IP Library Granted Patent US 9,115,306
Granted Patent B2
US 9,115,306 · App. 14/294,058 · Granted Aug 25, 2015

Low temperature oxalate systems and methods for chemiluminescent reactions

Inventors: Earl Cranor (Longmeadow, MA); Linda Jacob (Woodbridge, CT); Patrick Taylor (Holyoke, MA)
Assignee: Cyalume Technologies, Inc.
C09K11/07C09K11/025G01N21/76C09K2211/1007C09K2211/1018
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Quick Facts
Patent No.
US 9,115,306
App. No.
14/294,058
Granted
Aug 25, 2015
Kind
B2
Abstract

In some embodiments, the instant invention provides a chemiluminescent system, including: an oxalate system, including: (a) at least one oxalate ester in an amount ranging from 3 to 60 percent by weight based on a total weight of the oxalate system, (b) at least one first solvent selected from the group consisting of: alkyl benzoates, dialkyl phthalates, trialkyl acetylcitrates, 2-acetyloxy isobutyrates, paraffinic liquids, isoparaffinic liquids, toluene, nitroethane, in an amount ranging from 10 to 97 percent by weight based on the total weight of the oxalate system, (c) at least one second solvent is selected from the group consisting of: dialkyl malonates, dialkyl dialkylmalonates, dialkyl arylalkylmalonates, dialkyl succinates, dialkyl glutarates, dialkyl adipates, dialkyl pimelates, dialkyl polyalkylmalonates, (d) at least one fluorescer, and (e) at least one inorganic salt in an amount ranging from 0.1 to 30 percent by weight based on the total weight of the oxalate system.

Claims (19)

1. A chemiluminescent system, comprising:

an oxalate system, comprising:

(a) at least one oxalate ester in an amount ranging from 3 to 60 percent by weight based on a total weight of the oxalate system,

(b) at least one first solvent selected from the group consisting of: alkyl benzoates, dialkyl phthalates, trialkyl acetylcitrates, 2-acetyloxy isobutyrates, paraffinic liquids, isoparaffinic liquids, toluene, nitroethane, and a combination thereof;

wherein the at least one first solvent is present in an amount ranging from 10 to 97 percent by weight based on the total weight of the oxalate system,

(c) at least one second solvent is selected from the group consisting of: dialkyl malonates, dialkyl dialkylmalonates, dialkyl arylalkylmalonates, dialkyl succinates, dialkyl glutarates, dialkyl adipates, dialkyl pimelates, dialkyl polyalkylmalonates, and a combination thereof;

wherein the at least one second solvent is present in an amount ranging from 10 to 97 percent by weight based on the total weight of the oxalate system,

(d) at least one fluorescer, and

(e) at least one inorganic salt in an amount ranging from 0.1 to 30 percent by weight based on the total weight of the oxalate system,

wherein a viscosity of the chemiluminescent system does not exceed 130,000 cP; and

wherein a combination of the at least one first solvent and the at least one second solvent is present in a sufficient amount in the chemiluminescent system so as to result the chemiluminescent system, at a temperature ranging from −110 degrees Celsius to −10 degrees Celsius, producing a light having an illuminescence between 0.1 lx and 35,000 lx.

2. The chemiluminescent system of claim 1 , wherein the at least one oxalate ester is represented by formula (I):

wherein R═CH 2 A, and A is selected from the group consisting of an alkyl chain, alkyl ring, an aromatic ring, and a combination thereof,

wherein R is linear or branched, and

wherein R is from C 4-15 .

3. The chemiluminescent system of claim 1 , wherein the at least one oxalate ester is selected from the group consisting of: bis{3,4,6-trichloro-2-[(2-methylpropoxy)carbonyl]phenyl}oxalate, bis{3,4,6-trichloro-2-[(cyclopropylmethoxy)carbonyl]phenyl}oxalate, bis{3,4,6-trichloro-2-[(2-methylbutoxy)carbonyl]phenyl}oxalate, bis{3,4,6-trichloro-2-[(3-methylbutoxy)carbonyl]phenyl}oxalate, bis{3,4,6-trichloro-2-[(2,2-dimethylpropoxy)carbonyl]phenyl}oxalate, bis{3,4,6-trichloro-2-[(2-methylpentyloxy)carbonyl]phenyl}oxalate, bis{3,4,6-trichloro-2-[(3-methylpentyloxy)carbonyl]phenyl}oxalate, bis{3,4,6-trichloro-2-[(4-methylpentyloxy)carbonyl]phenyl}oxalate, bis{3,4,6-trichloro-2-[(3,3-dimethylbutoxy)carbonyl]phenyl}oxalate, bis{3,4,6-trichloro-2-[(2-ethylbutoxy)carbonyl]phenyl}oxalate, bis{3,4,6-trichloro-2-[(cyclopentylmethoxy)carbonyl]phenyl}oxalate, bis{3,4,6-trichloro-2-[(2-methylhexyloxy)carbonyl]phenyl}oxalate, bis{3,4,6-trichloro-2-[(3-methylhexyloxy)carbonyl]phenyl}oxalate, bis{3,4,6-trichloro-2-[(4-methylhexyloxy)carbonyl]phenyl}oxalate, bis{3,4,6-trichloro-2-[(5-methylhexyloxy)carbonyl]phenyl}oxalate, bis{3,4,6-trichloro-2-[(cyclohexylmethoxy)carbonyl]phenyl}oxalate, bis{3,46-trichloro-2-[(phenylmethoxy)carbonyl]phenyl}oxalate, bis{3,4,6-trichloro-2-[(2-phenylethoxy)carbonyl]phenyl}oxalate, bis(3,4,6-trichloro-2-{[(2-methylphenyl)methoxy]carbonyl}phenyl)oxalate, bis(3,4,6-trichloro-2-{[(3-methylphenyl)methoxy]carbonyl}phenyl)oxalate, bis(3,4,6-trichloro-2-{[(4-methylphenyl)methoxy]carbonyl}phenyl)oxalate, bis(3,4,6-trichloro-2-{[(2,3-dimethylphenyl)methoxy]carbonyl}phenyl)oxalate, bis(3,4,6-trichloro-2-{[(2,4-dimethylphenyl)methoxy]carbonyl}phenyl)oxalate, bis(3,4,6-trichloro-2-{[3,4-dimethylphenyl)methoxy]carbonyl}phenyl)oxalate, bis(3,4,6-trichloro-2-{[(3,5-dimethylphenyl)methoxy]carbonyl}phenyl)oxalate, bis(3,4,6-trichloro-2-{[(2,6-dimethylphenyl)methoxy]carbonyl}phenyl)oxalate, bis(3,4,6-trichloro-2-{[(2-ethylphenyl)methoxy]carbonyl}phenyl)oxalate, bis(3,4,6-trichloro-2-{[(3-ethylphenyl)methoxy]carbonyl}phenyl)oxalate, bis(3,4,6-trichloro-2-{[(4-ethylphenyl)methoxy]carbonyl}phenyl)oxalate, bis(3,4,6-trichloro-2-{[2-(2-methylphenyl)ethoxy]carbonyl}phenyl)oxalate, bis(3,4,6-trichloro-2-{[2-(3-methylphenyl)ethoxy]carbonyl}phenyl)oxalate, bis(3,4,6-trichloro-2-{[2-(4-methylphenyl)ethoxy]carbonyl}phenyl)oxalate, bis{3,4,6-trichloro-2-[(2-phenylpropoxy)carbonyl]phenyl}oxalate, bis{3,4,6-trichloro-2-[(3-phenylpropoxy)carbonyl]phenyl}oxalate, bis{3,4,6-trichloro-2-[1-naphthalenylmethoxy)carbonyl]phenyl}oxalate, bis{3,4,6-trichloro-2-[2-naphthalenylmethoxy)carbonyl]phenyl}oxalate, bis{3,4,6-trichloro-2-[(2,2-diphenylethoxy)carbonyl]phenyl}oxalate, bis{3,4,6-trichloro-2-[(9-fluorenylmethoxy)carbonyl]phenyl}oxalate, and bis{3,4,6-trichloro-2-[(9-anthracenylmethoxy)carbonyl]phenyl}oxalate.

4. The chemiluminescent system of claim 1 , wherein the at least one fluorescer is selected from the group consisting of: 1-methoxy-9,10-bis(phenylethynyl)anthracene, perylene, rubrene, 16,17-didecycloxyviolanthrone, 2-ethyl-9,10-bis(phenylethynyl)anthracene; 2-chloro-9,10-bis(4-ethoxyphenyl)anthracene, 2-chloro-9,10-bis(4-methoxyphenyl)anthracene, 9,10-bis(phenylethynyl)anthracene, 1-chloro-9,10-bis(phenylethynyl)anthracene, 1,8-dichloro-9,10-bis(phenylethynyl)anthracene, 1,5-dichloro-9,10-bis(phenylethynyl)anthracene, 2,3-dichloro-9,10-bis(phenylethynyl)anthracene, 5,12-bis(phenylethynyl)tetracene, 9,10-diphenylanthracene, 1,6,7,12-tetraphenoxy-N,N′-bis(2,6-diisopropylphenyl)-3,4,9,10-perylene dicarboximide, 1,6,7,12-tetraphenoxy-N,N′ bis(2,5-di-t-butylphenyl)-3,4,9,10-perylene dicarboximide, 1,7-dichloro-6,12-diphenoxy-N,N′-bis(2,6-diisopropylphenyl)-3,4,9,10-perylene dicarboximide, 1,6,7,12-tetra(p-bromophenoxy)-N,N′-bis(2,6-diisopropylphenyl)-3,4,9,10-perylene dicarboximide, 1,6,7,12-tetraphenoxy-N,N′dineopentyl-3,4,9,10-perylene dicarboximide, 1,6,7,12-tetra-(p-t-butylphenoxy)-N,N′-dineopentyl-3,4,9,10-perylenedicarboximide, 1,6,7,12-tetra(o-chlorophenoxy)-N,N′-bis(2,6-diisopropylphenyl)-3,4,9,10-perylene dicarboximide; 1,6,7,12-tetra(p-chlorophenoxy)-N,N′-bis(2,6-diisopropylphenyl)-3,4,9,10-perylene dicarboximide, 1,6,7,12-tetra(o-fluorophenoxy)-N,N′-bis(2,6-diisopropylphenyl)-3,4,9,10-perylene dicarboximide, 1,6,7,12-tetra(p-fluorophenoxy)-N,N′-bis(2,6-diisopropylphenyl)-3,4,9,10-perylenedicarboximide, 1,6,7,12-tetraphenoxy-N,N′-diethyl-3,4,9,10-perylene dicarboximide, 1,7-dibromo-6,12-diphenoxy-N,N′-bis(2-isopropylphenyl)-3,4,9,10-perylene dicarboximide, 16,17-dihexyloxyviolanthrone, and 1,4-dimethyl-9,10-bis(phenylethynyl)anthracene.

5. The chemiluminescent system of claim 1 , the at least one inorganic salt is selected from the group consisting of: sodium thiosulphate, potassium thiosulphate, cobalt acetate, copper acetate, lead acetate, cupric chloride, ferric chloride, calcium iodide, potassium iodide, and silver nitrate.

6. The chemiluminescent system of claim 1 , wherein the at least one fluorescer is present in an amount ranging from 0.05 to 0.9 percent by weight based on the total weight of the oxalate system.

Assignments (4)
NOTICE OF GRANT OF SECURITY INTEREST IN PATENTS Recorded Jul 13, 2022
From: CYALUME TECHNOLOGIES, INC.
To: PNC BANK, NATIONAL ASSOCIATION, AS ADMINISTRATIVE AGENT
Reel/Frame 060639/0564 →
RELEASE OF SECURITY INTEREST Recorded May 4, 2022
From: TWIN BROOK CAPITAL PARTNERS, LLC
To: CYALUME TECHNOLOGIES, INC.
Reel/Frame 059811/0891 →
SECURITY INTEREST Recorded Oct 26, 2018
From: CYALUME TECHNOLOGIES, INC.
To: TWIN BROOK CAPITAL PARTNERS, LLC, AS ADMINISTRATIVE AGENT
Reel/Frame 047324/0313 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 4, 2015
From: CRANOR, EARL; JACOB, LINDA; TAYLOR, PATRICK
To: CYALUME TECHNOLOGIES, INC.
Reel/Frame 034888/0715 →
Continuity (5)
Provisional Application 61830075 · Jun 1, 2013
Provisional Application 61830071 · Jun 1, 2013
Provisional Application 61830072 · Jun 1, 2013
Provisional Application 61830070 · Jun 1, 2013
Related Publication 20140353560A1 · Dec 4, 2014