Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2001-12-20
2003-06-10
Powers, Fiona T. (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C548S542000
Reexamination Certificate
active
06576767
ABSTRACT:
The present invention relates to a process for the preparation of condensation compounds, starting from low-molecular weight compounds which have at least two functional groups and which have been activated by means of an activating reagent. Likewise, the present invention also relates to the use of such activating reagents for the preparation of the condensation compounds.
Condensation compounds such as polyamides, polyurethanes, polyesters, polycarbonates or polyureas have gained enormous importance as bulk plastics. They are employed here, inter alia, as synthetic fibres, moulded parts, packing materials or alternatively foams. These compounds are normally obtained by reaction of two divalent monomeric units in each case.
The reaction conditions under which these compounds are prepared are relatively drastic as a rule with respect to the temperature and the pH. However, this is a restriction which concerns the selection of the monomers from which the compounds are synthesized. Monomers which react sensitively to these drastic reaction conditions or monomers which carry substituents which react sensitively to these drastic reaction conditions can be employed with difficulty or not at all.
A further disadvantage of the drastic reaction conditions can be seen in that as a rule the condensations are unselective. Additional functional groups of a monomer unit in this case inevitably lead to undesired side reactions.
One object of the present invention was therefore to make available a process which does not have the disadvantages addressed.
Accordingly, the present invention relates to a process for the preparation of a condensation compound by reaction of at least one functional group of a low-molecular weight compound having at least two functional groups, with at least one functional group of at least one further low-molecular weight compound having at least two functional groups, and which can be identical to the first or different from the first low-molecular weight compound, with obtainment of a condensation compound, which is characterized in that at least one of the functional groups involved in this reaction has been activated before the reaction by reaction with a compound of the following structure (I)
where R′ is a halogen atom or a radical (I′)
and where R
1
, R
2
, R
1
′ and R
2
′ are identical or different and are hydrogen, straight-chain or branched-chain alkyl, aryl, cycloalkyl, heterocyclic or aralkyl radicals having up to 30 C atoms, or either R
1
and R
2
or R
1
′ and R
2
′ or both R
1
and R
2
and R
1
′ and R
2
′ are linked to give a carbocycle or a heterocycle.
In a preferred embodiment of the present invention, a compound of the general structure (I) is employed in which the radical R′ is a halogen atom, particularly preferably a chlorine atom. More preferably, in the compound of the general structure (I) used, the radicals R
1
and R
2
are bridged to give a carbocycle.
Accordingly, the present invention relates to a process, as described above, which is characterized in that the compound of the structure (I) employed is a compound of the following structure (II)
where R
3
to R
10
are identical or different and are hydrogen, straight-chain or branched-chain alkyl, aryl, cycloalkyl, heterocyclic and aralkyl radicals having up to 30 C atoms, or a number of R
3
to R
10
are bridged to give one or more carbocycles or heterocycles.
Obviously, in the content of the present invention, however, it is also possible that R
1
and R
2
are selected such that the bridgehead atom to which the radicals R
7
and R
8
are bonded in the structure (II) is a heteroatom. Depending on the type of heteroatom, it is possible here that one, two or alternatively a number of identical or different radicals R
7
and R
8
are bonded to the bridgehead atom. The bridgehead can obviously also be formed from a number of heteroatoms or a combination of heteroatoms and carbon atoms which, in turn, can optionally be substituted by one or more radicals of the type R
7
and R
8
. In addition, structures are also possible which have an optionally substituted heteroatom instead of a carbon atom to which the radicals R
5
or R
6
are bonded in structure (II).
In a particularly preferred embodiment, the compound of the structure (II) employed is the following compound of the structure (III):
A compound of the general structure (I) which may be mentioned, which has a radical R′ of the general structure (I′), is in particular the symmetrical carbonate of the following structure (IV):
With respect to the low-molecular weight compounds having at least two functional groups, and which are reacted in the process according to the invention, no restrictions in general exist, as long as at least one of the functional groups can be activated with at least one compound of the abovementioned compounds of the structures (I) to (IV).
The term “low-molecular weight compound”, as is used in the context of the present invention, here includes compounds having a molar mass of less than 1000 daltons. Such compounds as a rule comprise up to approximately 20 monomer units.
The term “functional group”, as is used in the context of the present invention, comprises all chemical structural elements which can react with one another or which can be activated with respect to this reaction by reaction with a compound of the structure (I) or (II).
Preferred functional groups of the low-molecular weight compounds having at least two functional groups which may be mentioned are, inter alia, OH groups, optionally substituted amine groups, SH groups, OSO
3
H groups, SO
3
H groups, OPO
3
H
2
groups, OPO
3
HR
11
groups, PO
3
H
2
groups, PO
3
HR
11
groups or COOH groups, the group R
11
being selected such that the functional group can be activated per se with a compound of the structure (I) or (II), or can be reacted with a functional group which is activated with a compound of the structure (I) or (II).
Low-molecular weight compounds having at least two functional groups which are possible are those which have functional groups of identical, preferably of the abovementioned, type. Likewise, low-molecular weight compounds having at least two functional groups and which comprise functional groups of different nature are also possible.
Below, examples of low-molecular weight compounds comprising at least two functional groups are listed in which two functional groups are activated with a compound of the structure (III):
Further examples of low-molecular weight compounds are 1,3,5-benzenetricarboxylic acid, pentaerythritol, 1,3,5-triaminobenzene, melamine or cyclodextrin.
Further examples of low-molecular weight compounds having at least two functional groups are, inter alia, aminoalcohols, hydroxycarboxylic acids or amino acids such as, for example, the compound of the following structure (V)
or the compound reacted with the compound of the structure (III), of the following structure (VI):
or 2-aminoglycerol, gallic acid, 1-amino-3,5-dihydroxy-benzene, aminodicarboxylic acids, diaminocarboxylic acids, hydroxydicarboxylic acids, tri- or tetra-carboxylic acids.
Accordingly, the present invention also relates to a process, as described above, which is characterized in that at least one of the compounds having at least two functional groups has at least two different functional groups.
By means of suitable choice of the reaction conditions in the activation of the at least one functional group of the at least one low-molecular weight compound having at least two functional groups, with a compound of the structure (I) or (II), it is possible in the context of the process according to the invention that all functional groups of a low-molecular weight compound are activated and reacted with non-activated functional groups of at least one further compound having at least two functional groups. This is possible both for low-molecular weight compounds which only have one type of functional group, and for those which comprise two or more different types of func
Dr Gottschall Instruction Gesellschaft fuer Technische Chromatog
Foley & Lardner
Powers Fiona T.
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