US5591818A
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Organosilane polycondensation products
Assignee: Evonik Operations GmbH
•
Filing: 1995-03-29
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Granted: 1997-01-07
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Expires: 2015-03-29
Abstract
Abstract Disclosed are organosilane polycondensation products prepared by hydrolysis of an hydrogen salt of an aminosilane compound or by hydrolysis of an aminosilane followed by reaction with an alkyl salt. The compounds are useful in forming stable aqueous solutions and as adhesion promoters between inorganic and organic surfaces.
Inventors
- 👤 Burkhard Standke
- 👤 Hartwig Rauleder
- 👤 Claus-Dietrich Seiler
- 👤 Hans-Joachim Kotzsch
- 👤 Hermann Peeters
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 03:18
CPC Classifications
C; C08; C08G; C08G77/00; C08G77/04; C08G77/38; C08G77/382; C08G77/388; C08G77/22; C08G77/26; C08K; C08K9/00; C08K9/04; C08K9/06
Claims Analysis
Total Claims: 36
Claim 1
Independent Claim
108 words
An organosilane polycondensation product of the formula [Z--SiO.sub.[1.5-(a+b+z)/2] (OH).sub.a (OR).sub.b R'.sub.z ].sub.r (I) wherein R and R' are each independently alkyl of 1 to 8 carbon atoms; Z is --(CH.sub.2).sub.n NH.sub.c R.sub.d.sup.1 (CH.sub.2).sub.m NH.sub.e R.sub.f.sup.2.HX.sub.(f+d) ; (II) X is an anion of an organic or inorganic acid; R 1 is --(CH 2 ) p Ar 1 or vinylbenzyl; R 2 is --(CH 2 ) q Ar 2 or vinylbenzyl; Ar 1 and Ar 2 are each independently aryl, aralkyl or aralkenyl; 0<a<3, 0<b<3, (a+b+z)<3, z≦1, r>1; n, m, p and q are each independently integers of 1 to 8, inclusive; and c≦1, d≦1, e≦2, f≦2, c+d=1, e+f=2, 1≦(f+d)≦3.
Claim 2
Dependent Claim
108 words
An organosilane polycondensation product of the formula [Z--SiO.sub.[1.5-(a+b+z)/2] (OH).sub.a (OR).sub.b R'.sub.z ].sub.r (I) wherein R and R' are each independently alkyl of 1 to 8 carbon atoms; Z is --(CH.sub.2).sub.n NH.sub.c R.sub.d.sup.1 (CH.sub.2).sub.m NH.sub.e R.sub.f.sup.2.HX.sub.(f+d) ; (II) X is an anion of an organic or inorganic acid; R 1 is --(CH 2 ) p Ar 1 or vinylbenzyl; R 2 is --(CH 2 ) q Ar 2 or vinylbenzyl; Ar 1 and Ar 2 are each independently aryl, aralkyl or aralkenyl; 0<a<3, 0<b<3, (a+b+z)<3, z≦1, r>1; n, m, p and q are each independently integers of 1 to 8, inclusive; and c≦1, d≦1, e≦2, f≦2, c+d=1, e+f=2, 1≦(f+d)≦3.
Claim 3
Dependent Claim
18 words
The organosilane polycondensation product of claim 1 wherein X is Cl - or CH 3 COO - .
Claim 4
Dependent Claim
118 words
The organosilane polycondensation product of claim 1 selected from the group consisting of [CH 3 COOH.C 6 H 5 CH 2 NH(CH 2 ) 2 NH(CH 2 ) 3 SiO.sub.[1.5-(a+b)/2] (OH) a (OCH 3 ) b ] r , [HCl.C 6 H 5 CH 2 NH(CH 2 ) 2 NH(CH 2 ) 3 SiO.sub.[1.5-(a+b)/2] (OH) a (OCH 3 ) b ] r , [CH 3 COOH.CH 2 ═CH--C 6 H 4 CH 2 NH(CH 2 ) 2 NH(CH 2 ) 3 SiO.sub.[1.5-(a+b)/2] (OH) a (OCH 3 ) b ] r , and [HCl.CH 2 ═CH--C 6 H 4 CH 2 NH(CH 2 ) 2 NH(CH 2 ) 3 SiO.sub.[1.5-(a+b)/2] (OH) a (OCH 3 ) b ] r .
Claim 5
Dependent Claim
26 words
The method of claim 1, which additionally comprises performing the hydrolysis in the presence of an inert solvent to adjust the viscosity of the reaction product.
Claim 6
Dependent Claim
24 words
The method of claim 4, wherein said solvent is a monohydric or polyhydric, branched-chain, straight-chain or cyclic alcohol of 1 to 18 carbon atoms.
Claim 7
Dependent Claim
17 words
The method of claim 1, wherein R 1 and R 2 are each independently benzyl or vinylbenzyl.
Claim 8
Independent Claim
173 words
A method of preparing an organosilane polycondensation product of the formula (Z--SiO.sub.[1.5-(a+b+z)/2] (OH).sub.a (OR).sub.b R'.sub.z).sub.r (I) wherein R and R' are each independently alkyl of 1 to 8 carbon atoms; Z is --(CH.sub.2).sub.n NH.sub.c R.sub.d.sup.1 (CH.sub.2).sub.m NH.sub.e R.sub.f.sup.2.HX.sub.(f+d) (II); X is an anion of an organic or inorganic acid; R 1 is --(CH 2 ) p Ar 1 or vinylbenzyl; R 2 is --(CH 2 ) q Ar 2 or vinylbenzyl; Ar 1 and Ar 2 are each independently aryl, aralkyl or aralkenyl; 0<a<3, 0<b<3, (a+b+z)<3, z≦1, r>1; n, m, p and q are each independently integers of 1 to 8, inclusive, and c≦1, d≦1, e≦2, f≦2, c+d=1, e+f=2; the method comprising: partially hydrolyzing a compound of the formula H.sub.2 N(CH.sub.2).sub.m NH(CH.sub.2).sub.n Si(OR).sub.3-z R'.sub.z (IV) with 0.25 to 4 moles of water per mole of compound of formula IV based on the silane content thereof to form a condensation product; and then reacting the condensation product with a compound of the formula X--R.sup.1 (V) wherein X and R 1 have the above-defined meanings.
Claim 9
Independent Claim
173 words
A method of preparing an organosilane polycondensation product of the formula (Z--SiO.sub.[1.5-(a+b+z)/2] (OH).sub.a (OR).sub.b R'.sub.z).sub.r (I) wherein R and R' are each independently alkyl of 1 to 8 carbon atoms; Z is --(CH.sub.2).sub.n NH.sub.c R.sub.d.sup.1 (CH.sub.2).sub.m NH.sub.e R.sub.f.sup.2.HX.sub.(f+d) (II); X is an anion of an organic or inorganic acid; R 1 is --(CH 2 ) p Ar 1 or vinylbenzyl; R 2 is --(CH 2 ) q Ar 2 or vinylbenzyl; Ar 1 and Ar 2 are each independently aryl, aralkyl or aralkenyl; 0<a<3, 0<b<3, (a+b+z)<3, z≦1, r>1; n, m, p and q are each independently integers of 1 to 8, inclusive, and c≦1, d≦1, e≦2, f≦2, c+d=1, e+f=2; the method comprising: partially hydrolyzing a compound of the formula H.sub.2 N(CH.sub.2).sub.m NH(CH.sub.2).sub.n Si(OR).sub.3-z R'.sub.z (IV) with 0.25 to 4 moles of water per mole of compound of formula IV based on the silane content thereof to form a condensation product; and then reacting the condensation product with a compound of the formula X--R.sup.1 (V) wherein X and R 1 have the above-defined meanings.
Claim 10
Dependent Claim
34 words
The method of claim 7, which additionally comprises performing the hydrolysis and the subsequent reaction of the condensation product in the presence of an inert solvent to adjust the viscosity of the reaction product.
Claim 11
Dependent Claim
24 words
The method of claim 8, wherein said solvent is a monohydric or polyhydric, branched-chain, straight-chain or cyclic alcohol of 1 to 18 carbon atoms.
Claim 12
Dependent Claim
14 words
The method of claim 7, wherein compound V is vinylbenzyl chloride or benzyl chloride.
Claim 13
Dependent Claim
56 words
A water-soluble, functionalized, polycondensed organosilane obtained by partial hydrolysis of NH 2 (CH 2 ) 2 NH(CH 2 ) 3 Si(OCH 3 ) 3 and reaction of the hydrolysis product with a compound selected from the group consisting of CH 2 ═CH--C 6 H 4 --CH 2 Cl and C 6 H 5 --CH 2 Cl.
Claim 14
Dependent Claim
56 words
A water-soluble, functionalized, polycondensed organosilane obtained by partial hydrolysis of NH 2 (CH 2 ) 2 NH(CH 2 ) 3 Si(OCH 3 ) 3 and reaction of the hydrolysis product with a compound selected from the group consisting of CH 2 ═CH--C 6 H 4 --CH 2 Cl and C 6 H 5 --CH 2 Cl.
Claim 15
Dependent Claim
20 words
The water-soluble, functionalized organosilane of claim 11, wherein the hydrolysis product has a polymerization degree n of 1 to 20.
Claim 16
Dependent Claim
59 words
A method for the preparation of a water-soluble, functionalized polycondensed organosilane of claim 11 comprising partially hydrolyzing NH 2 (CH 2 ) 2 NH(CH 2 ) 3 Si(OCH 3 ) 3 to form a hydrolysis product; and reacting the hydrolysis product with CH 2 ═CH--C 6 H 4 --CH 2 Cl or C 6 H 5 --CH 2 Cl.
Claim 17
Dependent Claim
12 words
The method of claim 13, wherein the aminoethylaminopropyltrimethoxysilane is dissolved in methanol.
Claim 18
Dependent Claim
29 words
The method of claim 13, wherein the aminoethylaminopropyltrimethoxysilane and the water are used in a molar ratio of 1:0.25 to 4 based on the silicon content of the silane.
Claim 19
Dependent Claim
13 words
The method of claim 13, wherein the reactions are performed under nitrogen shielding.
Claim 20
Dependent Claim
21 words
The method of claim 13, wherein the reactions are performed in a temperature range of from room temperature to 65° C.
Claim 21
Dependent Claim
18 words
The method of claim 13, wherein the reactions take place over a period of up to 4 hours.
Claim 22
Dependent Claim
16 words
The method of claim 13, wherein alcohol is added to the reaction mixture and/or product mixture.
Claim 23
Dependent Claim
16 words
The method of claim 19, wherein the alcohol is selected from methanol, ethanol or mixtures thereof.
Claim 24
Dependent Claim
55 words
A water-soluble, functionalized, polycondensed organosilane, obtained by partial hydrolysis of [C 6 H 5 --CH 2 --NH(CH 2 ) 2 NH(CH 2 ) 3 Si(OCH 3 ) 3 ].HCl (N-benzyl-aminoethylaminopropyltrimethoxysilane hydrochloride) or [CH 2 ═CH--C 6 H 5 --CH 2 --NH(CH 2 ) 2 NH(CH 2 ) 3 Si(OCH 3 ) 3 ].HCl (N-vinylbenzylaminoethylaminopropyltrimethoxysilane hydrochloride).
Claim 25
Dependent Claim
55 words
A water-soluble, functionalized, polycondensed organosilane, obtained by partial hydrolysis of [C 6 H 5 --CH 2 --NH(CH 2 ) 2 NH(CH 2 ) 3 Si(OCH 3 ) 3 ].HCl (N-benzyl-aminoethylaminopropyltrimethoxysilane hydrochloride) or [CH 2 ═CH--C 6 H 5 --CH 2 --NH(CH 2 ) 2 NH(CH 2 ) 3 Si(OCH 3 ) 3 ].HCl (N-vinylbenzylaminoethylaminopropyltrimethoxysilane hydrochloride).
Claim 26
Dependent Claim
22 words
The water-soluble, functionalized, polycondensed organosilane of claim 21, wherein the hydrolysis product has a degree of polymerization n of 1 to 20.
Claim 27
Dependent Claim
62 words
A method for the preparation of water-soluble, functionalized polycondensed organosilane according to claim 21, comprising partially hydrolyzing [C 6 H 5 --CH 2 --NH(CH 2 ) 2 NH(CH 2 ) 3 Si(OCH 3 ) 3 ].HCl (N-benzyl-aminoethylaminopropyltrimethoxysilane hydrochloride) or [CH 2 ═CH--C 6 H 5 --CH 2 --NH(CH 2 ) 2 NH(CH 2 ) 3 Si(OCH 3 ) 3 ].HCl (N-vinylbenzylaminoethylaminopropyltrimethoxysilane hydrochloride).
Claim 28
Dependent Claim
13 words
The method of claim 23, wherein the silane hydrochloride is dissolved in methanol.
Claim 29
Dependent Claim
30 words
The method of claim 23, wherein the silane hydrochloride and the water are used in a molar ratio of 1:0.25 to 4 based on the silicon content of the silane.
Claim 30
Dependent Claim
14 words
The method of claim 23, wherein the reaction is conducted under a nitrogen shield.
Claim 31
Dependent Claim
21 words
The method of claim 23, wherein the reaction is performed in a temperature range of from room temperature to 65° C.
Claim 32
Dependent Claim
19 words
The method of claim 23, wherein the reaction takes place over a time period of up to 4 hours.
Claim 33
Dependent Claim
17 words
The method of claim 23, wherein an alcohol is added to the reaction mixture and/or product mixture.
Claim 34
Dependent Claim
16 words
The method of claim 29, wherein the alcohol is at least one of methanol and ethanol.
Claim 35
Independent Claim
155 words
A method of preparing an organosilane polycondensation product of the formula [Z--SiO.sub.[1.5-(a+b+z)/2] (OH).sub.a (OR).sub.b R'.sub.z ].sub.r (I) wherein R and R' are each independently alkyl of 1 to 8 carbon atoms; Z is --(CH.sub.2).sub.n NH.sub.c R.sub.d.sup.1 (CH.sub.2).sub.m NH.sub.e R.sub.f.sup.2.HX.sub.(f+d) ; (II); X is an anion of an organic or inorganic acid; R 1 is --(CH 2 ) p Ar 1 or vinylbenzyl; R 2 is --(CH 2 ) q Ar 2 or vinylbenzyl; Ar 1 and Ar 2 are each independently aryl, aralkyl or aralkenyl; 0<a<3, 0<b<3, (a+b+z)<3, z≦1, r>1; n, m, p and q are each independently integers of 1 to 8, inclusive; and c≦1, d≦1, e≦2, f≦2, c+d=1, e+f=2, 1≦(f+d)≦3; the method comprising: partially hydrolyzing a compound of the formula Z--Si(OR).sub.3-z R'.sub.z (III) wherein the compound of formula III and the water are used in a molar ratio of 1:0.25 to 4 based on the silane content of the compound of formula III.
Claim 36
Independent Claim
155 words
A method of preparing an organosilane polycondensation product of the formula [Z--SiO.sub.[1.5-(a+b+z)/2] (OH).sub.a (OR).sub.b R'.sub.z ].sub.r (I) wherein R and R' are each independently alkyl of 1 to 8 carbon atoms; Z is --(CH.sub.2).sub.n NH.sub.c R.sub.d.sup.1 (CH.sub.2).sub.m NH.sub.e R.sub.f.sup.2.HX.sub.(f+d) ; (II); X is an anion of an organic or inorganic acid; R 1 is --(CH 2 ) p Ar 1 or vinylbenzyl; R 2 is --(CH 2 ) q Ar 2 or vinylbenzyl; Ar 1 and Ar 2 are each independently aryl, aralkyl or aralkenyl; 0<a<3, 0<b<3, (a+b+z)<3, z≦1, r>1; n, m, p and q are each independently integers of 1 to 8, inclusive; and c≦1, d≦1, e≦2, f≦2, c+d=1, e+f=2, 1≦(f+d)≦3; the method comprising: partially hydrolyzing a compound of the formula Z--Si(OR).sub.3-z R'.sub.z (III) wherein the compound of formula III and the water are used in a molar ratio of 1:0.25 to 4 based on the silane content of the compound of formula III.
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