Condensation polymer containing dialkylamide endgroups,...

Details Condensation polymer containing dialkylamide endgroups,... Condensation polymer containing dialkylamide endgroups,...

2002-05-21

2003-04-01

Acquah, Samuel A. (Department: 1711)

Stock material or miscellaneous articles

Coated or structually defined flake, particle, cell, strand,...

Rod, strand, filament or fiber

C528S288000, C528S292000, C528S302000, C528S332000, C528S335000, C528S422000, C525S420000, C525S432000

Reexamination Certificate

active

06541110

ABSTRACT:

The invention relates to a condensation polymer having at least one dialkylamide endgroup connected through the polymer backbone to a unit derived from an alkylamide, the connection comprising at least one ester linkage.
According to a preferred embodiment, the polymer according to the invention contains at least two groups according to formula (I)
H, a (C
1
-C
20
) alkylgroup or a (C
6
-C
10
) arylgroup;
B=a (C
6
-C
24
) aryldiradical or a (C
2
-C
24
) alkyldiradical;
R
1
, R
2
, R
3
, R
4
, R
5
and R
6
may, independently of one another, be chosen from the group of H, (C
6
-C
10
) arylgroups or (C
1
-C
8
) alkylgroups
R
7
and R
8
may, independently of one another, be chosen from the group of optionally heteroatom substituted (C
6
-C
10
) arylgroups or optionally heteroatom substituted (C
1
-C
28
) alkylgroups and n=1-4. Preferably, n=1.
According to a further preferred embodiment, the polymer according to the invention is a polymer according to formula (II):
H, a (C
1
-C
20
) alkylgroup or a (C
6
-C
10
) arylgroup;
B=a (C
6
-C
24
) aryldiradical or a (C
2
-C
24
) alkyldiradical;
R
1
, R
2
, R
3
, R
4
, R
5
and R
6
may, independently of one another, be chosen from the group of H, (C
6
-C
10
) arylgroups, (C
1
-C
8
) alkylgroups or —CH
2
—OX
2
;
R
7
and R
8
may, independently of one another, be chosen from the group of optionally heteroatom substituted (C
6
-C
10
) arylgroups or optionally heteroatom substituted (C
1
-C
28
) alkylgroups.
Preferably, R
1
and R
2
are both equal to H.
According to a further preferred embodiment, the polymer according to the invention has a number of dialkylamide endgroups ≧3 and the polymer is represented by formula (III):
B=a (C
6
-C
24
) aryldiradical or a (C
2
-C
24
) alkyldiradical;
R
3
and R
6
are chosen from the group of H, (C
6
-C
10
) arylgroups and (C
1
-C
8
)alkylgroups;
R
7
and R
8
may, independently of one another, be chosen from the group of optionally heteroatom substituted (C
6
-C
10
) arylgroups or optionally heteroatom substituted (C
1
-C
28
) alkylgroups.
In all above embodiments, preferably, R
3
and R
6
are (C
1
-C
4
) alkyl groups, more preferably a methyl- or ethylgroup. In all above embodiments, preferably, R
7
and R
8
are optionally hetero-atom substituted (C
1
-C
20
) alkyl groups, more preferably, R
7
and R
8
are hetero-atom substituted C
2-
, C
3-
or C
6-
alkylgroups. R
7
and R
8
may be substituted with a group selected from the group of alcohol, ether, ester, cyanide, carbonate, urethane, urea, amide, imide, amine, imine, imidazole, oxime, sulfide, thiol, thiourea, sulfon, sulfoxide, sulfate, fosfate, fosfine, fosfinoxide, silane, silicone, silicate, fluoro, chloro, bromo or iodo groups. Suitable choices for R
7
and R
8
are di(m)ethylaminoethyl, di(m)ethylaminopropyl, di(m)ethylaminohexyl, tri(m)ethylsilylpropyl, tri(m)ethoxysilylpropyl, perfluoro-octyl, perfluoro-octyl-(m)ethyl, (m)ethoxy-ethyl, (m)ethoxy-2-propyl, maleimido-propyl, maleimido-hexyl, octenylsuccinimido-hexyl, hexahydrophthalimido-hexyl, 2-(benz)imidazole-ethyl, difenylfosfino-ethyl, furfuryl, cyanoethyl, or cyanopropyl groups. R
7
and R
8
can also be part of the same optionally substituted cyclic group, such as a morfoline, thiomorfoline, piperidine, pyrrolidine, oxazolidine, thiazolidine or piperazine group.
In all formulas in this application in which R-groups are present, the R groups may together or with neighbouring carbon atoms form part of a cycloalkyl group.
Depending on the starting monomers chosen, B, R
1
, R
2
, R
3
, R
4
, R
5
, R
6
, R
7
and R
8
in the molecule or mixture of molecules can be selected to be the same or different.
B is optionally substituted, preferably with a (C
1
-C
26
) alkyl group. Preferably, the alkylgroup is chosen from the group of methyl, octenyl, nonenyl, decenyl, undecenyl or dodecenyl. Suitable choices for B are (alkyl-)1,2-ethylene, where the alkyl is defined as above, (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 or (methyl-)1,2 cyclohex-4-enyl radical.
Preferably, the weight average molecular mass of the polymer according to the invention is between 600 g/mol and 50,000 g/mol, more preferably between 800 g/mol and 25,000 g/mol.
Preferably, the number average molecular mass is between 500 g/mol and 15,000 g/mol, more preferably between 700 g/mol and 4,000 g/mol.
Preferably, the average number of dialkylamide endgroups per molecule is between 2 and 250, more preferably between 3 and 50.
The polymer according to the invention can be linear or branched. The linear polymer according to the invention generally comprises amide and ester units alternating along a chain as follows:
—A-E—A—E—A—A—E—A—E—A—E—A—
wherein a diamide (A—A) unit is coupled with alternating ester (E) and amide (A) units.
A branched polymer according to the invention generally comprises amide and the ester units alternating along the main and side chains as follows:
wherein a diamide (A—A) is coupled with alternating ester (E) and amide (A) units.
Preferably, in the branched polymer according to the invention a (&bgr;)-hydroxyalkylamide group is present, which can be both present as a bis-(&bgr;)-hydroxyalkylamide endgroup, such as
or as a pendant side chain group, such as
Preferably, the molar amount of amide units in the chain is higher than the molar amount of ester units.
The invention also relates to a process for the production of the polymer according to the invention.
According to a preferred embodiment, the polymer according to the invention can be obtained through polycondensation of a mono- and/or bis-hydroxyalkylamide of a dicarboxylic acid in the presence of a mono-dialkylamide of a dicarboxylic acid.
Preferably, the mono-hydroxyalkylamide of the dicarboxylic acid is a compound according to formula (IV):
Preferably, the mono-dialkylamide of the dicarboxylic acid is a compound according to formula (V):
Preferably, the bis-hydroxyalkylamide of the dicarboxylic acid is a compound according to formula (VI):
wherein (in formula's IV, V and VI)
R
1
, R
2
, R
3
and R
4
may, independently of one another, be chosen from the group of H, (C
6
-C
10
) arylgroups or (C
1
-C
8
) alkylgroups;
R
7
and R
8
may, independently of one another, be chosen from the group of optionally heteroatom substituted (C
6
-C
10
) arylgroups or optionally heteroatom substituted (C
1
-C
28
) alkylgroups and
B may be a (C
6
-C
24
) aryldiradical or a (C
2
-C
24
) alkyldiradical.
According to a further preferred embodiment, the polymer according to the invention can be obtained in a one-step procedure by reacting a cyclic anhydride, a dialkylamine and an alkanolamine, at room temperature or at an elevated temperature, preferably between about 20° C. and about 120° C., to form hydroxyalkylamide and dialkylamides, after which, at an elevated temperature, preferably between 120° C. and 250° C., a i is obtained through polycondensation with water being removed, preferably through distillation.
The one-step procedure can take place with or without a solvent. Suitable solvents are water or an organic solvents, such as methyl-isobutylketon, butylacetate, toluene or xylene.
The removal of water through distillation can take place at either reduced or elevated pressure, such as at a pressure higher than 1.10
5
Pa, in a vacuum (<1.10
5
Pa) or azeotropically.
Preferably, the cyclic anhydride is an anhydride according to formula (VII):
in which B has the meaning as 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-octene-1-yl-succinic anhydride, 2-nonene-1-yl-succinic anhydride, 2-decene-1-yl-succinic anhydride, 2-undecene-1-yl-succinic anhydride 2-dodecene-1-yl-succinic anhydride, maleic anhydride, (methyl)succinic anhydride, glutaric anhydri

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