US5077371A
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US
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Low free toluene diisocyanate polyurethanes
Assignee: Deutsche Bank AG New York Branch
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Filing: 1989-11-01
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Granted: 1991-12-31
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Expires: 2009-11-01
Abstract
Abstract A low-free toluene diisocyanate prepolymer is formed by reaction of a blend of the dimer of 2,4-toluene diisocyanate and an organic diisocyanate, preferably isomers of toluene diisocyanate, with high molecular weight polyols and optional low molecular weight polyols. The prepolymer can be further reacted with conventional organic diamines or organic polyol curatives to form elastomeric polyurethane/ureas or polyurethanes.
Inventors
- 👤 Ajaib Singh
- 👤 Robert J. Quint
- 👤 Ronald O. Rosenberg
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 18:40
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/70; C08G18/72; C08G18/77; C08G18/78; C08G18/79; C08G18/798; C08G18/08; C08G18/10; C08G18/12; C08G18/28; C08G18/65; C08G18/66; C08G18/6603; C08G18/6607
Claims Analysis
Total Claims: 25
Claim 1
Independent Claim
85 words
An organic diisocyanate prepolymer comprising the reaction product of: (a) an isocyanate blend of 0.3 to 6.0 weight percent of a dimer of 2,4-toluene diisocyanate with 94 to 99.7 weight percent of an organic diisocyanate; and (b) a polyol blend of 0-20 weight percent of a low molecular weight polyol having a molecular weight below 250 and 80-100 weight percent of a high molecular weight polyol having a molecular weight of at least 250 selected from the group consisting of polyether polyols and polyester polyols.
Claim 2
Dependent Claim
85 words
An organic diisocyanate prepolymer comprising the reaction product of: (a) an isocyanate blend of 0.3 to 6.0 weight percent of a dimer of 2,4-toluene diisocyanate with 94 to 99.7 weight percent of an organic diisocyanate; and (b) a polyol blend of 0-20 weight percent of a low molecular weight polyol having a molecular weight below 250 and 80-100 weight percent of a high molecular weight polyol having a molecular weight of at least 250 selected from the group consisting of polyether polyols and polyester polyols.
Claim 3
Dependent Claim
25 words
A prepolymer in accordance with claim 1 wherein said organic diisocyanate is selected from the group consisting of toluene diisocyanate, 4,4'-methylene bis (phenylisocyanate) and cyclohexyldiisocyanate.
Claim 4
Dependent Claim
18 words
A prepolymer in accordance with claim 1 wherein organic diisocyanate is 2,4-toluene diisocyanate, 2,6-toluene diisocyanate or mixtures thereof.
Claim 5
Dependent Claim
17 words
A process in accordance with claim 1 wherein said low molecular weight polyol is an aliphatic polyol.
Claim 6
Dependent Claim
30 words
A prepolymer in accordance with claim 1 wherein said high molecular weight polyol is a polyalkyleneether polyol or polyester polyol having a molecular weight between about 650 and about 3000.
Claim 7
Dependent Claim
25 words
A prepolymer in accordance with claim 1 wherein said low molecular weight polyol is present between 0 and 8 weight percent of said polyol blend.
Claim 8
Dependent Claim
16 words
A prepolymer in accordance with claim 1 wherein said high molecular weight polyol is polytetramethylene glycol.
Claim 9
Dependent Claim
102 words
A process for making a low-free toluene diisocyanate prepolymer comprising the steps of: (a) preparing a solution containing at least 0.3 weight percent of the dimer of 2,4-toluene diisocyanate in an aromatic diisocyanate to form an isocyanate blend; (b) adding a high molecular weight polyol selected from the group consisting of polyalkyleneether polyol and polyester polyol, with or without a low molecular weight polyol, to said isocyanate blend to form a reaction mixture; and (c) reacting said reaction mixture between 50° and 150° C. for a time sufficient to form said prepolymer having a free toluene diisocyanate level less than 0.4 percent.
Claim 10
Dependent Claim
102 words
A process for making a low-free toluene diisocyanate prepolymer comprising the steps of: (a) preparing a solution containing at least 0.3 weight percent of the dimer of 2,4-toluene diisocyanate in an aromatic diisocyanate to form an isocyanate blend; (b) adding a high molecular weight polyol selected from the group consisting of polyalkyleneether polyol and polyester polyol, with or without a low molecular weight polyol, to said isocyanate blend to form a reaction mixture; and (c) reacting said reaction mixture between 50° and 150° C. for a time sufficient to form said prepolymer having a free toluene diisocyanate level less than 0.4 percent.
Claim 11
Dependent Claim
18 words
A process according to claim 8 wherein said aromatic diisocyanate is 2,4- or 2,6-toluene diisocyanate or mixtures thereof.
Claim 12
Dependent Claim
26 words
A process according to claim 8 wherein said high molecular weight polyol is a polyalkyleneether polyol and said low molecular weight polyol is an aliphatic polyol.
Claim 13
Dependent Claim
15 words
A process according to claim 8 wherein said high molecular weight polyol is polytetramethyleneether glycol.
Claim 14
Dependent Claim
135 words
A process for making a low-free toluene diisocyanate prepolymer comprising the steps of: (a) adding in sufficient quantity a dimerization catalyst to an aromatic diisocyanate blend containing 2,4- or 2,6-toluene diisocyanate and mixtures thereof at elevated temperatures of up to 150° C. to form from 0.3 to about 6 parts by weight of a dimer of 2,4-toluene diisocyanate, insitu, thereby, forming an isocyanate/dimer blend; and (b) adding to said isocyanate/dimer blend a polyol blend of 0-20 weight percent of a polyol having a molecular weight below 250 and 80-100 weight percent of a polyol having a molecular weight of at least 250 selected from the group consisting of polyester polyol and polyether polyol; (c) reacting said polyol blend and isocyanate blend for a time sufficient to form a prepolymer having less than 0.4% free-toluene diisocyanate.
Claim 15
Dependent Claim
135 words
A process for making a low-free toluene diisocyanate prepolymer comprising the steps of: (a) adding in sufficient quantity a dimerization catalyst to an aromatic diisocyanate blend containing 2,4- or 2,6-toluene diisocyanate and mixtures thereof at elevated temperatures of up to 150° C. to form from 0.3 to about 6 parts by weight of a dimer of 2,4-toluene diisocyanate, insitu, thereby, forming an isocyanate/dimer blend; and (b) adding to said isocyanate/dimer blend a polyol blend of 0-20 weight percent of a polyol having a molecular weight below 250 and 80-100 weight percent of a polyol having a molecular weight of at least 250 selected from the group consisting of polyester polyol and polyether polyol; (c) reacting said polyol blend and isocyanate blend for a time sufficient to form a prepolymer having less than 0.4% free-toluene diisocyanate.
Claim 16
Dependent Claim
35 words
A process according to claim 12 wherein said dimerization catalyst is a trialkylphosphine, said organic diisocyanate is an isomer mixture of 2,4-and 2,6-toluene diisocyanates, and said high molecular weight polyol is a polyalkylene ether glycol.
Claim 17
Dependent Claim
24 words
A process according to claim 12 wherein said high molecular weight polyol is polytetramethylene ether glycol and said low molecular weight polyol is 1,4-butanediol.
Claim 18
Dependent Claim
110 words
A process of making a polyurethane elastomer from a low-free toluene diisocyanate prepolymer comprising: reacting a low-free toluene diisocyanate prepolymer with an aromatic diamine or polyol curative, said prepolymer being formed as the reaction product of an isocyanate blend of 0.3 to 6.0% weight percent of a dimer of 2,4-toluene diisocyanate with 94 to 99.7 weight percent of an organic diisocyanate, and a polyol blend of 0-20 weight percent of a low molecular weight polyol having a molecular weight below 250 and 80-100 weight percent of a high molecular weight polyol having a molecular weight of at least 250 selected from the group consisting of polyester polyol and polyether polyol.
Claim 19
Dependent Claim
110 words
A process of making a polyurethane elastomer from a low-free toluene diisocyanate prepolymer comprising: reacting a low-free toluene diisocyanate prepolymer with an aromatic diamine or polyol curative, said prepolymer being formed as the reaction product of an isocyanate blend of 0.3 to 6.0% weight percent of a dimer of 2,4-toluene diisocyanate with 94 to 99.7 weight percent of an organic diisocyanate, and a polyol blend of 0-20 weight percent of a low molecular weight polyol having a molecular weight below 250 and 80-100 weight percent of a high molecular weight polyol having a molecular weight of at least 250 selected from the group consisting of polyester polyol and polyether polyol.
Claim 20
Dependent Claim
22 words
A process according to claim 15 wherein said organic diisocyanate is a mixture of the 2,4- and 2,6 isomers of toluene diisocyanate.
Claim 21
Dependent Claim
27 words
A process in accordance with claim 15 wherein said high molecular weight polyol is a polyalkylenether glycol having a molecular weight between about 650 and about 3000.
Claim 22
Dependent Claim
25 words
A process in accordance with claim 15 wherein said low molecular weight polyol is present between 0 and 8 weight percent of said polyol blend.
Claim 23
Dependent Claim
17 words
A process in accordance with claim 15 wherein said high molecular weight polyol is polytetramethylene ether glycol.
Claim 24
Dependent Claim
128 words
A process for making a low-free toluene diisocyanate prepolymer comprising the steps of: (a) heating an aromatic diisocyanate blend containing 2,4- or 2,6-toluene diisocyanate and mixtures thereof at elevated temperatures of up to 150° C. to form from 0.3 to about 6 parts by weight of a dimer of 2,4-toluene diisocyanate, insitu, thereby, forming an isocyanate/dimer blend; and (b) adding to said isocyanate/dimer blend a polyol blend of 0-20 weight percent of a polyol having a molecular weight below 250 and 80-100 weight percent of a polyol having a molecular weight of at least 250 selected from the group consisting of polyester polyol and polyether polyol; (c) reacting said polyol blend and isocyanate blend for a time sufficient to form a prepolymer having less than 0.4% free-toluene diisocyanate.
Claim 25
Dependent Claim
128 words
A process for making a low-free toluene diisocyanate prepolymer comprising the steps of: (a) heating an aromatic diisocyanate blend containing 2,4- or 2,6-toluene diisocyanate and mixtures thereof at elevated temperatures of up to 150° C. to form from 0.3 to about 6 parts by weight of a dimer of 2,4-toluene diisocyanate, insitu, thereby, forming an isocyanate/dimer blend; and (b) adding to said isocyanate/dimer blend a polyol blend of 0-20 weight percent of a polyol having a molecular weight below 250 and 80-100 weight percent of a polyol having a molecular weight of at least 250 selected from the group consisting of polyester polyol and polyether polyol; (c) reacting said polyol blend and isocyanate blend for a time sufficient to form a prepolymer having less than 0.4% free-toluene diisocyanate.
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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) | 1994-12-30 | 1995-07-01 | 1995-12-31 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1998-12-30 | 1999-07-01 | 1999-12-31 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2002-12-30 | 2003-07-01 | 2003-12-31 | $7700.00 | Window Closed / Lapsed |