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US5223599A Expired / Lapsed US ⏱️ 0.0 years remaining

Polyurethane elastomer and non-pneumatic tire fabricated therefrom

Assignee: Uniroyal Chemical Co Inc
•
Filing: 1992-04-10
•
Granted: 1993-06-29
•
Expires: 2012-04-10
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Abstract

Abstract A polyurethane elastomer exhibiting superior flex fatigue properties is obtained by reacting a mixture of isocyanate-terminated polyether prepolymers with at least one alkylthioaromatic amine curing agent. Optionally, the elastomer can be postcured for further improvement of its properties. The polyurethane elastomer can be utilized for the fabrication of a non-pneumatic tire.

Inventors

  • 👤 Vincent J. Gajewski

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-23 12:38
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/08; C08G18/10; C08G18/12; C08G2380/00

Claims Analysis

Total Claims: 60
Claim 1
Independent Claim 86 words
A polyurethane elastomer obtained by reacting (a) a mixture of isocyanate-terminated polyether prepolymers formed from the reaction of (i) a first polyether having a molecular weight of from about 200 to about 1500 and terminated with functional groups containing active hydrogen, (ii) a second polyether having a molecular weight of from above about 1,500 to about 6,500 and terminated with functional groups containing active hydrogen and (iii) a multifunctional isocyanate and (b) alkylthioaromatic amine curing agent having at least two amino groups under polyurethane elastomer-forming conditions.
Claim 2
Dependent Claim 86 words
A polyurethane elastomer obtained by reacting (a) a mixture of isocyanate-terminated polyether prepolymers formed from the reaction of (i) a first polyether having a molecular weight of from about 200 to about 1500 and terminated with functional groups containing active hydrogen, (ii) a second polyether having a molecular weight of from above about 1,500 to about 6,500 and terminated with functional groups containing active hydrogen and (iii) a multifunctional isocyanate and (b) alkylthioaromatic amine curing agent having at least two amino groups under polyurethane elastomer-forming conditions.
Claim 3
Dependent Claim 15 words
The polyurethane elastomer of claim 1 wherein the first and second polyethers are polyether polyols.
Claim 4
Dependent Claim 16 words
The polyurethane elastomer of claim 1 wherein the first and second polyethers are polytetramethylene ether glycols.
Claim 5
Dependent Claim 36 words
The polyurethane elastomer of claim 1 wherein the first polyether has a molecular weight of from about 250 to about 1,000 and the second polyether has a molecular weight of from about 2,000 to about 3,000.
Claim 6
Dependent Claim 28 words
The polyurethane elastomer of claim 1 wherein the first polyether has a molecular weight of about 1,000 and the second polyether has a molecular weight of about 2,000.
Claim 7
Dependent Claim 23 words
The polyurethane elastomer of claim 1 wherein the molar ratio of first polyether to second polyether is from about 95:5 to about 50:50.
Claim 8
Dependent Claim 23 words
The polyurethane elastomer of claim 1 wherein the molar ratio of first polyether to second polyether is from about 90:10 to about 60:40.
Claim 9
Dependent Claim 23 words
The polyurethane elastomer of claim 1 wherein the molar ratio of first polyether to second polyether is from about 85:15 to about 80:20.
Claim 10
Dependent Claim 25 words
The polyurethane elastomer of claim 1 wherein the isocyanate is selected from the group consisting of 2,4 toluene diisocyanate, 2,6 toluene diisocyanate and mixtures thereof.
Claim 11
Dependent Claim 27 words
The polyurethane elastomer of claim 1 wherein the first and second polyethers are polyether polyols and the isocyanate to hydroxyl ratio is from about 1.7:1 to 2.3:1.
Claim 12
Dependent Claim 28 words
The polyurethane elastomer of claim 1 wherein the first and second polyethers are polyether polyols and the isocyanate to hydroxyl ratio is from about 1.85:1 to about 2.1:1.
Claim 13
Dependent Claim 28 words
The polyurethane elastomer of claim 1 wherein the first and second polyethers are polyether polyols and the isocyanate to hydroxyl ratio is from about 1.95:1 to about 2.15:1.
Claim 14
Dependent Claim 31 words
The polyurethane elastomer of claim 1 wherein the alkylthioaromatic amine curing agent possesses at least one aromatic group having thereon at least two alkylthio substituents and at least one amino substituent.
Claim 15
Dependent Claim 60 words
The polyurethane elastomer of claim 1 wherein the alkylthioaromatic amine curing agent possesses the structure ##STR2## wherein R' is the same or different alkyl group; R is the same or different and is hydrogen or other substituent which does not adversely affect polyurethane formation; n is 2 or 3, p is 2 or 3 and q is 1 or 2.
Claim 16
Dependent Claim 34 words
The polyurethane elastomer of claim 1 wherein the alkylthioaromatic amine curing agent possesses the structure ##STR3## wherein R' is a C 1 to C 6 alkyl group, n is 2 and p is 2.
Claim 17
Dependent Claim 52 words
The polyurethane elastomer of claim 1 wherein the alkylthioaromatic amine curing agent is at least one member of the group consisting of 2,4-di(methylthio)-meta-phenylenediamine; 4,6-di(methylthio)-meta-phenylenediamine; 2,4-di(ethylthio)-meta-phenylenediamine; 4,6-di(ethylthio)-meta-phenylenediamine; 2,4-di(n-butylthio)-meta-phenylenediamine; 2,5-di(methylthio)-meta-phenylenediamine; 2-(methylthio)-4-(ethylthio)-meta-phenylenediamine; 3,5-di(methylthio)-2,4-diaminotoluene; 3,5-di(ethylthio)-2,4-diaminotoluene; 3,5-di(methylthio)-2,6-diaminotoluene; 3,5-di(propylthio)-2,4-diaminotoluene; 3-(methylthio)-5-(ethylthio)-2,4-diaminotoluene; 3,5-di(methylthio)-2,4-diamino-ethylbenzene; 3,5-di(ethylthio)-2,6-diamino-ethylbenzene; 3,5-di(cyclohexylthio)-2,4-diaminotoluene; 3-(methylthio)-5-(propylthio)-2,6-diamino-ethylbenzene; 3,5-di(methylthio)-2,4-diamino-chlorobenzene; 3,6-di(ethylthio)-2,4-diamino-chlorobenzene; 4,4'-methylenebis[2,6-di(methylthio)aniline]; [3,5-di(methylthio)-4-aminophenyl[3-(methylthio-4-aminophenyl]methane; 4,4'-ethylidenebis[2,6-di(ethylthio)aniline]; 4,4'-isopropylidenebis[2,6-di(methylthio)aniline]; [3,5-di(methylthio)-4-aminophenyl][3-5-di(ethylthio)-4aminophenyl]sulfide; phenyl[3,5-di(methylthio)-2,4-diaminophenyl]methane; 2,6-diamino-3,5-di(n-butylthio-4-bromotoluene; and, [3,5-di(methylthio)-4-aminophenyl][3,5-di(ethylthio)-4aminophenyl]ether; and, mixtures thereof.
Claim 18
Dependent Claim 19 words
The polyurethane elastomer of claim 1 wherein the alkylthioaromatic amine curing agent is a mixture of 3,5-(methylthio)-2,6-diaminotoluene and 3,5-di(methylthio)-2,6-diaminotoluene.
Claim 19
Dependent Claim 23 words
The polyurethane elastomer of claim 1 wherein the stoichiometry of the mixture of prepolymer to curing agent is from about 80 to 125.
Claim 20
Dependent Claim 23 words
The polyurethane elastomer of claim 1 wherein the stoichiometry of the mixture of prepolymer to curing agent is from 100 to about 120.
Claim 21
Dependent Claim 23 words
The polyurethane elastomer of claim 1 wherein the stoichiometry of the mixture of prepolymer to curing agent is from about 110 to 115.
Claim 22
Dependent Claim 44 words
The polyurethane elastomer of claim 1 wherein the first and second polyethers are polytetramethylene glycols, the isocyanate is selected from the group consisting of 2,4 toluene diisocyanate, 2,6 toluene diisocyanate and mixtures thereof and the curing agent is a mixture of 3,5-di(methylthio)-2,6-diaminotoluene and 3,5-di(methylthio)-2,6-diaminotoluene.
Claim 23
Dependent Claim 10 words
The polyurethane elastomer of claim 1 which has been postcured.
Claim 24
Dependent Claim 21 words
The polyurethane elastomer of claim 1 which has been postcured at a temperature of from about 115° to about 160° C.
Claim 25
Dependent Claim 22 words
The polyurethane elastomer of claim 1 which has been postcured at a temperature of from about 120° C. to about 140° C.
Claim 26
Dependent Claim 10 words
The polyurethane elastomer of claim 21 which has been postcured.
Claim 27
Dependent Claim 22 words
The polyurethane elastomer of claim 21 which has been postcured at a temperature of from about 115° C. to about 140° C.
Claim 28
Dependent Claim 22 words
The polyurethane elastomer of claim 21 which has been postcured at a temperature of from about 120° C. to about 140° C.
Claim 29
Dependent Claim 90 words
A non-pneumatic tire comprising a compression-deformable, load-carrying annular body fabricated from polyurethane elastomer obtained by reacting (a) a mixture of isocyanate-terminated polyether prepolymers formed from the reaction of (i) a first polyether having a molecular weight of from about 200 to about 1500 and terminated with functional groups containing active hydrogen, (ii) a second polyether having a molecular weight of from above about 1,500 to about 6,500 and terminated with functional groups containing active hydrogen and (iii) a multifunctional isocyanate and (b) alkylthioaromatic diamine curing agent under polyurethane elastomer-forming conditions.
Claim 30
Dependent Claim 90 words
A non-pneumatic tire comprising a compression-deformable, load-carrying annular body fabricated from polyurethane elastomer obtained by reacting (a) a mixture of isocyanate-terminated polyether prepolymers formed from the reaction of (i) a first polyether having a molecular weight of from about 200 to about 1500 and terminated with functional groups containing active hydrogen, (ii) a second polyether having a molecular weight of from above about 1,500 to about 6,500 and terminated with functional groups containing active hydrogen and (iii) a multifunctional isocyanate and (b) alkylthioaromatic diamine curing agent under polyurethane elastomer-forming conditions.
Claim 31
Dependent Claim 15 words
The non-pneumatic tire of claim 28 wherein the first and second polyethers are polyether polyols.
Claim 32
Dependent Claim 16 words
The non-pneumatic tire of claim 28 wherein the first and second polyethers are polytetramethylene ether glycols.
Claim 33
Dependent Claim 36 words
The non-pneumatic tire of claim 28 wherein the first polyether has a molecular weight of from about 250 to about 1,000 and the second polyether has a molecular weight of from about 2,000 to about 3,000.
Claim 34
Dependent Claim 28 words
The non-pneumatic tire of claim 28 wherein the first polyether has a molecular weight of about 1,000 and the second polyether has a molecular weight of about 2,000.
Claim 35
Dependent Claim 23 words
The non-pneumatic tire of claim 28 wherein the molar ratio of first polyether to second polyether is from about 95:5 to about 50:50.
Claim 36
Dependent Claim 23 words
The non-pneumatic tire of claim 28 wherein the molar ratio of first polyether to second polyether is from about 90:10 to about 60:40.
Claim 37
Dependent Claim 23 words
The non-pneumatic tire of claim 28 wherein the molar ratio of first polyether to second polyether is from about 85:15 to about 80:20.
Claim 38
Dependent Claim 25 words
The non-pneumatic tire of claim 28 wherein the isocyanate is selected from the group consisting of 2,4 toluene diisocyanate, 2,6 toluene diisocyanate and mixtures thereof.
Claim 39
Dependent Claim 27 words
The non-pneumatic tire of claim 28 wherein the first and second polyethers are polyether polyols and the isocyanate to hydroxyl ratio is from about 1.7:1 to 2.3:1.
Claim 40
Dependent Claim 28 words
The non-pneumatic tire of claim 28 wherein the first and second polyethers are polyether polyols and the isocyanate to hydroxyl ratio is from about 1.85:1 to about 2.1:1.
Claim 41
Dependent Claim 28 words
The non-pneumatic tire of claim 28 wherein the first and second polyethers are polyether polyols and the isocyanate to hydroxyl ratio is from about 1.95:1 to about 2.15:1.
Claim 42
Dependent Claim 31 words
The non-pneumatic tire of claim 28 wherein the alkylthioaromatic amine curing agent possesses at least one aromatic group having thereon at least two alkylthio substituents and at least one amino substituent.
Claim 43
Dependent Claim 60 words
The non-pneumatic tire of claim 28 wherein the alkylthioaromatic amine curing agent possesses the structure ##STR4## wherein R' is the same or different alkyl group; R is the same or different and is hydrogen or other substituent which does not adversely affect polyurethane formation; n is 2 or 3, p is 2 or 3 and q is 1 or 2.
Claim 44
Dependent Claim 34 words
The non-pneumatic tire of claim 28 wherein the alkylthioaromatic amine curing agent possesses the structure ##STR5## wherein R' is a C 1 to C 6 alkyl group, n is 2 and p is 2.
Claim 45
Dependent Claim 52 words
The non-pneumatic tire of claim 28 wherein the alkylthioaromatic amine curing agent is at least one member of the group consisting of 2,4-di(methylthio)-meta-phenylenediamine; 4,6-di(methylthio)-meta-phenylenediamine; 2,4-di(ethylthio)-meta-phenylenediamine; 4,6-di(ethylthio)-meta-phenylenediamine; 2,4-di(n-butylthio)-meta-phenylenediamine; 2,5-di(methylthio)-meta-phenylenediamine; 2-(methylthio)-4-(ethylthio)-meta-phenylenediamine; 3,5-di(methylthio)-2,4-diaminotoluene; 3,5-di(ethylthio)-2,4-diaminotoluene; 3,5-di(methylthio)-2,6-diaminotoluene; 3,5-di(propylthio)-2,4-diaminotoluene; 3-(methylthio)-5-(ethylthio)-2,4-diaminotoluene; 3,5-di(methylthio)-2,4-diamino-ethylbenzene; 3,5-di(ethylthio)-2,6-diamino-ethylbenzene; 3,5-di(cyclohexylthio)-2,4-diaminotoluene; 3-(methylthio)-5-(propylthio)-2,6-diamino-ethylbenzene; 3,5-di(methylthio)-2,4-diamino-chlorobenzene; 3,6-di(ethylthio)-2,4-diamino-chlorobenzene; 4,4'-methylenebis[2,6-di(methylthio)aniline]: [3,5-di(methylthio)-4-aminophenyl[3-(methylthio-4aminophenyl]methane: 4,4'-ethylidenebis[2,6-di(ethylthio)aniline]: 4,4'-isopropylidenebis[2,6-di(methylthio)aniline]; [3,5-di(methylthio)-4-aminophenyl][3-5-di(ethylthio)-4aminophenyl]sulfide: phenyl[3,5-di(methylthio)-2,4-diaminophenyl]methane: 2,6-diamino-3,5-di(n-butylthio-4-bromotoluene: and, [3,5-di(methylthio)-4-aminophenyl][3,5-di(ethylthio)-4aminophenyl]ether: and, mixtures thereof.
Claim 46
Dependent Claim 19 words
The non-pneumatic tire of claim 28 wherein the alkylthioaromatic amine curing agent is a mixture of 3,5-di(methylthio)-2,6-diaminotoluene and 3,5-di(methylthio)-2,6-diaminotoluene.
Claim 47
Dependent Claim 23 words
The non-pneumatic tire of claim 26 wherein the stoichiometry of the mixture of prepolymer to curing agent is from about 80 to 125.
Claim 48
Dependent Claim 23 words
The non-pneumatic tire of claim 26 wherein the stoichiometry of the mixture of prepolymer to curing agent is from 100 to about 120.
Claim 49
Dependent Claim 23 words
The non-pneumatic tire of claim 26 wherein the stoichiometry of the mixture of prepolymer to curing agent is from about 110 to 115.
Claim 50
Dependent Claim 44 words
The non-pneumatic tire of claim 26 wherein the first and second polyethers are polytetramethylene glycols, the isocyanate is selected from the group consisting of 2,4 toluene diisocyanate, 2,6 toluene diisocyanate and mixtures thereof and the curing agent is a mixture of 3,5-di(methylthio)-2,6-diaminotoluene and 3,5-di(methylthio)-2,6-diaminotoluene.
Claim 51
Dependent Claim 13 words
The non-pneumatic tire of claim 28 wherein the polyurethane elastomer has been postcured.
Claim 52
Dependent Claim 25 words
The non-pneumatic tire of claim 28 wherein the polyurethane elastomer has been postcured at a temperature of from about 115° C. to about 160° C.
Claim 53
Dependent Claim 25 words
The non-pneumatic tire of claim 28 wherein the polyurethane elastomer has been postcured at a temperature of from about 120° C. to about 140° C.
Claim 54
Dependent Claim 13 words
The non-pneumatic tire of claim 48 wherein the polyurethane elastomer has been postcured.
Claim 55
Dependent Claim 25 words
The non-pneumatic tire of claim 48 wherein the polyurethane elastomer has been postcured at a temperature of from about 115° C. to about 160° C.
Claim 56
Dependent Claim 25 words
The non-pneumatic tire of claim 48 wherein the polyurethane elastomer has been postcured at a temperature of from about 120° C. to about 140° C.
Claim 57
Dependent Claim 164 words
The non-pneumatic tire of claim 28 wherein the annular body has a generally cylindrical outer member at the other periphery thereof, a generally cylindrical inner member spaced radially inward from, and coaxial with, said outer member, a plurality of axially extending, circumferentially spaced-apart rib members connected at their corresponding inner and outer ends to said inner and outer cylindrical members, said rib members being generally inclined at an angle of from about 0° to about 75° to radial planes which intersect the rib members at their inner ends, and at least one web member having opposite side faces, said web member having its inner and outer peripheries connected respectively to said inner and outer cylindrical members, said web member being connected on at least one of its side faces to at least one of said rib members to thereby form with said rib member a load-carrying structure for said outer cylindrical member, said load-carrying structure being constructed to permit locally loaded members to buckle.
Claim 58
Dependent Claim 164 words
The non-pneumatic tire of claim 55 wherein the annular body has a generally cylindrical outer member at the other periphery thereof, a generally cylindrical inner member spaced radially inward from, and coaxial with, said outer member, a plurality of axially extending, circumferentially spaced-apart rib members connected at their corresponding inner and outer ends to said inner and outer cylindrical members, said rib members being generally inclined at an angle of from about 0° to about 75° to radial planes which intersect the rib members at their inner ends, and at least one web member having opposite side faces, said web member having its inner and outer peripheries connected respectively to said inner and outer cylindrical members, said web member being connected on at least one of its side faces to at least one of said rib members to thereby form with said rib member a load-carrying structure for said outer cylindrical member, said load-carrying structure being constructed to permit locally loaded members to buckle.
Claim 59
Dependent Claim 13 words
The non-pneumatic tire of claim 55 wherein the polyurethane elastomer has been postcured.
Claim 60
Dependent Claim 13 words
The non-pneumatic tire of claim 56 wherein the polyurethane elastomer has been postcured.

References Cited (Backward Citations)

US4595742A Cited
US4975515A Cited
US4934425A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1996-06-28 1996-12-28 1997-06-29 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 2000-06-28 2000-12-28 2001-06-29 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2004-06-28 2004-12-28 2005-06-29 $7700.00 Window Closed / Lapsed

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