US4720536A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Blends of secondary alkyl aromatic diamines and polyhydric alcohols as curing agents in polyurethane manufacture
Assignee: Dorf Ketal Chemicals LLC
•
Filing: 1986-06-06
•
Granted: 1988-01-19
•
Expires: 2006-06-06
Abstract
Abstract Urethane prepolymers cured with a blend of an aromatic alkyl diamine and a polyhydric alcohol having more than two hydroxyl groups show excellent compression set and tensile properties. Ratios of diamine to alcohol in the blend, expressed as equivalents, may vary from 1:1 to 19:1, with optimum properties in the elastomer often resulting from blends with the ratio 2:1 to 4:1.
Inventors
- 👤 David W. House
- 👤 Ray V. Scott, Jr.
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 02:52
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/08; C08G18/10
Claims Analysis
Total Claims: 33
Claim 1
Independent Claim
121 words
A method of curing a polyurethane prepolymer comprising reacting an isocyanate terminated urethane prepolymer, said prepolymer being the adduct of from about 1.5 to about 4.0 equivalents of a polyisocyanate with one equivalent of a polyol, with from about 0.80 to about 1.2 equivalent of a blend comprising a secondary aromatic diamine of the structure, ##STR2## where each of the alkyl groups R 1 and R 2 contains from 1 to about 20 carbon atoms, and a polyhydric alcohol containing more than two reactive hydroxyl groups per molecule, said blend containing from about 1 to about 19 equivalents amine per equivalent polyhydric alcohol, at a temperature between about 75° C. and about 120° C., and recovering the cured polyurethane resulting therefrom.
Claim 2
Independent Claim
121 words
A method of curing a polyurethane prepolymer comprising reacting an isocyanate terminated urethane prepolymer, said prepolymer being the adduct of from about 1.5 to about 4.0 equivalents of a polyisocyanate with one equivalent of a polyol, with from about 0.80 to about 1.2 equivalent of a blend comprising a secondary aromatic diamine of the structure, ##STR2## where each of the alkyl groups R 1 and R 2 contains from 1 to about 20 carbon atoms, and a polyhydric alcohol containing more than two reactive hydroxyl groups per molecule, said blend containing from about 1 to about 19 equivalents amine per equivalent polyhydric alcohol, at a temperature between about 75° C. and about 120° C., and recovering the cured polyurethane resulting therefrom.
Claim 3
Dependent Claim
18 words
The method of claim 1 where the prepolymer is an adduct of a diisocyanate and a dihydric alcohol.
Claim 4
Dependent Claim
14 words
The method of claim 2 where the diisocyanate is toluene diisocyanate or methylenediphenyl diisocyanate.
Claim 5
Dependent Claim
17 words
The method of claim 1 where the alkyl group contains from 1 to about 10 carbon atoms.
Claim 6
Dependent Claim
16 words
The method of claim 4 where the alkyl group contains from 4 to 8 carbon atoms.
Claim 7
Dependent Claim
13 words
The method of claim 1 where the alkyl is a secondary alkyl moiety.
Claim 8
Dependent Claim
13 words
The method of claim 1 where the alkyl group is the 2-butyl group.
Claim 9
Dependent Claim
11 words
The method of claim 1 where the diamine is a N,N'-dialkylmethylene-4,4'-dianiline.
Claim 10
Dependent Claim
10 words
The method of claim 8 where the diamine is N,N'-di(2-butyl)-methylene-4,4'-dianiline.
Claim 11
Dependent Claim
21 words
The method of claim 1 where the polyhydric alcohol is selected from the group consisting of 2,2-di(hydroxymethyl)-1-butanol, N,N,N',N'-tetrakis(2-hydroxypropyl)ethylene diamine, and 2,4,6-tris(N-methyl-N-hydroxymethylaminomethyl)phenol.
Claim 12
Dependent Claim
101 words
A polyurethane resulting from the reaction of an isocyanate terminated urethane prepolymer, said prepolymer being the adduct of from about 1.5 to about 4.0 equivalents of a polyisocyanate with one equivalent of a polyol, with from about 0.80 to about 1.2 equivalent of a blend of a secondary aromatic diamine of the structure, ##STR3## where each of the alkyl groups R 1 and R 2 contains from 1 to about 20 carbon atoms, and a polyhydric alcohol containing more than two reactive hydroxy groups per molecule, said blend containing from about 1 to about 19 equivalents amine pre equivalent polyhydric alcohol.
Claim 13
Dependent Claim
101 words
A polyurethane resulting from the reaction of an isocyanate terminated urethane prepolymer, said prepolymer being the adduct of from about 1.5 to about 4.0 equivalents of a polyisocyanate with one equivalent of a polyol, with from about 0.80 to about 1.2 equivalent of a blend of a secondary aromatic diamine of the structure, ##STR3## where each of the alkyl groups R 1 and R 2 contains from 1 to about 20 carbon atoms, and a polyhydric alcohol containing more than two reactive hydroxy groups per molecule, said blend containing from about 1 to about 19 equivalents amine pre equivalent polyhydric alcohol.
Claim 14
Dependent Claim
18 words
The polyurethane of claim 11 where the prepolymer is an adduct of a diisocyanate and a dihydric alcohol.
Claim 15
Dependent Claim
14 words
The polyurethane of claim 12 where the diisocyanate is toluene diisocyanate or methylenediphenyl diisocyanate.
Claim 16
Dependent Claim
17 words
The polyurethane of claim 11 where the alkyl group contains from 1 to about 10 carbon atoms.
Claim 17
Dependent Claim
16 words
The polyurethane of claim 14 where the alkyl group contains from 4 to 8 carbon atoms.
Claim 18
Dependent Claim
14 words
The polyurethane of claim 11 where the alkyl group is a secondary alkyl moiety.
Claim 19
Dependent Claim
13 words
The polyurethane of claim 11 where the alkyl group is the 2-butyl group.
Claim 20
Dependent Claim
11 words
The polyurethane of claim 11 where the diamine is a N,N'-dialkylmethylene-4,4'-dianiline.
Claim 21
Dependent Claim
11 words
The polyurethane of claim 18 where the diamine is a N,N'-di(2-butyl)-methylene-4,4'-dianiline.
Claim 22
Dependent Claim
21 words
The polyurethane of claim 11 where the polyhydric alcohol is selected from the group consisting of 2,2-di(hydroxymethyl)-1-butanol, N,N,N',N'-tetrakis(2-hydroxypropyl)ethylene diamine, and 2,4,6-tris(N-methyl-N-hydroxymethylaminomethyl)phenol.
Claim 23
Dependent Claim
62 words
A blend for curing urethane prepolymers comprising a secondary aromatic diamine of the structure, ##STR4## where each of the alkyl groups R 1 and R 2 contains from 1 to about 20 carbon atoms, and a polyhydric alcohol containing more than two reactive hydroxyl groups per molecule, the ratio of equivalents of amine to alcohol being from about 1:1 to about 19:1.
Claim 24
Dependent Claim
62 words
A blend for curing urethane prepolymers comprising a secondary aromatic diamine of the structure, ##STR4## where each of the alkyl groups R 1 and R 2 contains from 1 to about 20 carbon atoms, and a polyhydric alcohol containing more than two reactive hydroxyl groups per molecule, the ratio of equivalents of amine to alcohol being from about 1:1 to about 19:1.
Claim 25
Dependent Claim
17 words
The blend of claim 21 where the alkyl group contains from 1 to about 10 carbon atoms.
Claim 26
Dependent Claim
16 words
The blend of claim 22 where the alkyl group contains from 4 to 8 carbon atoms.
Claim 27
Dependent Claim
13 words
The blend of claim 21 where the alkyl is a secondary alkyl moiety.
Claim 28
Dependent Claim
13 words
The blend of claim 21 where the alkyl group is the 2-butyl group.
Claim 29
Dependent Claim
11 words
The blend of claim 21 where the diamine is a N,N'-dialkylmethylene-4,4'-dianiline.
Claim 30
Dependent Claim
10 words
The blend of claim 21 where the diamine is N,N'-di(2-butyl)-methylene-4,4'-dianiline.
Claim 31
Dependent Claim
21 words
The blend of claim 21 where the polyhydric alcohol is selected from the group consisting of 2,2-di(hydroxymethyl)-1-butanol, N,N,N',N'-tetrakis(2-hydroxypropyl)ethylene diamine, and 2,4,6-tris(N-methyl-N-hydroxymethylaminomethyl)phenol.
Claim 32
Dependent Claim
15 words
The blend of claim 21 where the ratio is from about 1.5:1 to about 6:1.
Claim 33
Dependent Claim
15 words
The blend of claim 29 where the ratio is from about 2:1 to about 4:1.
References Cited (Backward Citations)
CA673674A
Cited
US3846351A
Cited
US3891606A
Cited
US3939123A
Cited
US3987012A
Cited
US3997514A
Cited
US4440901A
Cited
US4578446A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1991-01-18 | 1991-07-20 | 1992-01-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-01-18 | 1995-07-20 | 1996-01-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-01-18 | 1999-07-20 | 2000-01-19 | $7700.00 | Window Closed / Lapsed |