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US4857623A Expired / Lapsed US ⏱️ 0.0 years remaining

Alkoxysilane-terminated, moisture-hardening polyurethanes and their use in adhesives and sealing compositions

Assignee: Henkel AG and Co KGaA
•
Filing: 1987-08-25
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Granted: 1989-08-15
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Expires: 2007-08-25
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Abstract

Abstract Alkoxysilane-terminated, moisture-hardening polyurethanes obtained by reaction of OH-terminated diols and/or triols with diisocyanates to form NCO-terminated polyurethanes having an NCO functionality of at least 2, and reaction of some of the NCO groups with aliphatic alcohols to form a polyurethane having an NCO functionality of at least 1 and less than 2, or by reaction of the OH-terminated linear diols or triols with a mixture of mono- and diisocyanates to form NCO-terminated polyurethanes having an NCO functionality of at least 1 and less than 2, followed by a reaction of substantially all the free NCO functions of the polyurethanes obtained with aminoalkyl, mercaptoalkyl or epoxyalkyl alkoxysilanes. The polyurethanes thus obtained are particularly suitable as a basis for moisture-hardening one-component sealing compounds and adhesives.

Inventors

  • 👤 Winfried Emmerling
  • 👤 Tore Podola

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-08 12:50
CPC Classifications
C; C09; C09J; C09J175/00; C09J175/04; C08; C08G; C08G18/00; C08G18/06; C08G18/08; C08G18/10; C08G18/70; C08G18/71; C08G18/83; C08G18/831; C08G18/832; C08G2190/00

Claims Analysis

Total Claims: 18
Claim 1
Independent Claim 247 words
An alkoxysilane-terminated, moisture-hardening polyurethane prepared by the process comprising the steps of (a) reacting at least one OH-terminated linear diol or triol with at least one diisocyanate to form an NCO-terminated polyurethane having a number average NCO functionality of at least 2, (b) reacting some of the NCO-groups on the polyurethane obtained in step (a) with at least one linear or branched aliphatic alcohol containing from 1 to 18 carbon atoms or a monoalkylpolyalkylene glycol to form a polyurethane having a number average NCO functionality of at least 1 and less than 2, and (c) reacting substantially all the free NCO-groups in the polyurethane obtained from step (b) with at least one alkoxysilane corresponding to the formula ##STR3## in which X=--SH, --NHR 2 , ##STR4## --(NH--CH 2 --CH 2 ) n' --NHR 2 ; n'=1 or 2; R=--CH 3 , --CH 2 --CH 3 , or OR 1 ; R 1 =--(CH 2 --CH 2 --O) m --R 3 ; R 2 =H or an aliphatic or cycloaliphatic or aromatic hydrocarbon radical containing from 1 to 10 carbon atoms and optionally substituted with one or more C 1 -C 3 alkyl and/or C 1 -C 3 alkoxy groups; R 3 =an alkyl radical containing from 1 to 10 carbon atoms and optionally substituted with one or more C 1 -C 3 alkyl and/or C 1 -C 3 alkoxy groups; R 4 =an alkyl radical containing from 1 to 4 carbon atoms; and n=1-8; m=1-30; p≧1; and q+p=2.
Claim 2
Dependent Claim 247 words
An alkoxysilane-terminated, moisture-hardening polyurethane prepared by the process comprising the steps of (a) reacting at least one OH-terminated linear diol or triol with at least one diisocyanate to form an NCO-terminated polyurethane having a number average NCO functionality of at least 2, (b) reacting some of the NCO-groups on the polyurethane obtained in step (a) with at least one linear or branched aliphatic alcohol containing from 1 to 18 carbon atoms or a monoalkylpolyalkylene glycol to form a polyurethane having a number average NCO functionality of at least 1 and less than 2, and (c) reacting substantially all the free NCO-groups in the polyurethane obtained from step (b) with at least one alkoxysilane corresponding to the formula ##STR3## in which X=--SH, --NHR 2 , ##STR4## --(NH--CH 2 --CH 2 ) n' --NHR 2 ; n'=1 or 2; R=--CH 3 , --CH 2 --CH 3 , or OR 1 ; R 1 =--(CH 2 --CH 2 --O) m --R 3 ; R 2 =H or an aliphatic or cycloaliphatic or aromatic hydrocarbon radical containing from 1 to 10 carbon atoms and optionally substituted with one or more C 1 -C 3 alkyl and/or C 1 -C 3 alkoxy groups; R 3 =an alkyl radical containing from 1 to 10 carbon atoms and optionally substituted with one or more C 1 -C 3 alkyl and/or C 1 -C 3 alkoxy groups; R 4 =an alkyl radical containing from 1 to 4 carbon atoms; and n=1-8; m=1-30; p≧1; and q+p=2.
Claim 3
Dependent Claim 24 words
The polyurethane of claim 1 wherein the linear diol or triol has a number average molecular weight of from about 300 to about 6500.
Claim 4
Dependent Claim 24 words
The polyurethane of claim 2 wherein the linear diol or triol has a number average molecular weight of from about 500 to about 3000.
Claim 5
Dependent Claim 16 words
The polyurethane of claim 1 wherein the OH-terminated linear diol or triol is an alkoxylation product.
Claim 6
Dependent Claim 15 words
The polyurethane of claim 4 wherein the alkoxylation product is an ethoxylation and/or propoxylation product.
Claim 7
Dependent Claim 38 words
The polyurethane of claim 5 wherein the linear diol or triol is at least one of ethylene glycol, diethylene glycol, triethylene glycol, 1,2-propanediol, dipropylene glycol, a butanediol, a hexanediol, an octanediol, hydroxystearyl alcohol, trimethylene glycol, glycerol, or trimethylolpropane.
Claim 8
Dependent Claim 25 words
The polyurethane of claim 1 wherein the polyurethane obtained in step (b) has a number average NCO functionality of from about 1.2 to about 1.8.
Claim 9
Dependent Claim 32 words
The polyurethane of claim 1 wherein in step (b) a mono C 1 -C 6 alkylpolyalkylene glycol is employed having a number average molecular weight of from about 1000 to about 2000.
Claim 10
Dependent Claim 252 words
A process for the preparation of an alkoxysilane-terminated, moisture-hardening polyurethane comprising the steps of (a) reacting at least one OH-terminated linear diol or triol with at least one diisocyanate to form an NCO-terminated polyurethane having a number average NCO functionality of at least 2, (b) reacting some of the NCO-groups on the polyurethane from step (a) with at least one linear or branched aliphatic alcohol containing from 1 to 18 carbon atoms or a monoalkylpolyalkylene glycol to form a polyurethane having a number average NCO functionality of at least 1 and less than 2, and (c) reacting substantially all the free NCO-groups in the polyurethane obtained from step (b) with at least one alkoxysilane corresponding to the formula ##STR5## in which X=--SH, --NHR 2 , R 2 CH--CH--CH 2 --O--, --(NH--CH 2 --CH 2 ) n' --NHR 2 ; n'=1 or 2; R=--CH 3 , --CH 2 --CH 3 , or OR 1 ; R 1 =--(CH 2 --CH 2 --O) m --R 3 ; R 2 =H or an aliphatic or cycloaliphatic or aromatic hydrocarbon radical containing from 1 to 10 carbon atoms and optionally substituted with one or more C 1 -C 3 alkyl and/or C 1 -C 3 alkoxy groups; R 3 =an alkyl radical containing from 1 to 10 carbon atoms and optionally substituted with one or more C 1 -C 3 alkyl and/or C 1 -C 3 alkoxy groups; R 4 =an alkyl radical containing from 1 to 4 carbon atoms; and n=1-8; m=1-30; p≧1; and q+p=2.
Claim 11
Dependent Claim 252 words
A process for the preparation of an alkoxysilane-terminated, moisture-hardening polyurethane comprising the steps of (a) reacting at least one OH-terminated linear diol or triol with at least one diisocyanate to form an NCO-terminated polyurethane having a number average NCO functionality of at least 2, (b) reacting some of the NCO-groups on the polyurethane from step (a) with at least one linear or branched aliphatic alcohol containing from 1 to 18 carbon atoms or a monoalkylpolyalkylene glycol to form a polyurethane having a number average NCO functionality of at least 1 and less than 2, and (c) reacting substantially all the free NCO-groups in the polyurethane obtained from step (b) with at least one alkoxysilane corresponding to the formula ##STR5## in which X=--SH, --NHR 2 , R 2 CH--CH--CH 2 --O--, --(NH--CH 2 --CH 2 ) n' --NHR 2 ; n'=1 or 2; R=--CH 3 , --CH 2 --CH 3 , or OR 1 ; R 1 =--(CH 2 --CH 2 --O) m --R 3 ; R 2 =H or an aliphatic or cycloaliphatic or aromatic hydrocarbon radical containing from 1 to 10 carbon atoms and optionally substituted with one or more C 1 -C 3 alkyl and/or C 1 -C 3 alkoxy groups; R 3 =an alkyl radical containing from 1 to 10 carbon atoms and optionally substituted with one or more C 1 -C 3 alkyl and/or C 1 -C 3 alkoxy groups; R 4 =an alkyl radical containing from 1 to 4 carbon atoms; and n=1-8; m=1-30; p≧1; and q+p=2.
Claim 12
Dependent Claim 27 words
The process of claim 9 wherein in step (a) the linear diol or triol has a number average molecular weight of from about 300 to about 6500.
Claim 13
Dependent Claim 24 words
The process of claim 10 wherein the linear diol or triol has a number average molecular weight of from about 500 to about 3000.
Claim 14
Dependent Claim 19 words
The process of claim 9 wherein in step (a) the OH-terminated linear diol or triol is an alkoxylation product.
Claim 15
Dependent Claim 15 words
The process of claim 12 wherein the alkoxylation product is an ethoxylation and/or propoxylation product.
Claim 16
Dependent Claim 38 words
The process of claim 13 wherein the linear diol or triol is at least one of ethylene glycol, diethylene glycol, triethylene glycol, 1,2-propanediol, dipropylene glycol, a butanediol, a hexanediol, an octanediol, hydroxystearyl alcohol, trimethylene glycol, glycerol, or trimethylolpropane.
Claim 17
Dependent Claim 25 words
The process of claim 9 wherein the polyurethane obtained in step (b) has a number average NCO functionality of from about 1.2 to about 1.8.
Claim 18
Dependent Claim 27 words
The polyurethane of claim 9 wherein in step (b) a monoalkylpolyalkylene glycol is employed having a number average molecular weight of from about 1000 to about 2000.

References Cited (Backward Citations)

FR1115758A Cited
US3627722A Cited
US3979344A Cited
US4555561A Cited
US4567228A Cited
US4582873A Cited
JPH108479A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1992-08-14 1993-02-13 1993-08-15 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1996-08-14 1997-02-13 1997-08-15 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2000-08-14 2001-02-13 2001-08-15 $7700.00 Window Closed / Lapsed

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