US4040992A
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US
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Catalysis of organic isocyanate reactions
Assignee: Air Products and Chemicals Inc
•
Filing: 1975-07-29
•
Granted: 1977-08-09
•
Expires: 1995-07-29
Abstract
Abstract Polymerization and condensation reactions of organic isocyanates are catalytically promoted by the use of N-hydroxyalkyl quaternary ammonium carbonylate salts, particularly in the production of polyisocyanurates and polyurethanes. Among the exemplary preferred catalysts are N-hydroxypropyl trimethyl ammonium salts of carboxylic acids such as those of formic and acetic acids and of fatty acids such as hexanoic and octanoic acids and the like.
Inventors
- 👤 Ibrahim S. Bechara
- 👤 Felix P. Carroll
- 👤 Dewey G. Holland
- 👤 Rocco L. Mascioli
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 06:51
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/02; C08G18/022; C08G18/06; C08G18/08; C08G18/16; C08G18/18; C08G18/1875; C08G2115/00; C08G2115/02; Y; Y10; Y10S; Y10S521/00; Y10S521/902
Claims Analysis
Total Claims: 31
Claim 1
Independent Claim
324 words
In the process of promoting organic isocyanate condensation and/or polymerization reactions in the production of products containing respectively urethane and isocyanurate groups, the improvement which consists in utilizing for such promotion a catalytic quantity of a hydroxyalkyl quaternary ammonium compound corresponding to the general formula ##STR36## wherein a = zero or one R 1 , R 2 and R 3 are independently alkyl or hydroxyalkyl of 1 to 20 carbon atoms, or cycloalkyl groups of 3 to 8 carbon atoms, aralkyl, aryl, alkenyl of 2 to 20 carbon atoms, or alkynyl of 2 to 6 carbon atoms, or R 1 , r 2 and R 3 together constitute a heterocyclic structure from the group consisting of quinuclidine, N-methyl morpholine, N-ethyl morpholine and N,N'-dimethyl piperazine; R 4 is H, phenyl, an alkyl group of 1 to 15 carbon atoms, an alkenyl group of 2 to 15 carbon atoms, an alkynyl group of 2 to 6 carbon atoms, a hydroxy alkyl group of 1 to 9 carbon atoms, a keto alkyl group having a total of 3 to 15 carbon atoms; or an alkoxy alkyl group having a total of 2 to 20 carbon atoms; Y is H, an alkyl group of 1 to 20 carbon atoms, an alkenyl group of 2 to 15 carbon atoms, a cycloalkyl group of 3 to 6 carbon atoms, phenyl, an alkyl phenyl having 1 to 9 carbon atoms in the alkyl group or groups attached to the phenyl ring, benzyl, an alkyl benzyl having 1 to 9 carbon atoms in the alkyl group or groups attached to the ring, or a CH.sub.(3-b) Z.sub.(b) group, wherein b = 1 to 3 and Z is OH, CN, Cl, an alkoxy group of 1 to 5 carbon atoms, a phenyl group or methoxy phenyl group, or Z is (CH.sub.2).sub.d COOR, wherein d is equal to zero to four and R is hydrogen or an alkyl group of up to 20 carbon atoms.
Claim 2
Dependent Claim
324 words
In the process of promoting organic isocyanate condensation and/or polymerization reactions in the production of products containing respectively urethane and isocyanurate groups, the improvement which consists in utilizing for such promotion a catalytic quantity of a hydroxyalkyl quaternary ammonium compound corresponding to the general formula ##STR36## wherein a = zero or one R 1 , R 2 and R 3 are independently alkyl or hydroxyalkyl of 1 to 20 carbon atoms, or cycloalkyl groups of 3 to 8 carbon atoms, aralkyl, aryl, alkenyl of 2 to 20 carbon atoms, or alkynyl of 2 to 6 carbon atoms, or R 1 , r 2 and R 3 together constitute a heterocyclic structure from the group consisting of quinuclidine, N-methyl morpholine, N-ethyl morpholine and N,N'-dimethyl piperazine; R 4 is H, phenyl, an alkyl group of 1 to 15 carbon atoms, an alkenyl group of 2 to 15 carbon atoms, an alkynyl group of 2 to 6 carbon atoms, a hydroxy alkyl group of 1 to 9 carbon atoms, a keto alkyl group having a total of 3 to 15 carbon atoms; or an alkoxy alkyl group having a total of 2 to 20 carbon atoms; Y is H, an alkyl group of 1 to 20 carbon atoms, an alkenyl group of 2 to 15 carbon atoms, a cycloalkyl group of 3 to 6 carbon atoms, phenyl, an alkyl phenyl having 1 to 9 carbon atoms in the alkyl group or groups attached to the phenyl ring, benzyl, an alkyl benzyl having 1 to 9 carbon atoms in the alkyl group or groups attached to the ring, or a CH.sub.(3-b) Z.sub.(b) group, wherein b = 1 to 3 and Z is OH, CN, Cl, an alkoxy group of 1 to 5 carbon atoms, a phenyl group or methoxy phenyl group, or Z is (CH.sub.2).sub.d COOR, wherein d is equal to zero to four and R is hydrogen or an alkyl group of up to 20 carbon atoms.
Claim 3
Dependent Claim
33 words
The method as defined in claim 1 wherein each of R 1 , R 2 , R 3 and R 4 is a short chain alkyl group of up to three carbon atoms.
Claim 4
Dependent Claim
36 words
The method as defined in claim 1 wherein said quaternary ammonium compound of the formula is a 2-hydroxy propyl trimethyl ammonium salt of an aliphatic carboxylic acid having a total of up to ten carbon atoms.
Claim 5
Dependent Claim
13 words
The method as defined in claim 3 wherein said acid is formic acid.
Claim 6
Dependent Claim
14 words
The method as defined in claim 3 wherein said acid is an isodecanoic acid.
Claim 7
Dependent Claim
14 words
The method as defined in claim 3 wherein said acid is 2-ethyl hexanoic acid.
Claim 8
Dependent Claim
11 words
The method as defined in claim 1 wherein a = zero.
Claim 9
Dependent Claim
316 words
In the production of foamed plastics by reaction of an organic polyisocyanate compound with a high molecular weight polyol, the improvement which consists in utilizing as catalyst in said reaction a compound corresponding to the formula ##STR37## wherein a = zero or one, R 1 , r 2 and R 3 are independently alkyl or hydroxy alkyl of 1 to 20 carbon atoms, or cycloalkyl groups of 3 to 8 carbon atoms, aralkyl, aryl, alkenyl of 2 to 20 carbon atoms, or alkynol of 2 to 6 carbon atoms, or R 1 , r 2 and R 3 together constitute a heterocyclic structure from the group consisting of quinuclidine, N-methyl morpholine, N-ethyl morpholine and N,N'-dimethyl piperazine; R 4 is H, phenyl, an alkyl group of 1 to 15 carbon atoms, an alkenyl group of 2 to 15 carbon atoms, an alkynyl group of 2 to 6 carbon atoms, a hydroxy alkyl group of 1 to 9 carbon atoms, a keto alkyl group having a total of 3 to 15 carbon atoms, or an alkoxy alkyl group having a total of 2 to 20 carbon atoms; Y is H, an alkyl group of 1 to 20 carbon atoms, an alkenyl group of 2 to 15 carbon atoms, a cycloalkyl group of 3 to 6 carbon atoms, phenyl, an alkyl phenyl having 1 to 9 carbon atoms in the alkyl group or groups attached to the phenyl ring, benzyl, an alkyl benzyl having 1 to 9 carbon atoms in the alkyl group or groups attached to the ring, or a CH.sub.(3.sub.-b) Z.sub.(b) group, wherein b = 1 to 3 and Z is OH, CN, Cl, an alkoxy group of 1 to 5 carbon atoms, a phenyl group or methoxy phenyl group, or Z is (CH.sub.2).sub.d COOR, wherein d is equal to zero to four and R is hydrogen or an alkyl group of up to 20 carbon atoms.
Claim 10
Dependent Claim
316 words
In the production of foamed plastics by reaction of an organic polyisocyanate compound with a high molecular weight polyol, the improvement which consists in utilizing as catalyst in said reaction a compound corresponding to the formula ##STR37## wherein a = zero or one, R 1 , r 2 and R 3 are independently alkyl or hydroxy alkyl of 1 to 20 carbon atoms, or cycloalkyl groups of 3 to 8 carbon atoms, aralkyl, aryl, alkenyl of 2 to 20 carbon atoms, or alkynol of 2 to 6 carbon atoms, or R 1 , r 2 and R 3 together constitute a heterocyclic structure from the group consisting of quinuclidine, N-methyl morpholine, N-ethyl morpholine and N,N'-dimethyl piperazine; R 4 is H, phenyl, an alkyl group of 1 to 15 carbon atoms, an alkenyl group of 2 to 15 carbon atoms, an alkynyl group of 2 to 6 carbon atoms, a hydroxy alkyl group of 1 to 9 carbon atoms, a keto alkyl group having a total of 3 to 15 carbon atoms, or an alkoxy alkyl group having a total of 2 to 20 carbon atoms; Y is H, an alkyl group of 1 to 20 carbon atoms, an alkenyl group of 2 to 15 carbon atoms, a cycloalkyl group of 3 to 6 carbon atoms, phenyl, an alkyl phenyl having 1 to 9 carbon atoms in the alkyl group or groups attached to the phenyl ring, benzyl, an alkyl benzyl having 1 to 9 carbon atoms in the alkyl group or groups attached to the ring, or a CH.sub.(3.sub.-b) Z.sub.(b) group, wherein b = 1 to 3 and Z is OH, CN, Cl, an alkoxy group of 1 to 5 carbon atoms, a phenyl group or methoxy phenyl group, or Z is (CH.sub.2).sub.d COOR, wherein d is equal to zero to four and R is hydrogen or an alkyl group of up to 20 carbon atoms.
Claim 11
Dependent Claim
14 words
The process as defined in claim 8 wherein said foamed plastic is a polyurethane.
Claim 12
Dependent Claim
14 words
The process as defined in claim 8 wherein said foamed plastic comprises isocyanurate groups.
Claim 13
Dependent Claim
311 words
A process for the production of polyurethane plastics comprising the reaction of an aryl polyisocyanate, a high molecular weight polyol and a catalytic quantity of a hydroxyalkyl quaternary ammonium compound corresponding to the formula ##STR38## wherein a = zero or one, R 1 , r 2 and R 3 are independently alkyl or hydroxyalkyl of 1 to 20 carbon atoms, or cycloalkyl groups of 3 to 8 carbon atoms, aralkyl, aryl, alkenyl of 2 to 20 carbon atoms, or alkynyl of 2 to 6 carbon atoms, or R 1 , r 2 and R 3 together constitute a heterocyclic structure from the group consisting of quinuclidine, N-methyl morpholine, N-ethyl morpholine and N,N'-dimethyl piperazine; R 4 is H, phenyl, analkyl group of 1 to 15 carbon atoms, an alkenyl group of 2 to 15 carbon atoms, an alkynyl group of 2 to 6 carbon atoms, a hydroxyalkyl group of 1 to 9 carbon atoms, a keto alkyl group having a total of 3 to 15 carbon atoms, or an alkoxy alkyl group having a total of 2 to 20 carbon atoms; Y is H, an alkyl group of 1 to 20 carbon atoms, an alkenyl group of 2 to 15 carbon atoms, a cycloalkyl group of 3 to 6 carbon atoms, phenyl, an alkyl phenyl having 1 to 9 carbon atoms in the alkyl group or groups attached to the phenyl ring, benzyl, an alkyl benzyl having 1 to 9 carbon atoms in the alkyl group or groups attached to the ring, or a CH.sub.(3.sub.-b) Z.sub.(b) group, wherein b = 1 to 3 and Z is OH, CN, Cl, an alkoxy group of 1 to 5 carbon atoms, a phenyl group or methoxy phenyl group, or Z is (CH.sub.2).sub.d COOR, wherein d is equal to zero to four and R is hydrogen or an alkyl group of up to 20 carbon atoms.
Claim 14
Dependent Claim
311 words
A process for the production of polyurethane plastics comprising the reaction of an aryl polyisocyanate, a high molecular weight polyol and a catalytic quantity of a hydroxyalkyl quaternary ammonium compound corresponding to the formula ##STR38## wherein a = zero or one, R 1 , r 2 and R 3 are independently alkyl or hydroxyalkyl of 1 to 20 carbon atoms, or cycloalkyl groups of 3 to 8 carbon atoms, aralkyl, aryl, alkenyl of 2 to 20 carbon atoms, or alkynyl of 2 to 6 carbon atoms, or R 1 , r 2 and R 3 together constitute a heterocyclic structure from the group consisting of quinuclidine, N-methyl morpholine, N-ethyl morpholine and N,N'-dimethyl piperazine; R 4 is H, phenyl, analkyl group of 1 to 15 carbon atoms, an alkenyl group of 2 to 15 carbon atoms, an alkynyl group of 2 to 6 carbon atoms, a hydroxyalkyl group of 1 to 9 carbon atoms, a keto alkyl group having a total of 3 to 15 carbon atoms, or an alkoxy alkyl group having a total of 2 to 20 carbon atoms; Y is H, an alkyl group of 1 to 20 carbon atoms, an alkenyl group of 2 to 15 carbon atoms, a cycloalkyl group of 3 to 6 carbon atoms, phenyl, an alkyl phenyl having 1 to 9 carbon atoms in the alkyl group or groups attached to the phenyl ring, benzyl, an alkyl benzyl having 1 to 9 carbon atoms in the alkyl group or groups attached to the ring, or a CH.sub.(3.sub.-b) Z.sub.(b) group, wherein b = 1 to 3 and Z is OH, CN, Cl, an alkoxy group of 1 to 5 carbon atoms, a phenyl group or methoxy phenyl group, or Z is (CH.sub.2).sub.d COOR, wherein d is equal to zero to four and R is hydrogen or an alkyl group of up to 20 carbon atoms.
Claim 15
Dependent Claim
26 words
The process as defined in claim 11 wherein said quaternary ammonium compound of the formula is a 2-hydroxypropyl trimethyl ammonium salt of an aliphatic carboxylic acid.
Claim 16
Dependent Claim
13 words
The process as defined in claim 12 wherein said acid is formic acid.
Claim 17
Dependent Claim
14 words
The process as defined in claim 12 wherein said acid is an octanoic acid.
Claim 18
Dependent Claim
20 words
The process as defined in claim 11 wherein said quaternary compound of the formula is a salt of glycolic acid.
Claim 19
Dependent Claim
316 words
A process for production of blown polyisocyanurate resins comprising the reaction of an organic polyisocyanate, a high molecular weight polyol, a blowing agent, and a catalytic quantity of a hydroxyalkyl quaternary ammonium compound corresponding to the general formula ##STR39## wherein a = zero or one, R 1 , r 2 and R 3 are independently alkyl or hydroxyalkyl of 1 to 20 carbon atoms, or cycloalkyl groups of 3 to 8 carbon atoms, aralkyl, aryl, alkenyl of 2 to 29 carbon atoms, or alkynyl of 2 to 6 carbon atoms, or R 1 , r 2 and R 3 together constitute a heterocyclic structure from the group consisting of quinuclidine, N-methyl morpholine, N-ethyl morpholine and N,N'-dimethyl piperazine; R 4 is H, phenyl, an alkyl group of 1 to 15 carbon atoms, an alkenyl group of 2 to 15 carbon atoms, an alkynyl group of 2 to 6 carbon atoms, a hydroxyalkyl group of 1 to 9 carbon atoms, a keto alkyl group having a total of 3 to 15 carbon atoms, or an alkoxy alkyl group having a total of 2 to 20 carbon atoms; Y is H, an alkyl group of 1 to 20 carbon atoms, an alkenyl group of 2 to 15 carbon atoms, a cycloalkyl group of 3 to 6 carbon atoms, phenyl, an alkyl phenyl having 1 to 9 carbon atoms in the alkyl group or groups attached to the phenyl ring, benzyl, an alkyl benzyl having 1 to 9 carbon atoms in the alkyl group or groups attached to the ring, or a CH.sub.(3.sub.-b) Z.sub.(b) groups, wherein b = 1 to 3 and Z is OH, CN, Cl, an alkoxy group of 1 to 5 carbon atoms, a phenyl group or methoxy phenyl group, or Z is (CH.sub.2).sub.d COOR, wherein d is equal to zero to four and R is hydrogen or an alkyl group of up to 20 carbon atoms.
Claim 20
Dependent Claim
316 words
A process for production of blown polyisocyanurate resins comprising the reaction of an organic polyisocyanate, a high molecular weight polyol, a blowing agent, and a catalytic quantity of a hydroxyalkyl quaternary ammonium compound corresponding to the general formula ##STR39## wherein a = zero or one, R 1 , r 2 and R 3 are independently alkyl or hydroxyalkyl of 1 to 20 carbon atoms, or cycloalkyl groups of 3 to 8 carbon atoms, aralkyl, aryl, alkenyl of 2 to 29 carbon atoms, or alkynyl of 2 to 6 carbon atoms, or R 1 , r 2 and R 3 together constitute a heterocyclic structure from the group consisting of quinuclidine, N-methyl morpholine, N-ethyl morpholine and N,N'-dimethyl piperazine; R 4 is H, phenyl, an alkyl group of 1 to 15 carbon atoms, an alkenyl group of 2 to 15 carbon atoms, an alkynyl group of 2 to 6 carbon atoms, a hydroxyalkyl group of 1 to 9 carbon atoms, a keto alkyl group having a total of 3 to 15 carbon atoms, or an alkoxy alkyl group having a total of 2 to 20 carbon atoms; Y is H, an alkyl group of 1 to 20 carbon atoms, an alkenyl group of 2 to 15 carbon atoms, a cycloalkyl group of 3 to 6 carbon atoms, phenyl, an alkyl phenyl having 1 to 9 carbon atoms in the alkyl group or groups attached to the phenyl ring, benzyl, an alkyl benzyl having 1 to 9 carbon atoms in the alkyl group or groups attached to the ring, or a CH.sub.(3.sub.-b) Z.sub.(b) groups, wherein b = 1 to 3 and Z is OH, CN, Cl, an alkoxy group of 1 to 5 carbon atoms, a phenyl group or methoxy phenyl group, or Z is (CH.sub.2).sub.d COOR, wherein d is equal to zero to four and R is hydrogen or an alkyl group of up to 20 carbon atoms.
Claim 21
Dependent Claim
31 words
The process as defined in claim 16 wherein at least two of R 1 , R 2 and R 3 are short chain alkyl groups of up to three carbon atoms.
Claim 22
Dependent Claim
22 words
The process as defined in claim 16 wherein R 4 is a short chain alkyl group of up to three carbon atoms.
Claim 23
Dependent Claim
12 words
The process as defined in claim 16 wherein R 4 is methyl.
Claim 24
Dependent Claim
27 words
The process as defined in claim 16 wherein said quaternary ammonium compound of the formula is an aliphatic acid salt of a hydroxy alkyl trimethyl ammonium compound.
Claim 25
Dependent Claim
13 words
The process as defined in claim 20 wherein said acid is formic acid.
Claim 26
Dependent Claim
20 words
The process as defined in claim 20 wherein said acid is a fatty acid having 8 to 10 carbon atoms.
Claim 27
Dependent Claim
14 words
The process as defined in claim 20 wherein said acid is 2-ethyl hexanoic acid.
Claim 28
Dependent Claim
111 words
In the method of trimerizing aliphatic and aralkyl polyisocyanates selected from the group consisting of isophorone polyisocyanate, hexamethylene polyisocyanate, methylene bis cyclohexyl polyisocyanate, xylylene polyisocyanate, and mixtures thereof the improvement which comprises promoting said trimerization by a catalytic quantity of a fully substituted quaternary ammonium carboxylate having 1 to 2 hydroxyl alkyl groups attached to the quaternary nitrogen having the formula: ##STR40## wherein R 1 , R 2 , R 3 and R 4 are short chain alkyl groups having up to 3 carbon atoms, and R 5 is H, an alkyl group of 1 to 18 carbon atoms, alkynyl group of 2 to 15 carbon atoms, benzyl or methoxy benzyl.
Claim 29
Dependent Claim
111 words
In the method of trimerizing aliphatic and aralkyl polyisocyanates selected from the group consisting of isophorone polyisocyanate, hexamethylene polyisocyanate, methylene bis cyclohexyl polyisocyanate, xylylene polyisocyanate, and mixtures thereof the improvement which comprises promoting said trimerization by a catalytic quantity of a fully substituted quaternary ammonium carboxylate having 1 to 2 hydroxyl alkyl groups attached to the quaternary nitrogen having the formula: ##STR40## wherein R 1 , R 2 , R 3 and R 4 are short chain alkyl groups having up to 3 carbon atoms, and R 5 is H, an alkyl group of 1 to 18 carbon atoms, alkynyl group of 2 to 15 carbon atoms, benzyl or methoxy benzyl.
Claim 30
Dependent Claim
215 words
In the process of promoting organic isocyanate condensation and/or polymerization reactions in the production of products containing respectively urethane and isocyanurate groups, the improvement which consists in utilizing for such promotion a catalyst quantity of a hydroxyl alkyl quaternary ammonium compound corresponding to the formula ##STR41## wherein R 1 , R 2 and R 3 are independently alkyl or hydroxyalkyl groups of 1 to 20 carbon atoms, or cycloalkyl groups of 3 to 8 carbon atoms, aralkyl, aryl, alkenyl of 2 to 20 carbon atoms, or alkynyl of 2 to 6 carbon atoms, or R 1 , r 2 and R 3 together constitute a heterocyclic structure from the group consisting of quinuclidine, N-methyl morpholine, N-ethyl morpholine and N,N'-dimethyl piperazine; R 4 is H, phenyl an alkyl group of 1 to 15 carbon atoms, an alkenyl group of 2 to 15 carbon atoms, an alkynol group of 2 to 6 carbon atoms, a hydroxy alkyl group of 1 to 9 carbon atoms, a keto alkyl group having a total of 3 to 15 carbon atoms, or an alkoxy alkyl group having a total of 2 to 20 carbon atoms and R 5 is H, an alkyl group of 1 to 18 carbon atoms, alkenyl group of 2 to 15 carbon atoms, benzyl or methoxy benzyl.
Claim 31
Dependent Claim
215 words
In the process of promoting organic isocyanate condensation and/or polymerization reactions in the production of products containing respectively urethane and isocyanurate groups, the improvement which consists in utilizing for such promotion a catalyst quantity of a hydroxyl alkyl quaternary ammonium compound corresponding to the formula ##STR41## wherein R 1 , R 2 and R 3 are independently alkyl or hydroxyalkyl groups of 1 to 20 carbon atoms, or cycloalkyl groups of 3 to 8 carbon atoms, aralkyl, aryl, alkenyl of 2 to 20 carbon atoms, or alkynyl of 2 to 6 carbon atoms, or R 1 , r 2 and R 3 together constitute a heterocyclic structure from the group consisting of quinuclidine, N-methyl morpholine, N-ethyl morpholine and N,N'-dimethyl piperazine; R 4 is H, phenyl an alkyl group of 1 to 15 carbon atoms, an alkenyl group of 2 to 15 carbon atoms, an alkynol group of 2 to 6 carbon atoms, a hydroxy alkyl group of 1 to 9 carbon atoms, a keto alkyl group having a total of 3 to 15 carbon atoms, or an alkoxy alkyl group having a total of 2 to 20 carbon atoms and R 5 is H, an alkyl group of 1 to 18 carbon atoms, alkenyl group of 2 to 15 carbon atoms, benzyl or methoxy benzyl.
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