Condensation polymer containing esteralkylamide-acid groups

Details Condensation polymer containing esteralkylamide-acid groups Condensation polymer containing esteralkylamide-acid groups

2001-09-24

2003-11-11

Woodward, Ana (Department: 1711)

Stock material or miscellaneous articles

Composite

Of polyamidoester

C428S474400, C525S419000, C525S437000, C528S288000, C528S291000, C528S335000

Reexamination Certificate

active

06645636

ABSTRACT:

The invention relates to a condensation polymer having at least one carboxylic acid endgroup connected to an alkylamide group via an ester linkage.
Preferably, the polymer contains at least two groups according to formula (I):
in which
H, (C
1
-C
20
)(cyclo)alkyl,
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
H, (C
1
-C
20
)(cyclo)alkyl,
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 another preferred embodiment, the polymer containing hydroxyalkylamide groups is a polymer according to formula (III):
in which:
H, (C
1
-C
20
)(cyclo)alkyl or
(C
6
-C
10
)aryl
A=OH,
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 or CH
2
—OX
2
.
In formulas (I), (II) and (IlI) 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;-esteralkylamide-acid groups is a polymer according to formula (IV):
in which:
H, (C
1
-C
20
)(cyclo)alkyl or
(C
6
-C
10
)aryl,
B=(C
2
-C
24
), optionally substituted, aryl or (cyclo)alkyl aliphatic diradical,
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 generally ranges between 500 and 50,000, and is preferably between 600 g/mol and 10,000 g/mol.
The number average molecular mass may range between 400 and 10,000 and is preferably between 500 and 2000.
The esteralkylamide-acid functionality may range between 2 and 250 and is preferably between 3 and 50.
The 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 carboxyl group functionality of the polymer is ≧3 and the polymer containing esteramide acid groups is a polymer represented by formula (V):
in which:
B=(C
2
-C
12
), optionally substituted, aryl or (cyclo)alkyl aliphatic diradical,
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; or with a carboxylic acid.
B may be for example a (methyl)-1,2-ethylene, octenyl- or dodecenyl-1,2-ethylene, (methyl-)1,2-ethylidene, 1,3-propylene, (methyl-)1,2-cyclohexyl, 4-carboxyl-1,2-phenylene, (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 may be 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 400.
The polymer according to the invention may, for example, be obtained through polycondensation of an hydroxyalkylamide-acid and an esteralkylamide diacid derived from an alkanolamine.
The hydroxyalkylamide-acid of an alkanolamine may have the formula (VI):
and the esteralkylamidediacid of an alkanolamine 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 and
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-E-E-A-E-A-E
wherein one or more diesters are coupled with alternating ester (E)—amide (A) groups or
E-A-E-A-E-A-E-A-E
wherein ester and amide groups are perfectly alternating throughout the polymer.
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 one or more diestersare coupled with alternating ester (E)—amide (A) groups or
wherein ester and amide groups are perfectly alternating through the polymer.
Generally, the molar amount of amide bonds in the chain is lower than the amount of ester bonds.
The polymer according to the invention comprises at least 60% by weight of the products represented by the formulas (III)-(V).
According to a preferred embodiment of the invention the polymer is obtained in a one-step procedure by reacting an alkanolamine and a molar excess of cyclic anhydride, 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. Optionally water may be removed through distillation.
The removal of water through distillation may take place at a pressure higher than 1 bar, in a vacuum or azeotropically.
The reaction may take place without a solvent, but it is also possible that the reaction takes place in water or in an organic solvent.
Preferably, the cyclic anhydride is an anhydride according to formula (VIII):
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, trimellitic anhydride, (methyl, octyl or dodecenyl)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 (IX):
in which:
or (C
1
-C
20
)(cyclo)alkyl,
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 selected, 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 can be used, also carboxylic acid substituted anhydrides in combination with monoalkanolamines can be used as a 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-1,3-propanediol diisobutanolamine (bis-2-hy

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