quartz plates, a polycrystalline layer of 2,4-dichl ⁇ -6-diazacetyl shrimidine with a thickness of 2.0-2.7 m ⁇ is applied from the stratum of the v ⁇ a.
  • the resulting images are bright-colored on a faint yellow background. The choice is stable - 32 - earlier in the dark - falling in the dark for 6 months there were no sightings. When it is stored in diffuse daylight, the duration of the fall of ⁇ n ⁇ astn ⁇ sti is 25 days. 5
  • the resulting images are bright-
  • a light-sensitive layer is applied to baritone paper by the method of pouring, including 3-* ⁇ enyl-4-diazoacetylside ⁇ n in ⁇ l ⁇ me pr and ⁇ concentration 0.95 mg/cm.
  • the applied layer dries.
  • the obtained sample is used as an actinometer for measuring

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)
  • Pyridine Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Quinoline Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Plural Heterocyclic Compounds (AREA)
PCT/SU1981/000079 1980-12-26 1981-12-25 Derives (alpha)-diazoacetyle de nitrures aromatiques heterocyliques et materiau sensible a la lumiere WO1982002258A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP82500892A JPS57502259A (en:Method) 1980-12-26 1981-12-25
NL8120511A NL8120511A (nl) 1980-12-26 1981-12-26 Alfa-diazoacetylderivaten van aromatische, stikstofhoudende heterocyclische verbindingen en fotogevoelig materiaal.

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
SU3217545801226 1980-12-26
SU803217545A SU1232666A1 (ru) 1980-12-26 1980-12-26 3-Фенил-4-диазоацетилсиднон в качестве светочувствительного компонента в актинометрах УФ-излучени
SU3217544 1980-12-26
SU3217542 1980-12-26
SU3217542 1980-12-26
SU3217543 1980-12-26
SU3217544 1980-12-26
SU3217543 1980-12-26

Publications (1)

Publication Number Publication Date
WO1982002258A1 true WO1982002258A1 (fr) 1982-07-08

Family

ID=27484904

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/SU1981/000079 WO1982002258A1 (fr) 1980-12-26 1981-12-25 Derives (alpha)-diazoacetyle de nitrures aromatiques heterocyliques et materiau sensible a la lumiere

Country Status (6)

Country Link
JP (1) JPS57502259A (en:Method)
CH (1) CH651023A5 (en:Method)
DE (1) DE3152651T (en:Method)
NL (1) NL8120511A (en:Method)
SE (1) SE8204755L (en:Method)
WO (1) WO1982002258A1 (en:Method)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3486899A (en) * 1965-12-13 1969-12-30 Minnesota Mining & Mfg Imagewise photochromic responsive element and process
US4184874A (en) * 1974-02-05 1980-01-22 Fuji Photo Film Co., Ltd. Photosensitive composition containing chelate compound
US4220708A (en) * 1977-07-22 1980-09-02 Heller Harold G Photochromic compounds

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3486899A (en) * 1965-12-13 1969-12-30 Minnesota Mining & Mfg Imagewise photochromic responsive element and process
US4184874A (en) * 1974-02-05 1980-01-22 Fuji Photo Film Co., Ltd. Photosensitive composition containing chelate compound
US4220708A (en) * 1977-07-22 1980-09-02 Heller Harold G Photochromic compounds

Also Published As

Publication number Publication date
CH651023A5 (de) 1985-08-30
JPS57502259A (en:Method) 1982-12-23
DE3152651T (de) 1983-02-10
SE8204755D0 (sv) 1982-08-18
NL8120511A (nl) 1982-11-01
SE8204755L (sv) 1982-08-18

Similar Documents

Publication Publication Date Title
US4220708A (en) Photochromic compounds
CA1331107C (en) Colour photothermographic elements
NL8004876A (nl) Organische zeldzame aardmetaalzoutfosfor.
CN113087732A (zh) Bodipy固体荧光染料及在荧光全息防伪高亮膜上的应用
EP0530369B1 (en) Crystal comprising indolinospirobenzothiopyran derivative and ring-opening isomer thereof
WO1982002258A1 (fr) Derives (alpha)-diazoacetyle de nitrures aromatiques heterocyliques et materiau sensible a la lumiere
US3772284A (en) Azirine compounds
US4923792A (en) Color photothermographic elements
Arakawa et al. Photochromism. Synthesis and properties of indolinospirobenzothiopyrans
US5403702A (en) Crystals consisting of an indolinospirobenzopyran derivative
JP3084079B2 (ja) ロフィン誘導体
JP3200649B2 (ja) 遷移金属スピロベンゾピラン錯体、その製造方法及び該錯体からなるフォトクロミック材料
JPH03261781A (ja) ジアリールエテン化合物
EP0529100B1 (en) Indolinospirobenzopyran derivative
JPH04506348A (ja) ビピリジル、その製造方法及びその使用方法
JPH07285931A (ja) 新規化合物
JP2502067B2 (ja) ２−ヒドロキシ−３−カルバモイルベンゾ〔ａ〕カルバゾ−ル誘導体及びその製造方法
CN112409357B (zh) 一种新型功能氮杂环化合物及其制备方法与应用
JPH02238061A (ja) ヒドロキシフロリン系化合物及びこれを用いた光吸収材料
JPH06293772A (ja) 新規化合物
JPS63227597A (ja) ビス（ジチオベンジル）ニツケル錯体化合物
SU1608191A1 (ru) Способ получени 1,3,3-триметилиндолин-2-спиро-2 @ -/2Н/селенопирано /5,6- @ / пиразола
SU666170A1 (ru) Производные анилидов ароилуксусных кислот,обладающие свойствами защищаемых желтых компонент в цветных негативных кинофотоматериалах
SU721429A1 (ru) Способ получени оксазолилзамещенных толанов
JP2876239B2 (ja) ベンゾセレナゾリン系スピロピラン化合物

Legal Events

Date Code Title Description
AK Designated states

Designated state(s): AT CH DE JP NL SE US

ENP Entry into the national phase

Ref document number: 1981 9093

Country of ref document: AT

Date of ref document: 19820708

Kind code of ref document: A

RET De translation (de og part 6b)

Ref document number: 3152651

Country of ref document: DE

Date of ref document: 19830210

WWE Wipo information: entry into national phase

Ref document number: 3152651

Country of ref document: DE