US3925319A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Light-stable thermoplastic polyurethanes
Assignee: Uniroyal Chemical Co Inc
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Filing: 1973-09-19
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Granted: 1975-12-09
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Expires: 1993-09-19
Abstract
Abstract One-shot thermoplastic polyurethanes stable to discoloration by light are made by reacting a polyol with a mixture of aromatic and aliphatic polyisocyanates. For example, polytetramethylene ether glycol and 1,4-butanediol may be reacted with a mixture of methylenebis(p-phenylisocyanate) and methylenebis(4cyclohexylisocyanate) in the presence of stannous octoate in a one shot procedure to form a thermoplastic suitable for coating fabric.
Inventors
- 👤 Norman A Hiatt
- 👤 Harold G Wolf
- 👤 Robert A Hlavacek
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 21:09
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/70; C08G18/72; C08G18/721; C08G18/724
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
73 words
A LIGHT STABLE SOLID THERMOPLASTIC POLYURETHANE COMPOSITION COMPRISING A ONE-SHOT REACTION PRODUCT OF A MACROPOLYOL AND A MIXTURE OF AN AROMATIC POLYISOCYANATE AND AN ALIPHATIC POLYISOCYANATE, THE EQUIVALENCE RATIO OF AROMATIC TO ALIPHATIC POLYISOCYANATE BEING 50:50, AND THE OVERALL ISOCYANATE TO HYDROXY RATIO BEING FROM 1:1 TO 1.1:1 WHEREBY THE SOLID THERMOPLASTIC POLYURETHANE IS SUBSTANTIALLY DEVOTED OF FREE ISOCYANATE GROUPS, THE SAID AROMATIC POLYISOCYANATE BEING METHYLENEBIS(4-PHENYLISOCYANATE) AND THE SAID ALIPGATIC POLYISOCYANATE BEING METHYLENEBIS(4-CYCOLHEXYLISOCYANATE).
Claim 2
Dependent Claim
73 words
A LIGHT STABLE SOLID THERMOPLASTIC POLYURETHANE COMPOSITION COMPRISING A ONE-SHOT REACTION PRODUCT OF A MACROPOLYOL AND A MIXTURE OF AN AROMATIC POLYISOCYANATE AND AN ALIPHATIC POLYISOCYANATE, THE EQUIVALENCE RATIO OF AROMATIC TO ALIPHATIC POLYISOCYANATE BEING 50:50, AND THE OVERALL ISOCYANATE TO HYDROXY RATIO BEING FROM 1:1 TO 1.1:1 WHEREBY THE SOLID THERMOPLASTIC POLYURETHANE IS SUBSTANTIALLY DEVOTED OF FREE ISOCYANATE GROUPS, THE SAID AROMATIC POLYISOCYANATE BEING METHYLENEBIS(4-PHENYLISOCYANATE) AND THE SAID ALIPGATIC POLYISOCYANATE BEING METHYLENEBIS(4-CYCOLHEXYLISOCYANATE).
Claim 3
Dependent Claim
82 words
A light stable solid thermoplastic polyurethane composition comprising a one-shot reaction product of (a) a macropolyol, (b) a low molecular weight polyol chain extender and (c) a mixture of aromatic polyisocyanate and aliphatic polyisocyanate, the equivalence ratio of aromatic to aliphatic polyisocyanate being 50:50, and the overall isocyanate to hydroxyl ratio being from 1: 1 to 1.1:1 whereby the solid thermoplastic polyurethane is substantially devoid of free isocyanate groups, the said aromatic polyisocyanate being methylenebis(4-phenylisocyanate) and the said aliphatic polyisocyanate being methylenebis(4-cyclohexylisocyanate.
Claim 4
Dependent Claim
82 words
A light stable solid thermoplastic polyurethane composition comprising a one-shot reaction product of (a) a macropolyol, (b) a low molecular weight polyol chain extender and (c) a mixture of aromatic polyisocyanate and aliphatic polyisocyanate, the equivalence ratio of aromatic to aliphatic polyisocyanate being 50:50, and the overall isocyanate to hydroxyl ratio being from 1: 1 to 1.1:1 whereby the solid thermoplastic polyurethane is substantially devoid of free isocyanate groups, the said aromatic polyisocyanate being methylenebis(4-phenylisocyanate) and the said aliphatic polyisocyanate being methylenebis(4-cyclohexylisocyanate.
Claim 5
Dependent Claim
125 words
A light stable solid thermoplastic polyurethane composition comprising a one-shot reaction product of (a) a macropolyol having an equivalent weight of from 100 to 2000 and an hydroxyl number of from 200 to 600 selected from the group consisting of polyether polyols and polyester polyols, (b) a low molecular weight glycol chain extender and (c) a mixture of aromatic diisocyanate and aliphatic diisocyanate, the overall isocyanate to hydroxyl molar ratio being from 1:1 to 1.1:1, the equivalence ratio of aromatic to aliphatic isocyanate being 50:50, and the equivalence ratio of chain extender (b) to macropolyol (a) being from 1:1 to 2:1, the solid thermoplastic polyurethane being substantially devoid of free isocyanate groups, the said aromatic diisocyanate being methylenebis(4-phenylisocyanate) and the said aliphatic diisocyanate being methylenebis(4-cyclohexylisocyanate).
Claim 6
Dependent Claim
125 words
A light stable solid thermoplastic polyurethane composition comprising a one-shot reaction product of (a) a macropolyol having an equivalent weight of from 100 to 2000 and an hydroxyl number of from 200 to 600 selected from the group consisting of polyether polyols and polyester polyols, (b) a low molecular weight glycol chain extender and (c) a mixture of aromatic diisocyanate and aliphatic diisocyanate, the overall isocyanate to hydroxyl molar ratio being from 1:1 to 1.1:1, the equivalence ratio of aromatic to aliphatic isocyanate being 50:50, and the equivalence ratio of chain extender (b) to macropolyol (a) being from 1:1 to 2:1, the solid thermoplastic polyurethane being substantially devoid of free isocyanate groups, the said aromatic diisocyanate being methylenebis(4-phenylisocyanate) and the said aliphatic diisocyanate being methylenebis(4-cyclohexylisocyanate).
Claim 7
Dependent Claim
19 words
A light stable solid thermoplastic polyurethane composition as in claim 3 in which the said macropolyol is poly (oxytetramethylene)glycol.
Claim 8
Dependent Claim
20 words
A light stable solid thermoplastic polyurethane composition as in claim 3 in the form of a coating on a fabric.
Claim 9
Independent Claim
97 words
A method of making a solid light stable thermoplastic polyurethane by a one-shot reaction comprising mixing a polyol with a blend of an aromatic polyisocyanate and an aliphatic polyisocyanate, the molar ratio of isocyanate to hydroxyl being within the range of from 1:1 to 1.1:1, the equivalence ratio of aromatic to aliphatic polyisocyanate being 50:50, and subjecting the mixture to a temperature within the range of from 25*C to 200*C, whereby there is formed a solid thermoplastic polyurethane substantially devoid of free isocyanate groups, the said aromatic polyisocyanate being methylenebis(4-phenylisocyanate) and the said aliphatic polyisocyanate being methylenebis(4-cyclohexylisocyanate).
Claim 10
Independent Claim
97 words
A method of making a solid light stable thermoplastic polyurethane by a one-shot reaction comprising mixing a polyol with a blend of an aromatic polyisocyanate and an aliphatic polyisocyanate, the molar ratio of isocyanate to hydroxyl being within the range of from 1:1 to 1.1:1, the equivalence ratio of aromatic to aliphatic polyisocyanate being 50:50, and subjecting the mixture to a temperature within the range of from 25*C to 200*C, whereby there is formed a solid thermoplastic polyurethane substantially devoid of free isocyanate groups, the said aromatic polyisocyanate being methylenebis(4-phenylisocyanate) and the said aliphatic polyisocyanate being methylenebis(4-cyclohexylisocyanate).
Claim 11
Independent Claim
137 words
A method of making a light stable thermoplastic polyurethane comprising mixing (a) a polyester or polyether polyol having an equivalent weight of from 100 to 3000 and an hydroxyl number from 20 to 600, (b) a low molecular weight glycol chain extender and (c) a mixture of aromatic diisocyanate and aliphatic diisocyanate, the overall isocyanate to hydroxyl molar ratio being from 1:1 to 1.1:1, the equivalence ratio of aromatic to aliphatic isocyanate being 50:50 and the equivalence ratio of chain extender (b) to polyol (a) being from 1:1 to 2:1, and subjecting the mixture of (a), (b) and (c) to a temperature of from 50* to 150*C. whereby a solid thermoplastic polyurethane substantially devoid of free isocyanate groups is formed by a one-shot reaction, the said aromatic diisocyanate being methylenebis(4-phenylisocyanate) and the said aliphatic diisocyanate being methylenebis(4-cyclohexylisocyanate).
Claim 12
Independent Claim
137 words
A method of making a light stable thermoplastic polyurethane comprising mixing (a) a polyester or polyether polyol having an equivalent weight of from 100 to 3000 and an hydroxyl number from 20 to 600, (b) a low molecular weight glycol chain extender and (c) a mixture of aromatic diisocyanate and aliphatic diisocyanate, the overall isocyanate to hydroxyl molar ratio being from 1:1 to 1.1:1, the equivalence ratio of aromatic to aliphatic isocyanate being 50:50 and the equivalence ratio of chain extender (b) to polyol (a) being from 1:1 to 2:1, and subjecting the mixture of (a), (b) and (c) to a temperature of from 50* to 150*C. whereby a solid thermoplastic polyurethane substantially devoid of free isocyanate groups is formed by a one-shot reaction, the said aromatic diisocyanate being methylenebis(4-phenylisocyanate) and the said aliphatic diisocyanate being methylenebis(4-cyclohexylisocyanate).
Claim 13
Independent Claim
157 words
A method of making a coated fabric, coated with a light stable solid thermoplastic polyurethane, comprising mixing (a) a polyester or polyether polyol having an equivalent weight of from 500 to 2000 and an hydroxyl number of from 30 to 120, (b) a low molecular weight glycol chain extender and (c) a blend of aromatic diisocyanate and aliphatic diisocyanate, the overall isocyanate to hydroxyl molar ratio being from 1:1 to 1.1:1, the equivalence ratio of aromatic to aliphatic isocyanate being 50: 50, and the equivalence ratio of chain extender (b) to polyol (a) being from 1:1 to 2:1, and subjecting the mixture of (a), (b) and (c) to a temperature of from 50* to 150*C. whereby a solid thermoplastic polyurethane substantially devoid of free isocyanate groups is formed by a one-shot reaction, and coating a fabric with the resulting light stable solid thermoplastic polyurethane, the said aromatic diisocyanate being methylenebis(4-phenylisocyanate) and the said aliphatic diisocyanate being methylenebis(4-cyclohexylisocyanate).
Claim 14
Independent Claim
157 words
A method of making a coated fabric, coated with a light stable solid thermoplastic polyurethane, comprising mixing (a) a polyester or polyether polyol having an equivalent weight of from 500 to 2000 and an hydroxyl number of from 30 to 120, (b) a low molecular weight glycol chain extender and (c) a blend of aromatic diisocyanate and aliphatic diisocyanate, the overall isocyanate to hydroxyl molar ratio being from 1:1 to 1.1:1, the equivalence ratio of aromatic to aliphatic isocyanate being 50: 50, and the equivalence ratio of chain extender (b) to polyol (a) being from 1:1 to 2:1, and subjecting the mixture of (a), (b) and (c) to a temperature of from 50* to 150*C. whereby a solid thermoplastic polyurethane substantially devoid of free isocyanate groups is formed by a one-shot reaction, and coating a fabric with the resulting light stable solid thermoplastic polyurethane, the said aromatic diisocyanate being methylenebis(4-phenylisocyanate) and the said aliphatic diisocyanate being methylenebis(4-cyclohexylisocyanate).
Claim 15
Dependent Claim
15 words
A method as in claim 2 in which the said polyol is poly (oxytetramethylene) glycol.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1978-12-08 | 1979-06-09 | 1979-12-09 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-12-08 | 1983-06-09 | 1983-12-09 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-12-08 | 1987-06-09 | 1987-12-09 | $7700.00 | Window Closed / Lapsed |