EP0344021A2
Expired / Lapsed
EP
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Para-alkylstyrene/isoolefin copolymers
Assignee: ExxonMobil Chemical Patents Inc
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Filing: 1989-05-26
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Granted: —
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Expires: 2009-05-26
Abstract
Abstract Copolymers which are the direct reaction product of isoolefin having from 4 to 7 carbon atoms and para-alkylstyrene and which have substantially homogeneous compositional distillation are disclosed. These copolymers are preferably copolymers of isobutylene and para-methylstyrene, and preferably at least about 95 wt. % of the copolymer has a para alkylstyrene content within about 10 wt. % of the average para-alkylstyrene content for the overall composition, and even more preferably the normalized differential refractive index and ultraviolet curves obtained by gel permeation chromatography for these copolymers are essentially superimposeable. These copolymers can also be halogenated, and in a particularly preferred aspect of the invention selectively brominated polymers are provided, with almost exclusive substitution taking place on the para-alkyl group, so as to yield a highly desirable benzylic halogen, and preferably bromine, functionality. Methods for producing these copolymers and halogenated copolymers are also disclosed.
Inventors
- 👤 William Kenneth Powers
- 👤 Hsien-Chang Wang
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-10-23 06:54
CPC Classifications
C; C08; C08F; C08F210/00; C08L; C08L23/00; C08L23/26; C08L23/28; C08L23/283; C08F210/04; C08F210/08; C08F210/10; C08F210/14; C08F212/00; C08F212/02; C08F212/04; C08F212/06; C08F212/08; C08F212/12; C08F8/00; C08F8/18; C08F8/20; C08F8/22; C08L71/00; C08L71/08; C08L71/10; C08L71/12; C08L71/123; C08F2800/00; C08F2800/20; C08F2810/00; C08F2810/50; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/582
Claims Analysis
Total Claims: 40
Claim 1
Independent Claim
31 words
A copolymer comprising the direct reaction product of an iso-olefin having from 4 to 7 carbon atoms and a para-alkylstyrene characterised in that said copolymer has a substantially homogeneous compositional distribution.
Claim 2
Dependent Claim
31 words
A copolymer comprising the direct reaction product of an iso-olefin having from 4 to 7 carbon atoms and a para-alkylstyrene characterised in that said copolymer has a substantially homogeneous compositional distribution.
Claim 3
Dependent Claim
29 words
A copolymer according to claim 1 wherein at least 95 wt% of said copolymer has a para-alkylstyrene content within 10 wt% of the average para-alkylstyrene content for said copolymer.
Claim 4
Dependent Claim
29 words
A copolymer according to claim 2 wherein at least 97 wtO/o of said copolymer has a para-alkylstyrene content within 7 wtO/o of the average para-alkylstyrene content for said copolymer.
Claim 5
Dependent Claim
23 words
A copolymer according to any of the preceding claims having a Mw/M N ratio of less than about 6, preferably less than 4.
Claim 6
Dependent Claim
21 words
A copolymer according to claim 4 having a Mw/M N ratio of less than about 2.5 and especially less than 2.0.
Claim 7
Dependent Claim
29 words
A copolymer according to any of the preceding claims wherein the normalized differential refractive index and ultraviolet curves obtained by gel permeation chromatography for said copolymer are essentially superimposeable.
Claim 8
Dependent Claim
46 words
A copolymer according to any of the preceding claims which has M N of at least 25000, preferably greater than 50000 and especially greater than 100000. 8. A copolymer according to any of claims 1 to 6 which has M N of from 500 to 25000.
Claim 9
Dependent Claim
31 words
A copolymer according to any of the preceding claims which comprises from 10 to 99.5 wt% of iso-olefin units and from 0 5 to 90 wt% of the para alkylstyrene units.
Claim 10
Dependent Claim
26 words
A copolymer according to claim 9 which comprises from 80 to 99.5 wt% of the iso-olefin units and from 0.5 to 20 wt% of para-alkylstyrene units.
Claim 11
Dependent Claim
20 words
A copolymer according to any of the preceding claims wherein the iso-olefin comprises isobutylene and/or wherein the para-alkylstyrene comprises para-methylstyrene.
Claim 12
Dependent Claim
45 words
A copolymer according to any of the preceding claims which includes the para-alkylstyrene as wherein R and R' are independently selected from the group consisting of hydrogen, alkyl (preferably C 1 to Cs) and the primary and secondary alkyl (preferably C 1 to Cs) halides.
Claim 13
Dependent Claim
34 words
A copolymer according to any of the preceding claims wherein the ring-bonded carbon atom of the para-alkyl group of at least some of the para-alkylstyrene units carries a directly bondod halogen atom as substituent.
Claim 14
Dependent Claim
42 words
A copolymer according to any of the preceding claims which is substantially free of any ring halogen or any halogen on the polymer backbone chain but which optionally contains halogen in the para-alkyl group of at least some of the para-alkylstyrene units.
Claim 15
Dependent Claim
24 words
A copolymer according to claim 13, or 14 wherein the directly bonded halogen substituent on the ring-bonded carbon of the para-alkyl group is bromine.
Claim 16
Dependent Claim
63 words
A copolymer according to claim 13,14 or 15 which includes the para-alkylstyrene as wherein R and R' are independently selected from the group consisting of hydrogen, alkyl (preferably C 1 to Cs) and primary and secondary alkyl (preferably C 1 to Cs) halides (with R and R' preferably both being hydrogen) and wherein X comprises halogen or a mixture of halogen and hydrogen.
Claim 17
Dependent Claim
39 words
A copolymer according to any of claims 13 to 16 wherein up to 600/ 0 of the para-alkylstyrene units are those having a directly bonded halogen atom substituent, preferably bromine, on the ring-bonded carbon atom of the para-alkyl group.
Claim 18
Dependent Claim
33 words
A copolymer comprising the direct copolymerisation reaction product of an iso-olefin having from 4 to 7 carbon atoms and a para-alkylstyrene, said copolymer having a number average molecular weight of greater than 25000.
Claim 19
Dependent Claim
33 words
A copolymer comprising the direct copolymerisation reaction product of an iso-olefin having from 4 to 7 carbon atoms and a para-alkylstyrene, said copolymer having a number average molecular weight of greater than 25000.
Claim 20
Dependent Claim
70 words
A copolymer according to claim 18 and further characterised by any one or more of the characterising features defined in any claim (a) selected from claims 1 to 7 and 9 to 17, either alone or in combination with any one or more of the characterising features defined in any other one or more of claims 1 to 7 and 9 to 17 on which said claim (a) is dependent.
Claim 21
Dependent Claim
60 words
A halogen containing copolymer of an isoolefin having from 4 to 7 carbon atoms and a para-alkylstyrene characterised in that the ring-bonded carbon of the para-alkyl group of at least some of the para-alkylstyrene units carries a directly bonded halogen atom substituent, said copolymer being (otherwise) substantially free of any ring halogen or any halogen on the polymer backbone chain.
Claim 22
Dependent Claim
60 words
A halogen containing copolymer of an isoolefin having from 4 to 7 carbon atoms and a para-alkylstyrene characterised in that the ring-bonded carbon of the para-alkyl group of at least some of the para-alkylstyrene units carries a directly bonded halogen atom substituent, said copolymer being (otherwise) substantially free of any ring halogen or any halogen on the polymer backbone chain.
Claim 23
Dependent Claim
74 words
A copolymer according to claim 20 which includes the para-alkylstyrene as wherein R and R' are independently selected from the group consisting of hydrogen, alkyl (preferably C 1 to C s ) and the primary and secondary alkyl (preferably C 1 to Cs) halides (R and R' preferably both being hydrogen) wherein X comprises bromine or a mixture of bromine and hydrogen (such mixture preferably containing up to 600/ 0 by number of bromine).
Claim 24
Dependent Claim
70 words
A copolymer according to claim 20 or 21 and further characterised by any one or more of the characterising features defined in any claim (b) selected from claims 1 to 12, 18 and 19, either alone or in combination with any one or more of the characterising features defined in any other one or more of claims 1 to 12, 18 and 19 on which said claim (b) is dependent.
Claim 25
Dependent Claim
64 words
A process for producing a copolymer of an iso-olefin having from 4 to 7 carbon atoms and a para-alkylstyrene which comprises admixing iso-olefin monomer and para-alkylstyrene monomer under copolymerisation conditions in the presence of a diluent and a Lewis Acid catalyst and maintaining the copolymerisation mixture substantially free of impurities which can complex with said catalyst or copolymerise with said iso-olefin or said para-alkylstyrene.
Claim 26
Dependent Claim
64 words
A process for producing a copolymer of an iso-olefin having from 4 to 7 carbon atoms and a para-alkylstyrene which comprises admixing iso-olefin monomer and para-alkylstyrene monomer under copolymerisation conditions in the presence of a diluent and a Lewis Acid catalyst and maintaining the copolymerisation mixture substantially free of impurities which can complex with said catalyst or copolymerise with said iso-olefin or said para-alkylstyrene.
Claim 27
Dependent Claim
17 words
A process according to claim 23 wherein said conditions include a temperature of less than 0° C.
Claim 28
Dependent Claim
21 words
A process according to claim 23 or 24 wherein the catalyst comprises ethyl aluminium dichloride, diethyl aluminium chloride or mixtures thereof.
Claim 29
Dependent Claim
38 words
A process according to claim 23, 24 or 25 in which the copolymer is insoluble in the diluent, being a slurry polymerization process, or in which the copolymer is soluble in the diluent, being a solution polymerization process.
Claim 30
Dependent Claim
45 words
A process according to claim 23, 24 or 25 wherein the copolymer is only slightly soluble in the diluent and the diluent is sufficiently soluble in the copolymer to provide a second phase containing substantially all of said copolymer, being a cement suspension polymerization process.
Claim 31
Dependent Claim
35 words
A process according to any of claims 23 to 27 wherein the diluent is selected from aliphatic hydrocarbons, aromatic hydrocarbons, C 1 to C 6 halogenated hydrocarbons and mixtures of any two or more thereof.
Claim 32
Dependent Claim
24 words
A process according to any of claims 23 to 28 wherein the isobutylono monomer contains no more than 0.5 wt fl of said impurities.
Claim 33
Dependent Claim
40 words
A process according to any of claims 23 to 29 wherein the para-alkylstyrene contains no more than 5 wtO/o, preferably no more than 2.5 wt O /o, and more preferably no more than 0.5 wt O /o of said impurities.
Claim 34
Dependent Claim
28 words
A procedure according to any of claims 23 to 30 wherein the diluent contains no more than 1 wtO/o, preferably no more than 0.2 wt% of said impurities.
Claim 35
Dependent Claim
46 words
A process according to any of claims 23 to 31 including subsequently halogenating said copolymer, optionally by photochemical initiation, preferably using light irradiation of said copolymer in the presence of halogen or by contacting said copolymer with halogen in the presence of a free radical initiator.
Claim 36
Dependent Claim
129 words
A process for selectively halogenating (preferably brominating) a copolymer of an iso-olefin and a para alkylstyrene which comprises providing a copolymer according to any of claims 1 to 22 or produced by the process according to any of claims 23 to 32 which contains para-alkylstyrene units not having a directly bonded halogen atom substituent on the ring-bonded carbon atom of the para-alkyl group, and halogenating (preferably brominating) said copolymer in the presence of halogen and a radical initiator so as to produce a halogenated copolymer wherein the ring-bonded carbon atom of the para-alkyl group of at least some of the para-alkylstyrene units carries a directly bonded halogen (preferably bromine) atom as substituent said copolymer being (otherwise) substantially free of ring halogen or any halogen on the polymer backbone chain.
Claim 37
Dependent Claim
14 words
A process according to claim 33 wherein the radical initiator comprises light and/or heat.
Claim 38
Dependent Claim
49 words
A process according to claim 33 or 34 wherein the radical initiator has a half life of from 5 to 2500 minutes, preferably comprising a bis azo compound and especially such compound selected from azo bis isobutyronitrile, azo bis (2,4 dimethylvalero) nitrile, azo bis (2-methylbutyro) nitrile and mixtures thereof.
Claim 39
Dependent Claim
34 words
A process according to claim 33, 34 or 35 wherein halogenation is terminated before 60% of the para-alkylstyrene has been halogenated, preferably with quenching of the halogenation prior to exhaustion of the halogen therein.
Claim 40
Dependent Claim
23 words
A process according to any of claims 23 to 36 adapted to produce a copolymer according to any of claims 1 to 22.
References Cited (Backward Citations)
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