US4954598A
Expired / Lapsed
US
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Fast-cure polyurethane sealant composition containing silyl-substituted guanidine accelerators
Assignee: ADCO TECHNOLOGIES Inc
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Filing: 1988-10-13
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Granted: 1990-09-04
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Expires: 2008-10-13
Abstract
Abstract One-component, moisture-curable sealant compositions having fast cure times comprise a mixture of a silane-capped polyurethane polymer, an aminosilane cross-linking agent, and a silyl-substituted guanidine accelerator.
Inventors
- 👤 Jamil Baghdachi
- 👤 Keith H. Mahoney
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 20:05
CPC Classifications
C; C09; C09K; C09K3/00; C09K3/10; C09K3/1006; C09K3/1021; C08; C08G; C08G18/00; C08G18/06; C08G18/08; C08G18/10; C08K; C08K5/00; C08K5/54; C08K5/544; C08K5/5465; C09K2003/1034; C09K2003/1056; C09K2003/1071; Y; Y10; Y10S; Y10S528/00; Y10S528/901
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
327 words
A one-component, moisture-curable sealant composition comprising a mixture of (a) a silane-terminated polyurethane polymer of the formula ##STR12## wherein R is lower alkyl of from 1 to 6 carbon atoms; R 1 is a divalent bridging radical selected from the group consisting of a divalent hydrocarbon radical, a divalent hydrocarbon ether radical, and a divalent hydrocarbon amino radical; A is selected from the group consisting of --S-- and --NR 2 -- where R 2 is hydrogen or alkyl of from one to six carbon atoms; (b) from 0.2 to 1.0 parts by weight of an aminosilane per 100 parts by weight of said silane-terminated polyurethane polymer, said aminosilane having the structure ##STR13## wherein x is an integer of from one to three; R 3 and R 4 may be the same or different and are selected from alkyl of from one to four carbon atoms; R 5 is alkyl of from one to four carbon atoms or alkoxyl of from one to four carbon atoms; R 6 is hydrogen or --(CH 2 ) y NHR 7 wherein R 7 is hydrogen or 13 (CH 2 ) z NH 2 and wherein y and z may be the same or different and are integers of from one to three; (c) from 0.2 to 1.0 parts by weight of an accelerator per 100 parts by weight of said silane-terminated polyurethane polymer, said accelerator selected from the group consisting of compounds or mixtures thereof having the structure ##STR14## where x and R are as previously defined; R 8 , is hydrogen or ##STR15## where R 3 , R 4 , R 5 , and x are as defined above; R 9 and R 10 are hydrogen or, when taken together with the carbon atoms to which they are attached, form a saturated six-membered carbocyclic ring; and R 11 , R 12 , R 13 , and R 14 are independently hydrogen or alkyl of from one to four carbon atoms.
Claim 2
Dependent Claim
327 words
A one-component, moisture-curable sealant composition comprising a mixture of (a) a silane-terminated polyurethane polymer of the formula ##STR12## wherein R is lower alkyl of from 1 to 6 carbon atoms; R 1 is a divalent bridging radical selected from the group consisting of a divalent hydrocarbon radical, a divalent hydrocarbon ether radical, and a divalent hydrocarbon amino radical; A is selected from the group consisting of --S-- and --NR 2 -- where R 2 is hydrogen or alkyl of from one to six carbon atoms; (b) from 0.2 to 1.0 parts by weight of an aminosilane per 100 parts by weight of said silane-terminated polyurethane polymer, said aminosilane having the structure ##STR13## wherein x is an integer of from one to three; R 3 and R 4 may be the same or different and are selected from alkyl of from one to four carbon atoms; R 5 is alkyl of from one to four carbon atoms or alkoxyl of from one to four carbon atoms; R 6 is hydrogen or --(CH 2 ) y NHR 7 wherein R 7 is hydrogen or 13 (CH 2 ) z NH 2 and wherein y and z may be the same or different and are integers of from one to three; (c) from 0.2 to 1.0 parts by weight of an accelerator per 100 parts by weight of said silane-terminated polyurethane polymer, said accelerator selected from the group consisting of compounds or mixtures thereof having the structure ##STR14## where x and R are as previously defined; R 8 , is hydrogen or ##STR15## where R 3 , R 4 , R 5 , and x are as defined above; R 9 and R 10 are hydrogen or, when taken together with the carbon atoms to which they are attached, form a saturated six-membered carbocyclic ring; and R 11 , R 12 , R 13 , and R 14 are independently hydrogen or alkyl of from one to four carbon atoms.
Claim 3
Dependent Claim
54 words
A one-component, moisture-curable sealant composition as defined in claim 1 wherein said silane-terminated polyurethane polymer comprises a reaction product of: a polyether polyol contain at least two hydroxyl groups per molecule and a number average molecular weight of about 1000 to about 3000 and an isocyanate having at least two isocyanate groups per molecule.
Claim 4
Dependent Claim
28 words
A one-component, moisture-curable sealant composition as defined in claim 1 wherein said silane-terminated polyurethane polymer has a number average molecular weight of from about 10,000 to about 30,000.
Claim 5
Dependent Claim
23 words
A one-component, moisture-curable sealant composition as defined in claim 3 wherein A is --NR 2 -- where R 2 is as defined therein.
Claim 6
Dependent Claim
34 words
A one-component, moisture-curable sealant composition as defined in claim 1 wherein said composition comprises from 0.4 to 0.8 parts by weight of said aminosilane per 100 parts by weight of said silane-terminated polyurethane polymer.
Claim 7
Dependent Claim
16 words
A one-component, moisture-curable sealant composition as defined in claim 5 wherein said aminosilane is N-(beta-aminoethyl)-gamma-aminopropyl trimethoxysilane.
Claim 8
Dependent Claim
34 words
A one-component, moisture-curable sealant composition as defined in claim 1 wherein said composition comprises from 0.2 to 0.8 parts by weight of said accelerator per 100 parts by weight of said silane-terminated polyurethane polymer.
Claim 9
Dependent Claim
50 words
A one-component, moisture-curable sealant composition as defined in claim 1 wherein said accelerator is selected from the group consisting of (a) N"-[2-hydroxy-3-[3-(trimethoxysilyl)propoxy]-propyl]-N,N,N',N'-tetramethylguanidine; (b) N"-[2-hydroxy-3-[3-(ethoxydimethylsilyl)propoxy]-propyl]-N,N,N',N'-tetramethylguanidine; (c) N"-[2-hydroxy-3-[3-(diethoxymethylsilyl)propoxy]-propyl]-N,N,N',N'-tetramethylguanidine; (d) N"-[4 - [2-(trimethoxysilyl)ethyl]-2-hydroxycyclohexyl]-N,N,N',N'-tetramethylguanidine; (e) [3-(triethoxysilyl)propyl]carbamic acid, [2-[[bis(dimethylamino)methylene]amino]-1-[[3-(trimethoxysilyl)propoxy]methyl]ethyl] ester; (f) [3-(triethoxysilyl)propyl]carbamic acid, [2-[[bis(dimethylamino)methylene]amino]-1-[[3-(ethoxydimethylsilyl)propoxy (g) [3-(triethoxysilyl)propyl]carbamic acid, [2-[[bis(dimethylamino)methylene]amino]-1-[[3-(diethoxymethylsilyl)propoxy]methyl]ethyl] ester; and (h) [3-(triethoxysilyl)propyl]carbamic acid, [2-[[bis(dimethylamino)methylene]amino]-5-[2-(trimethoxysilyl)ethyl]] ester.
Claim 10
Dependent Claim
15 words
A one-component, moisture-curable sealant composition as defined in claim 8 wherein said accelerator is N"-[2-hydroxy-3-[3-(trimethoxysilyl)propoxy]-propyl]-N,N,N',N'-tetramethylguanidine.
Claim 11
Dependent Claim
15 words
A one-component, moisture-curable sealant composition as defined in claim 8 wherein said accelerator is N"-[2-hydroxy-3-[3-(ethoxydimethylsilyl)propoxy]-propyl]-N,N,N',N'-tetramethylguanidine.
Claim 12
Dependent Claim
15 words
A one-component, moisture-curable sealant composition as defined in claim 8 wherein said accelerator is N"-[2-hydroxy-3-[3-(diethoxymethylsilyl)propoxy]propyl]-N,N,N',N'-tetramethylguanidine.
Claim 13
Dependent Claim
15 words
A one-component, moisture-curable sealant composition as defined in claim 8 wherein said accelerator is N"-[4-[2-(trimethoxysilyl)ethyl]-2-hydroxycyclohexyl]-N,N,N',N'-tetramethylguanidine.
Claim 14
Dependent Claim
18 words
A one-component, moisture-curable sealant composition as defined in claim 8 wherein said accelerator is [3-(triethoxysilyl)propyl]carbamic acid, [2-[[bis(dimethylamino)methylene]amino]-1-[[3-(trimethoxysilyl)propoxy]methyl]ethyl] ester.
Claim 15
Dependent Claim
18 words
A one-component, moisture-curable sealant composition as defined in claim 8 wherein said accelerator is [3-(triethoxysilyl)propyl]carbamic acid, [2-[[bis(dimethylamino)methylene]amino]-1-[[3-(ethoxydimethylsilyl)propoxy]methyl]ethyl] ester.
Claim 16
Dependent Claim
18 words
A one-component, moisture-curable sealant composition as defined in claim 8 wherein said accelerator is [3-(triethoxysilyl)propyl]carbamic acid, [2-[[bis(dimethylamino)methylene]amino]---[[3-(diethoxymethylsilyl)propoxy]methyl]ethyl] ester.
Claim 17
Dependent Claim
18 words
A one-component, moisture-curable sealant composition as defined in claim 8 wherein said accelerator is [3-(triethoxysilyl)propyl]carbamic acid, [2-[[bis(dimethylamino)methylene]amino]-5-[2-(trimethoxysilyl)ethyl]] ester.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1993-09-03 | 1994-03-05 | 1994-09-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-09-03 | 1998-03-05 | 1998-09-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-09-03 | 2002-03-05 | 2002-09-04 | $7700.00 | Window Closed / Lapsed |