Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Mixing of two or more solid polymers; mixing of solid...
Reexamination Certificate
1999-04-06
2002-08-27
Henderson, Christopher (Department: 1713)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Mixing of two or more solid polymers; mixing of solid...
C525S349000, C525S056000, C525S359400, C525S185000, C525S359500
Reexamination Certificate
active
06441089
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to water-soluble polymers and compositions thereof, such water-soluble polymers and compositions thereof useful, e.g., in processes for selective separation of metal ions from aqueous streams, and processes for the selective separation of metals from solid matrixes.
BACKGROUND OF THE INVENTION
Water-soluble polymers are well known for the retention or recovery of certain metal ions from solutions under certain conditions, e.g., certain pH conditions (see, e.g., Pure and Applied Chemistry, Vol. 52, pp. 1883-1905 (1980), Talanta, vol. 36, No. 8, pp. 861-863 (1989), and U.S. Pat. No. 4,741,831). Additionally, higher molecular weight varieties of the water-soluble polymers such as polyethyleneimine have been used as coatings on, e.g. silica gel, for separation and recovery of metal ions. However, the selectivity of the polymer for target metals due to competition from competing or interfering ions within solutions can present unique challenges.
It is an object of the present invention to provide novel water-soluble polymers.
It is a further object of the invention to provide compositions of water-soluble polymers having defined molecular weight ranges.
Still another object of the present invention is to provide compositions of water-soluble polymers including at least two different water-soluble polymers, the different water-soluble polymers differing in functionality, molecular weight range or both.
SUMMARY OF THE INVENTION
To achieve the foregoing and other objects, and in accordance with the purposes of the present invention, as embodied and broadly described herein, the present invention provides a water soluble polymer of the formula
wherein X
1
, X
2
, and X
3
in each unit of the polymer is a group independently selected from a substituent selected from H, C(O)CH
2
CH(SH)COOH,
—(CH
2
)
m
YZ
p
where when m is an integer selected from 0, 2, 3, and 4, Y is selected from C═O, P═O, C═S, SO
2
, C(O)CH
2
C(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, and when m is 1, Y is selected from C═O, C═S, SO
2
, C(O)CH
2
C(O), and S, Z is selected from an amine, alkylamine, arylamine, 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
where m is an integer from 0 to 6, Y is selected from C═O, P═O, and C═S, R
1
and R
2
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 with the proviso that at least one of X
1
, X
2
, and X
3
is not hydrogen;
wherein X
4
and X
5
in each unit of the polymer is a group independently selected from a substituent selected from H, C(O)CH
2
CH(SH)COOH,
—(CH
2
)
m
YZ
p
where q is an integer from 0 to 4, and where when m is an integer selected from 0, 2, 3, and 4, Y is selected from C═O, P═O, C═S, SO
2
, C(O)CH
2
C(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, and when m is 1, Y is selected from C═O, C═S, SO
2
, C(O)CH
2
C(O), and S, Z is selected from an amine, alkylamine, arylamine, 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 with the proviso that at least one of X
4
and X
5
is not hydrogen;
wherein X
6
in each unit of the polymer is a group independently selected from a substituent selected from C(O)CH
2
CH(SH)COOH,
—(CH
2
)
m
YZ
p
where m is an integer selected from 0, 2, 3, and 4, Y is selected from C═O, P═O, C═S, SO
2
, C(O)CH
2
C(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, and when m is 1, Y is selected from C═O, C═S, SO
2
, C(O)CH
2
C(O), and S, Z is selected from an amine, alkylamine, arylamine, 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;
—(CHX
7
—CH
2
)
n
—(CH
2
—CX
8
X
9
)
m
— (iv)
wherein X
7
and X
8
, and X
9
in each unit of the polymer is a group independently selected from a substituent selected from C(O)CH
2
CH(SH)COOH,
—(CH
2
)
m
YZ
p
where m is an integer selected from 0, 2, 3, and 4, Y is selected from C═O, P═O, C═S, SO
2
, C(O)CH
2
C(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, and when m is 1, Y is selected from C═O, C═S, SO
2
, C(O)CH
2
C(O), and S, Z is selected from an amine, alkylamine, arylamine, 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 X
10
and X
11
in each unit of the polymer are a thiolactum or are a group independently selected from a substituent selected from C(O)CH
2
CH(SH)COOH, and
—(CH
2
)
m
YZ
p
where m is an integer from 0 to 4, Y is selected from C═O, P═O, C═S, SO
2
, C(O)CH
2
C(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.
The present invention also provides a water soluble polymer of the formula
wherein X
1
, X
2
, and X
3
in each unit of the polymer is a group independently selected from a substituent selected from H, C(O)CH
2
CH(SH)COOH,
—(CH
2
)
m
YZ
p
where m is an integer from 0 to 4, Y is selected from C═O, P═O, C═S, SO
2
, C(O)CH
2
C(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
Gohdes Joel W.
Robison Thomas W.
Smith Barbara F.
Cottrell Bruce H.
Henderson Christopher
The Regents of the University of California
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