Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Reexamination Certificate
1999-08-31
2002-04-30
Pezzuto, Helen L. (Department: 1713)
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
C560S008000, C560S019000, C526S268000, C526S259000, C526S260000, C526S280000
Reexamination Certificate
active
06380431
ABSTRACT:
FIELD OF THE INVENTION
This invention relates to the field of fluorescent moieties. Also described are water-soluble polymers incorporating fluorescent moieties. In addition, a method for determining the efficiency of polymers incorporating fluorescent moieties as water treatment agents is also disclosed.
BACKGROUND OF THE INVENTION
In many fields that employ polymers it may be desirable to tag or mark such polymers to facilitate monitoring thereof. By the term “monitoring” is meant herein any type of tracing or tracking to determine the location or route of the polymers, and any type of determination of the concentration or amount of the polymer at any given site, including singular or intermittent or continuous monitoring. For instance, it may be desirable to monitor Water treatment polymers in water systems, or to monitor polymers that may be present in waste fluids before disposal, or to monitor the polymer used for down-hole oil well applications, or to monitor polymers that may be present in fluids used to wash a manufactured product.
As seen from the above list of possible applications of polymer monitoring, the purpose of such monitoring may be to trace or track or determine the level of the polymer itself, or to trace or track or determine the level of some substance in association with the polymer, or to determine some property of the polymer or substance in association with the polymer, for instance its leachability.
Conventional techniques for monitoring polymers are generally time-consuming and labor intensive, and often require the use of bulky and/or costly equipment. Most conventional polymer analysis techniques require the preparation of calibration curves for each type of polymer employed, which is time-consuming and laborious, particularly when a large variety of polymer chemistries are being employed, and the originally prepared calibration curves lose their accuracy if the polymer structures change, for instance an acrylic acid ester mer unit being hydrolyzed to an acrylic acid mer unit.
Polymers tagged with pendant fluorescent groups are capable of being monitored, even when present at low concentrations. Some polymers tagged with pendant fluorescent groups are known. A process for preparing a polymer from the copolymerization of a fluorescent compound wherein an acrylamide moiety and the aromatic fluorescing moiety are directly linked through an amide bond to the aromatic ring is disclosed in Japanese Patent No. 1,141,147. Other fluorescent acrylamide based polymers are disclosed in U.S. Pat. Nos. 5,043,406 and 4,999,456. Polymers tagged with pendant fluorescent groups have been prepared by the transamidation derivatization of the pre-existing polymers having carbonyl-type pendant groups in U.S. Pat. No. 5,128,419. Another post-polymerization modification of a polyacrylamide with a fluorescing moiety is disclosed in U.S. Pat. No. 4,813,973. The preparation of certain vinylic coumarin derivatives is disclosed in
Collection Czechoslov. Chem Common
, Vol. 45, 1980, pgs. 727-731.
What are needed are additional fluorescent moieties that can be incorporated into tagged polymers which can be used in a variety of applications.
SUMMARY OF THE INVENTION
The first aspect of the invention are fluorescent monomers selected from the group consisting of:
wherein a is an integer of from 1 to 10, R
1
is selected from the group consisting of hydrogen and methyl groups, R
2
and R
3
are methyl groups, R
8
is methyl, and R
9
is selected from the group consisting of NH and O;
where R
6
is either hydrogen or methyl; and
where R
7
is either hydrogen or methyl.
The second aspect of this invention is a water-soluble polymer of Formula Useful comprising from about 0.001 to about 10.0 mole percent of a Repeating Mer Unit represented by the formula:
wherein a is an integer of from 1 to 10, R
1
is selected from the group consisting of hydrogen and methyl groups, R
2
and R
3
are methyl groups, and R
9
is selected from the group consisting of NH and O; TAG is a fluorescing moiety selected from the group consisting of:
wherein the TAG is connected to the remainder of the mer unit thru the bond attached to the methylene group (—CH
2
—) at the “top” of each TAG;
where R
8
is methyl;
O-&bgr;-Gal is &bgr;-D-galactopyranoside;
and X, X
−
a
and X
−
b
are selected from the group consisting of chloride, iodide, sulfate, acetate, benzoate, phosphate and bromide;
wherein the polymer of Formula Useful also comprises from about 90.0 to about 99.999 mole percent of one or more randomly distributed (one or more randomly distributed including block configurations) water-soluble vinylic mer units selected from one or more monomer groups consisting of acrylamide, methacrylamide, N,N-dimethylacrylamide, N,N-diethylacrylamide, acrylic acid, sodium acrylate, ammonium acrylate, methacrylic acid, sodium methacrylate, ammonium methacrylate, dimethylaminoethyl acrylate methyl chloride quaternary salt, dimethylaminoethyl acrylate benzyl chloride quaternary salt, dimethylaminoethyl acrylate methyl sulfate quaternary salt, dimethylaminoethyl methacrylate methyl sulfate quaternary salt, dimethylaminopropyl acrylamide methyl sulfate quaternary salt, dimethylaminopropyl methacrylamide methyl sulfate quaternary salt, diallyldimethylammonium chloride, N-vinylformamide, dimethylaminoethyl methacrylate acid salts, including, but not limited to, sulfuric acid salts and hydrochloric acid salts, dimethylaminoethyl methacrylate methyl chloride quaternary salt, dimethylaminoethyl methacrylate benzyl chloride quaternary salt, methacrylamidopropyltrimethylammonium chloride, acrylamidopropyltrimethylammonium chloride, N,N-methylenebisacrylamide, triallylamine, acid salts of triallylamine, ethylene glycol dimethacrylate, N-vinyl pyrrolidone, 2-acrylamido-2-methyl-1-propanesulfonic acid (AMPS), the sodium salt of AMPS, hydroxyethyl methacrylate, hydroxyethyl acrylate, hydroxypropyl acrylate, hydroxypropyl methacrylate, sodium vinyl sulfonate, styrene sulfonate, maleic acid, sodium salt of maleic acid, ammonium salt of maleic acid, N-isopropylacrylamide, diethylene glycol dimethacrylate, triethylene glycol, dimethylacrylate and polyethylene glycol dimethacrylate.
The third aspect of this invention is the use of polymers of Formula Useful as water soluble polymeric treating agents, wherein said polymer of Formula Useful comprises from about 0.001 to about 10.0 mole percent of a Repeating Mer Unit represented by the formula:
wherein a is an integer of from 1 to 10, R
1
is selected from the group consisting of hydrogen and methyl groups, R
2
and R
3
are methyl groups, and R
9
is selected from the group consisting of NH and O; TAG is a fluorescing moiety selected from the group consisting of:
wherein the TAG is connected to the remainder of the mer unit thru the bond attached to the methylene group (—CH
2
—) at the “top” of each TAG;
where R
8
is methyl;
O-&bgr;-Gal is &bgr;-D-galactopyranoside;
and X, X
−
a
and X
−
b
are selected from the group consisting of chloride, iodide, sulfate, acetate, benzoate, phosphate and bromide;
wherein the polymer of Formula Useful also comprises from about 90.0 to about 99.999 mole percent of one or more randomly distributed (one or more randomly distributed including block configurations) water-soluble vinylic mer units selected from one or more monomer groups consisting of acrylamide, methacrylamide, N,N-dimethylacrylamide, N,N-diethylacrylamide, acrylic acid, sodium acrylate, ammonium acrylate, methacrylic acid, sodium methacrylate, ammonium methacrylate, dimethylaminoethyl acrylate methyl chloride quaternary salt, dimethylaminoethyl acrylate benzyl chloride quaternary salt, dimethylaminoethyl acrylate methyl sulfate quaternary salt, dimethylaminoethyl methacrylate methyl sulfate quaternary salt, dimethylaminopropyl acrylamide methyl sulfate quaternary salt, dimethylaminopropyl methacrylamide methyl sulfate quaternary salt, diallyldimethylammonium chloride, N-vinylformamide, dimethylaminoethyl methacrylate acid salts, including, but not limited to
Murray Patrick G.
Whipple Wesley L.
Breininger Thomas M.
Brumm Margaret M.
Nalco Chemical Company
Pezzuto Helen L.
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