Substituted ammonium salt of 1,5′-bitetrazole

Details Substituted ammonium salt of 1,5′-bitetrazole Substituted ammonium salt of 1,5′-bitetrazole

1999-07-23

2001-10-09

Miller, Edward A. (Department: 3641)

Organic compounds -- part of the class 532-570 series

Organic compounds

Four or more ring nitrogens in the bicyclo ring system

C149S036000, C544S196000, C544S336000, C544S358000, C544S410000, C548S251000

Reexamination Certificate

active

06300498

ABSTRACT:

BACKGROUND OF THE INVENTION
The present invention relates to novel 1,5′-bitetrazole compounds and processes for their production.
The present invention also relates to gas generating agents containing the 1,5′-bitetazole compounds.
The present invention further relates to foaming agents for precision molding of resins, foaming agents for reducing weight of molded articles, smoking agents for effectively diffusing chemicals such as agricultural chemicals or insecticides, and air bag gas generating agents.
It is difficult td mold crystalline resins into the shape defined by a mold, since they crystallize and shrink upon cooling after molding. Conventionally, for precision molding of crystalline resins, apparent shrinkage is empirically inhibited by using specially devised molds, which, however, cannot accomplish complete precision molding. Accordingly, additional techniques for further reducing shrinkage of molded articles are employed, which include physical blowing of gas into the core portion of molded articles (Japanese Examined Patent Publications Nos. 41264/1973 and 14968/1982), and addition of chemical foaming agents (Japanese Unexamined Patent Publications Nos. 129563/1975, 12864/1978 and 61435/1981, and U.S. Pat. No. 4,871,861). In conventional techniques, azodicarbonamide (ADCA) has been used widely for a long period of time, mainly for foam molding of resins.
ADCA, although utilized widely as a gas generating agent, is not wholly satisfactory for use in precision molding or high-foam molding for weight reduction, because it has too broad a decomposition temperature range relative to the molding temperature and causes air bubbles on the surface of molded articles, which impair the appearance. Moreover, decomposition gases and residues of ADCA contain toxic substances such as ammonia, biurea or isocyanuric acid, and thus are harmful to humans and animals and the environment. Further, the decomposition residue contaminates molds, decreasing the molding efficiency and yield of molded articles.
To solve the above problems, use of tetrazoles as gas generating agents was proposed. Tetrazoles, which decompose completely, are free from the above problems. However, since high decomposability means low stability, tetrazoles are highly sensitive to friction or other physical factors, lacking handling safety.
Further, although air bag gas generating agents and smoking agents are required to be harmless to humans and animals, safe, and odorless, conventional air bag gas generating agents and smoking agents do not fully satisfy these requirements.
SUMMARY OF THE INVENTION
An object of the invention is to provide a novel 1,5′-bitetrazole compound which is highly sensitive only to temperature and which decomposes sharply, i.e., decomposes in a narrow temperature range, and generates a nontoxic gas.
Another object of the invention is to provide a gas generating agent which is highly sensitive only to temperature and which decomposes sharply and generates a nontoxic gas.
The present inventors did extensive research to achieve the above objects and directed their attention to 1,5′-bitetrazole which leaves substantially no residue upon decomposition. They found that ammonia or amine can be used to reduce the physical sensitivities of 1,5′-bitetrazole. The present invention has been accomplished based on this novel finding.
The present invention provides the following 1,5′-bitetrazole, processes for their production, and gas generating agents containing the.
1. A 1,5′-bitetrazole represented by the formula (1):
wherein Tz
31
represents
R
1
, R
2
and R
3
are the same or different and each represent a hydrogen atom; C
1-10
alkyl which may be substituted by amino, di(C
1-4
alkyl)amino, C
1-8
alkoxy, hydroxy or phenyl; C
3-20
alkenyl; phenyl; —C(═NH)NH
2
; —C(═NH)NHNH
2
; —C(═NH)NHCN; triazolyl; amino; carbamoyl; triazinyl which may be substituted by amino and methyl; —NHCS;
or —R
4
—NH
3
+
Tz
−
wherein Tz
−
is as defined above, R
4
represents a single bond, C
2-6
alkylene, phenylene, —CO— or
when R
1
is a hydrogen atom, R
2
and R
3
may be taken together with the nitrogen atom to which they are attached to form a 5- to 7-membered saturated heterocycle; when R
1
is a hydrogen atom, R
2
and R
3
may be taken together to form
and R
1
, R
2
and R
3
may be taken together to form
2. A process for producing a 1,5′-bitetrazole amine salt according to Item 1 comprising the step of reacting 1,5′-bitetrazole or its alkali salt with ammonia or an or its carbonate or halide, the amine being represented by the formula:
R
5
R
6
R
7
N  (2)
wherein R
5
, R
6
and R
7
are the same or different and each represent a hydrogen atom; C
1-10
alkyl which may be substituted by amino, di(C
1-4
alkyl)amino, C
1-8
alkoxy, hydroxy or phenyl; C
3-20
alkenyl; phenyl; —C(═NH)NH
2
; —C(═NH)NHNH
2
; —C(═NH)NHCN; triazolyl; amino; carbamoyl; triazinyl which may be substituted by amino and methyl; —NHCS;
or —R
8
—NH
2
wherein R
8
represents a single bond, C
2-6
alkylene, phenylene, —CO— or
when R
5
is a hydrogen atom, R
6
and R
7
may be taken together with the nitrogen atom to which they are attached to form a 5- to 7-membered saturated heterocycle; when R
5
is a hydrogen atom, R
6
and R
7
may be taken together to form
and R
5
, R
6
and R
7
may be taken together to form
3. A gas generating agent containing a 1,5′-bitetrazole according to Item 1.
4. A foaming agent for molding resins, which contains a 1,5′-bitetrazole according to Item 1.
5. An air bag gas generating agent containing a 1,5′-bitetrazole according to Item 1.
6. A smoking agent for diffusing chemicals, which contains a 1,5′-bitetrazole according to Item 1.
The 1,5′-bitetrazole amine salt of the invention comprises 1,5′-bitetrazole, and ammonia or an amine.
Useful amines include monomethylamine, monoethylamine, n-propylamine, isopropylamine, n-butylamine, sec-butylamine, t-butylamine, n-hexylamine, n-octylamine, 2-ethylhexylamine, oleylamine, allylamine, 3-dimethylaminopropylamine, 3-dibutylaminopropylamine, 3-methoxypropylamine, 3-ethoxypropylamine, 2-ethylhexyloxypropylamine, methyliminobispropylamine, cyclohexylamine, aniline, benzylamine, phenethylamine, dicyandiamide, guanidine, aminoguanidine, aminotriazole, monoethanolamine and like primary monoamines; ethylenediamine, hexamethylenediamine, phenylenediamine, xylenediamine, xylylenediamine, acetoguanamine, hydrazine, urea, carbohydazide, thiocarbohydrazide, N-acetyl-m-phenylenediamine, 2,4-diamino-6-methyl-symtriazine, 1,4-bis(3-aminopropyl)piperazine and like primary diamines; melamine and like primary triamines; dimethylamine, diethylamine, dicyclohexylamine, di-2-ethylhexylamine, diethanolamine, piperazine, piperidine, diphenylamine and like secondary monoamines or secondary diamines; and trimethylamine, triethylamine, N,N,N′,N′-tetramethylethylenediamine, hexamethylenetetramine, pyridine, N,N-dimethylaniline, N,N-dimethylcyclohexyl-amine, triethanolamine and like tertiary amines.
The process for producing the novel 1,5′-bitetrazole of the invention comprises the steps of dissolving 1,5′-bitetrazole or its alkali metal salt in water, an alcohol (preferably a C
1-3
alcohol) or dimethylformamide (DMF), and adding ammonia or the above amine or its carbonate or halide in an equivalent amount relative to the 1,5′-bitetrazole or its alkali metal salt, followed by stirring. When an alkali metal salt of 1,5′-bitetrazole and an amine halide are used, it is preferable to select such a combination that the alkali metal halide produced as a byproduct is soluble in water, alcohol or DMF, so that 1,5′-bitetrazole can be easily obtained by collecting crystals by filtration.
The reaction is carried out at preferably 0 to 100° C., more preferably 20 to 60° C., for a period of preferably 0.5 to 10 hours, more preferably 1 to 3 hours.
The 1,5′-bitetrazole is a novel substance which has low

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