US4542214A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Carbamate and carbonate salts of tertiary amines
Assignee: Air Products and Chemicals Inc
•
Filing: 1984-01-05
•
Granted: 1985-09-17
•
Expires: 2004-01-05
Abstract
Abstract Novel carbamic and carbonic acid derivatives are provided by simultaneous reaction of a secondary amine and a tertiary amine with carbon dioxide. These derivatives correspond in general to the formula ##STR1## in which R 1 and R 2 may be individual substituents attached to the N or together form with N a heterocyclic moiety; R 3 , R 4 , R 5 may be individual short chain alkyl or hydroxyalkyl substituents on the N or form therewith a monocyclic or bicyclic heterocyclic moiety. These described compounds find particular use as heat activatable delayed action catalysts especially for use in polyurethane formulations.
Inventors
- 👤 Ibrahim S. Bechara
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 23:51
CPC Classifications
C; C07; C07D; C07D295/00; C07D295/02; C07D295/027; C07D295/16; C07D295/20; C07D295/205; C07D487/00; C07D487/02; C07D487/08; C08; C08G; C08G18/00; C08G18/06; C08G18/08; C08G18/16; C08G18/18; C08G18/1875; C08G18/20
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
30 words
The method for producing carbamate and carbonate salts of tertiary amines which comprises admixing a secondary amine with a tertiary amine in the presence of carbon dioxide under reaction conditions.
Claim 2
Independent Claim
30 words
The method for producing carbamate and carbonate salts of tertiary amines which comprises admixing a secondary amine with a tertiary amine in the presence of carbon dioxide under reaction conditions.
Claim 3
Dependent Claim
67 words
The method as defined in claim 1 wherein said secondary amine is one corresponding to the formula ##STR27## wherein R 1 and R 2 are independently alkyl groups of 1 to 20 carbon atoms, in which the alkyl groups may contain one or more hydroxyl groups, or R 1 and R 2 can be a carbon atom-containing chain joined to the N to form a heterocyclic ring.
Claim 4
Dependent Claim
36 words
The method as defined in claim 2 wherein R 1 and R 2 together constitute a carbon-containing chain joined to nitrogen and forming therewith a hetero ring from the group consisting of imidazole, morpholine and piperazine.
Claim 5
Dependent Claim
71 words
The method as defined in claim 1 wherein said tertiary amine is one corresponding to the formula ##STR28## where R 3 , R 4 and R 5 are independently alkyl of 1 to 3 carbon atoms, hydroxy alkyl of up to 3 carbon atoms, or R 3 , R 4 and R 5 are organic radicals joined to the N to form a monocyclic or bicyclic hetero ring comprising tertiary nitrogen.
Claim 6
Dependent Claim
32 words
The method as defined in claim 4 wherein R 3 , R 4 and R 5 form a hetero ring from the group consisting of triethylenediamine, quinuclidine, N-alkyl piperazine and N-alkyl morpholine.
Claim 7
Dependent Claim
23 words
The method as defined in claim 1, wherein said secondary and tertiary amines are reacted in equimolar amounts with excess of carbon dioxide.
Claim 8
Dependent Claim
162 words
Compounds of the formula ##STR29## wherein R 1 and R 2 are independently alkyl groups of 1 to 20 carbons, which alkyl groups may contain one or more hydroxyl groups, or R 1 and R 2 are carbon containing radicals joined to form with N a hetero ring of 5 to 6 members; R 3 , R 4 and R 5 are independently alkyl groups of 1 to 3 carbons, hydroxyalkyl groups of 1 to 3 carbons, or they can be organic radicals joined in a monocyclic or bicyclic hetero ring providing a cyclic tertiary amine moiety; or one of the groups R 1 , R 2 , R 3 , R 4 or R 5 is an ethylene radical attached to another dialkyl amino alkyl group by an oxygen atom forming a ditertiary amine of the formula: ##STR30## where each R 6 independently is an alkyl group of 1 to 3 carbon atoms; n and m are independently 2 or 3.
Claim 9
Dependent Claim
162 words
Compounds of the formula ##STR29## wherein R 1 and R 2 are independently alkyl groups of 1 to 20 carbons, which alkyl groups may contain one or more hydroxyl groups, or R 1 and R 2 are carbon containing radicals joined to form with N a hetero ring of 5 to 6 members; R 3 , R 4 and R 5 are independently alkyl groups of 1 to 3 carbons, hydroxyalkyl groups of 1 to 3 carbons, or they can be organic radicals joined in a monocyclic or bicyclic hetero ring providing a cyclic tertiary amine moiety; or one of the groups R 1 , R 2 , R 3 , R 4 or R 5 is an ethylene radical attached to another dialkyl amino alkyl group by an oxygen atom forming a ditertiary amine of the formula: ##STR30## where each R 6 independently is an alkyl group of 1 to 3 carbon atoms; n and m are independently 2 or 3.
Claim 10
Dependent Claim
46 words
Compounds of the formula (I) of claim 7 wherein ##STR31## represents a heterocyclic secondary amine moiety from the group consisting of imidazole, morpholine, and piperazine and ##STR32## represents a heterocyclic tertiary amine moiety from the group consisting of triethylene diamine, quinuclidine, N-alkyl piperazine and N-alkyl morpholine.
Claim 11
Dependent Claim
31 words
Compounds of the formula (I) of claim 7 wherein at least one R 3 , R 4 and R 5 constitute the moiety of a ditertiary amine of the formula (II).
Claim 12
Dependent Claim
20 words
Compounds of the formula (I) of claim 7 wherein R 3 , R 4 and R 5 together are bis(N,N-dimethyl-amino)ethyl)ether.
Claim 13
Dependent Claim
15 words
The compound of claim 7 which is the triethylene diamine salt of bis-hydroxyethyl carbamic acid.
Claim 14
Dependent Claim
13 words
The compound of claim 7 which is the dimethylethanolamine salt of morpholino-carbamic acid.
Claim 15
Dependent Claim
14 words
The compound of claim 7 which is the 2-methyltriethylene diamine salt of diethanolamino-carbamic acid.
Claim 16
Dependent Claim
16 words
The compound of claim 7 which is the bis(dimethylaminoethyl)ether salt of carbamic and N-substituted carbamic acids.
Claim 17
Dependent Claim
45 words
Formulations for the production of polyurethanes comprising as catalyst or co-catalyst therein a compound of the formula selected from the group consisting of ##STR33## wherein R 1 , R 2 , R 3 , R 4 and R 5 are as defined in claim 7.
Claim 18
Dependent Claim
19 words
Formulations for the production of polyurethanes comprising as catalyst or co-catalyst therein a compound as defined in claim 8.
Claim 19
Dependent Claim
17 words
Formulations for the production of polyurethane comprising as catalyst or co-catalyst therein the compound of claim 11.
Claim 20
Dependent Claim
55 words
In methods for the production of polyurethane by reaction of an organic isocyanate compound with a polyol, the improvement which comprises promoting said reaction with a catalyst composition comprising a tertiary amine salt of a carbamic acid compound, the nitrogen component of the carbamic acid comprising a substituent or substituents forming a secondary amine moiety.
Claim 21
Dependent Claim
55 words
In methods for the production of polyurethane by reaction of an organic isocyanate compound with a polyol, the improvement which comprises promoting said reaction with a catalyst composition comprising a tertiary amine salt of a carbamic acid compound, the nitrogen component of the carbamic acid comprising a substituent or substituents forming a secondary amine moiety.
Claim 22
Dependent Claim
19 words
The improvement as defined in claim 18 wherein said catalyst composition comprises a compound as defined in claim 8.
Claim 23
Dependent Claim
18 words
The improvement as defined in claim 18 wherein said catalyst composition comprises the compound recited in claim 11.
References Cited (Backward Citations)
US3839252A
Cited
US3655719A
Cited
US3728291A
Cited
US3767602A
Cited
US3817939A
Cited
US3954729A
Cited
US3962100A
Cited
US4102863A
Cited
US4141810A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-09-16 | 1989-03-18 | 1989-09-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-09-16 | 1993-03-18 | 1993-09-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-09-16 | 1997-03-18 | 1997-09-17 | $7700.00 | Window Closed / Lapsed |