Composition comprising stabilized phosphorus compounds

Details Composition comprising stabilized phosphorus compounds Composition comprising stabilized phosphorus compounds

2000-04-12

2002-01-15

McAvoy, Ellen M. (Department: 1764)

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

Organic compounds

Phosphorus esters

C252S387000, C252S388000

Reexamination Certificate

active

06339168

ABSTRACT:

The present invention relates to a composition comprising stabilized phosphorus compounds and the use of this composition for increasing the shelf life or reducing metal corrosion.
The use of phosphorus compounds is usually associated with the problem that firstly they only have a short shelf life and secondly that they are so aggressive that they corrode metals. The short shelf life and the high tendency to cause corrosion of metals of the preferably organic phosphorus compounds leads to them being difficult to transport over long distances, particularly when they are handled industrially. Furthermore, the storage of phosphorus compounds for a prolonged period of time is associated with considerable technical difficulties. However, the economically satisfactory use of organic phosphorus compounds in industry generally makes it necessary to transport them in containers of an economically acceptable size, for example in railroad tank cars. Furthermore, phosphorus compounds are usually processed in continuous processes with other materials to give new products, in which case the phosphorus compounds have to be fed in over a long period and therefore have to be stored appropriately.
It is an object of the present invention to provide compositions comprising phosphorus compounds which have both a long shelf life and a low tendency to corrode metals.
We have found that this object is achieved by a composition comprising at least one phosphorus compound and at least one stabilizer compound having one of the formulae I to IV:
where
R
1
, R
2
are each, independently of one another, a hydrogen atom, a C
1
-C
10
-alkyl radical, a C
6
-C
12
-aryl radical, a C
7
-C
13
-aralkyl radical or a C
7
-C
13
-alkylaryl radical,
a, b are, independently of one another, from 1 to 5,
c, d are, independently of one another, from 0 to 10;
where
R
3
is a hydrogen atom, a C
1
-C
10
-alkyl radical, a C
6
-C
12
-aryl radical, a C
7
-C
13
-aralkyl radical or a C
7
-C
13
-alkylaryl radical,
e is from 1 to 4,
f is from 1 to 100;
where
R
4
, R
13
are, independently of one another, NCO or NHCOOR′, where R′ is an alkyl polyether glycol or a C
1
-C
20
-alcohol,
R
5
, R
6
, R
7
, R
8
, R
9
, R
10
, R
11
, R
12
are each, independently of one another, a hydrogen atom, a C
1
-C
10
-alkyl radical, a C
6
-C
12
-aryl radical, a C
7
-C
13
-aralkyl radical or a C
7
-C
13
-alkylaryl radical,
g is from 0 to 5,
h is from 1 to 100;
where
R
14
, R
15
, R
16
are each, independently of one another, a hydrogen atom or
where R
17
is a hydrogen atom, a C
1
-C
10
-alkyl radical, a C
6
-C
12
-aryl radical, a C
7
-C
13
-aralkyl radical or a C
7
-C
13
-alkylaryl radical,
i is from 2 to 8,
j is from 1 to i−k
k is from 0 to j, where j+k≦i,
denotes the C—N bond to the nitrogen heterocycle of the formula IV,
or (CH
2
)
1
—N═C═O, where 1 is from 1 to 20.
According to the present invention, R
1
and R
2
are preferably each, independently of one another, a C
1
-C
10
-alkyl radical, particularly preferably a C
1
-C
4
-alkyl radical and more preferably a C
3
-alkyl radical. Among these, a 2-propyl radical is particularly preferred.
The integral variables a and b are preferably each, independently of one another, 1, 2, 3 or 4 and particularly preferably 2. When a and b are each 2, the corresponding radicals R
1
and R
2
are each located on the carbon atom next to the carbon at which the NCN group is attached to the benzene ring.
Among the C
6
-C
12
-aryl radicals, C
6
-C
10
-aryl radicals are preferred and C
6
-C
8
-aryl radicals are particularly preferred according to the present invention. Among the abovementioned aryl radicals, phenyl and naphthyl radicals are very particularly preferred. Preferred aralkyl radicals having preferably from 7 to 14 carbon atoms are tolyl, xylyl, tert-butylphenyl and di-tert-butylphenyl. As alkylaryl radical, preference is given to one having from 7 to 14 carbon atoms, and benzyl is particularly preferred.
According to the present invention, the variables c and d are preferably, independently of one another, 0, 1, 2, 3, 4 or 5 and particularly preferably 0, 1 or 2. Further preference is given to the case where c and d are each 0.
As regards the preferred meanings of the radical R
3
, what has been said above about the radicals R
1
and R
2
applies.
The integral variable e is preferably 1, 2 or 3 and particularly preferably 3. When the variable e is 3, it is preferred that the radicals R3 are each bound to the carbon atoms of the benzene ring which are next to those to which a nitrogen is bound.
The integral variable f is preferably in the range from 1 to 50 and particularly preferably in the range from 1 to 20.
R′ is preferably derived from a C
1
-C
10
-alcohol and particularly preferably from a C
2
-C
5
-alcohol. Among these alcohols, preference is in turn given to ethanol, n-propanol, isopropanol, n-butanol, isobutanol, tert-butanol, n-pentanol and isopentanol, with ethanol being particularly preferred.
If R′ is an alkyl polyether glycol, preference is given to C
1
-C
10
-alkyl polyether glycols and particular preference is given to C
1
-C
5
-alkyl polyether glycols. Among these, preference is in turn given to methyl, ethyl, propyl and isopropyl polyether glycols and particular preference is given to methyl polyether glycols. The alkyl polyether glycols preferably have a molecular weight in the range from 1000 to 1,000,000 g/mol, preferably from 1500 to 100,000 g/mol and particularly preferably from 2000 to 10,000 g/mol.
As regards the preferred meanings of R
5
, R
6
, R
7
, R
8
, R
9
, R
10
, R
11
and R
12
, what has been said above regarding R
1
and R
2
applies, except that a methyl radical rather than the 2-propyl radical is particularly preferred.
The integral variable g is preferably 0, 1, 2, 3 and particularly preferably 0. The variable h is preferably 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10 and particularly preferably 2, 3, 4, 5 or 6.
The radicals R
14
, R
15
and R
16
are preferably not hydrogen atoms.
As regards R
17
, what has been said regarding R
5
to R
12
likewise applies. The integral variable i is preferably 3, 4 or 5 and particularly preferably 5, so that a cyclohexyl ring is formed with the carbon via which the cyclic radical is bound to the nitrogen of the heterocycle. Preference is also given to the variable i being 1.
In the case of a cyclohexyl ring being formed, the integral variable k is preferably 4. In this case, it is in turn preferred that in each case two of the four radicals R
17
are bound to a carbon of the cyclohexyl ring and are separated from the further carbon likewise bearing two radicals R
17
by a carbon atom located in between.
A preferred embodiment of the composition of the present invention contains from 0.01 to 20% by weight, preferably from 0.01 to 5% by weight, in particular from 0.05 to 2% by weight, based on the composition, of at least one stabilizer compound.
In another preferred embodiment, the composition of the present invention contains from 99.99 to 80% by weight, based on the composition, of at least one phosphorus compound.
Phosphorus compounds preferred according to the present invention have from 6 to 120, preferably from 6 to 80 and particularly preferably from 8 to 40, carbon atoms.
All phosphorus compounds known to a person skilled in the art are possible for the composition of the present invention. Among these, particular preference is given to organic phosphorus compounds which are used industrially or have a short shelf life or a high tendency to cause corrosion or both. Among these organic phosphorus compounds, particular preference is given to those of the formula (V).
where
R
18
, R
19
and R
20
are each, independently of one another, an alkyl radical, an aryl radical, an alkylaryl radical, an arylalkyl radical or a cycloalkyl radical having from 7 to 40 carbon atoms or a cycloalkyl radical having from 5 to 40 carbon atoms;
x is a sulfur or oxygen atom, preferably an oxygen atom;
m, n, o are, independently of one another, 0 or 1, preferably 0.
In one embodiment of the phosphorus comp

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