Fluorescent monomers and tagged treatment polymers containing same for use in industrial water systems

Patent metadata

Field	Value
Publication number	US-10323112-B2
Application number	US-201715602349-A
Country	US
Kind code	B2
Filing date	May 23, 2017
Priority date	Dec 28, 2012
Publication date	Jun 18, 2019
Grant date	Jun 18, 2019

Abstract

The present disclosure relates to 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.

First claim

What is claimed is:

1. A tagged treatment polymer, the polymer comprising a chain of chemically bonded monomeric units, at least some of the monomeric units selected from the group consisting of G a Q j W t , G a Q v W f S c , and any combination thereof; wherein:
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 G a Q v W f S c 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 G a Q j W t 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 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 NO 2 , CO 2 H and its salts, PO 3 H 2 and it salts, SO 3 H and its salts, SO 2 NH 2 or SO 2 NR 1 R 2 ;
Z is one of the following: CH 2 , C═O, CR 1 R 2 , NH, NR 1 , NH 2 + , NR 1 R 2 + , NOH, O, S, SO, or SO 2 ;
R 3 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 R 1 or R 2 is present;
X is an anionic counter ion; and

in Formula II, each Y is selected from NO 2 , CO 2 H and its salts, PO 3 H 2 and it salts, SO 3 H and its salts, SO 2 NH 2 or SO 2 NR 1 R 2 ;
Z is selected from CH 2 , C═O, CR 2 , NH, NR 1 , NH 2 + , NR 1 R 2 + , NOH, O, S, SO, or SO 2 ;
A is absent or selected from alkyl, alkyloxyalkyl, alkoxy, alkylamidoalkyl, alkylamino, NH, or aryl;
R 4 is selected from allyl, acryl, methacryl, 2-hydroxy-3-allyloxy-propyl, vinyl benzyl, 2-acryloxyethyl or 2-methacryloxyethyl;

R 1 and R 2 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, or acrylamidomethylpropane sulfonic acid and 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-i sopropylacrylamide, 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 the group consisting of sulfomethylacrylamide and sulfoethylacrylamide.

2. The polymer of claim 1 , wherein G is selected from the group consisting of sulfonated-N-(3-N′, N′-Dimethylaminopropyl) benzo (k,l) xanthene-3,4-dicarboxylic imide, 2-hydroxy-3-allyloxypropyl quaternary salt and sulfonated-N-(3-N′, N′-Dimethylaminopropyl) benzo (k,l) xanthene-3,4-dicarboxylic imide, vinyl benzyl chloride quaternary salt, Q is acrylic acid, W is acrylamide and S is N sulfomethylacrylamide.

3. The polymer of claim 1 , wherein G is selected from the group consisting of sulfonated-N-(3-N′, N′-Dimethylaminopropyl) benzo (k,l) xanthene-3,4-dicarboxylic imide, 3-methacrylamidopropyl quaternary salt and sulfonated-N-(3-N′, N′-Dimethylaminopropyl) benzo (k,l) xanthene-3,4-dicarboxylic imide, allyl chloride quaternary salt, Q is acrylic acid, W is acrylamide and S is N-sulfomethylacrylamide.

4. The polymer of claim 1 , wherein G is sulfonated-N-(3-N′, N′-Dimethylaminoethyl) benzo (k,l) xanthene-3,4-dicarboxylic imide, 3-methacrylamidopropyl quaternary salt, Q is acrylic acid, W is acrylamide and S is N-sulfomethylacrylamide.

5. The polymer of claim 1 , wherein G is selected from the group consisting of sulfonated-N-(3-N′, N′-Dimethylaminopropyl) benzo (k,l) xanthene-3,4-dicarboxylic imide, 3-methacrylamidopropyl quaternary salt and sulfonated-N-(3-N′, N′-Dimethylaminoethyl) benzo (k,l) xanthene-3,4-dicarboxylic imide, 3-methacrylamidopropyl quaternary salt, Q is acrylic acid, W is acrylamidomethylpropane sulfonic acid.

6. The polymer of claim 1 , wherein G is selected from the group consisting of sulfonated-N-(3-N′, N′-Dimethylaminopropyl) benzo (k,l) xanthene-3,4-dicarboxylic imide, 2-hydroxy-3-allyloxypropyl quaternary salt and sulfonated-N-(3-N′, N′-Dimethylaminopropyl) benzo (k,l) xanthene-3,4-dicarboxylic imide, vinyl benzyl chloride quaternary salt, Q is acrylic acid, W is acrylamidomethylpropane sulfonic acid.

7. The polymer of claim 1 , wherein G is sulfonated-N-(3-N′, N′-Dimethylaminopropyl) benzo (k,l) xanthene-3,4-dicarboxylic imide, allyl chloride quaternary salt, Q is acrylic acid, and W is acrylamidomethylpropane sulfonic acid.

8. The polymer of claim 1 , wherein G is sulfonated-N-(3-N′, N′-Dimethylaminopropyl) benzo (k,l) xanthene-3,4-dicarboxylic imide, vinylbenzyl chloride quaternary salt and Q is acrylic acid.

9. The polymer of claim 1 , wherein G is selected from the group consisting of sulfonated-N-(3-N′, N′-Dimethylaminopropyl) benzo (k,l) xanthene-3,4-dicarboxylic imide, allyl chloride quaternary salt and sulfonated-N-(3-N′, N′-Dimethylaminopropyl) benzo (k,l) xanthene-3,4-dicarboxylic imide, 2-hydroxy-3-allyloxypropyl quaternary salt, and Q is acrylic acid.

10. The polymer of claim 1 , wherein G is selected from the group consisting of sulfonated-N-(3-N′, N′-Dimethylaminopropyl) benzo (k,l) xanthene-3,4-dicarboxylic imide, 3-methacrylamidopropyl quaternary salt and sulfonated-N-(3-N′, N′-Dimethylaminoethyl) benzo (k,l) xanthene-3,4-dicarboxylic imide, 3-methacrylamidopropyl quaternary salt, and Q is acrylic acid.

11. The polymer of claim 1 , wherein t is from about 0.001 to about 99.998%.

12. The polymer of claim 1 , wherein Q is acrylic acid and W is acrylamide or acrylamidomethylpropane sulfonic acid.

13. The polymer of claim 1 , wherein Q is acrylamide, W is acrylic acid, and S is N-sulfomethylacrylamide.

14. A

Assignees

• Ecolab Usa Inc

Inventors

• Atkins Jeffery M
• Moriarty Barbara E
• Zinn Paul J

Classifications

• C09B69/109

  containing other specific dyes · CPC title

• C09B57/08

  Naphthalimide dyes; Phthalimide dyes · CPC title

• C02F2103/32

  from the food or foodstuff industry, e.g. brewery waste waters · CPC title

• C02F2103/28

  from the paper or cellulose industry · CPC title

• C02F2103/16

  from metallurgical processes, i.e. from the production, refining or treatment of metals, e.g. galvanic wastes · CPC title