US4327201A
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Cationically polymerizable macromolecular monomers and graft copolymers therefrom
Assignee: AKRON 302 EAST BUCHTEL AVENUE AKRON OH, University of
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Filing: 1980-10-22
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Granted: 1982-04-27
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Expires: 2000-10-22
Abstract
Abstract The method and production of macromolecular monomers from cationically polymerizable monomers and vinyl-substituted hydrocarbon halides is disclosed. These cationically polymerizable monomers may react in the presence of a catalyst with the hydrocarbon halide to produce a macromer retaining a polymerizable headgroup. This compound may be used in a variety of copolymerization processes with a variety of copolymerizable monomers to form graft copolymers.
Inventors
- 👤 Joseph P. Kennedy
- 👤 Kurt C. Frisch, Jr.
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 00:16
CPC Classifications
C; C08; C08F; C08F291/00; C08F290/00; C08F290/02; C08F290/04; C08F290/044; C08F297/00; C08F297/06
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
99 words
A macromolecular monomer comprising the reaction product of a cationically polymerizable monomer, said monomer being isobutylene, and a vinyl substituted hydrocarbon halide having the formula ##STR5## where R' is a hydrocarbon having from 1 to 18 carbon atoms, and where X is selected from the group consisting of F, Cl, Br, and I, in said reaction the amount of said vinyl substituted hydrocarbon halide is from about 5.0 moles to about 1.0×10 -5 moles per mole of said isobutylene monomer, and wherein said macromolecular monomer has polymerizable head groups, said polymerizable head groups being vinyl or substituted vinyl groups.
Claim 2
Dependent Claim
99 words
A macromolecular monomer comprising the reaction product of a cationically polymerizable monomer, said monomer being isobutylene, and a vinyl substituted hydrocarbon halide having the formula ##STR5## where R' is a hydrocarbon having from 1 to 18 carbon atoms, and where X is selected from the group consisting of F, Cl, Br, and I, in said reaction the amount of said vinyl substituted hydrocarbon halide is from about 5.0 moles to about 1.0×10 -5 moles per mole of said isobutylene monomer, and wherein said macromolecular monomer has polymerizable head groups, said polymerizable head groups being vinyl or substituted vinyl groups.
Claim 3
Dependent Claim
53 words
A macromolecular monomer, according to claim 1, wherein said vinyl-substituted hydrocarbon halide and said isobutylene monomer react in the presence of a cationic polymerization catalyst, said catalysts being a Lewis acid catalyst, said catalyst present in a concentration from about 1.0 moles to about 1.0×10 -5 moles per mole of said isobutylene monomer.
Claim 4
Dependent Claim
46 words
A macromolecular monomer, according to claim 2, wherein reaction occurs at from about +30 degrees C. to about -100 degrees C, wherein said catalyst is selected from the group consisting of trimethylaluminum, triethylaluminum, diethylaluminum chloride, ethylaluminum dichloride, ethylaluminum sesquihalide, diisobutylaluminum chloride, boron trichloride and combinations thereof.
Claim 5
Dependent Claim
15 words
A macromolecular monomer, according to claim 3, wherein said hydrocarbon halide is vinyl benzyl chloride.
Claim 6
Dependent Claim
15 words
A macromolecular monomer according to claim 4, wherein said reaction occurs in a nitrogen atmosphere.
Claim 7
Dependent Claim
30 words
A macromolecular monomer according to claim 5, including carrying out said reaction in the presence of from about 0.0001 to about 0.01 moles of water per mole of said catalyst.
Claim 8
Dependent Claim
12 words
A macromolecular monomer according to claim 6, wherein said catalyst is trimethylaluminum.
Claim 9
Dependent Claim
25 words
A macromolecular monomer according to claim 3, 4, 5, 6, or 7, wherein the number average molecular weight ranges from about 5,000 to about 100,000.
Claim 10
Dependent Claim
62 words
A macromolecular monomer according to claim 3, 4, 5, 6, or 7, wherein in said reaction said vinyl-substituted hydrocarbon halide had a concentration from about 3.0×10 -2 moles to about 5.0×10 -4 moles per mole of said cationically polymerizable monomer, and wherein the amount of said catalyst is from about 0.2 to about 1.0×10 -3 moles per mole of said isobutylene monomer.
Claim 11
Dependent Claim
60 words
A macromolecular monomer, according to claim 3, 4, 5, 6, or 7, wherein in said reaction said vinyl-substituted hydrocarbon halide has a concentration of from about 0.01 to about 5×10 -3 moles per mole of said cationically polymerizable monomer, and wherein the amount of said catalyst is from about 0.1 to about 0.2 moles per mole of said isobutylene monomer.
Claim 12
Independent Claim
130 words
A method for the production of a macromolecular monomer produced by cationic polymerization, comprising: (a) charging from about 5.0 moles to about 1×10 -5 of a vinyl-substituted hydrocarbon halide into a vessel containing about 1 mole of a cationically polymerizable monomer, said monomer being isobutylene, and about 1.0 moles to about 1.0×10 -5 moles of a cationic polymerizing catalyst, said vinyl-substituted hydrocarbon halide having the formula ##STR6## wherein R' is hydrogen or a hydrocarbon having from 1 to 18 carbon atoms, and (b) reacting said hydrocarbon halide and said monomer in the presence of said catalyst at a temperature from about -100° C. to about 30° C. and under N 2 atmosphere to form a cationically prepared macromolecular monomer having a molecular weight of from about 5,000 to about 100,000.
Claim 13
Independent Claim
130 words
A method for the production of a macromolecular monomer produced by cationic polymerization, comprising: (a) charging from about 5.0 moles to about 1×10 -5 of a vinyl-substituted hydrocarbon halide into a vessel containing about 1 mole of a cationically polymerizable monomer, said monomer being isobutylene, and about 1.0 moles to about 1.0×10 -5 moles of a cationic polymerizing catalyst, said vinyl-substituted hydrocarbon halide having the formula ##STR6## wherein R' is hydrogen or a hydrocarbon having from 1 to 18 carbon atoms, and (b) reacting said hydrocarbon halide and said monomer in the presence of said catalyst at a temperature from about -100° C. to about 30° C. and under N 2 atmosphere to form a cationically prepared macromolecular monomer having a molecular weight of from about 5,000 to about 100,000.
Claim 14
Dependent Claim
34 words
A method according to claim 11, wherein said catalyst is selected from the group consisting of trimethylaluminum, tiethylaluminum, trimethylaluminum and water, diethylaluminum chloride, ethylaluminum sesquihalide, ethylaluminum dichloride, diisobutylaluminum chloride, boron trichloride, and combinations thereof.
Claim 15
Dependent Claim
41 words
A macromolecular monomer, comprising: a compound having the formula ##STR7## wherein R' is hydrogen or a hydrocarbon having from 1 to 18 carbon atoms, and wherein said compound has a number average molecular weight of from about 5,000 to about 100,000.
Claim 16
Dependent Claim
41 words
A macromolecular monomer, comprising: a compound having the formula ##STR7## wherein R' is hydrogen or a hydrocarbon having from 1 to 18 carbon atoms, and wherein said compound has a number average molecular weight of from about 5,000 to about 100,000.
Claim 17
Dependent Claim
11 words
A macromolecular monomer according to claim 13, wherein R' is hydrogen.
Claim 18
Dependent Claim
16 words
A method according to claim 12, wherein said vinyl substituted hydrocarbon halide is vinyl benzyl chloride.
Claim 19
Dependent Claim
25 words
A method according to claim 15, including the step of adding from about 0.0001 to about 0.01 moles of water per mole of said catalyst.
Claim 20
Dependent Claim
11 words
A method according to claim 16, wherein said catalyst is trimethylaluminum.
Claim 21
Dependent Claim
56 words
A method according to claim 15, 16, or 17, wherein the amount of said vinyl-substituted hydrocarbon halide ranges from about 3.0×10 -2 moles to about 5.0×10 -4 moles per mole of said isobutylene and wherein the amount of said catalysts ranges from about 0.2 moles to about 1.0×10 -3 moles per mole of said isobutylene monomer.
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