US 5,880,220 A · Biodegradable polymers, process for the preparation thereof and the use thereof for producing biodegradable moldings

A biodegradable polyetheresteramide P1 obtained by reacting a mixture consisting essentially of

(a1) a mixture consisting essentially of 20-95 mol % of adipic acid or ester-forming derivatives thereof or mixtures thereof,
5-80 mol % of terephthalic acid or ester-forming derivatives thereof or mixtures thereof, and
0-5 mol % of a compound containing sulfonate groups,
where the total of the individual mole percentages is 100 mol %, and
(a2) a mixture of dihydroxy compounds consisting essentially of
(a21) from 15 to 99.3 mol % of a dihydroxy compound selected from the group consisting of C.sub.2 -C.sub.6 -alkanediols and C.sub.5 -C.sub.10 -cycloalkanediols,
(a22) from 0.2 to 85 mol % of a dihydroxy compound containing ether functionalities of the formula I
HO-(CH.sub.2).sub.n --O!.sub.m --H I
where n is 2, 3 or 4 and m is an integer from 2 to 250, or mixtures thereof,
(a23) from 0.5 to 80 mol % of an amino-C.sub.2 -C.sub.12 -alkanol or amino-C.sub.5 -C.sub.10 -cycloalkanol, and
(a24) from 0 to 50 mol % of a diamino-C.sub.1 -C.sub.8 -alkane,
(a25) from 0 to 50 mol % of a 2,2'-bisoxazoline of the formula II ##STR6## where R.sup.1 is a single bond, a (CH.sub.2).sub.q alkylene group with q=2, 3 or 4, or a phenylene group, where the total of the individual mole percentages is 100 mol %,
where the molar ratio of (a1) to (a2) is selected in the range from 0.4:1 to 1.5:1,
with the proviso that the polyetheresteramide P1 has a molecular weight (M.sub.n) in the range from 5000 to 80,000 g/mol, a viscosity number in the range from 30 to 450 g/ml (measured in o-dichlorobenzene/phenol (50/50 ratio by weight) at a concentration of 0.5% by weight of polyetheresteramide P1 at 25.degree. C.) and a melting point in the range from 50.degree. to 200.degree. C., and with the further proviso that from 0 to 5 mol %, based on the molar amount of component (a1) used, of a compound D with at least three groups capable of ester formation is used to prepare the polyetheresteramides P1.

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A biodegradable polyetheresteramide P2 obtained by reacting a mixture consisting essentially of

(b1 ) a mixture consisting essentially of
20-95 mol % of adipic acid or ester-forming derivatives thereof or mixtures thereof,
5-80 mol % of terephthalic acid or ester-forming derivatives thereof or mixtures thereof, and
0-5 mol % of a compound containing sulfonate groups,
where the total of the individual mole percentages is 100 mol %,
(b2) mixture (a2), of dihydroxy compounds, consisting esentially of
(a21) from 15 to 99.3 mol % of a dihydroxy compound selected from the group consisting of C.sub.2 -C.sub.6 -alkanediols and C.sub.5 -C.sub.10 -cycloalkanediols,
(a22) from 0.2 to 85 mol % of a dihydroxy compound containing ether functionalities of the formula I
HO--(CH.sub.2).sub.n --O!.sub.m --H I
where n is 2, 3 or 4 and m is an integer from 2 to 250, or mixtures thereof,
(a23) from 0.5 to 80 mol % of an amino-C.sub.2 -C.sub.12 -alkanol or amino-C.sub.5 -C.sub.10 -cycloalkanol, and
(a24) from 0 to 50 mol % of a diamino-C.sub.1 -C.sub.8 -alkane,
(a25) from 0 to 50 mol % of a 2,2'-bisoxazoline of the formula II ##STR14## where R.sup.1 is a single bond, a (CH.sub.2).sub.q alkylene group with q=2, 3 or 4, or a phenylene group, where the total of the individual mole percentages is 100 mol %,
where the molar ratio of (b1) to (b2) is selected in the range from 0.4:1 to 1.25:1,
(b3) from 0.01 to 40% by weight, based on component (b1), of an amino carboxylic acid B1, and
(b4) from 0 to 5 mol %, based on component (b1), of compound D with at least three groups capable of ester formation,
where the amino carboxylic acid B1 is selected from the group consisting of the natural amino acids, polyamides with a molecular weight not exceeding 18,000 g/mol, obtained by polycondensation of a dicarboxylic acid with 4 to 6 carbon atoms and a diamine with 4 to 10 carbon atoms and compounds which are defined by the formulae IIIa and IIIb ##STR15## where p is an integer from 1 to 1500 and r is an integer from 1 to 4, and G is a radical which is selected from the group consisting of phenylene, --(CH.sub.2).sub.n --, where n is an integer from 1 to 12, --C(R.sup.2)H-- and --C(R.sup.2)HCH.sub.2, where R.sup.2 is methyl or ethyl,
and polyoxazolines with the repeating unit IV ##STR16## where R.sup.3 is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.5 -C.sub.8 -cycloalkyl, phenyl which is unsubstituted or substituted up to three times by C.sub.1 -C.sub.4 -alkyl groups, or tetrahydrofuryl,
where the polyesteramide P2 has a molecular weight (M.sub.n) in the range from 5000 to 80,000 g/mol, a viscosity number in the range from 30 to 450 g/ml (measured in o-dichlorobenzene/phenol (50/50 ratio by weight) at a concentration of 0.5% by weight of polyetheresteramide P2 at 25.degree. C.) and a melting point in the range from 50.degree. to 255.degree. C.

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A biodegradable polymer T3 with a molecular weight (M.sub.n) in the range from 8000 to 80,000 g/mol, with a viscosity number in the range from 30 to 450 g/ml (measured in o-dichlorobenzene/phenol (50/50 ratio by weight) at a concentration of 0.5% by weight of polymer T3 at 25.degree. C.) and a melting point in the range from 50.degree. to 255.degree. C., obtained by reacting

(g1) polyetheresteramide P2 obtained by reacting a mixture consisting essentially of
(b1) a mixture consisting essentially of
20-95 mol % of adipic acid or ester-forming derivatives thereof or mixtures thereof,
- 80mol % of terephthalic acid or ester-forming derivatives thereof or mixtures thereof, and
0-5 mol % of a compound containing sulfonate groups,
where the total of the individual mole percentages is 100 mol %,
(b2) mixture (a2), of dihydroxy compounds, consisting esentially of
(a21) from 15 to 99.3 mol % of a dihydroxy compound selected from the group consisting of C.sub.2 -C.sub.6 -alkanediols and C.sub.5 -C.sub.10 -cycloalkanediols,
(a22) from 0.2 to 85 mol % of a dihydroxy compound containing ether functionalities of the formula I
HO--(CH.sub.2).sub.n --O!.sub.m --H I
where n is 2, 3 or 4 and m is an integer from 2 to 250, or mixtures thereof,
(a23) from 0.5 to 80 mol % of an amino-C.sub.2 -C.sub.12 -alkanol or amino-C.sub.5 -C.sub.10 -cycloalkanol, and
(a24) from 0 to 50 mol % of a diamino-C.sub.1 -C.sub.8 -alkane,
(a25) from 0 to 50 mol % of a 2,2'-bisoxazoline of the formula II ##STR17## where R1 is a single bond, a (CH.sub.2).sub.q alkylene group with q=2, 3 or 4, or a phenylene group, where the total of the individual mole percentages is 100 mol %,
where the molar ratio of (b1) to (b2) is selected in the range from 0.4:1 to 1.25:1,
(b3) from 0.01 to 40% by weight, based on component (b1), of an amino carboxylic acid B1, and
(b4) from 0 to 5 mol %, based on component (b1), of compound D with at least three groups capable of ester formation,
where the amino carboxylic acid B1 is selected from the group consisting of the natural amino acids, polyamides with a molecular weight not exceeding 18,000 g/mol, obtained by polycondensation of a dicarboxylic acid with 4 to 6 carbon atoms and a diamine with 4 to 10 carbon atoms and compounds which are defined by the formulae IIIa and IIIb ##STR18## where p is an integer from 1 to 1500 and r is an integer from 1 to 4, and G is a radical which is selected from the group consisting of phenylene, --(CH.sub.2).sub.n --, where n is an integer from 1 to 12, --C(R.sup.2)H-- and --C(R.sup.2)HCH.sub.2, where R.sup.2 is methyl or ethyl,
and polyoxazolines with the repeating unit IV ##STR19## where R.sup.3 is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.5 -C.sub.8 -cycloalkyl, phenyl which is unsubstituted or substituted up to three times by C.sub.1 -C.sub.4 -alkyl groups, or tetrahydrofuryl,
where the polyesteramide P2 has a molecular weight (M.sub.n) in the range from 5000 to 80,000 g/mol, a viscosity number in the range from 30 to 450 g/ml (measured in o-dichlorobenzene/phenol (50/50 ratio by weight) at a concentration of 0.5% by weight of polyetheresteramide P2 at 25.degree. C.) and a melting point in the range from 50.degree. to 255.degree. C. or
(g2) a mixture consisting essentially of polyetheresteramide P1 as claimed in claim 1 and 0.01-50% by weight, based on polyetheresteramide P1, of amino carboxylic acid B1,
(g3) a mixture consisting essentially of polyetheresteramides P1 which differ from one another in composition,
with 0.1-5% by weight, based on the amount of the polyetheresteramides used, of diisocyanate C1 and with 0-5 mol %, based on the particular molar amounts of component (a1) used to prepare-the polyetheresteramides (g1) to (g3) used, of compound D.

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A process for preparing the biodegradable polyetheresteramides P2 having a molecular weight (M.sub.n) in the range from 5000 to 80,000 g/mol, a viscosity number in the range from 30 to 450 g/ml (measured in o-dichlorobenzene/phenol (50/50 ratio by weight) at a concentration of 0.5% by weight of polyetheresteramide P2 at 25.degree. C.) and a melting point in the range from 50.degree. to 255.degree. C., which comprises reacting a mixture consisting essentially of

(b1) a mixture consisting essentially of
20-95 mol % of adipic acid or ester-forming derivatives thereof or mixtures thereof,
5-80 mol % of terephthalic acid or ester-forming derivatives thereof or mixtures thereof, and
0-5 mol % of a compound containing sulfonate groups, where the total of the individual mole percentages is 100 mol %,
(b2) mixture (a2), of dihydroxy compounds, consisting essentially of
(a21) from 15 to 99.3 mol % of a dihydroxy compound selected from the group consisting of C.sub.2 -C.sub.6 -alkanediols and C.sub.5 -C.sub.10 -cycloalkanediols,
(a22) from 0.2 to 85 mol % of a dihydroxy compound containing ether functionalities of the formula I
HO-(CH.sub.2).sub.n --O!.sub.m --H I
where n is 2, 3 or 4 and m is an integer from 2 to 250, or mixtures thereof,
(a23) from 0.5 to 80 mol % of an amino-C.sub.2 -C.sub.12 -alkanol or amino-C.sub.5 -C.sub.10 -cycloalkanol, and
(a24) from 0 to 50 mol % of a diamino-C.sub.1 -C.sub.8 -alkane,
(a25) from 0 to 50 mol % of a 2,2'-bisoxazoline of the formula II ##STR21## where R.sup.1 is a single bond, a (CH.sub.2).sub.q alkylene group with q=2, 3 or 4, or a phenylene group, where the total of the individual mole percentages is 100 mol %,
where the molar ratio of (b1) to (b2) is selected in the range from 0.4:1 to 1.5:1,
(b3) from 0.01 to 40% by weight, based on component (b1), of an amino carboxylic acid B1,
where the amino carboxylic acid B1 is selected from the group consisting of the natural amino acids, polyamides with a molecular weight not exceeding 18,000 g/mol, obtained by polycondensation of a dicarboxylic acid with 4 to 6 carbon atoms and a diamine with 4 to 10 carbon atoms and compounds which are defined by the formulae IIIa and IIIb ##STR22## where p is an integer from 1 to 1500 and r is an integer from 1 to 4, and G is a radical which is selected from the group consisting of phenylene, --(CH.sub.2).sub.n --, where n is an integer from 1 to 12, --C(R.sup.2)H-- and --C(R.sup.2)HCH.sub.2, where R.sup.2 is methyl or ethyl,
and polyoxazolines with the repeating unit IV ##STR23## where R.sup.3 is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.5 -C.sub.8 -cycloalkyl, phenyl which is unsubstituted or substituted up to three times by C.sub.1 -C.sub.4 -alkyl groups, or tetrahydrofuryl, and
(b4) from 0 to 5 mol %, based on component (b1), of compound D with at least three groups capable of ester formation.

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A process for preparing the biodegradable polyetheresteramides Q1 with a molecular weight (M.sub.n) in the range from 5000 to 80,000 g/mol, a viscosity number in the range from 30 to 450 g/ml (measured in o-dichlorobenzene/phenol (50/50 ratio by weight) at a concentration of 0.5% by weight of polyetheresteramide Q1 at 25.degree. C.) and a melting point in the range from 50.degree. to 255.degree. C., which comprises in a first step preparing

(c1) polyetheresteramide P1 obtained by reacting a mixture consisting essentially of
(a1) a mixture consisting essentially of 20-95 mol % of adipic acid or ester-forming derivatives thereof or mixtures thereof,
- 80mol % of terephthalic acid or ester-forming derivatives thereof or mixtures thereof, and
0-5 mol % of a compound containing sulfonate groups,
where the total of the individual mole percentages is 100 mol %, and
(a2) a mixture of dihydroxy compounds consisting essentially of
(a21) from 15 to 99.3 mol % of a dihydroxy compound selected from the group consisting of C.sub.2 -C.sub.6 -alkanediols and C.sub.5 -C.sub.10 -cycloalkanediols,
(a22) from 0.2 to 85 mol % of a dihydroxy compound containing ether functionalities of the formula I
HO-(CH.sub.2).sub.n --O!.sub.m --H I
where n is 2, 3 or 4 and m is an integer from 2 to 250, or mixtures thereof,
(a23) from 0.5 to 80 mol % of an amino-C.sub.2 -C.sub.12 -alkanol or amino-C.sub.5 -C.sub.10 -cycloalkanol, and
(a24) from 0 to 50 mol % of a diamino-C.sub.1 -C8-alkane,
(a25) from 0 to 50 mol % of a 2,2'-bisoxazoline of the formula II ##STR24## where R.sup.1 is a single bond, a (CH.sub.2).sub.q alkylene group with q=2, 3 or 4, or a phenylene group, where the total of the individual mole percentages is 100 mol %,
where the molar ratio of (a1) to (a2) is selected in the range from 0.4:1 to 1.5:1,
with the proviso that the polyetheresteramide P1 has a molecular weight (M.sub.n) in the range from 5000 to 80,000 g/mol, a viscosity number in the range from 30 to 450 g/ml (measured in o-dichlorobenzene/phenol (50/50 ratio by weight) at a concentration of 0.5% by weight of polyetheresteramide P1 at 25.degree. C.) and a melting point in the range from 50.degree. to 200.degree. C., and with the further proviso that from 0 to 5 mol %, based on the molar amount of component (a1) used, of a compound D with at least three groups capable of ester formation is used to prepare the polyetheresteramides P1,
and in a second step reacting P1 with
(c2) 0.01-50% by weight, based on (c1), of amino carboxylic acid B1,
where the amino carboxylic acid B1 is selected from the group consisting of the natural amino acids, polyamides with a molecular weight not exceeding 18,000 g/mol, obtained by polycondensation of a dicarboxylic acid with 4 to 6 carbon atoms and a diamine with 4 to 10 carbon atoms and compounds which are defined by the formulae IIIa and IIIb ##STR25## where p is an integer from 1 to 1500 and r is an integer from 1 to 4, and G is a radical which is selected from the group consisting of phenylene, --(CH.sub.2).sub.n --, where n is an integer from 1 to 12, --C(R.sup.2)H-- and --C(R.sup.2)HCH.sub.2, where R.sup.2 is methyl or ethyl,
and polyoxazolines with the repeating unit IV ##STR26## where R.sup.3 is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.5 -C.sub.8 -cycloalkyl, phenyl which is unsubstituted or substituted up to three times by C.sub.1 -C.sub.4 -alkyl groups, or tetrahydrofuryl, and
(c3) 0-5 mol %, based on the molar amount of component (a1) used for the preparation of P1, of compound D.

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A process for preparing the biodegradable polyetheresteramides Q2 with a molecular weight (M.sub.n) in the range from 6000 to 80,000 g/mol, a viscosity number in the range from 30 to 450 g/ml (measured in o-dichlorobenzene/phenol (50/50 ratio by weight) at a concentration of 0.5% by weight of polyetheresteramide Q2 at 25.degree. C.) and a melting point in the range from 50.degree. to 200.degree. C., which comprises in a first step preparing

(d1) polyetheresteramide P1 obtained by reacting a mixture consisting essentially of (a1) a mixture consisting essentially of 20-95 mol % of adipic acid or ester-forming derivatives thereof or mixtures thereof,
5-80 mol % of terephthalic acid or ester-forming derivatives thereof or mixtures thereof, and
0-5 mol % of a compound containing sulfonate groups,
where the total of the individual mole percentages is 100 mol %, and
(a2) a mixture of dihydroxy compounds consisting essentially of
(a21) from 15 to 99.3 mol % of a dihydroxy compound selected from the group consisting of C.sub.2 -C.sub.6 -alkanediols and C.sub.5 -C.sub.10 -cycloalkanediols,
(a22) from 0.2 to 85 mol % of a dihydroxy compound containing ether functionalities of the formula I
HO--(CH.sub.2).sub.n --O!.sub.m --H I
where n is 2, 3 or 4 and m is an integer from 2 to 250, or mixtures thereof,
(a23) from 0.5 to 80 mol % of an amino-C.sub.2 -C.sub.12 -alkanol or amino-C.sub.5 -C.sub.10 -cycloalkanol, and
(a24) from 0 to 50 mol % of a diamino-C.sub.1 -C.sub.8 -alkane,
(a25) from 0 to 50 mol % of a 2,2'-bisoxazoline of the formula II ##STR27## where R.sup.1 is a single bond, a (CH.sub.2).sub.q alkylene group with q=2, 3 or 4, or a phenylene group, where the total of the individual mole percentages is 100 mol %,
where the molar ratio of (a1) to (a2) is selected in the range from 0.4:1 to 1.5:1,
with the proviso that the polyetheresteramide P1 has a molecular weight (M.sub.n) in the range from 5000 to 80,000 g/mol, a viscosity number in the range from 30 to 450 g/ml (measured in o-dichlorobenzene/phenol (50/50 ratio by weight) at a concentration of 0.5% by weight of polyetheresteramide P1 at 25.degree. C.) and a melting point in the range from 50.degree. to 200.degree. C., and with the further proviso that from 0 to 5 mol %, based on the molar amount of component (a1) used, of a compound D with at least three groups capable of ester formation is used to prepare the polyetheresteramides P1,
and in a second step reacting a mixture consisting essentially of from 95 to 99.9% by weight of (d1),
(d2) from 0.1 to 5% by weight of a diisocyanate C1 and
(d3) from 0 to 5 mol %, based on the molar amount of component (a1) used for the preparation of P1, of compound D.

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A process for preparing the biodegradable polymers T1 with a molecular weight (M.sub.n) in the range from 8000 to 80,000 g/mol, with a viscosity number in the range from 30 to 450 g/ml (measured in o-dichlorobenzene/phenol (50/50 ratio by weight) at a concentration of 0.5% by weight of polymer T1 at 25.degree. C.) and a melting point in the range from 50.degree. to 255.degree. C., which comprises in a first step reacting polyetheresteramide Q1 with a molecular weight (M.sub.n) in the range from 5000 to 80,000 g/mol, a viscosity number in the range from 30 to 450 g/ml (measured in o-dichlorobenzene/phenol (50/50 ratio by weight) at a concentration of 0.5% by weight of polyetheresteramide Q1 at 25.degree. C.) and a melting point in the range from 50.degree. to 255.degree. C., obtained by reacting a mixture consisting essentially of

(c1) polyetheresteramide P1 obtainable by reacting a mixture consisting essentially of
(a1) a mixture consisting essentially of 20-95 mol % of adipic acid or ester-forming derivatives thereof or mixtures thereof,
5-80 mol % of terephthalic acid or ester-forming derivatives thereof or mixtures thereof, and
0-5 mol % of a compound containing sulfonate groups,
where the total of the individual mole percentages is 100 mol %, and
(a2) a mixture of dihydroxy compounds consisting essentially of
(a21) from 15 to 99.3 mol % of a dihydroxy compound selected from the group consisting of C.sub.2 -C.sub.6 -alkanediols and C.sub.5 -C.sub.10 -cycloalkanediols,
(a22) from 0.2 to 85 mol % of a dihydroxy compound containing ether functionalities of the formula I
HO--(CH.sub.2).sub.n --O!.sub.m --H I
where n is 2, 3 or 4 and m is an integer from 2 to 250, or mixtures thereof,
(a23) from 0.5 to 80 mol % of an amino-C.sub.2 -C.sub.12 -alkanol or amino-C.sub.5 -C.sub.10 -cycloalkanol, and
(a24) from 0 to 50 mol % of a diamino-C.sub.1 -C.sub.8 -alkane,
(a25) from 0 to 50 mol % of a 2,2'-bisoxazoline of the formula II ##STR28## where R.sup.1 is a single bond, a (CH.sub.2).sub.q alkylene group with q=2, 3 or 4, or a phenylene group, where the total of the individual mole percentages is 100 mol %,
where the molar ratio of (a1) to (a2) is selected in the range from 0.4:1 to 1.5:1,
with the proviso that the polyetheresteramide P1 has a molecular weight (M.sub.n) in the range from 5000 to 80,000 g/mol, a viscosity number in the range from 30 to 450 g/ml (measured in o-dichlorobenzene/phenol (50/50 ratio by weight) at a concentration of 0.5% by weight of polyetheresteramide P1 at 25.degree. C.) and a melting point in the range from 50.degree. to 200.degree. C., and with the further proviso that from 0 to 5 mol %, based on the molar amount of component (a1) used, of a compound D with at least three groups capable of ester formation is used to prepare the polyetheresteramides P1,
(c2) 0.01-50% by weight, based on (c1), of amino carboxylic acid B1,
where the amino carboxylic acid B1 is selected from the group consisting of the natural amino acids, polyamides with a molecular weight not exceeding 18,000 g/mol, obtained by polycondensation of a dicarboxylic acid with 4 to 6 carbon atoms and a diamine with 4 to 10 carbon atoms and compounds which are defined by the formulae IIIa and IIIb ##STR29## where p is an integer from 1 to 1500 and r is an integer from 1 to 4, and G is a radical which is selected from the group consisting of phenylene, --(CH.sub.2).sub.n --, where n is an integer from 1 to 12, --C(R.sup.2)H-- and --C(R.sup.2)HCH.sub.2, where R.sup.2 is methyl or ethyl, and polyoxazolines with the repeating unit IV ##STR30## where R.sup.3 is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.5 -C.sub.8 -cycloalkyl, phenyl which is unsubstituted or substituted up to three times by C.sub.1 -C.sub.4 -alkyl groups, or tetrahydrofuryl, and
(c3) 0-5 mol %, based on the molar amount of component (a1) used for the preparation of P1, of compound D
and in a second step reacting Q1 with (e1) 0.1-5% by weight, based on the polyetheresteramide Q1, of diisocyanate C1 and with (e2) 0-5 mol %, based on the molar amount of component (a1) used for the preparation of Q1, of compound D.

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A process for preparing the biodegradable polymers T2 with a molecular weight (M.sub.n) in the range from 8000 to 80,000 g/mol, with a viscosity number in the range from 30 to 450 g/ml (measured in o-dichlorobenzene/phenol (50/50 ratio by weight) at a concentration of 0.5% by weight of polymer T2 at 25.degree. C.) and a melting point in the range from 50.degree. to 255.degree. C., which comprises in a first step reacting polyetheresteramide Q2 with a molecular weight (M.sub.n) in the range from 6000 to 80,000 g/mol, a viscosity number in the range from 30 to 450 g/ml (measured in o-dichlorobenzene/phenol (50/50 ratio by weight) at a concentration of 0.5% by weight of polyetheresteramide Q2 at 25.degree. C.) and a melting point in the range from 50.degree. to 200.degree. C., obtained by reacting a mixture consisting essentially of

(d1) from 95 to 99.9% by weight of polyetheresteramide P1 by reacting a mixture consisting essentially of
(a1) a mixture consisting essentially of 20-95 mol % of adipic acid or ester-forming derivatives thereof or mixtures thereof,
5-80 mol % of terephthalic acid or ester-forming derivatives thereof or mixtures thereof, and
- 5mol % of a compound containing sulfonate groups,
where the total of the individual mole percentages is 100 mol %, and
(a2) a mixture of dihydroxy compounds consisting essentially of
(a21) from 15 to 99.3 mol % of a dihydroxy compound selected from the group consisting of C.sub.2 -C.sub.6 -alkanediols and C.sub.5 -C.sub.10 -cycloalkanediols,
(a22) from 0.2 to 85 mol % of a dihydroxy compound containing ether functionalities of the formula I
HO--(CH.sub.2).sub.n --O!.sub.m --H I
where n is 2, 3 or 4 and m is an integer from 2 to 250, or mixtures thereof,
(a23) from 0.5 to 80 mol % of an amino-C.sub.2 -C.sub.12 -alkanol or amino-C.sub.5 -C.sub.10 -cycloalkanol, and
(a24) from 0 to 50 mol % of a diamino-C.sub.1 -C.sub.8 -alkane,
(a25) from 0 to 50 mol % of a 2,2'-bisoxazoline of the formula II ##STR31## where R.sup.1 is a single bond, a (CH.sub.2).sub.q alkylene group with q=2, 3 or 4, or a phenylene group, where the total of the individual mole percentages is 100 mol %,
where the molar ratio of (a1) to (a2) is selected in the range from 0.4:1 to 1.5:1,
with the proviso that the polyetheresteramide P1 has a molecular weight (M.sub.n) in the range from 5000 to 80,000 g/mol, a viscosity number in the range from 30 to 450 g/ml (measured in o-dichlorobenzene/phenol (50/50 ratio by weight) at a concentration of 0.5% by weight of polyetheresteramide P1 at 25.degree. C.) and a melting point in the range from 50.degree. to 200.degree. C., and with the further proviso that from 0 to 5 mol %, based on the molar amount of component (a1) used, of a compound D with at least three groups capable of ester formation is used to prepare the polyetheresteramides P1,
(d2) from 0.1 to 5% by weight of a diisocyanate C1 and
(d3) from 0 to 5 mol %, based on the molar amount of component (a1) used for the preparation of P1, of compound D
and in a second step reacting Q2 with
(f1) 0.01-50% by weight, based on polyetheresteramide Q2, of amino carboxylic acid B1,
where the amino carboxylic acid B1 is selected from the group consisting of the natural amino acids, polyamides with a molecular weight not exceeding 18,000 g/mol, obtained by polycondensation of a dicarboxylic acid with 4 to 6 carbon atoms and a diamine with 4 to 10 carbon atoms and compounds which are defined by the formulae IIIa and IIIb ##STR32## where p is an integer from 1 to 1500 and r is an integer from 1 to 4, and G is a radical which is selected from the group consisting of phenylene, --(CH.sub.2).sub.n --, where n is an integer from 1 to 12, --C(R.sup.2)H-- and --C(R.sup.2)HCH.sub.2, where R.sup.2 is methyl or ethyl,
and polyoxazolines with the repeating unit IV ##STR33## where R.sup.3 is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.5 -C.sub.8 -cycl-oalkyl, phenyl which is unsubstituted or substituted up to three times by C.sub.1 -C.sub.4 -alkyl groups, or tetrahydrofuryl, and with
(f2) 0-5 mol %, based on the molar amount of component (a1) used for the preparation of polyetheresteramide Q2, of compound D.

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A process for preparing the biodegradable polymers T3 with a molecular weight (M.sub.n) in the range from 8000 to 80,000 g/mol, with a viscosity number in the range from 30 to 450 g/ml (measured in o-dichlorobenzene/phenol (50/50 ratio by weight) at a concentration of 0.5% by weight of polymer T3 at 25.degree. C.) and a melting point in the range from 50.degree. to 255.degree. C., which comprises in a first step preparing

(g1) polyetheresteramide P2 obtained by reacting a mixture consisting essentially of
(b1) a mixture consisting essentially of
20-95 mol % of adipic acid or ester-forming derivatives thereof or mixtures thereof,
5-80 mol % of terephthalic acid or ester-forming derivatives thereof or mixtures thereof, and
0-5 mol % of a compound containing sulfonate groups,
where the total of the individual mole percentages is 100 mol %,
(b2) a mixture (a2), of dihydroxy compounds, consisting essentially of
(a21) from 15 to 99.3 mol % of a dihydroxy compound selected from the group consisting of C.sub.2 -C.sub.6 -alkanediols and C.sub.5 -C.sub.10 -cycloalkanediols,
(a22) from 0.2 to 85 mol % of a dihydroxy compound containing ether functionalities of the formula I
HO--(CH.sub.2).sub.n --O!.sub.m --H I
where n is 2, 3 or 4 and m is an integer from 2 to 250, or mixtures thereof,
(a23) from 0.5 to 80 mol % of an amino-C.sub.2 -C.sub.12 -alkanol or amino-C.sub.5 -C.sub.10 -cycloalkanol, and
(a24) from 0 to 50 mol % of a diamino-C.sub.1 -C.sub.8 -alkane,
(a25) from 0 to 50 mol % of a 2,2'-bisoxazoline of the formula II ##STR34## where R1 is a single bond, a (CH.sub.2).sub.q alkylene group with q=2, 3 or 4, or a phenylene group, where the total of the individual mole percentages is 100 mol %,
where the molar ratio of (b1) to (b2) is selected in the range from 0.4:1 to 1.25:1,
(b3) from 0.01 to 40% by weight, based on component (b1), of an amino carboxylic acid B1, and
(b4) from 0 to 5 mol %, based on component (b1), of compound D with at least three groups capable of ester formation,
where the amino carboxylic acid B1 is selected from the group consisting of the natural amino acids, polyamides with a molecular weight not exceeding 18,000 g/mol, obtained by polycondensation of a dicarboxylic acid with 4 to 6 carbon atoms and a diamine with 4 to 10 carbon atoms and compounds which are defined by the formulae IIIa and IIIb ##STR35## where p is an integer from 1 to 1500 and r is an integer from 1 to 4, and G is a radical which is selected from the group consisting of phenylene, --(CH.sub.2).sub.n --, where n is an integer from 1 to 12, --C(R.sup.2)H-- and --C(R.sup.2)HCH.sub.2, where R.sup.2 is methyl or ethyl,
and polyoxazolines with the repeating unit IV ##STR36## where R.sup.3 is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.5 -C.sub.8 -cycloalkyl, phenyl which is unsubstituted or substituted up to three times by C.sub.1 -C.sub.4 -alkyl groups, or tetrahydrofuryl,
where the polyesteramide P2 has a molecular weight (M.sub.n) in the range from 5000 to 80,000 g/mol, a viscosity number in the range from 30 to 450 g/ml (measured in o-dichlorobenzene/phenol (50/50 ratio by weight) at a concentration of 0.5% by weight of polyetheresteramide P2 at 25.degree. C.) and a melting point in the range from 50.degree. to 255.degree. C., or
(g2) a mixture consisting essentially of polyetheresteramide P1 obtained by reacting a mixture consisting essentially of
(a1) a mixture consisting essentially of 20-95 mol % of adipic acid or ester-forming derivatives thereof or mixtures thereof,
- 80mol % of terephthalic acid or ester-forming derivatives thereof or mixtures thereof, and
0-5 mol % of a compound containing sulfonate groups,
where the total of the individual mole percentages is 100 mol %, and (a2),
where the molar ratio of (a1) to (a2) is selected in the range from 0.4:1 to 1.5:1,
with the proviso that the polyetheresteramide P1 has a molecular weight (M.sub.n) in the range from 5000 to 80,000 g/mol, a viscosity number in the range from 30 to 450 g/ml (measured in o-dichlorobenzene/phenol (50/50 ratio by weight) at a concentration of 0.5% by weight of polyetheresteramide P1 at 25.degree. C.) and a melting point in the range from 50.degree. to 200.degree. C., and with the further proviso that from 0 to 5 mol %, based on the molar amount of component (a1) used, of a compound D used for the preparation of the polyetheresteramides P1 and 0.01-50% by weight, based on polyetheresteramide P1, of amino carboxylic acid B1, or
(g3) a mixture consisting essentially of polyetheresteramides P1 which differ from one another in composition, and
in a second step reacting (g1) or (g2) or (g3)
with 0.1-5% by weight, based on the amount of the polyetheresteramides used, of diisocyanate Cl and
with 0-5 mol %, based on the particular molar amounts of component (a1) used for the preparation of the polyetheresteramides (g1) to (g3) used, of compound D.

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A process for preparing the biodegradable thermoplastic molding compositions T4, which comprises in a first step preparing

polyetheresteramide P1 obtained by reacting a mixture consisting essentially of
(a1) a mixture consisting essentially of 20-95 mol % of adipic acid or ester-forming derivatives thereof or mixtures thereof,
5-80 mol % of terephthalic acid or ester-forming derivatives thereof or mixtures thereof, and
0-5 mol % of a compound containing sulfonate groups,
where the total of the individual mole percentages is 100 mol %, and
(a2) a mixture of dihydroxy compounds consisting essentially of
(a21) from 15 to 99.3 mol % of a dihydroxy compound selected from the group consisting of C.sub.2 -C.sub.6 -alkanediols and C.sub.5 -C.sub.10 -cycloalkanediols,
(a22) from 0.2 to 85 mol % of a dihydroxy compound containing ether functionalities of the formula I
HO--(CH.sub.2).sub.n --O!.sub.m --H I
where n is 2, 3 or 4 and m is an integer from 2 to 250, or mixtures thereof,
(a23) from 0.5 to 80 mol % of an amino-C.sub.2 -C.sub.12 -alkanol or amino-C.sub.5 -C.sub.10 -cycloalkanol, and
(a24) from 0 to 50 mol % of a diamino-C.sub.1 -C.sub.8 -alkane,
(a25) from 0 to 50 mol % of a 2,2'-bisoxazoline of the formula II ##STR37## where R.sup.1 is a single bond, a (CH.sub.2).sub.q alkylene group with q=2, 3 or 4, or a phenylene group, where the total of the individual mole percentages is 100 mol %,
where the molar ratio of (a1) to (a2) is selected in the range from 0.4:1 to 1.5:1,
with the proviso that the polyetheresteramide P1 has a molecular weight (M.sub.n) in the range from 5000 to 80,000 g/mol, a viscosity number in the range from 30 to 450 g/ml (measured in o-dichlorobenzene/phenol (50/50 ratio by weight) at a concentration of 0.5% by weight of polyetheresteramide P1 at 25.degree. C.) and a melting point in the range from 50.degree. to 200.degree. C., and with the further proviso that from 0 to 5 mol %, based on the molar amount of component (a1) used, of a compound D with at least three groups capable of ester formation is used to prepare the polyetheresteramides P1 or polyetheresteramide Q2 with a molecular weight (M.sub.n) in the range from 6000 to 80,000 g/mol, a viscosity number in the range from 30 to 450 g/ml (measured in o-dichlorobenzene/phenol (50/50 ratio by weight) at a concentration of 0.5% by weight of polyetheresteramide Q2 at 25.degree. C.) and a melting point in the range from 50.degree. to 200.degree. C., obtained by reacting a mixture consisting essentially of
(d1) from 95 to 99.9% by weight of polyetheresteramide P1,
(d2) from 0.1 to 5% by weight of a diisocyanate C1 and
(d3) from 0 to 5 mol %, based on the molar amount of component (a1) used for the preparation of P1, of compound D and in a second step mixing
99.5-0.5% by weight of P1 or Q2 with 0.5-99.5% by weight of hydroxy carboxylic acid H1.

16 more elements

Biodegradable polymers, process for the preparation thereof and the use thereof for producing biodegradable moldings

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Biodegradable polymers, process for the preparation thereof and the use thereof for producing biodegradable moldings

Life of this patent

Abstract

Claims21