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US4675414A
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Maleimidomethyl-carbonate polyethers
Assignee: United States Department of the Navy
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Filing: 1985-03-08
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Granted: 1987-06-23
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Expires: 2005-03-08
Abstract
Abstract Aliphatic polyethers having at least two N-methylmaleimide groups chemica joined thereto by a carbonate linkage are provided and a method for making such compounds. The hydroxy-terminated aliphatic polyether, such as polypropylene glycol, is initially reacted with carbonyl chloride to form the chloroformate. The polyether chloroformate derivative is then reacted with N-hydroxymethylmaleimide yielding the bis or tris(maleimidomethyl)carbonate of said polyether.
Inventors
- 👤 Albert A. DeFusco
- 👤 Eugene C. Martin
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 07:57
CPC Classifications
C; C07; C07D; C07D207/00; C07D207/02; C07D207/44; C07D207/444; C07D207/448; C07D207/452; C08; C08G; C08G65/00; C08G65/02; C08G65/32; C08G65/321; C08G65/324; C08G65/329; C08G65/333; C08G65/33331; C08G65/33337; C08G65/338
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
132 words
A method for the preparation of maleimidomethyl carbonate terminated polyalkylene oxides of the formula: ##STR3## where n is from 6 to 7, said method comprising: adding a solution of carbonyl chloride at -3° C. to a solution of a polyalkylene oxide at -3° C.; stirring said reaction mixture for about 12 hours at room temperature under an inert gas; adding ether to said reaction mixture to form a precipitate and filtering said precipitate; dissolving said precipitate in dry dimethoxyethane at room temperature under an inert gas; adding a solution of N-hydroxymethylmaleimide at room temperature under an inert gas; stirring said reaction mixture for about 12 hours under an inert gas; adding ether to said reaction mixture to cause a precipitate and filtering said precipitate; and evaporating said filtrate to yield the product.
Claim 2
Independent Claim
132 words
A method for the preparation of maleimidomethyl carbonate terminated polyalkylene oxides of the formula: ##STR3## where n is from 6 to 7, said method comprising: adding a solution of carbonyl chloride at -3° C. to a solution of a polyalkylene oxide at -3° C.; stirring said reaction mixture for about 12 hours at room temperature under an inert gas; adding ether to said reaction mixture to form a precipitate and filtering said precipitate; dissolving said precipitate in dry dimethoxyethane at room temperature under an inert gas; adding a solution of N-hydroxymethylmaleimide at room temperature under an inert gas; stirring said reaction mixture for about 12 hours under an inert gas; adding ether to said reaction mixture to cause a precipitate and filtering said precipitate; and evaporating said filtrate to yield the product.
Claim 3
Dependent Claim
24 words
A method according to claim 13 wherein said polyalkylene oide is a polypropylene glycol having ether linkages and a molecular weight of about 425.
Claim 4
Dependent Claim
15 words
As a composition of matter the bis(maleimidomethyl) carbonate of polypropylene glycol of molecular weight 425.
Claim 5
Dependent Claim
15 words
As a composition of matter the bis(maleimidomethyl) carbonate of polypropylene glycol of molecular weight 425.
Claim 6
Independent Claim
132 words
A method for the preparation of maleimidomethyl carbonate terminated polyalkylene oxides of the formula: ##STR4## where n is from 23 to 24, said method comprising: adding a solution of carbonyl chloride at -3° C. to a solution of a polyalkylene oxide at -3° C.; stirring said reaction mixture for about 12 hours at room temperature under an inert gas; adding ether to said reaction mixture to form a precipitate and filtering said preciptiate; dissolving said precipitate in dry dimethoxyethane at room temperature under an inert gas; adding a solution of N-hydroxymethylmaleimide at room temperature under an inert gas; stirring said reaction mixture for about 12 hours under an inert gas; adding ether to said reaction mixture to cause a precipitate and filtering said precipitate; and evaporating said filtrate to yield the product.
Claim 7
Independent Claim
132 words
A method for the preparation of maleimidomethyl carbonate terminated polyalkylene oxides of the formula: ##STR4## where n is from 23 to 24, said method comprising: adding a solution of carbonyl chloride at -3° C. to a solution of a polyalkylene oxide at -3° C.; stirring said reaction mixture for about 12 hours at room temperature under an inert gas; adding ether to said reaction mixture to form a precipitate and filtering said preciptiate; dissolving said precipitate in dry dimethoxyethane at room temperature under an inert gas; adding a solution of N-hydroxymethylmaleimide at room temperature under an inert gas; stirring said reaction mixture for about 12 hours under an inert gas; adding ether to said reaction mixture to cause a precipitate and filtering said precipitate; and evaporating said filtrate to yield the product.
Claim 8
Dependent Claim
13 words
A method according to claim 4 wherein said inert gas is nitrogen gas.
Claim 9
Dependent Claim
22 words
A method according to claim 4 wherein said polyalkylene oxide is the polyoxyalkyl derivative of trimethylolpropane with a molecular weight of 4542.
Claim 10
Dependent Claim
13 words
A method according to claim 1 wherein said inert gas is nitrogen gas.
Claim 11
Dependent Claim
19 words
As a composition of matter the tris(maleimidomethyl) carbonate of the polypropyleneoxy derivative of trimethylol propane of molecular weight 4542.
Claim 12
Dependent Claim
19 words
As a composition of matter the tris(maleimidomethyl) carbonate of the polypropyleneoxy derivative of trimethylol propane of molecular weight 4542.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1990-06-22 | 1990-12-22 | 1991-06-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-06-22 | 1994-12-22 | 1995-06-23 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-06-22 | 1998-12-22 | 1999-06-23 | $7700.00 | Window Closed / Lapsed |