US 6,441,089 B1Granted

Water-soluble polymers and compositions thereof

AssigneeThe Regents of the University of California

InventorsBarbara F. Smith, Thomas W. Robison, Joel W. Gohdes

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Abstract

Water-soluble polymers including functionalization from the group of amino groups, carboxylic acid groups, phosphonic acid groups, phosphonic ester groups, acylpyrazolone groups, hydroxamic acid groups, aza crown ether groups, oxy crown ethers groups, guanidinium groups, amide groups, ester groups, aminodicarboxylic groups, permethylated polvinylpyridine groups, permethylated amine groups, mercaptosuccinic acid groups, alkyl thiol groups, and N-alkylthiourea groups are disclosed.

Claims11

Dependent claims

A water soluble polymer of the formula

wherein X1, X2, and X3 in each unit of the polymer is a group independently selected from a substituent selected from H, C(O)CH2CH(SH)COOH,
—(CH2)mYZp
where m is an integer from 0 to 4, Y is selected from C═O, P═O, C═S, SO2, C(O)CH2C(O), and S, Z is selected from an amine, alkylamine, arylamine, hydroxyl, oxyalkyl, oxyaryl, hydroxylamine, alkylhydroxylamine, arylhydroxylamine, thiol, alkylthiol, alkyl, aryl, dimethylpyrazolone, methylphenylpyrazolone, dimethylpyrazol-thione, methylphenylpyrazol-thione, oxycrown ethers, azacrown ethers, thiocrown ethers, and H, p is an integer from 1 to 2, and n is an integer between about 12 and 12,000;
where m is an integer from 0 to 6, Y is selected from C═O, P═O, and C═S, R1 and R2 are selected from an amine, alkylamine, arylamine, hydroxyl, oxyalkyl, oxyaryl, hydroxylamine, alkylhydroxylamine, arylhydroxylamine, thiol, alkylthiol, alkyl, aryl, and H, p is an integer from 1 to 2, and n is an integer between about 12 and 12,000;
wherein X4 and X5 in each unit of the polymer is a group independently selected from a substituent selected from H, C(O)CH2CH(SH)COOH,
—(CH2)mYZp
where q is an integer from 0 to 4, m is an integer from 0 to 4, Y is selected from C═O, P═O, C═S, SO2, C(O)CH2C(O), and S, Z is selected from an amine, alkylamine, arylamine, hydroxyl, oxyalkyl, oxyaryl, hydroxylamine, alkylhydroxylamine, arylhydroxylamine, thiol, alkylthiol, alkyl, aryl, dimethylpyrazolone, methylphenylpyrazolone, dimethylpyrazol-thione, methylphenylpyrazol-thione, oxycrown ethers, azacrown ethers, thiocrown ethers, and H, p is an integer from 1 to 2, and n is an integer between about 24 and 24,000;
wherein X6 in each unit of the polymer is a group independently selected from a substituent selected from C(O)CH2CH(SH)COOH,
—(CH2)mYZp
where m is an integer from 0 to 4, Y is selected from C═O, P═O, C═S, SO2, C(O)CH2C(O), and S;
Z is selected from an amine, alkylamine, arylamine, hydroxyl, oxyalkyl, oxyaryl, hydroxylamine, alkylhydroxylamine, arylhydroxylamine, thiol, alkylthiol, alkyl, aryl, dimethylpyrazolone, methylphenylpyrazolone, dimethylpyrazol-thione, methylphenylpyrazol-thione, oxycrown ethers, azacrown ethers, thiocrown ethers, and H, p is an integer from 1 to 2, and n is an integer between about 24 and 24,000;
—(CHX7—CH2)n—(CH2—CX8X9)m— (iv)
wherein X7, X8, and X9 in each unit of the polymer is a group independently selected from a substituent selected from C(O)CH2CH(SH)COOH,
—(CH2)mYZp
where m is an integer from 0 to 4, Y is selected from C═O, P═O, C═S, SO2, C(O)CH2C(O), and S, Z is selected from an amine, alkylamine, arylamine, hydroxyl, oxyalkyl, oxyaryl, hydroxylamine, alkylhydroxylamine, arylhydroxylamine, thiol, alkylthiol, alkyl, aryl, dimethylpyrazolone, methylphenylpyrazolone, dimethylpyrazol-thione, methylphenylpyrazol-thione, oxycrown ethers, azacrown ethers, thiocrown ethers, and H, p is an integer from 1 to 2, and n is an integer between about 12 and 12,000;
or
wherein X10 and X11 in each unit of the polymer are a thiolactum or are a group independently selected from a substituent selected from C(O)CH2CH(SH)COOH, and
—(CH2)mYZp
where m is an integer from 0 to 4, Y is selected from C═O, P═O, C═S, SO2, C(O)CH2C(O), and S;
Z is selected from an amine, alkylamine, arylamine, hydroxyl, oxyalkyl, oxyaryl, hydroxylamine, alkylhydroxylamine, arylhydroxylamine, thiol, alkylthiol, alkyl, aryl, dimethylpyrazolone, methylphenylpyrazolone, dimethylpyrazol-thione, methylphenylpyrazol-thione, oxycrown ethers, azacrown ethers, thiocrown ethers, and H, p is an integer from 1 to 2, and n is an integer between about 24 and 24,000, said water-soluble polymer having a molecular weight of greater than about 10,000 and further characterized as essentially free of molecular weights less than about 10,000.

17 more elements

Dependencies are inferred from the claim text.

Facts

Application: 09/287,303Filed 6 Apr 1999 · division
Priority: 30 May 1995
Granted: 27 Aug 2002
Term ends: Not estimatedThe source records don’t support an estimate.

Classification7 codes

C02F 1/683
By addition of specified substances, e.g. trace elements, for ameliorating potable water: by addition of complex-forming compounds
C08F 226/00
Copolymers of compounds having one or more unsaturated aliphatic radicals, each having
C08G 73/0206
Polyamines: polyalkyleneamines
C02F 2101/20
Inorganic compounds: heavy metals or heavy metal compounds

Family

Application08/454,451Parent of this division · filed 30 May 1995
US 5,891,956 AParent of this division · filed 6 Apr 1999
US 6,441,089 B1This patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

A water soluble polymer of the formula

wherein X1, X2, and X3 in each unit of the polymer is a group independently selected from a substituent selected from H, C(O)CH2CH(SH)COOH,
—(CH2)mYZp
where m is an integer from 0 to 4, Y is selected from C═O, P═O, C═S, SO2, C(O)CH2C(O), and S, Z is selected from an amine, alkylamine, arylamine, hydroxyl, oxyalkyl, oxyaryl, hydroxylamine, alkylhydroxylamine, arylhydroxylamine, thiol, alkylthiol, alkyl, aryl, dimethylpyrazolone, methylphenylpyrazolone, dimethylpyrazol-thione, methylphenylpyrazol-thione, oxycrown ethers, azacrown ethers, thiocrown ethers, and H, p is an integer from 1 to 2, and n is an integer between about 12 and 12,000;
where m is an integer from 0 to 6, Y is selected from C═O, P═O, and C═S, R1 and R2 are selected from an amine, alkylamine, arylamine, hydroxyl, oxyalkyl, oxyaryl, hydroxylamine, alkylhydroxylamine, arylhydroxylamine, thiol, alkylthiol, alkyl, aryl, and H, p is an integer from 1 to 2, and n is an integer between about 12 and 12,000;
wherein X4 and X5 in each unit of the polymer is a group independently selected from a substituent selected from H, C(O)CH2CH(SH)COOH,
—(CH2)mYZp
where q is an integer from 0 to 4, m is an integer from 0 to 4, Y is selected from C═O, P═O, C═S, SO2, C(O)CH2C(O), and S, Z is selected from an amine, alkylamine, arylamine, hydroxyl, oxyalkyl, oxyaryl, hydroxylamine, alkylhydroxylamine, arylhydroxylamine, thiol, alkylthiol, alkyl, aryl, dimethylpyrazolone, methylphenylpyrazolone, dimethylpyrazol-thione, methylphenylpyrazol-thione, oxycrown ethers, azacrown ethers, thiocrown ethers, and H, p is an integer from 1 to 2, and n is an integer between about 24 and 24,000;
wherein X6 in each unit of the polymer is a group independently selected from a substituent selected from C(O)CH2CH(SH)COOH,
—(CH2)mYZp
where m is an integer from 0 to 4, Y is selected from C═O, P═O, C═S, SO2, C(O)CH2C(O), and S;
Z is selected from an amine, alkylamine, arylamine, hydroxyl, oxyalkyl, oxyaryl, hydroxylamine, alkylhydroxylamine, arylhydroxylamine, thiol, alkylthiol, alkyl, aryl, dimethylpyrazolone, methylphenylpyrazolone, dimethylpyrazol-thione, methylphenylpyrazol-thione, oxycrown ethers, azacrown ethers, thiocrown ethers, and H, p is an integer from 1 to 2, and n is an integer between about 24 and 24,000;
—(CHX7—CH2)n—(CH2—CX8X9)m— (iv)
wherein X7, X8, and X9 in each unit of the polymer is a group independently selected from a substituent selected from C(O)CH2CH(SH)COOH,
—(CH2)mYZp
where m is an integer from 0 to 4, Y is selected from C═O, P═O, C═S, SO2, C(O)CH2C(O), and S, Z is selected from an amine, alkylamine, arylamine, hydroxyl, oxyalkyl, oxyaryl, hydroxylamine, alkylhydroxylamine, arylhydroxylamine, thiol, alkylthiol, alkyl, aryl, dimethylpyrazolone, methylphenylpyrazolone, dimethylpyrazol-thione, methylphenylpyrazol-thione, oxycrown ethers, azacrown ethers, thiocrown ethers, and H, p is an integer from 1 to 2, and n is an integer between about 12 and 12,000;
or
wherein X10 and X11 in each unit of the polymer are a thiolactum or are a group independently selected from a substituent selected from C(O)CH2CH(SH)COOH, and
—(CH2)mYZp
where m is an integer from 0 to 4, Y is selected from C═O, P═O, C═S, SO2, C(O)CH2C(O), and S;
Z is selected from an amine, alkylamine, arylamine, hydroxyl, oxyalkyl, oxyaryl, hydroxylamine, alkylhydroxylamine, arylhydroxylamine, thiol, alkylthiol, alkyl, aryl, dimethylpyrazolone, methylphenylpyrazolone, dimethylpyrazol-thione, methylphenylpyrazol-thione, oxycrown ethers, azacrown ethers, thiocrown ethers, and H, p is an integer from 1 to 2, and n is an integer between about 24 and 24,000, said water-soluble polymer having a molecular weight of greater than about 10,000 and further characterized as essentially free of molecular weights less than about 10,000.

17 more elements

Facts

Application

09/287,303Filed 6 Apr 1999 · division

Priority

30 May 1995

Granted

27 Aug 2002

Term ends

Not estimatedThe source records don’t support an estimate.

Classification7 codes

C02F 1/683
By addition of specified substances, e.g. trace elements, for ameliorating potable water: by addition of complex-forming compounds
C08F 226/00
Copolymers of compounds having one or more unsaturated aliphatic radicals, each having
C08G 73/0206
Polyamines: polyalkyleneamines
C02F 2101/20
Inorganic compounds: heavy metals or heavy metal compounds