Patent US4284751A successfully refreshed from Google Patents.
US4284751A
Expired / Lapsed
US
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Polyurethane sealant system
Assignee: Essex Chemical Corp
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Filing: 1980-05-14
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Granted: 1981-08-18
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Expires: 2000-05-14
Abstract
Abstract A polyurethane sealant including a polyurethane having terminal isocyanate groups and containing a dual curing catalysti of organic bismuth and organic tin, said polyurethane being the reaction product of a liquid poly (lower) alkylene polyol having a molecular weight of 6,000 or more and three to five hydroxyl groups and a sterically unhindered aromatic diisocyanate. The polyurethane sealant may be used in conjunction with a silane based primer and when applied to glass surfaces provides a high strength and rapidly curing seal.
Inventors
- 👤 Jack W. Hutt
- 👤 Fernando E. Blanco
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 12:18
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/08; C08G18/16; C08G18/22; C08G18/10; C08G2190/00; Y; Y10; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31551; Y10T428/31598; Y10T428/31609; Y10T428/31612
Claims Analysis
Total Claims: 32
Claim 1
Independent Claim
199 words
A polyurethane sealant which when exposed to ambient moisture will cure rapidly to form a seal having high tensile strength consisting essentially of (A) a polyurethane polymer containing terminal isocyanate groups in an amount of not more than about 2.0 weight % based on the weight of said polyurethane, said terminal isocyanate groups being blocked to prevent further reaction by a volatile blocking agent, said polyurethane polymer being the reaction product of (1) a liquid poly (lower) alkylene ether polyol having a molecular weight of greater than about 6,000 and from three to five hydroxyl groups with (2) a sterically unhindered aromatic diisocyanate; (B) a catalytic curing effective amount of (a) an organic bismuth salt selected from the group consisting of bismuth tri-(2-ethyl hexoate) and bismuth tri-(neo-decanoate) and (b) an organic tin salt of the formula: ##STR2## wherein each of R 1 and R 2 is alkyl of from 1 to 12 carbon atoms and each of R 3 and R 4 are lower alkyl; (C) up to 200 weight %, based on the weight of the polyol, of inert fillers: and (D) up to 100 weight %, based on the weight of the polyol, of polyurethane compatible plasticizers.
Claim 2
Dependent Claim
199 words
A polyurethane sealant which when exposed to ambient moisture will cure rapidly to form a seal having high tensile strength consisting essentially of (A) a polyurethane polymer containing terminal isocyanate groups in an amount of not more than about 2.0 weight % based on the weight of said polyurethane, said terminal isocyanate groups being blocked to prevent further reaction by a volatile blocking agent, said polyurethane polymer being the reaction product of (1) a liquid poly (lower) alkylene ether polyol having a molecular weight of greater than about 6,000 and from three to five hydroxyl groups with (2) a sterically unhindered aromatic diisocyanate; (B) a catalytic curing effective amount of (a) an organic bismuth salt selected from the group consisting of bismuth tri-(2-ethyl hexoate) and bismuth tri-(neo-decanoate) and (b) an organic tin salt of the formula: ##STR2## wherein each of R 1 and R 2 is alkyl of from 1 to 12 carbon atoms and each of R 3 and R 4 are lower alkyl; (C) up to 200 weight %, based on the weight of the polyol, of inert fillers: and (D) up to 100 weight %, based on the weight of the polyol, of polyurethane compatible plasticizers.
Claim 3
Dependent Claim
21 words
A polyurethane sealant according to claim 1 wherein the liquid polyol has a molecular weight of between about 6,000 and 30,000.
Claim 4
Dependent Claim
36 words
A polyurethane sealant according to claim 1 wherein the amount of organic bismuth compound is from about 0.1 weight % to about 0.6 weight %, calculated as bismuth and based on the weight of the polyol.
Claim 5
Dependent Claim
16 words
A polyurethane sealant according to claim 3 wherein the organic bismuth compound is bismuth tri-(2-ethyl hexoate).
Claim 6
Dependent Claim
37 words
A polyurethane sealant according to claims 1 or 3 wherein the organic tin compound is present in an amount of from about 0.1 weight % to about 1 weight % based on the weight of the polyol.
Claim 7
Dependent Claim
16 words
A polyurethane sealant according to claim 5 wherein the organic tin compound is dibutyl tin dilaurate.
Claim 8
Dependent Claim
18 words
A polyurethane sealant according to claim 1 wherein said poly(lower) alkylene ether polyol is a polypropylene ether polyol.
Claim 9
Dependent Claim
243 words
A polyurethane sealant system which when exposed to ambient moisture will cure rapidly to form a seal having high tensile strength comprising (A) a liquid polyurethane sealant consisting essentially of (1) a polyurethane polymer containing terminal isocyanate groups in an amount of not more than about 2.0 weight % based on the weight of said polyurethane, said terminal isocyanate groups being blocked to prevent further reaction by a volatile blocking agent, said polyurethane polymer being the reaction product of (i) a liquid poly(lower) alkylene ether polyol having a molecular weight of greater than about 6,000 and from three to five hydroxyl groups, (ii) a sterically unhindered diisocyanate; (2) a catalytic curing effective amount of (a) an organic bismuth compound selected from the group consisting of bismuth tri-(2-ethyl hexoate) and bismuth tri-neo-decanoate and (b) an organic tin compound of the formula: ##STR3## wherein each of R 1 and R 2 is alkyl of from 1 to 12 carbon atoms and each of R 3 and R 4 are lower alkyl; (3) up to 200 weight %, based on the weight of the polyol, of inert fillers; and (4) up to 50 weight %, based on the weight of the polyol, of polyurethane compatible plasticizers and (B) a silane based primer composition which is rapidly curable in the presence of ambient moisture and consisting essentially of (1) a silane compound having isocyanate reactive groups and (2) a catalytic effective amount of a silane hydrolysis catalyst.
Claim 10
Dependent Claim
243 words
A polyurethane sealant system which when exposed to ambient moisture will cure rapidly to form a seal having high tensile strength comprising (A) a liquid polyurethane sealant consisting essentially of (1) a polyurethane polymer containing terminal isocyanate groups in an amount of not more than about 2.0 weight % based on the weight of said polyurethane, said terminal isocyanate groups being blocked to prevent further reaction by a volatile blocking agent, said polyurethane polymer being the reaction product of (i) a liquid poly(lower) alkylene ether polyol having a molecular weight of greater than about 6,000 and from three to five hydroxyl groups, (ii) a sterically unhindered diisocyanate; (2) a catalytic curing effective amount of (a) an organic bismuth compound selected from the group consisting of bismuth tri-(2-ethyl hexoate) and bismuth tri-neo-decanoate and (b) an organic tin compound of the formula: ##STR3## wherein each of R 1 and R 2 is alkyl of from 1 to 12 carbon atoms and each of R 3 and R 4 are lower alkyl; (3) up to 200 weight %, based on the weight of the polyol, of inert fillers; and (4) up to 50 weight %, based on the weight of the polyol, of polyurethane compatible plasticizers and (B) a silane based primer composition which is rapidly curable in the presence of ambient moisture and consisting essentially of (1) a silane compound having isocyanate reactive groups and (2) a catalytic effective amount of a silane hydrolysis catalyst.
Claim 11
Dependent Claim
22 words
A polyurethane sealant system according to claim 8 wherein the liquid polyol has a molecular weight of between about 6,000 and 30,000.
Claim 12
Dependent Claim
17 words
A polyurethane sealant system according to claim 8 wherein the volatile blocking agent is a tautomeric enol.
Claim 13
Dependent Claim
17 words
A polyurethane sealant system according to claim 10 wherein the volatile blocking agent is a di(lower)alkyl malonate.
Claim 14
Dependent Claim
23 words
A polyurethane sealant system according to claim 8 wherein the silane hydrolysis catalyst promotes the reaction of an isocyanate with an active hydrogen.
Claim 15
Dependent Claim
38 words
A polyurethane sealant system according to claim 12 wherein said catalyst for promoting the reaction of an isocyanate with an active hydrogen is a compound of a heavy metal Group I or Group II of the periodic table.
Claim 16
Dependent Claim
37 words
A polyurethane sealant system according to claim 8 wherein the amount of organic bismuth compound is from about 0.1 weight % to about 0.6 weight %, calculated as bismuth and based on the weight of the polyol.
Claim 17
Dependent Claim
17 words
A polyurethane sealant system according to claim 4 wherein the organic bismuth compound is bismuth tri-(2-ethyl hexoate).
Claim 18
Dependent Claim
37 words
A polyurethane sealant according to claims 8 or 14 wherein the organic tin compound is present in an amount of from about 0.1 weight % to about 1 weight % based on the weight of the polyol.
Claim 19
Dependent Claim
17 words
A polyurethane sealant system according to claim 16 wherein the organic tin compound is dibutyl tin dilaurate.
Claim 20
Dependent Claim
19 words
A polyurethane sealant system according to claim 8 wherein said poly(lower) alkylene either polyol is a polypropylene ether polyol.
Claim 21
Independent Claim
253 words
A method for forming a high tensile strength seal on a glass substrate which comprises priming said glass substrate which is exposed to ambient moisture with (A) a silane based primer composition which is rapidly curable in the presence of ambient moisture and consisting essentially of (1) a silane compound having isocyanate reactive groups and (2) a catalytic effective amount of a silane hydrolysis catalyst and applying over said silane base primer (B) a liquid polyurethane sealant consisting essentially of (1) a polyurethane polymer containing terminal isocyanate groups in an amount of not more than about 2.0 weight % based on the weight of said polyurethane, said terminal isocyanate groups being blocked to prevent further reaction by a volatile blocking agent, said polyurethane being the reaction product of (i) a liquid poly(lower) alkylene ether polyol having three to five hydroxyl groups and a molecular weight of greater than about 6,000 and (ii) a sterically unhindered aromatic diisocyanate; (2) a cataytic curing effective amount of (a) an organic bismuth compound selected from the group consisting of bismuth tri-(2-ethyl hexoate) and bismuth tri-neo-decanoate and (b) an organic tin compound of the formula: ##STR4## wherein each of R 1 and R 2 is alkyl of from 1 to 12 carbon atoms and each of R 3 and R 4 is lower alkyl; (3) up to 200 weight %, based on the weight of the polyol of inert filler and (4) up to 50 weight %, based on the weight of the polyol, of polyurethane compatible plasticizers.
Claim 22
Independent Claim
253 words
A method for forming a high tensile strength seal on a glass substrate which comprises priming said glass substrate which is exposed to ambient moisture with (A) a silane based primer composition which is rapidly curable in the presence of ambient moisture and consisting essentially of (1) a silane compound having isocyanate reactive groups and (2) a catalytic effective amount of a silane hydrolysis catalyst and applying over said silane base primer (B) a liquid polyurethane sealant consisting essentially of (1) a polyurethane polymer containing terminal isocyanate groups in an amount of not more than about 2.0 weight % based on the weight of said polyurethane, said terminal isocyanate groups being blocked to prevent further reaction by a volatile blocking agent, said polyurethane being the reaction product of (i) a liquid poly(lower) alkylene ether polyol having three to five hydroxyl groups and a molecular weight of greater than about 6,000 and (ii) a sterically unhindered aromatic diisocyanate; (2) a cataytic curing effective amount of (a) an organic bismuth compound selected from the group consisting of bismuth tri-(2-ethyl hexoate) and bismuth tri-neo-decanoate and (b) an organic tin compound of the formula: ##STR4## wherein each of R 1 and R 2 is alkyl of from 1 to 12 carbon atoms and each of R 3 and R 4 is lower alkyl; (3) up to 200 weight %, based on the weight of the polyol of inert filler and (4) up to 50 weight %, based on the weight of the polyol, of polyurethane compatible plasticizers.
Claim 23
Dependent Claim
20 words
A method according to claim 19 wherein the liquid polyol has a molecular weight of between about 6,000 and 30,000.
Claim 24
Dependent Claim
15 words
A method according to claim 19 wherein the volatile blocking agent is a tautomeric enol.
Claim 25
Dependent Claim
16 words
A method according to claim 21 wherein the volatile blocking agent is a di(lower) alkyl malonate.
Claim 26
Dependent Claim
21 words
A method according to claim 19 wherein the silane hydrolysis catalyst promotes the reaction of an isocyanate with an active hydrogen.
Claim 27
Dependent Claim
37 words
A method according to claim 23 wherein said catalyst for promoting the reaction of an isocyanate with an active hydrogen is a compound of a heavy metal of Group I or Group II of the periodic table.
Claim 28
Dependent Claim
34 words
A method according to claim 19 wherein the amount of organic bismuth is from about 0.1 weight % to about 0.6 weight %, calculated as bismuth and based on the weight of the polyol.
Claim 29
Dependent Claim
15 words
A method according to claim 25 wherein the organic bismuth compound is bismuth tri-(2-ethyl hexoate).
Claim 30
Independent Claim
36 words
A method according to claims 23 or 25 wherein the organic tin compound is present in an amount of from about 0.1 weight % to about 1 weight % based on the weight of the polyol.
Claim 31
Dependent Claim
15 words
A method according to claim 27 wherein the organic tin compound is dibutyl tin dilaurate.
Claim 32
Dependent Claim
17 words
A method according to claim 19 wherein said poly(lower) alkylene ether polyol is a polypropylene ether polyol.
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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) | 1984-08-17 | 1985-02-16 | 1985-08-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-08-17 | 1989-02-16 | 1989-08-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-08-17 | 1993-02-16 | 1993-08-18 | $7700.00 | Window Closed / Lapsed |