US3622581A - Perinones - Google Patents

Perinones Download PDF

Info

Publication number
US3622581A
US3622581A US795506*A US3622581DA US3622581A US 3622581 A US3622581 A US 3622581A US 3622581D A US3622581D A US 3622581DA US 3622581 A US3622581 A US 3622581A
Authority
US
United States
Prior art keywords
product
parts
diperinone
phosphors
red
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
Application number
US795506*A
Other languages
English (en)
Inventor
Edward E Jaffe
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
HEUBACH Inc A DE CORP
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
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
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Application granted granted Critical
Publication of US3622581A publication Critical patent/US3622581A/en
Assigned to HEUBACH INC., A DE CORP. reassignment HEUBACH INC., A DE CORP. ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: E.I. DU PONT DE NEMOURS AND COMPANY
Assigned to IRVING TRUST COMPANY reassignment IRVING TRUST COMPANY SECURITY INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: HEUBACH INC.
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/22—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains four or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • C09B57/12—Perinones, i.e. naphthoylene-aryl-imidazoles
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/22—Luminous paints
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials

Definitions

  • ATTORNEY TEMPERATURE PERINONILS This invention relates to organic phosphors which are excited by long wavelength ultraviolet light and respond with a bright red emission.
  • the luminescent materials commonly used as thin layers on the inside of fluorescent lamps, high-pressure mercury vapor lamps and sign tubings are generally referred to as fluorescent powders or phosphors. These are invariably inorganic in nature, and some of the best and most widely publicized are expensive. Under the circumstances, the possibility of utilizing organic compounds for similar purposes should be considered. Heretofore there has been no organic candidate which showed sufficient response under the conditions of use to render it of interest.
  • the compound of this invention exhibit fluorescence when excited by 2537A. radiation; the exciting radiation in the usual fluorescent lamps, and by the 3660A. radiation which constitutes an appreciable proportion of the emission within mercury vapor lamps.
  • the phosphors also are useful in pigment form. Other useful applications of the discovery will occur to the artisan.
  • FIG. l shows the fluorescent spectrum for a diperinone compound of the invention, having thereon a prior art spectrum for comparison purposes.
  • the wave length of fluorescent emission is plotted against arbitrary intensity units, the spectrum indicated as A being that of a diperinone of this invention, and B being that for one of the best currently available red phosphors.
  • FIG. 2 shows a graph on which intensity of fluorescent emission in arbitrary units is plotted against temperature.
  • Naphthalic anhydride is sulfonated according to the method of Anselm and Zuckmayer (Ber. 32. 3283 1899)):
  • the diperinone derivative is prepared by an intermolecular; dehydrobromination of 2 mols of the perinone, thereby forming a compound of this invention, that is, one of compounds 1, II, and III hereinbefore identified.
  • the product is purified by recrystallization from acid as follows: Asolution of 2.63 parts of the pulverized dry product in 18.4 parts of l00'pe rce n,t sulfuric acid is prepared by stirring at a temperature not above C. After solution is complete, as judged by microscopic examination of a sample, the acid concentration is gradually lowered to 90 percent by dropwise addition of water, the rate being such as to maintain the temperature of the mixture below 10 C. throughout. The mixture is stirred for an additional hour at 10 C., and the precipitated sulfate of the desired product is filtered and thoroughly washed with 80 percent sulfuric acid.
  • the sulfate filter cake is then hydrolyzed with ice and water, and the resulting diperinone compound isolated by filtration and washing free of acid to give 1.01 parts of red shade yellow solid.
  • 1.26 parts of the product is extracted twice with 450 parts of nitrobenzene and once with 570 parts of boiling N,N-dimethyl formamide. The purified sample does not melt up.to"4'00 C.
  • FIG. I shows a comparison of the fluorescent emission spectrum (A) of the product obtained with one of thebestcurrently available red phosphors'(y Eu,, VOl).
  • B under excitation by relatively long ultraviolet radiation(3660A). Intensities are on a qualitative scale. Visual observation confirms the appreciably greater brightness of the product of this invention. It is concluded that such strong, deep red emission under excitation at 3660A.
  • FIG. 11 shows the relative intensity of the fluorescent emission spectrum of the product at temperatures up to 300 C. It will be noted that even though the intensity decreases by approximately 40 percent at 300 C. by comparison with that at C. as shown in FIG. 11 where the intensity of emission in arbitrary units is plotted versus temperature, it is still higher than that of Y Eu VO See FIG. 1, assuming that the emission intensity ofthe latter were constant throughout this temperature range. Consequently, the product of this invention would be expected to be a superior red phosphor for color-correction of discharge devices excited by light of 3660A. even at the higher temperature.
  • the product of this invention is a red-shade yellow material which is extremely insoluble in common organic solvents.
  • an organic. vehicle for example lithographic varnish
  • it is a redshade yellow pigment which luminesces strongly upon stimulation by ultraviolet radiation. After exposure for 72 hours some darkening occurs, but most of the luminescence is still retained. Even after dilution of the dispersion with ZnO (1:100) some luminescence is observed on shining ultraviolet light on the extended dispersion.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Luminescent Compositions (AREA)
US795506*A 1969-01-31 1969-01-31 Perinones Expired - Lifetime US3622581A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US79550669A 1969-01-31 1969-01-31

Publications (1)

Publication Number Publication Date
US3622581A true US3622581A (en) 1971-11-23

Family

ID=25165695

Family Applications (1)

Application Number Title Priority Date Filing Date
US795506*A Expired - Lifetime US3622581A (en) 1969-01-31 1969-01-31 Perinones

Country Status (6)

Country Link
US (1) US3622581A (xx)
BE (1) BE744660A (xx)
DE (1) DE2004316A1 (xx)
FR (1) FR2037058A1 (xx)
GB (1) GB1249603A (xx)
NL (1) NL7001119A (xx)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4001628A (en) * 1976-02-25 1977-01-04 Westinghouse Electric Corporation Low-pressure fluorescent discharge device which utilizes both inorganic and organic phosphors

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2998402A (en) * 1957-10-29 1961-08-29 Sandoz Ag Process for dyeing and coloring in the mass with perlyene derivatives
US3306904A (en) * 1963-10-26 1967-02-28 Hoechst Ag Vat dyestuffs of the anthraquinone series and process for their manufacture

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2998402A (en) * 1957-10-29 1961-08-29 Sandoz Ag Process for dyeing and coloring in the mass with perlyene derivatives
US3306904A (en) * 1963-10-26 1967-02-28 Hoechst Ag Vat dyestuffs of the anthraquinone series and process for their manufacture

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4001628A (en) * 1976-02-25 1977-01-04 Westinghouse Electric Corporation Low-pressure fluorescent discharge device which utilizes both inorganic and organic phosphors

Also Published As

Publication number Publication date
GB1249603A (en) 1971-10-13
DE2004316A1 (de) 1970-10-01
FR2037058A1 (xx) 1970-12-31
NL7001119A (xx) 1970-08-04
BE744660A (fr) 1970-07-20

Similar Documents

Publication Publication Date Title
Chandross et al. Chemiluminescent electron-transfer reactions of radical anions
Qi et al. Exploring highly efficient light conversion agents for agricultural film based on aggregation induced emission effects
GB2128985A (en) Organic rare-earth salt phosphors
US3505240A (en) Phosphors and their preparation
US4401585A (en) Bis(p-alkylphenylethynyl)anthracene
He et al. A strong red-emitting carbazole based europium (III) complex excited by blue light
Clar et al. Circobiphenyl and the attempted synthesis of 1: 14, 3: 4, 7: 8, 10: 11-tetrabenzoperopyrene
US3622581A (en) Perinones
Drew et al. 132. Chemiluminescent organic compounds. Part IV. Amino-and hydrazino-cyclo phthalhydrazides and their relative luminescent power
US3186950A (en) Rare earth tungstate and molybdate luminophors
US2366179A (en) Amino triphenylacetonitrile and a process of making it
US1936716A (en) Nitrogenous vat dyestuffs
US3335137A (en) Process of manufacturing substituted 2-(21-arylsulphonyl aminophenyl)-4h, 3, 1-benzoxazin-4-ones
Tran et al. Carboxylate BODIPY integrated in MOF-5: easy preparation and solid-state luminescence
US2730504A (en) Tin activated barium phosphate phosphor
CN115466404B (zh) 一种同核稀土配位聚合物白光材料的制备及应用
US3817990A (en) Triazole brighteners
SU668274A1 (ru) Производные имидазо (1,2- @ ) тетрагидробенз-1,2,4-триазина в качестве люминофоров
CN114773618B (zh) 一种稀土-有机荧光和闪烁材料的制备方法及应用
US2042683A (en) Vat dyestuffs of the anthraquinone series and process of making same
RU1816787C (ru) N-карбоксиметилимид 4-карбоксиметиламинонафталевой кислоты в качестве люминофора зеленого свечени и способ его получени
US3047577A (en) Process for the production of dyestuffs and dyestuff intermediates
Irick Jr et al. Yellow to Red Methine Dyes Derived From 1, 3-lndandione.
SU825523A1 (ru) 4-о-
US2226512A (en) Luminescent material

Legal Events

Date Code Title Description
AS Assignment

Owner name: HEUBACH INC., A DE CORP.

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:E.I. DU PONT DE NEMOURS AND COMPANY;REEL/FRAME:004273/0247

AS Assignment

Owner name: IRVING TRUST COMPANY, NEW YORK

Free format text: SECURITY INTEREST;ASSIGNOR:HEUBACH INC.;REEL/FRAME:004348/0764

Effective date: 19841213

Owner name: IRVING TRUST COMPANY, 1290 AVENUE OF THE AMERICAS,

Free format text: SECURITY INTEREST;ASSIGNOR:HEUBACH INC.;REEL/FRAME:004348/0764

Effective date: 19841213