Surface coating compositions and methods
View Patent ↗The invention provides surface coating compositions comprising a preservative comprising 9-decenoic acid, salts of 9-decenoic acid, esters of 9-decenoic acid, or combinations thereof. The surface coating compositions may be water-based coatings (e.g., a latex paint) or solvent-based coatings (e.g., a solvent-based paint). The surface coating compositions may be paints, stains, varnishes, concrete coatings, anti-graffiti coatings, and the like. Methods for protecting a surface coating composition from in-can spoilage and protecting a coating of the surface coating composition from deterioration by the action of microorganisms are also described.
1. A surface coating composition comprising:
a coating-forming component; and
a preservative comprising 9-decenoic acid, a salt of 9-decenoic acid, an ester of 9-decenoic acid, or a combination thereof;
wherein the coating composition has a pH of at least 6.75; and
wherein the preservative provides anti-microbial activity against gram-negative bacteria, gram-positive bacteria, mold, fungi, and algae, in the coating composition; and
wherein the surface coating is a latex paint comprising a binder and pigment.
2. The surface coating composition of claim 1 , wherein the preservative is a salt of 9-decenoic acid according to formula (III):
K +n [R − ] n (III)
where R 31 is
n is an integer ranging from 1 to 2; and
K +n is a +n charged cation.
3. The surface coating composition of claim 2 , wherein K +n is selected from the group consisting of Li + , Na + , and K + , Ag + , NH 4 + , or quaternary ammonium.
4. The surface coating composition of claim 2 , wherein K +n is selected from the group consisting of Ca +2 , Mg +2 , Zn +2 , Cu +2 , and Fe +2 .
5. The surface coating of claim 1 , wherein the preservative is present in an amount ranging from about 0.01% to about 5.0% by weight.
6. The surface coating of claim 1 , wherein the preservative is present in an amount ranging from about 0.1% to about 1.0% by weight.
7. The surface coating of claim 1 ,wherein the preservative comprises: a first preservative comprising 9-decenoic acid, an ester of 9-decenoic acid, or a salt of 9-decenoic acid; and a second preservative selected from the group consisting of 4,4-dimethyloxazolidine; 3,4,4,-trimethyloxazolidine; 1,2-dibromo-2,4-dicyanobutane; 2[(hydroxymethyl)-amino]ethanol; 2-[(hydroxymethyl)-amino]propanol; 1-(3-chlorallyI)-3,5,7-triaza-1-azoniaadamantane chloride; 1,2-benzisothiazolin-3-one; 5-chloro-2-methyl-4-isothiazolin-3-one; 2-methyl-4-isothiazolin-3-one; 5-hydroxymethoxy -methyl-1-aza-3,7-dioxa-bicyclo-[3.3.0]octane; 5-hydroxymethyl-1-aza-3,7-dioxabicyclo -[3.3.0]octane; 5-hydroxypolymethyl-1-aza-3,7-dioxabicyclo[3.3.0]-octane; hexahydro-1,3,5-triethyl-s-triazine; 2-hydroxymethyl-2-nitro-1,3 propanediol; chloroacetamide; methyl chloroisothiazolinone; methylisothiazolinone; 2,4,4 ′trichloro-2-hydroxydiphenyl ether; metal salts; glycols; alcohols; quaternary ammonium salts; phenol derivatives; tetrachloroisophthalonitrile, 2-iodo-2-propynyl butyl carbamate, 2-n-octyl-4-isothiazolin-3-one, diiodomethyl-p-tolylsulphone, n-(trimethylthio)phthalimide, carbendazim, dichloro-octylisothiazolinone, zinc pyrithione, thiuram; and barium meta-borate.
8. The surface coating of claim 7 , wherein the first preservative is present in an amount ranging from about 0.01% to about 5% weight and the second preservative is present in an amount ranging from about 0.01% to about 5% weight.
9. The surface coating of claim 8 , wherein the preservative comprises about 90% weight or greater 9-decenoic acid or an ester or a salt thereof.
10. The surface coating composition of claim 8 , wherein the preservative comprises less than about 0.5% weight undecenoic acid.
11. The surface coating composition of claim 8 , wherein the preservative comprises less than about 0.5% weight 8-nonenoic acid, less than about 0.5% n-decanoic acid, less than about 0.5% weight 3-decenoic acid, and less than about 0.5% weight undecenoic acid.
12. The surface coating of claim 8 , wherein the preservative comprises about 99% weight or greater 9-decenoic acid or an ester or a salt thereof.
13. The surface coating of claim 8 , wherein the preservative comprises about 99.8% weight or greater 9-decenoic acid or an ester or a salt thereof.
14. The surface coating composition of claim 8 , wherein the preservative comprises less than about 0.5% weight 8-nonenoic acid.
15. The surface coating composition of claim 8 , wherein the preservative comprises less than about 0.5% weight n-decanoic acid.
16. The surface coating composition of claim 8 , wherein the preservative comprises less than about 0.5% weight 3-decenoic acid.
17. The surface coating of claim 1 , wherein the preservative is formed by metathesis.
18. The surface coating of claim 17 , wherein the preservative is formed by cross-metathesis of ethylene or an α-olefin with a starting material comprising:
(a) a triglyceride comprising C9-C10 unsaturated fatty acid esters, (b) a C9-C10 unsaturated fatty acid, (c) a C9-C10 unsaturated fatty ester, or (d) a mixture thereof.
19. The surface coating of claim 18 , wherein the α-olefin is 1-propene, 1-butene, 1-pentene, 1-hexene, 1-heptene, 1-octene, 1-decene, and mixtures thereof.
20. The surface coating of claim 18 , wherein the starting material is treated with an adsorbent prior to cross-metathesis.
21. The surface coating of claim 20 , wherein the adsorbent comprises sodium bisulfite, magnesium silicate, sodium borohydride, or combinations thereof.
22. The surface coating of claim 21 , wherein the starting material has a peroxide value of about 1 or less.
23. The surface coating composition of claim 1 wherein the surface coating composition has a neutral or alkaline pH.
24. The surface coating composition of claim 1 wherein the surface coating composition has a pH of at least 7.5.
25. The surface coating composition of claim 1 wherein the surface coating composition has a pH of at least 8.
26. The surface coating composition of claim 1 wherein the surface coating composition has a pH of at least 8.5.
27. A surface coating composition comprising:
a coating-forming component; and
a preservative;
wherein the coating composition has a pH of at least 6.75; and
wherein the preservative provides anti-microbial activity against gram-negative bacteria, gram-positive bacteria, mold, fungi, and algae, in the coating composition; wherein the preservative is a salt of 9-decenoic acid according to formula (III):
K +n [R − ] n (III)
where R − is
n is an integer ranging from 1 to 2; and
K +n is a +n charged cation
wherein K +n is selected from the group consisting of Al +3 , Fe +3 and Ce +3 .
28. A method of coating a surface, the method comprising applying a surface coating composition to a surface to form a coating on the surface,
wherein the surface coating composition includes a coating-forming component that forms the coating and a preservative comprising 9-decenoic acid, a salt of 9-decenoic acid, an ester of 9-denoic acid, or a combination thereof;
wherein the coating composition has a pH of at least 6.75;
wherein the preservative provides anti-microbial activity against gram-negative bacteria, gram-positive bacteria, mold, fungi, and algae, in the coating composition; and
wherein the surface coating composition is a latex paint comprising a binder and pigment.
29. The method of claim 28 , wherein the preservative provides the coating antimicrobial properties to resist deterioration of the coating by the action of a microorganism.
30. The method of claim 28 , wherein the preservative provides the surface coating composition antimicrobial properties to resist in-can spoilage.
31. The method of claim 28 , wherein the preservative is 9-decenoic acid.
32. The method of claim 28 , wherein the preservative is an ester of 9-decenoic acid according to formula (II):
where —R is an organic group.
33. The method of claim 32 , wherein —R is an aliphatic group or an aryl group.
34. The method of claim 32 , wherein —R is a C1 to C18 alkyl group.
35. The method of claim 32 , wherein —R is methyl, ethyl, propyl, butyl, heptyl, octyl, nonyl, decyl, dodecyl, or octadecyl.
36. The method of claim 32 , wherein —R is a C8 to C16 alkyl group.
37. The method of claim 28 wherein the preservative is a salt of 9-decenoic acid according to formula (III):
K +n [R − ] n (III)
where R − is
where K +n is a +n charged cation; and
n is an integer ranging from 1 to 2.
38. The method of claim 37 , wherein K +n is selected from the group consisting of Li + , Na + , and K + , Ag + , NH 4 + , or quaternary ammonium.
39. The method of claim 37 , wherein K +n is selected from the group consisting of Ca +2 , Mg +2 , Zn +2 , Cu +2 , and Fe +2 .
40. The method of claim 28 , wherein the preservative is present in an amount ranging from about 0.01% to about 5% weight.
41. The method of claim 28 , wherein the preservative is present in an amount ranging from about 0.1% to about 1% weight.
42. The method of claim 28 , wherein the preservative comprises: a first preservative comprising 9-decenoic acid, an ester of 9-decenoic acid, or a salt of 9-decenoic acid; and a second preservative selected from the group consisting of 4,4-dimethyloxazolidine; 3,4,4,-trimethyloxazolidine; 1,2-dibromo-2,4-dicyanobutane; 2 [(hydroxymethyl)-amino]ethanol; 2-[(hydroxymethyl)-amino]propanol; 1-(3-chlorallyl) -3,5,7-triaza-1-azoniaadamantane chloride; 1,2-benzisothiazolin-3-one; 5-chloro-2-methyl -4-isothiazolin-3-one;2-methyl-4-isothiazolin-3-one; 5-hydroxymethoxy-methyl-1-aza-3,7-dioxa-bicyclo-[3.3.0]octane; 5-hydroxymethyl-1-aza-3,7-dioxabicyclo-[3.3.0 ]octane; 5-hydroxypolymethyl-1-aza-3,7-dioxabicyclo[3.3.0]-octane; hexahydro-1,3,5-triethyl-s -triazine; 2-hydroxymethyl-2-nitro-1,3 propanediol; chloroacetamide; methyl chloroisothiazolinone; methylisothiazolinone; 2,4,4′trichloro-2-hydroxydiphenyl ether; metal salts; glycols; alcohols; quaternary ammonium salts; phenol derivatives; tetrachloroisophthalonitrile, 2-iodo-2-propynyl butyl carbamate, 2-n-octyl-4-isothiazolin-3-one, diiodomethyl-p-tolylsulphone, n-(trimethylthio)phthalimide, carbendazim, dichloro -octylisothiazolinone, zinc pyrithione, thiuram; and barium meta-borate.
43. The method of claim 42 , wherein the first preservative is present in an amount ranging from about 0.01% weight to about 5% weight and the second preservative is present in an amount ranging from about 0.01% weight to about 5% weight.
44. The method of claim 28 , wherein the preservative is formed by metathesis.
45. The method of claim 44 , wherein the preservative is formed by cross-metathesis of ethylene or an α-olefin with a starting material comprising: (a) a triglyceride comprising C9-C10 unsaturated fatty acid esters, (b) a C9-C10 unsaturated fatty acid, (c) a C9-C10 unsaturated fatty ester, or (d) a mixture thereof.
46. The method of claim 45 , wherein the α-olefin is 1-propene, 1-butene, 1-pentene, 1-hexene, 1-heptene, 1-octene, 1-decene, and mixtures thereof.
47. The method of claim 45 , wherein the starting material is treated with an adsorbent prior to cross-metathesis.
48. The method of claim 47 , wherein the adsorbent comprises sodium bisulfite, magnesium silicate, sodium borohydride, or combinations thereof.
49. The method of claim 48 , wherein the starting material has a peroxide value of about 1 or less.
50. The method of claim 44 , wherein the preservative comprises about 90% weight or greater 9-decenoic acid or an ester or a salt thereof.
51. The method of claim 44 , wherein the preservative comprises about 99% weight or greater 9-decenoic acid or an ester or a salt thereof.
52. The method of claim 44 , wherein the preservative comprises about 99.8% weight or greater 9-decenoic acid or an ester or a salt thereof.
53. The method of claim 44 , wherein the preservative comprises less than about 0.5% weight 8-nonenoic acid.
54. The method of claim 44 , wherein the preservative comprises less than about 0.5% weight n-decanoic acid.
55. The method of claim 44 , wherein the preservative comprises less than about 0.5% weight 3-decenoic acid.
56. The method of claim 44 , wherein the preservative comprises less than about 0.5% weight undecenoic acid.
57. A method of coating a surface, the method comprising applying a surface coating composition to a surface to form a coating on the surface,
wherein the surface coating composition includes a coating-forming component that forms the coating and a preservative comprising 9-decenoic acid;
wherein the coating composition has a pH of at least 6.75;
wherein the preservative provides anti-microbial activity against gram-negative bacteria, gram-positive bacteria, mold, fungi, and algae, in the coating composition;
wherein the salt is 9-decenoic acid according to formula (III):
K +n [R − ] n (III)
where R − is
where K +n is a +n charged cation; and
n is an integer ranging from 1 to 2; and
wherein K +n is selected from the group consisting of Al 3+ , Fe 3+ , and Ce 3+ .