Water-stabilized organosilane compounds and methods for using the same

• US 5,954,869 A
• Filed: 05/07/1997
• Issued: 09/21/1999
• Est. Priority Date: 05/07/1997
• 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): Marquis, Melvyn I.
• Assistant Examiner(s): Milstead, Mark W.
• Application Number:
  US08/852,474
• Time in Patent Office: 867 Days
• Field of Search: 528/25, 528/38, 528/29, 536/56, 536/84, 536/111, 536/123.1, 106/14.11, 106/287.16
• US Class Current: 106/287.16
• CPC Class Codes: C07F 7/1804 Compounds having Si-O-C linkages Si-O-acyl linkages C07F7/1896

Abstract

The composition formed by mixing an organosilane, optionally having a nonhydrolizable organic group, but having one or more hydrolyzable groups, with a polyol containing at least two hydroxy groups, wherein at least any two of the hydroxy groups are separated by no more than two intervening atoms. Water-stabilized organosilane compounds. A water stable composition made from the polyol and organosilane or compound 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. A method of making a siloxane in the presence of a stabilizer.

Claims

1. A composition comprising:

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

R is, independently, a nonhydrolizable organic group; and

each X is, independently, a hydrolyzable group;

b) a polyol containing at least two hydroxy groups, wherein at least two of the at least two hydroxy groups are separated by less than three intervening atoms; and

c) water

wherein said organosilane amounts to about 20% or less by weight of said composition.

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

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.-(II)

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

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

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

wherein

each R₁ is, independently, halogen or R₆ O, where R₆ is H, alkyl of from 1 to about 22 carbon atoms, acetyl, acetoxy, acyl, propylene glycol, ethylene glycol, polyethylene glycol, polypropylene glycol;

block and copolymers of ethylene and propylene glycol, the alkyl monoether of from 1 to 22 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 of from 1 to 22 carbons and propylene glycol, ethylene glycol, polyethylene glycol, polypropylene glycol;

block and copolymers of ethylene and propylene glycol;

octyphenol;

nonylphenol;

or sorbitan ethers;

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

R₃₆ and R₃₇ are, independently, halogen, H, alkyl of from 1 to about 22 carbon atoms, acrylic, vinyl, acetylenic, benzyl, styryl, propinyl, isobutyl, phenyl, or n-octyl;

R₂ is benzyl, vinyl or alkyl of from 1 to about 22 carbon atoms;

R₃ and R₄ are, independently, lower alkyl alcohol, lower alkoxy of from 1 to 4 carbon atoms, alkyl of from 1 to about 22 carbon atoms;

or R₃ and R₄ can, together, form a morpholine or cyclic or heterocyclic, unsaturated or saturated, five to seven-membered ring of the formula VI;

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

where k is an integer from 0 to 2,

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), where each R₈, R₉, and R₁₀ is, independently, benzyl, polyether, 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 about 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;

R₅ is lower alkyl alcohol, CH₂ C₆ H₅, polyether, alkyl, alkoxy, perfluoroalkyl, pefluoroalkylsulfonate, or perfluoroalkylcarboxylate wherein the alkyl, alkoxy, perfluoroalkyl, perfluoroalkylsulfonate, or perfluoroalkylcarboxylate is of from 1 to about 22 carbon atoms, or is a five to seven-membered ring of formula VI as described above; and

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

3. The composition of claim 1, wherein the organosilane is 3-(trimethoxysilyl)propyldimethyloctadecyl ammonium chloride and the polyol is glucose, sucrose, fructose, mannitol, ascorbic acid and optionally including an anti-oxidant, adenosine, glucuronic acid, glucurone, dextrose, cellulose, partially hydrolyzed cellulose, soluble starch, a starch-acrylic acid graft copolymer, a nucleoside, a nucleotide, an oligonucleotide, or a polynucleotide.

4. 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)_g 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⁺ (CH₂ 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 COOCH₃ 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⁺ (CH₂ 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 H ₅)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^-.

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

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.-(II)

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

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

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

wherein

each R₁ is, independently, halogen or R₆ O, where R₆ is H, alkyl of from 1 to about 22 carbon atoms, acetyl, acetoxy, acyl, propylene glycol, ethylene glycol, polyethylene glycol, polypropylene glycol;

block and copolymers of ethylene and propylene glycol, the alkyl monoether of from 1 to 22 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 of from 1 to 22 carbons and propylene glycol, ethylene glycol, polyethylene glycol, polypropylene glycol;

block and copolymers of ethylene and propylene glycol;

octyphenol;

nonylphenol;

or sorbitan ethers;

R₃₅ is H, halogen, NH₂ (CH₂)₂ NH, NH₂, C₃ H₅ O₂, C₃ H₅ O₂, NaO(CH₃ O)P(O), or CICl₂ C₆ H₄ ;

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

R₂ is benzyl, vinyl or alkyl of from 1 to about 22 carbon atoms;

R₃ and R₄ are, independently, lower alkyl alcohol, lower alkoxy of from 1 to 4 carbon atoms, alkyl of from 1 to about 22 carbon atoms;

or R₃ and R₄ can, together, form a morpholine or cyclic or heterocyclic, unsaturated or saturated, five to seven-membered ring of the formula VI;

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

where k is an integer from 0 to 2,

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), where each R₈, R₉, and R₁₀ is, independently, benzyl, polyether, 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 about 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

R₅ is lower alkyl alcohol, CH₂ C₆ H₅, polyether, alkyl, alkoxy, perfluoroalkyl, pefluoroalkylsulfonate, or perfluoroalkylcarboxylate wherein the alkyl, alkoxy, perfluoroalkyl, pefluoroalkylsulfonate, or perfluoroalkylcarboxylate is from 1 to about 22 carbon atoms or is a five to seven-membered ring according to formula VI as described above; and

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

with a polyol containing at least two hydroxy groups, wherein any two of the at least two hydroxy groups are separated by no more than two intervening atoms.

6. 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.

7. 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 and the polyol is selected from the group consisting of (a) an aldose, ketose, or aldose or ketose oxidized or reduced in a single step;

(b) substituted aldose, substituted ketose, or substituted aldose or substituted ketose oxidized or reduced in a single step;

(c) a polymer of aldose, a polymer of ketose, a polymer of aldose and ketose, or any thereof oxidized or reduced in a single step; and

(d) a substituted polymer of aldose, a substituted polymer of ketose, a substituted polymer of aldose and ketose, or ant thereof oxidized or reduced in a single step.