Condensation polymer containing hydroxyalkylamide groups

Details Condensation polymer containing hydroxyalkylamide groups Condensation polymer containing hydroxyalkylamide groups

2000-03-24

2002-05-21

Acquah, Samuel A. (Department: 1711)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

From carboxylic acid or derivative thereof

C528S272000, C528S310000, C528S335000, C525S443000, C428S402000

Reexamination Certificate

active

06392006

ABSTRACT:

The invention relates to a linear or branched condensation polymer containing ester groups and at least one amide group in the backbone, having at least one hydroxyalkylamide endgroup and having a weight average molecular mass of ≧800 g/mol.
Preferably, the polymer contains at least two groups according to formula (I)
in which
or (C
6
-C
10
) aryl,
B=(C
2
-C
24
), optionally substituted, aryl or (cyclo)alkyl aliphatic diradical,
R
1
, R
2
, R
3
, R
4
, R
5
and R
6
may, independently of one another, be the same or different, H, (C
6
-C
10
) aryl or (C
1
-C
8
)(cyclo)alkyl radical and
n=1-4.
More preferably the polymer contains at least two groups according to formula (II):
in which
or (C
6
-C
10
) aryl,
B=(C
2
-C
24
), optionally substituted, aryl or (cyclo)alkyl aliphatic diradical, and
R
1
, R
2
, R
3
, R
4
, R
5
and R
6
may, independently of one another, be the same or different, H, (C
6
-C
10
) aryl or (C
1
-C
8
)(cyclo)alkyl radical.
According to a further preferred embodiment, the polymer containing hydroxyalkylamide groups is a polymer according to formula (III):
in which:
or (C
6
-C
10
)aryl
B=(C
2
-C
24
), optionally substituted, aryl or (cyclo)alkyl aliphatic diradical,
X
2
=H or X
1
and
R
1
, R
2
, R
3
, R
4
, R
5
and R
6
may, independently of one another, be the same or different, H, (C
6
-C
10
) aryl or (C
1
-C
8
)(cyclo)alkyl radical or CH
2
—OX
2
.
In formulas (I), (II) and (III) R groups may together or with neighbouring carbon atoms form part of a cycloalkyl group.
According to another preferred embodiment of the invention, the polymer containing &bgr;-hydroxyalkylamide groups is a polymer according to formula (IV):
in which:
(C
6
-C
10
)aryl,
B=(C
2
-C
20
), optionally substituted, aryl or (cyclo)alkyl aliphatic diradical,
X
2
=H or X
1
,
R
3
=H or (C
6
-C
10
) aryl or (C
1
-C
8
)alkyl radical and
R
6
=H or (C
6
-C
10
) aryl or (C
1
-C
8
)alkyl radical.
The weight average molecular mass of the polymer according to the invention is generally between 800 and 50,000, and preferably between 1000 g/mol and 25,000 g/mol.
The number average molecular mass is generally between 600 and 10,000 and preferably between 700 and 4000.
The hydroxyalkylamide functionality is generally between 2 and 250 and preferably between 5 and 50.
Functionality is the average number of reactive groups of the specific type per molecule in the polymer composition.
According to another preferred embodiment of the invention the polymer's hydroxyalkylamide functionality of the polymer is ≧5 and the polymer containing &bgr;-hydroxyalkylamide groups is a polymer represented by formula (V):
in which:
B=(C
2
-C
12
), optionally substituted, aryl or (cyclo)alkyl aliphatic diradical,
X
2
=H or X
1
,
R
3
=H or (C
6
-C
10
) aryl or (C
1
-C
8
)(cyclo)alkyl radical and
R
6
=H or (C
6
-C
10
) aryl or (C
1
-C
8
)(cyclo)alkyl radical
Preferably R
3
and R
6
are (C
1
-C
4
) alkyl.
According to another preferred embodiment of the invention R
3
and R
6
are methyl or ethyl.
B may be saturated or unsaturated.
B may be substituted with for example a (C
1
-C
26
) alkyl group, which may be saturated or unsaturated; preferably C
1
is used.
B may be for example a (methyl-)1,2-ethylene, (methyl-)1,2-ethylidene, 1,3-propylene, (methyl-)1,2-cyclohexyl, (methyl-)1,2-phenylene, 1,3-phenylene, 1,4-phenylene, 2,3-norbornyl, 2,3-norbornen-5-yl and/or (methyl-)1,2 cyclohex-4-enyl radical.
Depending on the starting monomers chosen, the variables B, R
1
, R
2
, R
3
, R
4
, R
5
and R
6
in the molecule or mixture of molecules can be selected to be the same or different per variable.
The polymer composition according to the invention is generally a composition comprising higher and lower oligomers, which usually contains less than 50 wt. %, preferably less than 30 wt. %, of oligomers having a molecular weight smaller than 600.
The polyesteramide according to the invention can for example be obtained through polycondensation of mono- and/or bis-hydroxyalkylamides of bivalent carboxylic acids.
The monohydroxyalkylamide of a bivalent carboxylic acid generally has the formula (VI):
and the bishydroxyalkylamide of a bivalent carboxylic acid generally can be represented by formula (VII):
wherein
R
1
, R
2
, R
3
and R
4
may, independently of one another, be the same or different, H, (C
6
-C
10
) aryl or (C
1
-C
8
)(cyclo)alkyl radical.
Consequently a lineair polymer according to the invention generally comprises the amide and the ester groups alternating along the chain as follows:
E-A-E-A-A-E-A-E-A-E
wherein a diamide is coupled with alternating ester (E)-amide (A) groups.
A branched polymer according to the invention generally comprises the amide and the ester groups alternating along the main and side chains as follows:
wherein a diamide is coupled with alternating ester (E)-amide (A) groups.
In the branched polymers according to the invention (&bgr;)-hydroxyalkylamide groups can be present both as an endgroup
and as a pendant side chain group
Generally, the molar amount of amide bounds in the chain is higher than the amount of ester bounds.
The polymer according to the invention comprises at least 60% by weight of the products represented by the formulas (III)-(V).
Due to side reactions during the preparation of the polymer it is possible that the composition according to the invention comprises also for example secundary amine groups having the formula (VIII):
wherein:
R
1
, R
2
, R
3
and R
4
may, independently of one another, be the same or different, H, (C
6
-C
10
) aryl or (C
1
-C
8
) (cyclo)alkyl radical.
The polymer according to the invention can, also be obtained in a one-step procedure by reacting a cyclic anhydride and an alkanolamine, at a temperature between for example about 20° C. and about 100° C., to form a hydroxyalkylamide, after which, at a temperature between, for example, 120° C. and 250° C., a polyesteramide is obtained through polycondensation with water being removed through distillation.
The reaction can take place without a solvent, but also in water or in an organic solvent.
The removal of water through distillation can take place at a pressure higher than 1 bar, in a vacuum or azeotropically.
Preferably, the cyclic anhydride is an anhydride according to formula (IX):
in which B has the meaning specified above.
Examples of suitable cyclic anhydrides include phthalic anhydride, tetrahydrophthalic anhydride, naphtalenic dicarboxylic anhydride, hexahydrophthalic anhydride, 5-norbornene-2,3-dicarboxylic anhydride, norbornene-2,3-dicarboxylic anhydride, naphtalenic dicarboxylic anhydride, 2-dodecene-1-yl-succinic anhydride, maleic anhydride, (methyl)succinic anhydride, glutaric anhydride, 4-methylphthalic anhydride, 4-methylhexahydrophthalic anhydride, 4-methyltetrahydrophthalic anhydride and the maleinised alkylester of an unsaturated fatty acid.
Preferably the alkanol is an alkanolamine according to formula (X):
in which:
R
1
, R
2
, R
3
, R
4
, R
5
and R
6
may, independently of one another, be the same or different, H, (C
6
-C
10
) aryl or (C
1
-C
8
)(cyclo)alkyl radical or CH
2
OH and n=1-4.
More preferably n=1. The alkanolamine may be a monoalkanolamine, a dialkanolamine, a trialkanolamine or a mixture hereof.
If monoalkanolamines are used in one of the possible polymer syntheses, linear polymers with a functionality of 2 can be obtained. Depending on the application desired, a linear or an entirely or partly branched polymer can be chosen, in which case the degree of branching can be set via the alkanolamines chosen.
If a highly branched structure with a high functionality is desired, di- or trialkanolamines are used as the starting compound.
Examples of suitable mono-&bgr;-alkanolamines include ethanolamine, 1-(m)ethyl ethanolamine, n-butyl ethanolamine, 1-(m)ethyl isopropanolamine, isobutanolamine, &bgr;-cyclohexanolamine, n-butyl isopropanolamine and n-propanolamine.
Examples of suitable di-&bgr;-alkanolamines are 3-amino-1,2-propanediol, 2-amino-

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