Patent US4229325A successfully refreshed from Google Patents.
US4229325A
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High unsaturation butyl rubbers with additives
Assignee: ExxonMobil Technology and Engineering Co
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Filing: 1978-10-11
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Granted: 1980-10-21
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Expires: 1998-10-11
Abstract
Abstract Substantially gel-free, high unsaturation copolymers of isobutylene and isoprene and high unsaturation terpolymers of isobutylene, isoprene and cyclopentadiene having a number average molecular weight of at least about 90,000 and a mole percent of unsaturation of at least 5% and the process for preparing said polymers which comprises carrying out the polymerization in a homogeneous phase, introducing to the system either an aluminum halide in a soluble form or a hydrocarbylaluminum dihalide and carrying the reaction out at a temperature of less than about -100 DEG C. Vulcanizable compositions are formed from the co- and ter- polymers by reacting them with a vulcanizing amount of sulfur donor and a delayed action accelerator, wherein the vulcanized compositions can be extended with fillers, non-polar process oils and rubbers.
Inventors
- 👤 Warren A. Thaler
- 👤 Donald J. Buckley
- 👤 Kennedy Joseph P.
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 09:23
CPC Classifications
C; C08; C08L; C08L23/00; C08L23/02; C08L23/18; C08L23/20; C08L23/22; C08F; C08F210/00; C08F210/04; C08F210/08; C08F210/10; C08F210/12
Claims Analysis
Total Claims: 48
Claim 1
Independent Claim
100 words
A vulcanizable composition which comprises: (a) a substantially gel free copolymer consisting of a major portion on one isoolefin having about 4 to about 10 carbon atoms and about 5 to about 45 mole % of one conjugated diene having about 5 to about 9 carbon atoms, said copolymer having an Mn from 90,000 to below 120,000, said one isoolefin being selected from the group consisting of isobutylene, 2-methyl-1-butene, 3-methyl-1-butene or 4-methyl-1-pentene, and said diene being selected from the group comprising isoprene, piperylene or methyl cyclopentadiene; (b) a vulcanizing amount of a sulfur donor; and (c) a delayed action accelerator.
Claim 2
Dependent Claim
100 words
A vulcanizable composition which comprises: (a) a substantially gel free copolymer consisting of a major portion on one isoolefin having about 4 to about 10 carbon atoms and about 5 to about 45 mole % of one conjugated diene having about 5 to about 9 carbon atoms, said copolymer having an Mn from 90,000 to below 120,000, said one isoolefin being selected from the group consisting of isobutylene, 2-methyl-1-butene, 3-methyl-1-butene or 4-methyl-1-pentene, and said diene being selected from the group comprising isoprene, piperylene or methyl cyclopentadiene; (b) a vulcanizing amount of a sulfur donor; and (c) a delayed action accelerator.
Claim 3
Dependent Claim
17 words
The composition of claim 1, wherein the isoolefin is isobutylene and the diene is isoprene or piperylene.
Claim 4
Dependent Claim
17 words
The composition of claim 2, wherein the diene content is about 8 to about 40 mole %.
Claim 5
Dependent Claim
15 words
The composition of claim 1, wherein the isoolefin is isobutylene and the diene is methylcyclopentadiene.
Claim 6
Dependent Claim
27 words
The composition of claim 1, wherein the delayed action accelerator is a benzothiazole sulfenamide present at about 0.5 to about 3 wt. % based on the polymer.
Claim 7
Dependent Claim
19 words
The composition of claim 1, wherein a retarder having a pKa value of less than 7 is incorporated therein.
Claim 8
Dependent Claim
18 words
The composition of claim 6, wherein the retarder has a pKa value of about 3 to about 5.
Claim 9
Dependent Claim
18 words
The composition of claim 6, wherein the retarder is N-nitroso diphenylamine, N-cyclohexyl thiophthalimide, phthalic anhydride or salicylic acid.
Claim 10
Dependent Claim
51 words
The composition of claim 1, wherein an activator is included said activator being selected from the group consisting of: (1) oxides, hydroxides and alkoxides of metals of Groups IA and IIA of the Periodic Table of Elements; and (2) organic compounds having a pKa value of about 8 to about 14.
Claim 11
Dependent Claim
15 words
The composition of claim 9, wherein the activator is diphenylquanidine, hexane-1-amine, sodium methoxide or MgO.
Claim 12
Dependent Claim
30 words
The composition of claim 1, wherein the accelerator is N,N-diethylbenzothiazole-2-sulfenamide, N-tertiary butyl benzothiazole-2-sulfenamide, 2-(morpholino) benzothiazole-2-sulfenamide, N,N-diisopropyl benzothiazole-2-sulfenamide, N-cyclohexyl benzothiazole-2-sulfenamide, N,N-dicyclohexyl benzothiazole-2-sulfenamide, 2(2,6 dimethyl morpholino) benzothiazole sulfenamide or 2-piperidinyl benzothiazole sulfenamide.
Claim 13
Dependent Claim
10 words
The composition of claim 1, wherein a retarder is included.
Claim 14
Dependent Claim
25 words
The composition of claim 1, further including a filler at about 5 to about 350 parts by weight per one hundred parts of said polymer.
Claim 15
Dependent Claim
28 words
The composition of claim 1, further including a non-polar process oil at about 5 to about 200 parts by weight based on one hundred parts of said polymer.
Claim 16
Dependent Claim
25 words
The composition of claim 39, further including a filler at about 5 to about 350 parts by weight per one hundred parts of said polymer.
Claim 17
Dependent Claim
30 words
The composition of claim 1, further including an ester plasticizer at a concentration level of about 5 to about 100 parts by weight per one hundred parts of said polymer.
Claim 18
Dependent Claim
25 words
The composition of claim 16, further including a filler at about 5 to about 350 parts by weight per one hundred parts of said polymer.
Claim 19
Dependent Claim
57 words
The composition of claim 1, further including a rubber at a concentration level of about 5 to about 95 parts by weight per one hundred parts of the total of said rubber and said polymer, said rubber being selected from the group consisting of non-polar crystallizable rubbers, polar crystallizable rubbers, non-polar, non-crystallizable rubbers, and polar non-crystallizable rubbers.
Claim 20
Dependent Claim
9 words
The composition of claim 18, further including a filler.
Claim 21
Dependent Claim
9 words
The composition of claim 18, further including an oil.
Claim 22
Dependent Claim
9 words
The composition of claim 19, further including an oil.
Claim 23
Dependent Claim
136 words
A vulcanizable composition which comprises: (a) a substantially gel free terpolymer consisting of a major portion of an isoolefin having about 4 to about 10 carbon atoms and a minor portion of an acyclic conjugated diene having about 5 to about 9 carbon atoms and a cyclic conjugated diene having about 5 to about 9 carbon atoms, a mole % unsaturation of said terpolymer being at least about 8 mole % and an Mn of said terpolymer being from 90,000 to below 120,000, said isoolefin being selected from the group comprising isobutylene, 2-methyl-1-butene, 3-methyl-1-butene or 4-methyl-1-pentene, said acyclic diene being selected from the group comprising isoprene or piperylene, and said cyclic conjugated diene being selected from the group consisting of cyclopentadiene and methylcyclopentadiene; (b) a vulcanizing amount of sulfur donor; and (c) a delayed action accelerator.
Claim 24
Dependent Claim
136 words
A vulcanizable composition which comprises: (a) a substantially gel free terpolymer consisting of a major portion of an isoolefin having about 4 to about 10 carbon atoms and a minor portion of an acyclic conjugated diene having about 5 to about 9 carbon atoms and a cyclic conjugated diene having about 5 to about 9 carbon atoms, a mole % unsaturation of said terpolymer being at least about 8 mole % and an Mn of said terpolymer being from 90,000 to below 120,000, said isoolefin being selected from the group comprising isobutylene, 2-methyl-1-butene, 3-methyl-1-butene or 4-methyl-1-pentene, said acyclic diene being selected from the group comprising isoprene or piperylene, and said cyclic conjugated diene being selected from the group consisting of cyclopentadiene and methylcyclopentadiene; (b) a vulcanizing amount of sulfur donor; and (c) a delayed action accelerator.
Claim 25
Dependent Claim
16 words
The product of claim 22, wherein said isoolefin is isobutylene and said acyclic diene is isoprene.
Claim 26
Dependent Claim
14 words
The product of claims 22 or 23 wherein said cyclic conjugated diene is cyclopentadiene.
Claim 27
Dependent Claim
12 words
The product of claim 22 wherein said cyclic conjugated diene is methylcyclopentadiene.
Claim 28
Dependent Claim
22 words
The product of claims 22, or 23, wherein said terpolymer contains at least about 8 mole % of said cyclic conjugated diene.
Claim 29
Dependent Claim
18 words
The composition of claim 22, wherein the isoolefin is isobutylene and the acyclic diene is isoprene or piperylene.
Claim 30
Dependent Claim
16 words
The composition of claim 22, wherein the isoolefin is isobutylene and the cyclic diene is methylcyclopentadiene.
Claim 31
Dependent Claim
17 words
The composition of claim 22, wherein the diene content is about 8 to about 40 mole %.
Claim 32
Dependent Claim
27 words
The composition of claim 22, wherein the delayed action accelerator is a benzothiazole sulfenamide present at about 0.5 to about 3 wt. % based on the polymer.
Claim 33
Dependent Claim
19 words
The composition of claim 22, wherein a retarder having a pKa value of less than 7 is incorporated therein.
Claim 34
Dependent Claim
51 words
The composition of claim 22, wherein an activator is included said activator being selected from the group consisting of: (1) oxides, hydroxides and alkoxides of metals of Groups IA and IIA of the Periodic Table of Elements; and (2) organic compounds having a pKa value of about 8 to about 14.
Claim 35
Dependent Claim
18 words
The composition of claim 31, wherein the retarder has a pKa value of about 3 to about 5.
Claim 36
Dependent Claim
29 words
The composition of claim 22, wherein the accelerator is N,N-diethylbenzothiazole-2-sulfenamide, N-tertiary butyl benzothiazole-2-sulfenamide, 2-(morpholino)benzothiazole-2-sulfenamide, N,N-diisopropyl benzothiazole-2-sulfenamide, N-cyclohexyl benzothiazole-2-sulfenamide, N,N-dicyclohexyl benzothiazole-2-sulfenamide, 2(2,6 dimethyl morpholino) benzothiazole sulfenamide or 2-piperidinyl benzothiazole sulfenamide.
Claim 37
Dependent Claim
18 words
The composition of claim 31, wherein the retarder is N-nitroso diphenylamine, N-cyclohexyl thiophthalimide, phthalic anhydride or salicyclic acid.
Claim 38
Dependent Claim
15 words
The composition of claim 32, wherein the activator is diphenylquanidine, hexane-1-amine, sodium methoxide or MgO.
Claim 39
Dependent Claim
10 words
The composition of claim 22, wherein a retarder is included.
Claim 40
Dependent Claim
25 words
The composition of claim 22, further including a filler at about 5 to about 350 parts by weight per one hundred parts of said polymer.
Claim 41
Dependent Claim
28 words
The composition of claim 22, further including a non-polar process oil at about 5 to about 200 parts by weight based on one hundred parts of said polymer.
Claim 42
Dependent Claim
25 words
The composition of claim 39, further including a filler at about 5 to about 350 parts by weight per one hundred parts of said polymer.
Claim 43
Dependent Claim
30 words
The composition of claim 22, further including an ester plasticizer at a concentration level of about 5 to about 100 parts by weight per one hundred parts of said polymer.
Claim 44
Dependent Claim
25 words
The composition of claim 41, further including a filler at about 5 to about 350 parts by weight per one hundred parts of said polymer.
Claim 45
Dependent Claim
57 words
The composition of claim 22, further including a rubber at a concentration level of about 5 to about 95 parts by weight per one hundred parts of the total of said rubber and said polymer, said rubber being selected from the group consisting of non-polar crystallizable rubbers, polar crystallizable rubbers, non-polar, non-crystallizable rubbers, and polar non-crystallizable rubbers.
Claim 46
Dependent Claim
9 words
The composition of claim 43, further including a filler.
Claim 47
Dependent Claim
9 words
The composition of claim 44, further including an oil.
Claim 48
Dependent Claim
9 words
The composition of claim 43, further including an oil.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-10-21 | 1984-04-21 | 1984-10-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-10-21 | 1988-04-21 | 1988-10-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-10-21 | 1992-04-21 | 1992-10-21 | $7700.00 | Window Closed / Lapsed |