US5328636A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Rubber vulcanization system containing bis-(2,5-polythio-1,3,4-thiadiazole), bismaleimide and sulfenamide
Assignee: Goodyear Tire and Rubber Co
•
Filing: 1993-07-12
•
Granted: 1994-07-12
•
Expires: 2013-07-12
Abstract
Abstract This invention relates to the discovery that bis-(2,5-polythio-1,3,4-thiadiazole) in combination with a bismaleimide compound and a sulfenamide compound provides for excellent vulcanization of rubbers and results in an improved final rubber vulcanizate possessing superior physical properties and reversion resistance.
Inventors
- 👤 Neil A. Maly
- 👤 Richard M. D'Sidocky
- 👤 Lewis T. Lukich
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 08:32
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3412; C08K5/3415; C08F; C08F279/00; C08F279/02; C08K5/36; C08K5/45
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
237 words
A rubber vulcanization composition comprising: (a) from about 2 to about 15 weight percent of bis- (2,5-polythio-1,3,4-thiadiazole) consisting of the formula: ##STR10## wherein the sum of x and y is from 1 to 16 and x and y are independently selected from 0 and integers of from 1 to 8; (b) from about 15 to about 50 weight percent of a bismaleimide compound of the general formula: ##STR11## wherein R is divalent and is selected from the group consisting of acyclic aliphatic groups having from about 2 to 16 carbon atoms, cyclic aliphatic groups having from about 5 to 20 carbon atom, aromatic group having from about 6 to 18 carbon atoms, and alkylaromatic groups having from about 7 to 24 carbon atoms and wherein these divalent groups may contain a hetero atom selected from 0, N and S; (c) from about 15 to about 45 weight percent of a sulfenamide compound of the general formula: ##STR12## wherein R 1 is selected from the group consisting of hydrogen, acyclic aliphatic groups having from about 1 to 10 carbon atoms, and cyclic aliphatic groups having from about 5 to 10 carbon atoms; and R 2 is selected from the group consisting of cyclic aliphatic groups having from about 5 to 10 carbon atoms and mercaptobenzothiazolyl groups of the formula: ##STR13## and (d) from about 20 to about 55 weight percent of sulfur, a sulfur donor and mixtures thereof.
Claim 2
Dependent Claim
237 words
A rubber vulcanization composition comprising: (a) from about 2 to about 15 weight percent of bis- (2,5-polythio-1,3,4-thiadiazole) consisting of the formula: ##STR10## wherein the sum of x and y is from 1 to 16 and x and y are independently selected from 0 and integers of from 1 to 8; (b) from about 15 to about 50 weight percent of a bismaleimide compound of the general formula: ##STR11## wherein R is divalent and is selected from the group consisting of acyclic aliphatic groups having from about 2 to 16 carbon atoms, cyclic aliphatic groups having from about 5 to 20 carbon atom, aromatic group having from about 6 to 18 carbon atoms, and alkylaromatic groups having from about 7 to 24 carbon atoms and wherein these divalent groups may contain a hetero atom selected from 0, N and S; (c) from about 15 to about 45 weight percent of a sulfenamide compound of the general formula: ##STR12## wherein R 1 is selected from the group consisting of hydrogen, acyclic aliphatic groups having from about 1 to 10 carbon atoms, and cyclic aliphatic groups having from about 5 to 10 carbon atoms; and R 2 is selected from the group consisting of cyclic aliphatic groups having from about 5 to 10 carbon atoms and mercaptobenzothiazolyl groups of the formula: ##STR13## and (d) from about 20 to about 55 weight percent of sulfur, a sulfur donor and mixtures thereof.
Claim 3
Dependent Claim
60 words
The rubber vulcanization composition of claim 1 wherein (a) from about 2.5 to 12.5 weight percent is bis- (2,5-polythio-1,3,4-thiadiazole); (b) from about 20 to 36 weight percent is a bismaleimide compound; (c) from about 17 to 42 weight percent is a sulfenamide compound; and (d) from about 23 to 43 weight percent is sulfur, a sulfur donor, and mixtures thereof.
Claim 4
Dependent Claim
20 words
The rubber vulcanization system of claim 1 wherein x and y are both an integer of from 2 to 4.
Claim 5
Dependent Claim
13 words
The rubber vulcanization system of claim 1 wherein x and y are 2.
Claim 6
Dependent Claim
21 words
The rubber vulcanization system of claim 1 wherein the molecular weight of said bis-(2,5-polythio-1,3,4-thiadiazole) ranges from about 328 to about 808.
Claim 7
Dependent Claim
17 words
The rubber vulcanization system of claim 1 wherein the molecular weight ranges from about 424 to 552.
Claim 8
Dependent Claim
27 words
The rubber vulcanization system of claim 1 wherein said bismaleimide is selected from the group consisting of N,N'-ethylenebismaleimide, N,N'-hexamethylenebismaleimide, N,N'-(m-phenylene)bismaleimide, N,N'-(p-phenylene)bismaleimide, N,N'-(p-tolylene)bismaleimide, N,N'-(methylenedi-p-phenylene)-bismaleimide, N,N'-(oxydi-p-phenylene)bismaleimide, α,α-bis-(4-p-phenylene)bismaleimide, and α,α-bis-(4-maleimidophenyl)-meta-diisopropylbenzene.
Claim 9
Dependent Claim
25 words
The rubber vulcanization system of claim 1 wherein said sulfenamide compound is selected from the group consisting of N-cyclohexyl-2-benzothiazylsulfenamide, N-isopropyl-2-benzothiazylsulfenamide, N-t-butyl-2-benzothiazyl-sulfenamide, N-t-butyl bis-(2-benzothiazylsulfen)amide, and N,N-dicyclohexyl-2-benzothiazylsulfenamide.
Claim 10
Dependent Claim
31 words
The rubber vulcanization system of claim 1 wherein said sulfur and sulfur donor are selected from the group consisting of elemental sulfur, an amide disulfide, polymeric polysulfide and sulfur olefin adducts.
References Cited (Backward Citations)
US3087932A
Cited
GB1235026A
Cited
US3663561A
Cited
US4599425A
Cited
US4960833A
Cited
US4933385A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1997-07-11 | 1998-01-10 | 1998-07-12 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2001-07-11 | 2002-01-10 | 2002-07-12 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2005-07-11 | 2006-01-10 | 2006-07-12 | $7700.00 | Window Closed / Lapsed |