Patent US4110319A successfully refreshed from Google Patents.
US4110319A
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US
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Thiocarbamate additives for sulfur vulcanizable polymers
Assignee: Goodyear Tire and Rubber Co
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Filing: 1976-10-01
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Granted: 1978-08-29
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Expires: 1996-10-01
Abstract
Abstract Thiocarbamates such as N,N-oxydiethylenecarbamyl 1-dodecyl disulfide are used to affect the vulcanization characteristics of sulfur vulcanizable polymers by increasing the state of vulcanization and/or improving scorch resistance and/or increasing the rate of vulcanization.
Inventors
- 👤 John P. Lawrence
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 09:32
CPC Classifications
C; C07; C07D; C07D295/00; C07D295/16; C07D295/20; C07D295/21; C08; C08K; C08K5/00; C08K5/36; C08K5/39
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
346 words
A sulfur vulcanizable diene polymer selected from the group consisting of natural rubber and synthetic diene polymers prepared from a monomer system containing diene monomer, said sulfur vulcanizable diene polymer having incorporated therein at least one thiocarbamate having the following structural formula ##STR4## wherein R is selected from the group consisting of alkyl radicals having 1 to 20 carbon atoms, monochloroalkyl radicals having 3 to 20 carbon atoms, cycloalkyl radicals having 5 to 10 carbon atoms, monochlorocycloalkyl radicals having 5 to 10 carbon atoms, aralkyl radicals having 7 to 11 carbon atoms and aryl radicals having 6 to 10 carbon atoms, said aryl radicals optionally substituted with 1 or 2 radicals selected from the group consisting of alkyl radicals having 1 to 4 carbon atoms and the chloro radical, wherein the symbol ##STR5## denotes a heterocyclic amino radical selected from the group consisting of pyrrolidino, piperidino, hexamethyleneimino, morpholino, 2,6-dimethylmorpholino, 2-methylpiperidino, 3-methylpiperidino, 4-methylpiperidino, 2,6-dimethylpiperidino, and 4-methylpiperazino, R 2 is selected from the group consisting of alkylene radicals conforming to the following structural formula --(C.sub.m H.sub.2m) -- (R.sup.6).sub.X -- (C.sub.n H.sub.2n) -- and arylene radicals having 6 to 10 carbon atoms, wherein X is 0 or 1, wherein R 6 is selected from the group consisting of --0--, --S-- and phenylene, wherein when R 6 is phenylene or X is 0, m and n are positive whole numbers from 1 to 5 and wherein when R 6 is --0-- or --S--, m and n are positive whole numbers from 2 to 5; R 3 and R 4 are selected from the group consisting of alkyl radicals having 1 to 20 carbon atoms, cyclohexyl radical; aralkyl radicals having 7 to 12 carbon atoms and aryl radicals having 6 to 10 carbon atoms; R 5 is selected from the group consisting of alkylene radicals having 2 to 6 carbon atoms and p-phenylene and wherein R 3 and R 4 can be joined to constitute with the bridging R 5 group and the attached nitrogen atoms, a heterocyclic diamino radical selected from the group consisting of piperazino, 2,5-dimethylpiperazino, homopiperazino, and 4,4'-trimethylenediperidino.
Claim 2
Dependent Claim
346 words
A sulfur vulcanizable diene polymer selected from the group consisting of natural rubber and synthetic diene polymers prepared from a monomer system containing diene monomer, said sulfur vulcanizable diene polymer having incorporated therein at least one thiocarbamate having the following structural formula ##STR4## wherein R is selected from the group consisting of alkyl radicals having 1 to 20 carbon atoms, monochloroalkyl radicals having 3 to 20 carbon atoms, cycloalkyl radicals having 5 to 10 carbon atoms, monochlorocycloalkyl radicals having 5 to 10 carbon atoms, aralkyl radicals having 7 to 11 carbon atoms and aryl radicals having 6 to 10 carbon atoms, said aryl radicals optionally substituted with 1 or 2 radicals selected from the group consisting of alkyl radicals having 1 to 4 carbon atoms and the chloro radical, wherein the symbol ##STR5## denotes a heterocyclic amino radical selected from the group consisting of pyrrolidino, piperidino, hexamethyleneimino, morpholino, 2,6-dimethylmorpholino, 2-methylpiperidino, 3-methylpiperidino, 4-methylpiperidino, 2,6-dimethylpiperidino, and 4-methylpiperazino, R 2 is selected from the group consisting of alkylene radicals conforming to the following structural formula --(C.sub.m H.sub.2m) -- (R.sup.6).sub.X -- (C.sub.n H.sub.2n) -- and arylene radicals having 6 to 10 carbon atoms, wherein X is 0 or 1, wherein R 6 is selected from the group consisting of --0--, --S-- and phenylene, wherein when R 6 is phenylene or X is 0, m and n are positive whole numbers from 1 to 5 and wherein when R 6 is --0-- or --S--, m and n are positive whole numbers from 2 to 5; R 3 and R 4 are selected from the group consisting of alkyl radicals having 1 to 20 carbon atoms, cyclohexyl radical; aralkyl radicals having 7 to 12 carbon atoms and aryl radicals having 6 to 10 carbon atoms; R 5 is selected from the group consisting of alkylene radicals having 2 to 6 carbon atoms and p-phenylene and wherein R 3 and R 4 can be joined to constitute with the bridging R 5 group and the attached nitrogen atoms, a heterocyclic diamino radical selected from the group consisting of piperazino, 2,5-dimethylpiperazino, homopiperazino, and 4,4'-trimethylenediperidino.
Claim 3
Dependent Claim
126 words
The sulfur vulcanizable diene polymer according to claim 1 wherein R is selected from the group consisting of ethyl, 1-propyl, 2-propyl, 1-butyl, 1-hexyl, 1-octyl, 1-dodecyl, cyclohexyl, benzyl, phenyl, 2-chlorocyclohexyl, 1-(2-chlorobutyl), 2-(1-chlorobutyl), 1-(2-chloropropyl), 2-(1-chloropropyl), 2-(3-chlorobutyl), and 2-(3-chloro-2,2,1-bicycloheptyl, R 3 and R 4 are selected from the group consisting of methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, cyclohexyl, benzyl and phenyl, the ##STR6## ring is morpholino or piperidino, R 2 is selected from the group consisting of 1,2-ethylene, 1,2-propylene, 1,3-tetramethylene, 1,6-hexamethylene, 1,8-octamethylene and 2,2'-oxydiethylene, R 5 is selected from the group consisting of 1,2-ethylene, 1,3-propylene and p-phenylene, and when R 3 and R 4 are joined with the two nitrogen atoms and the bridging group R 5 the ring is selected from the group consisting of piperazino, 2,5-dimethylpiperazino and 4,4'-trimethylenediperidino.
Claim 4
Dependent Claim
19 words
The sulfur vulcanizable diene polymer according to claim 1 wherein the polymer has incorporated therein an organic accelerating agent.
Claim 5
Dependent Claim
19 words
The sulfur vulcanizable diene polymer according to claim 1 wherein the polymer has incorporated therein a sulfur vulcanizing agent.
Claim 6
Dependent Claim
26 words
The sulfur vulcanizable diene polymer according to claim 3 wherein the organic accelerating agent is a primary accelerator and the polymer has incorporated therein elemental sulfur.
Claim 7
Dependent Claim
33 words
The sulfur vulcanizable diene polymer according to claim 1 wherein the thiocarbamate is present in the amount of from 0.25 part to 5.0 parts by weight per 100 parts by weight of polymer.
Claim 8
Dependent Claim
44 words
The sulfur vulcanizable diene polymer according to claim 1 wherein the polymer is selected from the group consisting of natural rubber, polychloroprene, cis-1,4-polybutadiene, cis-1,4 polyisoprene, butyl rubber, copolymers of butadiene and styrene, copolymers of butadiene and acrylonitrile and terpolymers of ethylene, propylene and dicyclopentadiene.
Claim 9
Dependent Claim
15 words
The sulfur vulcanizable diene polymer according to claim 1 wherein the group ##STR7## is morpholino.
References Cited (Backward Citations)
US3790534A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-08-28 | 1982-02-27 | 1982-08-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-08-28 | 1986-02-27 | 1986-08-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-08-28 | 1990-02-27 | 1990-08-29 | $7700.00 | Window Closed / Lapsed |