US3496111A - Chemiluminescent smokes - Google Patents
Chemiluminescent smokes Download PDFInfo
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- US3496111A US3496111A US561337A US3496111DA US3496111A US 3496111 A US3496111 A US 3496111A US 561337 A US561337 A US 561337A US 3496111D A US3496111D A US 3496111DA US 3496111 A US3496111 A US 3496111A
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- US
- United States
- Prior art keywords
- aluminum
- water
- smoke
- chemiluminescent
- amine
- 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
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- 239000000779 smoke Substances 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 19
- 150000001412 amines Chemical class 0.000 description 18
- 229910052782 aluminium Inorganic materials 0.000 description 12
- 235000010210 aluminium Nutrition 0.000 description 12
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 12
- 125000005234 alkyl aluminium group Chemical group 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 9
- -1 aluminum compound Chemical class 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 6
- 239000004312 hexamethylene tetramine Substances 0.000 description 6
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 6
- CBXRMKZFYQISIV-UHFFFAOYSA-N 1-n,1-n,1-n',1-n',2-n,2-n,2-n',2-n'-octamethylethene-1,1,2,2-tetramine Chemical group CN(C)C(N(C)C)=C(N(C)C)N(C)C CBXRMKZFYQISIV-UHFFFAOYSA-N 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- 239000003643 water by type Substances 0.000 description 4
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000036571 hydration Effects 0.000 description 3
- 238000006703 hydration reaction Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000005081 chemiluminescent agent Substances 0.000 description 2
- 230000000536 complexating effect Effects 0.000 description 2
- HJXBDPDUCXORKZ-UHFFFAOYSA-N diethylalumane Chemical compound CC[AlH]CC HJXBDPDUCXORKZ-UHFFFAOYSA-N 0.000 description 2
- 230000009977 dual effect Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000002171 ethylene diamines Chemical class 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 230000007928 solubilization Effects 0.000 description 2
- 238000005063 solubilization Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000581364 Clinitrachus argentatus Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229940037003 alum Drugs 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical group [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- MYBJXSAXGLILJD-UHFFFAOYSA-N diethyl(methyl)alumane Chemical compound CC[Al](C)CC MYBJXSAXGLILJD-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052754 neon Inorganic materials 0.000 description 1
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 description 1
- NDUUEFPGQBSFPV-UHFFFAOYSA-N tri(butan-2-yl)alumane Chemical compound CCC(C)[Al](C(C)CC)C(C)CC NDUUEFPGQBSFPV-UHFFFAOYSA-N 0.000 description 1
- SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C06—EXPLOSIVES; MATCHES
- C06D—MEANS FOR GENERATING SMOKE OR MIST; GAS-ATTACK COMPOSITIONS; GENERATION OF GAS FOR BLASTING OR PROPULSION (CHEMICAL PART)
- C06D3/00—Generation of smoke or mist (chemical part)
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F21—LIGHTING
- F21K—NON-ELECTRIC LIGHT SOURCES USING LUMINESCENCE; LIGHT SOURCES USING ELECTROCHEMILUMINESCENCE; LIGHT SOURCES USING CHARGES OF COMBUSTIBLE MATERIAL; LIGHT SOURCES USING SEMICONDUCTOR DEVICES AS LIGHT-GENERATING ELEMENTS; LIGHT SOURCES NOT OTHERWISE PROVIDED FOR
- F21K2/00—Non-electric light sources using luminescence; Light sources using electrochemiluminescence
- F21K2/06—Non-electric light sources using luminescence; Light sources using electrochemiluminescence using chemiluminescence
Definitions
- Chemiluminescent smokes are produced by reacting water with a composition consisting essentially of (1) an amine complex of an aluminum alkyl, and (2) a chemi luminescent agent.
- a typical aluminum alkyl complex is that produced by reacting hexamethylenetetramine with triethylaluminum; an exemplary chemiluminescent agent is tetrakis(dimethylamino)ethylene.
- This invention pertains to chemiluminescent smokes containing an alkyl aluminum and a tetrakis(di-loweralkylamino)ethylene. These smokes are visible by day and at night.
- An object of this invention which is to prepare a nightvisible smoke, is satisfied by providing compositions consisting essentially of These compositions yield chemiluminescent smoke clouds when admixed with water.
- the method of water mixing is not critical.
- the smoke agent may be injected underneath the surface of water to yield a cloud of chemiluminescent smoke above the surface of the water.
- the smoke agent can be merely admixed with water by shaking the agent and Water in a vessel.
- Another method for contacting the agent with water is to introduce a stream of the agent into a water spray.
- the water may be atmospheric, the smoke agents of this invention are sensitive to high humidity.
- One essential ingredient in the smoke compositions of this invention is an aluminum compound of the types given above.
- all alkyl radicals bonded to the aluminum atom are identical.
- these alkyl radicals are solely composed of carbon and hydrogen and have up to 4 carbon atoms.
- Typical examples of alkyl aluminums which are applicable in this invention are trimethyl aluminum, triethyl aluminum, diethylaluminum hydride, methyl diethyl aluminum, triisopropyl aluminum, tri-sec-butyl aluminum, and the like.
- the aluminum alkyl is complexed with an amine.
- amines can be employed. The exact nature of the amine is not critical provided it can complex with the aluminum compound and is devoid of substituent groups which lead to deleterious side effects.
- the amines are selected from hexamethylenetetramine and tetraloweralkyl ethylene diamines. (For the purpose of this invention, lower alky signifies alkyl radicals of one to four carbons.)
- the complexing of the alkyl aluminum with an amine is readily carried out by simply mixing the amine and the alkyl aluminum under anhydrous conditions and in States atent the presence of an inert atmosphere.
- nitrogen is used to provide the inert atmosphere.
- other inert gases such as argon and neon can be employed, if desired.
- Best results are obtained when all of the alkyl aluminum is complexed with an amine.
- a diamine at least one-half mole of amine is employed for each mole of alkyl aluminum.
- a tetramine is employed, at least one-quarter mole of amine is employed for each mole of alkyl aluminum.
- the ratio of amine to aluminum is the inverse molar ratio of the number of amine nitrogens to aluminum atoms.
- trialkyl aluminum is complexed with the amine it is then mixed with an amount of tetrakis(diloweralkylamino)ethylene which is sufficient to yield a final preparation containing from 20 to 50 weight percent of tetrakis compound.
- the mixing of the complex with the tetrakis compound is conveniently carried out using simple mixing procedures. As in the case of complexing, a slight amount of heat may be beneficial, that is, it may be desirable to heat up the mixture to a temperature within the range of 3050 C.
- the chemiluminescent smoke formulations of this invention yield smoke clouds which are visible at night when admixed with water.
- the water need not be pure; natural waters such as lake, river or sea water can be employed as can muddy or wet earth.
- the water may be chemically-bound, that is, waters of hydration.
- a compound which preferentially contains a large amount of waters of hydration is employed.
- Preferred compounds containing waters of hydration are alums. Typical alums which may be used are described on pages 196-199 of the 8th edition of Langes Handbook of Chemistry, Handbook Publishers, Inc., Saudusky, Ohio (1952).
- the tetrahydrofuran is not a critical ingredient but aids in the solubilization of the hexamethylenetetramine. Usually about one to three percent of such a solubilization agent is eflicaciously employed. Besides tetrahydrofuran, another typical solubilizing agent that can be used is dioxane. ,Similarly, many other ethers can be employed.
- the resultant smoke formulation yields a chemilumi' nescent smoke when admixed with water.
- a chemiluminescent smoke when admixed with water.
- equal volumes of agent and water when admixed together yield a chemiluminescent smoke.
- such a smoke is produced when one volume of agent is injected under the surface of approximately 10 volumes of Water without artificial stirring.
- the formulation yields a chemiluminescent smoke when 50 parts of the formula tion are added to 100 parts of [CI'2(SO4)3'K2SO424H20]
- Example 2 Example 3 Equimolar complexes of tetramethylenediamine with triethyl aluminum were prepared using the procedure of Example 1. They Were admixed with sufficient quantities of tetrakis(dimethylamino)ethylene to yield formulations containing 20, 30, 40 and 50 Weight percent of the tetrakis compound.
- Results indicate that the best smokes are produced when the concentration of the tetrakis compound is from 30 to 40 weight percent.
- Similar formulations are prepared by substitution of triisopropyl aluminum, tributyl aluminum or diethyl aluminum hydride for the triethylaluminum, tetrakis(dibutylamino)ethylene for the tetrakis(dimethylamino)ethylene, and the ethyl, propyl and butyl homologues of N,N,N',N-tetramethyl ethylenediamine for that compound.
- the smokes of this invention which are visible at night have many utilities. For example, they can be employed for marking purposes in sea rescues. Similarly, they may be used to direct artillery fire or aerial bombardments.
- compositions of this invention have a dual function. It is believed that this dual function is not accomplished by smokes and flares presently in use.
- the residue after dissemination by sublimation in water is a chemiluminescent film which floats on the surface of the water. This film is colored and typically orange. Since it is also visible in daylight, this aids in marking.
- a chemiluminescent smoke composition consisting essentially of (a) an aluminum alkyl having the formula RRR"Al wherein R, R' and R" are alkyl radicals of 1 to 4 carbon atoms, said aluminum alkyl being complexed with a chemically equivalent amount of (b) an amine selected from the class consisting of hexamethylenetetramine and N,N,N,N'-tetraloweralkyl ethylenediamines, and admixed with (c) from 20-50 weight percent of a tetrakis(di-loweralkylamino)ethylene.
- a smoke composition of claim 3 wherein said amine is hexamethylenetetramine.
- a smoke composition of claim 3 wherein said amine is N,N,N,N-tetramethyl ethylenediamine.
- a method for producing a chemiluminescent smoke comprising mixing a smoke composition of claim 1 with water.
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- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Botany (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Combustion & Propulsion (AREA)
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Description
3,496,111 CHEMILUMINESCENT SMOKES Urho A. Lehikoinen, Wayne, Mich., assignor to Ethyl Corporation, New York, N.Y., a corporation of Virginia No Drawing. Filed June 29, 1966, Ser. No. 561,337 Int. Cl. C09k 3/30, 1/02 US. Cl. 252188.3 7 Claims ABSTRACT OF THE DISCLOSURE Chemiluminescent smokes are produced by reacting water with a composition consisting essentially of (1) an amine complex of an aluminum alkyl, and (2) a chemi luminescent agent. A typical aluminum alkyl complex is that produced by reacting hexamethylenetetramine with triethylaluminum; an exemplary chemiluminescent agent is tetrakis(dimethylamino)ethylene.
This invention pertains to chemiluminescent smokes containing an alkyl aluminum and a tetrakis(di-loweralkylamino)ethylene. These smokes are visible by day and at night.
An object of this invention, which is to prepare a nightvisible smoke, is satisfied by providing compositions consisting essentially of These compositions yield chemiluminescent smoke clouds when admixed with water. The method of water mixing is not critical. The smoke agent may be injected underneath the surface of water to yield a cloud of chemiluminescent smoke above the surface of the water. Alternatively the smoke agent can be merely admixed with water by shaking the agent and Water in a vessel. Another method for contacting the agent with water is to introduce a stream of the agent into a water spray. Moreover, the water may be atmospheric, the smoke agents of this invention are sensitive to high humidity.
One essential ingredient in the smoke compositions of this invention is an aluminum compound of the types given above. Preferably, all alkyl radicals bonded to the aluminum atom are identical. Most preferably, these alkyl radicals are solely composed of carbon and hydrogen and have up to 4 carbon atoms. Typical examples of alkyl aluminums which are applicable in this invention are trimethyl aluminum, triethyl aluminum, diethylaluminum hydride, methyl diethyl aluminum, triisopropyl aluminum, tri-sec-butyl aluminum, and the like.
For the purposes of this invention the aluminum alkyl is complexed with an amine. A wide variety of amines can be employed. The exact nature of the amine is not critical provided it can complex with the aluminum compound and is devoid of substituent groups which lead to deleterious side effects. Preferably, the amines are selected from hexamethylenetetramine and tetraloweralkyl ethylene diamines. (For the purpose of this invention, lower alky signifies alkyl radicals of one to four carbons.)
The complexing of the alkyl aluminum with an amine is readily carried out by simply mixing the amine and the alkyl aluminum under anhydrous conditions and in States atent the presence of an inert atmosphere. Typically, nitrogen is used to provide the inert atmosphere. However, other inert gases such as argon and neon can be employed, if desired. Best results are obtained when all of the alkyl aluminum is complexed with an amine. When using a diamine, at least one-half mole of amine is employed for each mole of alkyl aluminum. Similarly, when a tetramine is employed, at least one-quarter mole of amine is employed for each mole of alkyl aluminum. In other words, the ratio of amine to aluminum is the inverse molar ratio of the number of amine nitrogens to aluminum atoms.
It is not necessary to employ an exactly chemiequiv-alent amount of amine and alkyl aluminum. An excess of amine or alkylaluminum can be used. It is convenient to employ up to 5 equivalents of amine for each equivalent of alkyl aluminum.
After the trialkyl aluminum is complexed with the amine it is then mixed with an amount of tetrakis(diloweralkylamino)ethylene which is sufficient to yield a final preparation containing from 20 to 50 weight percent of tetrakis compound. The mixing of the complex with the tetrakis compound is conveniently carried out using simple mixing procedures. As in the case of complexing, a slight amount of heat may be beneficial, that is, it may be desirable to heat up the mixture to a temperature within the range of 3050 C.
As pointed out above, the chemiluminescent smoke formulations of this invention yield smoke clouds which are visible at night when admixed with water. The water need not be pure; natural waters such as lake, river or sea water can be employed as can muddy or wet earth. In addition, the water may be chemically-bound, that is, waters of hydration. When using chemically-bound water, a compound which preferentially contains a large amount of waters of hydration is employed. Preferred compounds containing waters of hydration are alums. Typical alums which may be used are described on pages 196-199 of the 8th edition of Langes Handbook of Chemistry, Handbook Publishers, Inc., Saudusky, Ohio (1952).
To further illustrate the invention, the following nonlimiting examples are presented. Unless otherwise indicated, all parts are by weight.
Example 1 Weight percent Hexamethylenetetramine 13.8 Triethyl aluminum 45 Tetrakis(dimethylamino)ethylene 39.5 Tetrahydrofuran 1.8
The tetrahydrofuran is not a critical ingredient but aids in the solubilization of the hexamethylenetetramine. Usually about one to three percent of such a solubilization agent is eflicaciously employed. Besides tetrahydrofuran, another typical solubilizing agent that can be used is dioxane. ,Similarly, many other ethers can be employed.
The resultant smoke formulation yields a chemilumi' nescent smoke when admixed with water. For example, equal volumes of agent and water when admixed together yield a chemiluminescent smoke. Furthermore, such a smoke is produced when one volume of agent is injected under the surface of approximately 10 volumes of Water without artificial stirring. Thirdly, the formulation yields a chemiluminescent smoke when 50 parts of the formula tion are added to 100 parts of [CI'2(SO4)3'K2SO424H20] Example 2 Example 3 Equimolar complexes of tetramethylenediamine with triethyl aluminum were prepared using the procedure of Example 1. They Were admixed with sufficient quantities of tetrakis(dimethylamino)ethylene to yield formulations containing 20, 30, 40 and 50 Weight percent of the tetrakis compound.
Results indicate that the best smokes are produced when the concentration of the tetrakis compound is from 30 to 40 weight percent. Similar formulations are prepared by substitution of triisopropyl aluminum, tributyl aluminum or diethyl aluminum hydride for the triethylaluminum, tetrakis(dibutylamino)ethylene for the tetrakis(dimethylamino)ethylene, and the ethyl, propyl and butyl homologues of N,N,N',N-tetramethyl ethylenediamine for that compound.
The smokes of this invention which are visible at night have many utilities. For example, they can be employed for marking purposes in sea rescues. Similarly, they may be used to direct artillery fire or aerial bombardments.
An important aspect of this invention is that the smokes are visible by day and at night. Hence, they have daytime and nighttime utilities. Accordingly, the compositions of this invention have a dual function. It is believed that this dual function is not accomplished by smokes and flares presently in use. Moreover, the residue after dissemination by sublimation in water is a chemiluminescent film which floats on the surface of the water. This film is colored and typically orange. Since it is also visible in daylight, this aids in marking.
Having fully described the novel compositions of this invention, their method of preparation and their utility,
4 it is desired that the scope of this invention be solely limited by the lawful extent of the appended claims.
What is claimed is:
1. A chemiluminescent smoke composition consisting essentially of (a) an aluminum alkyl having the formula RRR"Al wherein R, R' and R" are alkyl radicals of 1 to 4 carbon atoms, said aluminum alkyl being complexed with a chemically equivalent amount of (b) an amine selected from the class consisting of hexamethylenetetramine and N,N,N,N'-tetraloweralkyl ethylenediamines, and admixed with (c) from 20-50 weight percent of a tetrakis(di-loweralkylamino)ethylene.
2. A smoke composition of claim 1 wherein the aluminum alkyl is triethyl aluminum.
3. A smoke composition of claim 2 wherein said tetrakis(di-loweralkylamino)ethylene is tetrakis(dimethylamino)ethylene.
4. A smoke composition of claim 3 wherein said amine is hexamethylenetetramine.
5. A smoke composition of claim 3 wherein said amine is N,N,N,N-tetramethyl ethylenediamine.
6. A method for producing a chemiluminescent smoke, said method comprising mixing a smoke composition of claim 1 with water.
7. A method of claim 6 wherein said water is from an alum having the formula References Cited UNITED STATES PATENTS 3,309,268 3/ 1967 Sherman 252-305 3,311,564 3/1967 Cline 252-1883 3,352,894 11/1967 Crain et a1. 260-448 OTHER REFERENCES Zeiss, Organometallic Chemistry, Reinhold Pub. Co. (1960), p. 202.
JOHN D. WELSH, Primary Examiner US. Cl. X.R.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US56133766A | 1966-06-29 | 1966-06-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3496111A true US3496111A (en) | 1970-02-17 |
Family
ID=24241529
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US561337A Expired - Lifetime US3496111A (en) | 1966-06-29 | 1966-06-29 | Chemiluminescent smokes |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3496111A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003068777A1 (en) * | 2002-02-14 | 2003-08-21 | Quimversion, S.L. | Aluminium and hexamethylenetetramine complex and the applications thereof |
| US20070079722A1 (en) * | 2003-10-21 | 2007-04-12 | The Sepron Company, L.C. | Chemiluminescent paint projectiles and method and preparation |
| WO2010000881A1 (en) * | 2008-06-30 | 2010-01-07 | Tanco Salas Jesus Maria | New gels resulting from the reaction of solutions formed by a source of aluminium having hydroxyl groups and hexamethylenetetramine with one or more additives |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3309268A (en) * | 1964-12-16 | 1967-03-14 | Louis M Sherman | Composition and method for producing smoke |
| US3311564A (en) * | 1965-11-01 | 1967-03-28 | Du Pont | Oxyluminescent compositions containing dehydrating agents |
| US3352894A (en) * | 1963-08-12 | 1967-11-14 | Phillips Petroleum Co | Process for separating organometals from 1-olefins |
-
1966
- 1966-06-29 US US561337A patent/US3496111A/en not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3352894A (en) * | 1963-08-12 | 1967-11-14 | Phillips Petroleum Co | Process for separating organometals from 1-olefins |
| US3309268A (en) * | 1964-12-16 | 1967-03-14 | Louis M Sherman | Composition and method for producing smoke |
| US3311564A (en) * | 1965-11-01 | 1967-03-28 | Du Pont | Oxyluminescent compositions containing dehydrating agents |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003068777A1 (en) * | 2002-02-14 | 2003-08-21 | Quimversion, S.L. | Aluminium and hexamethylenetetramine complex and the applications thereof |
| US20050255065A1 (en) * | 2002-02-14 | 2005-11-17 | Quimversion, S.L. | Aluminium and hexamethylenetetramine complex and the applications thereof |
| US20070079722A1 (en) * | 2003-10-21 | 2007-04-12 | The Sepron Company, L.C. | Chemiluminescent paint projectiles and method and preparation |
| WO2010000881A1 (en) * | 2008-06-30 | 2010-01-07 | Tanco Salas Jesus Maria | New gels resulting from the reaction of solutions formed by a source of aluminium having hydroxyl groups and hexamethylenetetramine with one or more additives |
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