Ionene polymers containing biologically-active anions
First Claim
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1. A water-soluble ionene polymer of formula I:
- ##STR3## wherein n is an integer from 4 to 400 corresponding to the degree of polymerization of the polymer;
R1, R2, R3 and R4 represent the same or different substituent selected from the group consisting of hydrogen, a C1 to C16 alkyl group, a C1 to C16 alkyl group substituted with one or more hydroxyl groups, a benzyl group, and a benzyl group substituted with one or more C1 to C16 alkyl groups;
B represents a divalent C2 to C16 aliphatic hydrocarbon radical which can be substituted by hydroxyl, a divalent C5 to C9 cyclic hydrocarbon radical, a di-(C2 to C6)-alkylene ether, a phenylene or alkyl-substituted phenylene radical, or the divalent group R1 R2 NBNR3 R4 of formula I represents a divalent radical of the structure;
space="preserve" listing-type="equation">R.sub.1 R.sub.2 N--(CH.sub.2).sub.p --NR.sub.5 --C(O)--NR.sub.6 --(CH.sub.2).sub.p --NR.sub.3 R.sub.4 where p is an integer from 2 to 6, R1, R2, R3 and R4 are the same as defined above, and R5 and R6 are the same or different and are selected from the group consisting of hydrogen and a C1 to C16 alkyl group, or the divalent radical R1 R2 NBNR3 R4 forms a heterocyclic group selected from 1,2-pyrazolidinyl, 1,3-imidazolindiyl, 1,4-piperazindiyl, aminopyrrolidinyl, or aminopiperidiyl wherein the heterocyclic group may be substituted with one or more groups selected from a C1 to C6 alkyl group, a hydroxyl group, a halide, or a phenyl group;
A- is an anion derived from a biologically-active compound having at least one acid functionality with the proviso that said anion is not a halide anion;
X- is an anion derived from a mineral or organic acid; and
the degree of substitution of the polymer is from about 0.005 to 0.5.
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Abstract
Ionene polymers having biologically-active organic and/or inorganic anions are described. Methods to prepare the ionene polymers, compositions containing them and their methods of use are also described.
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Citations
71 Claims
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1. A water-soluble ionene polymer of formula I:
- ##STR3## wherein n is an integer from 4 to 400 corresponding to the degree of polymerization of the polymer;
R1, R2, R3 and R4 represent the same or different substituent selected from the group consisting of hydrogen, a C1 to C16 alkyl group, a C1 to C16 alkyl group substituted with one or more hydroxyl groups, a benzyl group, and a benzyl group substituted with one or more C1 to C16 alkyl groups; B represents a divalent C2 to C16 aliphatic hydrocarbon radical which can be substituted by hydroxyl, a divalent C5 to C9 cyclic hydrocarbon radical, a di-(C2 to C6)-alkylene ether, a phenylene or alkyl-substituted phenylene radical, or the divalent group R1 R2 NBNR3 R4 of formula I represents a divalent radical of the structure;
space="preserve" listing-type="equation">R.sub.1 R.sub.2 N--(CH.sub.2).sub.p --NR.sub.5 --C(O)--NR.sub.6 --(CH.sub.2).sub.p --NR.sub.3 R.sub.4where p is an integer from 2 to 6, R1, R2, R3 and R4 are the same as defined above, and R5 and R6 are the same or different and are selected from the group consisting of hydrogen and a C1 to C16 alkyl group, or the divalent radical R1 R2 NBNR3 R4 forms a heterocyclic group selected from 1,2-pyrazolidinyl, 1,3-imidazolindiyl, 1,4-piperazindiyl, aminopyrrolidinyl, or aminopiperidiyl wherein the heterocyclic group may be substituted with one or more groups selected from a C1 to C6 alkyl group, a hydroxyl group, a halide, or a phenyl group; A- is an anion derived from a biologically-active compound having at least one acid functionality with the proviso that said anion is not a halide anion; X- is an anion derived from a mineral or organic acid; and
the degree of substitution of the polymer is from about 0.005 to 0.5. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71)
- ##STR3## wherein n is an integer from 4 to 400 corresponding to the degree of polymerization of the polymer;
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18. A water-soluble ionene polymer of formula II:
- ##STR7## wherein n is an integer from 4 to 400 corresponding to the degree of polymerization of the polymer;
R1, R2, R3 and R4 represent the same or different substituent selected from the group consisting of hydrogen, a C1 to C16 alkyl group, a C1 to C16 alkyl group substituted with one or more hydroxyl groups, a benzyl group and a benzyl group substituted with one or more C1 to C16 alkyl groups; B represents a divalent C2 to C16 aliphatic hydrocarbon radical which can be substituted by hydroxyl, a divalent C5 to C9 cyclic hydrocarbon radical, a di-(C2 to C6)-alkylene ether, a phenylene or alkyl-substituted phenylene radical or the divalent group R1 R2 NBNR3 R4 of formula II represents a divalent radical of the structure;
space="preserve" listing-type="equation">R.sub.1 R.sub.2 N--(CH.sub.2).sub.p --NR.sub.5 --C(O)--NR.sub.6 --(CH.sub.2).sub.p --NR.sub.3 R.sub.4where p is an integer from 2 to 6, R1, R2, R3, and R4 are the same as defined above, and R5 and R6 are the same or different and are selected from the group consisting of hydrogen and a C1 to C16 alkyl group, or the divalent radical R1 R2 NBNR3 R4 forms a heterocyclic group selected from 1,2-pyrazolidinyl, 1,3-imidazolindiyl, 1,4-piperazindiyl, aminopyrrolidinyl, or aminopiperidiyl wherein the heterocyclic group may be substituted with one or more groups selected from a C1 to C6 alkyl group, a hydroxyl group, a halide, or a phenyl group; A- is an anion derived from a biologically-active compound having at least one acid functionality with the proviso that said anion is not a halide anion; X- is an anion derived from a mineral or organic acid; and
the degree of substitution of the polymer is from about 0.005 to 0.333. - View Dependent Claims (19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34)
- ##STR7## wherein n is an integer from 4 to 400 corresponding to the degree of polymerization of the polymer;
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35. A method for the preparation of an ionene polymer having a biologically-active anion comprising the steps of
a) reacting a protonated diamine having at least one anion derived from a biologically-active compound, with the proviso that said anion is not a halide anion with an epihalohydrin, and b) polymerizing the product of step a) with a secondary amine or a diamine.
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36. A compound of formula VI:
- ##STR11## wherein R1, R2, R3 and R4 represent the same or different substituent selected from the group consisting of hydrogen, a C1 to C16 alkyl group, a C1 to C16 alkyl group substituted with one or more hydroxyl groups, a benzyl group and a benzyl group substituted with one or more C1 to C16 alkyl groups;
B represents a divalent C2 to C16 aliphatic hydrocarbon radical which can be substituted by hydroxyl, a divalent C5 to C9 cyclic hydrocarbon radical, a di-(C2 to C6)-alkylene ether, a phenylene or alkyl-substituted phenylene radical, or the divalent group R1 R2 NBNR3 R4 in formula VI represents a divalent radical of the structure;
space="preserve" listing-type="equation">R.sub.1 R.sub.2 N--(CH.sub.2).sub.p --NR.sub.5 --C(O)--NR.sub.6 --(CH.sub.2).sub.p --NR.sub.3 R.sub.4where p is an integer from 2 to 6 and R5 and R6 are the same or different and selected from the group consisting of hydrogen and a C1 to C16 alkyl group, or the divalent radical R1 R2 NBNR3 R4 forms a heterocyclic group selected from 1,2-pyrazolidinyl, 1,3-imidazolindiyl, 1,4-piperazindiyl, aminopyrrolidinyl, or aminopiperidiyl wherein the heterocyclic group may be substituted with one or more groups selected from a C1 to C6 alkyl group, a hydroxyl group, a halide, or a phenyl group; A- is an anion derived from a biologically-active compound having at least one acid functionality with the proviso that said anion is not a halide anion; and X- is an anion derived from a mineral acid. - View Dependent Claims (37, 38, 39, 40, 41)
- ##STR11## wherein R1, R2, R3 and R4 represent the same or different substituent selected from the group consisting of hydrogen, a C1 to C16 alkyl group, a C1 to C16 alkyl group substituted with one or more hydroxyl groups, a benzyl group and a benzyl group substituted with one or more C1 to C16 alkyl groups;
Specification