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Urea additives for sulfur vulcanizable polymers

Assignee: Goodyear Tire and Rubber Co
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Filing: 1976-01-26
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Granted: 1977-08-16
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Expires: 1996-01-26
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Abstract

Abstract Ureas such as 1,3-bis(morpholinothio)-imidazolidinone are used to affect the vulcanization characteristics of sulfur vulcanizable polymers by increasing the state of vulcanization and 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 2026-11-08 13:31
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/36; C08K5/43

Claims Analysis

Total Claims: 10
Claim 1
Independent Claim 268 words
A sulfur vulcanizable rubber selected from the group consisting of natural rubber and synthetic homopolymers and copolymers of conjugated dienes having incorporated therein 0.25 to 10 parts by weight per 100 parts by weight of rubber of a urea having the following structural formula ##STR7## wherein R is selected from the group consisting of saturated or olefinic divalent aliphatic radicals having 1 to 7 carbon atoms, saturated or olefinic divalent cyclic aliphatic radicals having 5 to 7 carbon atoms, arylene radicals having 6 to 10 carbon atoms and the radical ##STR8## which together with the ##STR9## radical forms a hydantoin ring wherein R 3 and R 4 are selected from the group consisting of hydrogen, alkyl radicals having 1 to 4 carbon atoms, cycloalkyl radicals having 5 to 6 carbon atoms, aralkyl radicals having 7 to 10 carbon atoms and aryl radicals having 6 to 10 carbon atoms or R 3 and R 4 can be joined to form with the attached carbon atom a hydrocarbon ring containing 5 to 6 carbon atoms, and wherein R 1 and R 2 are selected from the group consisting of alkyl radicals having 1 to 20 carbon atoms, cyanoalkyl radicals having 2 to 21 carbon atoms, cycloalkyl radicals having 5 to 20 carbon atoms, aralkyl radicals having 7 to 20 carbon atoms and aryl radicals having 6 to 20 carbon atoms and wherein R 1 and R 2 can be joined through a member of the group consisting of -- CH 2 -- , -- O -- and -- S -- to constitute with the attached nitrogen atom a heterocyclic ring.
Claim 2
Dependent Claim 268 words
A sulfur vulcanizable rubber selected from the group consisting of natural rubber and synthetic homopolymers and copolymers of conjugated dienes having incorporated therein 0.25 to 10 parts by weight per 100 parts by weight of rubber of a urea having the following structural formula ##STR7## wherein R is selected from the group consisting of saturated or olefinic divalent aliphatic radicals having 1 to 7 carbon atoms, saturated or olefinic divalent cyclic aliphatic radicals having 5 to 7 carbon atoms, arylene radicals having 6 to 10 carbon atoms and the radical ##STR8## which together with the ##STR9## radical forms a hydantoin ring wherein R 3 and R 4 are selected from the group consisting of hydrogen, alkyl radicals having 1 to 4 carbon atoms, cycloalkyl radicals having 5 to 6 carbon atoms, aralkyl radicals having 7 to 10 carbon atoms and aryl radicals having 6 to 10 carbon atoms or R 3 and R 4 can be joined to form with the attached carbon atom a hydrocarbon ring containing 5 to 6 carbon atoms, and wherein R 1 and R 2 are selected from the group consisting of alkyl radicals having 1 to 20 carbon atoms, cyanoalkyl radicals having 2 to 21 carbon atoms, cycloalkyl radicals having 5 to 20 carbon atoms, aralkyl radicals having 7 to 20 carbon atoms and aryl radicals having 6 to 20 carbon atoms and wherein R 1 and R 2 can be joined through a member of the group consisting of -- CH 2 -- , -- O -- and -- S -- to constitute with the attached nitrogen atom a heterocyclic ring.
Claim 3
Dependent Claim 18 words
The sulfur vulcanizable polymer according to claim 1 wherein the polymer has incorporated therein an organic accelerating agent.
Claim 4
Dependent Claim 18 words
The sulfur vulcanizable polymer according to claim 1 wherein the polymer has incorporated therein a sulfur vulcanizing agent.
Claim 5
Dependent Claim 25 words
The sulfur vulcanizable polymer according to claim 2 wherein the organic accelerating agent is a primary accelerator and the polymer has incorporated therein elemental sulfur.
Claim 6
Dependent Claim 32 words
The sulfur vulcanizable polymer according to claim 1 wherein the urea is present in the amount of from 0.25 part to 5.0 parts by weight per 100 parts by weight of polymer.
Claim 7
Dependent Claim 51 words
The sulfur vulcanizable polymer according to claim 1 wherein R is selected from the group consisting of ethylene, 1-oxo-2,2-dimethylethylene, 4,5-cyclohexenylene, ortho-phenylene and 1,3-propylene and ##STR10## is selected from the group consisting of morpholino, 2,6-dimethylmorpholino, piperidino, diethylamino, diisopropylamino, 3-methylpiperidino, dicyclohexylamino, N-β-cyanoethylcyclohexylamino, N-β-cyanoethyl-t-butylamino, N-β-cyanoethyl-n-butylamino, N-phenylcyclohexylamino, N-methylanilino, N-ethylanilino, N-ethylbenzylamino, dibenzylamino, N-phenylbenzylamino, N-cyanomethylcyclohexylamino, and N-cyanomethyl-n-butylamino.
Claim 8
Dependent Claim 22 words
The sulfur vulcanizable polymer according to claim 1 wherein the urea is selected from the group consisting of 1,3-bis(morpholinothio)-2-imidazolidinone, 1,3-bis(morpholinothio)-2-benzimidazolinone and 1,3-bis(morpholinothio)-5,5-dimethylhydantoin.
Claim 9
Dependent Claim 33 words
The rubber composition of claim 1 wherein the rubber is selected from the group consisting of butyl rubber, ethylene-propylene terpolymers, copolymers of 1,3-butadiene and styrene, copolymers of 1,3-butadiene and acrylonitrile, and natural rubber.
Claim 10
Dependent Claim 33 words
The rubber composition of claim 7 wherein the rubber is selected from the group consisting of butyl rubber, ethylene-propylene terpolymers, copolymers of 1,3-butadiene and styrene, copolymers of 1,3-butadiene and acrylonitrile, and natural rubber.

References Cited (Backward Citations)

US3427319A Cited
US3473667A Cited
US3838114A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1980-08-15 1981-02-14 1981-08-16 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1984-08-15 1985-02-14 1985-08-16 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1988-08-15 1989-02-14 1989-08-16 $7700.00 Window Closed / Lapsed

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