US4556702A
Expired / Lapsed
US
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Oligomers and homopolymers of meta- or para-isopropenyl-α,α-dimethylbenzylisocyanate
Assignee: Wyeth Holdings LLC
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Filing: 1983-06-01
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Granted: 1985-12-03
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Expires: 2003-06-01
Abstract
Abstract Aromatic solvent-soluble linear oligomers or homopolymers of meta- or para-isopropenyl-α,α-dimethylbenzylisocyanate characterized by high isocyanate content are disclosed. Such oligomers or homopolymers are made by catalytic solution polymerization of the monomer in methylene chloride and/or toluene solution at a temperature of from about -80° C. to about -25° C., followed by low-temperature neutralization of the polymerization catalyst.
Inventors
- 👤 Frederic C. Schaefer
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 21:53
CPC Classifications
C; C08; C08F; C08F120/00; C08F120/02; C08F120/10; C08F120/12; C08F120/16; C08F120/18; C08G; C08G18/00; C08G18/06; C08G18/70; C08G18/72; C08G18/728; C08F112/00; C08F112/02; C08F112/04; C08F112/14; C08F112/22; C08F112/26
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
93 words
A method of forming oligomers or homopolymers of meta- or para-isopropenyl-α,α-dimethylbenzylisocyanate comprising: (a) solution polymerizing meta- or para-isopropenyl-α,α-dimethylbenzylisocyanate in a solvent selected from the group consisting of methylene chloride, toluene, and mixtures thereof, at a temperature of from about -80° C. to about -25° C. in the presence of a catalytically effective amount of a polymerization catalyst selected from the group consisting of: Bronsted acids and Lewis acids; and (b) neutralizing said polymerization catalyst at a temperature of from about -80° C. to about 10° C., thereby preventing substantial formation of isocyanic acid.
Claim 2
Independent Claim
93 words
A method of forming oligomers or homopolymers of meta- or para-isopropenyl-α,α-dimethylbenzylisocyanate comprising: (a) solution polymerizing meta- or para-isopropenyl-α,α-dimethylbenzylisocyanate in a solvent selected from the group consisting of methylene chloride, toluene, and mixtures thereof, at a temperature of from about -80° C. to about -25° C. in the presence of a catalytically effective amount of a polymerization catalyst selected from the group consisting of: Bronsted acids and Lewis acids; and (b) neutralizing said polymerization catalyst at a temperature of from about -80° C. to about 10° C., thereby preventing substantial formation of isocyanic acid.
Claim 3
Dependent Claim
12 words
A method according to claim 1 wherein said solvent is methylene chloride.
Claim 4
Dependent Claim
46 words
A method according to claim 1 of forming oligomers wherein said polymerization catalyst is anhydrous p-toluenesulfonic acid, said temperature in step (a) is from about -25° C. to about 0° C. and said temperature in step (b) is from about -25° C. to about 5° C.
Claim 5
Dependent Claim
21 words
A method according to claim 3 wherein said catalyst is neutralized by contacting polymerization solution from step (a) with neutral alumina.
Claim 6
Dependent Claim
22 words
A method according to claim 4 wherein said contacting is conducted by flowing said polymerization solution through a column of neutral alumina.
Claim 7
Dependent Claim
27 words
A method according to claim 1 wherein said catalyst is neutralized by addition of a neutralizingly effective amount of pyridine to the polymerization solution from step (a).
Claim 8
Dependent Claim
85 words
A method according to claim 1 wherein: (i) said polymerization catalyst is stannic chloride; (ii) said temperature in step (a) is from about -80° C. to about -20° C.; (iii) said temperature in step (b) is from about -80° C. to -20° C.; (iv) said polymerization catalyst is neutralized by addition of a neutralizingly effective amount of pyridine to the polymerization solution from step (a); and (v) polymerization in step (a) is conducted for a reaction time of from about 3 to about 30 minutes.
Claim 9
Dependent Claim
45 words
A method according to claim 7 of forming homopolymers of peak molecular weight in the range of from about 2,000 to about 12,000, wherein polymerization in step (a) is conducted in the presence of a chain transferringly effective amount of a tertiary benzylic chloride compound.
Claim 10
Dependent Claim
26 words
A method according to claim 8 wherein said polymerization in step (a) is conducted for a reaction time of from about 3 to about 15 minutes.
Claim 11
Dependent Claim
14 words
A method according to claim 8 wherein said tertiary benzylic chloride compound is α-chlorocumene.
Claim 12
Dependent Claim
14 words
A method according to claim 8 wherein said tertiary benzylic chloride compound is tetramethylxylylenedichloride.
Claim 13
Dependent Claim
186 words
A process for forming homopolymers of meta- or para-isopropenyl-α,α-dimethylbenzylisocyanate, comprising: (a) passing a first stream comprising a methylene chloride solution of meta- or para-isopropenyl-α,α-dimethylbenzylisocyanateinto a first reaction zone; (b) concurrently with step (a), passing a second stream comprising a methylene chloride solution of a catalytically effective amount of stannic chloride into said first reaction zone to form therein with said first stream a reaction volume; (c) maintaining said reaction volume under mixing conditions in said first reaction zone at a temperature from about -80° C. to about -25° C. for a time sufficient to polymerize said meta- or para-isopropenyl-α,α-dimethylbenzylisocyanate therein to a predetermined extent; (d) passing a stream of the polymerized reaction volume from said first reaction zone to a second reaction zone; (e) concurrently with step (d) passing to said second reaction zone a third stream comprising a methylene chloride solution containing pyridine in sufficient concentration and at sufficient flow rate of said third stream to neutralize said stannic chloride by complexing of pyridine therewith; (f) discharging neutralized homopolymer-containing solution from said second reaction zone; and (g) recovering said homopolymer from said discharged homopolymer-containing solution.
Claim 14
Dependent Claim
186 words
A process for forming homopolymers of meta- or para-isopropenyl-α,α-dimethylbenzylisocyanate, comprising: (a) passing a first stream comprising a methylene chloride solution of meta- or para-isopropenyl-α,α-dimethylbenzylisocyanateinto a first reaction zone; (b) concurrently with step (a), passing a second stream comprising a methylene chloride solution of a catalytically effective amount of stannic chloride into said first reaction zone to form therein with said first stream a reaction volume; (c) maintaining said reaction volume under mixing conditions in said first reaction zone at a temperature from about -80° C. to about -25° C. for a time sufficient to polymerize said meta- or para-isopropenyl-α,α-dimethylbenzylisocyanate therein to a predetermined extent; (d) passing a stream of the polymerized reaction volume from said first reaction zone to a second reaction zone; (e) concurrently with step (d) passing to said second reaction zone a third stream comprising a methylene chloride solution containing pyridine in sufficient concentration and at sufficient flow rate of said third stream to neutralize said stannic chloride by complexing of pyridine therewith; (f) discharging neutralized homopolymer-containing solution from said second reaction zone; and (g) recovering said homopolymer from said discharged homopolymer-containing solution.
Claim 15
Dependent Claim
48 words
A process according to claim 12 wherein said recovering step (g) comprises: (i) heating said discharged homopolymer-containing solution to a temperature of from about 80° C. to about 120° C. (ii) filtering said heated solution from step (i); and (iii) recovering said homopolymer from the filtered homopolymer solution.
Claim 16
Dependent Claim
25 words
A process according to claim 13 wherein said recovering step (iii) comprises evaporating said filtered homopolymer solution to recover said homopolymer as a residual solid.
Claim 17
Dependent Claim
23 words
A process according to claim 12 wherein said methylene chloride solution of meta- or para-isopropenyl-α,α-dimethylbenzylisocyanate contains a chain transferringly effective amount of α-chlorocumene.
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) | 1988-12-02 | 1989-06-03 | 1989-12-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-12-02 | 1993-06-03 | 1993-12-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-12-02 | 1997-06-03 | 1997-12-03 | $7700.00 | Window Closed / Lapsed |