Water-stabilized organosilane compounds and methods for using the same
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First Claim
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1. A compound having the formula (R)nSi(X)4−
- n−
y(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 polyol containing at least three hydroxy groups, wherein all of the hydroxy groups are separated by at least three intervening atoms, and wherein the polyol is 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, wherein the polyol comprises(i) (HOCH2)3C(CH2)nR17;
(HOCH2)3C(aryl)R17;
or (HOCH2)3C(benzyl)R17 wherein n is an integer of from 0 to 4;
R17 is a functional group comprising —
COOH, —
P(O)(OH)2, —
SO3H, —
B(OH)2, —
P(O)(OH), or —
P(O)(OH)(OR18), where R18 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, wherein any hydrogen of a selected hydroxy group on the functional group can be replaced with Na+, K+, NH4+, Mg2+, Ca2+, or N(R70)4+, wherein R70 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;
or (ii) (HOCH2)3CN+(R14)(R15)(R16)U−
wherein R14 and R15 are, independently, H, —
O—
, or alkyl of from 1 to about 4 carbon atoms, unsubstituted or substituted with OH, piperazine, morpholine, a polyalkylether, or benzyl;
R16 is H, phenyl or alkyl of from 1 to 22 carbons, unsubstituted or substituted with OH, phenyl-, or a polyalkylether; and
U is halogen, sulfate, tosylate or carboxylate, a polycarboxylate salt, functionalized carboxylate, an alkyl or arylsulfonate salt, a phosphate or phosphonate salt, or a borate or boronate;
or (iii) pentaerythritol, dipentaerythritol, tripentaerythritol, tetrapentaerythritol, or tris(hydroxymethyl)nitromethane;
or (iv) tetrakis(hydroxymethyl)phosphonium chloride.
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Abstract
The product of reacting an organosilane optionally having a nonhydrolizable organic group, but having one ore 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.
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Citations
28 Claims
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1. A compound having the formula (R)nSi(X)4−
- n−
y(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 polyol containing at least three hydroxy groups, wherein all of the hydroxy groups are separated by at least three intervening atoms, and wherein the polyol is 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, wherein the polyol comprises(i) (HOCH2)3C(CH2)nR17;
(HOCH2)3C(aryl)R17;
or(HOCH2)3C(benzyl)R17 wherein n is an integer of from 0 to 4;
R17 is a functional group comprising —
COOH, —
P(O)(OH)2, —
SO3H, —
B(OH)2, —
P(O)(OH), or —
P(O)(OH)(OR18),where R18 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,wherein any hydrogen of a selected hydroxy group on the functional group can be replaced with Na+, K+, NH4+, Mg2+, Ca2+, or N(R70)4+, wherein R70 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;
or(ii) (HOCH2)3CN+(R14)(R15)(R16)U− wherein R14 and R15 are, independently, H, —
O—
, or alkyl of from 1 to about 4 carbon atoms, unsubstituted or substituted with OH, piperazine, morpholine, a polyalkylether, or benzyl;
R16 is H, phenyl or alkyl of from 1 to 22 carbons, unsubstituted or substituted with OH, phenyl-, or a polyalkylether; and
U is halogen, sulfate, tosylate or carboxylate, a polycarboxylate salt, functionalized carboxylate, an alkyl or arylsulfonate salt, a phosphate or phosphonate salt, or a borate or boronate;
or(iii) pentaerythritol, dipentaerythritol, tripentaerythritol, tetrapentaerythritol, or tris(hydroxymethyl)nitromethane;
or(iv) tetrakis(hydroxymethyl)phosphonium chloride. - View Dependent Claims (2, 3, 4, 5, 6, 7, 19, 20, 21, 22, 23)
- n−
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8. A water stable composition comprising water and an organosilane-polyol product that is formed by reacting in the absence of water
(a) an organosilane of the formula RnSiX4− - 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 comprises (i) (HOCH2)3C(CH2)nR17;
(HOCH2)3C(aryl)R17;
or(HOCH2)3C(benzyl)R17 wherein n is an integer of from 0 to 4;
R17 is a functional group comprising —
COOH, —
P(O)(OH)2, —
SO3H, —
B(OH)2, —
P(O)(OH), or —
P(O)(OH)(OR18),where R18 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,wherein any hydrogen of a selected hydroxy group on the functional group can be replaced with Na+, K+, NH4+, Mg2+, Ca2+, or N(R70)4+, wherein R70 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;
or(ii) (HOCH2)3CN+(R14)(R15)(R16)U− wherein R14 and R15 are, independently, H, —
O—
, or alkyl of from 1 to about 4 carbon atoms, unsubstituted or substituted with OH, piperazine, morpholine, a polyalkylether, or benzyl;
R16 is H, phenyl or alkyl of from 1 to 22 carbons, unsubstituted or substituted with OH, phenyl-, or a polyalkylether; and
U is halogen, sulfate, tosylate or carboxylate, a polycarboxylate salt, functionalized carboxylate, an alkyl or arylsulfonate salt, a phosphate or phosphonate salt, or a borate or boronate;
or(iii) pentaerythritol, dipentaerythritol, tripentaerythritol, tetrapentaerythritol, or tris(hydroxymethyl)nitromethane;
or(iv) tetrakis(hydroxymethyl)phosphonium chloride. - View Dependent Claims (9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 24, 25, 26, 27, 28)
- n where n is an integer of from 0 to 3;
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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InventorsAllred, Gary D., Liebeskind, Lanny S.
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Primary Examiner(s)WYROZEBSKI LEE, KATARZYNA I
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Application NumberUS09/320,771Time in Patent Office698 DaysField of Search524/386, 524/387, 524/506, 524/540, 524/541, 524/588, 556/410, 556/463, 528/21, 528/32, 528/38US Class Current524/386CPC 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. ...
