US4115634A
Expired / Lapsed
US
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Amine salts of amino acids as delayed action catalysts
Assignee: Air Products and Chemicals Inc
•
Filing: 1976-12-01
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Granted: 1978-09-19
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Expires: 1996-12-01
Abstract
Abstract The amine salts of amino acid compositions have been found to be effective as a delayed action catalyst for organometallic catalyzed urethane synthesis. The acid which provides the basis for the salts is characterized generally by reacting an amine with an unsaturated acid, or with formaldehyde and hydrogen cyanide followed by hydrolysis of the resulting nitrile.
Inventors
- 👤 Ibrahim S. Bechara
- 👤 Rocco L. Mascioli
- 👤 Philip J. Zaluska
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 20:45
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/08; C08G18/16; C08G18/161; C08G18/163; C08G18/18; C08G18/1875
Claims Analysis
Total Claims: 31
Claim 1
Independent Claim
219 words
In a process for the production of a urethane composition by polymerizing an organic polyisocyanate, an organic compound having an active hydrogen atom, and an organometallic catalyst, the improvement which comprises using an effective proportion of a catalyst comprising an organometallic catalyst and an amine salt of an amino acid selected from the group represented by the formulas: ##STR2## wherein R 1 , R 2 and R 3 independently are alkylene groups having from 1 to 15 carbon atoms, cycloalkyl groups, phenyl groups and phenyl alkyl groups with the alkyl portion having from 1 to 6 carbon atoms; and R 4 is an alkylene radical having from 1 to 4 carbon atoms; X is an amine salt of a carboxylic acid group; Y is a hydrogen atom, a hydroxyl group, a carboxylic acid group, a nitrile group, or an amine salt of a carboxylic acid group; Z is a hydrogen atom, a hydroxyl group, a carboxylic acid group, a nitrile group, or an amine salt of a carboxylic acid group; and n is 0 or 1; with the proviso that when X, Y, or Z is an amine salt of a carboxylic acid group, the carboxyl moiety is the linkage bonding the X, Y, or Z radical to the residue of the amine salt of formula I or II.
Claim 2
Dependent Claim
219 words
In a process for the production of a urethane composition by polymerizing an organic polyisocyanate, an organic compound having an active hydrogen atom, and an organometallic catalyst, the improvement which comprises using an effective proportion of a catalyst comprising an organometallic catalyst and an amine salt of an amino acid selected from the group represented by the formulas: ##STR2## wherein R 1 , R 2 and R 3 independently are alkylene groups having from 1 to 15 carbon atoms, cycloalkyl groups, phenyl groups and phenyl alkyl groups with the alkyl portion having from 1 to 6 carbon atoms; and R 4 is an alkylene radical having from 1 to 4 carbon atoms; X is an amine salt of a carboxylic acid group; Y is a hydrogen atom, a hydroxyl group, a carboxylic acid group, a nitrile group, or an amine salt of a carboxylic acid group; Z is a hydrogen atom, a hydroxyl group, a carboxylic acid group, a nitrile group, or an amine salt of a carboxylic acid group; and n is 0 or 1; with the proviso that when X, Y, or Z is an amine salt of a carboxylic acid group, the carboxyl moiety is the linkage bonding the X, Y, or Z radical to the residue of the amine salt of formula I or II.
Claim 3
Dependent Claim
29 words
The process of claim 1 wherein from about 0.1 to 5.0 parts by weight of the amine salt of an amino acid is included per 100 parts organic compound.
Claim 4
Dependent Claim
12 words
The process of claim 1 wherein the organic compound is a polyol.
Claim 5
Dependent Claim
14 words
The process of claim 1 wherein the organometallic catalyst is a organo tin compound.
Claim 6
Dependent Claim
16 words
The process of claim 4 wherein the organo portion of the organo tin compound is aliphatic.
Claim 7
Dependent Claim
18 words
The process of claim 1 wherein the amine salt of the amino acid is represented by Formula I.
Claim 8
Dependent Claim
19 words
The process of claim 6 wherein R 1 , and R 3 are alkylene groups, and n is 1.
Claim 9
Dependent Claim
19 words
The process of claim 7 wherein R 1 and R 2 have from about 1 to 6 carbon atoms.
Claim 10
Dependent Claim
19 words
The process of claim 8 wherein R 3 is an alkylene group having from 1 to 3 carbon atoms.
Claim 11
Dependent Claim
16 words
The process of claim 9 wherein X is a tertiary amine salt of a carboxylic acid.
Claim 12
Dependent Claim
11 words
The process of claim 10 wherein Z is a hydroxyl group.
Claim 13
Dependent Claim
16 words
The process of claim 10 wherein Y is a tertiary amine salt of a carboxylic acid.
Claim 14
Dependent Claim
11 words
The process of claim 12 wherein Z is a hydroxyl group.
Claim 15
Dependent Claim
16 words
The process of claim 13 wherein X and Y are triethylene diamine salts of carboxylic acids.
Claim 16
Dependent Claim
149 words
In a process for the production of a urethane composition by polymerizing an organic polyisocyanate, an organic compound having an active hydrogen atom, an organometallic catalyst, the improvement which comprises using an effective proportion of a catalyst comprising an organometallic catalyst and an amine salt of an amino acid produced by the reaction of (a) an amine selected from the group consisting of ammonia, a primary, and a secondary amine, and (b) a reactant selected from the group consisting of (i) an olefinic reactant having sufficient reactivity for displacing an amine hydrogen atom and having at least monoacid functionality or functionality convertible to the acid form, and (ii) a halogenated organic acid having sufficient reactivity to react with an amine hydrogen or having functionality convertible to the acid form; and wherein any said functionality is subsequently converted to the acid form prior to the formation of the amine salt.
Claim 17
Dependent Claim
149 words
In a process for the production of a urethane composition by polymerizing an organic polyisocyanate, an organic compound having an active hydrogen atom, an organometallic catalyst, the improvement which comprises using an effective proportion of a catalyst comprising an organometallic catalyst and an amine salt of an amino acid produced by the reaction of (a) an amine selected from the group consisting of ammonia, a primary, and a secondary amine, and (b) a reactant selected from the group consisting of (i) an olefinic reactant having sufficient reactivity for displacing an amine hydrogen atom and having at least monoacid functionality or functionality convertible to the acid form, and (ii) a halogenated organic acid having sufficient reactivity to react with an amine hydrogen or having functionality convertible to the acid form; and wherein any said functionality is subsequently converted to the acid form prior to the formation of the amine salt.
Claim 18
Dependent Claim
22 words
The process of claim 15 which includes from about 0.1 to 5 parts of the amine salt per 100 parts organic compound.
Claim 19
Dependent Claim
12 words
The process of claim 15 wherein the organic compound is a polyol.
Claim 20
Dependent Claim
14 words
The process of claim 15 wherein the organometallic catalyst is an organo tin compound.
Claim 21
Dependent Claim
34 words
The process of claim 15 wherein the reactant (b) is an olefinic compound and is selected from the group consisting of an unsaturated acid, an unsaturated nitrile, an unsaturated ketone and an unsaturated ester.
Claim 22
Dependent Claim
22 words
The process of claim 15 wherein amine (a) is selected from the group consisting of hydroxy-alkyl, and alkyl primary and secondary amines.
Claim 23
Dependent Claim
20 words
The process of claim 20 wherein the alkyl portion of the amine (a) has from 2 to 4 carbon atoms.
Claim 24
Dependent Claim
24 words
The process of claim 109 wherein the amine (a) is a primary amine, and 19 mols olefinic reactant are reacted per mol of amine.
Claim 25
Dependent Claim
27 words
The process of claim 22 wherein the olefinic reactant (b) is selected from the group consisting of acrylonitrile, acrylic acid, methyl vinyl ketone and substituted derivatives thereof.
Claim 26
Dependent Claim
17 words
The process of claim 15 wherein the catalyst component is a tertiary amine salt of amino acid.
Claim 27
Dependent Claim
111 words
In a process for the production of a urethane composition by polymerizing an organic polyisocyanate using an effective amount of a catalyst comprising an organometallic catalyst and an organic compound having an active hydrogen atom, and an organometallic catalyst, the improvement as a catalyst component which comprises the amine salt of an amino acid produced by reacting an amine (a) selected from the group consisting of ammonia, a primary and a secondary amine, with an aldehyde (b) and with a cyanide (c) to form a nitrile wherein at least one of the nitrile groups in the reaction product is subsequently converted to an acid prior to formation to the amine salt.
Claim 28
Dependent Claim
111 words
In a process for the production of a urethane composition by polymerizing an organic polyisocyanate using an effective amount of a catalyst comprising an organometallic catalyst and an organic compound having an active hydrogen atom, and an organometallic catalyst, the improvement as a catalyst component which comprises the amine salt of an amino acid produced by reacting an amine (a) selected from the group consisting of ammonia, a primary and a secondary amine, with an aldehyde (b) and with a cyanide (c) to form a nitrile wherein at least one of the nitrile groups in the reaction product is subsequently converted to an acid prior to formation to the amine salt.
Claim 29
Dependent Claim
13 words
The process of claim 25 wherein the amine (a) is a primary amine.
Claim 30
Dependent Claim
32 words
The process of claim 26 wherein the primary amine (a) is selected from the group consisting of hydroxyalkyl and alkyl amines with the alkyl portion having from 2 to 4 carbon atoms.
Claim 31
Dependent Claim
20 words
The process of claim 27 wherein the aldehyde (b) is formaldehyde and the amine salt is a tertiary amine salt.
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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) | 1981-09-18 | 1982-03-20 | 1982-09-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-09-18 | 1986-03-20 | 1986-09-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-09-18 | 1990-03-20 | 1990-09-19 | $7700.00 | Window Closed / Lapsed |