CA2030883A1 - Chemiluminescent solution based on substituted anthracene - Google Patents

Chemiluminescent solution based on substituted anthracene

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Publication number
CA2030883A1
CA2030883A1 CA002030883A CA2030883A CA2030883A1 CA 2030883 A1 CA2030883 A1 CA 2030883A1 CA 002030883 A CA002030883 A CA 002030883A CA 2030883 A CA2030883 A CA 2030883A CA 2030883 A1 CA2030883 A1 CA 2030883A1
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CA
Canada
Prior art keywords
bis
compound
fluorescer
composition
composition according
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.)
Abandoned
Application number
CA002030883A
Other languages
French (fr)
Inventor
Andre Van Moer
Jacques Ladyjensky
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.)
Wyeth Holdings LLC
Original Assignee
American Cyanamid Co
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Filing date
Publication date
Application filed by American Cyanamid Co filed Critical American Cyanamid Co
Publication of CA2030883A1 publication Critical patent/CA2030883A1/en
Abandoned legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/235—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring and to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C43/247—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring and to a carbon atom of a ring other than a six-membered aromatic ring containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
    • C07C25/18—Polycyclic aromatic halogenated hydrocarbons
    • C07C25/22—Polycyclic aromatic halogenated hydrocarbons with condensed rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
    • C07C43/29—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings containing halogen
    • 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
    • C09K11/07—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials having chemically interreactive components, e.g. reactive chemiluminescent compositions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
    • C07C2603/24—Anthracenes; Hydrogenated anthracenes

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Luminescent Compositions (AREA)
  • Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Chemical Or Physical Treatment Of Fibers (AREA)
  • Physical Water Treatments (AREA)
  • Breeding Of Plants And Reproduction By Means Of Culturing (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

31,306 CHEMILUMINESCENT SOLUTION BASED ON SUBSTITUTED ANTHRACENE

ABSTRACT OF THE INVENTION

New derivatives of anthracene for the emission of a blue chemiluminescent light are disclosed. The derivatives are of 9,10-bisphenylanthracene substituted at the 2 position of the anthracene ring and on the phenyl groups.
The production of turquoise chemiluminescent light is also disclosed by mixing said derivatives with a green 9,10-bis(phenylethynyl)anthracene.

Description

- - 2~3~883 TITLE OF THE INVENTION
CHEMILUMINESCENT SOLUTION BASED ON SUBSTITUTED ANTHRACENE

~ackground of The Invention The principle techniques for the production of chemiluminescent light have been described in great detail in U.S. Patent No. 4,678,608 which is incorporated herein by reference.
Chemiluminescence is produced by a reaction, in the liquid phase, of an activator such as hydrogen peroxide with a fluorescent agent and an oxalate. Optionally, other secsndary compounds can be present such a catalysts, dyes etc.
Until recently, there existed no slmple means for the production of pure blue chemiluminescent light to the satis~action o~ the user, the convent~onally used fluorescent dye to obtain a blue color being 9,10-dlphenylanthracene. U.S. Patent 4,717,511 reveals, however, the use of a well-defined product, 9,10-bis(4-methoxyphenyl)-2-chloroanthracene, which produces a better light yield, as well as more pure blue color.

SUMMARY OF THE INVENTION
Unexpectedly, it has now been discovered that other derivatives of anthracene allow an equivalent or better yield of light emission (number of lumens-h/L) while at the same time still producing a similar, or even a more pure, blue color. Other advantages have also been often observed, for example, with regard to the ease of synthesis and purification.
In addition, lt has been ob erved that chemiluminescent solutions prepared with fluorescers which are derivatives of 9,10-diphenylanthracenes substituted according to the present invention, when mixed with a green chemiluminescent solution based on a conventional 2~30~3 fluorescent dye 9,10-~bis(phenylethnyl)anthracene, unexpectedly produce solutions with a turquoise color which remains stable over time, a color whic~ was not thought to be achievable before.

DESCRIPTION OF T~ INVENTION
INCLUDING PREFERRED EMBODIMENTS
The new derivatives of anthracene according to the invention are prepared by a method, according to the reaction scheme given below, by aroylat~on of phthalic anhydride, with a 2-phenyl derivative under Friedel-Crafts reaction conditions i.e. using AlC13 followed by cyclization in, for example, sulfuric acid. The Grignard reagent, (R')nPhMgBR, is then added at 9,10 to the resultant anthraquinone and hydrolysis is then effected with ammonium chloride ~Cl-C4). The resultant hydrolyzed product is then reduced with potassium iodide, active acid and sodium hypophosphite under reflux condition~ to form the resultant derivative which is isolated by filtering, washing with water, drying, dissolving in benzene and filtering after the addition of activated charcoal.
In th~ structural formulae, R represents a fluoro, chloro, bromo, alkoxy (Cl_C4), or phenoxy subsitutent.
(R')n represents one or more identical or different groups, said ~roups being alkoxy (Cl_C4), phenoxy, fluoro, or polyalXylenoxy alkyl ether of 3-18 carbon atoms, n being 1-3, inclusive, except that when R is chloro, R' is not p-methoxy.

2~3~8~3 Re~ction Scheme O
¢~ ~ AlC13 ~.H

1~ ~llgEir ¢~11 )n 2) NH4Cl/H20 ~ a KI 9 NaH2P02 1~. R~ ) n CH3COOH ~/ refl~lx ~a')n ~, ~ R~ )n ,, 2~3~

The following ~xamples are set forth for purposes of illustration only, except as set forth in the appended claims. All parts and percentages are by weight unless otherwise specified.

Example A
(Substituted Anthraquinones) ~ fluorobenzene, 2) m-bromobenzene and 3) m-methoxybenzene, respectively, are added to phthalic anhydride under Freidel-Crafts reaction conditions using AlC13 to produce the corresponding o-aroylbenzoic acids.
Ths acids are cyclized with sulfuric acid to yield the corresponding anthraquinones wh~ch are then recrystallized from a 2:1 benzene/ethanol mixture. 2-Chloranthraquinone is commercially available.

Example B
(Anthracenediols) 0.2 Mol aliquots of the anthraquinones from Examples 1-3, above, are each added slowly to the Grignard Reagent tR')n-phenyl magnesium bromide, the R' being 4-ethoxy, 3,4-dimethoxy (n=2), 4-fluoro and 4-phenoxy, respectively, (said Reagents having been produced by reacting one mole of R' phenylBr and 2 mols of magnesium in 2 liters of dry tetrhydrofuran under a nitrogen atmosphere (excess magnesium being removed by filtration under nitrogen gas) and heated under reflux for 2 hours. The resultant reaction mixture is then hydrolyzed after cooling to room temperature with 200 ml of a 10% ammonium chloride solution. The tetrahydrofuran is evaporated off and the resultant residue is then extracted three items with 500 ml of hot benzene followed by drying over magnesium sulfate, filtering and evaporating again to produce the corresponding anthracenediols.

2~3~83 Example c (9,10-Bisphenylanthracenes) 100 parts of each the anthracenediols of Example B are heated with re~lex in 1500 mls. o~ glacial acetic acid for 5 hours with 200 parts of sodium iodide and 200 parts of sodium hypophosphite. The volume of acetic acid is brought to about 500 mls and one liter of water is then added to the reaction media. The resultant mixture is then filtered and washed 3 times with 500 mls. of water. After drying, the desired product is d~ssolYed in benzene and filtered after the addition of activated charcoal. Solvent is eliminated in a rotary evaporator and the product is recrylstallized from a 1:1 benzene/ethanol mixture. Aftar filtrat~onj the crystals obtained are rinsed with 200 mlæ of ether and dried at 50C for 10 hours and purified.

Examples 1-9 Utilizing the above procedures of ~xamples A-C, the following compounds are obtained, with the yields of anthracenediol and the final product being shown in parentheses:
Example 1 9,10-bis(4-ethoxyphenyl)-2-chloroanthracene (87%, 80%) Example 2 9,10-bis~4-ethoxyphenyll-2-~luoroanthracene (84%, 79%) Examle 3 9,10-bis(4-ethoxyphenyl)-2-bromoanthracene (84%, 79%) Exam~le 4 9,10-bis(4-ethoxyphenyl)-2-methoxyanthracene (82%, 80%) Example 5 9,10-bis(4-dimethoxyphenyl)-2-chloroanthracene (83~, 82%) Example 6 9,10-bis(3,4-dimethoxyphenyl)-2-fluroanthracene (83%, 82%) 2a30883 Exa~ple 7 9,10-bis(4-fluorophenyl)-2-chloroanthracene (80%, 78%) Exam~le 8 9,10-bis(4-fluorophenyl)-2-fluoroanthracene (78%, 80%) Exam~le 9 9,10-bis~4-phenoxyphenyl)-2-chloroanthracene (80%, 81~) Exam~le 10 Triethyleneglycol monomethyl ether is chlorinated with thionyl chloride. The chlorinated product is then reacted with sodium p bromophenolats to produce 4-bromo(monomethyl-ethertriethylene glycoloxy) benzene which is then reacted with 2-chloroanthracene as per Exampla B, above. Example C
$s then followed to produce the resultant 9,10-bis[4-(monomethylethertriethyleneglycoloxyphenol)]-2-chloroanthracene (75%, 80%).
To produce chemiluminescence light, the compounds according to the present invention are used under the condition~ already described in the literature, particularly in said U.S. Patent No. 4,678,608. In general, one can use any known solvent or oxalate which can be used for the production of chemiluminescent light. The solvent can be an ester, aromatic derivatives or a chlorinated hydrocarbon.
Pre~erably, phthalates are used, in particular dibutyl phthalate.
Oxalates, such as those described in U.S. Patent Nos.
3,749,679 and 3,846,316, incorporated herein by reference, may be used to produce the chemical reaction to cause chemiluminescent light when mixed with the fluorescers described above, with bis(2,4,5-trichloro-6-carbopentoxyl-phenyl) oxalate being exemplary. Substituted carbalkoxy-phenyl oxalates are the preferred class of oxalates used herein, the oxalate and fluorescer each being used in sufficient quantity to cause chemiluminescent light, preferably in a 20-40:1 oxalate to fluorescer, molar ratio.

203~o~3 The blue fluorescer is used in amounts ranging from about 0.005 mole per liter of oxalate solution i.e. the solvent solution of the oxalate and the fluorescer.
Useful catalysts are disclosed in U.S. Patent No.
3,775,336, incorporated herein by reference, in concentrations disclosed therein, and usually in the solvent solution o~ the hydrogen peroxide.
The areas of application are well known and they include the production of useful ob;ects, particularly signs, decorative ob~ects, games and gadgets. In such articles, the chemiluminescent light is produced by mixing a solution o~ an activator, in general oxygenated water (hydrogen peroxide), with a solution which contains the novel fluorescers hereof and an oxalate diester. The article con~ists of, in its paqsive state, two compartments between which a communicating is established at the time of use, for example as described in French Patent No. 87 112g6.
for the case of ~lexible luminescent tubes.

Example 11 a) Into a suitable vessel are charged 90 parts of 2,4,5-trichloro-6-carbopentoxyphenyl oxalate. The volume is increased with dibutyphthalate and heated to 150C under nitrogen. While stirring, there is added approximately 1 part Or the fluorescer of Example 1, when the temperature reaches 90C.
b) 50 parts of 85% hydrogen peroxide are added to an 80/20 solution of dimethylphthalate/t-butanol, to bring the volume to lL. Next, there is added 0.180 part of sodium salicylate.
c) The solutions prepared in a) and b) are then mixed in a volume proportion of 3 to 1. The result is a chemiluminescent emission of a particularly pure blue.

2~30883 Following the procedures of Example 11 except that the fluorescers of Examples 2-10 are used, similar results are ob-tained.

FURTHER EMBODIMENTS
In addition, it has been found that it is possible to produce compositions containing two fluorescers which are adapted to be reacted with hydrogen peroxide to provide chemiluminescent light of a color different than that emitted by either fluorescer alone.
More particularly, a composition comprising a mixture of two fluorescers, each emitting a different color when used in a chemi-luminescent composition, is prepared by mixing said fluorescers in amounts such as to produce a third color when the resultant compo-sition is mixed with a peroxide. Specifically, the compounds described above and having the structure of Formula IV emit a blue light upon activation with hydrogen peroxide in chemiluminescent systems. Similarly, the known fluorescer, 9,10-bis(phenylethynyl) anthracene emits a green light under the same conditions.
However, when the blue and green fluorescers are blended into a composition, the color emitted by activation with hydrogen perox-ide is turquoise. Similarly, a red fluorescer can be blended with the blue fluorescer hereof to give pink. The red fluorescer of our copending Canadian application No. 2,019,152 filed on June 18th, 1990 can be used for this purpose. This feature forms part of the scope of the invention set forth herein. The shade of the 2~30~83 61109-7811 different color achieved can be obtained by varying the concentration of either fluorescer. Thu~, from about 95:5 to about 5:95 parts of either fluorescer can be used.
- 8a-~030~3 Example 21 A solvent solution of the blue fluorescer of Example 1 is mixed with 1,6,7,12-tetraphenoxy-N,N'-bis(2,6-diisopropyl-phenyl)-3,4,9, 10-perylene dicarboximide in an amount of 91:9, respectively. A peak color is observed upon activation of the solvent mixture with a hydrogen peroxide solution.

Example 22 The procedure of Example 21 is again followed except that the two fluorescers are that of Example 8 and 9,10-bis(phenylethynyl)anthracene and the ratio of fluorescers is 73:27. The cvlor emitted i~ turquoise.

_ g

Claims (17)

1. A compound having the formula:
wherein R is fluoro, chloro, bromo, alkoxy (C1-C4), or phenoxy, (R') is one or more identical or different groups, selected from alkoxy (C1-C4), phenoxy, fluoro, or polyalkylenoxy alkyl ether groups (C1-C4), and n is 1-3, inclusive, except that when R is chloro, R' is not p-methoxy.
2. A compound according to Claim 1 selected from the group consisting of:

9,10-bis(4-ethoxyphenyl)-2-chloroanthracene;
9,10-bis(4-ethoxyphenyl)-2-fluoroanthracene;
9,10-bis(4-ethoxyphenyl)-2-bromoanthracene;
9,10-bis(4-ethoxyphenyl)-2-methoxyanthracene;
9,10-bis(4-dimethoxyphenyl)-2-chloroanthracene;
9,10-bis(3,4-dimethoxyphenyl)-2-fluoroanthracene;
9,10-bis(4-fluorophenyl)-2-chloroanthracene;
9,10-bis(4-fluorophenyl)-2-fluoroanthracene;
9,10-bis(4-phenoxyphenyl)-2-chloroanthracene;
9,10-bis(4-(monomethylethertriethyleneglycoloxyphenyl)-2-chloroanthracene.
3. A compound according to Claim 1, wherein both R
and R' is fluoro.
4. A compound according to Claim 1, wherein R is chloro and R' is phenoxy.
5. A composition adapted to be reacted with hydrogen peroxide to provide chemiluminescent light, said composition containing a compound of Claim 1.
6. A composition adapted to be reacted with hydrogen peroxide to provide chemiluminescent light, said composition containing a compound of Claim 2.
7. A composition according to Claim 5 wherein both R
and R' is fluoro.
8. A composition according to Claim 5 wherein R is chloro and R' is phenoxy.
9. A composition according to Claim 5 comprising, in addition thereto, a solvent for said compound.
10. A composition according to Claim 5 comprising, in addition thereto, an oxalate compound.
11. A composition according to Claim 10 wherein said oxalate is a substituted carbalkoxyphenyl oxalate.
12. A composition according to Claim 11 wherein said oxalate is bis(2,4,5-trichloro-6-carbopentoxyphenyl) oxalate.
13. A composition according to Claim 9 wherein said solvent is t-butylphthalate.
14. A method of producing chemiluminescent light which comprises adding to the composition of Claim 10, a solution of hydrogen peroxide.
15. A composition adapted to be reacted with hydrogen peroxide to provide chemiluminescent light of a color different than that emitted by either fluorescer alone comprising a mixture of two fluorescers in concentrations such as to produce said different color.
16. A composition according to Claim 15 wherein one fluorescer is a compound according to Claim 1 and the other fluorescer is 9,10-bis(phenylethynyl)anthracene.
17. A composition according to Claim 15 wherein one fluorescer is a compound according to Claim 1 and the other fluorescer is a perylene dicarboximide.
CA002030883A 1989-11-28 1990-11-26 Chemiluminescent solution based on substituted anthracene Abandoned CA2030883A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
BE08901272 1989-11-28
BE8901272A BE1003403A7 (en) 1989-11-28 1989-11-28 SUBSTITUTED ANTIHRACENE-BASED CHEMILUMINESCENT SOLUTION.

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US (1) US5232635A (en)
EP (1) EP0429821B1 (en)
JP (1) JPH03178942A (en)
KR (1) KR910009623A (en)
AT (1) ATE174318T1 (en)
BE (1) BE1003403A7 (en)
CA (1) CA2030883A1 (en)
DE (1) DE69032818T2 (en)
ES (1) ES2126550T3 (en)
FI (1) FI905837A (en)
GR (1) GR3029468T3 (en)
HK (1) HK1014531A1 (en)
IL (1) IL96002A0 (en)
MX (1) MX23463A (en)
NO (1) NO905101L (en)
PT (1) PT95994A (en)

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US7028687B1 (en) 1999-08-26 2006-04-18 Precious Life, Llc Escape hood
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US6884447B2 (en) 2001-06-04 2005-04-26 Brad Baker Confectionery with body, handle and container
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US7252893B2 (en) 2004-02-17 2007-08-07 Eastman Kodak Company Anthracene derivative host having ranges of dopants
US20080128666A1 (en) * 2005-12-13 2008-06-05 Crayola, Llc Chemiluminescent system
US20070134513A1 (en) * 2005-12-13 2007-06-14 Binney & Smith Chemiluminescent system
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KR101427588B1 (en) * 2007-06-14 2014-08-08 삼성디스플레이 주식회사 Liquid crystal composition and liquid crystlal display device having the same
KR100974125B1 (en) * 2008-05-14 2010-08-04 주식회사 두산 A method for manufacturing asymmetric anthracene derivatives and application for oled device using the same
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US20130168620A1 (en) 2011-12-30 2013-07-04 Maggilume, LLC Chemiluminescent system
US11581487B2 (en) 2017-04-26 2023-02-14 Oti Lumionics Inc. Patterned conductive coating for surface of an opto-electronic device
US11751415B2 (en) 2018-02-02 2023-09-05 Oti Lumionics Inc. Materials for forming a nucleation-inhibiting coating and devices incorporating same
CN113785411B (en) 2019-03-07 2023-04-11 Oti照明公司 Material for forming nucleation inhibiting coatings and apparatus incorporating the same

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BE1003403A7 (en) 1992-03-17
JPH03178942A (en) 1991-08-02
NO905101D0 (en) 1990-11-26
HK1014531A1 (en) 1999-09-30
ES2126550T3 (en) 1999-04-01
ATE174318T1 (en) 1998-12-15
EP0429821A2 (en) 1991-06-05
MX23463A (en) 1993-09-01
DE69032818D1 (en) 1999-01-21
US5232635A (en) 1993-08-03
EP0429821A3 (en) 1993-01-13
FI905837A (en) 1991-05-29
PT95994A (en) 1991-09-13
IL96002A0 (en) 1991-07-18
DE69032818T2 (en) 1999-04-29
EP0429821B1 (en) 1998-12-09
KR910009623A (en) 1991-06-28
NO905101L (en) 1991-05-29
FI905837A0 (en) 1990-11-27
GR3029468T3 (en) 1999-05-28

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