Tagging agents, anti-scalant polymer compositions, and methods

Patent metadata

Field	Value
Publication number	US-11897984-B2
Application number	US-202017755564-A
Country	US
Kind code	B2
Filing date	Dec 4, 2020
Priority date	Dec 5, 2019
Publication date	Feb 13, 2024
Grant date	Feb 13, 2024

Abstract

Tagging agents, including fluorescent monomers, which may be polymerized. Anti-scalant polymer compositions that include a copolymer of a tagging agent and an anti-scalant monomer. Methods for synthesizing tagging agents, anti-scalant polymer compositions, and detecting an anti-scalant polymer composition.

First claim

We claim:

1. A polymer composition comprising:
a copolymer comprising—
(i) a first monomer selected from the group consisting of (a) a compound of Formula (I), (b) a compound of Formula (II), (c) a compound or isomer of Formula (III), and (d) a compound or isomer of Formula (IV), wherein the first monomer is a tagging monomer, and
(ii) at least one second monomer comprising at least one polymerizable double bond or at least one polymerizable triple bond, wherein the at least one second monomer is a scale-inhibiting monomer;

wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 33 , R 34 , R 35 , R 36 , R 37 , R 38 , R 39 , R 40 , R 41 , R 42 , R 43 , and R 44 are independently selected from the group consisting of hydrogen, hydroxyl, C 1 -C 6 alkoxy, C 2 -C 6 alkenoxy, C 2 -C 6 alkynoxy, —N(R′)(R″), C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, and C 4 -C 14 aryl,
wherein R′ and R″ are independently selected from the group consisting of hydrogen and C 1 -C 6 alkyl,
wherein R 9 , R 10 , R 31 and R 32 are independently selected from the group consisting of hydrogen, hydroxyl, C 1 -C 6 alkyl, and C 1 -C 6 alkenyl,
wherein y is a single bond or a double bond, and
wherein z is a single bond or a double bond;
wherein the isomers of Formula (III) comprise a compound of Formula (Illi), a compound of Formula (IIIii), a compound of Formula (IIIiii), or a combination thereof —

and
wherein the isomers of Formula (IV) comprise a compound of Formula (IVi), a compound of Formula (IVii), a compound of Formula (IViii), or a combination thereof—

2. The polymer composition of claim 1 , wherein the first monomer is present in the copolymer at an amount of about 0.01% to about 5%, by weight, based on the weight of the copolymer.

3. The polymer composition of claim 1 , wherein (a) the first monomer comprises the compound of Formula (I), wherein:
(i) R 1 , R 2 , R 4 , R 5 , R 7 , R 8 , R 10 are hydrogen, R 3 and R 6 are hydroxyl, R 9 is an unsubstituted C 1 alkyl, y is a double bond, and the first monomer is 3′,6′-dihydroxy-3-methyl-5H-spiro[furan-2,9′-xanthen]-5-one, a salt, a hydrate, a salt hydrate, a stereoisomer, a dehydrate, a tautomer, or a derivative thereof —

or
(ii) R 1 , R 2 , R 4 , R 5 , R 7 , R 8 , R 9 , and R 10 are hydrogen, R 3 and R 6 are hydroxyl, y is a double bond, and the first monomer is 3′,6′-dihydroxy-5H-spiro[furan-2,9′-xanthen]-5-one, a salt, a hydrate, a salt hydrate, a stereoisomer, a dehydrate, a tautomer, or a derivative thereof—

or
(b) the first monomer is the compound of Formula (II), the compound or isomer of Formula (III), or the compound or isomer of Formula (IV), wherein:
(i) R 11 , R 12 , R 14 , R 15 , R 17 , and R 18 are hydrogen, R 13 and R 16 are hydroxyl, and the first monomer is 9-methylene-9H-xanthene-3,6-diol, a salt, a hydrate, a salt hydrate, a stereoisomer, a dehydrate, a tautomer, or a derivative thereof —

or
(ii) R 19 , R 20 , R 21 , R 23 , R 24 , R 25 , R 26 , R 28 , R 29 , and R 30 are hydrogen, R 22 and R 27 are hydroxyl, R 31 is an unsubstituted C 1 alkyl, z is a double bond, R 32 is hydrogen, and the first monomer is 3,11-dihydroxy-3′-methyl-5′H-spiro[dibenzo[c,h]xanthene-7,2′-furan]-5′-one, a salt, a hydrate, a salt hydrate, a stereoisomer, a dehydrate, a tautomer, or a derivative thereof—

or
(iii) R 33 , R 34 , R 35 , R 37 , R 38 , R 39 , R 40 , R 42 , R 43 , and R 44 , are hydrogen, R 36 and R 41 are hydroxyl, and the compound is 7-methylene-7H-dibenzo[c,h]xanthene-3,11-diol, a salt, a hydrate, a salt hydrate, a stereoisomer, a dehydrate, a tautomer, or a derivative thereof —

4. The polymer composition of claim 1 , wherein the first monomer is the compound of Formula (I) or the compound of Formula (II), wherein:
(i) R 1 , R 2 , R 4 , R 5 , R 7 , R 8 , R 10 are hydrogen, R 3 and R 6 are —N(R′)(R″), R′ and R″ are unsubstituted C 2 alkyl, R 9 is an unsubstituted C 1 alkyl, y is a double bond, and the first monomer is 3′,6′-bis(diethylamino)-3-methyl-5H-spiro[furan-2,9′-xanthen]-5-one, a salt, a hydrate, a salt hydrate, a stereoisomer, a dehydrate, a tautomer, or a derivative thereof—

or
(ii) R 11 , R 12 , R 14 , R 15 , and R 18 are hydrogen, R 13 and R 16 are —N(R′)(R″), R′ and R″ are unsubstituted C 2 alkyl, and the first monomer is N 3 , N 3 , N 6 , N 6 -tetraethyl-9-methylene-9H-xanthene-3,6-diamine, a salt, a hydrate, a salt hydrate, a stereoisomer, a dehydrate, a tautomer, or a derivative thereof:

or
(iii) R 1 , R 2 , R 4 , R 5 , R 7 , R 8 , R 9 , and R 10 are hydrogen, R 3 and R 6 are —N(R′)(R″), R′ and R″ are unsubstituted C 2 alkyl, y is a double bond, and the first monomer is 3′,6′-bis(diethylamino)-5H-spiro[furan-2,9′-xanthen]-5-one, a salt, a hydrate, a salt hydrate, a stereoisomer, a dehydrate, a tautomer, or a derivative thereof—

or
(iv) R 1 , R 2 , R 4 , R 5 , R 7 , R 8 are hydrogen, R 9 and R 10 are unsubstituted C 1 alkyl, R 3 and R 6 are —N(R′)(R″), R′ and R″ are unsubstituted C 2 alkyl, y is a double bond, and the first monomer is 3′,6′-bis(diethylamino)-3,4-dimethyl-5H-spiro[furan-2,9′-xanthen]-5-one, a salt, a hydrate, a salt hydrate, a stereoisomer, a dehydrate, a tautomer, or a derivative thereof—

or
(v) R 1 , R 2 , R 4 , R 5 , R 7 , R 8 , and R 10 are hydrogen, R 9 is an unsubstituted C 1 alkenyl, R 3 and R 6 are —N(R′)(R″), R′ and R″ are unsubstituted C 2 alkyl, y is a single bond, and the first monomer is 3′,6′-bis(diethylamino)-3-methylene-3,4-dihydro-5H-spiro[furan-2,9′-xanthen]-5-one, a salt, a hydrate, a salt hydrate, a stereoisomer, a dehydrate, a tautomer, or a derivative thereof—

5. The polymer composition of claim 1 , wherein the at least one second monomer comprises (i) sodium allyl sulfonate and at least one of maleic acid, maleic anhydride, or acrylic acid, or (ii) a compound of Formula (V):

wherein R 45 and R 46 are independently selected from the group consisting of hydrogen and C 1 -C 6 alkyl.

6. A method for preventing or reducing scale formation, the method c

Assignees

• Kemira Oyj

Inventors

• Nuutinen Vesa
• Metsälä Erkki Johannes
• Aksela Reijo
• Vuori Vesa
• Hesampour Mehrdad

Classifications

• C08F224/00 Primary

  Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a heterocyclic ring containing oxygen (cyclic esters of polyfunctional acids C08F218/00; cyclic anhydrides of unsaturated acids C08F220/00, C08F222/00) · CPC title

• C07D311/82

  Xanthenes · CPC title

• C07D493/10 Primary

  Spiro-condensed systems · CPC title

• C07D319/24

  [b,e]-condensed with two six-membered rings · CPC title

• C02F5/10

  using organic substances · CPC title