Water-stabilized organosilane compounds and methods for using the same
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First Claim
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1. A water-stable composition comprising water and a product that is formed by reacting in watera) an organosilane of the formula Rn SiX4-n where n is an integer of from 0 to 2;
- each R is, independently, a nonhydrolyzable organic group further wherein each R is, independently, alkyl, alkyl alcohol, or aromatic; and
each X is, independently, a hydrolyzable group, further wherein each X is, independently, hydroxy, alkoxy, halogen, acetyl, acetoxy, acyl, a hydroxylated solid or liquid polymeric moiety, polyether or polyalkylether, withb) 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 of the formula I;
space="preserve" listing-type="equation">{R.sub.11 (W).sub.p }(R.sub.33).sub.3-o C{(CH.sub.2).sub.q OH}.sub.o(I)whereino 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;
R11 and R33 are, independently, halogen, H, CH2 OH, N(CH2 CH2 OH)2 CH3+ V-, NH2, NO2, N(H)(CH2)3 OSO3 H, N+ (CH3)2 (CH2)3 SO3-, N(CH3)3+ V-, (CH2)OPO3 H2, (CHz)PO3 H2,N(H)R34 (CF2)e CF3 where e is an integer of from 1 to about 22 and R34 is CO or SO2,(W)p ZO where Z is H, alkyl, aryl, or heteroaryl,(W)p ZS(O)r where Z is H, Na, a suitable mono- or di-valent cation, alkyl, aryl, or heteroaryl and r is an integer from 0 to 2,(W)p Z1 Z2 N where Z1 and Z2 are, independently, H, alkyl, aryl, or heteroaryl,(W)p Z3 Z4 Z5 N+ Q- where Z3, Z4, and Z5 are, independently, H, alkyl, aryl, or heteroaryl and where Q- is a suitable anionic moiety to form a salt, or(W)p Z6 PO3 where Z6 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.
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Abstract
The product of reacting an organosilane optionally having a nonhydrolizable organic group, but having one or more hydrolyzable groups, with a polyol containing at least three hydroxy groups, where any two of the hydroxy groups are separated by at least three intervening atoms. Water-stabilized organosilane compounds. A water stable composition made from the product or compound and water. A method of treating a substrate by contacting the substrate with the product, compound, or composition for a period of time sufficient for treatment of the substrate. A treated substrate having adhered thereto the product, compound, or composition.
147 Citations
44 Claims
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1. A water-stable composition comprising water and a product that is formed by reacting in water
a) an organosilane of the formula Rn SiX4-n where n is an integer of from 0 to 2; - each R is, independently, a nonhydrolyzable organic group further wherein each R is, independently, alkyl, alkyl alcohol, or aromatic; and
each X is, independently, a hydrolyzable group, further wherein each X is, independently, hydroxy, alkoxy, halogen, acetyl, acetoxy, acyl, a hydroxylated solid or liquid polymeric moiety, polyether or polyalkylether, withb) 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 of the formula I;
space="preserve" listing-type="equation">{R.sub.11 (W).sub.p }(R.sub.33).sub.3-o C{(CH.sub.2).sub.q OH}.sub.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; R11 and R33 are, independently, halogen, H, CH2 OH, N(CH2 CH2 OH)2 CH3+ V-, NH2, NO2, N(H)(CH2)3 OSO3 H, N+ (CH3)2 (CH2)3 SO3-, N(CH3)3+ V-, (CH2)OPO3 H2, (CHz)PO3 H2, N(H)R34 (CF2)e CF3 where e is an integer of from 1 to about 22 and R34 is CO or SO2, (W)p ZO where Z is H, alkyl, aryl, or heteroaryl, (W)p ZS(O)r where Z is H, Na, a suitable mono- or di-valent cation, alkyl, aryl, or heteroaryl and r is an integer from 0 to 2, (W)p Z1 Z2 N where Z1 and Z2 are, independently, H, alkyl, aryl, or heteroaryl, (W)p Z3 Z4 Z5 N+ Q- where Z3, Z4, and Z5 are, independently, H, alkyl, aryl, or heteroaryl and where Q- is a suitable anionic moiety to form a salt, or (W)p Z6 PO3 where Z6 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. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18)
- each R is, independently, a nonhydrolyzable organic group further wherein each R is, independently, alkyl, alkyl alcohol, or aromatic; and
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19. A water stable composition comprising water and a compound that is formed by reacting in water components comprising
a) an organosilane of the formula Rn SiX4-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, withb) 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. - View Dependent Claims (20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32)
- each R is, independently, a nonhydrolizable organic group; and
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33. A water-stable composition comprising water and a compound having the formula (R)n Si(X)4-y-n (R41)y wherein n is an integer of from 0 to 3;
- y is an integer of from 1 to 4;
each R is, independently, a nonhydrolizable organic group;
each X is, independently, a hydrolyzable group; and
each R41 is, independently, a poly(tetrahydrofuran), a poly(vinyl)alcohol, or starch containing at least three hydroxy groups, wherein all of the hydroxy groups are separated by at least three intervening atoms and wherein the R41 bonded to the Si by removal of the hydrogen from one of the at least three hydroxy groups such that the oxygen of the one of the at least three hydroxy groups is bonded to Si.
- y is an integer of from 1 to 4;
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34. A water-stable composition comprising water and a product that is formed by reacting in water an organosilane of the formula II, III, IV, or V:
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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 of the three is, independently, halogen or R6 O, where R6 is H, alkyl of from 1 to about 6 carbon atoms, acetyl, acetoxy or acyl; R35 is 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, halogen, H, alkyl of from 1 to about 8 carbon atoms, isobutyl, phenyl, or n-octyl; R2 is benzyl, vinyl or alkyl of from 1 to about 3 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;
orR3 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, thioamide, nitro, amine, or halide R5 is lower alkyl alcohol, CH2 C6 H5, 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; with a poly(tetrahydrofuran), a poly(vinyl)alcohol, starch, or a mixture thereof.
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35. A water stable composition consisting essentially of water and a compound that is formed by reacting in water components comprising
a) an organosilane of the formula Rn SiX4-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, withb) 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.
- each R is, independently, a nonhydrolizable organic group; and
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36. A water-stable composition comprising water and a product that is formed by reacting in water a) an organosilane of the formula Rn SiX4-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 organosilane is 3-(trimethoxysilyl)propyldimethyloctadecyl ammonium chloride and the polyol is pentaerythritol.
- each R is, independently, a nonhydrolizable organic group; and
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37. A water-stable composition comprising water and a product that is formed by reacting in water a) an organosilane of the formula Rn SiX4-n where n is an integer of from 0 to 3;
- each R is, independently, a nonhydrolizable organic group; and
each X is, independenely, 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 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 of the three is, independently, halogen or R6 O, where R6 is H, alkyl of from 1 to about 6 carbon atoms, acetyl, acetoxy, or acyl; R35 is 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, halogen, H, alkyl of from 1 to about 8 carbon atoms, isobutyl, phenyl, or n-octyl; R2 is benzyl, vinyl or alkyl of from 1 to about 3 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;
orR3 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, thioamide, nitro, amine, or halide R5 is lower alkyl alcohol, CH2 C6 H5, 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;
space="preserve" listing-type="equation">{R.sub.11 (W).sub.p }(R.sub.33).sub.3-o C{(CH.sub.2).sub.q OH}.sub.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; R11 and R33 are, independently, halogen, H, CH2 OH, N(CH2 CH2 OH)2 CH3+ V-, NH2, NO2, N(H)(CH2)3 OSO3 H, N+ (CH3)2 (CH2)3 SO3-, N(CH3)3+ V-, (CH2)OPO3 H2, (CH2)PO3 H2, N(H)R34 (CF2)e CF3 where e is an integer of from 1 to about 22 and R34 is CO or SO2, N(H)R34 (CF2)e CF3 where e is an integer of from 1 to about 22 and R34 is CO or SO2, (W)p ZO where Z is H, alkyl, aryl, or heteroaryl, (W)p ZS(O)r where Z is H, Na, a suitable mono- or di-valent cation, alkyl, aryl, or heteroaryl and r is an integer from 0 to 2, (W)p Z1 Z2 N where Z1 and Z2 are, independently, H, alkyl, aryl, or heteroaryl, (W)p Z3 Z4 Z5 N+ Q- where Z3, Z4, and Z5 are, independently, H, alkyl, aryl, or heteroaryl and where Q- is a suitable anionic moiety to form a salt, or (W)p Z6 PO3 where Z6 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. - View Dependent Claims (38)
- each R is, independently, a nonhydrolizable organic group; and
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39. A water-stable composition comprising water and a product that is formed by reacting in water a) an organosilane of the formula Rn SiX4-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 a compound having the formula VII;
space="preserve" listing-type="equation">(R.sub.12)(R.sub.13)C{(CH.sub.2).sub.5 R.sub.14 }.sub.2 (VII)wherein s is an integer of from 1 to 2, R12 is (CH2)g R14 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(R15)(R16), N(H)(CH2)3 OSO3 H, N(H)(CH2)3 OSO3 H, N(H)(CH2)3 OSO3 H, N+ (CH3)2 (CH2)3 SO3 ;
N+ (CH3)3 T-, N+ (R17)(R18)(R19)T-, whereR15, R16, R17, and R18 are, independently, H, O, or lower alkyl of from 1 to about 4 carbon atoms, polyalkyl ester, benzyl, or R15 and R16, together, or R17 and R18, together, may, independently, form an amide, sulfonamide, phosphonamide, oxime, thioamide, quaternary ammonium, imine, imide, guanidine, piperazine, morpholine, or N(O)R20 R21, where R20 and R21 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; R19 is H or alkyl of from 1 to about 22 carbon atoms; and T- is a suitable anionic moiety to form a quaternary ammonium salt of the compound of formula VII; R13 is H, OH, (CH2)5 R14, (CH2)OPO3 H2, or (CH2)PO3 H2, lower alkyl of from 1 to 4 carbon atoms, lower alkoxy of from 1 to about 4 carbon atoms; and each R14 is, independently, OH or {--CH2 C(CH2 OH)2 CH2 O}j --H where j is an integer of from 0 to 5 and wherein one of the R14 moieties is bonded to the Si by removal of the hydrogen from a hydroxy such that the oxygen of the hydroxy is bonded to Si; or a perfluoro-analog thereof;
or a mixture thereof. - View Dependent Claims (40, 41, 42, 43, 44)
- each R is, independently, a nonhydrolizable organic group; and
Specification
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Litigation Data
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Current AssigneeEmory University
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Original AssigneeEmory University
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InventorsLiebeskind, Lanny S., Allred, Gary D.
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Primary Examiner(s)Stucker, Jeffrey
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Application NumberUS08/646,156Time in Patent Office1,239 DaysField of Search524/386, 524/540, 524/541, 524/506, 524/588, 524/474, 524/480, 524/509, 524/387, 524/389, 528/28, 424/401, 424/404US Class Current524/389CPC Class CodesC07F 7/1804 Compounds having Si-O-C lin...C08G 77/04 PolysiloxanesC08G 77/26 nitrogen-containing groupsC09D 4/00 Coating compositions, e.g. ...
