Patent EP0130322A2 successfully refreshed from Google Patents.
EP0130322A2
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EP
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Emulsion copolymerisation of meta- or para-isopropenyl-alpha,alpha-dimethylbenzylisocyanate
Assignee: Wyeth Holdings LLC
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Filing: 1984-05-12
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Granted: —
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Expires: 2004-05-12
Abstract
Abstract A method of making a copolymer of meta- or para- isopropenyl-a,a-dimethylbenzylisocyanate and at least one other ethylenically unsaturated comonomer polymerizable therewith, comprising polymerizing the meta- or para- isopropenyl-a,a-dimethylbenzylisocyanate and at least one other ethylenically unsaturated comonomer in an aqueous emulsion in the presence of a free-radical polymerization initiator and a chain transfer agent to control molecular weight. Also disclosed are methods of breaking the aqueous emulsion after polymerization is completed by either adding a salt, e.g., aluminum sulfate, or by freezing the emulsion followed by thawing to yield the copolymer as a mechanically separable solid phase of a two-phase liquid-solid mixture.
Inventors
- 👤 Robin William Dexter
- 👤 Peter Salvatore Forgione
- 👤 John A. Sedlak
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-10-29 20:44
CPC Classifications
C; C08; C08F; C08F22/00; C08F22/10; C08F22/12; C08F22/18; C08F6/00; C08F6/14; C08F6/22; C08F212/00; C08F212/02; C08F212/04; C08F212/14; C08F212/26; C08G; C08G18/00; C08G18/06; C08G18/70; C08G18/72; C08G18/728
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
52 words
A method of making a copolymer of mela- or para-isopropenyl-α,α-dimethylbenzylisocyanate and at least one other ethylenically unsaturated comonomer polymerizable therewith, comprising polymerizing said meta- or para- isopropenyl-a,a-dimethylbenzylisocyanate and at least one other ethylenically unsaturated comonomer in an aqueous emulsion in the presence of a free-radical polymerization initiator and a chain transfer agent.
Claim 2
Independent Claim
52 words
A method of making a copolymer of mela- or para-isopropenyl-α,α-dimethylbenzylisocyanate and at least one other ethylenically unsaturated comonomer polymerizable therewith, comprising polymerizing said meta- or para- isopropenyl-a,a-dimethylbenzylisocyanate and at least one other ethylenically unsaturated comonomer in an aqueous emulsion in the presence of a free-radical polymerization initiator and a chain transfer agent.
Claim 3
Dependent Claim
28 words
A method according to Claim 1, wherein said at least one ethylenically unsaturated comonomer is butyl acrylate, methyl acrylate, methyl methacrylate, ethyl acrylate, styrene, a-methylstyrene, p-methyl-a-methylstyrene, or p-methylstyrene.
Claim 4
Dependent Claim
46 words
A method according to Claim 1 wherein said copolymer contains from about 5 to about 80 mole percent repeating units derived from meta- or para-isopropenyl-a,a-dimethylbenzylisocyanate and from about 20 to about 95 mole percent repeating units derived from said at least one other ethylenically unsaturated comonomer.
Claim 5
Independent Claim
20 words
A method according to Claim I wherein said free-radical polymerization initiator is an admixture of potassium persulfate and sodium metabisulphite.
Claim 6
Dependent Claim
45 words
A method according to Claim 1 wherein said chain transfer agent is a water insoluble mercaptan dodecyl mercaptan or n-octyl thiol and is present in said polymerization in an amount of from about 0.2 to about 10 mole percent based on the weight of monomer.
Claim 7
Independent Claim
22 words
A method according to Claim I wherein said polymerization is carried out at a temperature of from about 25°C to about 60°C.
Claim 8
Dependent Claim
20 words
A copolymer produced by the method of Claim 1, having a molecular weight of from about 2,000 to about 70,000.
Claim 9
Dependent Claim
75 words
A copolymer according to Claim 7, containing from about 5 to about 80 mole percent repeating units derived from meta- or para-isopropenyl-α,α-dimethylbenzylisocyanate and from about- 20 to about 95 mole percent repeating units derived from at least one other ethylenically unsaturated comonomer polymerizable therewith selected from the group consisting of butyl acrylate, methyl acrylate, methyl methacrylate, ethyl acrylate, styrene, a-methylstyrene, p-methyl-a-methylstyrene, and p-methylstyrene and having a molecular weight of from about 2,000 to about 70,000.
Claim 10
Dependent Claim
49 words
A copolymer according to Claim 7, containing from about 5 to about 25 mole percent repeating units derived from meta- or para-isopropenyl-a,a-dimethylbenzylisocyanate and from about 75 to about 95 mole percent repeating units derived from methyl methacrylate and having a molecular weight of from about 5,000 to about 10,000.
Claim 11
Dependent Claim
51 words
A copolymer according to Claim 7, containing from about 5 to about 15 mole percent repeating units derived from meta- or para-isopropenyl-a,a-dimethylbenzylisocyanate, from about 20 to about 40 mole percent repeating units derived from methyl methacrylate, and from about 50 to about 70 mole percent repeating units derived from butyl acrylate.
Claim 12
Dependent Claim
127 words
A method according to Claim 1 for forming a substantially homogeneous copolymer of meta- or para-isopropenyl-α, a-dimethylbenzylisocyanate, and at least one other ethylenically unsaturated comonomer polymerizable therewith selected from the group consisting of butyl acrylate, methyl acrylate, methyl methacrylate, ethyl acrylate, styrene, a-methylstyrene, p-methyl-a-methylstyrene and p-methylstyrene, comprising: (a) forming a reaction volume comprising water, free-radical polymerization initiator, chain transfer agent and such one of said other ethylenically unsaturated comonomers to be incorporated into said copolymer as has the lowest reactivity thereof; and (b) adding meta- or para-isopropenyl-a,a-dimethylbenzylisocyanate and other remaining comonomers to be incorporated into said copolymer continuously to said reaction volume under emulsion polymerization reaction conditions while maintaining a constant monomeric composition in said reaction volume, to form said copolymer with a substantially homogeneous polymeric composition.
Claim 13
Dependent Claim
20 words
A copolymer produced by the method of Claim 9, having a molecular weight of from about 2,000 to about 70,000.
Claim 14
Dependent Claim
27 words
A coating composition comprising a copolymer according to Claim 7 and a curative comprising a cross-linkingly effective amount of a compound with free hydroxyl or amine functionality.
Claim 15
Dependent Claim
19 words
A coating composition according to Claim 10 wherein said curative compound is trimethylolpropane, ethylenediamine ketimine, diethylene glycol or 1,2,6-hexanetriol.
Claim 16
Dependent Claim
32 words
A method of forming a coating on a substrate, comprising applying to said substrate a film of a coating composition according to Claim 10, and curing same in the presence of moisture.
Claim 17
Dependent Claim
42 words
A method according to Claim 1, further including isolating said copolymer from said aqueous emulsion after polymerization has proceeded to a desired extent, comprising adding to said aqueous emulsion a salt consisting of calcium chloride, sodium chloride, aluminum sulfate, or sodium sulfate.
Claim 18
Dependent Claim
71 words
A method according to Claim 1, further including isolating said copolymer from said aqueous emulsion after polymerization has proceeded to a desired extent, comprising: (a) freezing said aqueous emulsion to a frozen solid to thereby break said aqueous emulsion, (b) thawing said frozen solid to yield a two-phase mixture comprising a reliquified aqueous phase and said copolymer as a solid phase, and (c) separating said copolymer from said reliquified aqueous phase.
Claim 19
Dependent Claim
35 words
A method according to Claim 17 wherein said copolymer is separated in step (c) by filtration of said two-phase mixture and thereafter is vacuum dried at a temperature of from about 25°C to about 40°C.
References Cited (Backward Citations)
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