US4285876A
Expired / Lapsed
US
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Isocyanate adducts with β-diketones
Assignee: Vertac Inc
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Filing: 1979-10-10
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Granted: 1981-08-25
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Expires: 1999-10-10
Abstract
Abstract Adducts of low boiling isocyanates with β-diketones which decompose on heating to give the low boiling isocyanates as a condensible vapor; as well as the method of making the adducts and the method of storing and transporting low boiling isocyanates employing said adducts.
Inventors
- 👤 Luigi Giuffre
- 👤 Placido M. Spaziante
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 11:26
CPC Classifications
C; C07; C07C; C07C263/00; C07C263/18
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
172 words
A process for the production of the adduct of an isocyanate having the formula R--N═C═O wherein R is a member selected from the group consisting of alkyl having from 1 to 10 carbon atoms and alkenyl having 2 to 6 carbon atoms with a β-diketone selected from the group consisting of compounds having the formula ##STR15## wherein R' is lower alkyl and R" is a member selected from the group consisting of lower alkyl, alkoxy, phenyl and when taken together, lower alkylene having 2 to 6 carbon atoms, and decalin-1,8-dione, consisting essentially of the steps of reacting said isocyanate with a β-diketone selected from the group consisting of compounds having the formula ##STR16## wherein R' is lower alkyl and R" is a member selected from the group consisting of lower alkyl, alkoxy, phenyl and when taken together, lower alkylene having 2 to 6 carbon atoms, and decalin-1,8-dione, in a molar ratio of 1:1 to a molar excess of β-diketone at a temperature between 25° C. and 100° C., to form said adduct.
Claim 2
Dependent Claim
172 words
A process for the production of the adduct of an isocyanate having the formula R--N═C═O wherein R is a member selected from the group consisting of alkyl having from 1 to 10 carbon atoms and alkenyl having 2 to 6 carbon atoms with a β-diketone selected from the group consisting of compounds having the formula ##STR15## wherein R' is lower alkyl and R" is a member selected from the group consisting of lower alkyl, alkoxy, phenyl and when taken together, lower alkylene having 2 to 6 carbon atoms, and decalin-1,8-dione, consisting essentially of the steps of reacting said isocyanate with a β-diketone selected from the group consisting of compounds having the formula ##STR16## wherein R' is lower alkyl and R" is a member selected from the group consisting of lower alkyl, alkoxy, phenyl and when taken together, lower alkylene having 2 to 6 carbon atoms, and decalin-1,8-dione, in a molar ratio of 1:1 to a molar excess of β-diketone at a temperature between 25° C. and 100° C., to form said adduct.
Claim 3
Dependent Claim
32 words
The process of claim 1 wherein said reaction is conducted in the presence of catalytic amounts of a catalyst selected from the group consisting of a tertiary amine and an inorganic acid.
Claim 4
Dependent Claim
9 words
The process of claim 1 wherein R is methyl.
Claim 5
Dependent Claim
16 words
The process of claim 1 wherein said isocyanate is methyl isocyanate and said β-diketone is acetylacetone.
Claim 6
Dependent Claim
24 words
The process of claim 1 wherein said reaction is conducted in the presence of an organic solvent having basic properties according to Lewis theory.
Claim 7
Dependent Claim
141 words
A process for storing and transporting an isocyanate having the formula R--N═C═O wherein R is a member selected from the group consisting of alkyl having from 1 to 10 carbon atoms and alkenyl having from 2 to 6 carbon atoms, consisting of the steps of (1) reacting said isocyanate with a β-diketone selected from the group consisting of compounds having the formula ##STR17## wherein R' is lower alkyl and R" is a member selected from the group consisting of lower alkyl, alkoxy, phenyl and when taken together, lower alkylene having 2 to 6 carbon atoms, and decalin-1,8-dione, or reacting a carbamoyl chloride having the formula ##STR18## with said β-diketone, to form an adduct, (2) maintaining said adduct at temperatures below the decomposition temperature for the time desired, and (3) heating said adduct to decompose the same with evolution of the isocyanate.
Claim 8
Dependent Claim
141 words
A process for storing and transporting an isocyanate having the formula R--N═C═O wherein R is a member selected from the group consisting of alkyl having from 1 to 10 carbon atoms and alkenyl having from 2 to 6 carbon atoms, consisting of the steps of (1) reacting said isocyanate with a β-diketone selected from the group consisting of compounds having the formula ##STR17## wherein R' is lower alkyl and R" is a member selected from the group consisting of lower alkyl, alkoxy, phenyl and when taken together, lower alkylene having 2 to 6 carbon atoms, and decalin-1,8-dione, or reacting a carbamoyl chloride having the formula ##STR18## with said β-diketone, to form an adduct, (2) maintaining said adduct at temperatures below the decomposition temperature for the time desired, and (3) heating said adduct to decompose the same with evolution of the isocyanate.
Claim 9
Dependent Claim
34 words
The process of claim 6 wherein said isocyanate is reacted with said β-diketone in a molar ratio of 1:1 to a molar excess of β-diketone at a temperature between 25° C. and 100° C.
Claim 10
Dependent Claim
29 words
The process of claim 7 wherein said reaction is conducted in the presence of a catalyst selected from the group consisting of a tertiary amine and an inorganic acid.
Claim 11
Dependent Claim
9 words
The process of claim 7 wherein R is methyl.
Claim 12
Dependent Claim
16 words
The process of claim 7 wherein said isocyanate is methyl isocyanate and said β-diketone is acetylacetone.
Claim 13
Dependent Claim
24 words
The process of claim 7 wherein said reaction is conducted in the presence of an organic solvent having basic properties according to Lewis theory.
Claim 14
Dependent Claim
25 words
The process of claim 6 wherein said heating step to decompose said adduct is conducted at a temperature of from 100° C. to 500° C.
Claim 15
Dependent Claim
21 words
The process of claim 12 wherein said heating step is conducted at a temperature of from 120° C. to 160° C.
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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) | 1984-08-24 | 1985-02-23 | 1985-08-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-08-24 | 1989-02-23 | 1989-08-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-08-24 | 1993-02-23 | 1993-08-25 | $7700.00 | Window Closed / Lapsed |