Ether-stabilized organosilane compositions and methods for using the same

• US 6,113,815 A
• Filed: 07/16/1998
• Issued: 09/05/2000
• Est. Priority Date: 07/18/1997
• Status: Expired due to Term

• Current Assignee: Inhold LLC
• Original Assignee: Bioshield Technologies, Inc. (International Biochemical Industries, Inc.)
• Inventors: Moses, Timothy C., Elfersy, Jacques E., Berkner, Joachim
• Primary Examiner(s): McKane, Joseph
• Assistant Examiner(s): Oswecki, Jane C.
• Application Number:
  US09/116,636
• Time in Patent Office: 782 Days
• Field of Search: 556/407, 556/408, 556/410, 556/413, 528/20, 528/21, 528/23, 528/26, 514/63, 424/406, 424/407, 424/411, 252/588, 252/589, 504/114
• US Class Current: 252/588
• 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 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: A61L 2/18 Liquid substances or solutions comprising solids or dissolved gases
• CPC Class Codes: C07F 7/1804 Compounds having Si-O-C linkages Si-O-acyl linkages C07F7/1896
• CPC Class Codes: C08G 77/26 nitrogen-containing groups
• CPC Class Codes: C09D 183/08 containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
• CPC Class Codes: C09D 4/00 Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
• CPC Class Codes: D06M 13/165 Ethers D06M13/11 takes precedence
• 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
• CPC Class Codes: D06P 1/64 using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
• CPC Class Codes: D06P 1/65131 Compounds containing ether or acetal groups

Abstract

The composition formed by mixing an organosilane with an ether. Water-stabilized organosilane compounds. A water stable composition made from the ether and organosilane composition and water. A method 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. A treated substrate having adhered thereto the product, compound, or composition of this invention. A method of dyeing and treating a substrate. A method of antimicrobially treating a food article. A method of antimicrobially coating a fluid container. A method of antimicrobially coating a latex medical article.

Claims

1. A composition comprising a mixture of:

a) an organosilane of the formula R_n SiX_4-n, wherein n is an integer of from 0 to 3; and

R is, independently, a nonhydrolyzable organic group, and each X is, independently, a hydrolyzable group;

with

b) an ether of the formula R--O--R, wherein R is, independently, an organic group, and the ether has either a hydroxy functionality or a carboxylic ester functionality.

2. The composition of claim 1, wherein n is an integer from 0 to 2;

each R of the organosilane formula is, independently, alkyl, alkyl alcohol, or aromatic;

each X is, independently, hydroxy, alkoxy, halogen, acetyl, acetoxy, acyl, acyloxy, a hydroxylated polymeric moiety, polyglycol, or polyalkylether.

3. The composition of claim 1, wherein each R of the ether formula is, independently, alkyl, alkyl glycol, alkyl alcohol or aromatic alcohol;

or R of the ether formula is alkyl polyol, polyglycol, alkyl polyglycol, alkyl alcohol, aromatic alcohol, cyclic alcohol, or polyalkylether.

4. The composition of claim 2 wherein the hydroxyl hydrogens or hydroxyl groups of the ether formula are substituted by R'"'"' in a number from 0 to the number of replaceable hydroxide hydrogens, wherein R'"'"' is, independently, H, alkyl, carbonic acid of from 1 to 24 carbon atoms, aromatic phenol substituted with R", heteroaryl ring substituted with R", phenol, (R"-)_x substituted saturated or unsaturated cyclic alcohol, where x is an integer from 0-15,

wherein R" independently is H, F, Cl, Br, I, CN, SCN, NH₂, alkyl, acetyl, acetoxy, acyl, acyloxy and Q₂ PO₄ ;

and

wherein Q is any suitable cation.

5. The composition of claim 1, wherein the organosilane is of the formula I, II, III, or IV:

space="preserve" listing-type="equation">(R.sub.1).sub.3 SiR.sub.2 N.sup.+ (R.sub.3)(R.sub.4)(R.sub.5)Y.sup.-(I)

space="preserve" listing-type="equation">(R.sub.1).sub.3 SiR.sub.2 N(R.sub.3)(R.sub.4) (II)

space="preserve" listing-type="equation">(R.sub.1).sub.3 SiR.sub.2 R.sub.35 (III)

space="preserve" listing-type="equation">(R.sub.1).sub.2 Si(R.sub.36)(R.sub.37) (IV)

wherein;

each R₁ is, independently, halogen, or R₆ O, where R₆ is selected from the group consisting of the following;

H;

alkyl;

acetyl;

acetoxy;

acyl;

acyloxy;

glycol;

polyglycol;

alkyl glycol;

alkyl polyglycol;

a monoester formed by linking a carbonic acid of from 1 to 24 carbons with glycol or poly glycol;

alkyl, phenolics substituted with an alkyl of from 1 to 24 carbons and their ethers and sorbitan esters and their ethers;

R₃₅ is R₆, H, halogen, NH₂ (CH₂)₂ NHR₂, NH₂ R₂, C₃ H₅ O₂ R₂, C₄ H₅ O₂ R₂, NaO(CH₃ O)P(O)R₂, or ClCH₂ C₆ H₄ R₂,

R₃₆ and R₃₇ are, independently, R₃₅, halogen, H, alkyl of from 1 to about 24 carbon atoms, isobutyl, phenyl, or n-octyl;

R₂ is R₆, benzyl, vinyl, or alkyl;

R₃ and R₄ are, independently, R₃₅ alkyl alcohol, alkoxy, or alkyl,

R₅ is alkyl alcohol, R₃₅ CH₂ C₆ H₅, polyglycol, alkyl, alkoxy, perfluoroalkyl, pefluoroalkylsulfonate, or perfluoroalkylcarboxylate, or R₃ and R₄ can, together form a morpholine or cyclic or heterocyclic molecule; and

Y^- is a suitable anionic moiety to form the salt of the compound of formula I, II, III, or IV.

6. The composition of claim 5, wherein R₃ and R₄ together, form a morpholine or cyclic molecule or heterocyclic, unsaturated or saturated, five to seven-membered ring of the formula V:

space="preserve" listing-type="equation">--R.sub.3 --(R.sub.7).sub.k --R.sub.4 -- (V)

wherein;

k is an integer from 0 to 2;

wherein R₇, where the ring is saturated, is CH₂ O, S, NH, NH₂⁺, NCH₂ CH₂ NH₂, NCH₂ CH₂ NH₃⁺, NCH₂ CH₂ N(R₈)(R₉), NCH₂ CH₂ N⁺ (R₈)(R₉)(R₁₀), N(alkyl), N(aryl), N(benzyl);

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

R₇, where the ring is unsaturated, is 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;

wherein the ring is unsubstituted or substituted with an alkyl, ester, aldehyde, carboxylate, amide, thionamide, nitro, amine, or halide;

optionally the ring of formula V represents R₃ or R₄, independently, with the ring nitrogen of formula I or formula II replaced by CH or CH₂ ; and

R₅ is as in claim 5 or a five to seven-membered ring of formula V as described above.

7. The composition of claim 5, wherein R₅ is a five- to seven-membered ring of the following formula:

space="preserve" listing-type="equation">--R.sub.3 --(R.sub.7).sub.k --R.sub.4 -- (V)

wherein;

k is an integer from 0 to 2;

wherein R₇, where the ring is saturated, is CH₂, O, S, NH, NH₂⁺, NCH₂ CH₂ NH₂, NCH₂ CH₂ NH₃⁺, NCH₂ CH₂ N(R₈)(R₉), NCH₂ CH₂ N⁺ (R₈)(R₉)(R₁₀), N(alkyl), N(aryl), N(benzyl);

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

R₇, where the ring is unsaturated, is 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;

wherein the ring is unsubstituted or substituted with an alkyl, ester, aldelyde, carboxylate, amide, thionamide, nitro, amine, or halide; and

optionally the ring of formula V represents R₃ or R₄, independently, with the ring nitrogen of formula I or formula II replaced by CH or CH₂.

8. A water stable composition, comprising the composition of claim 1 and water.

9. The composition of claim 1, wherein the organosilane is 3-(trimethoxysilyl)propyldimethyloctadecyl ammonium chloride.

10. A composition for treating a substrate, comprising a carrier and an effective amount of the composition of claim 1.

11. The composition of claim 10, wherein the carrier is other than water.

12. The composition of claim 1, wherein the organosilane is 3-(trimethoxysilyl)propyldimethyloctadecyl ammonium chloride, 3-(trimethoxysilyl)propylmethyldi(decyl)ammonium chloride, 3-chloropropyltrimethylsilane, 3-chloropropyltrimethoxysilane, octadecyltrimethoxysilane, or perfluorooctyltriethoxysilane.

13. The composition of claim 1, wherein the organosilane is:

(CH₃ O)₃ Si(CH₂)₃ N⁺ (CH₃)₂ C₁₈ H₃₇ Cl^-, (CH₃ O)₃ Si(CH₂)₃ N⁺ (CH₃)₂ C₁₈ H₃₇ Br^-,

(CH₃ O)₃ Si(CH₂)₃ N⁺ (C₁₀ H₂₁)₂ CH₃ Cl^-, (CH₃ O)₃ Si(CH₂)₃ N⁺ (C₁₀ H₂₁)₂ CH₃ Br^-,

(CH₃ O)₃ Si(CH₂)₃ N⁺ (CH₃)₃ Cl^-, (CH₃ O)₃ Si(CH₂)₃ N⁺ (CH₃)₂ C_g H₁₇ Cl^-,

(CH₃ O)₃ Si(CH₂)₃ N⁺ (CH₃)₂ C₁₀ H₂₁ Cl^-, (CH₃ O)₃ Si(CH₂)₃ N⁺ (CH₃)₂ C₁₂ H₂₅ Cl^-,

(CH₃ O)₃ Si(CH₂)₃ N⁺ (CH₃)₂ C₁₄ H₂₉ Cl^-, (CH₃ O)₃ Si(CH₂)₃ N⁺ (CH₃)₂ C₁₆ H₃₃ Cl^-,

(CH₃ O)₃ Si(CH₂)₃ N⁺ (CH₃)₂ C₂₀ H₄₁ Cl^-, (CH₃ O)₃ Si(CH₂)₃ N⁺ (C₄ H₉)₃ Cl^-,

(CH₃ O)₃ Si(CH₂)₃ N⁺ (C₂ H₅)₃ Cl^-, (CH₃ CH₂ O)₃ Si(CH₂)₃ N⁺ (CH₃)₂ C₁₈ H₂₇ Cl^-,

(CH₃ O)₃ Si(CH₂)₃ NHC(O)(CF₂)₆ CF₃, (CH₃ O)₃ Si(CH₂)₃ NHC(O)(CF₂)₈ CF₃,

(CH₃ O)₃ Si(CH₂)₃ NHC(O)(CF₂)₁₀ CF₃, (CH₃ O)₃ Si(CH₂)₃ NHC(O)(CF₂)₁₂ CF₃,

(CH₃ O)Si(CH₂)₃ NHC(O)(CF₂)₁₄ CF₃, (CH₃ O)₃ Si(CH₂)₃ NHC(O)(CF₂)₁₆ CF₃,

(CH₃ O)₃ Si(CH₂)₃ NHSO₂ (CF₂)₇ CF₃,

(CH₃ O)₃ Si(CH₂)₃ N⁺ (CH₃)₂ (CH₂)₃ NHC(O)(CH₂)₆ CH₃,

(CH₃ O)₃ Si(CH₂)₃ N⁺, (CH₃)₂ (CH₂)₃ NHC(O)(CH₂)₈ CH₃,

(CH₃ O)₃ Si(CH₂)₃ N⁺ (CH₃)₂ (CH₂)₃ NHC(O)(CH₂)₁₀ CH₃,

(CH₃ O)₃ Si(CH₂)₃ N⁺ (CH₃)₂ (CH₂)₃ NHC(O)(CH₂)₁₂ CH₃,

(CH₃ O)₃ Si(CH₂)₃ N⁺ (CH₃)₂ (CH₂)₃ NHC(O)(CH₂)₁₄ CH₃,

(CH₃ O)₃ Si(CH₂)₃ N⁺ (CH₃)₂ (CH₂)₃ NHC(O)(CH₂)₁₆ CH₃,

(CH₃ O)₃ Si(CH₂)₃ N⁺ (CH₃)₂ (CH₂)(CH₂)₃ NHC(O)(CF₂)₆ CF₃,

(CH₃ O)₃ Si(CH₂)₃ N⁺ (CH₃)₂ (CH₂)₃ NHC(O)(CF₂)₈ CF₃,

(CH₃ O)₃ Si(CH₂)₃ N⁺ (CH₃)₂ (CH₂)₃ NHC(O)(CF₂)₁₀ CF₃,

(CH₃ O)₃ Si(CH₂)₃ N⁺ (CH₃)₂ (CH₂)₃ NHC(O)(CF₂)₁₂ CF₃,

(CH₃ O)₃ Si(CH₂)₃ N⁺ (CH₃)₂ (CH₂)₃ NHC(O)(CF₂)₁₄ CF₃,

(CH₃ O)₃ Si(CH₂)₃ N⁺ (CH₃)₂ (CH₂)₃ NHC(O)(CF₂)₁₆ CF₃,

(CH₃ O)₃ Si(CH₂)₃ N⁺ (CH₃)₂ (CH₂)₃ NHSO₂ (CF₂)₇ CF₃,

(CH₃ O)₃ Si(CH₂)₃ N⁺ (CH₃)₂ (CH₂)₃ NHSO₂ (CF₂)₉ CF₃,

(CH₃ O)₃ Si(CH₂)₃ N⁺ (CH₃)₂ (CH₂)₃ NHSO₂ (CF₂)₁₁ CF₃,

(CH₃ O)₃ Si(CH₂)₃ N⁺ (CH₃)₂ (CH₂)₃ NHSO₂ (CF₂)₁₃ CF₃,

(CH₃ O)₃ Si(CH₂)₃ N⁺ (CH₃)₂ (CH₂)₃ NHSO₂ (CF₂)₁₅ CF₃,

(CH₃ O)₃ Si(CH₂)₃ N⁺ (CH₃)₂ (CH₂)₃ NHSO₂ (CF₂)₁₆ CF₃,

(CH₃ O)₃ Si(CH₂)₃ NHC₆ H₄ COOH,

(CH₃ O)₃ Si(CH₂)₃ NHC₆ H₄ COOCH₃,

(CH₃ O)₃ Si(CH₂)₃ NHC₆ H₄ COOC₂ H₅,

(CH₃ O)₃ Si(CH₂)₃ NHC₆ H₄ COOC₃ H₇,

(CH₃ O)₃ Si(CH₂)₃ NHC₆ H₄ COOC₄ H₉,

(CH₃ O)₃ Si(CH₂)₃ NHC₆ H₄ COOCH₂ C₆ H₅,

(CH₃ O)₃ Si(CH₂)₃ NHC₆ H₄ COOCH₂ C₆ H₄ NH₂,

(CH₃ O)₃ Si(CH₂)₃ NHC₆ H₄ COOCH₂ C₆ H₄ N(CH₃)₂,

(CH₃ O)₃ Si(CH₂)₃ NHC₆ H₄ COOCH₂ C₆ H₄ N(CH₂ CH₃)₂,

(CH₃ O)₃ Si(CH₂)₃ NHC₆ H₄ COOCH₂ C₆ H₄ N⁺ (CH₃)₃ Y^-,

(CH₃ O)₃ Si(CH₂)₃ NHC₆ H₄ COOCH₂ C₆ H₄ N⁺ (CH₂ CH₃)₃ Y^-,

(CH₃ O)₃ Si(CH₂)₃ NCH₃ C₆ H₄ COOH,

(CH₃ O)₃ Si(CH₂)₃ NCH₃ C₆ H₄ COOCH₃,

(CH₃ O)₃ Si(CH₂)₃ NCH₃ C₆ H₄ COOC₂ H₅,

(CH₃ O)₃ Si(CH₂)₃ NCH₃ C₆ H₄ COOC₃ H₇,

(CH₃ O)₃ Si(CH₂)₃ NCH₃ C₆ H₄ COOC₄ H₉,

(CH₃ O)₃ Si(CH₂)₃ NCH₃ C₆ H₄ COOCH₂ C₆ H₅,

(CH₃ O)₃ Si(CH₂)₃ NCH₃ C₆ H₄ COOCH₂ C₆ H₄ NH₂,

(CH₃ O)₃ Si(CH₂)₃ NCH₃ C₆ H₄ COOCH₂ C₆ H₄ N(CH₃)₂,

(CH₃ O)₃ Si(CH₂)₃ NCH₃ C₆ H₄ COOCH₂ C₆ H₄ N(CH₂ CH₃)₂,

(CH₃ O)₃ Si(CH₂)₃ NCH₃ C₆ H₄ COOCH₂ C₆ H₄ N⁺ (CH₃)₃ Y^-,

(CH₃ O)₃ Si(CH₂)₃ NCH₃ C₆ H₄ COOCH₂ C₆ H₄ N⁺ (CH₂ CH₃)₃ Y^-,

(CH₃ O)₃ Si(CH₂)₃ N⁺ (CH₃)₂ C₆ H₄ COOH Y^-,

(CH₃ O)₃ SI(CH₂)₃ N⁺ (CH₃)₂ C₆ H₄ COOCH₃ Y^-,

(CH₃ O)₃ SI(CH₂)₃ N⁺ (CH₃)₂ C₆ H₄ COOC₂ H₅ Y^-,

(CH₃ O)₃ SI(CH₂)₃ N⁺ (CH₃)₂ C₆ H₄ COOC₃ H₇ Y^-,

(CH₃ O)₃ SI(CH₂)₃ N⁺ (CH₃)₂ C₆ H₄ COOC₄ H₉ Y^-,

(CH₃ O)₃ SI(CH₂)₃ N⁺ (CH₃)₂ C₆ H₄ COOCH₂ C₆ H₅ Y^-,

(CH₃ O)₃ Si(CH₂)₃ N⁺ (CH₃)₂ C₆ H₄ COOCH₂ C₆ H₄ NH₂ Y^-,

(CH₃ O)₃ Si(CH₂)₃ N⁺ (CH₃)₂ C₆ H₄ COOCH₂ C₆ H₄ N(CH₃)₂ Y^-,

(CH₃ O)₃ Si(CH₂)₃ N⁺ (CH₃)₂ C₆ H₄ COOCH₂ C₆ H₄ N(CH₂ CH₃)₂ Y^-,

(CH₃ O)₃ Si(CH₂)₃ N⁺ (CH₃)₂ C₆ H₄ COOCH₂ C₆ H₄ N⁺ (CH₃)₃ Y^- Y^-,

(CH₃ O)₃ Si(CH₂)₃ N⁺ (CH₃)₂ C₆ H₄ COOCH₂ C₆ H₄ N⁺ (CH₂ CH₃)₃ Y^- Y^-,

(CH₃ O)₃ Si(CH₂)₃ NC₂ H₅ C₆ H₄ COOH,

(CH₃ O)₃ Si(CH₂)₃ NC₂ H₅ C₆ H₄ COOCH₃,

(CH₃ O)₃ Si(CH₂)₃ NC₂ H₅ C₆ H₄ COOC₄ H₉,

(CH₃ O)₃ Si(CH₂)₃ NC₂ H₅ C₆ H₄ COOC₃ H₇,

(CH₃ O)₃ Si(CH₂)₃ NC₂ H₅ C₆ H₄ COOC₄ H₉,

(CH₃ O)₃ Si(CH₂)₃ NC₂ H₅ C₆ H₄ COOCH₂ C₆ H₅,

(CH₃ O)₃ Si(CH₂)₃ NC₂ H₅ C₆ H₄ COOCH₂ C₆ H₄ NH₂,

(CH₃ O)₃ Si(CH₂)₃ NC₂ H₅ C₆ H₄ COOCH₂ C₆ H₄ N(CH₃)₂,

(CH₃ O)₃ Si(CH₂)₃ NC₂ H₅ C₆ H₄ COOCH₂ C₆ H₄ N(CH₂ CH₃)₂,

(CH₃ O)₃ Si(CH₂)₃ NC₂ H₅ C₆ H₄ COOCH₂ C₆ H₄ N⁺ (CH₃)₃ Y^-,

(CH₃ O)₃ Si(CH₂)₃ NC₂ H₅ C₆ H₄ COOCH₂ C₆ H₄ N⁺ (CH₂ CH₃)₃ Y^-,

(CH₃ O)₃ Si(CH₂)₃ N⁺ (C₂ H₅)₂ C₆ H₄ COOH Y^-,

(CH₃ O)₃ Si(CH₂)₃ N⁺ (C₂ H₅)₂ C₆ H₄ COOCH₃ Y^-,

(CH₃ O)₃ Si(CH₂)₃ N⁺ (C₂ H₅)₂ C₆ H₄ COOC₂ H₅ Y^-,

(CH₃ O)₃ Si(CH₂)₃ N⁺ (C₂ H₅)₂ C₆ H₄ COOC₃ H₇ Y^-,

(CH₃ O)₃ Si(CH₂)₃ N⁺ (C₂ H₅)₂ C₆ H₄ COOC₄ H₉ Y^-,

(CH₃ O)₃ Si(CH₂)₃ N⁺ (C₂ H₅)₂ C₆ H₄ COOCH₂ C₆ H₅ Y^-,

(CH₃ O)₃ Si(CH₂)₃ N⁺ (C₂ H₅)₂ C₆ H₄ COOCH₂ C₆ H₄ N₂ Y^-,

(CH₃ O)₃ Si(CH₂)₃ N⁺ (C₂ H₅)₂ C₆ H₄ COOCH₂ C₆ H₄ N(CH₃)₂ Y^-,

(CH₃ O)₃ Si(CH₂)₃ N⁺ (C₂ H₅)₂ C₆ H₄ COOCH₂ C₆ H₄ N(CH₂ CH₃)₂ Y^-,

(CH₃ O)₃ Si(CH₂)₃ N⁺ (C₂ H₅)₂ C₆ H₄ COOCH₂ C₆ H₄ N⁺ (CH₃)₃ Y^- Y^-,

(CH₃ O)₃ Si(CH₂)₃ N⁺ (C₂ H₅)₂ C₆ H₄ COOCH₂ C₆ H₄ N⁺ (CH₂ CH₃)₃ Y^- Y^-,

(CH₃ CH₂ O)₃ Si(CH₂)₃ NHC₆ H₄ COOH,

(CH₃ CH₂ O)₃ Si(CH₂)₃ NHC₆ H₄ COOCH₃,

(CH₃ CH₂ O)₃ Si(CH₂)₃ NHC₆ H₄ COOC₂ H₅,

(CH₃ CH₂ O)₃ Si(CH²)₃ NHC₆ H₄ COOC₃ H₇,

(CH₃ CH₂ O)₃ Si(CH₂)₃ NHC₆ H₄ COOC₄ H₉,

(CH₃ CH₂ O)₃ Si(CH₂)₃ NHC₆ H₄ COOCH₂ C₆ H₅,

(CH₃ CH₂ O)₃ Si(CH₂)₃ NHC₆ H₄ COOCH₂ C₆ H₄ NH₂,

(CH₃ CH₂ O)₃ Si(CH₂)₃ NHC₆ H₄ COOCH₂ C₆ H₄ N(CH₃)₂,

(CH₃ CH₂ O)₃ Si(CH₂)₃ NHC₆ H₄ COOCH₂ C₆ H₄ N(CH₂ CH₃)₂,

(CH₃ CH₂ O)₃ Si(CH₂)₃ NHC₆ H₄ COOCH₂ C₆ H₄ N⁺ (CH₃)₃ Y^-,

(CH₃ CH₂ O)₃ Si(CH₂)₃ NHC₆ H₄ COOCH₂ C₆ H₄ N⁺ (CH₂ CH₃)₃ Y^-,

(CH₃ CH₂ O)₃ Si(CH₂)₃ NCH₃ C₆ H₄ COOH,

(CH₃ CH₂ O)₃ Si(CH₂)₃ NCH₃ C₆ H₄ COOCH₃,

(CH₃ CH₂ O)₃ Si(CH₂)₃ NCH₃ C₆ H₄ COOC₂ H₅,

(CH₃ CH₂ O)₃ Si(CH₂)₃ NCH₃ C₆ H₄ COOC₃ H₇,

(CH₃ CH₂ O)₃ Si(CH₂)₃ NCH₃ C₆ H₄ COOC₄ H₉,

(CH₃ CH₂ O)₃ Si(CH₂)₃ NCH₃ C₆ H₄ COOCH₂ C₆ H₅,

(CH₃ CH₂ O)₃ Si(CH₂)₃ NCH₃ C₆ H₄ COOCH₂ C₆ H₄ NH₂,

(CH₃ CH₂ O)₃ Si(CH₂)₃ NCH₃ C₆ H₄ COOCH₂ C₆ H₄ N(CH₃)₂,

(CH₃ CH₂ O)₃ Si(CH₂)₃ NCH₃ C₆ H₄ COOCH₂ C₆ H₄ N(CH₂ CH₃)₂,

(CH₃ CH₂ O)₃ Si(CH₂)₃ NCH₃ C₆ H₄ COOCH₂ C₆ H₄ N⁺ (CH₃)₃ Y^-,

(CH₃ CH₂ O)₃ Si(CH₂)₃ NCH₃ C₆ H₄ COOCH₂ C₆ H₄ N⁺ (CH₂ CH₃)₃ Y^-,

(CH₃ CH₂ O)₃ Si(CH₂)₃ N⁺ (CH₃)₂ C₆ H₄ COOH Y^-,

(CH₃ CH₂ O)₃ Si(CH₂)₃ N⁺ (CH₃)₂ C₆ H₄ C OOCH₃ Y^-,

(CH₃ CH₂ O)₃ Si(CH₂)₃ N⁺ (CH₃)₂ C₆ H₄ COOC₂ H₅ Y^-,

(CH₃ CH₂ O)₃ Si(CH₂)₃ N⁺ (CH₃)₂ C₆ H₄ COOC₃ H₇ Y^-,

(CH₃ CH₂ O)₃ Si(CH₂)₃ N⁺ (CH₃)₂ C₆ H₄ COOC₄ H₉ Y^-,

(CH₃ CH₂ O)₃ Si(CH₂)₃ N⁺ (CH₃)₂ C₆ H₄ COOCH₂ C₆ H₅ Y^-,

(CH₃ CH₂ O)₃ Si(CH₂)₃ N⁺ (CH₃)₂ C₆ H₄ COOCH₂ C₆ H₄ NH₂ Y^-,

(CH₃ CH₂ O)₃ Si(CH₂)₃ N⁺ (CH₃)₂ C₆ H₄ COOCH₂ C₆ H₄ N(CH₃)₂ Y^-,

(CH₃ CH₂ O)₃ Si(CH₂)₃ N⁺ (CH₃)₂ C₆ H₄ COOCH₂ C₆ H₄ N(CH₂ CH₃)₂ Y^-,

(CH₃ CH₂ O)₃ Si(CH₂)₃ N⁺ (CH₃)₂ C₆ H₄ COOCH₂ C₆ H₄ N⁺ (CH₃)₃ Y^- Y^-,

(CH₃ CH₂ O)₃ Si(CH₂)₃ N⁺ (CH₃)₂ C₆ H₄ COOCH₂ C₆ H₄ N⁺ (CH₂ CH₃)₃ Y^- Y^-,

(CH₃ CH₂ O)₃ Si(CH₂)₃ NC₂ H₅ C₆ H₄ COOH,

(CH₃ CH₂ O)₃ Si(CH₂)₃ NC₂ H₅ C₆ H₄ COOCH₃,

(CH₃ CH₂ O)₃ Si(CH₂)₃ NC₂ H₅ C₆ H₄ COOC₂ H₅,

(CH₃ CH₂ O)₃ Si(CH₂)₃ NC₂ H₅ C₆ H₄ COOC₃ H₇,

(CH₃ CH₂ O)₃ Si(CH₂)₃ NC₂ H₅ C₆ H₄ COOC₄ H₉,

(CH₃ CH₂ O)₃ Si(CH₂)₃ NC₂ H₅ C₆ H₄ COOCH₂ C₆ H₅,

(CH₃ CH₂ O)₃ Si(CH₂)₃ NC₂ H₅ C₆ H₄ COOCH₂ C₆ H₄ NH₂,

(CH₃ CH₂ O)₃ Si(CH₂)₃ NC₂ H₅ C₆ H₄ COOCH₂ C₆ H₄ N(CH₃)₂,

(CH₃ CH₂ O)₃ Si(CH₂)₃ NC₂ H₅ C₆ H₄ COOCH₂ C₆ H₄ N(CH₂ CH₃)₂,

(CH₃ CH₂ O)₃ Si(CH₂)₃ NC₂ H₅ C₆ H₄ COOCH₂ C₆ H₄ N⁺ (CH₃)₃ Y^-,

(CH₃ CH₂ O)₃ Si(CH₂)₃ NC₂ H₅ C₆ H₄ COOCH₂ C₆ H₄ N⁺ (CH₂ CH₃)₃ Y^-,

(CH₃ CH₂ O)₃ Si(CH₂)₃ N⁺ (C₂ H₅)₂ C₆ H₄ COOH Y^-,

(CH₃ CH₂ O)₃ Si(CH₂)₃ N⁺ (C₂ H₅)₂ C₆ H₄ COOCH₃ Y^-,

(CH₃ CH₂ O)₃ Si(CH₂)₃ N⁺ (C₂ H₅)₂ C₆ H₄ COOC₂ H₅ Y^-,

(CH₃ CH₂ O)₃ Si(CH₂)₃ N⁺ (C₂ H₅)₂ C₆ H₄ COOC₃ H₇ Y^-,

(CH₃ CH₂ O)₃ Si(CH₂)₃ N⁺ (C₂ H₅)₂ C₆ H₄ COOC₄ H₉ Y^-,

(CH₃ CH₂ O)₃ Si(CH₂)₃ N⁺ (C₂ H₅)₂ C₆ H₄ COOCH₂ C₆ H₅ Y^-,

(CH₃ CH₂ O)₃ Si(CH₂)₃ N⁺ (C₂ H₅)₂ C₆ H₄ COOCH₂ C₆ H₄ NH₂ Y^-,

(CH₃ CH₂ O)₃ Si(CH₂)₃ N⁺ (C₂ H₅)₂ C₆ H₄ COOCH₂ C₆ H₄ N(CH₃)₂ Y^-,

(CH₃ CH₂ O)₃ Si(CH₂)₃ N⁺ (C₂ H₅)₂ C₆ H₄ COOCH₂ C₆ H₄ N(CH₂ CH₃)₂ Y^-,

(CH₃ CH₂ O)₃ Si(CH₂)₃ N⁺ (C₂ H₅)₂ C₆ H₄ COOCH₂ C₆ H₄ N⁺ (CH₃)₃ Y^- Y^-, or

(CH₃ CH₂ O)₃ Si(CH₂)₃ N⁺ (C₂ H₅)₂ C₆ H₄ COOCH₂ C₆ H₄ N⁺ (CH₂ CH₃)₃ Y^- Y^- wherein Y^- or Y^- Y^- is a suitable anionic moiety.

14. The composition of claim 1, wherein the organosilane is:

NH₂ (CH₂)₂ NH(CH₂)₃ Si(OCH₃)₃, NH₂ (CH₂)₃ Si(OCH₃)₃,

NH₂ (CH₂)₃ Si(OCH₂ CH₃)₃, Cl(CH₂)₃ Si(OCH₃)₃, Cl(CH₂)₃ Si(OCH₂ CH₃)₃,

Cl(CH₂)₃ SiCl₃, C₃ H₅ O₂ (CH₂)₃ Si(OCH₃)₃, C₃ H₅ O₂ (CH₂)₃ Si(OCH₂ CH₃)₃,

C₄ H₅ O₂ (CH₂)₃ Si(OCH₃)₃, C₄ H₅ O₂ (CH₂)₃ Si(OCH₂ CH₃)₃, CH₃ SiHCl₂,

NaO(CH₃ O)P(O)(CH₂)₃ Si(OH)₃, SiHCl₃, n-2-vinylbenzylamino-ethyl-3-aminopropyltrimethoxysilane HCL, H₂ C═

CHSi(OCOCH₃)₃, H₂ C═

CHSi(OCH₃)₃,

H₂ C═

CHSi(OCH₂ CH₃)₃, H₂ C═

CHSiCl₃, (CH₃)₂ SiCl₂, (CH₃)₂ Si(OCH₃)₂,

(C₆ H₅)₂ SiCl₂, (C₂ H₅)SiCl₃, (C₂ H₅)Si(OCH₃)₃, (C₂ H₅)Si(OCH₂ CH₃)₃,

isobutyltrimethoxysilane, n-octyltriethoxysilane, CH₃ (C₆ H₅)SiCl₂, CH₃ SiCl₃,

CH₃ Si(OCH₃)₃, C₆ H₅ SiCl₃, C₆ H₅ Si(OCH₃)₃, C₃ H₇ SiCl₃, C₃ H₇ Si(OCH₃)₃, SiCl₄,

ClCH₂ C₆ H₄ CH₂ CH₂ SiCl_3n, ClCH₂ C₆ H₄ CH₂ CH₂ Si(OCH₃)₃,

ClCH₂ C₆ H₄ CH₂ CH₂ Si(OCH₂ CH₃)₃, decyltrichlorosilane, dichloromethyl(4-methylphenethyl)silane, diethoxymethylphenylsilane,

trimethoxysilane, 3-(dimethoxymethylsilyl)-1-propanethiol, dimethoxymethylvinylsilane, 3-propyl methacrylate, trichlorosilane, methylbis(trimethylsilyloxy)vinylsilane, methyltripropoxysilane, or trichlorocyclopentysilane.

15. A composition comprising the organosilane of claim 1 attached to a compound useful for UV protection, wherein said compound is para-amino benzoic acid, amino benzoic acid, salicylic acid, cinnamic acid, benzoic acid, or benzophenone, or akyl derivatives thereof;

optionally, said compound is in anhydride form or mixed anhydride form;

wherein said attachment is a result of removal of one atom or group from said compound and said organosilane, and forming a bond with the free valence produced from said removal.

16. The composition of claim 1 formed from mixing an organosilane of the formula I, II, III, or IV:

space="preserve" listing-type="equation">(R.sub.1).sub.3 SiR.sub.2 N.sup.+ (R.sub.3)(R.sub.4)(R.sub.5)Y.sup.-(I)

space="preserve" listing-type="equation">(R.sub.1).sub.3 SiR.sub.2 N(R.sub.3)(R.sub.4) (II)

space="preserve" listing-type="equation">(R.sub.1).sub.3 SiR.sub.2 R.sub.35 (III)

space="preserve" listing-type="equation">(R.sub.1).sub.2 Si(R.sub.36)(R.sub.37) (IV)

wherein;

each R₁ is, independently, halogen or R₆ O;

wherein R₆ is selected from the group consisting of the following;

H;

alkyl;

acetyl;

acetoxy;

acyl;

acyloxy;

glycol;

polyglycol;

alkyl glycol;

alkyl polyglycol;

a monoester formed by linking a carbonic acid of from 1 to 24 carbons with glycol or polyglycol;

phenolics substituted with an alkyl of from 1 to 24 carbons;

phenolics substituted with ethers of from 1 to 24 carbons;

sorbitan esters and their ethers; and

polyalkylether;

R₃₅ is R₆, H, halogen, NH₂ (CH₂)₂ NHR₂, NH₂ R₂, C₃ H₅ O₂ R₂, C₄ H₅ O₂ R₂, NaO(CH₃ O)P(O)R₂, or ClCH₂ C₆ H₄ R₂ ;

R₃₆ and R₃₇ are, independently, R₃₅, halogen, H, alkyl of from 1 to about 8 carbon atoms, acrylic, vinyl, acetylenic, benzyl, styryl, propenyl, isobutyl, phenyl, or n-octyl;

R₂ is benzyl, vinyl or alkyl;

R₃ and R₄ are, independently, lower alkyl alcohol, lower alkoxy of from 1 to 4 carbon atoms, or alkyl;

R₅ is lower alkyl alcohol, CH₂ C₆ H₅, poly glycol, alkyl, alkoxy, perfluoroalkyl, pefluoroalkylsulfonate, perfluoroalkylcarboxylate;

or R₃ and R₄ can, together, form a morpholine or cyclic molecule or heterocyclic molecule; and

Y^- is a suitable anionic moiety to form the salt of the compound of formula I, II, III or IV;

with an ether having the formula R--O--R, wherein R is, independently, an organic group, and the ether has a hydroxy functionality or a carboxylic ester functionality.

17. The composition of claim 16, wherein R₃ and R₄ together, form a morpholine or cyclic or heterocyclic, unsaturated or saturated, five to seven-membered ring of the formula V:

space="preserve" listing-type="equation">--R.sub.3 --(R.sub.7).sub.k --R.sub.4 -- (V)

wherein k is an integer from 0 to 2;

wherein R₇, where the ring is saturated, is CH₂, O, S, NH, NH₂⁺, NCH₂ CH₂ NH₂, NCH₂ CH₂ NH₃⁺, NCH₂ CH₂ N(R₈)(R₉), NCH₂ CH₂ N⁺ (R₈)(R₉)(R₁₀), N(alkyl), N(aryl), N(benzyl);

wherein each R₈, R₉, and R₁₀ is, independently, benzyl, polyglycol, lower alkyl alcohol of from 1 to 4 carbon atoms, lower alkoxy of from 1 to 4 carbon atoms, or alkyl of from 1 to 22 carbon atoms; and

R₇, where the ring is unsaturated, is 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;

wherein the ring is unsubstituted or substituted with alkyl of from 1 to 22 carbon atoms, ester, aldehyde, carboxylate, amide, thionamide, nitro, amine, or halide;

optionally, the ring, of formula V represents R₃ and R₄, independently, with the ring nitrogen of formula I or formula II replaced by CH or CH2; and

R₅ is as in claim 15 or a five to seven-membered ring according to formula V as described above.

18. The composition of claim 16, wherein R₅ is a five- to seven-membered ring of the following formula:

space="preserve" listing-type="equation">--R.sub.3 --(R.sub.7).sub.k --R.sub.4 -- (V)

wherein;

k is an integer from 0 to 2;

wherein R₇, where the ring is saturated, is CH₂, O, S, NH, NH₂⁺, NCH₂ CH₂ NH₂, NCH₂ CH₂ NH₃⁺, NCH₂ CH₂ N(R₈)(R₉), NCH₂ CH₂ N⁺ (R₈)(R₉)(R₁₀), N(alkyl), N(aryl), N(benzyl);

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

R₇, where the ring is unsaturated, is 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;

wherein the ring is unsubstituted or substituted with an alkyl, ester, aldehyde, carboxylate, amide, thionamide, nitro, amine, or halide; and

optionally the ring of formula V represents R₃ or R₄, independently, with the ring nitrogen of formula I or formula II replaced by CH or CH₂.

19. The composition of claim 16 which is an aqueous composition.

20. A method of treating a substrate, comprising contacting the substrate with a sufficient amount of the composition of claim 1 for a period of time sufficient for treatment of the substrate.

31. The composition of claim 1 capable of providing a durable antimicrobial treatment having a zone of inhibition after drying.

21. A method of dyeing a substrate, comprising contacting the substrate with an aqueous composition comprising an aqueous soluble dye suitable for dyeing a substrate and the composition formed from mixing:

a) an organosilane of the formula R_n SiX_4-n where n is an integer of from 0 to 3;

each R is, independently, a nonhydrolyzable organic group; and

each X is, independently, a hydrolyzable group;

with

b) an ether of the formula R--O--R, wherein R is, independently, an organic group, and the ether has either a hydroxy functionality or a carboxylic ester functionality.

22. A method of antimicrobially treating a food article, comprising contacting the food article with an effective amount of the product formed from mixing:

a) an antimicrobial organosilane of the formula R_n SiX_4-n where n is an integer of from 0 to 3;

each R is, independently, a nonhydrolyzable organic group; and

each X is, independently, a hydrolyzable group;

with

b) an ether of the formula R--O--R, wherein R is, independently, an organic group, and the ether has either a hydroxy functionality or a carboxylic ester functionality.

23. A method of antimicrobially coating a fluid container used for containing a human or animal consumable product, comprising contacting the container with an effective amount of the product formed from mixing:

a) an antimicrobial organosilane of the formula R_n SiX_4-n where n is an integer of from 0 to 3;

each R is, independently, a nonhydrolyzable organic group; and

each X is, independently, a hydrolyzable group;

with

b) an ether of the formula R--O--R, wherein R is, independently, an organic group, and the ether has either a hydroxy functionality or a carboxylic ester functionality.

25. The method of claim 23, wherein the article is a surgical glove.

24. A method of antimicrobially coating a latex medical article for use in a human or animal medical procedure, comprising contacting the article with an effective amount of the product formed from mixing:

a) an antimicrobial organosilane of the formula R_n SiX_4-n where n is an integer of from 0 to 3;

each R is, independently, a nonhydrolyzable organic group; and

each X is, independently, a hydrolyzable group;

with

b) an ether of the formula R--O--R, wherein R is, independently, an organic group, and the ether has either a hydroxy functionality or a carboxylic ester functionality.

26. A method of antimicrobially treating a substrate selected from the group consisting of a concrete pipe, 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, a PE, PP or polyester plastic cover, a silicone or TEFLON®

coated fiberglass article, a Dryvitt finish, a stucco finish, blended cotton, a bio-film, a bio-adhesive, single ply roofing, a roofing shingle, carpet, a paper product, teeth, skin, bone, cartilage, a metal finish, a car finish, and a fiberglass reinforcement product, comprising contacting the substrate with an effective amount of the composition formed from mixing;

a) an antimicrobial organosilane of the formula R_n SiX_4-n where n is an integer of from 0 to 3;

each R is, independently, a nonhydrolyzable organic group; and

each X is, independently, a hydrolyzable group, with

b) an ether of the formula R--O--R, wherein R is, independently, an organic group, and the ether has either a hydroxy functionality or a carboxylic ester functionality.

27. A method of antimicrobially enhancing a product of rubbing alcohol, a flower preservative, or a waterproofing solution, comprising admixing with the product an effective amount of the composition formed from mixing:

a) an antimicrobial organosilane of the formula R_n SiX_4-n where n is an integer of from 0 to 3;

each R is, independently, a nonhydrolyzable organic group; and

each X is, independently, a hydrolyzable group;

with

b) an ether of the formula R--O--R, wherein R is, independently, an organic group, and the ether has either a hydroxy functionality or a carboxylic ester functionality.

28. A method for making an organosilane of the formula R_n SiX_4-n where n is an integer of from 0-3, preferably 0-2;

each R is, independently, a nonhydrolyzable organic group; and

each X is, independently, a hydrolyzable group;

which comprises mixing the organosilane synthesis starting materials in an aqueous solution in the presence of an ether of the formula R--O--R wherein R is, independently, an organic group, and the ether has either a hydroxy functionality or a carboxylic ester functionality.

29. A water-stable composition comprising from about 0.001% to about 14% organosilane and from about 0.001% to about 14% of an ether having the formula R--O--R, wherein R is an organic group, and the ether has either a hydroxy or carboxylic acid ester functionality, and 99.9 to 60% water;

wherein percentages are the weight percent of said composition.

30. The composition of claim 29 wherein the ether is glycol ether DB, tripropylene glycol methyl ether, diethylene glycol methyl ether, tripropylene glycol butyl ether, dipropylene glycol butyl ether, propylene glycol butyl ether, phenol, ethoxylated phenol, ethoxylated octylphenol, ethoxylated nonylphenol, ethoxylated sorbitan esters, or glycol ether EB.