Hyperbranched compounds with a tetrafunctional central group...

Details Hyperbranched compounds with a tetrafunctional central group... Hyperbranched compounds with a tetrafunctional central group...

2001-02-20

2003-02-04

Wu, David W. (Department: 1713)

Chemistry of hydrocarbon compounds

Compound or reaction product mixture

C106S316000, C260S001000, C524S080000

Reexamination Certificate

active

06515192

ABSTRACT:

The present invention relates to a novel hyperbranched compound having a tetrafunctional central group. The present invention additionally relates to a novel process for preparing hyperbranched compounds. The present invention further relates to the use of the novel hyperbranched compound as a functional component in multisubstance mixtures and for preparing dendrimers of higher generations.
Hyperbranched compounds and dendrimers containing a tetrafunctional central group are known from the patent WO 93/17060. The central group used is a tetrol such as pentaerythritol, ditrimethylolpropane, diglycerol and ditrimethylolethane. However, the corresponding hyperbranched compounds are too viscous and too poorly soluble for numerous end uses. For example, it is impossible to prepare particularly high-solids coating compositions, adhesives or sealing compounds in solution or dispersion in aqueous or organic media using the known hyperbranched compounds. Additionally, the liquid coating compositions, adhesives or sealing compounds which comprise the known hyperbranched compounds as functional components are too viscous for the majority of application technologies. Accordingly, powder coating materials and powder slurries comprising known hyperbranched compounds have film formation temperatures which in many cases are too close to the crosslinking temperature.
It is an object of the present invention to find novel hyperbranched compounds which no longer have the disadvantages of the prior art and which make it possible to prepare new coating compositions, adhesives and sealing compounds which have advantageously low viscosities even at high solids content or in the melt. A further object of the present invention is to find a novel process for preparing hyperbranched compounds which allows such compounds to be obtained in a particularly simple way. Another object of the present invention is to find novel end uses for hyperbranched compounds, especially as functional components in multisubstance mixtures and for preparing dendrimers of higher generations.
Accordingly, we have found the novel hyperbranched compounds having a tetrafunctional central group of the general formula I
C[—A
q
—X—]
m
[—A
r
—X—]
n
[—A
s
—X—]
o
[—A
t
—X—]
p
  (I),
in which the indices and variables have the following meanings:
 
m+n+o+p
=4; where
m=an integer from 1 to 3 and
n, o and p=0 or an integer from 1 to 3;
q, r, s and t=an integer from 1 to 5, where q>r, s, t;
X=—O—, —S—or —NH—;
A=—CR
2
—; where
R=—H, —F, —Cl, —Br, —CN, —NO
2
, C
1
-C
3
alkyl or C
1
-C
3
haloalkyl or C
1
-C
3
alkoxy radical or,
 if q, r, s and/or t=at least 2, a C
2
-C
4
alkanediyl and/or C
2
-C
4
oxaalkanediyl radical which bridges 2 to 5 carbon atoms, and/or an oxygen atom —O—, which bridges 3 to 5 carbon atoms, of the radical —A—.
In the text below, the novel hyperbranched compounds having a tetrafunctional central group of the general formula I are referred to for brevity as “compounds of the invention”.
The tetrafunctional central groups of the general formula I are referred to below for brevity as “central groups I”.
Accordingly, the novel process for preparing the compounds of the invention is referred to below as the “process of the invention”.
Similarly, in the text below, the novel multisubstance mixtures which comprise the compounds of the invention are referred to as “multisubstance mixtures of the invention”, in particular as “coating compositions of the invention”, “adhesives of the invention”, or “sealing compounds of the invention”.
The novel dendrimers of higher generations which can be prepared using the compounds of the invention are referred to below as “dendrimers of the invention”
In the light of the prior art it is surprising that the object of the present invention was able to be achieved with the aid of the compounds of the invention. In particular, it was not expected that varying the central group, sometimes referred to as an initiator group in the prior art, would have such far-reaching technical consequences.
The essential constituent of the compounds of the invention is the central group I.
In the general formula I, the indices m, n, o and p add up to 4. The index m is always larger than 0 and stands for an integer from 1 to 3, in particular 1.
While observing the above boundary condition, the indices n, o and p have the value 0 or represent an integer from 1 to 3. This means that it is not possible for each of these indices to adopt the value 0.
In accordance with the invention, the following combinations of values in the indices are of advantage:
m=1 and n, o, p=1;
m=1, n=2, o, p=1;
m=1, n=2, o=1 and p=0;
m=1, n=3, o, p=0;
m=2, n=1, o=1 and p=0;
m=2, n=2 and o, p=0;
m=3, n=1 and o, p=0.
Of these, particular advantage is possessed by those numerical combinations in which m=1.
In the general formula I, the indices q, r, s and t denote integers from 1 to 5. In this case the index q is always larger than the indices r, s and t. Accordingly, the index q has a value of at least 2.
In accordance with the invention, the following numerical combinations of the indices are of advantage:
q=2, r, s and/or t=1;
q=3, r, s and/or t=1 and/or 2;
q=4, r, s and/or t=1, 2 and/or 3;
q=5, r, s and/or t=1, 2, 3 and/or 4.
The variable —X— in the general formula I denotes divalent oxygen atoms —O— or sulfur atoms —S— or a secondary amino group —NH—. In accordance with the invention it is advantageous if —X— is —O—.
The variable —A— in the formula I denotes a divalent radical —CR
2
—.
The radical R therein represents hydrogen atoms —H, fluorine atoms —F, chlorine atoms —Cl, bromine atoms —Br, nitrile groups —CN, nitro groups —NO
2
, C
1
-C
3
alkyl or C
1
-C
3
haloalkyl groups or C
1
-C
3
alkoxy groups. Examples of suitable groups of this kind are methyl, ethyl, propyl, trifluoromethyl, trichloromethyl, perfluoroethyl, perfluoropropyl, methoxy, ethoxy or propoxy groups.
Of advantage in accordance with the invention are hydrogen atoms or methyl groups, which are therefore used for preference. In particular, hydrogen atoms are used. Accordingly, the variables —A— particularly preferred in accordance with the invention comprise methylene groups.
If in the general formula I at least one of the indices q, r, s and/or t represents at least the number 2, the radical R may also represent a C
2
-C
4
alkanediyl radical and/or oxaalkanediyl radical which cyclically bridges from 2 to 5 carbon atoms of the radical —A—. Alternatively, the radical —R— may represent an oxygen atom —O— which cyclically bridges from 3 to 5 carbon atoms of the radical —A—. Formed as a result are cyclopentane-1,2- or 1,3-diyl groups, tetrahydrofuran-2,3-, -2,4-, -2,5- or -3,4-diyl groups, cyclohexane-1,2-, -1,3- or -1,4-diyl groups, or tetrahydropyran-2,3-, -2,4-, -2,5- or -2,6-diyl groups, but not epoxide groups.
Examples of central groups I which are especially advantageous in accordance with the invention are derived formally, therefore, from the tetrols (III1) to (III10) described below by abstracting the four hydrogen atoms of the hydroxyl groups.
Of these, the central group I which derives from the tetrol (III1) (2,2-bishydroxymethyl-1,4-butanediol; homopentaerythritol) is very particularly advantageous and is therefore used with very particular preference in accordance with the invention.
In the compounds of the invention, the above-described variables —X— are connected by way of spacer groups to in each case one reactive functional group. In the context of the present invention, the term “reactive functional group” refers to a group which, in contrast to an inert group, is readily available for further reactions. Accordingly, the group in question may comprise any desired group known from organic chemistry. In

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