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US 9,751,789 B2Granted
Fluorescent monomers and tagged treatment polymers containing same for use in industrial water systems
AssigneeEcolab USA Inc.
InventorsJeffery M Atkins, Barbara E. Moriarty, Paul J. Zinn
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Abstract
The invention is directed towards methods and compositions for making and using fluorescent monomers which are synthesized by reacting a substituted or non-substituted benzoxanthene anhydride with an amine and with a moiety containing a polymerizable group. Such monomers are useful for the preparation of tagged treatment polymers. Such tagged treatment polymers are useful as scale inhibitors in industrial water systems.
Claims21
A method of monitoring an industrial water system, comprising:
- (a) adding an inert tracer and a tagged treatment polymer to water resulting in a tagged treatment polymer concentration;
- (b) detecting fluorescent signals from the inert tracer and the tagged treatment polymer;
- (c) adjusting the amount of tagged treatment polymer concentration in the water;
- wherein the tagged treatment polymer is selected from GaQjWt, Ga QvWf Sc, or combinations thereof;
- and wherein
- G, Q, W and S are each monomer moieties making up a backbone of a polymer chain, the distribution of G, Q, W and S along the polymer chain are in random order and in relative amounts of a, j, t, v, f, and c;
- for polymer Ga Qv Wf Sc, a is from about 0.001 to about 10.00 mole percent;
- v is from about 0 to about 97.999 mole percent;
- f is from about 1 to about 97.999 mole percent;
- c is from about 1 to about 40 mole percent, and the sum of a, v, f, and c is 100;
- for polymer GaQjWt, a is from about 0.001 to about 10.0 mole percent;
- j is from about 0 to about 99.999 mole percent;
- t is from about 0.001 to about 99.999 mole percent, and the sum of a, j, and t is 100;
- G is selected from Formula I or Formula II
- in Formula I, each Y is selected from H, F, Cl, Br, NO2, CO2H and its salts, PO3H2 and it salts, SO3H and its salts, SO2NH2 or SO2NR1R2;
- Z is one of the following:
- CH2, C═O, NH, NR1, NH2+, NOH, O, S, SO, or SO2;
- R3 is selected from allyl, 2-hydroxy-3-allyloxy-propyl, vinyl benzyl, 3-methacrylamidopropyl, 3-acrylamidopropyl, 2-acryloxyethyl or 2-methacryloxyethyl;
- A is absent or selected from alkyl, alkyloxyalkyl, alkylamidoalkyl, or aryl, with the proviso that when A is absent, B is nitrogen (N) and B is bonded directly to the imide nitrogen;
- B is sulfur or nitrogen with the proviso that when B is sulfur only one of R1 or R2 is present;
- X is an anionic counter ion;
- in Formula II, each Y is selected from H, F, Cl, Br, NO2, CO2H and its salts, PO3H2 and it salts, SO3H and its salts, SO2NH2 or SO2NR1R2;
- Z is selected from CH2, C═O, NH, NR, NR2+, NOH, O, S, SO, or SO2;
- A is absent or selected from alkyl, alkyloxyalkyl, alkoxy, alkylamidoalkyl, alkylamino, NH, or aryl;
- R4 is selected from allyl, acryl, methacryl, 2-hydroxy-3-allyloxy-propyl, vinyl benzyl, 2-acryloxyethyl or 2-methacryloxyethyl;
- R1 and R2 are independently alkyl;
- Q is selected from acrylic acid and salts thereof, methacrylic acid and salts thereof, maleic acid and salts thereof, maleic anhydride, acrylamide, crotonic acid, acrylamidomethylpropane sulfonic acid or salts thereof;
- and Q cannot be the same as W;
- W is selected from acrylic acid and salts thereof, methacrylic acid and salts thereof, itaconic acid and salts thereof, maleic acid and salts thereof, maleic anhydride, crotonic acid and salts thereof, acrylamide, methacrylamide, vinyl sulfonic acid, styrene sulfonate, N-tertbutylacrylamide, N-isopropylacrylamide, butoxymethylacrylamide, N,N-dimethylacrylamide, N,N-diethylacrylamide, dimethylaminoethyl acrylate methyl chloride quaternary salts, dimethylaminoethyl acrylate benzyl chloride quaternary salts, dimethylaminoethyl acrylate methyl sulfate quaternary salt, dimethylaminoethyl methacrylate methyl sulfate quaternary salt, dimethylaminoethyl acrylamide methyl sulfate quaternary salts, dimethylaminopropyl acrylamide methyl sulfate quaternary salts, dimethylaminopropyl methacrylamide methyl sulfate quaternary salts, diallyldimethyl ammonium chloride, N-vinyl formamide, dimethylamino ethyl methacrylate acid salts (including, but not limited to, sulfuric acid and hydrochloride acid salts), dimethylaminoethyl methacrylate methyl chloride quaternary salt, dimethylaminoethyl methacrylate benzyl chloride quaternary salt, methacrylamidopropyl trimethyl ammonium chloride, acrylamidopropyl trimethyl ammonium chloride, methylene bis acrylamide, diallylamine, acid salts of diallylamine, triallylamine, acid salts of triallylamine, ethylene glycol dimethacrylate, hydroxymethylacrylate, hydroxyethylacrylate, hydroxypropylacrylate, hydroxypropylmethacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethylacrylate, polyethylene glycol dimethacrylate, glycidyl methacrylate, acrylamidomethylpropane sulfonic acid and the sodium salt thereof, vinyl alcohol, vinyl acetate, or N-vinylpyrrolidone;
- and
- S is selected from sulfomethylacrylamide or sulfoethylacrylamide.
28 more elements
Dependencies are inferred from the claim text.