US4278585A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Rubber compositions
Assignee: Phillips Petroleum Co
•
Filing: 1979-07-31
•
Granted: 1981-07-14
•
Expires: 1999-07-31
Abstract
Abstract This invention relates to novel sulfur-containing organosilicon compounds comprising substituted dithiocarbamates and substituted sulfenate esters and the use of these novel compounds as reinforcing promoters for silica-filled rubber compositions.
Inventors
- 👤 Carl J. Stacy
- 👤 Rector P. Louthan
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 12:05
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/54; C08K5/548
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
104 words
A silica-containing vulcanizable composition comprising: (a) a vulcanizable natural or synthetic rubber; (b) a siliceous filler; and (c) at least one sulfur-containing organosilicon compound of the formulas ##STR2## wherein R' is a hydrocarbon radical of 1 to 10, inclusive, carbon atoms, R, R" and R"' are selected from R' and hydrogen, R" and R"' can be linked together and form with the nitrogen atom a cyclic structure, Q is alkylene, cycloalkylene, arylene, or combinations thereof having from 1 to about 10, inclusive, carbon atoms, and n is 0, 1, or 2, said organosilicon compound increasing the bonding of said siliceous filler to said rubber.
Claim 2
Dependent Claim
104 words
A silica-containing vulcanizable composition comprising: (a) a vulcanizable natural or synthetic rubber; (b) a siliceous filler; and (c) at least one sulfur-containing organosilicon compound of the formulas ##STR2## wherein R' is a hydrocarbon radical of 1 to 10, inclusive, carbon atoms, R, R" and R"' are selected from R' and hydrogen, R" and R"' can be linked together and form with the nitrogen atom a cyclic structure, Q is alkylene, cycloalkylene, arylene, or combinations thereof having from 1 to about 10, inclusive, carbon atoms, and n is 0, 1, or 2, said organosilicon compound increasing the bonding of said siliceous filler to said rubber.
Claim 3
Dependent Claim
10 words
The product obtained by curing the composition of claim 1.
Claim 4
Dependent Claim
15 words
A composition according to claim 1 wherein (a) is a polymer of a conjugated diene.
Claim 5
Dependent Claim
23 words
A composition according to claim 1 wherein (a) is a sulfur curable polymer and the composition includes sulfur or a sulfur yielding material.
Claim 6
Dependent Claim
6 words
A cured product of claim 4.
Claim 7
Dependent Claim
18 words
A composition according to claim 1 including sulfur, a cure accelerator, processing aids and light and ozone stabilizers.
Claim 8
Dependent Claim
41 words
A composition according to claim 1 wherein based upon 100 parts of (a), the amount of (b) present ranges from about 5 to about 150 parts and the amount of (c) ranges from about 0.05 to about 10 parts by weight.
Claim 9
Dependent Claim
19 words
A composition according to claim 1 wherein (a) is a butadiene/styrene copolymer and (b) is a precipitated hydrated silica.
Claim 10
Dependent Claim
25 words
A composition according to claim 1 wherein (a) is a butadiene/styrene copolymer, (b) is silica and (c) is 3-(trimethoxysilyl)propylsulfenyl dimethyldithiocarbamate, methyl 3-(trimethoxysilyl)propylsulfenate, or ethyl 3-(trimethoxysilyl)propylsulfenate.
Claim 11
Dependent Claim
18 words
A composition according to claim 9 including sulfur, a cure accelerator, processing aids and light and ozone stabilizers.
Claim 12
Dependent Claim
86 words
A compound suitable for use as coupling agents or promoters in the silica filler reinforcement of a rubber represented by the formula ##STR3## wherein R' is a hydrocarbon radical of 1 to 10, inclusive, carbon atoms, R, R" and R"' are selected from R' and hydrogen, R" and R"' can be linked together and form with the nitrogen atom a cyclic structure, Q is alkylene, cycloalkylene, arylene, or combinations thereof having from 1 to about 10, inclusive, carbon atoms, and n is 0, 1, or 2.
Claim 13
Dependent Claim
86 words
A compound suitable for use as coupling agents or promoters in the silica filler reinforcement of a rubber represented by the formula ##STR3## wherein R' is a hydrocarbon radical of 1 to 10, inclusive, carbon atoms, R, R" and R"' are selected from R' and hydrogen, R" and R"' can be linked together and form with the nitrogen atom a cyclic structure, Q is alkylene, cycloalkylene, arylene, or combinations thereof having from 1 to about 10, inclusive, carbon atoms, and n is 0, 1, or 2.
Claim 14
Dependent Claim
10 words
A compound according to claim 11 which is 3-(trimethoxysilyl)propylsulfenyl dimethyldithiocarbamate.
Claim 15
Dependent Claim
45 words
A process for enhancing the effectiveness of silica-containing materials as reinforcing fillers in vulcanizable rubber compositions which comprises effectively bonding said silica-containing material to the rubber by incorporating therein a reinforcing amount of at least one compound of claim 11 and curing the resulting composition.
Claim 16
Dependent Claim
27 words
A process according to claim 3 wherein said promoting amount ranges from about 0.05 to about 10 parts by weight per hundred parts by weight of rubber.
Claim 17
Dependent Claim
13 words
A process according to claim 14 wherein said promoting agent is 3-(trimethoxysilyl)propylsulfenyl dithiocarbamate.
Claim 18
Dependent Claim
55 words
A process for producing a compound as defined in claim 11 which comprises allowing a (mercaptoalkyl)trihydrocarbyloxysilane to react with a chlorinating agent and then allowing the resulting product to react with the product resulting from the reaction of carbon disulfide and a dihydrocarbyl or cyclic secondary amine under ambient conditions and in an inert atmosphere.
References Cited (Backward Citations)
US3170940A
Cited
US3362978A
Cited
US3798196A
Cited
US3947436A
Cited
US3873489A
Cited
US3957718A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-07-13 | 1985-01-12 | 1985-07-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-07-13 | 1989-01-12 | 1989-07-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-07-13 | 1993-01-12 | 1993-07-14 | $7700.00 | Window Closed / Lapsed |