Use of fluorescent polymers in marking compositions for the diagnostic determination of cleaning performance

Patent metadata

Field	Value
Publication number	US-11344646-B2
Application number	US-202117220230-A
Country	US
Kind code	B2
Filing date	Apr 1, 2021
Priority date	Jul 1, 2014
Publication date	May 31, 2022
Grant date	May 31, 2022

Abstract

The present invention generally relates to fluorescent marking compositions and their use to determine whether a surface has been cleaned. More particularly, the marking compositions comprise fluorescent polymers.

First claim

What is claimed is:

1. A fluorescent marking composition comprising:
a water-dispersible fluorescent polymer derived from polymerization of one or more polymerizable fluorescent monomer units and one, two, or three polymerizable non-fluorescent monomer units; and having a weight average molecular weight of 2 to 2000 kDa, light absorption spectrum in the range of about 310 to about 400 nm, light emission spectrum in the range of about 400 to about 750 nm upon exposure to UV radiation, and 0.001 to about 10 mole percent of the fluorescent monomer.

2. The composition of claim 1 , wherein the polymer is a random polymer.

3. The composition of claim 1 , wherein at least one non-fluorescent monomer is selected from the group of acrylic acid, acrylamide, or 2-acrylamido-2-methylpropane sulfonic acid.

4. The composition of claim 1 , further comprising a solvent and a thickener.

5. The composition of claim 4 , wherein the composition has a viscosity of about 10 to about 6,000 cps when measured with a Brookfield LVT viscometer at 25° C. with a #1 spindle at 60 rpm.

6. The composition of claim 4 , wherein the thickener is selected from the group of xanthan gum, guar gum, modified guar, a polysaccharide, pullulan, an alginate, a modified starch, a cellulose, a polyacrylate, a vinyl acetate/alcohol copolymer, casein, a urethane copolymer, dimethicone PEG-8 polyacrylate, poly(DL-lactic-co-glycolic acid), a polyethylene glycol, a polypropylene glycol, pectin, or a combination thereof.

7. The composition of claim 4 , comprising about 0.01 to about 2 wt. % of thickener.

8. The composition of claim 4 , wherein the solvent is selected from the group of water and an organic solvent.

9. The composition of claim 4 , comprising about 40 to about 99 wt. % solvent.

10. The composition of claim 1 , further comprising a surfactant.

11. The composition of claim 10 , comprising about 0.01 to about 10 wt. % surfactant.

12. The composition of claim 1 , further comprising a preservative, a pH adjusting agent, or a combination thereof.

13. The composition of claim 1 , wherein the fluorescent monomer is selected from the group of

wherein:
n is an integer from 1 to 10;
A is alkyl, alkoxyalkyl, alkylamidoalkyl, aryl, or is absent; with the proviso that when A is absent, E is nitrogen and E is bonded directly to the imide nitrogen;
B is sulfur or nitrogen with the proviso that when B is sulfur, only one of R 10 or R 11 is present;
D is oxygen, nitrogen, sulfur or is absent, with the proviso that when D is absent, (CH 2 ) n is bonded directly to a carbon on the ring;
R 3 and R 4 are each independently sulfonic acid or a salt thereof, carboxylic acid or a salt thereof, allyloxy or vinylbenzyloxy, with the proviso that when one of R 3 or R 4 is sulfonic acid or a salt thereof or carboxylic acid or a salt thereof, the other must be allyloxy or vinylbenzyloxy;
R 5 is alkyl, alkylamino, hydroxyalkyl or allyl;
R 6 and R 7 are each independently alkyl;
R 8 is allyl, alkyl, vinylbenzyl or 2-hydroxy-3-allyloxypropyl;
R 9 is hydrogen, alkyl, alkoxy, halogen, sulfonic acid or a salt thereof, phosphonic acid or a salt thereof, dialkylamino, allyloxy or vinylbenzyloxy;
R 10 and R 11 are each independently alkyl;
R 12 is allyl, 2-hydroxy-3-allyloxypropyl, vinylbenzyl, 3-methacrylamidopropyl, 3-acrylamidopropyl, 2-acryloxyethyl or 2-methacryloxyethyl; and
X − is an anion;

wherein:
A is alkyl, alkoxyalkyl, alkylamidoalkyl, aryl, or is absent; with the proviso that when A is absent, E is nitrogen and E is bonded directly to the imide nitrogen;
E is sulfur or nitrogen with the proviso that when E is sulfur, only one of R 1 or R 2 is present;
D is alkyl, alkoxyalkyl, alkoxy, alkylamidoalkyl, alkylamino, NH, aryl or is absent;
R is independently hydrogen or alkyl;
R 1 and R 2 are each independently alkyl;
R 3 is allyl, 2-hydroxy-3-allyoxypropyl, vinyl benzyl, 3-methacrylamidopropyl, 3-acrylamidopropyl, 2-acryloxyethyl or 2-methacryloxyethyl;
R 4 is allyl, acryl, methacryl, 2-hydroxy-3-allyloxypropyl, vinyl benzyl, 2-acryloxyethyl and 2-methacryloxyethyl;
each R 5 is independently hydrogen, halogen, —NO 2 , —C(O)OH or a salt thereof, —PO(OH) 2 or a salt thereof, —SO 2 (OH) or a salt thereof, or —SO 2 (NR 2 );
X − is an anion; and
Z is —CH 2 —, —C(O)—, —CR 2 —, —NR—, —NR 2 + —, —N(OH)—, —O—, —S—, —S(O)—, or —SO 2 —;

wherein:
M is hydrogen, sodium, potassium, cesium, rubidium, lithium or ammonium; and n is an integer 1, 2, 3, 4, 6, or 9; and
combinations thereof.

14. A fluorescent marking composition comprising:
a water-dispersible fluorescent polymer comprising a non-fluorescent polymer with a fluorescent dye covalently bonded the polymer by an ester, amide, or ether linkage, the polymer having a weight average molecular weight of 2 to 2000 kDa, light absorption spectrum in the range of about 310 to about 400 nm, and light emission spectrum in the range of about 400 to about 750 nm upon exposure to UV radiation.

15. The composition of claim 14 , wherein the non-fluorescent monomer is selected from the group of acrylic acid, acrylamide, or 2-acrylamido-2-methylpropane sulfonic acid.

16. The composition of claim 14 , further comprising a solvent and a thickener.

17. The composition of claim 16 , wherein the composition has a viscosity of about 10 to about 6,000 cps when measured with a Brookfield LVT viscometer at 25° C. with a #1 spindle at 60 rpm.

18. The composition of claim 16 , wherein the thickener is selected from the group of xanthan gum, guar gum, modified guar, a polysaccharide, pullulan, an alginate, a modified starch, a cellulose, a polyacrylate, a vinyl acetate/alcohol copolymer, casein, a urethane copolymer, dimethicone PEG-8 polyacrylate, poly(DL-lactic-co-glycolic acid), a polyethylene glycol, a polypropylene glycol, pectin, or a combination thereof.

19. The composition of claim 16 , comprising about 0.01 to about 2 wt. % of thickener.

20. The composition of claim 16 , wherein the solvent is selected from the group of water and an organic solvent.

21. The composition of claim 16 , comprising about 40 to about 99 wt. % solvent.

22. The composition of claim 14 , further comprising a surfactant.

23. The composition of claim 22 , comprising about 0.01 to about 10 wt. % surfactant.

24. The composition of claim 14 , further comprising a preservative, a pH adjusting agent, or a combination thereof.

Assignees

• Ecolab Usa Inc

Inventors

• Wegner Joseph
• Brown Erin
• Atkins Jeffery
• Zinn Paul
• Walicki Robert
• Hu Lanhua

Classifications

• C09K11/025 Primary

  non-luminescent particle coatings or suspension media · CPC title

• C09K2211/1466

  containing nitrogen as the only heteroatom · CPC title

• C08F220/06

  Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof · CPC title

• A61L2/18

  Liquid substances · CPC title

• C09B69/10

  Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds · CPC title