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US 6,645,428 B1Granted
Fluorescent monomers and tagged treatment polymers containing same for use in industrial water systems
AssigneeOndeo Nalco Company
InventorsJohn D. Morris, Barbara E. Moriarty, Mingli Wei, Patrick G. Murray, Jerry L. Reddinger
Life of this patent
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Abstract
Fluorescent monomers are described and claimed which are synthesized by reacting a substituted or non-substituted naphthalic 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.
Claims52
A fluorescent monomer selected from the group consisting of compounds of the formula:
- wherein R9 is selected from the group consisting of hydrogen, alkyl, alkoxy, halogen, sulfonic acid and its salts, phosphonic acid and its salts, dialkylamino, allyloxy and vinylbenzyloxy;
- R10 and R11 are alkyl;
- R12 is selected from the group consisting of allyl, 2-hydroxy-3-allyloxy-propyl, vinylbenzyl, 3-methacrylamidopropyl, 3-acrylamidopropyl, 2-acryloxyethyl and 2-methacryloxyethyl;
- A is selected from the group consisting of alkyl, alkoxyalkyl, alkylamidoalkyl, aryl or nonexistent;
- with the proviso that when A is nonexistent, 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 R10 or R11 is present;
- and X is an anionic counter ion.
4 more elements
A tagged treatment polymer selected from the group consisting of:
- GaQjWt (1)
- wherein G is selected from the group consisting of:
- wherein R9 is selected from the group consisting of hydrogen, alkyl, alkoxy, halogen, sulfonic acid and its salts, phosphonic acid and its salts, dialkylamino, allyloxy and vinylbenzyloxy;
- R10 and R11 are alkyl;
- R12 is selected from the group consisting of allyl, 2-hydroxy-3-allyloxy-propyl, vinylbenzyl, 3-methacrylamidopropyl, 3-acrylamidopropyl, 2-acryloxyethyl and 2-methacryloxyethyl;
- A is selected from the group consisting of alkyl, alkoxyalkyl, alkylamidoalkyl, aryl or nonexistent;
- with the proviso that when A is nonexistent, 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 R10 or R11 is present;
- and
- X is an anionic counter ion;
- wherein Q is selected from the group consisting of acrylic acid and salts thereof, methacrylic acid and salts thereof, maleic acid and salts thereof, maleic anhydride, acrylamide, crotonic acid, acrylamidomethylpropane sulfonic acid and salts thereof;
- wherein W is selected from the group consisting of:
- 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, dimethylamninopropy 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, triallylamine, acid salts of trial lylamine, 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, and N-vinylpyrrolidone;
- with the proviso that Q and W cannot both be the same;
- wherein a is from about 0.001 to about 10.0 mole percent;
- wherein j is from about 0 to about 99.999 mole percent;
- wherein t is from about 0 to about 99.999 mole percent;
- and
- wherein a+j+t=100;
- GaQvWfSc (2)
- wherein G is as previously defined;
- wherein Q is as previously defined;
- wherein W is as previously defined, with the proviso that Q and W cannot both be the same;
- wherein S is selected from the group consisting of sulfomethylacrylamide and sulfoethylacrylamide;
- wherein a is from about 0.001 to about 10.00 mole percent;
- wherein v is from about 0 to about 97.999 mole percent;
- wherein f is from about 1 to about 97.999 mole percent;
- wherein c is from about 1 to about 40 mole percent;
- and
- wherein a+v+f+c=100.
27 more elements
A process for the inhibition of scale formation in an industrial water system which comprises introducing into said industrial water system a tagged treatment polymer selected from the group consisting of:
- GaQjWt (1)
- wherein G is selected from the group consisting of:
- wherein R9 is selected from the group consisting of hydrogen, alkyl, alkoxy, halogen, sulfonic acid and its salts, phosphonic acid and its salts, dialkylamino, allyloxy and vinylbenzyloxy;
- R10 and R11 are alkyl;
- R12 is selected from the group consisting of allyl, 2-hydroxy-3-allyloxy-propyl, vinylbenzyl, 3-methacrylamidopropyl, 3-acrylamidopropyl, 2-acryloxyethyl and 2-methacryloxyethyl;
- A is selected from the group consisting of alkyl, alkoxyalkyl, alkylamidoalkyl, aryl or nonexistent;
- with the proviso that when A is nonexistent, 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 R10 or R11 is present;
- and
- X is an anionic counter ion;
- wherein Q is selected from the group consisting of acrylic acid and salts thereof, methacrylic acid and salts thereof, maleic acid and salts thereof, maleic anhydride, acrylamide, crotonic acid, acrylamidomethylpropane sulfonic acid and salts thereof;
- wherein W is selected from the group consisting of:
- 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, 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, and N-vinylpyrrolidone;
- with the proviso that Q and W cannot both be the same;
- wherein a is from about 0.001 to about 10.0 mole percent;
- wherein j is from about 0 to about 99.999 mole percent;
- wherein t is from about 0 to about 99.999 mole percent;
- and
- wherein a+j+t=100;
- GaQvWfSc (2)
- wherein G is as previously defined;
- wherein Q is as previously defined;
- wherein W is as previously defined, with the proviso that Q and W cannot both be the same;
- wherein S is selected from the group consisting of sulfomethylacrylamide and sulfoethylacrylamide;
- wherein a is from about 0.001 to about 10.00 mole percent;
- wherein v is from about 0 to about 97.999 mole percent;
- wherein f is from about 1 to about 97.999 mole percent;
- wherein c is from about 1 to about 40 mole percent;
- and
- wherein a+v+f+c=100;
- in an amount sufficient to inhibit scale formation.
28 more elements
A method for maintaining the desired amount of tagged treatment polymer in an industrial water system comprising the steps of:
- i) adding to said industrial water system a tagged treatment polymer, selected from a group consisting of:
- GaQjWt (1)
- wherein G is selected from the group consisting of:
- wherein R9 is selected from the group consisting of hydrogen, alkyl, alkoxy, halogen, sulfonic acid and its salts, phosphonic acid and its salts, dialkylamino, allyloxy and vinylbenzyloxy;
- R10 and R11 are alkyl;
- R12 is selected from the group consisting of allyl, 2-hydroxy-3-allyloxy-propyl, vinylbenzyl, 3-methacrylamidopropyl, 3-acrylamidopropyl, 2-acryloxyethyl and 2-methacryloxyethyl;
- A is selected from the group consisting of alkyl, alkoxyalkyl, alkylamidoalkyl,
- aryl or nonexistent;
- with the proviso that when A is nonexistent, 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 R10 or R11 is present;
- and
- X is an anionic counter ion;
- wherein Q is selected from the group consisting of acrylic acid and salts thereof, methacrylic acid and salts thereof, maleic acid and salts thereof, maleic anhydride, acrylamide, crotonic acid, acrylamidomethylpropane sulfonic acid and salts thereof;
- wherein W is selected from the group consisting of:
- 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, 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, and N-vinylpyrrolidone;
- with the proviso that Q and W cannot both be the same;
- wherein a is from about 0.001 to about 10.0 mole percent;
- wherein j is from about 0 to about 99.999 mole percent;
- wherein t is from about 0 to about 99.999 mole percent;
- and
- wherein a+j+t=100;
- GaQvWfSc (2)
- wherein G is as previously defined;
- wherein Q is as previously defined;
- wherein W is as previously defined, with the proviso that Q and W cannot both be the same;
- wherein S is selected from the group consisting of sulfomethylacrylamide and sulfoethylacrylamide;
- wherein a is from about 0.001 to about 10.00 mole percent;
- wherein v is from about 0 to about 97.999 mole percent;
- wherein f is from about 1 to about 97.999 mole percent;
- wherein c is from about 1 to about 40 mole percent;
- and
- wherein a+v+f+c=100;
- i) using a fluorometer to detect the fluorescent signal of said tagged treatment polymer;
- ii) converting the fluorescent signal of said tagged treatment polymer to the concentration of said tagged treatment polymer;
- and
- iii) adjusting the concentration of said tagged treatment polymer according to what the desired concentration is for said tagged treatment polymer in said industrial water system.
34 more elements
A method for maintaining the desired amount of tagged treatment polymer in an industrial water system comprising the steps of:
- a) adding an inert tracer and a tagged treatment polymer to the water of an industrial water system, wherein said tagged treatment polymer is selected from the group consisting of:
- GaQjWt (1)
- wherein G is selected from the group consisting of:
- wherein R9 is selected from the group consisting of hydrogen, alkyl, alkoxy, halogen, sulfonic acid and its salts, phosphonic acid and its salts, dialkylamino, allyloxy and vinylbenzyloxy;
- R10 and R11 are alkyl;
- R12 is selected from the group consisting of allyl, 2-hydroxy-3-allyloxy-propyl, vinylbenzyl, 3-methacrylamidopropyl, 3-acrylamidopropyl, 2-acryloxyethyl and 2-methacryloxyethyl;
- A is selected from the group consisting of alkyl, alkoxyalkyl, alkylamidoalkyl, aryl or nonexistent;
- with the proviso that when A is nonexistent, 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 R10 or R11 is present;
- and
- X is an anionic counter ion;
- wherein Q is selected from the group consisting of acrylic acid and salts thereof, methacrylic acid and salts thereof, maleic acid and salts thereof, maleic anhydride, acrylamide, crotonic acid, acrylamidomethylpropane sulfonic acid and salts thereof;
- wherein W is selected from the group consisting of:
- 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, 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, and N-vinylpyrrolidone;
- with the proviso that Q and W cannot both be the same;
- wherein a is from about 0.001 to about 10.0 mole percent;
- wherein j is from about 0 to about 99.999 mole percent;
- wherein t is from about 0 to about 99.999 mole percent;
- and
- wherein a+j+t=100;
- GaQvWfSc (2)
- wherein G is as previously defined;
- wherein Q is as previously defined;
- wherein W is as previously defined, with the proviso that Q and W cannot both be the same;
- wherein S is selected from the group consisting of sulfomethylacrylamide and sulfoethylacrylamide;
- wherein a is from about 0.001 to about 10.00 mole percent;
- wherein v is from about 0 to about 97.999 mole percent;
- wherein f is from about 1 to about 97.999 mole percent;
- wherein c is from about 1 to about 40 mole percent;
- and
- wherein a+v+f+c=100;
- such that a desired concentration of said tagged treatment polymer is present in said water;
- b) using a fluorometer to detect the fluorescent signals of said inert tracer and said tagged treatment polymer;
- c) converting the fluorescent signals of said inert tracer and said tagged treatment polymer to the concentration of said inert tracer and said tagged treatment polymer;
- and
- d) adjusting the concentration of said tagged treatment polymer according to what the desired concentration is for said tagged treatment polymer in said industrial water system.
33 more elements
Dependencies are inferred from the claim text.