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1. US6632805 - Methods for using water-stabilized organosilanes

Note: Texte fondé sur des processus automatiques de reconnaissance optique de caractères. Seule la version PDF a une valeur juridique

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What is claimed is:

1. A method of antimicrobially treating a food article, comprising contacting the food article with an effective amount of a water stable composition comprising water and a product that is formed by reacting in water:
a) an organosilane of the formula R nSiX 4−n where n is an integer of from 0 to 3; each R is, independently, a nonhydrolizable organic group; and each X is, independently, a hydrolyzable group, with
b) a polyol containing at least three hydroxy groups, wherein all of the hydroxy groups are separated by at least three intervening atoms,
wherein the polyol is not hydroxyethyl cellulose,
wherein the product is a monomer, oligomer, or a combination thereof,
for a period of time sufficient to antimicrobially treat the food article.
 
2. 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 a water stable composition comprising water and a product that is formed by reacting in water:
a) an organosilane of the formula R nSiX 4−n where n is an integer of from 0 to 3; each R is, independently, a nonhydrolizable organic group; and each X is, independently, a hydrolyzable group, with
b) a polyol containing at least three hydroxy groups, wherein all of the hydroxy groups are separated by at least three intervening atoms,
wherein the polyol is not hydroxyethyl cellulose,
wherein the product is a monomer, oligomer, or a combination thereof,
for a period of time sufficient to antimicrobially coat the container.
 
3. 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 a water stable composition comprising water and a product that is formed by reacting in water:
a) an organosilane of the formula R nSiX 4−n where n is an integer of from 0 to 3; each R is, independently, a nonhydrolizable organic group; and each X is, independently, a hydrolyzable group, with
b) a polyol containing at least three hydroxy groups, wherein all of the hydroxy groups are separated by at least three intervening atoms,
wherein the polyol is not hydroxyethyl cellulose,
wherein the product is a monomer, oligomer, or a combination thereof,
for a period of time sufficient to antimicrobially coat the article.
 
4. The method of claim 3, wherein the article is a surgical glove.
 
5. 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 a water stable composition comprising water and a product that is formed by reacting in water:
a) an organosilane of the formula R nSiX 4−n where n is an integer of from 0 to 3; each R is, independently, a nonhydrolizable organic group; and each X is, independently, a hydrolyzable group, with
b) a polyol containing at least three hydroxy groups, wherein all of the hydroxy groups are separated by at least three intervening atoms,
wherein the polyol is not hydroxyethyl cellulose,
wherein the product is a monomer, oligomer, or a combination thereof,
for a period of time sufficient to antimicrobially enhance the product.
 
6. 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, an HDP plastic cover, a stucco finish, blended cotton, a bio-film, a bio-adhesive, a single ply roofing, a roofing shingle, and a fiberglass reinforcement product, comprising contacting the substrate with an effective amount of a water stable composition comprising water and a product that is formed by reacting in water:
a) an organosilane of the formula R nSiX 4−n where n is an integer of from 0 to 3; each R is, independently, a nonhydrolizable organic group; and each X is, independently, a hydrolyzable group, with
b) a polyol containing at least three hydroxy groups, wherein all of the hydroxy groups are separated by at least three intervening atoms,
wherein the polyol is not hydroxyethyl cellulose,
wherein the product is a monomer, oligomer, or a combination thereof,
for a period of time sufficient to antimicrobially treat the substrate.
 
7. The method of claim 6, wherein n is an integer from 0 to 2; each R is, independently, alkyl, alkyl alcohol, or aromatic; each X is, independently, hydroxy, alkoxy, halogen, acetyl, acetoxy, acyl, a hydroxylated solid or liquid polymeric moiety, polyether or polyalkylether; and wherein the polyol is of the formula I:{R11(W)p}(R33)3−oC{(CH2)qOH}o  (I) {R11(W)p}(R33)3−oC{(CH2)qOH}o  (I) wherein
o is an integer of from 2 to 3;
q is an integer of from 1 to 2;
p is an integer of from 0 to 1;
W is alkyl, polyether, aryl or heteroaryl;
R 11 and R 33 are, independently, halogen, H, CH 2OH, N(CH 2CH 2OH) 2CH 3 +V , NH 2, NO 2, N(H)(CH 2) 3OSO 3H, N +(CH 3) 2(CH 2) 3SO 3 , N(CH 3) 3 +V , (CH 2)OPO 3, H 2(CH 2)PO 3H 2,
N(H)R 34(CF 2) eCF 3 where e is an integer of from 1 to about 22 and R 34 is CO or SO 2,
(W) pOZ a where Z a is H, alkyl, aryl; or heteroaryl,
(W) pS(O) rZ b where Z b is H, Na, a suitable mono- or di-valent cation, alkyl, aryl, or heteroaryl and r is an integer from 0 to 2,
(W) pNZ 1Z 2 where Z 1 and Z 2 are, independently, H, alkyl, aryl, or heteroaryl,
(W) pN +Z 3Z 4Z 5Q where Z 3, Z 4, and Z 5 are, independently, H, alkyl, aryl, or heteroaryl, or
(W) pPO 3Z 6 where Z 6 is H, Na, a suitable mono- or di-valent cation, alkyl, aryl, or heteroaryl; and
V is a suitable anionic moiety to form the salt of the compound of formula I, and
Q is a suitable anionic moiety to form the salt of the compound of formula I.
 
8. The method of claim 7, wherein V and Q are halide, sulfate, tosylate, carboxylate, polycarboxylate, alkyl, arylsulfonate, phosphate, phosphonate, borate, or boronate.
 
9. The method of claim 7, wherein W is alkyl of from 1 to 22 carbon atoms.
 
10. The method of claim 7, wherein W is alkyl of from 1 to 10 carbon atoms.
 
11. The method of claim 7, wherein W is alkyl of from 1 to 3 carbon atoms.
 
12. The method of claim 6, wherein the organosilane is (CH3O)3Si(CH2)3N+(CH3)2C18H37Br, (CH3O)3Si(CH2)3N+(CH3)2C18H37Cl, (CH3O)3Si(CH2)3N+(C10H21)2CH3Cl, (CH3O)3Si(CH2)3N+(C10H21)2CH3Br, (CH3O)3Si(CH2)3N+(CH3)3Cl, (CH3O)3Si(CH2)3N+(CH3)2C8H17Cl, (CH3O)3Si(CH2)3N+(CH3)2C10H21Cl, (CH3O)3Si(CH2)3N+(CH3)2C12H25Cl, (CH3O)3Si(CH2)3N+(CH3)2C14H29Cl, (CH3O)3Si(CH2)3N+(CH3)2C16H33Cl, (CH3O)3Si(CH2)3N+(CH3)2C20H41Cl, (CH3O)3Si(CH2)3N+(C4H9)3Cl, (CH3O)3Si(CH2)3N+(C2H5)3Cl, (CH3CH2O)3Si(CH2)3N+(CH3)2C18H27Cl, (CH3O)3Si(CH2)3NHC(O)(CF2)6CF3, (CH3O)3Si(CH2)3NHC(O)(CF2)8CF3, (CH3O)3Si(CH2)3NHC(O)(CF2)10CF3, (CH3O)3Si(CH2)3NHC(O)(CF2)12CF3, (CH3O)3Si(CH2)3NHC(O)(CF2)14CF3, (CH3O)3Si(CH2)3NHC(O)(CF2)16CF3, (CH3O)3Si(CH2)3NHSO2(CF2)7CF3, (CH3O)3Si(CH2)3N+(CH3)2(CH2)3NHC(O)(CH2)6CH3, (CH3O)3Si(CH2)3N+(CH3)2(CH2)3NHC(O)(CH2)8CH3, (CH3O)3Si(CH2)3N+(CH3)2(CH2)3NHC(O)(CH2)10CH3, (CH3O)3Si(CH2)3N+(CH3)2(CH2)3NHC(O)(CH2)12CH3, (CH3O)3Si(CH2)3N+(CH3)2(CH2)3NHC(O)(CH2)14CH3, (CH3O)3Si(CH2)3N+(CH3)2(CH2)3NHC(O)(CH2)16CH3, (CH3O)3Si(CH2)3N+(CH3)2(CH2)3NHC(O)(CF2)6CF3, (CH3O)3Si(CH2)3N+(CH3)2(CH2)3NHC(O)(CF2)8CF3, (CH3O)3Si(CH2)3N+(CH3)2(CH2)3NHC(O)(CF2)10CF3, (CH3O)3Si(CH2)3N+(CH3)2(CH2)3NHC(O)(CF2)12CF3, (CH3O)3Si(CH2)3N+(CH3)2(CH2)3NHC(O)(CF2)14CF3, (CH3O)3Si(CH2)3N+(CH3)2(CH2)3NHC(O)(CF2)16CF3, (CH3O)3Si(CH2)3N+(CH3)2(CH2)3NHSO2(CF2)7CF3, (CH3O)3Si(CH2)3N+(CH3)2(CH2)3NHSO2(CF2)9CF3, (CH3O)3Si(CH2)3N+(CH3)2(CH2)3NHSO2(CF2)11CF3, (CH3O)3Si(CH2)3N+(CH3)2(CH2)3NHSO2(CF2)13CF3, (CH3O)3Si(CH2)3N+(CH3)2(CH2)3NHSO2(CF2)15CF3, or (CH3O)3Si(CH2)3N+(CH3)2(CH2)3NHSO2(CF2)16CF3.
 
13. The method of claim 6, wherein the organosilane is NH2(CH2)2NH(CH2)3Si(OCH3)3, NH2(CH2)3Si(OCH3)3, NH2(CH2)3Si(OCH2CH3)3, Cl(CH2)3Si(OCH3)3, Cl(CH2)3Si(OCH2CH3)3, Cl(CH2)3SiCl3, CH3CH2C(O)O—(CH2)3Si(OCH3)3, CH3CH2C(O)O—(CH2)3Si(OCH2CH3)3, H2C═C(CH3)C(O)O—(CH2)3Si(OCH3)3, H2C═C(CH3)C(O)O—(CH2)3Si(OCH2CH3)3, CH3SiHCl2, NaO(CH3O)P(O)(CH2)3Si(OH)3, SiHCl3, H2C═CHSi(OCOCH3)3, H2C═CHSi(OCH3)3, H2C═CHSi(OCH2CH3)3, H2C═CHSiCl3, (CH3)2SiCl2, (CH3)2Si(OCH3)2, (C6H5)2SiCl2, (C2H5)SiCl3, (C2H5)Si(OCH3)3, (C2H5)Si(OCH2CH3)3, isobutyltrimethoxysilane, n-octyltriethoxysilane, CH3(C6H5)SiCl2, CH3SiCl3, CH3Si(OCH3)3, C6H5SiCl3, C6H5Si(OCH3)3, C3H7SiCl3, C3H7Si(OCH3)3, SiCl4, ClCH2C6H4CH2CH2SiCl3, ClCH2C6H4CH2CH2Si(OCH3)3, ClCH2C6H4CH2CH2Si(OCH2CH3)3, (decyl)(trichloro)silane, (dichloro)(methyl)(4-methylphenethyl)silane, (diethoxy)(methyl)(phenyl)silane, {3-(diethylamino)propyl}(trimethoxy)silane, {3-(dimethoxy)(methyl)silyl}-1-propanethiol, (dimethoxy)(methyl)(vinyl)silane, 3-{tris(trimethylsilyloxy)silyl}propyl methacrylate, (trichloro){4-(chloromethyl)phenyl}silane, (methyl){bis(trimethylsilyloxy)}(vinyl)silane, (methyl)(tripropoxy)silane, or (trichloro)(cyclopentyl)silane.
 
14. The method of claim 6, wherein the polyol is a compound having the formula VII:(R12)(R13)C{(CH2)sR14}2  (VII) (R12)(R13)C{(CH2)sR14}2  (VII) wherein
s is an integer of from 1 to 2;
R 12 is (CH 2) gR 14 where g is an integer of from 0 to 10, lower alkyl of from 1 to about 4 carbon atoms, lower alkoxy of from 1 to about 4 carbon atoms, N(R 15)(R 16), N(H)(CH 2) 3OSO 3H, N(H)(CH 2) 3OSO 3H, N(H)(CH 2) 3OSO 3H, N +(CH 3) 2(CH 2SO 3 , N +(CH 3) 3T , or N +(R 17)(R 18)(R 19)T , where
R 15, R 16, R 17, and R 18 are, independently, H, O, or lower alkyl of from 1 to about 4 carbon atoms, polyalkyl ester, benzyl, or
R 15 and R 16, together, or R 17 and R 18, together, may, independently, form an amide, sulfonamide, phosphonamide, oxime, thionamide, quaternary ammonium, imine, imide, guanidine, piperazine, morpholine, or N(O)R 20R 21, where R 20 and R 21 are,
independently, 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 4 carbon atoms;
R 19 is H or alkyl of from 1 to about 22 carbon atoms; and
T is a suitable anionic moiety;
R 13 is H, OH, (CH 2) sR 14, (CH 2)OPO 3H 2, or (CH 2)PO 3H 2, lower alkyl of from 1 to 4 carbon atoms, lower alkoxy of from 1 to about 4 carbon atoms; and
each R 14 is, independently, OH or {—CH 2C(CH 2OH) 2CH 2O} j—H where j is an integer of from 0 to 5;
or a perfluoro- analog thereof.
 
15. The method of claim 14, wherein g is an integer of from 0 to 3; R12 is (CH2)gR14, lower alkyl of from 1 to about 4 carbon atoms, lower alkoxy of from 1 to about 4 carbon atoms, N(R15)(R16), N(H)(CH2)3OSO3H, N(H)(CH2)3OSO3H, N(H)(CH2)3OSO3H, N+(CH3)2(CH2)3SO3, N+(CH3)3T, or N+(R17)(R18)(R19)T;
R 13 is H, OH, (CH 2) sR 14, (CH 2)OPO 3H 2, or (CH 2)PO 3H 2, lower alkyl of from 1 to 4 carbon atoms, lower alkoxy of from 1 to about 4 carbon atoms, and
each R 14 is, independently, OH or {—CH 2C(CH 2OH) 2CH 2O} j—H where j is an integer of from 0 to 5.
 
16. The method of claim 14, wherein R12 is (CH2)gR14, lower alkyl of from 1 to about 4 carbon atoms, or lower alkoxy of from 1 to about 4 carbon atoms.
 
17. The method of claim 14, wherein R12 is N(R15)(R16), N(H)(CH2)3OSO3H, N(H)(CH2)3OSO3H, N(H)(CH2)3OSO3H, N+(CH3)2(CH2)3SO3, N+(CH3)3T, or N+(R17)(R18)(R19)T.
 
18. The method of claim 14, wherein g is an integer of from 0 to 3; R12 is (CH2)g14, lower alkyl of from 1 to about 4 carbon atoms, lower alkoxy of from 1 to about 4 carbon atoms, N(R15)(R16), N(H)(CH2)3OSO3H, N(H)(CH2)3OSO3H, N(H)(CH2)3OSO3H, N+(CH3)2(CH2)3SO3, N+(CH3)3T, or N+(R17)(R18)(R19)T; and each R14 is OH.
 
19. The method of claim 14, wherein g is an integer of from 0 to 3; R12 is (CH2)gR14, lower alkyl of from 1 to about 4 carbon atoms, lower alkoxy of from 1 to about 4 carbon atoms, N(R15)(R16), N(H)(CH2)3OSO3H, N(H)(CH2)3OSO3H, N(H)(CH2)3OSO3H, N+(CH3)2(CH2)3SO3, N+(CH3)3T, or N+(R17)(R18)(R19)T; and each R14 is, independently, {—CH2C(CH2OH)2CH2O}j—H where j is an integer of from 0 to 5.
 
20. The method of claim 6, wherein the polyol is aryl substituted with from 2 to 6 moieties of —(OCH2)C(CH2OH)3.
 
21. The method of claim 6, wherein the polyol is pentaerythritol, dipentaerythritol, tripentaerythritol, tetrapentaerythritol, tris(hydroxymethyl)ethane, tris(hydroxymethyl)propane, tris(hydroxymethyl)nitromethane, tris(hydroxymethyl)aminomethane, tris(hydroxymethyl)methane trimethyl ammonium iodide, or tetrakis(hydroxymethyl)phosphonium chloride.
 
22. The method of claim 6, wherein the organosilane is of the formula II, III, IV, or V:(R1)3SiR2N+(R3)(R4)(R5)Y  (II) (R1)3SiR2N+(R3)(R4)(R5)Y  (II) (R1)3SiR2N(R3)(R4)  (III) (R1)3SiR2N(R3)(R4)  (III) (R1)3SiR2—R35  (IV) (R1)3SiR2—R35  (IV) (R1)2Si(R36)(R37)  (V) (R1)2Si(R36)(R37)  (V) wherein
each R 1 is, independently, halogen or R 6O, where R 6 is H, alkyl of from 1 to about 6 carbon atoms, acetyl, acetoxy, or acyl;
R 35 is H, halogen, NH 2(CH 2) 2NHR 2, NH 2R 2, CH 3CH 2C(O)OR 2, H 2C═C(CH 3)C(O)OR 2, NaO(CH 3O)P(O)R 2, or ClCH 2C 6H 4R 2;
R 36 and R 37 are, independently, halogen, H, alkyl of from 1 to about 8 carbon atoms, isobutyl, phenyl, or n-octyl;
R 2 is benzyl, vinyl or alkyl of from 1 to about 3 carbon atoms;
R 3 and R 4 are, independently, lower alkyl alcohol, lower alkoxy of from 1 to 4 carbon atoms, alkyl of from 1 to about 22 carbon atoms; or
R 3 and R 4 can, together, form a morpholine or cyclic or heterocyclic, unsaturated or saturated, five to seven-membered ring;
R 5 is lower alkyl alcohol, CH 2C 6H 5, polyether, alkyl, alkoxy, perfluoroalkyl, perfluoroalkylsulfonate, or perfluoroalkylcarboxylate wherein the alkyl, alkoxy, perfluoroalkyl, perfluoroalkylsulfonate, or perfluoroalkylcarboxylate is of from 1 to about 22 carbon atoms; and
Y is a suitable anionic moiety to form the salt of the compound of formula II, III, IV or V;
and where the polyol is of the formula I:
{R11(W)p}(R33)3−oC{(CH2)qOH}o  (I) {R11(W)p}(R33)3−oC{(CH2)qOH}o  (I) wherein
o is an integer of from 2 to 3;
q is an integer of from 1 to 2;
p is an integer of from 0 to 1;
W is alkyl, polyether, aryl or heteroaryl;
R 11 and R 33 are, independently, halogen, H, CH 2OH,
N(CH 2CH 2OH) 2CH 3 +V , NH 2, NO 2, N(H)(CH 2) 3OSO 3H, N +(CH 3) 2(CH 2) 3SO 3 ,
N(CH 3) 3 +V , (CH 2)OPO 3H 2, (CH 2)PO 3H 2, N(H)R 34(CF 2) eCF 3 where e is an integer of from 1 to about 22 and R 34 is CO or SO 2,
N(H)R 34(CF 2) eCF 3 where e is an integer of from 1 to about 22 and R 34 is CO or SO 2,
(W) pOZ a where Z a is H, alkyl, aryl, or heteroaryl,
(W) pS(O) rZ b where Z b is H, Na, a suitable mono- or di-valent cation, alkyl, aryl, or heteroaryl and r is an integer from 0 to 2,
(W) pNZ 1Z 2 where Z 1 and Z 2 are, independently, H, alkyl, aryl, or heteroaryl,
(W) pN +Z 3Z 4Z 5Q where Z 3, Z 4, and Z 5 are, independently, H, alkyl, aryl, or heteroaryl, or
(W) pPO 3Z 6 where Z 6 is H, Na, a suitable mono- or di-valent cation, alkyl, aryl, or heteroaryl; and
V is a suitable anionic moiety to form the salt of the compound of formula I, and
Q is a suitable anionic moiety to form the salt of the compound of formula I.
 
23. The method of claim 22, wherein each of Y and V is, independently, halide, sulfate, tosylate, carboxylate, polycarboxylate, alkyl, arylsulfonate, phosphate, phosphonate, borate, or boronate.
 
24. The method of claim 6, 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 pentaerythritol, dipentaerythritol, tripentaerythritol, tetrapentaerythritol, tris(hydroxymethyl)ethane, tris(hydroxymethyl)propane, tris(hydroxymethyl)nitromethane, tris(hydroxymethyl)aminomethane, or tris(hydroxymethyl)methanetrimethyl ammonium iodide.
 
25. The method of claim 6, wherein the organosilane is 3-(trihydroxysilyl)propyldimethyloctadecyl ammonium chloride and the polyol is pentaerythritol.
 
26. The method of claim 6, wherein the polyol is pentaerythritol.
 
27. The method of claim 6, wherein the product is monomeric.
 
28. The method of claim 6, wherein the product is oligomeric.
 
29. The method of claim 6, wherein the products of the composition are substantially monomeric.
 
30. The method of claim 6, wherein the products of the composition are substantially oligomeric.
 
31. The method of claim 6, wherein the polyol has the structure XX, XXV, or XXX:(HOCH2)3C(CH2)nR17  (XX) (HOCH2)3C(CH2)nR17  (XX) (HOCH2)3C(aryl)R17  (XXV) (HOCH2)3C(aryl)R17  (XXV) or(HOCH2)3C(benzyl)R17  (XXX) (HOCH2)3C(benzyl)R17  (XXX) wherein n is an integer of from 0 to 4;
R 17 is —COOH, —P(O)(OH) 2, —SO 3H, —B(OH) 2, —P(O)(OH), or —P(O)(OH)(OR 18),
where R 18 is a branched or unbranched alkyl group or perfluoroalkyl group having from 1 to 22 carbon atoms; an aryl group; a heteroaryl group; or a polyether.
 
32. The method of claim 6, wherein the polyol has the structure XXXV or XL: (HOCH2)3CN(R14)(R15)  (XXXV)or(HOCH2)3CN+(R14)(R15)(R16)U  (XL) (HOCH2)3CN+(R14)(R15)(R16)U  (XL)
wherein R 14 and R 15 are, independently, hydrogen; an alkyl group having from 1 to 4 carbon atoms that is unsubstituted or substituted with a hydroxy group; a polyalkylether group; or a benzyl group;
R 16 is hydrogen, a phenyl group; an alkyl group having from 1 to 22 carbon atoms that is unsubstituted or substituted with a hydroxy group; or a polyalkylether group, and
U is a halogen, a sulfate, a tosylate, a carboxylate, an alkylsulfonate, an arylsulfonate, a phosphate, a phosphonate salt, a borate, or a boronate salt.
 
33. The method of claim 6, wherein the organosilane is 3-(trimethoxysilyl)propylmethyldi(decyl) ammonium chloride and the polyol is pentaerythritol.