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

• US 10,155,058 B2
• Filed: 12/01/2017
• Issued: 12/18/2018
• Est. Priority Date: 07/01/2014
• Status: Active Grant

• Current Assignee: Ecolab USA Incorporated (Ecolab, Inc.)
• Original Assignee: Ecolab USA Incorporated (Ecolab, Inc.)
• Inventors: Wegner, Joseph, Brown, Erin, Atkins, Jeffery, Zinn, Paul, Walicki, Robert, Hu, Lanhua
• Primary Examiner(s): Porta, David
• Assistant Examiner(s): BOOSALIS, FANI POLYZOS
• Application Number:
  US15/829,006
• Publication Number:
  US 20180085483A1
• Time in Patent Office: 382 Days
• CPC Class Codes: A61L 2/18 Liquid substances or solutions comprising solids or dissolved gases
• CPC Class Codes: A61L 2/28 Devices for testing the effectiveness or completeness of sterilisation, e.g. indicators which change colour apparatus involving enzymes or microorganisms C12M1/34; methods involving enzymes or microorganisms C12Q1/00
• CPC Class Codes: C08F 220/06 Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
• CPC Class Codes: C09B 69/10 Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds addition products of alkylene oxide to dyes, C09B69/00; dyeing with polymeric dyes D06P1/0056
• CPC Class Codes: C09K 11/025 non-luminescent particle coatings or suspension media
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1416 Condensed systems
• CPC Class Codes: C09K 2211/1433 bridged by heteroatoms, e.g. N, P, Si or B
• CPC Class Codes: C09K 2211/1466 containing nitrogen as the only heteroatom
• CPC Class Codes: G01N 31/226 for investigating the degree of sterilisation

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.

Claims

1. A method for evaluating cleaning of a surface, the method comprising:

applying an amount of indicator material to the surface within a space, the indicator material comprising a water-dispersible fluorescent polymer from polymerization of one or more polymerizable fluorescent monomer units and one or more polymerizable non-fluorescent monomer units and having a weight average molecular weight of 2 to 2000 kDa;

allowing for the surface to be cleaned; and

determining if any of the indicator material remains on the surface by exposing the surface to UV radiation.

2. The method of claim 1, wherein the surface is a surface of a High Touch Object (HTO).

3. The method of claim 2, wherein the HTO is selected from the group consisting of a toilet handle, a toilet set, a bedpan flushing device, a faucet handle, a doorknob, a door handle, a push plat, a grab plate, a toilet area grab bar, a telephone receiver, a call button, a table, a chair seat, a chair arm, a bedrail, a drape, a room light switch, a computer mouse, a keyboard wrist rest, and a soap dispenser.

4. The method of claim 1, wherein the surface is a surface in a hospital, a nursing home, long-term care facility, clinic, doctor'"'"'s office, or dental office.

5. The method of claim 1, wherein the surface is a surface in a restaurant, bar, nightclub, grocery store, hotel, bank, spa, health club, fitness center, locker room, day care center, indoor playground, school, convention center, office building, public restroom, movie theater, place of worship, public transit vehicle, airplane, taxicab, cruise ship, or ferry.

6. The method of claim 1, wherein the indicator material is applied with an applicator comprising a spray applicator, a foam pad applicator, a felt tip applicator, a brush, a roll, a wipe, or a solid form.

7. The method of claim 1, wherein the indicator material is applied with an applicator comprising a bottle or ampule.

8. The method of claim 1 further comprising recording a result of the evaluation and tracking cleaning outcomes.

9. The method of claim 8, wherein the recording is done using a mobile application.

10. The method of claim 8, wherein the result is stored as data.

11. The method of claim 10, wherein the data is wirelessly transmitted.

12. The method of claim 10, wherein the data is aggregated and analyzed.

13. The method of claim 10 further comprising using the data to assess whether cleaning activities are consistent with nosocomial infection control efforts.

14. The method of claim 10 further comprising preparing a report on the data.

15. The method of claim 14, wherein the report comprises a percentage of High Touch Objects (HTOs) cleaned, a comparison against baseline data, an identification of areas for improvement, or a combination thereof.

16. The method of claim 1, wherein the polymerizable fluorescent monomer unit has structure (I), (II) or (III):

17. The method of claim 16, wherein

the polymerizable fluorescent monomer unit has the structure (I) and is 4-methoxy-N-(3-N′

, N′

-dimethylamino-propyl)naphthalimide vinyl benzyl chloride quaternary salt, or 4-methoxy-N -(3-N′

,N′

-dimethylaminopropyl)naphthalimide 2-hydroxy-3-allyloxypropyl chloride quaternary salt;

4-methoxy-N-(3-N′

,N′

-dimethylaminopropyl)naphthalimide allyl chloride quaternary salt;

the polymerizable fluorescent monomer unit has the structure (II) and is N-allyl-4-(2-N′

,N′

-dimethylamino-ethoxy)naphthalimide methyl sulfate quaternary salt;

or

the polymerizable fluorescent monomer unit has the structure (III) and is 5-allyloxy-4′

-carboxy -1,8-naphthoylene-1′

,2′

-benzimidazole or 6-vinylbenzyloxy-4′

-carboxy-1,8-naphthoylene-1′

,2′

-benzimidazole.

18. The method of claim 16, wherein the polymer is a random polymer of a fluorescent monomer unit and polymerizable monomer units (Q), (W), and optionally (S), wherein the polymer has a formula G_aQ_jW_t, G_aQ_vW_f S_c, or a combination thereof, wherein:

G is the polymerizable fluorescent monomer unit;

Q is acrylic acid or a salt thereof, methacrylic acid or a salt thereof, maleic acid or a salt thereof, crotonic acid or a salt thereof, maleic anhydride, acrylamide, or acrylamidomethylpropane sulfonic acid or a salt thereof;

S is N-sulfomethacrylamide or N-sulfoethylacrylamide;

W is acrylic acid or a salt thereof, methacrylic acid or a salt thereof, itaconic acid or a salt thereof, maleic acid or a salt thereof, maleic anhydride, crotonic acid or a salt thereof, acrylamide, methacrylamide, vinyl sulfonic acid, styrene sulfonate, N-tert-butylacrylamide, N-isopropylacrylamide, N-butoxymethylacrylamide, N,N-dimethylacrylamide, N,N-diethylacrylamide, dimethylaminoethyl acrylate methyl chloride quaternary salt, dimethylaminoethyl acrylate benzyl chloride quaternary salt, dimethylaminoethyl acrylate methyl sulfate quaternary salt, dimethylaminoethyl methacrylate methyl sulfate quaternary salt, dimethylaminoethyl acrylamide methyl sulfate quaternary salt, dimethylaminopropyl acrylamide methyl sulfate quaternary salt, dimethylaminopropyl methacrylamide methyl sulfate quaternary salt, diallyldimethylammonium chloride, N-vinylformamide, a dimethylaminoethyl methacrylate acid salt, dimethylaminoethyl methacrylate methyl chloride quaternary salt, dimethylaminoethyl methacrylate benzyl chloride quaternary salt, methacrylamidopropyl trimethylammonium chloride, acrylamidopropyl trimethylammonium chloride, N,N′

-methylene bisacrylamide, triallylamine, an acid salt of triallylamine, ethylene glycol dimethacrylate, 2-(hydroxymethyl)acrylic acid, 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, polyethylene glycol dimethacrylate, glycidyl methacrylate, 2-acrylamido2-methylpropane sulfonic acid or a salt thereof, vinyl alcohol, vinyl acetate, or N-vinylpyrrolidone, with the proviso that Q and W cannot both be the same;

a is from about 0.001 to about 10 mole percent;

c is from about 1 to about 40 mole percent;

f is from about 1 to about 97.999 mole percent;

j is from 0 to about 99.999 mole percent;

t is from 0 to about 99.999 mole percent;

v is from 0 to about 97.999 mole percent;

the sum of a, j and t equals 100 mole percent; and

the sum of a, v, f and c equals 100 mole percent.

19. The method of claim 17, wherein the polymer has the formula G_aQ_jW_t or G_aQ_vW_fS_c and wherein Q is acrylic acid;

the polymer has the formula G_aQ_jW_t and wherein Q is acrylic acid and W is acrylamide;

the polymer has the formula G_aQ_jW_t and wherein Q is acrylic acid and W is 2-acrylamido-2-methylpropane sulfonic acid;

or the polymer has the formula the G_aQ_vW_fS_c and wherein Q is acrylic acid, W is acrylamide, and S is N-sulfomethylacrylamide.

20. The method of claim 1, wherein the polymerizable fluorescent monomer unit has structure (IV) or (V):

21. The method of claim 20, wherein

the polymerizable fluorescent monomer unit has the structure (IV) and is sulfonated-N-(3-N′

,N′

-dimethylaminopropyl)benzo (k,l) xanthene-3,4-dicarboxylic imide 2-hydroxy-3-allyloxypropyl quaternary salt, sulfonated-N-(3-N′

,N′

-dimethylaminopropyl)benzo (k,l) xanthene-3,4-dicarboxylic imide vinyl benzyl chloride quaternary salt, or sulfonated-N-(3-N′

,N′

-dimethylaminopropyl)benzo (k,l) xanthene-3,4-dicarboxylic imide allyl chloride quaternary salt;

or

the polymerizable fluorescent monomer unit has structure (V) and is N-(3-N′

,N′

-dimethylaminopropyl)benzo (k,l) xanthene-3,4-dicarboxylic imide allyl chloride quaternary salt.

22. The method of claim 1, wherein the polymerizable fluorescent monomer unit has structure (VI) or (VII):

23. The method of claim 1, wherein the polymerizable fluorescent polymer has been derived from polymerization of acrylic acid, 2-acrylamido-2-methylpropane sulfonic acid, and 4-methoxy-N-(3-N′

,N′

-dimethylaminopropyl)-naphthalimide 2-hydroxy-3-allyloxypropyl quaternary salt.

24. The method of claim 1, wherein the polymerizable fluorescent monomer unit has structure (VIII) or (IX):

25. The method of claim 24, wherein

the polymerizable fluorescent monomer unit having structure (VIII) 8-(allyloxy)-1,3,6-pyrene trisulfonic acid or a sodium, potassium, cesium, rubidium, lithium or ammonium salt thereof;

or

the polymerizable fluorescent monomer unit having structure (IX) is 8-(3-vinylbenzyloxy)-1,3,6-pyrene trisulfonic acid, 8-(4-vinylbenzyloxy)-1,3,6-pyrene trisulfonic acid, or a sodium, potassium, cesium, rubidium, lithium or ammonium salt thereof.

26. The method of claim 24, wherein the polymer is a random polymer of a polymerizable fluorescent monomer unit (G) and polymerizable monomer units (B), (C), and (D), wherein the polymer has a formula G_xB_y, G_xB_jC_k, G_xB_mD_q, G_xB_rC_sD_t, or a combination thereof wherein:

B is an acrylic acid or a salt thereof, methacrylic acid or a salt thereof, maleic acid or a

salt thereof, maleic anhydride, acrylamide, crotonic acid or a salt thereof, or a combination thereof;

C is methacrylic acid or a salt thereof, maleic acid or a salt thereof, maleic anhydride, crotonic acid or a salt thereof, itaconic acid or a salt thereof, acrylamide, methacrylamide, 2-acrylamido-2-methylpropanesulfonic acid or a salt thereof, polyethylene glycol monomethacrylate, vinyl phosphonic acid or a salt thereof, styrene sulfonic acid or a salt thereof, vinyl sulfonic acid or a salt thereof, 3-allyloxy-2-hydroxypropane sulfonic acid or a salt thereof, N-alkyl (meth)acrylamide, t-butyl (meth)acrylate, N-alkyl (meth)acrylate, N-alkanol-Nalkyl(meth)acrylate, vinyl acetate, 2-hydroxy N-alkyl(meth)acrylate, alkyl vinyl ether, alkoxyethyl acrylate, N-alkanol (meth)acrylamide, N,N-dialkyl(meth)acrylamide, 1-vinyl-2-pyrrolidinone, or a combination thereof;

D is sulfomethylacrylamide or sulfoethylacrylamide;

G is the fluorescent monomer unit;

j is from about 1 to about 98 mol %;

k is from about 1.999 to about 98 mol %;

m is from about 1 to about 95 mol %;

q is from about 4.999 to about 40 mol %;

r is from about 1 to about 89.999 mol %;

s is from about 1 to about 89.999 mol %;

t is from about 5 to about 40 mol %;

x is from about 0.001 to about 1 mol %;

y is from about 99.000 to about 99.999 mol %;

the sum of x and y equals 100 mol %;

the sum of x, j and k equals 100 mol %;

the sum of x, m and q equals 100 mol %; and

the sum of x, r, s and t equals 100 mol %.

27. The method of claim 26, wherein

the polymer has the formula G_xB_y wherein B is acrylic acid or a salt thereof;

the polymer has the formula G_xB_jC_k wherein B is acrylic acid or a salt thereof, and C is acrylamide;

the polymer has the formula G_xB_mD_q wherein B is acrylic acid or a salt thereof, and D is sulfomethylacrylamide;

or

the polymer has the formula G_xB_rC_sD_t wherein B is acrylic acid or a salt thereof, C is acrylamide, and D is sulfomethylacrylamide.

28. The method of claim 1, wherein the indicator material is in a composition that does not further comprise a fluorescent dye encapsulated by, coated with, or entrapped within a nonfluorescent polymer;

or a fluorescent dye covalently linked to a non-fluorescent polymer in an amount sufficient to leave a mark on a surface to which the composition is applied after removal of the composition from the surface.

29. The method of claim 1, wherein the indicator material is in a composition that does not further comprise a fluorescent dye encapsulated by, coated with, or entrapped within a nonfluorescent polymer;

or a fluorescent dye covalently linked to a non-fluorescent polymer.

30. The method of claim 1, wherein the indicator material is in a composition that comprises about 8 to about 16 wt. % of the fluorescent polymer;

from about 1 to about 6 wt. % of and amphoteric surfactant;

from about 0.1 to about 0.4 wt. % of a thickener;

from about 0.1 to about 0.7 wt. % of a preservative; and

from about 67 to about 91 wt. % of solvent.

31. The method of claim 1, wherein the indicator material has a 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.

32. The method of claim 1, wherein the indicator material has a light absorption spectrum in the range of about 365 to about 395 nm, and light emission spectrum in the range of about 410 to about 700 nm upon exposure to UV radiation.

33. The method of claim 1, wherein indicator material has the viscosity of a water-thin liquid.

34. The method of claim 1, wherein the indicator material has a viscosity from about 10 to about 6,000 centipoise when measured with a Brookfield LVT viscometer at 25°

C. with a #1 spindle at 60 rpm.

35. The method of claim 1, wherein the indicator material has a viscosity from about 20 to about 200 centipoise when measured with a Brookfield LVT viscometer at 25°

C. with a #1 spindle at 60 rpm.

36. The method of claim 1, wherein the indicator material is applied with an applicator comprising a plastic squeeze bottle with a foam pad attached to the end.

37. The method of claim 1, wherein the indicator material is inconspicuous, transparent, opaque, or semi-opaque before it is applied to the surface.

38. The method of claim 1, wherein the indicator material is inconspicuous, transparent, opaque, or semi-opaque on the surface.

39. The method of claim 1, wherein the indicator material is allowed to dry on the surface.

40. The method of claim 1, wherein the indicator material does not leave behind a residual fluorescent mark when the indicator material is removed during a cleaning process.

41. A kit for evaluating cleaning of a surface, the kit comprising:

an applicator;

an indicator material comprising a water-dispersible fluorescent polymer from polymerization of one or more polymerizable fluorescent monomer units and one or more polymerizable non-fluorescent monomer units and having a weight average molecular weight of 2 to 2000 kDa; and

a portable ultraviolet light emitting light source.

42. The kit of claim 41, wherein the applicator is selected from the group consisting of a spray applicator, a foam pad applicator, a felt tip applicator, a brush, a roll, a wipe, a solid form, or a plastic squeeze bottle with a foam pad attached to the end.

43. The kit of claim 41, wherein the applicator is a bottle or ampule.

44. The kit of claim 41, wherein the applicator is a spray applicator.

45. The kit of claim 41, the kit further comprising a mobile application.

46. The kit of claim 41, wherein the portable ultraviolet light emitting light source emits light having a wavelength range of from about 310 to about 400 nm.