Water-Stabilized Antimicrobial Organosilane Products, Compositions, and Methods for Using the Same

• US 20070237901A1
• Filed: 03/01/2007
• Published: 10/11/2007
• Est. Priority Date: 03/02/2006
• Status: Active Grant

• Current Assignee: Vitec Microgenix Limited
• Original Assignee: Vitec Speciality Chemicals Limited
• Inventors: McMahon, Robert, Moses, Timothy
• Granted Patent: US 7,632,797 B2
• Time in Patent Office: Days
• US Class Current: 427/384
• CPC Class Codes: A01N 2300/00 Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
• CPC Class Codes: A01N 25/22 containing ingredients stabilising the active ingredients
• CPC Class Codes: A01N 25/30 characterised by the surfactants
• CPC Class Codes: A01N 31/02 Acyclic compounds
• CPC Class Codes: A01N 33/12 Quaternary ammonium compounds
• CPC Class Codes: A01N 55/00 Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur containing organo-phosphorus compounds A01N57/00
• CPC Class Codes: D06M 13/463 derived from monoamines
• CPC Class Codes: D06M 13/513 with at least one carbon-silicon bond
• CPC Class Codes: D06M 16/00 Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic

Abstract

The present invention relates to water-stable compositions and compounds formed by mixing an organosilane, optionally having a non-hydrolyzable organic group, but having one or more hydrolyzable groups, and an acidified stabilizing solution prepared from at least one acid, at least one glycol ether, and at least one cationic surfactant, preferably at least one quaternary ammonium salt (QAS), in water. The present invention also relates to methods of treating a substrate by mixing or contacting the substrate with the product, compound, or composition of this invention for a period of time sufficient for treatment of the substrate, methods of antimicrobially treating a food article, methods of antimicrobially coating a fluid container, methods of dyeing and treating a substrate, and methods of antimicrobially coating a latex medical article. The invention also pertains to a treated substrate having adhered thereto the product, compound, or composition of this invention.

Claims

1. A composition comprising an organosilane and an acidic stabilizing solution, wherein the acidic stabilizing solution comprises at least one acid, at least one glycol ether, and at least one cationic surfactant in water.

2. The composition according to claim 1, wherein the organosilane is of the formula R_nSiX_4-n, where n is an integer from 0 to 3, each R is, independently, a non-hydrolyzable organic group, and each X is, independently, a hydrolyzable group.

3. The composition according to claim 2, wherein X is hydroxyl, alkoxy, acetoxy, unsubstituted or substituted acyl, or a halogen.

4. The composition according to claim 1, wherein the organosilane is of the formula I, II, III, or IV

(R¹)₃SiR²N⁺(R³)(R⁴)(R⁵)Y⁻

 

 

(I)
(R¹)₃SiR²N(R³)(R⁴) 

 

(II)
(R¹)₃SiR²R³⁵ 

 

(III)
(R¹)₃Si(R³⁶)(R³⁷) 

 

(IV)

wherein each R¹ is, independently, halogen or R⁶O;

and wherein R⁶ is H, alkyl from 1 to about 24 carbon atoms, acetyl, acetoxy, acyl, propylene glycol, ethylene glycol, polyethylene glycol, polypropylene glycol, block and copolymers of ethylene and propylene glycol, the alkyl monoether from 1 to 24 carbons of propylene glycol, ethylene glycol, polyethylene glycol, polypropylene glycol, block and copolymers of ethylene and propylene glycol, or the monoester of a carbonic acid from 1 to 24 carbons and propylene glycol, ethylene glycol, polyethylene glycol, polypropylene glycol, block and copolymers of ethylene and propylene glycol, octylphenol, nonylphenol, or sorbitan ethers;

and wherein R³⁵ is R⁶, H, halogen, NH₂(CH₂)₂NHR²NH₂R², C₃H₅O₂R², C₄H₅O₂R², NaO(CH₃O)P(O)R², or ClCH₂C₆H₄R²;

and wherein R³⁶ and R³⁷ are, independently, R³⁵, halogen, H, alkyl, isobutyl, phenyl, or n-octyl;

and wherein R² is R⁶, benzyl, vinyl or alkyl;

and wherein R³ and R⁴ are, independently, R³⁵, alkyl alcohol, alkoxy, or alkyl, or R³ and R⁴ can, together, form a morpholine or cyclic or heterocyclic, unsaturated or saturated, five- to seven-membered ring of the formula V;

—

R³—

(R⁷)_k—

R⁴—

 

 

(V)

where k is an integer from 0 to 2;

and wherein R⁷, where the ring is saturated is CH₂, O, S, NH, NH₂⁺, NCH₂CH₂NH₂, NCH₂CH₂NH₃⁺, NCH₂CH₂N(R¹)(R¹), NCH₂CH₂N⁺(R⁸)(R⁹)(R¹⁰), N(alkyl), N(aryl), N(benzyl), CH, N, N⁺H, N⁺(alkyl), N⁺(aryl), N⁺(benzyl), N⁺CH₂—

N, N⁺H—

CH₂—

N, N⁺(alkyl)-CH₂—

N, N⁺(aryl)-CH₂—

N, or N⁺(benzyl)-CH₂—

N;

and wherein each R⁸, R⁹, and R¹⁰ is, independently, benzyl, R³⁷, polyether, alkyl alcohol, alkoxy, or alkyl;

and wherein R⁵ is alkyl alcohol, R³⁵, CH₂C₆H₅, polyether, alkyl, perfluoroalkyl, perfluoroalkylsulfonate, perfluoroalkylcarboxylate, or is a five to seven-membered ring of formula V;

and wherein Y⁻

is an anion.

5. The composition according to claim 1, wherein the acidic stabilizing solution comprises exactly one acid, exactly one glycol ether, and exactly one cationic surfactant in water.

6. The composition according to claim 1, wherein at least one acid is an inorganic acid.

7. The composition according to claim 6, wherein the inorganic acid is a mineral acid.

8. The composition according to claim 7, wherein the mineral acid is hydrochloric acid.

9. The composition according to claim 1, wherein at least one acid is an organic acid.

10. The composition according to claim 9, wherein the organic acid is acetic acid.

11. The composition according to claim 1, wherein at least one glycol ether is diethylene glycol butyl ether.

12. The composition according to claim 1, wherein at least one cationic surfactant is a quaternary ammonium salt.

13. The composition according to claim 12, wherein the quaternary ammonium salt has the following structure:

14. The composition according to claim 13, wherein at least one of R³⁸, R³⁹, R⁴⁰, or R⁴¹ is an alkyl.

15. The composition according to claim 12, wherein the quaternary ammonium salt is an N-alkyl-N,N-Dimethyl-N-Benzyl ammonium chloride.

16. The composition according to claim 1, further comprising water.

17. The composition according to claim 1, wherein the pH of the acidic stabilizing solution is between about 2 and about 3.

18. The composition according to claim 17, wherein the pH of the acidic stabilizing solution is about 2.5.

19. The composition according to claim 1, wherein the at least one glycol ether is not a polyol.

20. The composition according to claim 1, wherein the organosilane comprises from about 0.1 wt % to about 50 wt % of the composition.

21. A method for producing an antimicrobial organosilane composition, comprising:

a) mixing at least one quaternary ammonium salt with at least one glycol ether and water to produce a solution;

b) adding at least one acid to the solution to acidify the solution; and

c) adding the solution to an organosilane.

22. The method according to claim 21, wherein the organosilane is of the formula R_nSiX_4-n, where n is an integer from 0 to 3, each R is, independently, a non-hydrolyzable organic group, and each X is, independently, a hydrolyzable group.

23. The method according to claim 22, wherein X is hydroxyl, alkoxy, acetoxy, unsubstituted or substituted acyl, or a halogen.

24. The method according to claim 21, wherein the organosilane is of the formula I, II, III, or IV

(R¹)₃SiR²N⁺(R³)(R⁴)(R⁵)Y⁻

 

 

(I)
(R¹)₃SiR²N(R³)(R⁴) 

 

(II)
(R¹)₃SiR²R³⁵ 

 

(III)
(R¹)₃Si(R³⁶)(R³⁷) 

 

(IV)

wherein each R¹ is, independently, halogen or R⁶O;

and wherein R⁶ is H, alkyl from 1 to about 24 carbon atoms, acetyl, acetoxy, acyl, propylene glycol, ethylene glycol, polyethylene glycol, polypropylene glycol, block and copolymers of ethylene and propylene glycol, the alkyl monoether from 1 to 24 carbons of propylene glycol, ethylene glycol, polyethylene glycol, polypropylene glycol, block and copolymers of ethylene and propylene glycol, or the monoester of a carbonic acid from 1 to 24 carbons and propylene glycol, ethylene glycol, polyethylene glycol, polypropylene glycol, block and copolymers of ethylene and propylene glycol, octylphenol, nonylphenol, or sorbitan ethers;

and wherein R³⁵ is R⁶, H, halogen, NH₂(CH₂)₂NHR²NH₂R², C₃H₅O₂R², C₄H₅O₂R², NaO(CH₃O)P(O)R², or ClCH₂C₆H₄R²;

and wherein R³⁶ and R³⁷ are, independently, R³⁵, halogen, H, alkyl, isobutyl, phenyl, or n-octyl;

and wherein R² is R⁶, benzyl, vinyl or alkyl;

and wherein R³ and R⁴ are, independently, R³⁵, alkyl alcohol, alkoxy, or alkyl, or R³ and R⁴ can, together, form a morpholine or cyclic or heterocyclic, unsaturated or saturated, five- to seven-membered ring of the formula V;

—

R³—

(R⁷)_k—

R⁴—

 

 

(V)

where k is an integer from 0 to 2;

and wherein R⁷, where the ring is saturated is CH₂, O, S, NH, NH₂⁺, NCH₂CH₂NH₂, NCH₂CH₂NH₃⁺, NCH₂CH₂N(R⁸)(R⁹), NCH₂CH₂N⁺(R¹)(R⁹)(R¹⁰), N(alkyl), N(aryl), N(benzyl), CH, N, N⁺H, N⁺(alkyl), N⁺(aryl), N⁺(benzyl), N—

CH₂—

N, N⁺H—

CH₂—

N, N⁺(alkyl)-CH₂—

N, N⁺(aryl)-CH₂—

N, or N⁺(benzyl)-CH₂—

N;

and wherein each R⁸, R⁹, and R¹⁰ is, independently, benzyl, R³⁷, polyether, alkyl alcohol, alkoxy, or alkyl;

and wherein R⁵ is alkyl alcohol, R³⁵, CH₂C₆H₅, polyether, alkyl, perfluoroalkyl, perfluoroalkylsulfonate, perfluoroalkylcarboxylate, or is a five to seven-membered ring of formula V;

and wherein Y⁻

is an anion.

25. The method according to claim 21, wherein the organosilane is 3-(trimethoxysilyl)propyl-dimethyloctadecyl ammonium chloride.

26. The method according to claim 21, wherein at least one acid is an inorganic acid.

27. The method according to claim 26, wherein the inorganic acid is a mineral acid.

28. The method according to claim 27, wherein the mineral acid is hydrochloric acid.

29. The method according to claim 21, wherein at least one acid is an organic acid.

30. The method according to claim 29, wherein the organic acid is acetic acid.

31. The method according to claim 21, wherein at least one glycol ether is diethylene glycol butyl ether.

32. The method according to claim 21, wherein at least one quaternary ammonium salt has the following structure:

33. The method according to claim 32, wherein at least one of R³⁸, R³⁹, R⁴⁰, or R⁴¹ is an alkyl.

34. The method according to claim 21, wherein at least one quaternary ammonium salt is an N-alkyl-N,N-Dimethyl-N-Benzyl ammonium chloride.

35. The method according to claim 21, comprising:

a) mixing exactly one quaternary ammonium salt with a glycol ether and water to produce a solution; and

b) adding exactly one acid to the solution to acidify the solution.

36. The method according to claim 21, wherein the pH of the solution after acidifying the solution is between about 2 and about 3.

37. The method according to claim 36, wherein the pH of the solution after acidifying the solution is about 2.5.

38. The method according to claim 21, wherein the at least one glycol ether is not a polyol.

39. The method according to claim 21, wherein the organosilane comprises about 0.1 wt % to about 50 wt % of the antimicrobial organosilane composition.

40. The method according to claim 21, wherein the at least one quaternary ammonium salt comprises about 0.1 wt % to about 5 wt % of the solution.

41. The method according to claim 21, wherein the at least one glycol ether comprises about 5 wt % to about 20 wt % of the solution.

42. A method for treating a substrate, comprising contacting the substrate with a composition;

wherein the composition comprises an organosilane and an acidic stabilizing solution; and

wherein the acidic stabilizing solution comprises at least one acid, at least one glycol ether, and at least one cationic surfactant in water.

43. The method according to claim 42, wherein the organosilane is of the formula R_nSiX_4-n, where n is an integer from 0 to 3, each R is, independently, a non-hydrolyzable organic group, and each X is, independently, a hydrolyzable group.

44. The method according to claim 43, wherein X is hydroxyl, alkoxy, acetoxy, unsubstituted or substituted acyl, or a halogen.

45. The method according to claim 42, wherein the organosilane is of the formula I, II, III, or IV

(R¹)₃SiR²N⁺(R³)(R⁴)(R⁵)Y⁻

 

 

(1)
(R¹)₃SiR²N(R³)(R⁴) 

 

(II)
(R¹)₃SiR²R³⁵ 

 

(III)
(R¹)₃Si(R³⁶)(R³⁶) 

 

(IV)

wherein each R¹ is, independently, halogen or R⁶O;

and wherein R⁶ is H, alkyl from 1 to about 24 carbon atoms, acetyl, acetoxy, acyl, propylene glycol, ethylene glycol, polyethylene glycol, polypropylene glycol, block and copolymers of ethylene and propylene glycol, the alkyl monoether from 1 to 24 carbons of propylene glycol, ethylene glycol, polyethylene glycol, polypropylene glycol, block and copolymers of ethylene and propylene glycol, or the monoester of a carbonic acid from 1 to 24 carbons and propylene glycol, ethylene glycol, polyethylene glycol, polypropylene glycol, block and copolymers of ethylene and propylene glycol, octylphenol, nonylphenol, or sorbitan ethers;

and wherein R³⁵ is R⁶, H, halogen, NH₂(CH₂)₂NHR²NHR², C₃H₅O₂R², C₄H₅O₂R², NaO(CH₃O)P(O)R², or ClCH₂C₆H₄R²;

and wherein R³⁶ and R³⁷ are, independently, R³⁵, halogen, H, alkyl, isobutyl, phenyl, or n-octyl;

and wherein R² is R⁶, benzyl, vinyl or alkyl;

and wherein R³ and R⁴ are, independently, R³⁵, alkyl alcohol, alkoxy, or alkyl, or R³ and R⁴ can, together, form a morpholine or cyclic or heterocyclic, unsaturated or saturated, five- to seven-membered ring of the formula V;

—

R³—

(R⁷)_k—

R⁴—

 

 

(V)

where k is an integer from 0 to 2;

and wherein R⁷ where the ring is saturated is CH₂, O, S, NH, NH₂⁺, NCH₂CH₂NH₉, NCH₂CH₂NH₃⁺, NCH₂CH₂N(R¹)(R⁹), NCH₂CH₂N⁺(R⁸)(R⁹)(R¹⁰), N(alkyl), N(aryl), N(benzyl), CH, N, N⁺H, N⁺(alkyl), N⁺(aryl), N⁺(benzyl), N—

CH₂—

N, N⁺H—

CH, —

N, N⁺(alkyl)-CH₂—

N, N⁺(aryl)-CH₂—

N, or N⁺(benzyl)-CH₂—

N;

and wherein each R⁸, R⁹, and R¹⁰ is, independently, benzyl, R³⁷ polyether, alkyl alcohol, alkoxy, or alkyl;

and wherein R⁵ is alkyl alcohol, R³⁵, CH₂C₆H₅, polyether, alkyl, perfluoroalkyl, perfluoroalkylsulfonate, perfluoroalkylcarboxylate, or is a five to seven-membered ring of formula V;

and wherein Y⁻

is an anion.

46. The method according to claim 42, wherein the organosilane is 3-(trimethoxysilyl)propyl-dimethyloctadecyl ammonium chloride.

47. The method according to claim 42, wherein the acidic stabilizing solution comprises exactly one acid, exactly one glycol ether, and exactly one cationic surfactant in water.

48. The method according to claim 42, wherein at least one acid is an inorganic acid.

49. The method according to claim 48, wherein the inorganic acid is a mineral acid.

50. The method according to claim 49, wherein the mineral acid is hydrochloric acid.

51. The method according to claim 42, wherein at least one acid is an organic acid.

52. The method according to claim 51, wherein the organic acid is acetic acid.

53. The method according to claim 42, wherein at least one glycol ether is diethylene glycol butyl ether.

54. The method according to claim 42, wherein at least one cationic surfactant is a quaternary ammonium salt.

55. The method according to claim 54, wherein the quaternary ammonium salt has the following structure:

56. The method according to claim 55, wherein at least one of R³⁸, R³⁹, R⁴⁰, or R⁴¹ is an alkyl.

57. The method according to claim 54, wherein the quaternary ammonium salt is an N-alkyl-N,N-Dimethyl-N-Benzyl ammonium chloride.

58. The method according to claim 42, wherein the pH of the acidic stabilizing solution is between about 2 and about 3.

59. The method according to claim 58, wherein the pH of the acidic stabilizing solution is about 2.5.

60. The method according to claim 42, wherein the at least one glycol ether is not a polyol.

61. The method according to claim 42, wherein the organosilane comprises about 0.1 wt % to about 50 wt % of the antimicrobial organosilane composition.

62. The method according to claim 42, wherein the composition further comprises at least one dye.

63. The method according to claim 42, wherein the substrate is coated with the composition, and wherein the substrate and composition are subsequently dried.

64. The method according to claim 42, wherein further comprising heating the substrate to bind the composition to the substrate.

65. The method according to claim 42, wherein the substrate is contacted with the composition for a period of time of about 15 seconds to about 48 hours.

66. The method according to claim 65, wherein the substrate is contacted with the composition for a period of time of about 5 minutes to about 1 hour.

67. The method according to claim 42, wherein the composition is applied to a substrate selected from the group consisting of a concrete pipe, food article, fluid container, glove, latex medical article, a tooth brush, a comb, a hair brush, a denture, an orthodontic retainer, a spa or pool filter, an air filter, an HVAC air system, a cabin air system, a marble article, a statue, an exposed work of art, an HDP plastic cover, a silicone or TEFLON®

coated fiberglass article, a Dryvitt finish, a stucco finish, blended cotton, a bio-film, a bio-adhesive, a single ply roofing, a roofing shingle, and a fiberglass reinforcement product, a textile, a carpet, a carpet backing, a clothing article, a sponge, a plastic, a metal, a surgical dressing, masonry, sand, silica, alumina, alumina chlorohydrate, titanium dioxide, calcium carbonate, wood, a glass bead, a tile a floor, a curtain, a marine product, a tent, a backpack, roofing, siding, fencing, trim, insulation, wall-board, a trash receptacle, a water purification system, soil, a buffer pad, an aquarium filter, a sand bag, a sail, a rope, a tarpaulin, a shoe, a sock, a towel, a disposable wipe, and hosiery.

68. A method for antimicrobially enhancing a product, comprising admixing the product with a composition;

wherein the composition comprises an organosilane and an acidic stabilizing solution; and

wherein the acidic stabilizing solution comprises at least one acid, at least one glycol ether, and at least one cationic surfactant in water.

69. The method according to claim 68, wherein the organosilane is of the formula R_nSiX_4-n, where n is an integer from 0 to 3, each R is, independently, a non-hydrolyzable organic group, and each X is, independently, a hydrolyzable group.

70. The method according to claim 69, wherein X is hydroxyl, alkoxy, acetoxy, unsubstituted or substituted acyl, or a halogen.

71. The method according to claim 68, wherein the organosilane is of the formula I, II, III, or IV

(R¹)₃SiR²N⁺(R³)(R⁴)(R⁵)Y⁻

 

 

(I)
(R¹)₃SiR²N(R³)(R⁴) 

 

(II)
(R¹)₃SiR²R³⁵ 

 

(III)
(R¹)₃Si(R³⁶)(R³⁷) 

 

(IV)

wherein each R¹ is, independently, halogen or R⁶O;

and wherein R⁶ is H, alkyl from 1 to about 24 carbon atoms, acetyl, acetoxy, acyl, propylene glycol, ethylene glycol, polyethylene glycol, polypropylene glycol, block and copolymers of ethylene and propylene glycol, the alkyl monoether from 1 to 24 carbons of propylene glycol, ethylene glycol, polyethylene glycol, polypropylene glycol, block and copolymers of ethylene and propylene glycol, or the monoester of a carbonic acid from 1 to 24 carbons and propylene glycol, ethylene glycol, polyethylene glycol, polypropylene glycol, block and copolymers of ethylene and propylene glycol, octylphenol, nonylphenol, or sorbitan ethers;

and wherein R³⁵ is R⁶, H, halogen, NH₂(CH₂)₂NHR²NH₂R², C₃H₅O₂R², C₄H₅O₂R², NaO(CH₃O)P(O)R², or ClCH₂C₆H₄R²;

and wherein R³⁶ and R³⁷ are, independently, R³⁵, halogen, H, alkyl, isobutyl, phenyl, or n-octyl;

and wherein R² is R⁶, benzyl, vinyl or alkyl;

and wherein R³ and R⁴ are, independently, R³⁵, alkyl alcohol, alkoxy, or alkyl, or R³ and R⁴ can, together, form a morpholine or cyclic or heterocyclic, unsaturated or saturated, five- to seven-membered ring of the formula V;

—

R³—

(R⁷)_k—

R⁴—

 

 

(V)

where k is an integer from 0 to 2;

and wherein R⁷, where the ring is saturated is CH₂, O, S, NH, NH₂⁺, NCH₂CH₂NH₂, NCH₂CH₂NH₃⁺, NCH₂CH₂N(R⁸)(R⁹), NCH₂CH₂N⁺(R⁸)(R⁹)(R¹⁰), N(alkyl), N(aryl), N(benzyl), CH, N, N⁺H, N⁺(alkyl), N⁺(aryl), N⁺(benzyl), N—

CH₂—

N, N⁺H—

CH, —

N, N⁺(alkyl)-CH₂—

N, N⁺(aryl)-CH₂—

N, or N⁺(benzyl)-CH₂—

N;

and wherein each R⁸, R⁹, and R¹⁰ is, independently, benzyl, R³⁷, polyether, alkyl alcohol, alkoxy, or alkyl;

and wherein R⁵ is alkyl alcohol, R₃₅, CH₂C₆H₅, polyether, alkyl, perfluoroalkyl, perfluoroalkylsulfonate, perfluoroalkylcarboxylate, or is a five to seven-membered ring of formula V;

and wherein Y⁻

is an anion.

72. The method according to claim 68, wherein the organosilane is 3-(trimethoxysilylpropyl-dimethyloctadecyl ammonium chloride.

73. The method according to claim 68, wherein the acidic stabilizing solution comprises exactly one acid, exactly one glycol ether, and exactly one cationic surfactant in water.

74. The method according to claim 68, wherein at least one acid is an inorganic acid.

75. The method according to claim 74, wherein the inorganic acid is a mineral acid.

76. The method according to claim 75, wherein the mineral acid is hydrochloric acid.

77. The method according to claim 68, wherein at least one acid is an organic acid.

78. The method according to claim 77, wherein the organic acid is acetic acid.

79. The method according to claim 68, wherein at least one glycol ether is diethylene glycol butyl ether.

80. The method according to claim 68, wherein at least one cationic surfactant is a quaternary ammonium salt.

81. The method according to claim 80, wherein the quaternary ammonium salt has the following structure:

82. The method according to claim 81, wherein at least one of R³⁸, R³⁹, R⁴⁰, or R⁴¹ is an alkyl.

83. The method according to claim 80, wherein the quaternary ammonium salt is an N-alkyl-N,N-Dimethyl-N-Benzyl ammonium chloride.

84. The method according to claim 68, wherein the pH of the acidic stabilizing solution is between about 2 and about 3.

85. The method according to claim 84, wherein the pH of the acidic stabilizing solution is about 2.5.

86. The method according to claim 68, wherein the at least one glycol ether is not a polyol.

87. The method according to claim 68, wherein the organosilane comprises about 0.1 wt % to about 50 wt % of the antimicrobial organosilane composition.

88. The method according to claim 68, wherein the composition further comprises at least one dye.

89. The method according to claim 68, wherein the composition is admixed with a product selected from the group consisting of an acrylic, polyester, concrete, a primer, a paint, an ink, a dye, an adhesive, an agricultural product, a plastic, a bleaching agent, a cosmetic, a lotion, a cream, an ointment, a disinfectant sanitizer) a wood preservative, pulp, paper, cooling water, a laundry additive, rubbing alcohol, a flower preservative, and a waterproofing solution.

90. A composition formed by mixing an organosilane and an acidic stabilizing solution, wherein the acidic stabilizing solution comprises at least one acid, at least one glycol ether, and at least one cationic surfactant in water.

91. The composition according to claim 90, wherein the organosilane is of the formula R_nSiX_4-n, where n is an integer from 0 to 3, each R is, independently, a non-hydrolyzable organic group, and each X is, independently, a hydrolyzable group.

92. The composition according to claim 91, wherein X is hydroxyl, alkoxy, acetoxy, unsubstituted or substituted acyl, or a halogen.

93. The composition according to claim 90, wherein the organosilane is of the formula I, II, III, or IV

(R¹)₃SiR²N⁺(R³)(R⁴)(R¹)Y⁻

 

 

(1)
(R¹)₃SiR²N(R³)(R⁴) 

 

(II)
(R¹)₃SiR²R³⁵ 

 

(III)
(R¹)₃Si(R³⁶)(R³⁷) 

 

(IV)

wherein each R¹ is, independently, halogen or R⁶O;

and wherein R⁶ is H, alkyl from 1 to about 24 carbon atoms, acetyl, acetoxy, acyl, propylene glycol, ethylene glycol, polyethylene glycol, polypropylene glycol, block and copolymers of ethylene and propylene glycol, the alkyl monoether from 1 to 24 carbons of propylene glycol, ethylene glycol, polyethylene glycol, polypropylene glycol, block and copolymers of ethylene and propylene glycol, or the monoester of a carbonic acid from 1 to 24 carbons and propylene glycol, ethylene glycol, polyethylene glycol, polypropylene glycol, block and copolymers of ethylene and propylene glycol, octylphenol, nonylphenol, or sorbitan ethers;

and wherein R³⁵ is R⁶, H, halogen, NH₂(CH₂)₂NHR² NH₂R², C₃H₅O₂R², C₄H₅O₂R², NaO(CH₃O)P(O)R², or ClCH₂C₆H₄R²;

and wherein R³⁶ and R³⁷ are, independently, R³⁵, halogen, H, alkyl isobutyl, phenyl, or n-octyl;

and wherein R² is R⁶, benzyl, vinyl or alkyl;

and wherein R³ and R⁴ are, independently, R³⁵, alkyl alcohol, alkoxy, or alkyl, or R³ and R⁴ can, together, form a morpholine or cyclic or heterocyclic, unsaturated or saturated, five- to seven-membered ring of the formula V;

—

R³—

(R⁷)_k—

R⁴—

 

 

(V)

where k is an integer from 0 to 2;

and wherein R⁷, where the ring is saturated is CH₂, O, S, NH, NH₂⁺, NCH₂CH₂NH₂, NCH₂CH₂NH₃⁺, NCH₂CH₂N(R⁸)(R⁹), NCH₂CH₂N⁺(R⁸)(R⁹)(R¹⁰), N(alkyl), N(aryl), N(benzyl), CH, N, N⁺H, N⁺(alkyl), N⁺(aryl), N⁺(benzyl), N—

CH)—

N, N⁺H—

CH₂—

N, N⁺(alkyl)-CH₂—

N, N⁺(aryl)-CH₂—

N, or N⁺(benzyl)-CH₂—

N;

and wherein each R⁸, R⁹, and R¹⁰ is, independently, benzyl, R³⁷, polyether, alkyl alcohol, alkoxy, or alkyl;

and wherein R⁵ is alkyl alcohol, R³⁵, CH₂C₆H₅, polyether, alkyl, perfluoroalkyl, perfluoroalkylsulfonate, perfluoroalkylcarboxylate, or is a five to seven-membered ring of formula V;

and wherein Y⁻

is an anion.

94. The composition according to claim 90, wherein at least one acid is hydrochloric acid.

95. The composition according to claim 90, wherein at least one acid is acetic acid.

96. The composition according to claim 90, wherein at least one glycol ether is diethylene glycol butyl ether.

97. The composition according to claim 90, wherein at least one cationic surfactant is a quaternary ammonium salt.

98. The composition according to claim 97, wherein the quaternary ammonium salt has the following structure:

99. The composition according to claim 98, wherein at least one of R³⁸, R³⁹, R⁴⁰, or R⁴¹ is an alkyl.

100. The composition according to claim 97, wherein the quaternary ammonium salts is an N-alkyl-N,N-Dimethyl-N-Benzyl ammonium chloride.

101. The composition according to claim 90, wherein the pH of the acidic stabilizing solution is about 2.5.